Surprises After Waking Up in A Strange Bed
By DerekGuy 17
This story series
includes depictions of gay sex and references to heterosexual sex. If
that’s not your thing or if it is illegal for you to read this story,
then stop. This story is completely made up and does not depict
Comments, suggestions, and helpful feedback are welcome - e-mail me
Surprises When Waking Up in a Strange Bed
smile crept across my face. I couldn’t help it. Every time I woke up in
a strange bed with a beautiful girl lying naked next to me, I couldn’t
help but smile. It didn’t happen all the time, mind you. I’m not a
gigolo or a drunk. But lately, I’d been going to more parties, getting
wasted more often, and waking up next to some real knockouts.
Okay, there had been the dog or two. When discovering I had been with a
total beer goggles fuck, I’d beat a hasty retreat and hoped I used a
fake name. But my inhibitions seemed to disappear when I got drunk. I
was a different guy – assertive, dominant, confident, arrogant,
manipulative. Not that I never got pussy when I was sober. I just
usually let the girl make the first move and I tried hard not to hurt
people’s feelings. When I smashed, I always got laid.
I stayed still while I looked around the unfamiliar bedroom. Usually I
woke up in a dorm room. Sometimes it was a small apartment or a teenage
girl’s bedroom at home. But this appeared to be her parent’s master
bedroom. And a very nice one at that. Lots of space and lots of light,
even with the blinds were closed. What time was it? 6:35 am the digital
alarm clock announced from the dresser. I then noticed the condom
wrappers torn open and a few unopened ones. At least I played it safe,
I sighed. That hadn’t always been the case.
I couldn’t remember a thing. Wait, I was at a party. Jerry Stahl’s
party. Jerry was a buddy from high school. He was equally bored being
back home over winter break, so he threw a get together for all of the
old gang and it grew from there. There were former classmates, some
high school students, and random others milling about. My brother JJ
was there too. Hard to believe he was a junior in high school now.
Sprawling parties like Jerry’s didn’t require an invite, just the
address. Apparently JJ thought he was ready for the big time. Right.
Who was she? I wondered, admiring the stranger next to me. She looked
young, but what can you tell from a back? I hoped she was 18, but it
was too late to worry about that now. She had long straight dark hair
and smooth skin. Unless I sat up, that was all I could see. I didn’t
want to move because I didn’t want to wake her. When she woke up, we'd
have to talk. And I wasn’t ready for the morning after chitchat that
would be required.
She was lying naked, turned away from me with the sheet covering her up
to the midsection. It was hard to conclusively say, but she appeared to
be flat-chested. That’s okay. I wasn’t so particularly about my
one-night stands having great bodies. Since I didn’t remember the
fucking anyway, it seemed to be of little consequence.
I reached my right hand down and felt for the captain. I was completely
naked under the sheets and my cock, or captain cock as I sometimes
referred to it – only to myself – was hard and feeling fine. It had
some sort of heavy workout last night. I started to rub myself. It
probably wasn’t cool to jack off in this strange bed with a girl right
next to me, but who knew what she’d be in the mood for when she awoke.
I was ready for more.
That felt good. I loved to masturbate. Not as much as I love to fuck,
of course, but given my general shyness around women, I had to learn to
appreciate some self-pleasure. College had been better for me socially
than I thought it would be. Midway through my junior year, I had
enjoyed the company of a handful of girls for short relationships, and
a dozen or even more from drunk, one-night stands. While I rarely
engaged in too much banter the next morning – the girls were usually
embarrassed and we both spent a lot of time pretending we remembered
anything – I did learn one surprising thing about myself when I was a
drunk fuck. Sure, the boldness I displayed in approaching drunk girls,
get them back to their room (never to mine), and having sex was
impressive enough. But that was the liquor elevating some hidden part
of me. What surprised me most was to learn that after I fucked the
girl, I usually went in for a second time up the Hershey Highway. Or so
I was informed by several of my drunken conquests. I had never fucked
in the girl in the ass without significant inebriation – and therefore
I had no memory of ever doing it. I never had the courage to try it
with a girl under other circumstances.
Hmmm. I picked up the sheet a little. The light came through the white
fabric and accentuated the shapely butt of this woman…girl. She was
probably 17, I figured, living at home and in high school. Where were
her mom and dad? Wait, I was distracting myself. She had a nice ass.
How could I tell if I had fucked her there? Clearly we had done quite a
bit. I looked again at the condom wrappers although no used condoms
were in sight.
Fuck, I was horny, as my morning wood had hardened with the combination
of my strokes and my thoughts. Shocking myself, I suddenly reached out
my hand and gently caressed her butt. No response, but it felt nice. I
stroked it again. It’d be nice to know what fucking her from behind
felt like, instead of just being told about it by the girl when we
pieced together the evening.
That felt weird. As my hand moved more towards her butt crack, caught
my attention. There was some sorts of flaky stuff by her butt. I pulled
my hand back, but examined a piece that had come off on my finger. Dry,
colorless, I knew what this was – it’s dry cum. Any guy would recognize
it from his own bed sheets by the time he is 14. Well, if I was looking
for a sign, here it was. Not only did this determine that I did fuck
her in the ass, but I had done it condomless, it seemed. Or at least
shot off that way.
She shifted position a little and let out a small sound, almost like a
moan. I realized my hand had unconsciously returned to her ass and was
“I like that,” she whispered as her first words of the morning and
moaned a little again. She continued facing away from me as I brought
both hands onto her ass and then began to move up her hips towards her
“No,” she cautioned. “I want you to touch my butt. And maybe, do what do you did last night again.”
All right! I said internally in my best Quagmire voice. Finally, a
chance to fuck a girl backdoor and remember it! She rolled onto her
stomach, her head turned away from me. “Please, do it,” she whispered.
I wasn’t exactly sure of the specific mechanics. In porn, the girl was
usually on her hands and knees for this, but I knew you could do it
from most any position, especially if she wasn’t a virgin down there.
And she wasn’t.
Fuck it, I thought. For once, just go for it. You can walk away just as
easily in 30 minutes as you can right now. This is your best invite
I lifted my body up from the mattress and climbed on top of her. My
cock was throbbing. It was leading the way. I began to grind myself
into her, my dick pressing against her butt cheeks, one of my hands
stroking her hair as she pushed her face into the pillow. It didn’t
occur to me in the moment to grab a condom.
I really needed a cup of coffee to think straight, but I needed more to
fuck her now. I used one hand to grab her ass and pull a cheek aside,
and the other to help guide my dick towards a hole that I assumed would
be there. I pushed without success. So I used my other hand to probe a
little. I remembered one girl last year who had done some ass play
while blowing me. It had felt nice. So I pretended that’s what I was
doing while I really just wanted to find out where my dick goes.
There it is. Stopping the pretend foreplay, I guided the captain into
the tight hole. It went it without too much struggle. Holy shit! This
was so tight. Bareback, like last night I assumed, I pushed into her
and began to fuck.
She moaned again and then again. “Yes….” She said dreamily. This girl
was a dynamo. We must have fucked a couple times last night and the ass
fucking too. Wow, I had done pretty well last night.
This was great. Not like fucking a pussy at all. Tighter, less natural,
but feeling so amazing. My hips got into sync and strokes were even and
“Faster,” she whispered. I complied pushing into her with speed and
energy, especially for 6:30 in the morning. This was the first time I
would remember back door sex. It was also the first time I had ever
fucked a girl without knowing her name – at least that I’d remember.
Oh, here it comes. I felt my balls tighten, my breath change. What was
the etiquette? Do I cum inside her? On her? Uhhh…too late now. Grinding
my groin against her ass, I let go with a few unintended grunts. She
was moaning a bit more too. Four shots in, I seemed to be done. I lay
there for a moment, kissed her shoulder and neck, and then rolled onto
Catching my breath, I knew I had to piss. I mean, I did every morning
when I woke up, I just had pushed it aside to fuck. I scanned the room
and saw the obvious bathroom door.
“Just going to the bathroom,” I whispered, so she wouldn’t think I was running out.
The bathroom was big with a sunken tub and giant mirrors. I looked at
myself after I flushed the toilet. 5’ 10”, 165 lbs., brown hair, hazel
eyes that were currently bloodshot. My hair always looked ridiculous in
the morning before a shower, but I used a brush on the sink to give it
some help. I had let my sideburns grown a little too long too.
My body was looking decent. Ultimate Frisbee three times a week had
helped keep me skinny and toned, since I didn’t work out much or play
any other sport regularly. I was the foosball champion of my dorm
building. I needed to add some more muscle. The mass consumption of
beer didn’t help either, but that was mostly weekends. I washed my
face. My cock was surprisingly still half-hard. I grabbed a couple
tissues, wet them, and cleaned the captain off. An ex-girlfriend had
named it the captain. She hadn’t seen a circumcised cock up close
before me and found the big exposed head looked like a captain’s hat on
a ship. I thought she was a fucking moron, but since she gave great
head, I didn’t care. Somehow in my own mind, the name had stuck. I had
never said it out loud to a soul
With a freshly clean cock and face, I came back in the bedroom. She was
in the same position – lying on her stomach, face into the pillow. But
she had pulled sheet up to her shoulders. I crawled back into bed next
to her, lying on my back. I still really needed coffee. The ceiling had
two skylights, I noticed. I had never seen that before. The whole room
had an off-kilter style to it – clearly someone with a sense of design
that I’d never understand and with a fair amount of cash too. Well, I
didn’t come from a family that could afford to add skylights to our
modest ranch house. The paintings on these walls were also very modern
– abstract geometric shapes. I thought they looked like the work of my
Then everything changed. Two hands had grabbed my dick and I felt the
warm, wonderful feeling of a mouth engulfing my not quite flaccid
member. While I had been reflecting on the room, she had crawled under
the sheets. Only her left foot was partially visible, the rest covered
by the white cotton blend.
“Oh!” I couldn’t help but cry. She knew what the fuck she was doing,
that’s for sure, as her teeth nibbled a little on my cockhead. My dick
was approaching full hardness. I was usually good for several times in
a row – I didn’t last long, I knew, but I could do a lot of successive
Her tongue was like a snake’s, sliding up and down the shaft, across
the head, around the balls. I reached a hand under the sheet to touch
her hair or breasts, but she stopped and whispered, “Just lean back and
enjoy.” She sure whispered a lot. Maybe there was someone else in the
I put my hands behind my head and simply enjoyed. There were few things
better than an early morning, guilt-free blowjob. Would I now have to
stay for breakfast if she wanted me to? If someone else was home, I’d
be able to leave right away. Cut the cord quickly, I had learned, was
the best policy after a one-nighter.
She was taking the whole thing in now. Not quite deep throating, but
leaving little of the captain unconsumed. She was using one of her
hands to play with my balls and ass, while the other held my dick
steady and occasionally jacked me while she worked on the head. She was
fucking unbelievable. This was a great blowjob.
“I’m almost there,” I warned her much too soon for my liking. It was up
to her what the next step was – did she want to swallow or spit? Should
I cover her face? Would my orgasm result directly from her mouth, her
hand, or from my stroking and in the end? I really couldn’t be pushy,
but, delightfully, she had only increased her pace, stroking my shaft
with abandon while engulfing the head with her mouth. The waves of
pleasure made my body tremble repeatedly.
“It’s…” I decided to shut up and let the ejaculation go. She knew it
was imminent. She slowed her stroke slightly and my hips bucked again
as my cum shot into her mouth. Damn, I thought, I wish I cold have seen
that. That’s the only thing that would have improved that suck job – if
I had been able to see her face the whole time. As I shot the last bit,
she paused a moment, and while continuing to gently stroke very
sensitive captain, she licked my now super-sensitive head clean.
My breathing calmed. I prayed she was good looking. This was a girl
that was worth knowing and revisiting. Just my luck she would be either
a slutty 14-year-old or some hideous hag. At least I know she wasn’t
old or fat. Hey, call me a pig, but this isn’t a girlfriend I had down
there, just a hook-up.
She shifted under the sheets. I hoped I hadn’t eaten her out last
night. I hated going down on a girl. I know it makes me a hypocrite,
but it is just not a taste my tongue wants to enjoy. Previous one-night
stands hadn’t reported that, though. I didn’t think I could reciprocate
this morning, if I had.
As she moved through the sheet, I let my hands rub against her body.
Face, neck, chest. Wow, she was flat. Oh, God, not a 13-year-old! And
just as her head emerged, my hands encountered something else.
Something that shouldn’t have been there. Something that changed
She wasn’t 13. Maybe 17 by the looks of it. The teenager had a pleasant
face, big brown eyes, and surprisingly soft, long dark hair. And a
penis. She wasn’t a she. The teenage boy looked relaxed and calm. She
was a he.
“Morning!” he smiled, speaking in a normal voice as he settled onto his side.
How the fuck did I end up in bed with a guy? I had never done anything like that, sober or piss drunk. I had never imagined it.
“Uhhhh….” Was the best I could reply.
“Last night was something special,” he continued. “You were the hottest guy at the party. To end up in bed with you is awesome.”
“Uhhhh…” continued to be my witty repartee. Okay, stay calm. For now, I
just had to handle this like waking up next to a really ugly girl. Find
a nice, logical excuse to have to leave, don’t use your name, don’t
offer any personal identification, and get out. He’s not a
transvestite, just a regular teenage boy. You deal with it later.
“Don’t worry. This is just a post-party hookup. There’s no obligation
here,” he tried to reassure me, not hitting the real issue that was
causing me concern. I shifted in the bed, ready to whip on my clothes
and bolt for the door. “I’ll get up and make breakfast, Greg,” he
My autopilot response began to come out, how I was too busy to stay for
breakfast, But my mind stopped me before my mouth began. I suddenly
realized what he said. He had said Greg. Greg. That’s my name. My real
name. I hadn’t ever used my real name while drunk before, although
sometimes the one-nighter was with someone who knew me already. But
when it was a stranger, I always gave a fake name, no matter how drunk
I had been in the past.
“I know we both have a lot to do today,” he added. “You’ve got that wedding tonight.”
Holy fuck. How much had I told this guy? Did I know him? He didn’t look
familiar. “And you’re meeting JJ at the mall to help him buy a dress
shirt. You brother sounds a little self-absorbed, but you’re a good
older brother. I know the two of you don’t seem to get along, but maybe
something will happen that will bring you closer together.”
Did I go point-by-point over my life with him while we fucke…Oh crap. I
fucked a guy. Twice. Maybe more. And he just blew me. Fuck. Fuck. Fuck.
I also thought about what he said. I hadn’t really made plans to meet
JJ. Why would I? We weren’t close. Well, not since I was about his age.
But Mom had insisted I help him get ready for our 25-year-old cousin’s
wedding and I had reluctantly been coerced since JJ could use some
fashion upgrades. I was lots of things, but disobedient to my Mom
wasn’t one of them. Since our Dad died five years ago, she had
shouldered the burden for the whole family. It was also since our
father’s death that JJ and I began to fight much of the time. Most
people assumed it was a reaction to Dad’s death that we grew apart. But
it wasn’t really.
JJ would follow me everywhere when I was in High School. When I was 15,
I had my first girlfriend – she asked me out – and I spent lots of time
with her. I didn’t have much time to play video games and wrestle with
my 10-year-old brother. JJ grew resentful of all the girls I dated –
even messing up a couple relationships. I handled it all poorly and
began to punch him and ignore him and make him cry. I was a bit of a
jerk then, but I had my reasons. Our Dad had died right around then. I
also began to start drinking to help cope with my pain. The drinking
led to fooling around and later fucking girls at parties, so I kept
doing it. Mostly on weekends and that hadn’t changed in college. Now,
as JJ was a junior in High School and having his own relationships, Mom
thought we’d be able to come together again. So, I agreed to help him
get ready for Cousin Sheila’s wedding..
“Trevor,” the teenage boy said, snapping me out of my thoughts.
“What?” I answered uncomprehendingly.
“You looked a little lost, so I wanted to help you out with my name.
You were pretty smashed last night. I was too, but it looks like I
remember more than you do.”
I must have been drunk out of my mind to go home with a guy. Had some
slipped me a roofie? Had I done drugs? How much did I drink. I really
only had my usual post-fuck drinking binge hangover, nothing more.
“I know you have to leave soon, Greg,” he repeated, “but I thought, maybe we could do one more thing before you go.”
I was confused. What the fuck did this cocksucker mean?
“’Cause you’ve had some more fun this morning. Twice. And I loved it.
But I need things too. And last night, you were a repeat performer and
so was I. Come on, just one more time,” Trevor’s warm hands were
rubbing my paralyzed body. He whispered loudly, “I want to be inside
Oh, shit. That’s what he means? No way. Whatever happened last night
will remain a mystery to me that I’ll forever lock up and repress. I
let him fuck me last night? What the hell did I drink?
“Oh, I know what it is. You are worried people will learn about it. I
won’t tell anyone,” he added. “I mean, you’re reputation wouldn’t go so
well if people knew you had wild drunken sex with a teenage boy.”
That didn’t reassure me. How old was he? 18? 15? Was he making a threat?
“Just one last thing and then you can both pretend that this all never
happened. I’ll be quiet as a mouse. Won’t brag at all. If we do it now,
this underage teenager will shut up forever.” Yes, it was a threat.
Trevor’s hand had begun to caress my leg. I was still frozen in
indecision and confusion. “Wait a sec,” I finally blurted out pushing
his hand off.
Okay, calm. Stay calm, Gregory, or you won’t think clearly. Let’s
review what things we know for sure. I went to Jerry’s party last
night. I saw lots of old friends. There were a whole bunch of high
school students there. Jerry’s sister is the same age as my brother JJ,
which is why probably the reason JJ and the other students were there
in larger numbers. Some of those high school girls were hot, I had
noted. I started doing shots, as I usually did when they were free. And
then…that’s it. That’s all I remember.
What about this morning? My pre-law classes helped me to organize my
mind. I am in what appears to be Trevor’s parents’ bedroom. I woke up
naked next to Trevor and he was naked too. There are several ripped
condom wrappers. Trevor also had what appeared to be dry cum on his
butt cheek. I fucked him bareback this morning. Then he sucked me – and
did it quite well. I never saw his face all that time…well, of course.
He must have known I would freak out and wanted to keep his identity
hidden. But why would he assume I would freak out if we had sex last
night? Because I was drunk then and he knows I am straight. Now, Trevor
is saying he wants to fuck me as he did last night. Or at least I think
that’s what he is saying.
“Pass me a condom,” Trevor assertively demanded. I reflexively
complied, letting him call the shots as I usually did with girls. A
bottle of lube had appeared from somewhere. Any assertiveness from me
from the booze had totally vanished.
“Turn over, Greg.” I did so, not sure what I was doing.
Trevor’s warm hands began to massage my butt, pressing between the
cheeks. Soon the lube was being applied both directly and via his
hands. This didn’t feel familiar, but I could never remember what
happened when I woke up the next morning. One thing was for sure, I’m
not getting blitzed like this again unless I have someone watching out
for me. I needed a fucking wingman.
“Fuck!” I cried as Trevor inserted one of his fingers in my hole.
“Don’t fight it! You need to relax. You need to be calm. You can enjoy this.”
I said nothing. Was I going through with this? If not, what was I
waiting for? I suppose I had always been curious. Fucking a girl in the
ass was a feeling I wanted to try and remember and I had now…although
it turned out to be a boy that I fucked. Getting fucked myself wasn’t
something I had really considered. But gay guys seemed to like it. And
girls seemed to like it. So maybe I would too.
Not that I had much choice. I was terrible at confrontation. Sometimes,
after a night of drunken sex, I would sneak out of the girl’s room
without waking her. But today I’d have to face some consequences. This
high school kid could spread the god’s honest truth all over town and
kill my reputation. Was there statutory rape for gay sex? Probably. I’m
screwed, so I need to get fucked.
“Fuck!” I cried. He was up to two fingers. Then he reached around with
his other hand and gently began to stroke my dick. The third finger was
tough, but I grunted my complaints more quietly.
Trevor then let go of my dick and pulled his fingers out of my ass. I
heard the familiar rip and peered over at the boy putting on the
condom. His dick wasn’t big, I was grateful to see – not that I really
have much experience in judging dick size. It was uncircumcised. But it
was definitely a bit smaller and skinnier than mine. More like two
“Get on your hands and knees,” he stated with supreme confidence.
Was that the best position? How the fuck should I know. But I got up on
my hands and knees anyway without responding or thinking. He moved over
on the bed, his dick hard and wrapped in the condom. Then Trevor
lowered himself into my ass.
“Fuck Fuck Fuck Fuck Fuck!” I wasn’t prepared for that. Wow, that
hurts. Like a really painful dump. But Trevor paid no attention to me
and started his thrusting.
“Relax,” he cooed. “Relax. It’ll be much better that way. I promise
you, you’ll like it much more if you let yourself and your muscles
relax.” I tried. But with a dick pummeling your asshole, I found that
to be a little challenging.
I didn’t have a real issue with pain. Friends told me I should work out
more because I could work through pain. Junior year of high school, I
had broken my arm smashing into a fence in right field – and making the
catch to save the inning, I might add. I played another four innings
through the pain, even getting a single, before we realized it had
And this was pain. It sure as hell didn’t feel like anything I had ever
done before, but the pain had begun to slightly lessen. Trevor’s hands
were wrapped around my hips and he thrusted over and over and over. How
long does this take? I kept trying to put my mind somewhere else. I
imagined being on the beach in Florida like last year’s spring break. I
thought of the lakehouse we went to when I was a kid, back when Dad was
alive and JJ and I got along. I thought of Dawn Connors, the
unbelievably hot sophomore that I was in love with at college – and who
was dating my frat buddy Mitch, much to my regret.
It didn’t work. My mind wasn’t strong enough to separate from the 16 or
17-year-old that was ramming his cock into my ass. Did this make me
gay? No, wait, gay is a state of being, Charlie had once told me in
psychology class, not an action. One can do “gay” things, but you can’t
become gay. You are or you aren’t. I wasn’t. I didn’t like boys and I
didn’t find this sexy. I didn’t begrudge Charlie, or any guy, his life
at all. What did I care who he fucked? But I guess this was one of
those gay “experiments” that so many boys supposedly try out. I was
ready for this trial to be over.
Trevor was grunting, which I took as a sign he was almost done. My
right hand, I suddenly realized, was on my own cock, gently rubbing it.
I had an erection. Shit. Well, I mean, now that the pain had subsided a
little more, this isn’t terrible. Not that I was enjoying it, but my
body was having certain unconscious reactions to the stimulation. I
mean it kind of felt okay in a weird sort of way.
“Yeah!” Trevor shouted as his body shook. Since he was thankfully
wearing a condom, I didn’t really feel much as he came. But he was
certainly happy and loud in his shouts.
When he pulled out, I fell face first into my pillow, sweat lightly glistening my body, my erection still there.
“What’d you think?” Trevor quizzed me.
“I don’t know,” I truthfully shared.
“Well, anytime you want to try again, let me know. Top or bottom.”
“Okay,” I dismissed him, although having a mouth and ass to fuck freely
might come in handy now and again. Wait, what was I thinking?
Trevor sat on the edge of the bed pulling on his underwear. “You better
go meet JJ. He’s probably done by…” He let the sentence trail away.
Yeah, I better go. Quickly. What did he say? Wait, how would he know
where JJ was or what he was doing unless…Then a memory flashed in. Mom
and I were on the phone a few weeks before winter break. She had been
pushing me to spend time with JJ while I got home.
“You know he still idolizes you,” she had said. “And if you don’t do
anything with him, he’ll sit around for the whole break with his friend
Trevor playing video games or trying to hook up with girls. And I don’t
think Trevor is such a good influence on JJ. He encourages JJ to do
Holy shit, this was JJ’s new friend Trevor. Wait a minute… I know
something else about Trevor. It was almost coming clear in my foggy
hangover mind. What had Mom told me? He’s a junior like JJ. And
his…what was it…think Greg!
I got it. I had asked Mom who the fuck was Trevor (except I would never
curse to my Mom). She had said, “You know his sister, Jennifer.
Jennifer Monroe. She’s a year younger than you. Also not of the highest
moral caliber, if I can be a bit catty. Trevor was away at boarding
school – one of those schools for kids with issues. His parents have
tons of money. Well, JJ and Trevor have become the best of friends ever
since Trevor got back to town this September.”
Jennifer Monroe. She was a bit of a slut in High School, although I
never partook. In fact, I never really even spoke to her. And
then…another memory suddenly crystallized. I was at Jerry’s party last
night, tossing back shots, and Jennifer was there too. She was likewise
getting drunk and we were talking and then we were kissing and…
I jumped out of the bed. “I wasn’t with you last night. I was with your sister.”
Trevor had been pulling on his clothes.
“Yeah, that’s true…” he agreed without hesitation.
“You fucking faggot,” I shouted. “You told me we had sex!”
“No, I didn’t,” he said quickly but calmly. “I said I wanted you to do
what you did last night. I didn’t say you did it with me. Well, you
fucked Jennifer in the ass last night and she blew you.”
“You said that last night was something special!” I angrily countered.
“Yeah, and it was. For you and Jennifer. For me too. And I never said
you got fucked. I just said we should do one more thing. I never said
you had already done it. Of course, now you have.” He was balancing his
argument of a razor blade point of the truth. He should be the lawyer.
“I’m going to fucking beat the snot of out you,” I grunted as I pulled on my jeans.
“Just wait. Wait. Wait. Give me a second to explain,” Trevor was maybe
110 pounds and had no muscle on him at all. He began backing up towards
the door as I struggled to get my other leg in the pants even as I
“Where is Jennifer?” I barked.
“Okay. Just calm down and I’ll tell you. So you and my sister hit it
off at the party. She always had a little thing for you,” Trevor spoke
quickly but calmly. “And you both wanted to fuck, but neither of you
could even begin to drive. So JJ said we should drive your car to my
house ‘cause my parents are out of town and your mom is home. When you
got here, you drank some more and the two of you began to fuck like
animals. It was amazing. We couldn’t help but stand there and watch.
You were so lost into each other you didn’t notice us…or the video
That put a pause in my step.
“Yeah, well after you two passed out – I mean, you are impressive,
Greg. You fucked her. Then she blew you. Then you fucked her in the
ass. Given how drunk you were, I was shocked you could get it up once,
let alone three times in a row. Anyway, you both finally passed out and
that’s when JJ suggested we have a little experiment. Something about
making things even with you. I didn’t care, ‘cause I saw a chance to
have some fun. So we moved Jennifer down to her room and JJ got in bed
with her. And I stayed up here. And since we knew you’d both never
remember anything, JJ and I decided to see how far we could take it
this morning. We wouldn’t lie, but we wouldn’t tell all and we’d see
what happened. But you had to do everything willingly.”
“Where’s JJ?” I was still trying to absorb this information.
“If he has had any success, he’s continuing to fuck my sister.” Trevor
seemed to find this somewhat uninteresting. Then again, I knew at least
a half dozen guys off the top of my head that had fucked Jennifer in
High School, so maybe it was rather routine.
“But, you had cum on your ass,” I offered my final argument for Trevor’s duplicity.
“Sure. But it wasn’t yours. I mean, JJ and I got pretty charged up after watching you and Jen together.”
Damn, my brother was queer or bi or something. Well, I was in a crummy
place to judge right this second. Do I beat this punk teen up? With my
height and weight advantage, plus my anger, I could really hurt him if
I wanted to. But would it make me feel any better? I had
done everything willingly. I could
have walked away at any time. And the sex this morning had mostly felt good.
“Open up, you turd!” we heard a woman’s voice shout from the hallway as the locked door rattled.
Without hesitation or fear, Trevor flipped the lock and Jennifer bust
through in some hastily assembled clothing. She looked like crap, but
without a shower and her hair a mess, she wasn’t fronting her best
look. None of us were.
Jennifer and I caught each other’s eye and had a moment of
embarrassment. For last night. And for this morning. She had on an
oversize t-shirt and not much else. Clearly she wasn’t wearing a bra
and her generous bosom was perked up. Her hair was dark like Trevor’s,
and straight, and only a little longer. She had actually gotten better
looking since High School, which is what drew me in last night, I
JJ walked in behind her, fully dressed. My little brother was 5’
8” with his messy brown hair totally overgrown and in need of a
haircut. That was another thing we were supposed to do today before the
wedding. He was wearing a black t-shirt and black jeans - his party
outfit from the night before. He also was wearing a huge shit-eating
Jennifer was beside herself with anger, but couldn’t figure out what to say.
JJ broke the silence. “How’d you do?” He was practically shaking in excitement and in the tension as he looked at Trevor.
Trevor broke into a matching grin. “I got the hat trick,” he responded.
“Me too,” JJ excitedly responded. I later learned that this had been a
landmark night for JJ. He had never fucked anyone in the ass before
until he did it to Trevor last night and Jennifer this morning. As JJ
had inherited my general shyness, Jennifer was the third girl he had
ever fucked. While he had been blown before, she was the first girl to
swallow (although Trevor had blown him several times and swallowed
too). JJ had been fooling around with Trevor because he was horny and
Trevor was available. This morning had been the best sexual experience
of his young life – even if most of it was obtained through deception.
“Greg,” Jennifer managed to snarl. “I think you should take your
brother and deal with him just as I will deal with mine. Now that we
know what each other’s new best friend looks like and have been
introduced a bit too personally. But get a good look at Trevor now,
‘cause I sense a return trip to boarding school is imminent.”
I nodded. Just as I had never met Trevor before, Jennifer had clearly
never met JJ until this morning. But JJ held up a finger that got both
Jennifer’s and my attention.
He cleared his throat, obviously a little uncomfortable with this
prepared speech. “There is the matter of the video of the two of you,
which is already safely uploaded to a protected website and is only
awaiting the push of a button to flood the worldwide web with the
images which include your actual names.” JJ was always great with
“You cocksucker!” Jennifer yelled.
“I don’t know how well that part recorded, actually,” Trevor smirked. I
followed his gaze to the dresser at the end of the room where a small
web cam was sitting on top of the television, aimed at the master bed.
I hadn’t noticed it, hidden by a TV Guide
“That footage is also linked directly to a private web site,” Trevor
shared, as if I didn’t know. “And there’s one in your room too,
Jennifer. One word to a friend of ours and it uploaded on every file
sharing service in the world with both your names.”
“And don’t forget the statutory rape issue to add to it,” JJ added. “We’re both still 16.”
Silence settled on the room. Jennifer and I didn’t have any cards left
in the deck. The boys had really worked this one out. All right, what
was done was done. I had great sex with Jennifer three times, but I was
drunk at the time and don’t remember it, as usual. I fucked Trevor and
he blew me. No big deal. And I was fucked for the first time in the
ass, which wasn’t fun, but, well, wasn’t as bad I thought. I’ll just
claim I was drunk the whole time, I decided, if anyone ever finds out.
I would like to see the footage of me and Jennifer though to see what
my body enjoyed.
“Let’s go home, JJ,” I motioned to the door.
His eyes were wide with surprise, but also with relief. “I parked your
car out front last night.” He tossed me the keys. JJ didn’t have a
license yet, but that was the least of my worries right now.
“We’ve got to get you dressed for the wedding,” I remarked as we walked
out. “We’ll hit the mall when it opens at 10. Then we both get
haircuts.” I guess this did bring us closer together or at least eased
some of our unspoken tensions. Certainly Jennifer is the first girl we
both had fucked – and we had each done it in three different holes just
a few hours apart. If that didn’t give us a new bond…
“What!” Jennifer shouted. “That’s it? Trevor tricks you into having sex
with him. Your brother fools me into having sex with him three times!
And you are just going to walk away. You are not going to do anything?”
I turned to this bitter young woman, wondering what I had found
attractive in her last night. “I am not thrilled by these events, but
I’d also prefer not to have my naked image uploaded all over the web
with my real name as I fuck you and fuck your teenage brother.” Some
people can’t accept reality, I reflected.
I kept speech making as I would tend to in our Mock Trial competitions.
“I can’t change the past. But I do know two things. First, we both had
repeated sex with a virtual stranger – each other. So we don’t have
much of a moral high horse to rest on when we did it again this morning
with another stranger. And we did it willingly, even with a bit of
deception.” JJ was nodding in agreement. Trevor looked self-satisfied.
Jennifer had her mouth wide open in disbelief.
“And second,” I was on a role, “if both of us hadn’t drunk so much last
night, we wouldn’t be in this situation at all. So this is a lesson for
me that is probably 4 years late. I’m going to stop drinking so much. I
suggest you do the same.” JJ looked at me with hero-worshipping eyes I
hadn’t seen since he was 11.
I turned to the door, but then turned back again. “And Trevor…”
The teenager looked directly at me with nervous anticipation.
“You give great head.” With JJ trailing along, I turned again, walked out, and headed to my car.
Check out my other stories on Nifty:
series (found in Bisexual/College) - Includes The Blow Job Task
(7 parts) and its sequel The New Class
(8 parts), the stories of two different fraternity pledge classes and
what their final tasks require them to do. (Last post 5/13/06) /nifty/bisexual/college/pledge-class
The Sex Life of Zack and Cody
in Gay/Celebrity) - Zack and Cody Martin discover they have more in
common than just being identical twins one afternoon in their suite.
(posted 2/24/06) /nifty/gay/celebrity/sex-life-of-zack-and-cody.html
Youth Group - Hotel Room Truth or Dare
(found in Gay/High School) - Four high school students – a junior, his
freshman younger brother, his junior best friend, and a senior – are
stuck in a hotel room together on a youth group trip. With nothing to
do, they decide to play truth or dare with unexpected results. (3
parts, last post 3/21/06) /nifty/gay/highschool/youth-group