Chapter 1 – The First Time
It was all my girlfriend’s fault. Before all this I was a pretty normal
guy. A little on the short side at 5’7″, I had dark red hair and pale
skin, and bright green eyes. I was an avid runner and swimmer and so had a
pretty lean cut body, which was naturally pretty smooth. My cock stands at
about 6″ hard, and pretty thick.
Like I said, pretty normal to look at, if on the attractive side. I got
decent grades in school, and went to college. I dated girls, and fucked a
lot of them. I mean a lot. By my sophomore year in college, when I
started dating the aforementioned girlfriend I had broken the 100 chick
milestone (I like to keep track). I was pretty open minded when it came to
sex, was willing to try kinky shit, it turned me on.
So then I met Gwen. She was smoking hot, short black hair, bright blue
eyes, and a banging body. We were an instant hit, and were soon getting hot
and heavy. She was amazing in bed, and really liked to play around. She
got me to play all kinds of role playing games, using costumes, and toys.
She got me to tie her up, I let her spank me and call me names. She even
let me and a buddy tag team her, which was very hot. She really kept
One night during finals we were messing around, and she was going down on
me with all of her considerable skill. My cock was rock hard and dripping,
and my body writhing from her ministrations. Her hands played with my pecs
and the ripples of my abs. I was well on the way to getting off. She
pulled off for a moment, but her hands continued the work her moth had
abandoned, and I didn’t mind. She moved further between my legs, which
were spread wide, and began licking my taint. I loved that shit, and
moaned my appreciation. She turned me over onto my hand and knees, and
continued to jerk me as she cleaned my taint. She pushed my legs wider,
spreading my legs out even more and opening me up. She got a great angle
on my taint now, wetting the whole area behind my balls.
The she did something totally new. While she continued to jerk my fat
cock, she moved her tongue lower, and she licked my ass. I gasped, and
started to pull away, but she gripped my hips and dove deep. After a
second of shock a wave of pleasure shook me, and I moaned deeply in
appreciation. I hear my girl chuckle as she ate my ass like a pro. she
soon had me cumming geysers into the sheets. She didn’t say anything after
that other than that she was glad I liked it.
The next day I could hardly get the memory of her tongue in my ass out of
my head. The next time we messed around, I asked her to do it again. I
took her by surprise, as up until then I had always let her take the lead,
and simply followed where she went with the sex. She laid me down on my
belly and spread my legs wide. She began licking my ass, and my face was
soon in the pillows moaning. Then she began thrusting her tongue inside my
ass, opening it up. I knew I should stop her there, but it felt so good.
After several minutes of this she pushed her first finger into me. I
hissed for a moment as I was penetrated for the 1st time. But, as I would
soon discover, my ass was made for this. I moaned deeply as she massaged
me, and she soon added a 2nd and third finger. She began massaging my
prostate and I soon shot my load into the sheets without touching my cock.
Assplay became a regular part of our sex time, and it evolved further. I
loved having my ass touched, played with, opened up. And the fact that it
was taboo made it even hotter. One day, as she was tonguing my ass, Gwen
told me she had a surprise for me. She told me not to look as she pulled
away from me. I heard rustling sounds, and what i thought was a belt
buckle being worked. Soon her hand returned to my ass, coated in something
very very slick. She slid the wet fluid around and inside my stretched
ass, and it tickled cuz it was cold. After a moment I felt something
larger press against me. I start to look back but she tells me I’m not
allowed to look. I obey and look straight ahead as the larger object
pushes into me. My mouth gapes open, and I brace for pain, but none comes.
Instead the deepest pleasure I had ever known (at that time anyway)
blossomed in my ass. My girl thrust the strap-on she was wearing until I
had the full 8″ of rubber cock up my ass. I moaned so deep I nearly ran
out of breath.
“Oh my god” I said. She laughed.
“You like it?”
I breathed deep. “Yes” I whispered.
“What was that?” she asked, giggling.
“Yes” I said louder.
“Yes I like that fake cock in my ass” I said, turned on by her making me
say it. Then she began to fuck me. The first thrust drove the breath from
my lungs. She pulled back and pushed forward, my ass backed up to meet her
thrusts. I couldn’t believe how much I loved the feeling. Gwen encouraged
me, telling me to take it like a good boy. I felt so dirty, and so hot.
She fucked me for about 15 minutes before I gripped the sheets and shot my
load into the bed.
After that, Gwen asked me if I was bi. I knew that if I said yes that she
wouldn’t mind, in fact she would love it. And if I felt any signs that I
was, I would have admitted it to her. But I didn’t. I was not attracted
to men. Sure, I could tell if a guy was hot, be he didn’t MAKE me hot. So
we both agreed that I was straight, but had an unusually strong erogenous
zone in my anus.
So, we continued that way, with Gwen fucking me almost as often as I fucked
her. She took on a commanding persona when she was on top, calling me her
bitch. It turned me on.
One day Gwen asked me if she could watch while a guy fucked me. She had
lots of gay friends, and said most of them wanted to get into my pants, so
it could be easily arranged. I told her no, that I wasn’t attracted to
men. She smiled at me, and said “but we both know you love to get fucked.
And take it from me, a real cock feels so much better than a fake one.”
And she leaned in close to whisper “and it will turn me on so much to see
my sexy bitch boy take it up the ass”. I hated that it turned me on when
she talked to me like that. It didn’t take much more before I relented and
Gwen didn’t fuck me for a full week before the event. Her friend Nathan
came over to her apartment and we all hung out as if it was a normal night.
Nathan was a tall guy, about 6′, and had dark hair and eyes. We didn’t
seem very gay to me, and had a lean rugby player body. I had a few drinks,
which relaxed me about the whole thing. Nathan flirted with me, and began
touching me, first on the shoulder, then the back, and my leg. We moved
into the bedroom, and Nathan sat behind me on the bed rubbing my shoulders.
Gwen came in too, but she sat in the corner on her futon to watch. Nathan
rubbed my shoulders, and it felt really good. While he rubbed my back he
unbuttoned my shirt, and slid it from my shoulders. He rubbed my bare
shoulders, the skin on skin contact making my body temperature rise. He
reached around me and undid the fly to my jeans. He pushed me forward a
bit so he could slide my jeans off, leaving me in my small blue briefs.
Nathan guided me to laying on my belly, still massaging my back and
shoulders. He moved lower, and his hands began to rub my ass cheeks. I
moaned as soon as he touched them, which brought a chuckle from his throat.
He eased me out of my briefs, leaving me laying face down on Gwen’s bed
naked. Not a position I was altogether unfamiliar with. Nathan’s
attention was almost exclusively on my ass now, much to my delight. He
spread my legs, and with a big hand on each gluteal, spread my ass cheeks
apart. I moaned as a warm, wet object pressed against my hole, and began
to squirm. After a moment I realized that Nathan was rimming me. His
tongue explored and probed my ass, wriggling its way through my tight ring.
He rimmed me for several minutes, and I heard rustling as he shed his own
clothes. Nathan then slid a pillow underneath my crotch, raising my ass
up. I next heard the click of a lube bottle, and soon I felt his slicked
up fingers probing my hole. First one, then 2, then 3 fingers slid in and
out of me. I was ready to go, moaning “please fuck me”. Nathan chuckled
again, and I saw Gwen wink at him. I felt his cock head against my hole,
it was definitely fatter than the strap-on I was used to. He eased
forward, and my mouth opened as the fat head popped in. I was waiting for
pain, but felt only wonder and pleasure. I groaned as he continued, his
fat length sliding into me, going even deeper than the 8″ dildo I was
“Oh fuck” I breathed as I felt his trim pubic hairs against my ass. I knew
I was in trouble then; it was the greatest feeling of my life. Laying
there on my belly with a long fat cock in my ass, I felt RIGHT. Nathan
stayed still a minute, giving me a chance to adjust to him. I loved the
feeling of his weight on me while he was in me to the hilt. He then pulled
back, slowly, and thrust into me. I let out a deep, primal moan, which
brought a chuckle form Nathan. He proceeded to fuck me slowly,
rhythmically. My body was electrified with pleasure, I was hardly able to
comprehend the fact that I was being fucked in the ass by a man. I had
taken a dangerous step onto a slippery slope, but my body refused to let me
I was supposed to watch my girlfriend during this, to get off on her
masturbating to the scene, but I was blinded by pleasure and lust. Nathan
fucked me continuously for half an hour, during which I experienced only
joy in its most physical form.
“You love it don’t you?” he whispered in my ear as he increased his pace.
“Yes” I answered, my breaths coming in gasps.
“Tell me what you love.”
“I love your cock up my ass.”
“You like being my little bitch bottom?”
“God yes, Nathan.”
“Call me sir when I fuck you.” A tingle went down my spine at that
“Yes sir” the words made my cock even harder, getting me even closer to
cumming. I knew Nathan was getting close too as his pace and f***e
increased. He hit that wonderful spot inside my ass repeatedly until I was
whimpering for release. A tingling sensation was all over my body, my
muscles trembling. I had yet to touch my cock.
“You gonna cum for me bottom boy?” he asked, his breath coming hard now.
“Gonna cum from me fucking you?”
“Yes sir…I’m gonna cum…right now” with that the tingling sensations
reached a fever pitch, my ass was thrusting backwards of its own accord,
driving Nathan’s cock even deeper. My vision vanished to white light as I
came without touching my cock, my load soaking the bed sheets. As I rode
wave after wave of orgasm, my ass clenched down harder on Nathan’s fat
dick, and he groaned deeply as he shot his load deep into me. I could feel
him pumping into me, my ass filling up with his essence. Somehow it made
it even hotter to take his load.
As the orgasm subsided, I felt Nathan pull out of me. He stepped into the
bathroom to clean himself off, emerging a moment later clad in tight black
boxer briefs, his still semi-hard cock bulging obscenely. I couldn’t help
staring at it, despite the fact that I was completely worn out.
“So, how was he?” Gwen asked, suddenly reminding me that she was in the
“So good girl” Nathan asked, grinning. “We are definitely going to have
fun with him.”
I staggered to my feet, and head to the bathroom. Closing the door, I lean
on the sink, still lightheaded. I look into the mirror, and I see a
flushed face, messy copper hair, and the distant looking green eyes of a
guy who just got the shit fucked out of him. Who is this guy in the
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