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My First Time(s) by Robert
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.
My First Time(s)
by Robert
If you want to get to really know me, I have to tell you about the most
eventful 15 months of my life.
My mother's younger brother, Bruce, has a 48-foot sailboat on which he
lives year-round. The summer before my 13th birthday, I lived with him on
the boat and we got to go sailing all the time.
His girlfriend, Mary Anne, was dynamite. She was blonde and built and
really gorgeous. Mary Anne has a younger sister, Sharon, and she was even
better looking than Mary Anne. Both of them often spent the weekends on the
boat. Sharon must have been around 21 or 22 years old because she had just
graduated from college.
Bruce would often have sailing parties where there might be as many as
20 people on the boat. Sometimes they would be friends and sometimes they
would be people from his business.
At the first party they all went swimming bare-assed-naked and that
knocked my mind for a loop. I'd never seen naked people in person before and
I could not believe my eyes! I knew this had to be a dream. For the rest
of the day it just seemed like one long never-ending dream.
There were about 8 or 9 women aboard and I never knew that breasts could
be so different. I thought breasts were breasts and that all adult females
had the same. Mary Anne's breasts and Sharon's breasts were not similar at
all. Mary Anne's were like big, soft, pink, melons with flat nipples as big
as large saucers. Sharon's breasts were like softballs with nipples like
chestnuts. It didn't matter what they looked like - I loved them all!
Sharon also had a fantastic cunt. She was the only one on board that
shaved it, and is still the only shaved one I've seen in person. Her pussy
lips were sexy and pink and large and were really obvious without pubic hair.
When she stood in front of your face, you just wanted to reach up and touch
them!
They all kept telling me to join them skinny-dipping but I was too
embarrassed to take my trunks off so I went below. I was mostly embarrassed
by the fact that I was embarrassed. When it was just the four of us, Bruce,
Mary Anne, and Sharon had treated me like an equal (I was tall and strong for
my age, I'd proved myself as being a good sailor, and I even had a few public
hairs already), but this awkwardness and embarrassment made me feel like a
little child.
Sharon, already someone I considered a good friend (even if I DID have
a crush on her!), came down to see if I was okay. She tried to talk me into
joining them on deck while she sat there right next to me, as naked as could
be. I could barely breathe, and I didn't know where to look! Finally, she
dared me to race her topside. Being naked did not seem to bother her, so I
thought "what the hell!" and I beat her topside and into the water (she had
given me time to pull my shorts off).
They all remained naked all night long and later I saw all kinds of
fooling-around. Most of them treated me like I was the on-board waiter and
just ignored me being there and seeing them. I wasn't peeking, they were
everywhere and doing everything. All in one day, seeing my first naked
people and then seeing them having sex overloaded my circuits!
My quarters was the only place not being used, so I latched the door and
got into my berth. I was exhausted and a little jealous. I saw Sharon
sitting on an old guy's lap and they were both naked and laughing. I didn't
want to stay and see what was going to happen, next.
A couple of hours later, Sharon asked if she could come in, she wanted
to get away from the crowd and all the orgy-making, too. She said everybody
was after her to join in and she wasn't in the mood for a "mob scene."
She slept with me that evening, but first, she took my little penis in
her mouth. I felt it grow in her mouth and she proceeded to lick and suck
until she took her mouth away and I shot my cum all over my stomach! I
didn't even know people did such things and it was a very sudden orgasm (I
had no idea I'd spurt all over the place and then feel so accomplished making
such a mess). I immediately fell asleep.
I awoke the next morning as Sharon was kissing her way down my chest and
stomach to my penis. She took me into her mouth and stayed there until after
I came, swallowing everything. Then, she knelt over me and let her nipple
brush against my lips! I didn't know what to do and I just started sucking
on it. She smiled down at me, "MMMM..Good! I like that!" Then, she got out
of bed, kissed me on the lips and told me to help her with breakfast!
The others all teased us that morning because they knew we shared the
same cabin, but we didn't care because we were a "couple" for the rest of the
summer and I loved every moment with her. Bruce and Mary Anne were very
helpful and understanding. They didn't poke fun at either one of us and
didn't seem to mind that Sharon taught me everything. To this day, I have
no idea why a 22-year-old woman was so interested in such a young boy, but
I thank God everyday that she was!
That afternoon, after all the party people left, she clipped my
fingernails until there was nothing left of them and wouldn't tell me why,
only that I'd find out that evening. She brought a jar of petroleum jelly
to bed and told me that it was now my turn to give her head.
I had had a flaming hard-on all day and by then it was in a permanent
state of HARD. She held my head between her thighs with both hands and moved
my mouth where she wanted it to go. At first, I couldn't breath but, soon,
I learned when and how. She told me when and where to use my tongue, my
lips, when to nibble, when to suck, and when to bite lightly. I LOVED eating
her bald pussy!
I also loved her tits. Big, round, smooth, soft and firm at the same
time, I couldn't get enough of touching them. I loved feeling her nipples
get hard and pulling on both nipples at the same time and listening to her
moan.
But, when I was eating her pussy, she wanted one of my hands elsewhere.
She didn't like a finger inserted vaginally while I gave her head. After she
handed me the jar and told me to get my index finger full of it, she showed
me where to stick it - in her anus. I thought it strange, that first time,
but who was I to question her? I wasn't very good at it that first time but
I learned fast. I soon knew she wanted a second finger inserted up her ass
just before she came.
I have known a few women since Sharon, but I've never ever met one who
had such loud and awesome orgasms from eating her cunt with at least two
fingers up her ass. For the first few days, the only thing I didn't like
about giving her head was that I always shot my load into the sheets when she
came, it excited me so much.
Vaginal intercourse was wonderful! From that second night on, whenever
Sharon was on the boat, we would have sex almost as often as I wanted it
(which was almost all the time!). She would laugh at my erection and the
look on my face and say, "So soon? Okay, you little sex machine, let's go
below decks." When we were out at sea, we'd both be naked and she would just
bend over and let me stick my cock in her for a quickie - even in front of
Bruce and Mary Anne!
Our second weekend together, after I had eaten her pussy until it was
dripping wet, Sharon covered my penis with Vaseline and said, "Instead of
your fingers, tonight!"
I understood right away what she meant and pushed my erection up her
anus. Sharon moaned and I loved it, too! It was so damned tight! I didn't
last long, but it didn't matter, Sharon had a screaming orgasm soon after I
started fucking her ass. For the rest of the summer, we did anal sex almost
as much as straight fucking and oral sex. Sharon said she had a very
sensitive anus, and I had to agree!
I guess because of Sharon, I still have a real thing for older women and
anal sex. I have my own boat, now, (it can only sleep 4) and for the past
year I've seen a really dynamite red-headed woman around the marina. She
must be in her early 40's and I have an instant hard-on whenever I see her
smile. A real hard-body, her butt is gorgeous! It really is a shame she's
married. She comes by in her tiny bikini to visit and talk maybe once a
week, but I don't lead her on. I'd never get involved with a married woman
who's husband has a boat two slips over, and I don't think she really wants
it either. She just likes giving a young guy like me a hard-on. It's rather
obvious each time she does.
Also, because of Sharon and that first summer, I just love slapping the
front of my hips up against the fullness of buttocks. Vaginal intercourse
is great but can't compare, let alone compete, with it. Not in my book.
It's the ultimate pleasure for me. That may be the sole reason I'm bisexual.
Later that first summer I got to know David and Chris. They lived on
a sailboat a few slips away from Bruce. I'd noticed that both of them were
sometimes naked while aboard, even in the harbor and that really made me
curious.
By then, Bruce had already had several naked swim parties (I should call
them orgies), and even though Sharon was always there and even though I was
always with her (and loving every second), I was also interested in looking
at naked men. The women were very nice to see (every boy dies to see naked
women, and I was no different), and Sharon was always the most gorgeous, but
seeing the naked men was just as exciting and I didn't understand it (or my
feelings). Chris and David helped me understand, bless them.
I have known a few men since then, some were nice and others real
creeps, but only one has been as good as David and Chris. They were in their
mid-30's at the time. There is no doubt they knew about Bruce's sailing
parties and they must have known something sexual was happening with Sharon
and me; they saw us on the boat often enough.
Bruce and the other men were only naked when there were women aboard and
once the boat was out of the harbor. It seemed as though Chris and David
were always naked and I'm sure that drew me to them.
I found all kinds of excuses to go to their boat. They were always very
friendly, I just didn't know what to do or how to do it. I don't think I
even knew that I wanted to do anything. I was only aware of a desire to see
them (because they were naked?) and even that I tried to hide from myself.
And then one day in the middle of the week, when the marina was empty,
one was giving the other a back massage as I climbed aboard. They didn't
stop, just asked if I wanted to stay and have a seat. No way I wanted to
leave! Then David rolled Chris over and I saw Chris's raging hard-on. David
put some more lotion on his hands and began to massage the erection! My eyes
popped out, my mouth went dry, and I got a hard-on that hurt.
I'd never seen a man give another man a hand-job, and I knew I wanted
that! They laughed and said I could be next.
I don't know what they had in the bottle they were using, but as I got
on the bench seat, I heard one say to the other, "Get the baby oil for the
baby." That took the wind out of my sails a little.
They really did a number on me, both of them at the same time. I'd
never felt so many fingers do so many exciting things to me so fast. Laying
on my back, my cock harder than it had ever been before, the oil made
everything really hot. One slid one finger deep in my ass, it hurt just a
little at first but soon, like Sharon, I only wanted it more. It was all
happening so fast, like the boat was spinning faster and faster and deeper
and deeper. Just as I was about to scream my lungs inside-out, the other
slid a finger up into me also and those two fingers made me shoot my load up
in the air and all over my face. My mind went utterly blank and my whole
body died totally dead. I'd NEVER had an orgasm like that! Now, I knew why
Sharon always screamed during her orgasms!
All that summer, Sharon still gave me great head, but both Chris and
David were better. It wasn't long before I was fucking both of them and that
was really good, too. I'm not saying that fucking a guy anally is better
than fucking a girl anally, but it is more "forbidden" and that can make it
sexier. I was always afraid I'd hurt Sharon, but with David or Chris I could
really cut loose and go all-out.
What-the-hell, I was only twelve. I'd have fucked a knot-hole. You
remember how horny you were when you were that age? Admit it!
That fall I had to leave the marina and return to the real world. I
wasn't back in school long before I noticed a blond girl, Mary, in our junior
life-saving swim class. She could really swim. She was the best girl in the
butterfly and could even beat most of the boys. Some of the kids were
telling me about how she really liked me and that just made me feel like an
idiot. What was I supposed to do, just walk up to her and tell her that I
really liked her also? I'd already had plenty of experiences but they were
all with adults who took the lead. How was I supposed to treat a girl my own
age? I just felt awkward and embarrassed by the whole thing.
Within a few days I discovered that she was really very nice and she was
very easy to talk to. We had one special thing in common, she loved her
10-speed. We'd go riding for an entire day together, bringing along peanut
butter and jelly sandwiches for lunch.
Mary soon became the most important person in my life. We went every
place together. We'd go to the early evening show and it would be dark by
the time we walked home. It was only a couple blocks away so we'd walk real
slow on the way home.
It took forever but I finally worked up the nerve to kiss her. I will
never forget that evening. All the blood rushed to my head and I couldn't
even talk. My first true love!
She came to all my basketball games and she always made me feel like a
hero. She was the nicest and the prettiest girl I'd ever seen, but we never
had a chance to be really alone.
I know you think I'm going to tell you about some really randy teenage
sex, but we never went any farther than kissing. That was all I needed from
her and she from me. It really was puppy-love (hard to believe after the
summer I just had!). Our romance had a very sad ending because Mary's family
moved away in the spring and I never saw her again.
The next summer, before my 14th birthday, Bruce showed me a 21-foot
sailboat he said he would buy for me if I did the work of fixing it up. He
said he would teach me how and I said "Yes! You bet!" It really kept me
busy that summer.
I was one of the two tall guys on our basketball team and Terry was the
other. We were a team all through junior high and high school, and we became
the best of friends and stayed friends all these years. That summer, Terry
rode his bike over to the marina every day and helped me fix up the old
sailboat.
I introduced Terry to sailing that summer. He helped me get the
sailboat finished in early July and we named her "The Edge" because she
carried more sail than any boat her size should.
Terry fell hopelessly in love with sailing the first afternoon we took
her out. What a day!
I also introduced Terry to a lot more that summer! By the end of the
summer both of us had fucked both Chris and David, and we'd done everything
else together. Terry had even gone on several sailing parties with Bruce and
his many friends, and he got himself laid by a 35 year old married woman
(while her husband watched!) on his first trip out. She was his first real
fuck. Terry even had a summertime girlfriend - it was with Sharon's best
friend. She was Sharon's age, shorter and more blonde, but her tits were
much too big for the rest of her petite body. She was perfect for Terry and
he went bananas over her. He still goes nuts over big tits and I'm still
nuts for tight butts. We never dreamed women would ever go for young guys
the way they went for us that summer!
However, both of us were still virgins in another way -- which is a
polite way of saying that neither of us had ever been ass-fucked. We talked
about how we were both still virgins at one last thing. We knew Chris and
David would have LOVED reaming our young, tight little asses, but we knew the
best way to rectify the situation - with each other.
So we set sail very early on a Saturday morning for an island about a
half-day out. For lunch we had candy bars and other good nutritious stuff.
Got our rods out and fished for our dinner. There is nothing better than
fresh pan-fried fish you caught yourself less than an hour ago.
We got to the island, ate and then began a session of all-night sex.
We couldn't stop! It was a good thing we had lots of extra butter, because
we used it that evening to fuck our brains out. I have never spent such an
evening on any beach with any body. Talk about heaven on earth.
By the next morning we decided that male-male sex was better than male-
female sex because, although fucking a female is great, no female can fuck
you. With a female, you can not "take turns." With a female, as good as sex
can be, it can never be equal.
Both of us are still "practicing bisexuals," and sharing quarters (and
everything else!) on "The Edge II." We look at it as "we'll fuck anything
and anybody, anytime!"
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# Only the very best #
# EROTICA #
# from the collection of #
# J. BOSWELL #
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