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 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. "Good," 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 precum, 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 precum. 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 assfucking 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, 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 other day to dress and fuck
in his basement, always in his sister's clothes.