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Advising 101 Part II


Fortunately, the next couple of weeks at the student newspaper went almost
as if nothing had happened. We worked together and none of the girls
indicated anything different when others were around. However, whenever two
of us were alone or just the four of us were in the office, they made
slightly teasing comments or simply gave me very seductive winks. My mind
still hadn't been able to process all that had happened.

One day Peg and I were on the office alone and she said, "We're kind of
ready to get together for dinner again. If you are."

"Sure, anytime," I said. "I haven't really known what to say. That was the
most incredible sex I've ever had."
"Really?" she said with a smile. "I'm glad. Let me ask you something. You
know that the three of us fuck each other. Have you ever had sex with a
man?"

I wasn't sure where this was going, but after what we'd done to one another
I didn't see any reason to dodge the question. "No, I haven't," I said.

"Have you ever wanted to?" she asked.

This caused me to squirm a bit. One of the fantasies I had never shared with
my wife was my thoughts about sucking a cock. It wasn't a strong enough
desire to really pursue, more curiosity. What did it feel like? How did it
taste? What was it like to have someone inside your body? These were things
I had wondered about.

"Well, I'm not sure it has ever been a desire, but I've wondered what it
would be like," I told Peg.

"Cool," she said. "I understand. Can you come over tomorrow night?"

Could I come over? Hell, I was ready to go right then. "Sure," I said, "what
time?"

"Oh, whenever," she answered, and then began gathering her books and things
to leave. She had on a short skirt, and when she bent over straight-legged
to pick up her backpack, I got a nice view of her pussy. She wasn't wearing
panties. She looked over her shoulder at me, smiled and walked out.

 


 

My instant hard-on was almost painful.

During the next day, I thought about my impending fuck-fest and decided that
Jane would get most of my attention. She hadn't been fucked the first time
and seemed OK with it, but, hey, fair was fair.

When I arrived at the girls' apartment, Christy answered the door stark naked.
"Hi," she said cheerfully. "Come on in. Want a drink?"

I asked for a gin-and-tonic and she sashayed to the kitchen to make it. Peg
was sitting on the couch wearing just thong panties. I sat down next to her,
and she gave me a long, deep, tongue-filled kiss. "Good to see you, too," I
said.

Christy brought my drink. I took a gulp, and then asked, "Where's Jane?"

"She's studying," Christy said. "Say, would you like to watch a porno?"

"Sure, if that's what you guys want," I said, although I didn't see the
need.

Christy walked over to the DVD player and started the movie. Soon the TV
screen was filled with people fucking and sucking. My dick began to respond,
and Peg moved her hand to my crotch and began a soft, gentle rub. Christy
snuggled under my arm and placed my hand on her tit, which I began to
fondle, gently squeezing her nipple between my fingers.

The movies featured your basic sucking. One particularly good looking girl
was wolfing down some guys dick, giving an impressive blowjob. She swallowed
most of his cum, but allowed a little to dribble out, proving that he had
cum. The guy then began to pull down her panties. When he spread her legs, a
hard dick popped up.
My heart lurched. Another part of my gay fantasy had been to have sex with a
transgender. I tried not to reveal my reaction, but my dick twitched
uncontrollably. Both girls must have been waiting for that scene, as they
both noticed.

"Like that?" Peg said with a slight tease in her voice.

"Well, it's certainly interesting," I said as the couple on the screen
continued their action. The guy, after some initial surprise, had begun to
suck the T-girl's cock. It was now hard. After a few minutes, he stood up,
pushed her legs back and farther apart and placed his cock at the entrance
to her ass. He slowly pushed forward.
By this time, Peg had my cock fully in her hand. As the actor began to move
back and forth in the T-girl's pussy, I couldn't hold back. I shot my cum
straight up in the air. Christy quickly leaned over and took my cock in her
mouth and milked me dry.

"Well, that was interesting," Christy said. "Do you like the idea of fucking a
T-girl?"

Again, there was no point in trying to deny it or claim it was just the heat
of the moment. "Well, yes, I've fantasized about fucking a T-girl," I said.
"I don't think I'm gay. I've just wondered what it would be like to suck a
cock and fuck somebody in the ass. I've never done anal."
"Would you like to?" Peg asked.

"I guess. What's up?" I asked as it became clear this was all planned.

"Go upstairs and find out," Christy said. Then they both got up and went to
the back bedroom and left me sitting there.

I sat for a moment trying to figure out what was happening. Finally, I
decided that Jane was into anal sex. I walked up the stairs to her bedroom
and tapped on the door. "Come in," she said.

Like last time, she wore only a pair of thong panties. The room was dark
except for a lamp next to the bed where she sat. She got up off the bed,
came over and kissed me. "How are you? Did you like the movie?" she asked.
"It was pretty hot," I said. "I guess you're into anal sex, right?"

"Yes, you could say that," she said and kissed me again. I began running my
hands over her body, reaching around and squeezing her ass. My dick was
getting hard again. We began to pull off my clothes, and as soon as I was
naked, she dropped to her knees and began to suck my cock. It felt really
good.

However, just was she was getting into a good rhythm she stopped and stood.
"I'm into anal sex all right," she said, "and I want you to fuck me in the
ass."

She opened a drawer on the night stand and took out a bottle of lubrication.
She squirted some on her hand and slathered it on my dick. Then she squirted
some on my hand, turned and bent over. Just as I started to ease down her
panties, she turned off the light. I put my hand on her ass and began to
massage her cheeks and then her asshole. I rubbed in the lube and eased a
finger into her ass.

"You're going to have to kind of guide me," I told her. "I've never done
anal."

"OK," she said, and reached between her legs and grasped my dick. This
forced her to bend way over, but also put her asshole in perfect position.
She positioned the tip of my dick against her rosebud and then said, "Push
gently, just like you did with your finger. Go slow and stop when I tell
you."



 

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. "That's good;
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 not."
Jane sort of grinned and then turned the lamp on again. "OK, eat me," she
said.

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
full attention.

"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
chance."

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 about you
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, "I'm gonna
cum!"

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, but recovered
and was able to swallow some of it. Probably half of it dripped out onto her
thighs, however.

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
me."

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 stretched by
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
wanted.

"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, gasped and
began pumping cum. It wasn't shooting out, just a steady stream pulsing out
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 in each
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 have believed
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 hadn't.

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, but eventually
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 communicating, but
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 sex-change
operation.

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 again.

 


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