I applied pressure to her asshole with the
tip of my dick and it began to
slide into her ass. I felt the tightness of her sphincter.
keep pushing," she said. I felt her push her hips back
and more of my dick
was inside her. She was taking deep breaths.
"Stop for a second," she said.
"Everything OK?" I asked.
"Sure," she said, "I just need
to let my ass get used to the size of your
dick. It feels really good."
We sat like that for several seconds, and
then she told me to continue. I
pushed a bit more and felt my cock work past the outer ring.
At that point,
it slid in all the way. I was in! My cock was up her ass.
"OK," she said. "That feels
really good. Now, very slowly ease back."
I did as she said, pulling back a few inches,
and then starting back.
"That's it," she said. "Go slow at first."
I tried, but couldn't help beginning to pick up the pace.
It was so tight,
so hot, so nasty. Before I knew it, my thrusts were causing
her ass to
shake. The pressure in my balls was building.
"I'm gonna cum," I said and began
shooting my sperm into her ass.
"Yeeesssss," she said. "Oh
that cum feels so good."
I emptied my balls and then eased out my cock.
We both fell onto the bed.
"Wow, that was great," I said. "Now,
it's your turn. My dick won't be ready
for a few minutes, but I'd love to eat you."
"Are you sure?" she asked.
"Of course," I replied, "why
Jane sort of grinned and then turned the lamp on again. "OK,
eat me," she
I got on my knees by the side of the bed.
She was sitting up with her feet
on the floor. I pushed her legs apart and — surprise
— a dick sprang up at
"Holy shit," I exclaimed. Caught
by surprise, I sort of leaned back. Jane
reached out and put her (or his?) hands on my shoulders. "I
know you've had
fantasies of being with a guy," she said. "Peg told
us what you told her at
the newspaper the other day. I heard you talking after the
movie. Now's your
Still a little unsettled, I thought, yep,
here's my chance. "Sorry," I said.
"I was just a little taken by surprise."
"I understand," she said. "Do
you think you can do it? Can you suck my dick?
I hope so, honey, because I've jacked off for two years thinking
sucking and fucking me."
I looked at Jane and realized it was true.
She had a real crush on me. I
also realized that my dick was getting hard as the thought
of sucking and
fucking her worked its way through my brain. I leaned forward
and kissed her
lips, gently. We kissed some more and I fondled her tits.
I kissed her neck
and worked down to her tits, sucking each one. I then began
licking my way
down her torso. She lay back on the bed.
Out of the corner of my eye, I could see her
erect penis. I was moving
closer and closer to it. Finally, I had worked my way down
to the tip.
I took her cock in my hand and stroked it
gently, trying to hold it with the
same pressure I used on mine. I looked at it for a moment.
This was the
moment of truth. I was about to suck a cock.
I leaned forward and let my lips engulf the
tip. Jane gasped and her cock
twitched. Hmm, I thought, that tastes OK. I then began to
take more into my
mouth, trying to simulate the movements that had made me feel
good when my
cock got sucked. After a couple of minutes, I developed a
rhythm and began
moving my head up and down the shaft, taking a little more
in each time. I
wasn't able to quite take all of it (after all, it was my
first time), but I
did the best I could. Suddenly, Jane moaned loudly and said,
Sure enough, before I knew what was happening,
her cum shot into my mouth
and down my throat. I was caught by surprised and semi-gagged,
and was able to swallow some of it. Probably half of it dripped
out onto her
When she had stopped cumming, I crawled up
the bed and lay next to her. She
turned her head toward me, put her hands on each side of my
face and kissed
me deeply. "That was wonderful," she said.
"Yeah, right," I responded.
"No, it really was. I've never had a
first-timer before. You were wonderful
fucking me and sucking me. Some guys, when they find out I'm
a T-girl, try
to hurt me. You didn't. You made love to me," she said.
"Well, I have to admit I've fantasized
about this. Now, I've done it."
Her hands moved down to my cock, which was
now hard again. She looked deeply
into my eyes and said, "Fuck me. On top. I want to see
your face as you fuck
I got some more lube, applied it and positioned
myself between her legs. She
pulled her knees back and apart as far as she could. I looked
down at her
cock, which must have been about six inches. Her cock and
balls got me
excited. Already hard, my cock seemed to get harder and longer.
I placed the
tip against her asshole and gently pushed forward. After being
my cock earlier, her ass easily accepted me again. I looked
down at Jane.
Her eyes were closed, but a look of pleasure was on her face.
I didn't move,
and she opened her eyes. She looked at me for a moment and
sensed what I
"Fuck me," she said softly. "Fuck
my ass with your cock. Shoot your hot cum
up my ass."
I began to move back and forth inside her.
Again, it was easier this time
but still very tight. I had read enough about anal sex to
know that you
really can't just pound away, but I thought my motion was
good. Jane seemed
to think so.
As I fucked her, I again looked down at her
cock, which was getting hard.
Although female in most ways, it went through my mind that
I was fucking a
man. And I liked it. I took her cock in my hand and began
to stroke it. It
got harder. I tried to create a rhythm with my thrusting and
hand strokes. I
must have done OK, because suddenly Jane screwed up her face,
began pumping cum. It wasn't shooting out, just a steady stream
of her cock. When she stopped, and while I was still fucking
her, I put my
hand to her mouth. She licked some of the cream away, but
I pulled my hand
back. I stopped thrusting for a moment, looked her right in
the eyes and
brought the cum to my mouth. I licked my hand clean.
I resumed fucking her. Just a few strokes
later, my loins clutched and I
pumped cum into her ass.
This time I didn't go home. Jane and I snuggled
on her bed for a while, and
then we got up and took a shower together. Both of our dicks
were worn out,
so we just bathed each other, went back to bed and fell asleep
other's arms. During the night, I woke briefly. I looked down
at the person
next to me. She had great tits and a nice cock. I never would
it. As I drifted back to sleep, I heard moaning from another
room. I had
almost forgotten about Peg and Christy. It sounded as if they
A few days later, Peg and Christy went home
for the Christmas holidays. Jane
stayed in town. After some prodding, she confessed that it
was hard for her
to go home. Her father was having a hard time adjusting to
the fact he had a
son and daughter in one. Jane had lived as gay for a while,
got implants and made herself into a woman. The operation
had been performed
just a few years before. She said she and her father were
that it was still difficult.
We spent most of the holidays together. It
was kind of cool walking around
town with this young, attractive woman who also had a dick.
Yes, we fucked a
lot but not all the time. Christy came back early from her
hometown, and we
had some hot threesomes. I told Jane I liked being with her
but still liked
pussy. She said she did, too, that's why she hadn't had a
On New Year's Eve, I let Jane fuck me in the
ass. It wasn't as painful as I
had expected but still took getting used to. Christy was right
there with us,
coaching both of us along. At one point I was fucking Christy
with me on top
and Jane on top of me with her cock up my ass. Peg walked
in right when we
all came. Her hot, black pussy was enough to get us going