My Sexual Autobiography part four (conclusion)

While dating Sheryl, we had a protracted fight because she slept with her
ex-boyfriend. During our week-long disagreement, I slept with my
ex-girlfriend Jane, not to get back at Sheryl but because I'd always
wanted to do it again and Sheryl and I did not have a monogamous
relationship at the time. Jane was more sexually thirsty in bed than ever
before, something I didn't think was possible. One night I called her and
we talked dirty over the phone for about half an hour, then I told her to
come pick me up. I said, "Don't put on panties. Don't put on a bra. Don't
even put on shoes. Wear very loose-fitting jeans and come pick me up."
When she arrived, I was wearing only a pair of baggy shorts and a t-shirt.
No underwear, no shoes or socks. I got in the car and immediately kissed
her, then lowered my hand into her pants. She had shaved her pubic hair.
It was a Pavlovian reaction -- as soon as I felt the absence of pubic
hair, I got a massive erection. I let it out of my pants and she gasped as
her hand gripped its girth. We masturbated each other as she drove back to
her house. She begged me not to make her cum as she was driving because
she'd have a wreck. Her pussy was absolutely soaked with juices when we
arrived. Her pants had a huge, warm, wet spot in the crotch. My hand was
covered with it. We almost ran inside. She locked the door and I told her
to take off my clothes. When I was naked, I took her clothes off pretty
roughly and carried her to the bed. I spent a good half-hour to forty-five
minutes eating her newly shaven pussy. I loved every minute of it,
drinking deeply from her sweating thighs and her cumming pussy. She said,
"Let me suck your cock, oh God, I want to right now!" and so I presented
her with my erection. She sucked it right down, licking and slurping with
a fury, stopping only to ask me if I was ready to cum. I said yes, and she
scrambled to her hands and knees with one hand still on my erection. She
basically sat right on my hard-on and fucked herself with it. I barely had
to move as she bounced up and down on my cock. She leaned over and licked
the entire inside of my mouth with her tongue, then grabbed my head and
forced me to suck her nipples. I scratched her back and slapped her ass as
she fucked me and I sucked her breasts. It was my turn to be the
aggressor, and so I shoved her off of me and picked her up by the waist. I
got off the bed and threw her down onto the bed, face-down, feet on the
floor, and then shoved my cock into her pussy. She screamed and moaned,
grunting things like "Fuck my fucking pussy, goddammit!" and "I'm going to
fucking cum, you cocksucker!" I could feel that orgasmic swell beginning
in my balls, and I cried out loud, "I'm going to cum, goddamit, I'm
fucking cumming, where do you want my sperm?!" and she replied, "Oh, cum
in my pussy, please cum in my pussy," but I didn't want to because she
wasn't on the pill and I wasn't using a condom. (I know, I know -- STUPID,
and I have no excuse. I'm lucky nothing serious like pregnancy or disease
occurred.) I said, "I'm going to cum on your fucking tits," and she said,
"Oh yes, on my tits, and I'll lick it off my fingers, oh baby," or
something like that. So at the climactic moment I pulled out and jerked
off as she quickly rolled over and pressed her breasts together. I came
very copiously on her cleavage, and as she rubbed it in with her hands she
managed to catch some sperm on her tongue and swallow it. While still
rubbing her tiny breasts, she took my limp cock into her mouth and sucked
the rest of the cum out of it.
After this, we were exhausted. She went into the bathroom and pissed
noisily, making sure I could hear it. Back in bed, she asked me if I
wanted to suck her hairless pussy again. Before she finished her question
I was back between her strong legs, sucking for all I was worth, loving
the feel of her large, hairless pussy lips in my mouth.... savoring the
sweet taste of her pussy when I stuck my tongue deep inside of her. She
ordered me to sit up and bend over and I complied. She wet her fingers in
her pussy and stuck first one, then two, then three and finally all four
into my ass. She knelt behind me and thrust her hips against her hand as
if she was a man fucking my ass. It felt great and I moaned out loud,
masturbating while she fucked my ass with her hand. She turned me over and
continued to fingerfuck my ass while she sucked my cock. She began to
press violently against my prostate gland, causing a massive orgasm which
quickly filled her hot mouth with my sperm. She swallowed most of it and
then kissed me
deeply. We spat my come into each other's mouths and laughed.
This story about my last encounter with Jane does not have a happy ending,
but I'll spare you that. While I was dating Sheryl, I had another odd
experience. I had been flirting with another woman at work, Rachel, for a
very long time. We were very interested in each other but couldn't get
together. One night we ran into each other at an art show and she drove me
home. We sat on the couch and talked for a while, getting closer and
closer until we had our legs thrown over each other's torsos and our asses
pressed against each other. I asked her to come upstairs with me and she
agreed. To make a long story short, we ended up naked on my bed. I
discovered her pussy was shaved and immediately begged her to let me eat
it. She agreed and I spent a long time sucking gently on her shaven
crotch. That was the only sex we had, aside from a few minutes when she
played with and sucked my cock. Later she told me that a female friend of
hers was interested in having a three-way with Rachel and me. Was I
interested? You bet. Unfortunately, it never came to pass. I was very
disappointed.
After I graduated from college, I took a four-month trip to Europe where I
met a fantastic woman named Leah. Leah was a thin, petite, ex-ballet
dancer with beautifully wild reddish-brown hair and freckles. Leah was
from Canada and was in England for a convention. We got along famously and
spent the night together many times. The first night, we slept in her
friend's bed and had a nice cuddle. At that point I felt like I didn't
know her well enough to initiate any kind of sexual contact. Later that
week, we slept in another friend's apartment, sharing a bed with an
Israeli man who snored loudly throughout the night. Leah and I took
advantage of his complete oblivion to experiment with each other. I
masturbated her, relishing the hot wetness of her soft pussy, and she
masturbated me in turn. She surprised me by going under the covers to go
down on me -- one of the best blowjobs I ever received. There were many
repeats of this sort of mutual stimulation, and almost every time she
demonstrated her mastery of oral sex. Nobody had ever done that to me with
such skill and I nearly passed out a couple of times. Leah sucked me with
such vigor and sensuality ... it was obvious she really loved what she was
doing, especially when she ate my hot sperm and continued to suck long
after I had given her everything I had, when my cock was limp. Even then
she would suck and lick my cock and balls, finally crawling up to kiss me
and share the salty taste of sperm residue in her mouth. Leah was also an
incredibly sexy kisser.  When we finally fucked, it was just as fantastic
as the oral sex. Leah and I were very much into mutual foreplay, and we
spent a long time sucking each other's nipples (she had petite breasts and
lovely nipples), licking each other's bodies, and giving each other head.
She loved it when I sucked her clit and stuck my tongue deeply into her.
She was also one of the few people I've met who genuinely enjoys anal
stimulation. The first time I gently eased my fingertip into her ass while
I was licking her pussy, she moaned and raised her hips as if to invite
further exploration. Soon I was fingerfucking her ass with two fingers
while madly eating her cunt and she loved it all. We also enjoyed licking
each other's assholes -- she and I both really got off on that. When we
fucked, she was all over the place but always staring at me with a wild
grin on her face that was duplicated in her eyes. She liked to be on top
of me best -- she could really control the pace of sex.  On what was to be
our last night together, we took off our clothes and crawled into bed.
Immediately we began to fondle each other's bodies. She asked me about my
past and I told her about a lot of the things that I have written about
here. Leah was very excited by all this and told me she didn't want to
sleep, that she just wanted to fuck and fool around all night. Fine with
me. She asked me if I wanted to fuck her ass and said she'd wanted me to
for quite a while. It turned out that, while in England (and while she had
been seeing me), she had been sleeping with another man who loved having
anal sex with her. I was thrilled by her revelations and suggestions, so
of course I said yes to anal sex. I asked her if she wanted me to cum in
her ass or in her mouth, and she gave an evil little grin and said "Both."
We began by sucking each other off. I still couldn't get over the
hypnotizing experience of her hot mouth on my cock. I also couldn't get
enough of her small, soft pussy and its delicious juices. I wasn't ready
to cum in her mouth just yet, so after several minutes of 69ing I stopped
licking her pussy and instead concentrated on her ass. I really loved
licking Leah's asshole and dipping my tongue inside, and she seemed to get
off on it too. I was trying to prepare her
for anal sex but she had a surprise for me. In previous nights she had
forcefully fucked my ass with her fingers and tongue, and now she wanted
to do it again. I got on my knees and elbows and she knelt behind me.
Immediately she began to tickle my asshole with her fingers and tongue. I
was really getting off on it -to tell the truth, there are few things that
cause such sweet shivering sensations as having my asshole licked or
played with. Soon she had in one finger, then two, the whole time she was
licking my ass thoroughly. At last she had four fingers pumping rapidly in
and out of my hot, tight asshole and she was licking my cock and balls at
the same time. I was reaching back with both hands, holding her wrist,
helping her to fuck my ass. I came close to orgasm and begged her to stop.
She eased her fingers gently out of my ass and then lovingly licked my
rectum until the burning soreness subsided. I was trembling and my eyes
were rolling back into my head. Nothing sets your nervous system on fire
like having your ass fucked, so I figured it was time to return the favor.
I asked her to get on her hands and knees. She did and I knelt behind her
so I could suck her delicious ass some more. Soon she said she was really
ready and I placed my cockhead at the rosy entrance. I asked her to guide
it in at her own pace, and she did, holding my hips with one hand and my
cock with the other. I spread her ass cheeks with one hand. Very slowly,
Leah eased my cock into her burning hot asshole. We were both moaning and
grunting out loud like animals. Within minutes I was sliding in and out at
a gentle but firm pace and she was gyrating and thrusting her hips. I
reached around her waist and began to masturbate her clit as I fucked her
ass. She came in a few minutes and then asked me to change positions. I
slid my cock out as painlessly as I could and then she rolled over onto
her back. She raised her legs up to her ears (I was impressed!) and then
asked me to resume assfucking. I was happy to oblige -- I nestled my cock
into the dark niche, then slid it in easily with no pain or discomfort.
She groaned and smiled. With her ankles on my shoulders and our tongues in
each other's mouths, I fucked her until I was on the verge of coming. I
sat up and tried to take my cock out as smoothly and gently as possible,
then I exploded all over her torso. Immediately she began pawing up my
sperm in her hand and eating it, while I rubbed my sweaty face all over
her cumsoaked torso.  We relaxed for just a few minutes and then we were
at it again. I started by licking, sucking and kissing her ass and pussy
and she insisted on sucking my cock (unwashed, I'm slightly embarrassed to
say). It was easy for her to cum in my mouth again and I sucked as much of
her juice as I possibly could. Unfortunately it was difficult for me to
cum again so soon after such an intense fuck and so we had to abandon the
effort. We ended up getting about four hours sleep.
When I returned to the United States I moved to a new town where I knew
nobody except a single straight guy. I moved in with him and began the
process of finding a new sex partner. You see, despite all of my sexual
adventures, I am still unable to do the singles thing - heading out to the
bars and trying to pick up other singles interested in sex. I get very
nervous and insecure, believe it or not.
The first thing I did was meet an older guy on IRC. He was, of course,
gay. We arranged to meet at an Italian restaurant, no strings attached. To
make a long story short, I found him to be unattractive and terribly
boring. He was bald, he had a big, thick mustache, and he was hairy, so
that was three strikes against him in my book. When he took me home I
could tell that he wanted to kiss me goodnight or something, but I got
away without so much as a hug. I feel kind of bad for being such a prude,
but then again, I wasn't attracted to him at all and I certainly did not
want to encourage him. I was, however, definitely interested in having
some gay sex.
A couple of weeks after that, I was eating in a fast-food restaurant
downtown. The young black woman who took my order also came by my table to
flirt with me. Her flirting was not at all subtle but it was nonetheless
very flattering. I asked her name (it was Shauna), gave her my phone
number and asked her to call me. Later that night, she did. We arranged to
meet a few blocks from my apartment. I hung around at this dodgy sort of
street corner, waiting for her, checking my watch, getting nervous. She
showed up half an hour late but looked even better than before. She wore a
form-fitting multicolored dress that really accented her buxom, full
figure. We walked home and sat in the living room talking for a long time.
Finally we got into bed together and I was able to see
and touch her beautiful body. She was gifted with large, heavy buttocks,
breasts, belly and thighs, a sweet smile, and twinkling little brown eyes.
While we were making out, she said that I could fuck her without a condom
since she was already pregnant. "Already WHAT?" I sputtered, sitting
upright in the bed. Shauna explained that yes, she was pregnant, and that
she had dropped out of school to work at the fast-food place in order to
have enough money to raise her baby. Dropped out of school? "How old are
you?" I asked. "Fifteen," she replied. Now I was really freaked out - here
I was, a twenty-two year old man, in bed with a 
fifteen-year-old pregnant girl. She sure didn't look fifteen. Suddenly I
wasn't very horny any more. Again, this is one of those situations where I
was actually experiencing a situation
that's very similar to some people's fondest and most secret fantasies,
but somehow I just wasn't into it. I've read a lot of fantasy stories
about making love to pregnant teenage girls, and frankly I kind of like
those stories, but when faced with the reality of it, my heart just broke.
I felt sorry for her more than I wanted to have sex with her.
The next morning I woke to the sounds of my typewriter. Shauna was
hunting-and-pecking on my ancient elecric typewriter, already fully
dressed and eating a sandwich. She finished her work, kissed me, then left
my apartment. I got out of bed and read her note. Basically, it was a
message of gratitude. She was under the impression that I had not slept
with her out of respect for her, which wasn't really true. She thanked me
for seeing "the real Shauna" and not just her body, but that wasn't really
true either. The note made me feel even worse about the situation. I felt
like a nasty, lecherous, white slob. That poor girl. To this very day I
wonder what happened to her and how her baby is doing. She never did call
me again and I never called her either.
After my experiences with the gay white man from IRC and the young black
pregnant girl, I decided to place a personal ad. I won't bore you with the
details, but I did receive a single response. I agreed to meet the woman
at a local restaurant where
we talked for a very long time and found that we had quite a lot in
common. Her name was Annie and she was a social activist, volunteer, and
tae kwon do expert. In short, she was your basic bad-assed modern woman. I
was immensely attracted to her for that alone. Physically, she was a
knockout: long black hair, penetrating eyes, smooth milky skin,
large-boned, buxom, muscular. She drove me home that night and in the
parking lot I asked if I could kiss her goodnight. She seemed taken aback,
but only for a moment, then she agreed. Our goodnight kiss turned into a
very hot makeout session in her car. After half an hour of this she drove
us back to her place where yes, we did have sex. She was amazing in bed, a
very skilled practitioner of oral sex and manipulator of the prostate. Her
body was large and shapely, soft but muscular and flexible. Her breasts
and nipples were quite large. Her ass was broad and curvy. Her pubic hair
was thick on top but light and neatly trimmed around her labia and anus.
She loved to give and receive oral sex, especially in the shower. She was
a very enthusiastic sex partner.
Annie also seemed very needy. Almost immediately she told me of her many
boyfriends who had unceremoniously dumped her for one half-assed reason or
another. After a few days I discovered why: Annie was very, very annoying.
Despite her intelligence, her wit, and her open mind, she possessed a
singular ability to annoy the shit out of me. She was incredibly abrasive
and almost totally unaware of this flaw. Her roommates hated her and soon
I understood why they avoided her and why her relationships never lasted
very long. I couldn't understand it - she was virtually perfect except for
this one unforgivable, uncorrectable thing. But I didn't have the courage
or the heart to break off our new relationship.
After a month or so after our first date, she left the country for a
vacation. While Annie was gone I met a woman named Nancy online. Of
course, I had no idea what Nancy looked like. And no, we didn't meet in
any kind of sex-related chat room. But we did discover that we shared a
lot of common interests, ideas and goals, and soon I felt like the best
part of my day was getting on IRC at night to chat with Nancy. Of course I
told her all about Annie, and she seemed sympathetic. Nancy told me all
about her current boyfriend too. You've probably already foreseen the next
step here: Nancy and I exchanged photos, fell in love and decided to meet.
It's a cliche now, but at the time (around 1995) it was unheard of. 

Nancy was a student at a college in the Deep South. The first day we met,
she took me on a tour of the small college town and then we headed back to
her dorm room. We hung out and talked and laughed for the longest time,
and then suddenly I realized how much I loved her and how I was incredibly
attracted to her. I began to lightly stroke her arm, then I kissed her
hand. She closed her eyes and sighed. I raised my face to hers and asked
if I could kiss her. She opened her eyes, nodded slightly and leaned
forward slowly, lips parted, trembling. We kissed, tenderly at first, then
passionately, then roughly. Our hands roamed freely around each others'
bodies. Soon we adjourned to bed, where we undressed and made very tender
love. I explored Nancy's soft, gorgeous body very slowly and carefully.
Her upper torso was covered with freckles which excited me tremendously. I
kissed her heavy, full breasts, with their light-colored areolae and tiny
freckles. I moved down to her belly and hips, broad and soft, and gently
licked her tiny clitoris until she came sweetly into my mouth, whispering
her pleasures aloud. It was so wonderful and pleasurable, very romantic
and very exciting ... I'm shaking a little even now as I write about it. I
held her so tightly that night and the next morning. We hardly left her
bed for the whole weekend.
When I returned home I dreaded my next encounter with Annie. I knew I had
to tell her the truth, no more wishy-washy garbage. While I was waiting, I
received a postcard from Annie in which she informed me that she was
deeply in love with me and that she hoped our relationship would work out.
I felt horrible after that, absolutely horrible. But I still had to tell
her the truth. So when Annie finally did come back into town, I had seen
Nancy again three or four times. I resolved to tell Annie everything at
the first opportunity. Our first meeting was very sour and nearly
unbearable. I wanted to vanish, to escape what I knew was my real
responsibility, but I told Annie everything. I could almost see her heart
break.
Let me compress several weeks' of angst and agonizing discussions into a
few sentences. Annie met Nancy and Annie forgave me. I assured Annie that
even though 
I had fallen in love with someone else, I was still attracted to her -
which was (and is) true, though I would never, ever go out with Annie
again under any circumstances. Nancy wondered why I had ever gone out with
Annie in the first place. It was a mess, but it worked itself out, I
guess. Nancy eventually moved
in with me and we became engaged. That was almost three years ago.
There have been only a few sexual events in my life since I met Nancy that
involved someone else besides Nancy. Once, Nancy and I got drunk with some
young friends of ours. These friends were a fifteen year old boy and a
fourteen year old girl. As we drank, Nancy and I became more openly
affectionate towards each other and towards these kids. For their own
part, these kids were all over each other. When the boy got the girl
mostly undressed, the girl started weeping and saying that she didn't want
to cheat on her boyfriend (who was definitely not around at the time).
Nancy and I reassured her and told them they could spend the night in
separate rooms if they wanted. The two of us went to bed and left the two
of them in the living room, alone, talking, with all the lights on.
About an hour later the two kids came into our bedroom. They jumped on us
in bed - the boy starting groping Nancy and the girl started playing with
my penis. Nancy and I were confused at first. When I realized what was
happening, I went along with it, making out with the young girl, kissing
my beautiful Nancy, and feeling up the boy. Nancy wasn't as enthusiastic
at first but ended up enjoying the kisses and touches of both the boy and
the girl. There wasn't any actual sex, but it was nonetheless a very
exciting experience (and technically illegal). The boy was of Middle
Eastern descent and had a heavy frame. His hair was dark and curly, his
eyes were pools of dark brown, and his skin was dark olive and rather
hairy. The girl was a short, stocky, busty Caucasian, with thick legs and
a cute little belly. She had very long, frizzy hair that she kept pulled
back in a very attractive ponytail. I found them both to be very
attractive.
The next morning, the boy got up early to go to his part-time job, leaving
Nancy and I in bed with the girl. We touched her as she slept, then got so
excited that we had to fuck. And we did, right next to the sleeping girl.
I laid on top of Nancy and fucked her hard, kissing her roughly, while
Nancy made plenty of noise,
clawed my back and grabbed my ass. We're sure that the girl was probably
awake but too embarrassed to open her eyes, speak, roll over or anything.
When we finished fucking, we cuddled together and went back to sleep. A
few hours later we woke up to find the girl preparing to leave. She acted
as if nothing at all had happened, and continues to behave that way to
this very day. Disappointing, really, since Nancy and I would both love to
have this young woman in our bed again.
The young boy did come into our bed one more time. This time I was a bit
bolder I reached into his boxer shorts and seized his very hot, very hard
little cock and jacked him off. He responded by moving under the covers
and actually sucking my cock. Nancy and I kissed and cuddled while this
boy sucked my penis, it was a fabulous experience. I didn't have an orgasm
but it was thrilling nonetheless. Nancy and I then made love while the boy
watched, then the three of us went to sleep together.
At one point Nancy and I obtained a male Labrador retriever puppy with the
express purpose of training it to have sex with us when it was an adult.
Unfortunately, Nancy ended up being severely allergic to dogs, a fact that
neither of us were aware of beforehand. Too bad, because I have fantasized
about sex with dogs since I experienced it years ago.
To bring this extremely long narrative completely up to date, I should
tell you about another heterosexual couple that Nancy and I are friends
with. We fantasize about seducing them. The man is tall, thin, and seems
to have very little bodily hair. The woman is also tall, large-boned and
chubby, with very large breasts, thick hips and thighs, and lovely, long
brown hair. They're both quite cute and we would love to fuck them, though
nothing has happened yet. Just the other day they called us and wanted to
go out to dinner with Nancy and me. When they arrived at our door, I
greeted them completely nude, mostly as a joke but also to gauge their
reaction. They seemed a little embarrassed but also a little interested. I
saw both of them glancing (even staring!) at my cock. Everyone played it
off as a big joke, but I think I got to them. I'll be sure to tell you all
what happens ... if anything does.

