****** On Becoming Friends and Lovers by The Freshman ******
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On Becoming Friends and Lovers


I had taken a new job in a new city. I did not know a single person in town.
The hours were long and, as a result, I had little chance to meet new people.

Cindy and I met at work. She and I work for the same company. Her office is
down the hall from mine.... They say that misery loves company and she and I
became friends during the many late nights we worked. She was my opposite - I'm
kind of quiet and shy and she's a real firecracker. But we could talk to each
other. Even when not working, we could close coffee houses and bars, just
talking for hours.

After a while, our conversations would invariably turn to sex. At first, I
think she was just trying to embarrass me, but it began to turn us on. We would
talk about likes, dislikes, past experiences, and fantasies.

One night over a bottle of wine, Cindy told me that one of her fantasies was to
see two guys have sex. She told me that the thought of watching two men perform
oral and anal sex on each other drove her wild. It was her favorite fantasy to
replay in her mind when masturbating.

Then she turned the tables. "Did you ever think about it?"

Trying to avoid the topic, I played dumb, "Think about what?"

Cindy did not let me off the hook, "You know exactly what I'm talking about.
Did you ever think about having sex with another guy?"

Maybe it was the wine, or maybe it was because I truly felt comfortable with
her, but for the first time I admitted that I had experimented in college with
gay sex. She was stunned. She wanted to know every detail. So, I began to
explain my experiences:

"It was not a big deal. I met this guy in one of my chemistry class and we
became friends. The class was impossible and to get through it we began to
study together. It worked. It was a study group of two. One night while
cramming for finals, I fell asleep in our little study room. As I slept, he
loosened my sweat pants, reached through the fly of my boxers and began to rub
me. I woke up but did not stop him because it felt so good. He then gave me the
best blowjob I had ever had. After I came, I slid off of my chair onto my knees
and returned the favor. After first I was nervous, but the smell of his sex was
intoxicating and before I knew it I had swallowed his cum. He even got me try
anal sex a couple of weeks later. By this time, we would have oral sex whenever
we could and he wanted to take it to another level. One night I let him. After
he had just sucked me off and thought I was going to do him orally, I handed
him a small tube of KY Jelly and told him 'Take me.' He lubed me up and I
lowered myself onto his lap. After that, we made love whenever we could - that
is, until the end of the semester. Over the summer he transferred to MIT and
that was the end of my experimentation."

Cindy was in shock. Her hands were ice cold, but her nipples were hard and her
face was flushed with excitement. "Do you still think about it?"

"Not really. I think it was just a phase."

After the conversation, I did not give it much thought. I chalked it up to
talking about ancient history and Cindy and I continued on as friends.

A couple of weeks later, Cindy invited me to join a group of friends for dinner
and dancing at the clubs. When I got to the restaurant, there was only Cindy
and a guy named Roger. Cindy explained that three others had cancelled. We
enjoyed our dinner and then hit the dance club. We were having a good time and
Cindy was making sure that I was getting enough to drink. I did not give it
much thought, but afterwards I realized that all of those shots that Cindy was
buying were all part of her plan to live out her favorite fantasy.

Around 2 a.m., we left the club. It was cold and there was not a cab in sight.
Roger suggested that we all crash at his place, a couple of blocks away. Faced
with the option of waiting in the frigid air for a taxi that was never coming
or crashing at Roger's place was an easy call. We jogged to his apartment.

Roger lived in a restored brownstone in the yuppie section of the city. He
actually owned the entire building and had converted it into a triplex. He was
an architect and the place was unbelievable. The best feature was the hot tub.
He had replaced the entire back wall of the building with these long windows
that went up all 3 stories. You could see 30 feet up. The windows were tinted
so that you could see out but no one could see in. At the bottom of the windows
was the huge marble hot tub. From the hot tub, you could see all of the
twinkling lights of the city against the river.

Roger suggested that we jump in the tub to get the winter's chill out of our
bodies. It sounded like a good idea, but even in my drunken haze I asked about
swimsuits. Cindy interrupted, "You dummy, we'll go in naked. It is not like you
have not already seen what private parts look like. We're all adults." This
also made perfect sense. So I stripped out of my clothes and joined Roger and
Cindy in the tub.

The water felt really good. Roger turned on some jazz and opened a bottle of
champagne. The bubbles around me in the tub mixed perfectly with the bubbles in
the champagne. We finished off the bottle and Roger got out of the tub and
grabbed another.

Roger stood in front of me completely nude as he opened the bottle. He was
about 5'11" with dark skin and a muscular frame. He was completely hairless
except for a small triangle around his penis. Even soft he appeared to be well-
endowed. I felt a tingle, but figured that it was from the champagne and hot
water.

Roger got back into the tub, his penis "accidentally" brushing against me as he
passed by. I shivered. Something deep inside me was awakened. And Roger and
Cindy knew it. I put my head back and closed my eyes, hoping that the feeling
would pass. I heard some splashing and opened my eyes to see Roger's cock
inches from my mouth. I could see the tiny bits of foam from the hot tub
hanging delicately on his thatch of pubic hair.

I could not fight it any longer. I opened my mouth and took him inside. I
tickled his tiny slit with my tongue as he passed into my mouth. My lips hugged
each and every bump and ripple along his shaft. Although I had figured that
Roger was well-endowed, having seen him while still flaccid, I was still a
little surprised by his girth now that he was hard. At first I gagged as his
mushroom-shaped head hit the back of my mouth, but my past experience soon
began to take over and within minutes I was caressing him and moaning as I
sucked him deep into my throat. I eased his cock, now slick with my saliva all
the way down until I could gently lick his balls with my outstretched tongue. I
could taste the delicate saltiness of his pre-cum now oozing from his cock. It
had been too long. I missed this feeling.

Cindy was sitting on the edge of the hot tub, watching intently. In no time,
she was rubbing breasts with one hand while fingering her clit with the other.
She licked her lips and a small moan escaped as she thrust a finger inside her.
From the corner of my eye, I watched her sink her finger deep within herself
and then pull it out covered with her own musky sex.

Roger began to hump my face. At first, he was tentative, even gentle. But the
feelings inside became too much for him to handle and his fiery passion
erupted. He was literally fucking my mouth. Watching this, Cindy managed to
squeeze three fingers inside her vagina while furiously rubbing her clit with
the other hand. She began to buck against her own hand. Soon the sounds of our
collective moans, the slapping of Rogers balls against my chin, and Cindy's
masturbation joined the jazz in the air.

Roger grabbed my face and pulled me close. We all knew what was going to
happen. By this time, Cindy was crazed. She was an animal out of control.
"Fuck, yes!" she screamed. "Cum in his mother-fucking mouth!" With that,
Roger's balls tightened and his cock expanded one last time. With a grunt, he
began to come. I swallowed as fast as I could. I would not let a drop of his
delicious cum go to waste. I gulped down six shots of his salty seed. I could
feel his hot cum warm my throat as it slid into my belly.

Watching this was too much for Cindy. With a scream, she planted herself onto
her entire hand and began to orgasm. She was actually fisting herself through
her first orgasm of the night. She shuddered involuntarily and her breasts
trembled as wave after wave passed through her.

We slid back into the water, completely drained.

After a few minutes, Cindy announced that she wanted to watch him "fuck me in
the ass." I tried to protest, but all my self-restraint was gone. We slid out
of the tub and quickly dried off. Although I tried to resist, I went along with
Roger and Cindy into Roger's bedroom. Cindy pulled me into tight embrace and
together we tumbled onto Roger's bed. Once I was on the bed, Roger immediately
pull me up onto all fours. I gave up my last bit of resistance. Oh god, I
needed him inside of me.

Roger was behind me and Cindy propped herself up on pillows in front. Her
vagina was inches from my face. "I don't want to miss a thing," she said. She
watched as Roger coated his middle finger with a thick dollop of KY Jelly. Her
eyes widened as he inserted his finger into me. In a slow, twisting motion,
Roger worked his finger completely inside of me.

God, I was so tight and it hurt like hell. After a few minutes, Roger pulled
his finger out. I sighed in relief, but my rest was short-lived. He entered me
with two fingers this time. I grunted as he forced his fingers deep inside. He
began to move his hand. I could feel him coating my insides with the lubricant.
He ran his fingers around the tight ring of muscles encircling my hole. I
moaned loudly as he curled fingers upward and tugged gently on my sphincter
muscles.

Once I was lubed and loosened, Roger pulled his fingers out. I could feel the
heat of his body as he drew me closer and then the first pressure of his cock
against my hole. With one hand on my hip and the other guiding the way, Roger
pulled me back onto the tip of his penis. His head forced my hole even wider.
Pushing forward, Roger continued to enter me, inch by inch. Despite the KY
Jelly and the finger-fucking, I was still really tight and all I could do was
squeal as he forced his way completely inside of me. I felt him lock his hips
against me and knew that our union was complete.

Cindy was entranced. She could not say a word. Her legs were parted around me.
Her clit was swollen and still ruby-red from her earlier self-abuse. Her lips,
stretched by her fisting, were equally red and swollen. I could see the gentle
trickle of her own excitement ooze from deep inside of her. The wet spot on the
sheets continued to spread out from her steaming hot vagina, expanding wider
and wider with her excitement at what she was witnessing.

Still on my hands and knees, I arched my back to better accommodate Roger's
girth and to draw myself closer to Cindy's vagina. I could smell her. As I
reached out, Cindy pushed her hips forward so that I could reach her. She let
out a high pitched cry as I licked her for the first time - first, a small
circle around her anus and then up, across her battered lips, and onto her
clit. She grabbed handfuls of my hair and pulled me in. Her juices were sticky
and sweet. I forced my tongue insider of her, while sucking hard on her swollen
lips. She moaned with ecstasy.

At the same time, Roger picked up the pace. First, he pulled almost completely
out - only the tight ring of my anus clenching the rim of his engorged penis
head holding us together. Then in a fluid motion, he thrust deep inside, this
time much faster. The excitement of the moment had gotten to Roger and soon he
was pumping hard. Each thrust forcing my face deeper inside of Cindy.

After a short while, we changed positions. I slid onto my back and Roger
stepped onto the thick white carpet. He pulled me to the edge of the bed and
pulled my legs onto his shoulders and entered me again. Within seconds, he was
humping me again, as if he had never broken stride. From this standing
position, Roger had leverage and was able to pump into me like a machine.
Meanwhile, Cindy climbed onto of me in the 69 position to get a better look.
From literally inches away, she watched as my sphincter pulled out slightly as
Roger withdrew and then disappeared inside of me as he pushed forward. So
turned on by what she was seeing, Cindy began to grind her vagina against my
face.

By this time, my own cock was aching and purple from neglect, but Cindy
rectified the situation. Obviously, an accomplished cock-sucker in her own
right, Cindy sucked me deep into her throat in one motion. She sucked hard on
me and with one free hand began to gently squeeze my balls, which were now
heavy with cum.

Our love-play hit its peak. Roger was literally slamming deep inside me, each
thrust striking deep inside and sending electric shocks throughout my body.
Meanwhile Cindy continued to grind against my face. As Cindy ground against me,
I forced my own finger, slick with her own juices, into her tight anus. I
tugged at her virgin anal ring of muscles, causing her to convulse and grind
even harder against my open mouth. For my part, I began to hunch my hips up
forcing my cock back and forth in Cindy's throat.

Then, seemingly all at once, I felt Cindy's thighs tighten around my head,
Roger's cock expand and my own balls tighten. In one beautiful moment, we all
came together. Roger made one final thrust and exploded inside of me, coating
my insides with fiery hot cum. I release my own flood, pumping wave after wave
down Cindy's throat. Even Cindy, who later confessed to experiencing her
hardest orgasm ever, had her very first female ejaculation sending spurts of
fluid into my mouth and against my face.

Roger pulled out of me and collapsed onto the bed. Cindy crumpled on top of me.
Still transfixed on the sight of her fantasy come to life, she watched as the
first drops of Roger's cum oozed from my gaping hole. Within minutes, we all
passed out, still covered in sweat and sex.

That was a year and a half ago. Since then the three of us have lived together
as friends and lovers. We now sleep together in that same bed - Roger pressed
tight against me and me pressed tight against Cindy.

This story is part of White_Shadow's_Nasty_Stories.
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