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The History of Anna
All stories on this web site are purely FICTIONAL. The people depicted within these stories only exist in someone's IMAGINATION. Any resemblence between anyone depicted in these stories and any real person, living or dead, is an incredible COINCIDENCE too bizarre to be believed. If you think that you or someone you know is depicted in one of these stories it's only because you're a twisted perverted little fucker who sees conspiracies and plots where none exist. You probably suspect that your own MOTHER had sex with ALIENS and COWS and stuff. Well, she didn't. It's all in your head. Now take your tranquilizers and RELAX.
The History Of Anna
How about a quick trip down memory lane. I'd like to let you in on
how I got started. I have a sister and one day when I was about 13
and she was 18, I was pissing her off as much as I could. She made the
comment that she wished she had a sister instead of a brother and
became quite upset with me. I told her that she was stuck with me,
so she had better get used to it. She, on the other hand, had different
ideas. It was Friday and my parents had just left for a business trip
to the states, so we where all alone. Roxanne, my sister, (Hence the
name Anna), decided that I need to be taught a lesson.
On Saturday I awoke to my sister sitting on my bed. In her hand
was a list of all of the chores I had to do that day. I told her no way,
and she said that if I didn't do them, she would tell Mom and Dad
that I had been pure hell all weekend. I decided it was better to have
a little pain, then the gain would be from my parents. So I agreed to
do them. I was in the kitchen starting on the dishes, when my sister
tossed me an apron and told me to put it on. It was a frilly kind
that my Mom used when she was in the kitchen. I protested but put
it on anyway.
As I was washing, my sister made the comment that she had
thought about it and she was going to have her sister after all. I
told her she was nuts. How was she ever going to have a sister. She
said that since I made such a rotten brother, I would probably make
a better sister. I was a little unsure of what she wanted so I just
listened.
Roxanne said that I was going to find out what it was like to
have manners and she said that I was already on my way to being
her maid for a day. I started to protest again but she told me to
keep my mouth shut and to listen and obey her commands. If I
complained one more time, that was it. Mom and Dad would think
I had nuked the world. I decided that from here on in, I would have
to go along with my sisters wishes. After finishing the dishes, my
sister gave me a list of things I had to do.
I was quite shocked at what it said. It read sort of like this:
"Since you have failed to be a good brother to me, I will give you
a chance to be a good sister. And if you are going to be my sister,
you will have to look like one. First, shave all of your body hair off.
This includes your chest, armpits, legs and pubic hair. Second, fill
the bath tub up with water and add some bath oil to it. Soak for
half an hour. When done, go into my bedroom and use the items on
my dresser. Paint your toenails and fingernails. Pluck your eyebrows
at the corners. On my bed you will find clothes to wear. Put them
on in the order they are laid out. I am going to do some shopping
and will be back in three hours. You had better be ready or else!"
I was very confused, but another side of me was curious. I had
watched Roxanne apply her makeup on several occasions and it al-
ways amazed me how well she could do it and how much better she
looked when she was finished.
She also had a rather large wardrobe, with all types of clothes.
Since this was the start of the DISCO era, there was quite a few
shorter skirts and some spandex items. I also thought it unfair that
girls always got the soft, colorful clothes to wear, while we "GUYS"
had to wear the rough and tough stuff.
And last, but not least, I had wondered a few times what it would
be like to be a a good looking girl and have guys falling all over me.
I had seen a pic layout of she males in one of my Dad's Playboys,
and it had gotten me quite excited. The best of both worlds! So it
was with some apprehension and tons of excitement, that I started
on my first road to transformation. And I wasn't going to let on to
Roxy that I just might enjoy this adventure.
After a few close calls with the razor, I succeeded in shaving my
entire body. The tough part was pubic hair and anal region. I had a
hard time seeing if I was shaving, or about to cut off my manhood.
I don't think my sister would have cared if I did.
After I was done, I filled up the tub and poured a little too much
bath oil in it. I just about slipped and killed myself getting in. I
could see the headlines now " Nude and Totally shaved 13 year old
boy slips and kills himself trying to appease his sister!" The soak did
feel quite good and I just about forgot about the time.
I jumped out of the tub and covered my entire body with some
perfumed cream my sister had left in the bathroom. This was starting
to feel really nice and I couldn't help getting into it. I wandered into
my sisters bedroom and on the bed were, even by my standards,
some pretty sexy clothes. Where did she get this stuff???
I started off by putting on a full cup pink bra and pantie. I had
a little trouble with the bra, but figured it out eventually. I thought
I looked a little flat and then noticed two balloons filled with water
on the bed. I guess these were to be my boobs. I popped them into
the bra and they fit nice and snug. Then came the pantyhose. There
were sheer navy blue and I think I got tangled up in them three or
four times before I finally got them on straight. They felt wonderful
against my freshly shaven legs and I think I was starting to get a bit
excited.
I looked over into my sisters closet door mirror and was a little
surprised to see how well I was starting to look. I have always been
a small person, and at this age I think I weighed about 115 pounds.
My waist size at the time was 24 inches and I was only 5' 4" tall. I
turned my attention back to the bed full of stuff as my three hours
were just about up.
Next, I put on a frilly pink blouse that had a V-Neck. It took
me a minute to realize that women button there clothes up on the
opposite side. Next came a black skirt that stopped just above my
knee. After tucking the blouse in, I finished off my outer apparel
with a black wide elastic belt and then turned my attention to the
shoes.
They were about my size, black and had a three inch heel on
them. I sat down on the bed and slipped them on. Standing up was
a different story and finally walking in them was almost impossible.
I practiced back and forth around the bedroom until I got the hang
of it. I walked over to the mirror and was pleasantly rewarded with
my reflection. I must admit, I had a pretty good figure and my legs
looked wonderful with the heels, pantyhose and skirt framing them.
I thought that I should get back to work, so off I went to start
dusting the living-room. My sister arrived shortly after and was very
pleased with my novice attempt. She had quite a few bags with her
and I was a little more than curious as to what she had bought. She
told me to come into her bedroom and sit on the bed with her. She
said that this is how sisters got along.
I followed her in to the bedroom and we sat down on the bed.
She corrected me on my posture and showed me how a proper lady
crosses her legs. She then had me stand up and walk around her
room. I did quite well and I could tell she was pleased. After I had
modeled for her, she told me to sit down as she had a few presents
for me for being such a good sister.
I think the first bag was the best. Inside was a long blond wig with
flip up bangs. It was curly on the bottom and I was a little excited
about trying it on. Roxanne lead me over to her vanity and told me
she was going to teach me how to be a complete girl. She combed
out the wig and then positioned it on my head. In the next bag was
an assortment of cosmetics. She gave me step by step instructions
on applying my makeup. When I was finished, I could not believe
my eyes. Sitting in front of me in the mirror was a very attractive
looking girl. I was impressed with what Roxanne had done and told
her so. She said that the best was left for last.
As we walked back over to the bed, I was a little more than
curious as to what was next. In the next bag was an assortment of
lingerie. A beautiful black bra with lace on the cups, a garter belt
and matching thong style panty. There were also two pairs of sheer
silk nylons. One black and one dark beige. The last item was a waist
chincher that laced up in the back. Roxanne explained that these
items were for later but would not tell me why or what for.
The next bag contained a feminine douching bag with a long
slender attachment. I was starting to become a little more then
curious. There was also a set of false nails and some perfume. The
last bag held some things I had never seen before. The first item
was a long pole that Roxanne called a dildo. It was eight inches long
and I was going to ask her what it was for, but thought she would
probably be getting around to descriptions later. The next item was
what she called a butt plug. I didn't have to be a genius to figure
that one out. The next item was another dildo, but it was a lot
longer and had two heads.
The last item was something in a tube called K-Y jelly. My
curiosity had peeked by now so I asked Roxanne what she was going
to do with all of this stuff. She smiled and said it wasn't what she
was going to do with it, it was what I was going to do with it.
Now it was time to really wonder what my sister was up to, but
before I cold say anything, she told me that it was time for me to
start dinner. Cook??? I had never cooked before. That was why
we had women. She reminded me that since I was now a woman, I
would be doing the things that women did. So off to the kitchen I
went to prepare dinner. Roxanne said that she was going to have a
bath and relax.
I was just starting to peel the potatoes when I heard my sister
come out of the bathroom. She said that she was going to get dressed
and would join me in a couple of minutes. I was standing at the sink
for about five minutes wondering how a girl could wear these high
heels for so long when Roxanne came up behind me. She slipped her
hands around my waist and I could feel her move her hips against
my bum. She said that I was the perfect sister and she wanted to
reward me. I turned around and just about didn't recognize her. She
was wearing a skin tight leotard top with an even tighter skirt and
boy was it short. She had on black nylons and at least 5 inch heels.
Now my sister is a very good looking woman, but she had really
outdone herself this time. Her blond hair was all teased up and she
smelled wonderful. She asked me if I liked the way she looked and
I said she looked great. She then pulled me very close to her and
kissed me full on the lips. I was shocked, but aroused at the same
time. I could feel my penis start to grow and I think she could to.
As we kissed, Roxanne ran her hands over my ass and then up
under my skirt. Just as I was beginning to get used to all of this, she
broke away and said that dinner could wait. She lead me back into
her bedroom and told me to sit down on the bed. She then removed
my shoes, lifted my skirt and took off my pantyhose and panties.
While she was doing this, she explained to me that she had dis-
covered when she was fourteen that she was bi-sexual. It had hap-
pened on a camping trip with a friend of hers. I guess they had
slept in the same tent together and one thing lead to another and
presto! My sister had diverse interests. She had been with quite a
few other woman since that time and had even been involved in a
few three-somes, another woman and a man.
She explained that in her mind, making love was a beautiful and
exciting thing and it did not matter who you were with as long as
the outcome was pleasurable. It made sense to me, but I still could
not figure out what she was up to. It was all to become quite clear
over the course of the next few hours.
After she had finished talking, I was still unclear as to what was
next and asked her what we were going to do. She told me to take
of the rest of my clothes except for my bra and wig and to put my
heels back on. Then we went to the bathroom and Roxanne told me
to to face the tub, bend over and spread my legs apart. She said that
this was phase one of becoming a total girl. I couldn't help feeling a
little embarrassed and quite submissive at having my ass, cock and
balls fully exposed. She ran her hand between my legs and started
to caress my cock, which was starting to get really big. Bigger then
I had ever seen it. Roxanne said that she was going to flush me out
so that I would be nice and clean.
With that in mind, she filled up the douching bag with some
warm water, inserted the slender attachment into the end of it and
put a little of the K-Y jelly on the tip. She said that it might be
uncomfortable at first, but that I would get used to it and more then
likely really enjoy. She also told me to hold on for as long as possible
before I had to go to the bathroom. Now up to this point, I had gone
along with everything she had said, but this was starting to sound
extra weird.
I turned to Roxanne and said that I was very nervous about all
of this. She smiled and told me to relax and not go away. She
disappeared for a minute or so and came back with a joint. I had
never smoked drugs up to this point so I was unsure of what I was
in for. Roxanne gave me two puffs off the joint, told me to hold it in
for as long as I could, and finished the rest herself. My head started
to float and my whole body became one big nerve ending.
She told me to bend back over and I couldn't help my giggles.
I was thinking about the fact that my body was starting to feel a
little numb, and didn't even notice Roxanne inserting the douching
apparatus until she squeezed the bulb. The feeling of the water
rushing into my anal track was wonderful and before I new it, she
had another bag full for me. I think I was able to keep three bags
full of water in me until I couldn't hold it anymore.
I quickly spun around, plopped down on the toilet and expelled
my entire bowel. We repeated this maneuver about eight time before
Roxanne said that I was fully flushed out. I felt great and was ready
for whatever else she had in mind.
She then said that since I was leaning how to be a girl, I had to
be loose and ready for anything. On that note, phase two started.
The butt-plug was produced and gently inserted into my anus. I
marvelled at how good it felt and the way my bum could grip it at
the base. I told my sister that I had never imagined having something
up my ass good feel this good. She quickly corrected me, saying that
I could not think that way anymore. She said that from now on, my
ass was my cunt and my penis was my clit. She also told me to pick
a girls name that she would call me. I thought it over for a minute
and then said I liked Anna because it reminded me of her. I guess
she was pleased with my choice and said that we could now go on to
phase three.
We went back to her bedroom and she told me to sit down on the
chair in front of the vanity. She then re-did my makeup, a lot more
this time, and applied the false nails to my fingers. All this time,
my butt plug was working itself around inside of me and my clit was
beginning to get big again. My sister could not help noticing this
and said that it would not do for a girl to have a bulge under her
dress. On that note she knelt down in front of me and started to lick
and suck me. I could not believe how good it felt and came into her
mouth quickly. She stood up, leaned over and kissed me. I could feel
her tongue pushing my cum into my mouth. The taste was different
from anything I had ever had before and found I quite enjoyed it.
Licking her lips, Roxanne finished doing my nails, painted them,
painted my toenails and covered my entire body with perfume. She
gave me some clip-on earrings, a gold necklace and bracelet and two
of her rings to put on. After she was done, she said I looked great
but now it was time to make me look sexy. Back to the bed we went
to start my final dressing. Roxanne showed me how to put on the
lingerie correctly.
First the waist chincher, then the garter belt. I pulled on the black
stockings and rolled them up my leg. The feeling was incredible.
After I had attached them to the garter belt, next came the panties
and bra. Roxanne showed me how to tuck my balls up into there
sockets and pull my clit back. After the panties were snugly in place,
I took off the pink bra and replaced it with the black one. I refilled
it with the balloons and Roxanne told me it was time to pick out my
party clothes.
She opened up her closet and told me the best part of being a girl
was attracting other people. And if I was going to do that, I would
have to dress so that I would be noticed. She then said it was up to
me as to how much I wanted to be noticed.
I had a hard time deciding what to wear. Doesn't every girl!! I
finally picked out a black mini dress with a dark blue collar. I slipped
it on and then had to pick what shoes I wanted to wear. I decided
on a pair of four inch open toe heels with a sling back. I put these on
and my sister handed me the belt I had been wearing before. Having
finished my transformation, I could not help looking at myself in the
mirror. What I saw was a very sexy looking girl with great legs, if I
do say so myself. My sister said that she couldn't be more pleased
with my look and that I was turning her on. She then looked at the
time and said we had better hurry up or we were going to be late.
I couldn't help being nervous. Late for what, I said. She then
informed me that phase four was about to begin. We were going
out to a club that she liked that catered to people with different
ideas. How different, I said. Roxanne explained that there were a
few bars/clubs in town that were setup for gay and bi people. She
said that it was the perfect place to start if I was going to see if I could
pass in public. I reminded her of my age, but she just laughed. She
said I looked older and people didn't really care anyway. I thought
what the hell, I've come this far, might as well go all the way.
I borrowed Roxanne's black trench-coat and purse and she wore
a white fun fur jacket. As we drove to the bar, the name of which
escapes me, Roxanne explained that she was going to introduce me
to some of her friends. They all knew it was my coming out and
decided that it should be special. Now I was getting really excited.
We smoked another joint on the way and by the time I got there
I was ready for just about anything. Roxanne said that I would have
to be careful around other people in the bar as there would be some
straight folks who went there. She also said not to talk to much or
to loud as my voice, though rather high, was not feminine enough.
What I did with myself the rest of the time was up to me. She said
that there was only one stipulation to the evening. I had to go home
with her. I said no problem!
We had to park about half a block from the club and I think it
was the longest walk I have ever taken. It was around nine pm and
we passed several people on the way. We had a couple of guys say Hi
and I think I melted. Roxanne just smiled and kept walking. I was
relieved to get to the door, but not knowing what to expect, was still
really nervous. We walked inside and the doorman knew my sister.
They talked for a minute and then she introduced me as Anna,
her sister. He smiled said hello took my hand and kissed it. It felt
wonderful to have all of this attention, but all I could do was to say
hello under my breath as we gave him our coats.
Inside, the music was pounding. The light show over the dance
floor was the best I had ever seen and the place was packed. As we
made our way over to a table full of Roxanne's friends, I felt hands
on my bum twice. The music, the lights, the butt plug, the smoke
and now strange hands groping me increased my excited state. All I
wanted was more of the same. At the table I was introduced around.
I was quite surprised that the women were very attractive and all
dressed quite sexy. I got to sit in the middle of two of the best
looking ones and had to remember to cross my legs.
Old habits die hard!! . On my right was a girl named Rachel and
on my left was a girl named Connie. I only remember their names
as I could barely hear the others around me. Both seemed very nice
and they talked to me about how I felt that night.
I told them both that at first, I wasn't too crazy about the idea,
but that now I was loving every minute of it. Connie asked me if I
had a special friend inside of me. I guess I looked a little taken back
and she said that Roxanne had told her what she had bought for me.
I shyly admitted that I had a butt plug stuffed up my cunt and she
laughed. She said that if I liked it, she would see if she could find
something else to replace it with. I wasn't to sure what she had in
mind but smiled anyway.
As the second round of drinks appeared, I was starting to feel
a little tipsy. Connie had her hand on my leg and was rubbing the
inside of my thigh. My clit was starting to strain from the delicious
feelings I was experiencing, and I whispered this fact to Connie. She
said that if I wanted a rest, was there anything I would like to do,
like maybe I could caress her leg. I looked at her and did find myself
attracted to her. She had shoulder length blond hair, blue eyes and
was wearing a short black leather skirt and a black silk blouse. She
had fishnet stockings on and the highest heels that I had ever seen.
I said that I would like to return the favour and she took my hand
and placed it on her knee.
The table had a long table cloth on it and the lights were fairly
dim so I knew nobody would know what we were up to. I moved my
hand gently along her thigh, back and forth. She seemed to like it
and then took her hand and moved my hand up under her skirt.
It was very exciting as I reached the tops of her stockings and then
felt her panties. They had soft lace on them and Connie seemed to
enjoy my touch. As I was getting used to all of this, she asked me to
remove my hand for a moment while she went to the bathroom.
I had a few sips of my drink and waited for her to come back.
She was only gone a few minutes and when she sat back down she
said to me that she had to go and remove her panties as they were
starting to creep up on her. I was happy to have her back and again
proceeded to run my hand under her skirt. Waiting for me this time
was something quite hard. It took a moment for it to register, and
then I realized that this was a penis, or clit, or whatever the hell we
were calling them that night.
I started to withdraw my hand but Connie put hers on mine. She
asked me if I thought she was any less attractive now that I knew her
secret. I said not really. She then said that she found me attractive
and she wanted to get to know me better.
She said that girls like us had to stick together. By this time,
I couldn't disagree so I moved my hand back to her clit. I started
to move up and down the shaft and Connie purred in my ear how
wonderful it felt. I was starting to get into it when she asked me
to stop. She said it wouldn't be very lady like for her to have cum
running down her leg. She then asked me if I would like the same
done to me. I quickly agreed and she took me by the hand and lead
me off to the bathroom. As I was getting up my sister looked over
and asked me if I was having a good time. I said I think I was, and
she just winked at me.
I just about walked into the men's washroom and it was a good
thing Connie was with me. Once inside the bathroom, she turned
and locked the door. She then told me to take off my panties and to
remove my butt-plug. After depositing everything onto the counter,
Connie told me to bend forward onto the sink and to spread my legs.
She commented on my beautiful ass and slowly lifted my dress up.
As I leaned forward more, Connie took a hold of my clit in one hand
and started to finger my cunt with the other. My knees just about
collapsed from the intense sexual feelings I was having. She inserted
one, then two, then three fingers into me and pumped them in and
out in time to her other hand. I cried out as I exploded all over her
hand and the counter.
After I was finished, Connie told me to clean up, fix my hair put
my butt plug back in and my panties on. She said that she would
meet me back at the table. I could hardly stand and the feeling of
the plug going back into me was almost to much.
I did make it back to the table and had two more drinks. We
spent about another hour orso talking and Roxanne decided that we
should get back home. Connie told me that she would like to see me
again and said that she would phone Roxanne when she was free.
I said sure and asked her to call me instead. I confessed that I
liked her and wanted to see her again, too, She smiled, gave me a
kiss on the cheek and said that she would love for me to come over
to her apartment and spend the night doing girls things.
We said our good-byes and walked back to the car. Roxanne
asked me what I thought of Connie and I said she was something
else. She said that we had a lot in common. Connie was a virgin
to anything bi and this had been her first night out. Rachel was
her Mistress and had been preparing Connie for this night. I was
surprised that she was a novice but Roxanne told me that Rachel
had taught Connie a trick or two.
We arrived home and I was getting a little tired. Roxanne told
me to go into her bedroom because I was going to sleep with her
tonight. She told me to take off my dress and panties, remove my
butt plug and to slip on her black dressing gown.
I came back from the bathroom and Roxanne was lying on the
bed wearing her white garter belt and stockings along with a pink
teddy. The crotch of the teddy was snapped open and she was softly
playing with herself. As I approached the bed she asked me if I
thought she looked sexy. She looked more than sexy and I told her
so. She then asked me if I wanted to fuck her. Or would I rather
have her fuck me. I couldn't make up my mind, so I said yes to both.
She asked me to take off my shoes and lay and the bed next to
her. She asked me how I had felt about the night and quite honestly,
I had really had a good time and told her so. She asked me what I
thought of Connie and I said that I was amazed that she was a he.
Roxanne said that Connie had told her that I was very cute and sexy
and she wanted to have some time alone with me. She said that I
would be the first "Girl" that Connie had ever been with. How did I
feel? Well, I said I was sort of honored that she (or he) thought me
attractive and admitted that I loved what she (I guess) had done to
me in the bathroom. Roxanne asked what that was, so I explained
my adventure. As I talked about it, she kept rubbing her crotch and
fingering herself. When I got to the part about Connie putting her
fingers in my cunt, Roxanne started to moan softly.
I finished my story and I think Roxanne was starting to cum.
She was sliding her fingers in and out of her now very wet slit and
between her moans she asked me to lick her where her fingers were.
Since I was new to all of this, I had some help from Roxanne as to
wear to lick and how hard and soft. I found her clit with my lips and
started to suck her gently. A moment later her hips griped around
my head and she screamed out. I thought I had hurt her but she just
laughed and said that it was just the opposite. Then she said it was
my turn. The final phase of learning about being a girl.
I was instructed to kneel facing the headboard, grip it with my
hands and spread my knees as far apart as they would go. Roxanne
started to stroke my clit and tell me what a good girl I was. She said
that my ass looked so sexy but lonely and I should have a nice big
cock in me.
She asked me if I wanted a cock inside of me and all I could say
was yes. She then inserted two of her fingers and started to play
with me. I tried to move my bum back so that they would penetrate
deeper and I knew that Roxanne knew that I was enjoying myself.
She then pulled her fingers out and asked me if I was ready to become
a full woman. I said yes again but this time much louder. With that,
I could feel the tip of the dildo against my cunt and then before I
knew it, up and inside of me.
I cried out as she pushed it in, deeper and deeper with each stroke
but all I could think of was spreading my knees further apart so that
I could take more. She asked me if I liked being fucked and I said
yes, over and over again. She told me that I was being such a sexy
little slut, but that she wanted to be fucked to.
With that, she told me to turn over and lay on the bed. I could
feel the dildo, all eight inches, deep inside of me and thought for sure
I was going to cum. Roxanne moved over top of me, took my now
very hard clit, and guided me into her wet warm vagina. The feeling
was electric and as she pressed her full weight against me, the dildo
hit home.
We both came at the same time and screamed so loud I thought
we would wake the neighbors. I was so exhausted that all I could
do was lay there and shake. Roxanne purred and moved off of me,
removed the dildo from my now very tired cunt and said that from
here on in, I was going to be her sister when we were alone. I didn't
have any objections and we feel asleep snuggled up to each other. The
next day I awoke and thought the whole thing had been a dream.
One look at my body and trying to get my long hair out of my face
convinced me otherwise. That was the start of many wonderful and
highly sexual times that my sister and I shared.
My sister has since moved out of the country, but we see each
other at least twice a year. I did meet with Connie a few times,
but will same those adventures for letters to come. As you can see,
my start into the world of TVism was greatly helped by a few other
people. I have never regretted a minute of it and just about all of
my experiences have been wonderful. I say just about, because there
have been a few times when I was just about discovered, but later
on this topic.
As I said last time, the first night I had gone out as Anna, I met
another TV named Connie. She had expressed an interest in me,
that was, to say the least, a little more then friends. Roxanne had
told me that Connie wanted to get together with me, just me, for a
night of girl fun. I was starting to catch on quick as to what "Girl
Fun" was all about.
On Wednesday of the following week, I came home from school
and had a rather burning desire to dress again. Roxanne and I had
not really talked about it as she was working a late shift and we
seemed to pass each other in and out. I really did want to try being
a girl again and when I came home that day, Roxanne had already
left for work. I decided that since I was all alone in the house, I
could experiment all I wanted. Roxanne had already told me that
the middle drawer in her dresser was for my things and that I could
borrow her clothes anytime I wanted to.
After having my bath and shaving myself totally again, I decided
to try the douching part on my own. I must have spent an hour filling
myself up and cleaning myself out. Once I had started, I didn't want
to quit. It really does feel wonderful and you should try it sometime,
sweetheart. The big test was to see how much water I could hold
inside and for how long. After I was done, I went to my sisters
bedroom and started to prepare myself.
I decided not to wear my butt-plug and went straight to applying
my makeup. After a few trials and errors, I succeeded in coming close
to repeating what my sister had accomplished on the weekend. I then
placed my wig on my head and decided to style it a bit differently.
To this day, I still wear my bangs combed to the side. I think it
makes me look a little more sexy. What do you think??
After my hair was in place, I went to my drawer and picked out
my lingerie. I dressed slowly, loving the feel of the undergarments
and especially the stockings. Again, the big question was what to
wear. I picked out a very frilly white blouse and decided to wear my
sisters short black leather mini skirt. It hugged my hips and really
showed off my legs. Then I slipped on Roxanne's 5 inch heels. They
felt wonderful on and pushed my hips forward. I walked around the
room, became used to them and then stood back from the mirror to
admire myself. I thought I looked pretty damn sexy and started to
run my hands up and down my body. This did a lot to arouse my
clit and I decided to cool down a bit and watch some TV.
About 8 o'clock the phone rang. I answered and this sexy voice
on the other end asked if Anna was in. For a minute, I was petrified.
I couldn't speak, so I just mumbled that I thought they had the
wrong number. The voice paused and then said was I sure and that
it was Connie calling.
I immediately snapped out of my haze and said yes, she had the
right number and that she was talking to Anna. Connie laughed and
said that she was sorry for startling me. I said it was okay and that
I'm sure I would get used to it. She then asked me what I was up
to that night. I told her about getting dressed and she said that she
had done the same. Would I like to come over to her house?
Again, a frozen state came over me and I didn't know what to
say. There was a long pause on the other end of the telephone and
finally Connie said that she could pick me up and would promise not
to keep me out to late. I decided, what the hell, and told her sure,
why not. She sounded pleased and said that she would be over in
an hour. After I hung up, I franticly ran around the house, trying
to fix my makeup, decide if what I was wearing was okay and about
a million other things. I eventually calmed down, only to hear the
doorbell ring. My heart stopped and it was all I could do to peek out
the back window. Thank God it was Connie. I thought that maybe
friends of my parents or sisters had come over.
As I let her in, I could not help noticing how good she looked.
She was wearing a short coat and under it a short black lace up dress.
She had black stockings on and those wicked high heels. Her hair
seemed longer and I asked if it was different from the weekend. She
said yes, and that she had five wigs, four blond and one brunette.
She then said that I was welcome to try any of them on. I asked
her if she wanted something to drink but she mentioned that if I was
going to be home on time, we had better be going. I grabbed one of
my sisters coats and a purse and off we went.
Connie lived in an apartment building downtown, so we parked
in the basement and took the elevator. I didn't think about it much
until it stopped on the main level. I freaked when I realized that
somebody was going to get on. Connie noticed my panic and moved
closer to me. The doors opened and in stepped an older gentleman.
He smiled at us and said good evening ladies. Connie smiled back
and I just waited out the longest elevator ride of my life.
As it was, our floor was first on the stops. We left the elevator
and I could hardly walk. This was the first time I had ever been that
close to somebody who did not know who I was. In a way, it was
quite thrilling. Once inside Connie's apartment, I started to relax.
She made us drinks and it was the first time I had tasted rum and
coke. She told me to sit down on the coach next to her and tell her
all about how I felt being a girl.
We talked for quite a while and eventually the topic turned to
sex. Now how did it get there I wonder??? The conversation changed
when Connie asked me if I thought she passed as a woman. I had to
admit that she made a very fine looking girl and told her that. She
then said that she had been dressing for quite a while, but had never
really had the guts to go out in public. She was very submissive by
nature and her mistress and turned her on to dressing up. She said
that the only thing she had not done as a girl was have sex. She then
asked me if I had.
I told her that up until last weekend, I had been a virgin to
anything and that my sister had taken my cherry as far as my clit was
concerned. Connie seemed very interested as to what had happened
between my sister and my self. She asked me to explain our night.
I told her about getting into bed and making love to her, and then
her making love to me. I knew this was turning Connie on so I went
into graphic detail as to the night. Connie started to play with my
legs and then pulled me very close to her. She kissed me full on the
lips and then I felt her tongue in my mouth. We kept on kissing as
we moved hands over each other bodies.
My clit was starting to strain under my leather skirt and I knew
Connie could see it. She moved off the coach onto her knees, lifted
up my skirt and start to lick me. Her mouth felt so good and it
was all I could do to keep from coming. She looked up at me and
asked if something was wrong. I laughed and said, what could be
wrong. She said that I was holding back and she really did want me
to come. I decided that okay, if she wanted it, she was going to get
it. As she started to suck me again, she inserted one of her fingers
into my cunt. That was it. I couldn't hold out any longer and came
so hard my toes cramped. I think Connie was happy, but I really
didn't notice anything else.
After my orgasm had subsided, Connie came back up onto the
coach. I could see that her clit was hard as it was framed against her
dress. I asked her if she wanted me to do the same to her and she
moaned yes. I got down on my knees in front of her and she lifted up
her dress and spread her legs. It was the biggest clit I had ever seen
and thought for sure I was going to choke to death. Connie guided
me to her and taught me how to suck her slowly so that I could open
my throat and take her deeper. After a couple of minutes, I got the
hang of it and could swallow her almost all the way. This kept up for
a lot longer than I did, and she kept moaning and squirming around.
I thought for sure she was going to cum, but she never got there.
As my mouth was getting tired I stopped for a moment and told
her that she was not letting go, just like I had tried to do. She said
that she just wanted the feeling to last, and then said that she would
rather cum deep inside of me instead of in my mouth. She then
asked me if it would be all right to make love to me. I wasn't to
sure about this, but Connie said that she would wear protection so
that everybody stayed nice and clean. I decided that if I was going
to learn how to be a girl fully, this was the final test. So I said yes,
and Connie got up and lead me into the bedroom.
She asked me to take off my skirt but to leave everything else on
including my shoes. She then lead me to the bed and asked me to
lay down.
As I lay there she again started to suck me and before long my
clit was rock hard. She kept saying how beautiful my clit was and
how she was loved to suck it. I was feeling no pain and just lay
there moaning. Then she turned me over so that I was on all fours. I
could feel her fingers against my cunt and then felt the KY jelly being
inserted. Connie paused and took from the night table a condom. I
could hear it rip open and then I felt her clit against my cunt. It was
very slippery and I was unsure if she was going to put it in or just
tease me. Then I felt it start to go in. And boy, did I feel it!!!
She was huge and I thought I was going to be torn open, but the
feeling of pain lasted for only a moment. Then she was inside of me
and it was all pleasure. I bucked my hips back to meet her thrusts
and she started to ride me. Slow at first, and then faster. Each time
she pushed into me, I felt her get deeper, until I thought I was going
to pass out from the delicious feelings that were raking my body. I
was moaning for her to fuck me harder and she was moaning that I
felt so good. As she started to reach her climax, she grabbed my clit
and started to stroke it. This was too much for me, and I came into
her hand and onto the bed. The fact that I was coming triggered
Connie and she yelled out as she bucked one last time.
I was a little dazed and rolled over on the bed. Connie curled up
beside me and started to stroke my thighs as she whispered that I
was everything she had dreamed of. I was certainly impressed with
her and we lay in bed for about half an hour before I realized what
time it was. I told Connie that I had better get home or Roxanne
would have a fit. We jumped out of bed, dressed and she drove me
home. I was having a hard time walking after my encounter and just
about slipped coming up the stairs. When I walked through the door
Roxanne was in the kitchen. And so was a girlfriend of hers from
work.
I tried to go downstairs, but Roxanne called out that Anna should
be a good sister and come and meet her co-worker. I was a little
embarrassed but walked into the kitchen anyway. The girl from work
was nice and commented on the way I was dressed. She asked if I
had been out at a party and I just shook my head. My sister excused
me from the room and said that since I had school tomorrow, I had
better get to bed. She said that since last weekend, her sister was
a different girl. Her friend just nodded knowingly and I went to my
bedroom. It was the start of many wonderful times with my sister,
Connie and a few other special people. More on these times in my
next story!
Like I said before, I did have a few other times with my sister and
some of her friends. After my first introduction to dressing and
subsequent visit with Connie, things in the female department for
me slowed down. My parents had only been gone for a week, so by
the next weekend, life was pretty much back to normal. I, however,
still tried to dress as much as I could, but it wasn't much.
About four months later, my sister decided that she was going
to move out. There were many heated decisions with my parents on
her living with roommates, and my Dad was not thrilled with her
choice of people. One guy and one girl. He however gave in after my
sister let him pay for their first six months of rent, insuring that they
moved into a very nice townhouse in the better part of town. The guy
and the girl were boyfriend and girlfriend so this at least appeased
my parents. They did not know that this couple and Roxanne had
been sexual partners for a while and if they did, I'm sure they would
have both had coronaries.
I was very sad to see my sister leave, but she promised that I
could visit as much as I wanted and since the townhouse had three
bedrooms, I could have one all to myself. She said that it would be
Anna's room and I could fill it with all the clothes and girl things
that I wanted. This was so exciting that I forgot about the fact that
she was leaving and started to plan out my new room.
Of course, I helped Roxanne to move and finally got to meet her
roomies. They were both very nice and I liked them from the start.
Gail was 22 and worked as a waitress while she went to university
taking her nursing. She was good looking, long brown hair and always
wore tight jeans. So tight, in fact, I could see her pussy lips etched in
the fabric. Matt, her boyfriend, was 24 and working as an Engineer
with a large oil company. He was also very good looking, reddish
brown hair and deep green eyes, about 6 feet and 170 pounds. He
worked out a lot and had a very muscular body.
After we finished moving Roxanne in, she told me to come up to
"My" bedroom. In it was a twin bed, vanity with mirror and a six
drawer chest. There was frilly pink curtains on the window and a full
length mirror on the closet door. She had told Mom and Dad that
she needed the furniture because her friends from out of town would
stay over sometimes. I guess Dad thought that it was better to have
whoever sleep in another bed then with his daughter. It was exciting
having a place just for me and my sister saw that I was pleased. She
told me to open the drawers and the closet.
In the top drawer I found an assortment of pantyhose, nylons and
a pair of fishnet stockings. The second drawer contained four or five
pairs of panties and three bras. The third drawer held two full slips
and and a half slip. In the forth drawer was my original lingerie that
Roxanne had bought for me. The fifth drawer contained my original
wig and a new one that was long and black. The final drawer held my
dildo, my butt plug, the douching apparatus and a new 10 inch dildo
that looked exactly like a cock. In the vanity was a wide assortment
of make-up, false nails, nail polish and some perfume. The closet was
the best. A wide variety blouses, skirts, pants, dresses and two new
pairs of high heels greeted me. I was, to say the least, floored by all
of the clothes.
I thanked Roxanne for all of the stuff, but told her that she
shouldn't have spent so much money on me. She said that she and
purchased some of the things, like the wig and dildo, but the other
things were hand me downs from herself and Gail. I looked at her
and asked her if she had told Gail that I was her part-time sister and
she said yes. She had told both Gail and Matt and they were excited
to see me dressed. I blushed and got embarrassed but Roxanne as-
sured me that both Gail and Matt understood everything and that
the three of them had been lovers for quite some time. I relaxed a
little, but was still unsure about all of this.
My sister left me alone to set up my room the way I wanted to
and after about fifteen minutes, I joined the three of them in the
livingroom. They were planning a house warming party for the next
weekend and Roxanne told me that I was invited. She said that I
could spend the whole weekend with them and had already told Mom
and Dad that she needed my help to get organized. It sounded like
fun and Matt and Gail told me to come to the party as Anna. They
said that there would be a lot of people coming over and it would
be a great time. Matt said that since Roxanne had told them about
me, they were very curious to meet this Anna girl and from the look
in Matt's eyes, I think him more so than Gail. Roxanne said that
Connie was coming along with a few other TV's, so I would not be
alone as far as that was concerned. What could I say, except yes.
From the first time I had dressed, I just wanted to do it more
and more. It was so thrilling to be able to become an attractive
female that I had found myself fantasizing about what it would be
like to be with a man. I planned to have my chance on the following
weekend and all during the week, I thought of nothing else. I kept
my body shaved and wore my butt plug everyday. As the weekend
approached, I thought I was going to burst with excitement.
On the Friday night, I packed my things for the weekend and
Roxanne came over and picked me up. We went shopping and bought
a bunch of food for the next night. We also went to the drugstore
and picked up some condoms, bubble bath, a fresh tube of K-Y Jelly
and a couple of Fashion magazines. Roxanne said that the next day
was all mine to get ready but that she and Gail would need help that
night to prepare the food. When we arrived at her house, Matt came
out to help unload the groceries. After we were done, I went to bed
early. It was going to be a long day and night tomorrow, so I wanted
to get plenty of sleep.
The next day I awoke and went down to the kitchen. I was
surprised to see Gail making coffee, with nothing on except for a
skimpy robe which barely covered her bum. It was open quite a bit
at the front and I could not help looking at her breasts. She greeted
me and noticed my stares and smiled. She asked if I thought she
had a nice body and I said yes, and as I did, Matt walked in with
nothing on and a huge hard on. He grabbed Gail and said that she
had better come back to bed as he was horny as hell. They both left
the kitchen and I found myself quite excited by all of this.
After having breakfast with Roxanne, she asked me what I had
planned for the day. I told her that I was going to read through the
magazines we had bought and spend time on myself, getting ready
for the party. Roxanne was off to do some more shopping so she
would see me later. She handed me a bag and told me not to open
it until after she had left.
After doing up the dishes, I retired back to my bedroom and could
hear Gail and Matt still going at it. He was calling her all kinds of
names and she didn't seem to mind it at all. She kept moaning and
groaning and before long their love making came to a head, so to
speak. I heard them get up, shower, get dressed and leave. Before
they left, Gail poked her head into my bedroom and said that they
would be gone for about four hours, so they would see me later.
She was wearing another pair of those tight jeans and a very skimpy
halter top. One very fine looking lady and I thought Matt was quite
lucky to have her as a girlfriend.
After they had left, I remembered the bag that Roxanne had
given me. I opened it up and found two magazines about TV's. I'll
never forget the name of them. "Chicks With Dicks"! Very poetic. It
featured all sorts of TV's in different poses and with different clothes
on. I was getting very horny looking at the pictures, so I turned my
attention to the third item in the bag.
It was sort of an instruction book on how to be a TV with in-
formation from applying makeup to tucking your balls correctly and
pulling back your penis to give you the look of having a vagina. I
read the whole book and learned and incredible amount of informa-
tion on dressing, especially since it was geared to men looking like
women.
After finishing the book, I looked over at the clock and it was
already 3 pm. I decided to shave my body, douche myself and then
take a long bubble bath. When I shaved this time, I shaved off all
my pubic hair, something I had learned from the book. To be quite
honest with you girl, I will never do this again. It feels wonderful
for the first day, but unless you keep it up, it itches like hell while it
grows back!!! I have never completely shaved my pubic hair since.
I was getting out of the bath when everybody started to get home.
Roxanne came up to see how I was doing and told me to take off my
robe so that she could check me out. She was very pleased with my
shave job and fondled my balls lightly. She then told me to bend over
and checked out my rear. As she caressed my bum, she said that I
had a very pretty cunt and that hopefully it would not go unnoticed
that night. I secretly hopped so, too.
After Roxanne left, I started to get ready. I inserted my butt plug,
tucked up my balls into their sockets and pulled back my penis like
I had seen in the book. I put on the black bra and waist chincher,
followed by my garter belt and the fishnet stockings. I put on a
pair of tight panties, and it worked. My crotch area looked just like
Gail's, with full lips and all. I filled the bra cups with the water filled
balloons and went to the vanity to start my makeup. After finishing
my face, I sprayed my body with perfume including a quick spirt in
my crotch and one behind the backs of each of my knees.
The tough part was what to wear as far as clothes. I didn't really
know what everybody else was wearing, so I decided that I would go
all out. I picked out a pretty party dress that was bright pink taffeta,
the bottom of it stopping just above my knees. It had a back zip and
I had quite the time trying to get it done up. It had a side slit and I
was pleased to see that my leg showed through almost to the top of
my nylons. The shoes I picked where new, pink to match the dress,
and of silk material. They had a four inch heel and looked wonderful
on my feet. I combed out my blond wig and set it in place. I finished
off my transformation with earrings, a gold necklace and an ankle
bracelet. After putting on the false nails and painting them, I was
ready for the party. I stood back from the mirror and was pleased
and excited with my look. I hopped it wouldn't go unnoticed.
I walked down stairs and met Gail and Roxanne in the kitchen
making trays of food. They were both wearing dresses, so I felt a
little more at ease. Roxanne commented on my excellent choice of
clothes and Gail said that if she hadn't seen me, she would have
never have believed it.
As we talked and prepared the food, Matt came in. He stopped
and for a moment stared at me. He then turned to Gail and asked
her who her friend was. We laughed and Roxanne told him to say
hello to her sister. He looked at me again and gave me a wonderful
wolf whistle. He then told me to turn around and model for him.
After I was finished, he said to Gail that the dress and shoes looked
better on me then it had ever looked on Gail. I thought for sure she
would be mad, but she smiled and said that he was right, and she
had a bunch of other clothes that would fit me. I was thrilled that I
was so appealing to both male and female and happy about getting
more clothes.
We spent the next hour getting the house ready for the guests,
and around eight o'clock the first people started to arrive. I played
maid for the first little while, fetching people drinks and putting out
the food. Roxanne introduced me to everybody as her sister, and I
even met her boss and his wife. I was sure that nobody knew who I
really was and the party was in full swing when Connie arrived.
She looked great and we talked in the kitchen for a while. I told
her all about my own bedroom and the clothes and stuff and she was
very happy for me. I promised her a tour later and she pinched my
bum and said it was a deal, as long as it was an intense tour of my
bed.
By about eleven, I think around fifty people had showed up. The
place was packed and for the first time that night, Matt came over
to me and asked me how I was doing. I said fine and told him I was
getting a little drunk from the wine. He then looked at me and said
that the only way you could clear your head, was to give head. I
laughed and said in a teasing way, why, whatever do you mean???
He just took my hand and lead me from the room and up the stairs
to his bedroom. I could see Gail watching us, but she smiled and
waved good-by.
When we got to Matt's room, he turned and closed the door. I
asked him if we should lock it and he said that nobody would come
in. He then placed his arms on my hips and drew me closer. He told
me that I made one hell of a fine looking woman and he had been
hoping to get me alone all night. I asked him about Gail and he said
that he had already told her what he wanted to do to me and she
had said that it was fine with her.
As we talked, Matt pulled me closer until I could feel his cock
against my tummy. I asked him in a whisper what he wanted me
to do and said that he wanted my lips around his cock and then he
wanted to fuck me.
I pulled away from him and told him to wait a moment, as I had
to go to the bathroom. I bolted from the room, went to the bathroom
and removed my butt plug. I checked my makeup and then walked
back to the bedroom. Once inside, I found Matt on the bed with his
pants and shorts off. His cock was huge and stood straight up in the
air.
I decided to tease him a little, so I crawled onto the bed and asked
him what I should do with this thing. He told me that he wanted
me to suck him and I played dumb and said that I didn't think I was
that kind of girl. He sat up and said that if I wasn't that kind of
girl, why was I back in the bedroom with him.
Hard question to argue, so I leaned forward and kissed him on
the lips. He returned my kiss and soon we were rolling on the bed,
kissing and touching each other. In the process, Matt wrestled my
panties off and started to finger me as we continued to kiss. I felt
so good to have him slide his fingers in and out of my wet cunt and
I could feel my clit getting really hard. As he licked my ear, he
whispered to me that he really wanted me to suck his cock and that
was about all the encouragement I needed. I moved to his crotch
and swallowed him whole.
As I was sucking him, I heard the bedroom door open. I froze,
with my mouth on he end of his cock and made sure my dress was
pulled down over my exposed clit. As I waited to hear something, I
felt somebody get on the bed. For a moment, I was stunned. Then I
heard Gail's voice tell me not to stop and could feel her hands move
up the backs of my legs and under my dress. She took hold of my
clit and said that I was a beautiful girl with a beautiful clit and that
she wanted to taste it. Matt's hand came down onto the back of my
head and pushed it so that I swallowed him again and I could feel
Gail slide under my dress. Before I knew it, she was sucking me as I
sucked Matt.
I came at once and Gail sucked up all of my juices. Matt was
so big and hard, I thought he was going to cum but he told Gail to
move up beside him. She lay down on the bed and Matt rolled off.
He told me that Gail really liked to be licked and would I want to
taste her pussy. I whispered yes and Gail lifted her dress and spread
her legs. I put my face back down into her crotch and found her clit
with my tongue. The moment I touched it, she let out a small cry
and said that she wanted my tongue in her cunt. I moved it in and
out and Gail thrust her hips into my face and almost smothered me.
As I worked on Gail, Matt slowly moved my dress up to expose
my ass. He lifted my hips and before I knew it, worked three of his
fingers into me. It felt so good and I moaned out loud in appreciation.
This spurred Matt on and soon he had four fingers working in and
out of my now very wet cunt. The slurping sounds only made me
hotter and I started to beg him to fuck me. Matt removed his fingers
and suddenly plunged his cock into me. The first thrust hurt like
hell, but quickly went away. The pain was replaced with an intense
pleasure as he fucked me from behind and the harder he fucked me,
the harder I licked and sucked Gail. During all of this, Matt kept
calling me a little slut and asked Gail how her cunt licker was doing.
She just moaned but didn't say much of anything else. Her clit, by
this time, was like a little cock and I could feel her body start to
tremble with her oncoming orgasm.
During all of this, my own clit hard returned to its rock hard state.
Mostly because while Matt was fucking me, he was also stroking me.
I could not keep track of the times Gail came and finally Matt lifted
me up by my breasts and started to kiss my neck. He whispered
in my ear that I should fuck Gail with my beautiful hard clit and
I started to move toward her. As I did, Matt kept his cock firmly
imbedded in my cunt. As I moved even with Gail, she waisted no
time in grabbing my clit and forcing me inside of her. As I slid into
her soaking wet cunt, Matt brought all of his weight down on us and
rammed his cock home one last time.
I think we all came at once, but I'm not sure. I'm not really
sure why I came. It was either Matt's cock or Gail's cunt or the
combination of both. All I know is that it was quite a while before
any of us moved. Matt was first off and I quickly got off of Gail and
started to organize myself as best as possible. As I was standing,
Matt sat back down on the bed and started to finger Gail. She
moaned that she wanted to be fucked again. I said that Matt was on
his own as I was still trying to recover. I left them on the bed with
Matt starting to lick Gail all over again. I'm sure they were both
part rabbit.
As I made my way to the bathroom, I met Connie and Roxanne
in the hallway. I'm sure I looked like hell, and Connie remarked that
I had better change my fishnets as they had a huge run in them.
Roxanne then asked me what I thought of Matt Gail and all I could
say was that she was very lucky to have them as roommates. Connie
was curious as to what had gone on and I told her that as soon as I
cleaned up, I would get back to her.
Once in the bathroom, I re-did my makeup and brushed out my
hair. I went to my bedroom and swapped my fishnets for a fresh pair
of nylons. As I hooked my garters on them, I kept thinking about
the events that had just transpired and vowed that I was going to
have more times with Matt and Gail.
When I was finished putting myself back together, I proceeded to
go down stairs, but stopped outside of Roxanne's room. The door
was slightly ajar and I could hear her voice inside. I pushed open the
door and found her on the bed with Connie between her legs. As I
started to turn around, Roxanne asked me to come in and watch. It
I started to live part-time on weekends at Roxanne's and worked quite
hard on perfecting my image. As I added to my clothes collection, my
sense of style grew considerably. I found I tended to gravitate more
to the flashy mode of dress and, with the help of Roxanne, Gail and
Connie, acquired some very sexy outfits. I also discovered Frederick's
Of Hollywood and a few other mail order outlets. This, combined
with a lot of TV magazines and books, helped in establishing my
look that has stayed with me for years.
When I turned sixteen, I received my first car. Freedom at last.
It wasn't anything special, an old 72 Volkswagon, but it was mine
and I could now come and go as I pleased. The first weekend I had
my drivers license, I drove over to Roxanne's and showed it off. She
was pleased that I had a car, since she was the one who normally
would have to drive me around. I decided to stay over and phoned
Connie to see what she was up to. She said that she was busy on the
Friday night but did I want to come over on the Saturday. We could
go out for a drive in my new car and maybe hit a club or two. I was
only to egar to see her and to show her my car.
I stayed over at Roxanne's and on Saturday decided to get up
early and spend the day as Anna. I had the house to myself as
everybody was out for the day to the country for a picnic and dance.
After my shower I put on my sexiest bra and pantie set, a low cut
blue silk blouse, a pair of navy pantyhose and a pair of Gail's old
jeans. They were the kind she always wore, Fancy Ass, I believe.
I had tucked my balls up into their sockets so that when I put the
jeans on and pulled them tight around my waist, I looked like I had
my own pussy lips. They felt and looked great and I slipped on a
pair of high heels with a sling back to complete my dressing.
I put on my long black wig and brushed it out. After doing my
make-up, which by this time I was getting quite good at, I put on my
earrings and was finished. I looked quite good and walked back out
to the kitchen to get a cup of coffee. About a week before, Gail and
Matt had bought a small dog. I think it was a terrier. It's name was
Kitty (You figure it out) and she was whining at the back door to go
out. Since there wasn't a fence around the yard, she had to be walked
on a leash. I didn't think much of going out in broad daylight, but
I also didn't think much of having to clean up her mess. I grabbed
her leash and off we went.
It was a very strange feeling being part of the world during the
day and I didn't think anybody really noticed me as we walked along.
I thought that I was doing okay, so we went done to the park that
was a few blocks away. As we waited at a busy intersection, a car
full of boys drove by and one of them hung his head out the window
and yelled "Hey Babe, nice Ass!"
It was a good thing I had my makeup on as he couldn't see me
blush. I smiled and waved and then walked across the street to the
park. Once in, I found it to be deserted as it was still early morning.
Then the worst happened. Kitty spotted a real Kitty and off she
went. The leash was yanked out of my hand and my stomach did
a few flips as I watched her disappear around a bush. I started to
run as best as I could in my heels and as I rounded the bush, I came
upon two boys, about 17 years old, who had stepped on the leash
and stopped Kitty. They brought her over to me and asked me if she
was my dog.
I just nodded and they handed me the leash. Then they just
stood there staring at me and smiling. I looked down and saw that
my blouse had become unbuttoned and my lacy white push-up bra
was almost fully exposed. I quickly closed my blouse and muttered
a quiet thank you. One of the boys said "No, Thank You!" and kept
on smiling. The other one asked me if I was new in the area and I
said yes. He asked me if I walked in the park often and I said no,
that his was my first time. He then commented on how good my
jeans looked on me and again I blushed. I thanked them again for
the help and one of the boys asked if I would be out for a walk later
that night. I said that it was possible as I was taking care of the dog
that day. He said that if I was, he could meet me back in the same
place around nine. I told him that I was meeting a friend, but that
we both might come over. Both he and his friend said they would
hopefully see me later.
I walked back home without much incident and once inside tele-
phoned Connie to tell her all about my morning. She laughed at me
and said that I had to stop picking up young men. We made plans
to go out that evening to a bar and I suggested we swing past the
park and make one quick stop around nine. Connie giggled and said
that I was one big tease. The rest of the day was spent relaxing and
getting things ready for that night.
After I had fixed myself a lite dinner, I called Connie and told
her to come over. She decided to bring her things with her so that
we could dress together. I had never seen Connie as her alter ego,
Neil, but had to admit that as a male, he was very good looking.
When Connie arrived, I was already half dressed. I met her at the
door in my dressing gown and had just finished putting on my black
wig again. Connie commented on how much she liked this particular
wig and I was pleased with the support.
As we finished dressing, we talked about what we were going to
do that evening. I told Connie that we really should go past the
park as I had never been with a boy my age when I was dressed. She
asked me what I wanted to do, and I said that I had a fantasy about
sucking the cock of a guy that I did not know. She said that she had
the same fantasy, so we had better make it a reality.
I could not decide what to wear, so Connie picked out my outfit.
It consisted of a dark blue silk blouse and a black wrap around skirt
that fell just below my knee. I wore my garter belt with black nylons
and a matching thong pantie. Connie had brought a black dress
with a wild slit up the side. We finished up and noticed that it was
getting close to nine, so after we had slipped on our shoes and coats,
we hoped into Connie's car and drove towards the park.
We pulled into the parking lot and parked at the far end. As
we got out, I looked around for the boys that had been there in the
afternoon, but could not see them. There were a few people out
walking and Connie said that we should go and cruse the area. I
said sure, but felt a little awkward. We were dressed for a nightclub,
not the park, but I still had a bit of a rush as I felt like a hooker
on the stroll. It was getting quite dark and about all you could hear
was the traffic in the background and the click of our heels on the
sidewalk.
At the far end of the park we turned around and started walking
back to the car. As we neared the parking lot, the two boys I had
met in the afternoon were sitting on a bench back by some trees. At
first I was startled to see somebody but calmed down when I saw
who it was. When the boys saw us they jumped up and walked over
to where we had stopped on the sidewalk. We introduced ourselves
to each other and I found out their names where Tim and Alan. Tim
was about 6 feet tall and about 170 pounds. Alan was shorter, about
my height, and weighed around 150 pounds. They both had sandy
blond hair and bluish green eyes. I had noticed that afternoon that
each of them had very good builds and Tim confirmed my observation
by telling us that they both played on the High School football team.
Tim was the quarterback and Alan was a guard.
We sat down on the bench and talked for a while. Both boys were
very curious about Connie and myself. As we talked, I watched their
eyes roam over our bodies and pay special attention to our legs. You
couldn't miss Connie's as the slit on her shirt had fallen open when
she sat down and crossed her legs. Connie had decided earlier that
she and I would be cousins when we met people, so the boys thought
that I was new in town and that Connie was visiting from another
city.
I was starting to get a little cold and suggested that we go and
warm up in the car. Connie agreed and told the boys that we could
listen to some music and talk a little more, but that we had to be
going soon as we were headed to a party. As we got to the car we
split into couples, me with Tim and Connie with Alan.
Once inside, Connie turned the car on along with some music and
we all talked a little more about ourselves. It seems that the boys
were attracted to us as Tim sat very close to me and Alan would not
take his eyes off of Connie. Connie asked them if they had girlfriends
and they both said no. I figured it was a lie, but didn't say anything.
Connie then moved closer to Alan and asked him what he would like
to have a girl do to him if he did have a girlfriend. Alan stammered
quite a bit, but couldn't quite say what he wanted. Tim, on the other
hand, knew exactly what he wanted. He had put his arm around me
and had already started to run his hand along my leg, trying to get
under my skirt.
I whispered to him that it was "THAT TIME OF MONTH", the
age old girls defence, and that my breasts were sore. Since he could
not touch either parts of my body, I told him that I would love to
compensate by other means. He looked a little shy as I moved my
hand down along his shirt and rested it in his crotch area. I was
starting to become more aggressive with what I wanted and I think
Tim was surprised. We looked at each other and then kissed as I
wrestled with his zipper. His cock was growing steadily and I had
a bit of a problem freeing it from his tight jeans. I glanced to the
front of the car and saw Connie working on Alan and decided that
she didn't need any of my help.
Once I had Tim's cock out of his pants I started to massage it up
and down. Tim was moaning in my ear and I whispered to him that
I wanted to suck him and make him cum. Tim lay back on the seat
and I brought my head down to his crotch and teased my tongue
over his the top of his hard head. I knew that he had never had
this done to him before so I wanted to take my time. As I continued
to massage his cock, I sucked each of his balls one at a time into
my mouth. I knew I was driving him crazy and that it wouldn't be
long before he came, so I moved my mouth back onto his cock and
pumped up and down. As I sucked him, I moved my free hand back
under my skirt, pulled my pantie to one side, and started to finger
myself.
I could hear Connie sucking up front and heard Alan starting to
moan as he came. Tim was still a ways off, so not to be left behind, I
inserted one finger into his anus and moved it back and forth in time
to my sucking. That was about all it took. Tim's hips started to
grind up and into my face, making me swallow his cock deeper into
my throat. Then he arched forward and let loose with a stream of
cum. I swallowed and swallowed and swallowed some more. I wasn't
sure where it was all coming from, but there was sure a lot. I was
like Tim had never cum before and I later found out that he was a
virgin when I met him.
As I came up for some air, Connie said that if I was quite fin-
ished, we had better be going. Of course, the boys wanted our phone
numbers and I told them to give me theirs so that we would have the
choice of phoning them if we wanted to. After Tim and Alan had
left, I moved to the front seat of the car and Connie said that I had
put on one hell of a show. She admitted that she was very horny and
I said that I was the same. We cooled down by giving each other a
blow job and it was the second time that night that I had a mouthful
of cum. It was not to be the last.
We cleaned up as best we could and drove to a club in town.
I had never been there put it was quite a neat place. It was also
packed. Since we arrived around 10:30, most of the crowd had already
assembled. And what a crowd!! There had to be every type of person
from every walk of life. It didn't seem to make much difference what
your sexual preference was and the dress code was "Anything Goes".
We fit in like a hand in glove and I spotted a few other TV's. There
was also a wide array of gay, dominant, slaves and you name it,
they were there. The best attire of the evening was a girl dressed in
nothing but cellophane. A very revealing outfit, if you pardon the
pun.
We fought our way to the bar and ordered our drinks. The seating
situation was next to nil but we did find a couple of spaces in a booth.
The rest of the booth was a mixed crowd. There was two guys and
four girls. I don't know if they were straight or bi or what, but it was
nice to find a place to sit down. The girl sitting next to me was Kate
about 25 years old and later I found out her nick name was Kinky
Kate. The other girls names were Sara, Kathy and Nadine. The two
guys that were with them had just sat down and didn't really know
anybody and I really don't remember their names.
We all started talking and I found out that the girls were from
Vancouver B.C. and they had come into town for a seminar. I guess
somebody had told them about this particular club and they had
wanted to see it for a while. We talked a little about the city and
what else there was to do when in town. Kate came right out and
asked me if I was TV and I said yes. She said that she had not been
sure and told both Connie and myself that we made terrific looking
girls. I asked her if she had ever come across a TV before and she
said that her boyfriend was one. I guess he dressed all of the time and
Kate and her boyfriend swapped clothes on a regular basis. What a
dream come true.
A song came on that Kate liked and she asked me to dance. It
felt kind of weird dancing with a girl while I was a girl, but in this
place nobody really noticed. I couldn't help noticing, though, how
good looking Kate was. She was about 5' 4", 110 lbs with a 22 inch
waist but her breasts had to be 40 c's. She was a tad top heavy but
the rest of her was in perfect shape.
Kate had long brown hair and very nice facial features. She was
wearing a gold lame top that tied at the front and she had on a black
lacy bra under it. The top was open quite a bit so it did not leave
much to the imagination. She also had on a tight black mini skirt
very sheer black stockings and 3 or 4 inch heels. The more I looked
at her, the more turned on I got. We danced several times over the
evening and each time we got closer together. I think the guys that
were sitting with us got the hint and left early. By the end of the
evening we danced a slow waltz together almost rubbing our bodies
raw. I'm sure she could feel my clit starting to strain under my skirt
and I was glad it was dark in the club.
The club was starting to close and Kate suggested that we all go
back to her hotel room and continue the party. Connie said sure but
the other girls said that they were tired and wanted to go to bed. As
we walked out Kate leaned over to me and said that was what she
had in mind.
We drove everybody to the hotel and walked up to the rooms.
Once in Kate's room, she asked us if we wanted a drink and went to
the bar fridge. It was the first time I had ever seen a fridge in a hotel
room and stocked with booze to boot. We all had a beer and sat
down to talk and relax. Kate asked Connie if she and I were lovers
and Connie said yes, but she wasn't possessive about me. Kate said
that she was happy to know this as she was attracted to both of us.
She said that she had always fantasied about what it would be like
to be in bed with two TV's, but had never had the nerve to tell her
boyfriend. He was "STRAIGHT" so to speak.
Connie said that she had cum to the right place and that we
should all have another drink and snuggle on the bed together. Kate
brought us another beer and we all sat down on the bed, Kate sitting
between Connie and myself. Connie told her about our young park
dates and Kate enjoyed the details. As I sat on the bed, my wrap
skirt decided to fall away at the side exposing the tops of my nylons.
Kate kept looking at my legs and said that she wished she had as
good a body as I did. I said that she had a wonderful body and that
I wished I had her breasts. Connie said that we all had good bodies
and we should quite wasting them on talk and start using them for
some action.
We started by telling each other what our fantasies were. Connie
wanted to walk the hooker stroll and get picked up by a stranger.
I wanted to have two guys at once paying special attention to me.
Kate wanted to fulfil her fantasy by watching Connie and I make love.
Both Connie and I said that since Kate's fantasy was the easiest to
do, pitter patter, let's get at her.
Kate moved to the side of the bed as Connie and I moved closer.
We started to touch each other's bodies and then Connie gave me
one of her deep french kisses. As we kissed, she gently pushed me on
my back and I knew that she was going to be the aggressor. She had
both of my hands pinned down above my head and then told Kate
to get a couple of pairs of her pantyhose. They tied my hands down
to the bed and I did feel quite helpless, and loved it.
Connie started to kiss me again, and while we kissed she opened
the front of my skirt and pulled my panties off. My clit sprang
forward and I started to moan as she stroked it with her hand. I
could see Kate out of the corner of my eye starting to work her skirt
up and watched her play with herself as she watched us. Connie, by
this time was licking and sucking my clit and I was in heaven. The
feeling was so delicious and I could not help moaning louder. The
feeling of Connie's mouth and lips on my clit combined with the fact
that I was helpless with my hands tied down got me hot as hell.
Connie invited Kate to have a taste of me and the first time down,
Kate took me deep into her throat. I lifted my head and watched as
Connie started to lick Kate's cunt while Kate swallowed me whole.
The rhythm was starting to get out of hand and Connie came back
up and told Kate that I was ready for a good fucking. She lifted my
legs up and I wrapped them around her body. I could feel her clit
probing my cunt and she slowly worked it into me, a little at a time.
Then she started to pump me, slowly at first, and then picked up the
tempo. The feeling of Connie fucking me while Kate sucked me was
to much for me to handle. I thrust my hips harder and harder back
into Connie and could feel myself starting to cum.
I let go and filled Kate's mouth with my creamy juice and at
the same time Connie came inside of me. I continued to buck back
and forth as Kate cleaned up the rest of my cum. We rested for a
moment and then Connie said that it was Kate's turn to receive some
pleasure. I was left on my back to watch Connie and Kate. Kate and
Connie 69' each other for what seemed an eternity and my clit was
starting to become very excited, again. I said that I was starting to
feel left out and Kate moved over so that her breasts were hanging
in front of my face. I sucked and gently bit each of her nipples as
Connie fingered fucked her from behind and stroked my clit at the
same time.
Kate moved further up and slowly lowered herself onto my clit
and at the same time, Connie entered Kate from the rear. It took
as a while to find the right rhythm, but we were soon working up to
another orgasm. Kate's pussy felt so wonderful and I pushed harder
and harder into her.
I could see Connie fucking her from behind and as we moved
faster, Kate groaned louder and louder. All of a sudden, I lost it and
both Kate and Connie where close seconds. Kate screamed as she
came and must have had an orgasm for a couple of minutes. Each
time either Connie or I moved it sent a whole new shock wave through
Kate's body. We slowly broke apart and I was released from my semi
bondage. We took turns going to the bathroom to freshen up and
after another beer, said good-bye. I remembered to get Kate's phone
number and Connie gave Kate hers.
As we drove home, I said to Connie that as far as I was concerned,
I had pretty well done it all. Connie smiled and said that I had not
even started and she would show me a few tricks the next weekend.
I could hardly wait. More in my next story!
I did have quite a few more adventures with Connie but actually
started to keep a low profile as Anna as I neared graduation. This was
in part due to the fact that I had a girlfriend. We had started dating
in grade eleven and continued on after high school was finished. As
most know it all kids of nineteen, we decided to get married. This
was a huge mistake as we were not ready, my wife to be moved out
of her Mothers house into my house without time in between, and I
still wanted to dress.
I hadn't told my wife about it, and after six months of wedded
bliss, we split up because of other reasons. So much for the 2.3 kids,
the dog, and the house in the suburbs. Well, we didn't have any
kids, the wife took the dog but I still had the house. Here I was, 20
years old with a mortgage and a house, in that order. I started to
work two jobs, so that I could meet the payments. I did, however,
have from Saturday afternoon until Monday morning off, so the first
weekend that I had the house to myself, I decided to dress.
It had been a while since Anna was out and around, and I spent a
few hours going through the clothes, setting the wigs, and making a
list of things that I needed. I started doing the laundry and ran out
to pick up a few things. One item that I needed was a new pair of
shoes. I looked and looked and finally found a beautiful pair of black
pumps with 4 inch heels. I rushed through the rest of my shopping
and drove home.
As I was getting out of my car, my neighbor John walked over.
We had talked a few times over the fence and I had drank a few
beers with him in his back yard. One night in particular after the
girls had gone inside, he had a little to much to drink and made a
pass at me. Nothing to serious, mind you, but I did catch his drift.
I was a little shocked and amused as John is a real mans man. You
know the type, flannel shirts, tight jeans and cowboy boots. I had
refused politely and John was a little upset that I knew his secret.
I explained to him about my feminine side and told him that as a
male, I really didn't want to be with a male. But as a female, now
that was a different story. I had promised him that we would get
together one day and I would introduce him to Anna.
That had been months ago and neither of us had mentioned it
again. Anyway, back to the story at hand. John and I talked for
a while and he was sorry to hear about my recent freedom. I said
that it was okay and that I had decided to get on with life. I also
mentioned that, if he would like, I could introduce him to Anna, now
that I had more time for myself. He became quite excited and asked
when. I showed him the shoes and said soon. Maybe tonight? He
was thrilled and said his wife and kids were at her mothers. I told
him to hang on as I hadn't done this in a while, and that I would
phone him later if everything worked out. I was going to make damn
sure it did!!!
I went into the house and started to get ready. It had been over
a year since I had last dressed, so I was a little out of touch. But
just like riding a bike, it all came back to me. After deeply douching
myself and shaving my entire body, I did my toe and fingernails,
plucked my eyebrows and finished working on my wigs. I had a few
pounds of laundry to iron and slipped on my white negligee. It felt
so wonderful to have something silky on again and I quickly ironed
through the mountain of clothes. After hanging everything up, I
made myself a drink and sat down to start on my makeup.
It took me about an hour to do my face but the results were well
worth it. I picked out my long blond wig and brushed it out and
after arraigning it in place, started the pleasurable task of picking
out my clothes. First, the under garments. I choose my pink full cup
bra, lace pantie and garter set. Next, I rolled on a pair of navy silk
stockings and remembered why I love the feeling of freshly shaved
legs. Having a few to many clothes does pose a certain problem when
choosing, but with John in mind, I picked out a black dress with a
deep v-neck and a front split. After plopping my breasts into place
and slipping on my new pumps, I stood back to survey my reflection
in the mirror. If I do say so myself, which I always do, I looked
pretty sexy. I hoped John felt the same way, as I was now getting
very aroused with the thought of being with him.
Speaking of John, here it was 8 o'clock already and I had forgot
to phone him. I looked out the side window and saw that his lights
were on so I phoned him right away. When he answered, I said that
it was Anna calling and that Michael had told me that he might be
in the mood for a date. John replied that he was always interested
in meeting new women, so what would I like to do. I told him that
I was tired of being stuck in the house and how about we go out for
a drink. John thought it was a great idea and said that he would be
over to pick me up in half an hour. I hung up the phone, finished my
drink, and started to worry about my dress, my hair, my makeup, you
know, the usual woman things before a date.I ran to the bathroom,
sprayed some perfume behind my ear, on my wrists and behind my
legs, picked out my jewelry and redid my lipstick. I checked my purse
and picked out a black trench coat to wear.
By the time 8:30 rolled around, I was a basket case, having
changed three times and finally decided on what I was originally
wearing. The doorbell rang and I opened the door slowly. John was
dressed in casual clothes and I don't think I remember him looking
so good. He stood and stared at me for what must have been 30 sec-
onds before I finally asked him if something was wrong. He said on
the contrary, everything was very right. I invited him in and walked
back up the stairs to get my coat and purse. I could feel his gaze
drilling through me, and new that by his reaction, he did find me
attractive. But I just had to ask, anyway.
He said that I looked fantastic and he never would have imagined
how well I could look like a woman. A very sexy woman, he added.
I thanked him for the compliment and as I walked past him, stopped
and kissed him on the cheek and ran my hand lightly over his crotch
area. There was a slight bulge and he commented that I moved fast.
I said that if I had my way, it would be faster. I don't think he had
expected me to be aggressive and as we walked to his car, John kept
looking at me and even opened the door for me. I guess chivalry
wasn't dead after all.
We drove over to a lounge that had a rather dark decor and I
proceeded to find a booth in the back. As I walked through, I caught
a few guys stealing glances at me and the odd smile was extended.
It felt so good to be out again and I loved every minute of it. The
attention wasn't too bad, either.John ordered us a bottle of white
wine and after the waitress had left turned and stared at me again.
Not a word, just staring. I started to feel a little uncomfortable so I
asked him how his job was going. He said that it was fine and he had
made quite a few sales that month. He worked for a large company
selling heavy duty equipment overseas.
I then asked him how things were between him and Cathy, his
wife. He confessed that their marriage life was not so hot, and he
had suggested that they split up for a while. She had taken the two
children and gone out to her mothers in Ontario for a month to visit
and think over their relationship. John said that he had already put
quite a bit of thought into the matter and didn't think it was going
to work. He travelled most of the year with his job and Cathy didn't
like it. And a few other things.
And a few other things like what, I asked. Well, John said that
he had told Cathy that he was bi-sexual and this had gone over like
a ton of bricks. They had not made love in over six months. I told
John that he had maybe mentioned this a little to late and he agreed
with me. I decided to change the subject, so I asked him if he was
pleased with me. He said that I looked, acted and even smelled like
a woman. He asked me how I did it. I took the next half hour or so
explaining about my past and how I had come to dress. In that time
we had finished our wine, so John ordered another bottle. Not that
I needed it, mind you. My head was already starting to float and I
was feeling very warm all over.
John was particularly interested in my encounters with Connie,
so I guess I did go a little much on the details. I love to flirt and I
love to talk about sex. My story had made John quite excited, and
he moved closer to me in the booth. As I continued to talk about my
adventures, I could feel John's hand start to caress my thigh. I was
getting worked up and loved the fact that he was, too. I slowly moved
my hand down to his crotch area and was in for a BIG surprise.
His cock was huge and straining against the fabric of his pants.
I whispered that he must be in pain and I was going to play nurse.
I slowly unzipped his pants and worked his cock free. The look of
pleasure on John's face was more than I could ask for. I ran my
fingernails along his shaft and purred to him that I loved the way
it felt. I then told him that I would love to go for a drive and that
maybe I could help in relieving his pressure.
He was nothing but smiles and a few minutes later we left a
half empty bottle of wine on the table and made our way to the
car.We decided to drive out of the city towards Banff. As we drove, I
again unzipped his pants, freed his cock and started to play. I know
the touch of my fingers had him groaning and as we turned off the
highway onto a side road, I rested my head in his lap and started to
lick him slowly.
We drove for about a mile and stopped. My licking had graduated
to sucking and John said that he was close to cuming. This I did
not want, as I had other plans on my mind. I stopped and lifted my
head and we kissed for a few minutes. John was a crazed man by
now, fondling any part of my body that he could touch. I then asked
him to step outside. I followed him out and proceeded to strip off
his pants and shorts.
I again sucked him and then stood up, took off my panties, pulled
up my dress and turned around facing the car. I begged him to fuck
me and moved my ass out from the car as I rested both hands on it.
I could feel John behind me, stroking my cunt and clit, and I must
admit that I was as hard as he was. I could feel the tip of his cock
against my cunt and moved slowly back into him. John was very
gentle with me, moving into my cunt an inch at a time, and then
pulling back. Each time he moved forward, I was able to take a little
more him and before to long, had all 9 inches buried deep inside of
me.
John started to move faster and I could not help but moan out
loud. It was so erotic being fucked outside with nobody else around,
that I did become quite vocal. John did the same, and between his
deliciously dirty language, the slurping sounds my cunt was making
as.
John's cock moved in and out of me, my own fingers stroking my
clit and the fact that we both had not been fucked for a while, had
us both cuming before to long. John, deep inside of me, and myself
all over the side of the car. As John withdrew his cock from me, I
could feel his cum running down the back of leg. I tried to freshen
up as best I could and we decided to drive back to his house and
continue our date in his hot tub. I'll tell you how everything turned
out in my next story.
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