A guy is caught in a compromising position

We shouldn’t have been doing it. Well, I suppose it
really didn’t do any harm, at least it shouldn’t have
done any harm. I guess we’d done that sort of thing
before, well… when we were a lot younger.

I-I… we had our pants down. No, it’s not what you
think. I think we just wanted to see what we looked
like. Like I said, Dan and I had done the same thing
before when we were younger. Just looking.

It was just about silent. Any talk would have been
strange. My pants and underpants were down and so were
Dan’s. We were behind his father’s shed and only the
woods were behind us and no one was around. I looked at
his cock and he looked at mine. I hadn’t been able to
look too closely at other boys’ cocks, and I was
curious. You wouldn’t want to be staring in the locker
room!

Like I said, we’d looked when we were little, but now
that our cocks were, well, developed, it was only with
Dan, who I’d known just about forever, that I’d even
think of doing something like this with.

I didn’t even consider touching it: I merely wanted to
see it. He’d looked closely at mine too, also not
touching. It was so quiet. No one was around.

“Uh, better get dressed,” said Dan, rather quietly, but
sounding concerned. I looked up to see him looking over
my shoulder into the woods, appearing rather stricken.
Then he was pulling up his pants. “Deborah!” he hissed.

I had my pants up in a panic. We rushed away, toward his
house. “Did she see us?” I asked. He didn’t answer,
though I know he heard me.

Of all the people to catch us. Why did Deborah have to
see me like that? She was a year older than us — a
junior — but I’d had a crush on her for years. Well, I
guess she’d finally noticed me. Ha! I wanted to fold
myself into another dimension and disappear.

Dan and I closed the back door, and looked at each
other, catching our breath.

“I don’t think she’ll tell anybody,” he said. I couldn’t
respond: I still felt sick to my stomach, her seeing us
like that.

I thought about going home. Would she see me leaving the
house? I realized I wouldn’t know when it would be safe
to leave. What did she think of us? A couple of kids. I
didn’t want her to think of me as a kid. But if she
thought of me as anything else…

“She won’t tell anybody,” repeated Dan. I felt he was
right even though just the thought of the alternative
kept me feeling frightened. The doorbell rang.

It was Deborah. We both stared at her, having opened the
door before we realized. “Hi, boys,” she said, walking
in uninvited.

“Hi,” said Dan, in a wary voice. I think I mumbled
something, but I was too paralyzed to do much else. We
followed her into the living room.

“Your parents are gone,” she said it to Dan — not a
question but a statement. We didn’t say anything. “I saw
you,” she continued. I thought she might just be pausing
in the middle of a sentence, but then realized she was
done. Then she smiled.

I loved that smile. Seeing her smiling at her friends. I
recalled the few times she’d smiled just for me. I used
to think about her when I lay in bed: just her and me,
imagining that we were out on our own. “Don’t be
embarrassed: it’s OK,” she finally continued.

Dan giggled briefly: “You’re all right,” he said,
obviously relieved.

“It doesn’t bother me, I’m not prejudiced,” she
responded.

I looked at her, trying to make out what she was saying.
Dan looked confused too. “I am curious,” she went on,
“how you do it.”

“Do it?” asked Dan, still looking confused.

“Yes, you know, when you do it.”

“Do what?” I said.

“You know!” she said, smiling again. “What you guys do.”

“You think we’re homo?” said Dan, suddenly. I felt
another panic — Deborah thinks that we’re… that I’m
homo!

She giggled. “Look, I saw you, I told you it doesn’t
bother me.”

“We were just…” said Dan, suddenly seeming to lose his
ability to speak. “…just… looking,” he finally
managed to stammer, his voice weak.

“I said it doesn’t bother me,” she insisted. “Come on! I
am curious.”

“But we’re not!”

“Look,” she said, then pausing for a second. “I won’t
tell anybody. I saw you.”

“But…”

“Hey, I know no one wants to admit they’re homo. But I
saw you back there. You can admit it to me.”

“But we’re not!” I managed to stammer.

She looked slightly exasperated, then said, “OK, you’re
not going to admit it.”

“But…but…” I started again, seeing that she wasn’t
believing us.

“You want me to tell everybody?”

I stared at her. Dan did too. She seemed a little
peeved. “But we’re not,” I finally said again, feeling
weak.

“I’ll tell everybody what I saw,” she answered.

“But…”

“I will!”

I spoke again, “Deborah, please…”

“Just stop it!” she said loudly. Silence. “Stop
repeating that.”

We just sat there, no idea what to do. She spoke again:
“I’m just curious, that’s all. I know you can’t admit to
it. I just want to know how you do it.”

“Deborah…”

“OK, don’t admit it,” she said, and paused. Then: “Do it
again… what you were doing.”

“Deborah!”

“I’ll leave! And tell.”

I looked at Dan and he looked at me. How had she gotten
these ideas in her head? “I’ll tell everybody at
school,” she said. “Just what I saw…” I glanced at Dan
again and he was looking so nervous. “Pull down your
pants again.”

I touched the buckle of my belt and Dan did the same
thing. Soon we were both unbuckling. And unbuttoning and
unzipping. And our pants were down. “Your underpants,”
she said.

We were both standing there, in front of her. She looked
at my cock and at Dan’s. She looked up at both of us.
“I’ve got to see it.”

“What.”

Suddenly she was darting out of the room. “Stay like
that,” she said as she left. I looked at Dan and he
looked back at me. Who would have believed the position
we were in? She was back with a tube in her hand. “I
want to see how you do it,” she repeated.

“Deborah…” I started again.

“I’ll tell!” she responded. She looked at my cock again.
“Take off the rest,” she said, obviously to me.

What could I do? I did it. Naked. She just looked at me,
and walked around me, inspecting me. While she was
behind me, she put her hand on my rear cheek and ran it
up and down a little. Deborah touching my rear!. In
front of me she smiled again. “Get down on the floor.” I
didn’t move. “I’ll tell.” I got down. “Your stomach
here,” she said, indicating the seat of the sofa.

“Deborah!”

“I’ll tell.”

I got down.

“Get behind him,” she said to Dan. “Put some of this on
your cock,” she said. “Do it, or I swear I’ll tell.”

He was behind me!

“Get it hard!”

I couldn’t believe this!

“OK, do it. I want to see.”

Nothing happened.

“I’ll leave now. And tell,” she said. Dan touched my
hip, then sort of grabbed it. I knelt there. How could I
be in this position? Deborah right here! I felt his cock
against my rear.

“Push it in,” she said. “Show me… I want to see it all
or I’ll tell…”

I didn’t think I could do this. I had to stop it. I
didn’t know what to do. Dan pressed. I had to do my best
to let him in! I didn’t have any choice! “Oh wow!” I
heard her say. I could hear a smile in her voice. Was
she laughing at us? It didn’t seem like it, but I still
wanted to die right there.

I felt it sliding in. He pressed. His body bumped my
rear and I realized it was all the way in. “Do you slide
it in and out?” she asked. Dan didn’t say anything. “Do
it,” she finally continued. I felt Dan start to pull it
out, then back in. Then faster. And faster. And on and
on he went.

And I felt it. Him spurting in me. I heard his breath
catch. He’d been breathing heavily. I didn’t look at
him. I couldn’t. I couldn’t look at Deborah. “Oh wow!”
she repeated.

He just knelt there behind me for a second, still in me,
exhausted. Then he was out of me. I heard the sound of a
kiss. Then suddenly Deborah was grabbing my head and
kissed me on the cheek. “Thanks,” she said to me
quietly, and then I heard her leave.

Then Dan was gone and I was there, alone in his living
room. I quickly got dressed and left.

“Listen, I want to talk to you.” It was Deborah,
catching me in the hall, the next day at school. She
didn’t usually pay me much attention other than when we
were in our own neighborhood. She pulled me toward a
less crowded hallway.

“Listen, thanks again,” she said, smiling at me. I loved
that smile.

“Deborah, we’re not gay.”

“Look, I know you can’t admit it, I just wanted to thank
you again: I’d always been curious about how you do it.”

“Deborah,” I hissed, but she walked away.

***

The next day, at lunch, she sat with me! I was sitting
alone and she just came up and sat across from me! She
smiled at me: a shared secret. “It was fun,” she said,
“you don’t mind so much that I watched, do you?”

“Deborah, I’m not gay!” I said, keeping my voice low.

“I’m going to ignore that. How often do you two do it?”

“We don’t!”

“Please tell me? I won’t tell.”

“But we don’t!”

She didn’t say anymore. She did smile at me a little
through the rest of lunch, but we just sat there. No one
sat with us: I didn’t really have a group to sit with,
and her friends were on the other side of the cafeteria.
The next day at lunch, she was back again.

“I want to see it again.”

“Deborah, we aren’t gay!”

“I’ve read that gays often deny it.”

“But we’re not!”

“I want to see you two again.”

“Deborah…”

“I’ll tell!” I stared at her. “I’ll tell everyone what
you two did.”

***

That afternoon Dan and I were at her house. We’d been
sort of avoiding each other since she’d left us there in
his living room. Once again, she watched us both
undress, cajoling and threatening us, then I knelt
against her sofa while Dan did me again.

And that wasn’t the end of it: a week later, she
demanded that we show her again. And again. We’d be at
her house and she’d have us both undress completely.
She’d give us a tube of K.Y. jelly and Dan would put it
on his cock and I would push some in my rear. And he
would do it to me.

And at lunch, she’d interrogate me: “What does it feel
like?” I didn’t know how to answer questions like that.

It was so ironic. Before, I wouldn’t have dreamed of
eating lunch with Deborah every day and now that is
exactly what I was doing! And a part of me loved it. It
was so weird, her talking to me every day as if I were
gay and continuing to ask me what it felt like and why I
liked it and everything. And any time I told her I
wasn’t gay, she’d just refuse to listen to me. And if I
tried to refuse when she wanted to watch Dan and me,
she’d threaten me again.

She was so curious. But there just wasn’t much I could
tell her. I didn’t really want it. And there were only
so many words you could use to describe the physical
sensation. But she just kept asking.

Then one day she said, “I know how it feels.” I looked
at her: she was going to start telling me how she
thought it must feel. “Dan and I pretended I was a boy.”

“You what?!” I gasped.

“I did what you do.” She was all smiles. “I told Dan to
pretend I was a boy and it worked: he did it! Then she
was silent for a while. “I’m sorry: are you jealous?”

“No!” She had had sex with Dan! I was jealous as hell.

“I’m sorry… I want to see you two do it this
afternoon.”

My mind raced. She’d let Dan do her rear! It was
unbelievable. That afternoon she knelt next to me as he
did it to me. “It feels so full, doesn’t it?” she said.

I managed to say yes. She reached under me and briefly
touched my cock, then withdrew her hand. Then she
whispered in my ear “so full, so full” while he was
doing me. He came.

Then soon after that, she told me she’d gotten Dan to do
it to her again. Soon she was reporting such encounters
about as often as she was making me come over to her
house so she could watch me and Dan.

I was in love with her. Maybe it had been a crush
before. It was so stupid: how could I get so hooked on
her when we were in this weird relationship?

But I was so frustrated. Once I suggested we go out. She
treated it like she always did whenever I said I wasn’t
gay: she just talked as if I were in denial as she said.

It was too much. Other girls wouldn’t look at me because
I ate lunch with Deborah every day. I didn’t have many
other friends, and Dan and I now avoided each other
except when we were at Deborah’s.

I finally asked a girl from another school to go out
with me. I didn’t have a license yet so my parents ended
up dropping us at a movie and picking us up. Cathy was
nice and I lay in bed thinking of her. I realized I
could like her instead of Deborah.

We went out again, again to a movie. In the theater she
said: “A girl told me about you.”

“Who?”

“That girl in your neighborhood, Deborah. About you and
that other boy.”

“What did she say?!”

“Listen, it’s OK, I know you don’t like to admit it. I
know you’re trying to cover up, going out with me. I
don’t mind… too much.”

After that time, she wouldn’t go out with me again. And
it was the same the whole school year and the next.

Deborah stayed in town to go to college. She still had
us over once a week or so. And she’d call me on the
phone and tell me about doing it with Dan. “Pretending
to be a boy” as she said. “Listen,” she asked once: “I
read that guys like to do it rough to each other. Does
Dan like to do it rough?”

“Deborah!” I said, exasperated.

“Do you like it rougher?”

***

The next night, she called me again. “I got him to do it
harder. I think he liked it better that way — I think
it makes it easier for him to imagine I’m a boy.”

Then when we were at her house, she insisted that Dan
let loose and show her how we did it rough. He shoved me
onto the floor, my rear in the air, grabbed my hips, and
banged hard into me — I couldn’t believe what was
happening. After that, she was always encouraging him to
be rougher with me, and he would grab me while I was
still dressed and practically rip off my clothes.

He shoved me against the wall sometimes and forced me to
do it one way and another. It made me realize exactly
how strong he is. And on the phone, Deborah told me what
an animal he was with her.

Eventually Dan and I graduated. That summer, Deborah
came over to my house one day and showed me her left
hand: she had a wedding band on!

“We did it!” she said, gleefully. “We’re married now!”
Who? Her and Dan? I wasn’t aware of anyone else she was
seeing! I felt like something had hit me in the chest. I
just didn’t understand — I didn’t understand anything
at all. Then I noticed she was looking worried: “Uh, it
doesn’t change anything: I don’t mind if you two still
do it.”

“Why did you marry him?”

“Well, it seemed to work, him pretending I’m a boy.”

“But…” Was that a reason? It seemed to work?

“Listen, I’ll tell you a secret,” she said. “I kind-of
wish it was you I married. But Dan seemed to be able to
make it work, the pretend business.” She kissed me on
the cheek, but immediately drew back. Then she was gone.
Aaarrrggghhh!

And all was back to the usual: she had me over; she
watched Dan do my rear; she told me all about their sex.
I couldn’t believe some of the things she told me–she
let him hold her by the hair while he did her — she let
him tie her hands. She let him tie her spread-eagle,
face down on the bed and do her.

She wanted me to do the same with him. I had no choice.

I had to do something: anything to get out of this. I
decided to move to another city. I didn’t tell Deborah –
– I just quietly planned and arranged it. I felt like I
needed to break out of this life.

And I did it, never telling Deborah or Dan a thing —
where I was going or anything. I got a job. And signed
up for community college courses. And actually dated.
And met Rachel.

And I felt Rachel was my savior: the one who would make
me forget Deborah. Once again I was on track. And I was
a virgin-of-sorts with Rachel, but not for long. Soon we
were mostly living together and engaged. It was so sweet
sleeping with her every night, making love whenever we
felt like it. It was just what I needed.

We were growing more confident with each other, though
naturally I told her nothing about Deborah or Dan. We
started being a little daring: we rented X- rated videos
and watched them while we were in bed. Once, with a
little clever planning, we managed to do it in a public
park in the middle of the day. She was becoming more
confident about asking for things in bed, and so was I.
I felt like my life was finally on track.

And one night after we made love, she lay there on her
side, playing with my cock and she whispered in my ear:
“I did what you want.”

I didn’t quite understand what she was saying, so I just
relaxed, enjoying what she was doing to me. She repeated
it: “I did what you want.”

“What do you mean?”

She giggled. “I met your ex-girlfriend and she told me
what you like.”

“Huh?” Saywhat?

“How she lost you because she wouldn’t, you know.”

I couldn’t quite sort this out. “What did you do?” I
asked, deliberately.

“I let another man do my ass.” I lay there stunned. “She
told me how you couldn’t make yourself stay with her
because you wanted so much for her to go out and do that
and she couldn’t make herself do it.”

“Who was she?”

“Your old girlfriend! I met her a couple of weeks ago.
She told me all about you before you moved here. She’s
real nice. She got her husband to do it with me.”

She’d let Dan do her rear!

“It was so nice of her to warn me: she said you’d kept
your desires bottled up and ended up leaving her before
she had much chance to get used to the idea after you
finally admitted it to her.” She’d let Dan do her rear!
“I’d do anything for you. You remember that.” I’d never
done her rear or anything like that!

I was in a daze all day. I’d tried calling Deborah, but
no answer. That night, Rachel looked frightened. She
said: “Today… she told me about you and Dan.”

Deborah was still in town? But I knew exactly what
Deborah had told her. “Where is she?” I asked, feeling
wary.

“They’re coming here.” I almost collapsed in my chair,
feeling defeated. I was in a daze. They arrived, Rachel
letting them in. I said hi, but it was like I was
watching the whole scene from afar. Deborah was in form,
giving the orders. Rachel undressed. I watched Dan do
her. He flung her around, shoved her body over the back
of a living-room chair and fucked her rear so hard. She
seemed out of it, in her own daze.

Deborah ordered me to undress. I waited patiently,
leaning over the same chair. Deborah and Rachel watched
him do me. Deborah held Rachel’s hand as they watched.
Rachel’s eyes were huge, glued on me.

Then Dan did Deborah. He was much rougher on her than he
was on Rachel or me–I couldn’t believe how wild he was
with her. Deborah managed to look at me through her wild
hair while he shoved into her.

They come up to visit sometimes. Dan does the three of
us. When they arrive, he tells us to strip. And he has
us do things like touch our toes, or kneel and put our
heads to the floor. We serve him dinner, his naked
slaves. We suck his cock. Sometimes he likes to use a
belt on us. When he is fucking me, I see Deborah holding
Rachel’s hand. Sometimes she touches Rachel’s body a
little, but Rachel’s eyes are always glued on Dan and
me.

While Deborah is getting it, Rachel clings to me.
Deborah is always watching me as best she can. Rachel
always stares into space while she is getting it, or
shuts her eyes, completely oblivious to Deborah and me.
Then Deborah and I sit with our arms around each other
and talk.

She’s told me a lot during those talks. About seeing Dan
and me in his back yard that first time, and how she
stared at my “cute little ass”. And how something made
her think about seeing a cock sliding into it. And her
sudden realization that she might see just that.

And how hot and frustrated she was when we ran away, and
how she knew she’d have to get us to do it somehow. And
how she masturbated furiously after every single time
she watched me and Dan.

She kisses me a little sometimes: on the mouth. And
whispers in my ear how much she loves me.