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High School Friends
By Anonymous (address withheld) 

***

The following is a true story. Two teenage guys dress 
up in one of their sister's clothes and one thing leads 
to another. (mm-teens, youths, cd, 1st-gay-expr, anal)

***

I won't say what age I was, but let's say it was around 
the junior high/high school range. My friend John lived 
about half a mile down the road from my house with his 
father, who was divorced. John's sister had moved away 
to college a few months after my family had moved into 
town from Seattle.

There was nothing unusual in the friendship, and 
neither of us had ever thought much about anything 
other than what boys always think about; girls. We'd 
hang out by the entrance to school and watch the girls 
coming in, just knocked out by them. Neither of us were 
jocks, or sports types, so we didn't have much chance 
to do anything about it, of course. We were both thin 
for our age, and kept to ourselves a lot. Neither of us 
had as much as touched a girl, though not for any lack 
of trying or interest.

John's father worked clear across town, and often 
wouldn't get back home until 8 or 9 in the evening. 
Sometimes I'd hang out at John's until about then, 
watching TV, reading, horsing around. The house had a 
basement, which was a combination rec room/storage 
room, not much in it besides a few chairs, a couch, and 
a lot of boxes. When John's sister had gone off to 
college, most of her stuff had been stored down here so 
John's father could convert part of her room into a 
workroom. Sometimes we went down to the basement to 
hang out, since it was cooler there during the summer, 
and private.

**

One afternoon, we were hanging out down in the basement 
and I started poking around some of the boxes. I came 
across the boxes in which his sister's stuff had been 
stored, and much to my delight, came out with a bra. It 
wasn't fancy, or lace, just a plain white bra, but it 
was a kick to know that she'd worn it. I dangled it in 
front of John, to say look what I found. "Look 
familiar?" I said, and held it up against my chest, my 
shirt on. 

He laughed and said to give it to him. I tossed it 
across, and he did the same, holding the bra cups 
against his shirt and throwing his chest out in an 
exaggerated way. It was funny, and we didn't think too 
much about it. He asked me where I'd found it, and I 
showed him. We dug through it, coming up with armfuls 
of her old clothes, stuff she probably couldn't or 
didn't wear anymore, but which she hadn't had time to 
give or throw away. By then it was getting late, and I 
headed home.

**

The next day, I came over again, and the routine was 
pretty much the same: TV, reading comics, hanging out. 
We ended up in the basement again after a while, and I 
again started poking around in the box of his sister's 
clothes. I pulled out the same bra again, and looked at 
it more closely. It was about my size, and I mentioned 
it to John. "Put it on," he said. "No way," I said. 
"What're you, chicken?" he said. "It's not a big deal."

"If it's not a big deal, then you do it," I said. He 
shrugged and got up, going to the box. He dug around 
until he came up with another bra, a little nicer than 
the one I was holding: pink lace and pink satin. He 
held it up and then slipped his arms through the 
straps, holding it against his chest, over his shirt. 
He tried to reach around back to close it, but 
couldn't, so he stood there with the back trailing off. 
"See? No big deal."

I did the same, but it was tighter because I was a 
little bigger, and I also had my shirt on. "Go ahead," 
John said, and I took off my shirt, putting the bra on 
over my own skin. He did the same. We couldn't figure 
out how to get it on and close it, so first he closed 
the one I was wearing, and I closed his. It felt... 
funny. Tight, but I found I liked the tightness of it. 
It smelled of his sister's perfume.

Which is as far as it got that day. We joked around a 
lot, looked at each other and in the mirror, and after 
a while, I went home. The next day, when I came over, 
it was as if a decision had already been made, even 
though it had never been discussed. "Let's do it," John 
said. He rummaged through the boxes and pulled out the 
same bra, now with a slip, plaid skirt, and blouse. "I 
don't know if this is a good idea," I said. "It's 
okay," he said, "I tried it last night after you left, 
before my dad got home. It's fun."

In a minute, he had pulled off his shirt and yanked off 
his jeans and was pulling the clothes on, though he 
kept on his own shorts. There was nothing sexy about 
it, he was just yanking them on. I hesitated for a 
moment, then decided what the hell, and shucked my own 
Levis and shirt, though also keeping my shorts on.

While he got into the clothes, I rummaged around in the 
box until I came up with the plain bra, a pleated, 
checked skirt, a bright green blouse, and a slip. It 
all went on fairly quickly, and we turned to look at 
each other. It was almost funny; neither knew much 
about dressing, neither of us had made any real attempt 
at femininity, we were just wearing his sister's 
clothes, as prosaic and straightforward as that.

We both admitted that it felt funny, but it also felt 
good, in a strange kind of way. We really didn't know 
what else to do now that we'd gotten this far, and 
lapsed back into our usual routine of hanging out a 
little, and occasionally trying on something else from 
one of the boxes. When we got down to the layer with 
the lingerie and panties, we both hesitated. John 
picked up a pair of light green panties. "You first," I 
said.

"Okay," he said, and turned away from me, yanking off 
his shorts and stepping into the panties. I did the 
same, both of us turning away even though we'd both 
seen each other naked in gym class. I was hard by now, 
and he was the same, and we felt funny about letting 
each other see that. Neither of us was terribly well 
endowed; we couldn't have been more than five inches 
hard.

I pulled on a pair of plain white panties, which 
matched the bra and slip. They felt snug and soft, and 
pulled me tight. I could see John pushing down at his 
crotch to try and keep his erection down, without much 
success. "You think this is what girls feel like?" he 
asked. "I guess," I said.

"Feels good," he said, again pushing down at his 
erection, but the more he tried to make it go away, the 
harder it got. I was in much the same situation. After 
a minute, the temptation got to be too much, and since 
he was already touching it, he started rubbing it 
through the material. We didn't talk, didn't say 
anything at all during this. I did the same. After just 
a couple of minutes, he gasped, and came. I did the 
same, in my panties. 

We were both embarrassed and excited. The first thing 
we did was yank off the panties and dump them into the 
basement washing machine, where John said he'd take 
care of them later. We didn't get back into our regular 
clothes, though; only dug out fresh pairs of panties 
from the boxes.

We talked about it for a minute, how good it felt, 
catching occasional glimpses of each other in the 
mirror. Finally, he said, "Wait," and dashed upstairs. 
He came back a minute later with some of the magazines 
his father had bought and stashed in a dresser drawer. 
We flipped through the pages, still dressed in his 
sister's clothes, looking at the women and men fucking. 
It was a strange situation to be dressed in a girl's 
clothes and looking at the pictures from that 
perspective. As if it was us.

John was fascinated by one picture of a couple fucking 
doggy style. The picture wasn't very good, and we 
couldn't figure out how they were doing it. "Get down," 
he said. "What?" I said. "Look, you're dressed like a 
girl, let's see. It's just pretend."

I hesitated, then finally agreed. By this time I was so 
excited that my resistance was down. I got down on all 
fours on the basement floor, my skirt hanging down 
around my knees. Holding the magazine, he got behind 
me, between my knees, wearing his own skirt. He kept 
shifting forward until his crotch bumped up against my 
butt. Even through two pairs of skirts, slips and 
panties, I could feel his hardness. I shifted forward a 
little. "Keep still," he said, and moved forward again, 
pushing against me. He bumped back and forth a few 
times, looking at the magazine, both of us still 
completely clothed.

"I can't feel anything," he said, disappointed. Then he 
reached down and lifted my skirt up over my hips, the 
slip coming with it, and leaned in again, grinding 
against me. With one set of skirt/slip out of the way, 
I could feel the shape of him more clearly through his 
own clothes and my panties. He put down the magazine 
and started bumping against me rhythmically. 

As if that weren't enough, between bumps he lifted the 
front of the skirt and draped it over my back. Now we 
were just separated by the two sets of panties. His 
cock was sticking hard and straight out and bumping 
straight into my butt through our panties. He must have 
bumped it wrong at least once, because he shifted and 
now his panty covered cock slipped into the crack of my 
ass, through my own panties, and now rode up and down 
along the crack.

By now we were both breathing hard. I could feel his 
panties sliding down off his cock with each push 
forward, until finally it was free and sliding along my 
own panties, sometimes dipping below and slipping 
between my legs. When it did, I brought my legs 
together to give him something to shove into. The 
contact between my bare legs and his bare cock seemed 
to excite him even further. "Ahhh," is all he said.

After a while, he developed a rhythm, between my legs, 
then up along my ass, then back again. He was gripping 
my hips to hold them still while he stroked. My eyes 
were closed, savoring the sensation, particularly when 
he slid between my legs, because then it was skin on 
skin. Gradually I became aware that he was sliding the 
panties slowly down my hips until they came off and 
dropped down to my knees. His cock now rode along my 
bare ass, and I could hear him sigh with pleasure. My 
ass was getting drenched with pre-cum, making it easier 
for his cock to slide along it.

On one stroke, he pulled back further than usual, and I 
felt his cock bump against my asshole. I jumped 
slightly. "Hey!" I said.

"Sorry," he said and went back to what he was doing... 
only to bump my asshole again a minute later. 

"Cut it out!" I said. "That's enough."

"It's okay," he said, pointing to the picture. "Look, 
they're doing it that way." 

I said I didn't want to do that. 

"C'mon," he said, "if you let me do you, I'll let you 
do me. Okay?"

I thought about it, his cock still sliding around 
between my legs and along my ass, and it was so hot, so 
exciting, that finally I nodded without saying 
anything. He backed up and again bumped his cock 
against my asshole, which was already slick with his 
prec-um. He tried twice to find the right angle, and 
bounced off. He grabbed me again through the skirt, 
holding onto my hips as he again moved forward. 

His cock found my asshole, and moved around a little, 
trying to find the right angle. After a minute he found 
it, and he pushed slowly, easing in a little. It hurt, 
but not too bad, and I closed my eyes, trying to relax. 
He shoved a little more, and with a sudden pop he was 
inside me. One more slow push and he was all the way 
in. The feeling was intense, amazing. I tried to look 
back between my legs but the front of my skirt hung 
down, cutting off the view.

He pulled back, and pushed in again, slowly at first, 
then faster. I looked down to the magazine open beside 
me, of the woman being fucked by a man behind her, and 
imagined myself to be her, dressed in my skirt and 
blouse and bra. By now John was pounding hard against 
me, fucking me fast and hard. The only sounds in the 
basement were our gasps and the sound of our skin 
slapping. 

He shoved it in harder and deeper into me with every 
thrust, holding onto my hips to pull me back hard. 
Suddenly he got even harder inside me, and straighter, 
and seemed to fill me even more as he cried out and I 
felt something warm shoot out of him into the depths of 
my ass. He shoved it all the way in and held it there 
as he spasmed, gasping and shoving.

After a few moments, he pulled out with a wet sound and 
sat back on his feet. "Wow," was all he could say. "You 
okay?" 

"Yeah," I said, my ass sore but not too bad. He was 
still breathing hard.

Then it was my turn. He got on his hands and knees, ass 
facing me, skirt raised and his panties down around his 
knees. I got behind him and stroked myself until I had 
built up a good deal of pre-cum, then positioned myself 
at his ass. I pushed forward. At first my cock bent but 
didn't go in. Twice more it didn't go in, and I was 
getting hot and frustrated when suddenly I found the 
right angle, and with a sudden pop it slipped into his 
ass.

Inexperienced, eager to get going, I started stroking 
even before I was halfway inside, though each thrust 
took me deeper inside until I was completely buried in 
his ass. I grabbed his hips and rode back and forth, 
sawing into his ass, my eyes half-closed so that it 
looked as if I were ass-fucking a girl. And with his 
long hair, and the skirt, it could easily have been a 
girl. With that thought, I suddenly erupted in his ass, 
driving in hard as I came deep inside him.

Being young back then, we did it twice more that 
afternoon when we finally decided to quit, being sore 
and afraid of being caught as it got later. After that, 
we met nearly every day to dress up and fuck in his 
basement, always in his sister's clothes.

FIN

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Kristen's collection - Directory 58