Date: Sun, 28 Aug 2005 14:16:22 -0400
From: Desolation Angel <desolation_angel_722@hotmail.com>
Subject: Rebecca's Secret - Chapter 3 for Transsexual, Shemale

Synopsis: This story is the third part of the "Rebecca's Secret" series,
about a young man and his girlfriend, Rebecca, vacationing with a few
friends in a house over the summer.  On their first night alone together,
he discovers that his girlfriend is more than she appears she seems.  She
is a transsexual, born as a boy, but living as a girl for years.  He finds
himself surprisingly turned-on by this discovery and the two lovers begin
the most exciting and pleasurable night of their lives.  Just as they are
about to go to bed, however, they realize that Rebecca's secret has been
discovered by another housemate . . .

* * *

Kate stood before me, dressed in only a burgundy bathrobe, with her back to
the door.  She looked up at me as if waiting for me to say something, as if
I was the one who needed to provide an explanation.  Rebecca, meanwhile,
stood behind me, using my body to shield her from Kate's eyes, not that it
made a difference now.  Kate had plenty of time to see all there was to
see.

"What are you doing here?" I asked sternly.

"Well, I . . ." she hesitated.

"I'm already pissed off, Kate," I told her.  "Unless you want to get
seriously angry, you'd better explain yourself."

"I'm going to get dressed," Rebecca said behind me.

"No!" Kate suddenly said, stepping forward.  "I'm sorry.  It's not fair
that you should have to get dressed on my account.  Here . . ."

With that, Kate untied the knot of her bathrobe, and slowly parted the
fabric, revealing a length of white skin from her neck, between her
breasts, down to the reddish-gold swath of pubic hair between her legs.
She pulled the material over her shoulders and let the entire bathrobe fall
to the floor.  Now she stood naked before us, allowing us to appraise her.

There was no denying that Kate was a beautiful girl.  Even though she had a
curvy, voluptuous body, there was no man I knew who didn't think she was
sexy as hell, despite not being thin.  Her auburn hair, white skin, and
smattering of freckles made her even prettier.  She was nearly the opposite
of Rebecca, who was dark-haired and tiny in stature, with small breasts and
a skinny body.  To me, they were both equally gorgeous, just in different
ways.

"There," Kate finally said, "now we're all on equal ground."

"Great," I replied unenthusiastically.  "Now please tell us what you're
doing in here and why."

"OK," she said, after taking a long breath.  "The truth is this: I am
bisexual.  I've liked boys and girls as long as I can remember and I had
crushed on both of you before you even started going out.  I was a bit
jealous at first when you two started dating but mostly I just fantasized
about having a three-way with you."

"Really?" Rebecca asked, poking her head out from behind me.  I was about
to ask the same thing.

"Yeah," Kate said, blushing a little.  "I always wanted to suggest it but I
didn't know how to, you know?  Anyway, I was the last person to go to bed
tonight, but I could hear noise coming from your room, so I eavesdropped.
I know it was wrong but I was just curious."

"What did you hear?" I asked.

"Enough to know Rebecca's secret," she said.

I looked down at Rebecca, who looked up at me, probably wondering what to
do next.  At last, she bit her lip, and stepped out from behind me.  She
was completely exposed now.  I saw Kate's eyes wander up and down Rebecca's
body with a gleaming kind of hunger.  Kate had been thinking about the
sight of Rebecca nude for a long time, apparently, and now she was
relishing seeing it in the flesh.

"It's true, I'm a transsexual," my girlfriend said.  "I have a penis.  But
I don't think that makes me any less of a woman than you."

"I don't think so either!" Kate replied quickly.  "In fact, now that I see
it, I think it makes you even more beautiful.  You have a very sexy cock."
Now Rebecca blushed.

"Thank you."

"You do too Jordan, by the way," she said to me.

"Thanks for noticing," I replied.  "So what now?"

"Well," she said, "now I want what I've always wanted.  I was hoping that
you two are already worked up that maybe you wouldn't mind inviting a third
into the mix."

So Kate wanted a m‚nage tois with Rebecca and me.  I kept my mouth tightly
shut.  Of course I've thought about the idea of having sex with Rebecca and
another girl, even Kate once or twice, but not so badly that I was going to
risk insulting Rebecca by accepting Kate's offer and implying that she
wasn't enough for me.  If anyone was going to accept this offer, it was
going to be Rebecca.

"What do you think?" she asked me.

"It's your choice, sweetie," I replied.

Rebecca thought for a moment, then stepped past me, towards Kate.  She
reached out and took Kate's hand in hers.  With that, she led her over to
the bed.  Kate had her answer.

* * *

Kate and Rebecca climbed on to the bed.  Kate sat in the middle while
Rebecca sat to her left.  Rebecca indicated that I should come and sit on
Kate's right, which I obligingly did.  Now the three of us were sitting
side-by-side in bed, shoulders touching, each wondering how exactly to
proceed.

It was Rebecca who got things moving.  She put her arm around Kate's
shoulders and raised her mouth to Kate's.  The two girls closed their eyes
as their lips met.  My dick, already getting hard, sprang to immediate
attention as these two pretty girls began to kiss right in front of me.  A
moment later, their lips parted, and I could see the tips of their tongues
touching together.

As they kissed, Rebecca's hand free hand reached out, and placed itself on
Kate's stomach.  As the kissing intensified between the two of them, she
began rubbing the soft flesh of Kate's belly, slowly working her way up to
Kate's D-cup breasts.  At last, Rebecca began to massage Kate's right
breast.  Kate moaned slightly between kisses.  Looking over at Rebecca, I
realized then that I wasn't the only one with a hard-on.

"Your turn," Rebecca said to me, after breaking the kiss.

Kate turned to me without opening her eyes and I leaned in to kiss her.
Her lips were soft and warm against mine and it wasn't long before I felt
her probing tongue.  Kissing her wasn't like kissing Rebecca, though.  This
was an act of pure lust without the emotional impact of kissing the woman I
loved.  Still, I enjoyed it thoroughly.

At one point, I opened my eyes to see what Rebecca was doing, and saw that
she had scooted down until she was eye-level with Kate's left breast.  She
hefted it in her small hand, bringing the nipple closer to her face.  She
popped it into her mouth and began to suck.  I could feel a burst of Kate's
breath into my mouth as she sighed at the added sensation.

We continued kissing.  I rested my hand on Kate's meaty thigh and before
long I was running my hand up and down its length.  My entire body was
reacting not only to the pleasure of kissing Kate, but also to the sight of
my pretty girlfriend voraciously sucking on her friend's tit.

Kate's arm curled around my head and I could feel her palm against the back
of my skull.  She gently pushed my head down, away from her face, towards
her right breast.  I kissed Kate's neck and shoulders on my way down until
the nipple was directly in front of me.  I looked over at Rebecca, who was
smiling at me with Kate's nipple between her teeth.  I smiled back and
began to suckle Kate gently.

By this point, Kate had an arm around each of us, holding us to her breasts
in a motherly fashion.  What was not motherly, however, was the expression
of pure rapture on her face as her breasts were licked, kissed, bitten, and
sucked.

But Rebecca had even more in store for Kate.  She slid her hand down from
Kate's breast, over her belly-button, and through her pubic hair until her
fingers reached Kate's pussy.  From Kate's reaction, Rebecca had no trouble
finding her clit, and was doing a good job of massaging it with her
fingers, because Kate's harsh breathing became soft moans which only grew
louder.  Kate was in Heaven, I could tell, getting her tits licked and her
pussy fingered by the two of us.

A moment later, I felt Rebecca's hand on mine, and I opened my eyes.  She
guided my hand down to Kate's crotch and began moving my hand so that now I
was the one fingering Kate's clit.  It seemed to make no difference to
Kate, who continued her blissful vocalizations.  Apparently, I was in
charge of keeping Kate's clit happy, while Rebecca inserted her index
finger into Kate's pussy, then her middle finger as well.

"Where did you learn to do all this?" I whispered to Rebecca, grinning.

"Girl Scouts," she replied with a wink.

* * *

After a while, it seemed Kate was bordering on orgasm, and Rebecca wanted
to slow it down before Kate was completely spent.  Reluctantly, Kate agreed
to move on to something new.  Rebecca explained that we had given Kate
pleasure and now it was time for Kate to return the favor.

Rebecca instructed me to lay on my back with my head on the pillow and
spread my legs.  I did as I was ordered and immediately got rock hard just
realizing that these two beautiful girls were both staring at my naked
cock, both eager to suck it, although for now Rebecca would give the honor
to Kate.  My girlfriend reached out and held the base of my shaft to keep
my cock straight up while Kate moved into position between my legs.  I took
a moment to admire her curvy body, her wide hips, her huge breasts hanging
down proudly from her chest.

Maybe out of slight jealousy, or just a desire to see her man's needs met,
Rebecca put her hand on the back of Kate's head and pushed it down towards
my waiting erection.  Kate reached out to take my prick in her hand but
Rebecca slapped it away.  "Only your mouth," she instructed.  Kate's warm
lips closed around the head of my cock and I sighed.  She ran her wet
tongue all over my throbbing head until the spit was trickling down my
shaft.

Rebecca took her hand off my cock and let it rest on my thigh.  In a way,
that was almost more erotic to me, feeling her soft hand so close to my
painfully erect penis.  It didn't stay there for long, though.  Soon she
reached under Kate's chin and grabbed my sack, hard enough to hurt in the
most pleasurable way possible.  I groaned loudly and began to squirm as she
played with my balls.  Kate now had most of my cock in her mouth and she
was sucking it for all she was worth.  Her hands were planted on the
mattress on either side of my waist and she was on her knees between my
legs.  As per Rebecca's instructions, she only used her mouth to service
me.  I can't tell you how turned on I was by the sight of this chunky
red-head on her hands and knees in front of me.

Rebecca looked at me and smiled.  I guess she could judge by the look on my
face how much I was enjoying myself.  But she was a girl with needs too.
She crawled towards my head and then swung her leg over me, so that she was
sitting on my chest, with her ass pointed at my face.  She scooted back
until her asscrack was right against my chin, then lifted her butt into the
air, and scooted back an inch more.

Her beautiful, round, white ass was right in front of my face and I needed
no prompting.  I immediately stuck out my tongue and began to lick up and
down the length of her asscrack, all the way down to the back of her
scrotum,, tasting her sweat and her flesh and litte of my own semen.  I
found her hole and began to lick a circle around it with my tongue, then
attempt to probe inside.  I was filled with the desire to get my tongue as
far into her ass as I could.  She moaned as I tongue-fucked her ass.

Then Rebecca leaned forward until we were in a 69 position.  From my
vantage point, I couldn't tell what she was doing at first, but suddenly I
was feeling two tongues licking at the shaft of my cock.  If I hadn't blown
my load so recently, I would have erupted right then.  Feeling those two
hot, wet tongues sliding up and down my cock and over my balls was one of
the most intense experiences of my life.  Occasionally they would pause so
Kate could take me into her mouth, suck me for a few moments, then pass me
off to Rebecca, who would do the same.  I channeled all the sexual energy
that was building inside me into eating Rebecca's butt.

Eventually, when I was only minutes from an orgasm, Rebecca sat back.
Because of her position before, she was now literally sitting on my face.
Before she could smother me (as if I would have cared!  If I had to go
sometime, I'd want it to be that moment), Rebecca climbed off.  Kate
stopped sucking me and I took a moment to catch my breath.

"I think he liked it," Rebecca said.

"Oh God . . ." was all I could say.

"He tastes so good," Kate remarked.

"I know," said Rebecca.

"What now?" Kate asked.

"I think my girls need some attention," Rebecca said, pointing to her penis
and balls.

"Let's not keep them waiting!" I exclaimed and they both laughed.

Rebecca took up the same position I had just vacated, lying on her back
with her legs spread apart.  Kate and I moved into place, each straddling
one of Rebecca's legs so that we could get our heads close enough to suck
her cock simultaneously.  But we didn't go after her cock just yet.  Kate
began kissing Rebecca's right testicle while I went for the left.  First I
licked every inch I could, my tongue occasionally running over Kate's as
she did likewise.  Then I would pinch the baggy skin of Rebecca's scrotum
between my lips and tug gently at it, eliciting groans from my girlfriend.
Then I would suck her ball into my mouth and put a little pressure on it
with my tongue, just enough to make her hurt the way she had hurt me.  She
loved it.

Finally, I couldn't take it any more, I needed that beautiful girly dick
inside my mouth.  I opened my lips and took every inch inside me.  I closed
my mouth around the hard meat and let the heavenly taste of it coat my
tongue.  I opened my eyes long enough to see that Kate was tonguing the
underside of Rebecca's balls, then I looked over at Rebecca.  Her eyes were
closed and she was pinching her nipples tightly as she squirmed in place.

Kate came up for air and I could tell by her expression that she wanted
Rebecca in her mouth.  I smiled at her, knowing that she must be nervous,
considering how nervous I had been to suck a transsexual girl's cock for my
first time that very night.  At last, Kate took Rebecca's six inches into
her mouth, and I saw Kate's eyes roll back.  She closed her mouth and began
sucking with the same ferocity she had used on me.

I took the time to kiss Rebecca's smooth thighs all the way up to her
pelvis bone, then down to her pubic hair.  I kissed the soft hairs there,
then moved up to her belly button.  I put my tongue inside it and began to
lick.  I dragged my tongue from her belly button up to her breasts, which
she yielded to me without complaint.  I sucked on each of them, first just
the nipple, then taking the whole breast into my mouth.  I did that for
each one, then moved up to Rebecca's face, the most beautiful part of her
body.

"Hey," I whispered.

"Hi, sweetie," she replied.

"I love you," I whispered.

Rebecca pulled my face against hers and kissed me, then whispered into my
ear, "I love you too."

Kate was now moaning loudly.  I looked down and noticed that while she had
been sucking Rebecca off, she had been rubbing her clit as well.  Now she
was close to an orgasm.  Rebecca was too, by the way she squirmed.  I lay
down on the mattress next to Rebecca and she draped her leg over mine.
Kate moved so that she was now straddling Rebecca's and my leg.  She
reached out and began to jerk me off.

I stretched out my arm and put it behind Rebecca's head.  She leaned into
me, then turned her face towards mine.  We closed our eyes and kissed
gently while Kate voraciously sucked Rebecca's cock, then mine, then went
back to Rebecca's.  Whoever she wasn't sucking, she was jerking, and both
of us were coming close to our orgasms.  As it turned out, Rebecca would
reach hers first.

"I'm . . . gonna . . . cum . . ." she panted.

"Shoot it on her face," I instructed.

"O . . .K . . ."

Rebecca finally reached down and seized her cock.  As I watched, she gave
it the final few strokes, and then spewed a geyser of thick, white semen
straight at Kate's smiling face.  It splattered all over Kate's left cheek,
chin, and nose.  Once she was done pumping, Rebecca began to stroke my cock
as I bordered on an orgasm.  Kate moved her face closer, preparing to suck,
but Rebecca was too good.  Before Kate could open her mouth, my own stream
of jizz shot out and splattered the other side of Kate's face.  She laughed
out loud as the warm liquid hit her.

I took a moment to recover as Kate moved to a kneeling position.  When I
opened my eyes, I saw her kneeling there with a hand at her crotch,
masturbating furiously.  Most of her face had a shiny coat of cum on it and
some was dripping down her neck.  Rebecca and I glanced at one another,
then immediately sat forward, and began licking the fresh cum off of Kate's
face.  I ate some of hers and I ate some of mine.  It didn't matter.  We
just slurped until our mouths were full of cum, then French kissed so we
could truly share it all.

Kate's orgasm finally hit and her entire body rocked as she enjoyed
multiple orgasms.  Rebecca and I pulled her close and we shared a three-way
kiss.  Kate's saliva mixed with mine and Rebecca's, which mixed with
Rebecca's and my semen.

At last, Kate's orgasm ended, and she collapsed on to the bed, breathing
deeply.  Rebecca lay back as well.  I took a place in between both of them,
then reached down to grab the blankets which had been bunched at the bottom
of the bed.  I pulled them over and carefully covered my girls with it.
Kate picked her watch up off the floor and set it to 6:00 AM, so she could
sneak back into her room before anyone woke up.  Then, with no prompting at
all, both of them leaned in towards me, snuggling against me for warmth.
Rebecca closed her eyes and was almost immediately asleep.

A few minutes later, Kate spoke, pulling me back from the edge of a dream.

"Are you awake, Jordan?" she asked.

"Yeah," I replied sleepily.  "What's up?"

"I just wanted to thank you for tonight," she said.

"It was my pleasure," I told her.

"And . . . well, I feel kind of stupid saying this . . . but I just want
you to know that I've liked you for a long time," she said.

"Oh?" I asked, surprised.

"Yeah," she said.  "That's what made tonight so special.  And, I know you
like Rebecca very much, but I just wanted you to know that if you and
Rebecca ever, you know . . ."

"I know what you're going to say," I told her, cutting her off.  "You're
going to say that if Rebecca and I break up, then you'd like to go out with
me?"  Kate nodded.  "I'm very flattered, Kate, but that's not going to
happen.  I don't just like Rebecca very much.  I'm in love with her and I
know I'll be in love with her for a very long time.  Maybe the rest of my
life."

Kate thought about that for a minute.

"You're very lucky to have each other," she said, a bit sad.

"Thank you," I said, then added sincerely, "and we're very lucky to have a
friend like you."

Kate smiled and I smiled back, then we had a quick, friendly kiss.  Kate
closed her eyes and snuggled closer to me.  Soon, we were all three fast
asleep.


***

At 6:00 AM, the alarm on Kate's watch began to beep on the night table.  I
woke up to find Kate under my arm with her head on my chest.  I gently
shook her until her eyes fluttered open and she smiled up at me.  I nodded
towards the watch and realization hit her.  She reached for the watch and
turned it off.  She stretched and climbed out of bed.  It was dark in the
room but the sun was beginning to peek in through the curtains.  I had just
enough light to watch Kate's ample rear as she pulled her bathrobe on
around her.

"Same time tomorrow night?" she asked me.

"Of course," I replied.

She leaned over and kissed me on the cheek, then kissed Rebecca (who was
still fast asleep).  She waved goodbye and crept out the door, heading back
to her room.  I turned my body towards Rebecca and felt her nuzzling my
body for warmth.  I closed my eyes once again and quickly slipped into
another dream about my darling shemale girlfriend and the night of ecstasy
we had enjoyed.

Around 10:30 AM, we both woke up and began our day.

Rebecca climbed out of bed and walked into the bathroom.  She approached
the toilet and stood there with her back to me.  Through the gap between
her bare thighs, I could see a stream of yellow piss falling into the bowl.
I leaned on my elbow and watched her as she shook out the last few drops,
then flushed.  Next Rebecca turned to the sink.  She put toothpaste on her
brush and began cleaning her teeth vigorously.  When she turned back to
face me, I could see her penis wagging back and forth as she brushed her
teeth.  Rebecca smiled at me.

"Good morning," she said around the tooth brush.

"Is it morning?" I asked.  "I could have sworn I was still dreaming."

"No cheesy lines allowed," she said.

"Sorry," I said.  "I guess love makes you say stupid things."

Rebecca turned back to face the mirror.  I slipped out from under the
covers and joined her in the bathroom.  I stood behind her and wrapped my
arms around her waist.  I leaned down to kiss her neck.  As I did, I slid
my right hand down into her soft patch of pubic fuzz and played with the
black hairs.  Rebecca spit, then turned her face towards mine.  We kissed
and I could taste her minty toothpaste in my mouth.

Rebecca pulled her lips off mine and smiled at me.  She began rinsing out
her mouth as I turned to the toilet to relieve myself.  A minute later, we
were both done, and she followed me back into the bedroom.  I sat down on
the edge of the bed and pulled her on to my lap.  We kissed again, taking
as much time as we needed to lose ourselves completely.

"I invited Kate to come back tonight," I told her once our tongues finally
parted.

"That's cool," she said.

"I hope you're not jealous, though," I said.  "It was fun with her last
night but . . ."

"But you're in love with me?" she said, smiling.  I blinked in surprise.

"You heard that?" I asked.  Rebecca nodded.

"Hearing you say that was better than all the cheesy lines in the world,"
she told me.  "Thank you."

"You're welcome," I replied.

"There's one more thing, though," she said, biting her lip in a gesture of
nervousness.  "It's something I was going to suggest before Kate walked in.
I didn't want to mention it in front of her because I was afraid it would
put too much pressure on you."

"What is it?" I asked her.

"I was wondering if you'd like to try anal sex," she said after a short
pause.

"What?" I asked.  I was confused.  "We did that last night.  Plenty of it."

"No, dumby," she said.  "I mean with you on bottom."

It got through my thick skull at last.  Rebecca wanted to have sex with me
on bottom, meaning she wanted to put her dick into my ass.  It hadn't even
occured to me until now.  Granted, my understanding of male and female had
been changed literally overnight, but I still believed that the man was the
one who did the penetrating.  Rebecca had opened herself to me and allowed
our bodies to become one, but wasn't that what the woman is supposed to do,
even if she has a cock?

Plus there was the issue of the physical sensation itself.  Rebecca liked
it, but I might not.  Would it hurt?  And what would it do to change my
life?  Could I go into a sports bar and watch the Yankees and drink a few
beers with my male friends, knowing that twenty minutes earlier I'd been
sweating and grunting on my hands and knees with my girlfriend's six inch
penis all the way up my butt?

I was being a complete idiot.  Obviously this was important to Rebecca and,
if I truly loved her, I should at least try it once for her sake.  It
wouldn't make me gay or any less of a man.

"I'm sorry for asking," Rebecca said, blushing.  "I should have known you
wouldn't want to try it."

"Hang on a second," I said, holding her back as she tried to climb off my
lap.  "I didn't say 'no.'  I was just thinking it over."

"You don't have to if you don't want," she said.  "I just wanted to please
you the way you pleased me.  I thought it could be another way for us to
express our love for each other."

"You're absoutely right," I told her.  "You were willing to let me into
your body because you love me.  I'm willing to do the same because I.
Love.  You."

Rebecca wrapped her arms around my neck and kissed me.  I lay back on the
bed, pulling her on top of me.  She straddled my waist with the tip of her
cock brushing my stomach and kissed me fiercely.  When the kiss was over,
she crawled off me, and knelt beside me on the mattress.  She instructed me
to roll over on to my stomach.  I obeyed.  She moved closer so that she was
kneeling directly beside my ass.  She placed her hand on my left butt
cheek.

"Ready?" she asked.

"Let's do it."

***

Rebecca wedged the four fingers of her left hand between my ass cheeks and
spread them apart.  She repositioned her hand and then splayed her fingers
even farther, exposing my hole.  She popped her right ring finger into her
mouth and sucked at it to get it wet, then put it against my anus.  She
rubbed it in a circle, then sucked on her finger again, and continued
rubbing.  She leaned her head closer to my crack and spit, dropping a large
dollop of saliva on my asshole.  She rubbed again, working in the natural
lubrication, so her cock would slide more easily in and out of me.

"I'm just going to tease it a bit with my fingers," she told me
reassuringly.  "I'll let you know before I stick anything in."

"Teasing" was the perfect word to describe what she did.  She rubbed her
thumb against my asshole, occasionally pressing it against the rubberly
orafice, and moving her thumb in a circle.  As she continued the motions, I
could feel myself getting looser.  Each time she massaged my rectum, I
could feel the flesh giving way to her touch, as if my body itself were
becoming more at ease with her fingers probing me.  She would step every
thirty seconds or so to suck on her fingers again.  Lubrication is the key
to good anal sex, she explained.  Trial and error with her dildos had
taught her that lubrication and patience were the main components of a
sufficiently loose butthole.

"Now I'm going to put my pinky finger in," she said.  "You'll barely feel
it."

She sucked her little finger until it was covered with spit, then
positioned it against my asshole.  She was right.  I could barely feel
anything except a strange friction as her wet finger glided into my body.
Once her finger was buried up to the knuckle, she wiggled it in a circle to
stretch out my sphincter.  The sphincter is the part of the colon that
keeps the nasty stuff inside until you're on the toilet but it's also the
reason anal sex hurts so much if done improperly.  Rebecca knew that
loosening up my sphincter was the most important step before relal
penetration.

"Now I'm going to use my middle finger," she said.  "This will feel a
little weird but only for a minute or two.  Just relax and keep breathing."

I gave myself over to her care.  I lowered my face into a pillow as she
slid her pinky out of my butt and soon replaced it with her middle finger.
I felt the friction once again, but also pressure as my sphincter tightened
around her finger.  I followed her instructions.  I kept my breathing
normal and tried to let all the muscles below my waist relax.  Once her
finger was as deep as it could go, she wiggled it around, this time harder
than before.  It hurt at first but, as the muscles become less tense, the
pain subsided.  She began to slowly pull her finger out, about half way,
then push it back in again.  It didn't hurt at all.  Actually, it felt
pretty good.

"Mmmmm . . ." I murmured.

"Feeling OK?" she asked.

"Very OK," I told her.  "I can see why you like this so much."

"I'm going to use two fingers now," she said.  "My middle finger and my
pointer finger.  Just keep still."

She pulled her middle finger out of my butt and popped it into her mouth,
along with her index finger.  She sucked them both for a moment, then went
back to work.  The two fingers glided gently into my anus.  I felt pain
again but ignored it, knowing it would vanish in a few moments.  Once the
fingers were inside, Rebecca spread them as far apart as she could, and
turned her wrist in a half circle.  My sphincter continued to stretch until
the pain was gone and only the pleasant sensation of her fingers rubbing
against my prostate remained.  Then she began slowly pulling the fingers
out and pushing them back in until she met no more resistance from my
sphincter.

It was such a bizarre sensation to have something inserted into my ass.  I
was only used to things going out, not going in.  But, although it was
bizarre, it was pleasurable as well.  I took a deep breath and sighed.
Everything below my waist felt warm and relaxed.  Rebecca's fingers working
inside my colon was the only stimulus my brain was receiving, which suited
me fine.

"You know what's funny?" I asked.

"Hmm?"

"If someone in high school had told me that some day I'd be lying naked on
a bed with you while you shoved your fingers in my butt, I would have
laughed my head off," I said.  Rebecca laughed.

"It's too bad," she said.  "I think we would have enjoyed high school a lot
more."

"Yeah, that's true," I remarked.

"Well, sweetie," she said a moment later.  "I think you're ready.  How do
you feel?"

"Like I'm about to melt," I answered.

"Perfect," she said, slapping me on the ass.  "Now let's pop that cherry."

***

First, Rebecca needed her cock lubed up.  She could have just as easily
spat on her hand and rubbed herself wet, but where's the fun in that?
Instead, she walked over towards my head, on her knees, and presented her
nearly-hard cock for me to suck.  I opened my mouth eagerly as she lay her
slab of meat right on my tongue.  I wrapped my lips around it and sucked it
all the way into my mouth.  The taste immediately triggered my salivatory
glands and I used my tongue to rub my spit all over her six inches.  When
she at last removed it from my mouth, it was dripping with frothy saliva.

She crawled back over to my ass and straddled the backs of my thighs.  I
could feel drops of spit falling on to my ass crack as her cock was poised
to enter me.  She asked me if I was ready.  I told her to hurry up.  With a
laugh, Rebecca leaned forward, and pushed the head of her dick against my
crack.  It slid easily between the two cheeks.  She grabbed her shaft and
guided her beautiful shemale penis towards the entrance to my butt.  I
could feel warm precum leaking out of her pee hole and lubing up my ass.

Rebecca placed her hands on either side of my ribs, almost like a sit up
position, and lowered her crotch towards my waiting ass.  At first, I felt
pressure as her pink head pushed against my rubbery anus.  Eventually, my
body yielded, and she slid smoothly inside me.  My sphincter offered almost
no resistance.  She still moved slowly, however, to make sure I was loose
enough to be fucked.  Finally, she was all the way inside.  Rebecca lay on
my back.  I could feel her hard nipples digging into my skin.  For a
moment, she did not move, except to plant sweet kisses on my back and
shoulders.  I knew she was letting my butt get used to the feeling of a
girl's cock inside it.  I was grateful for her concern, but now that I had
Rebecca's organ deep in my bowels, I wanted her to to fuck me.  No, make
love to me, the way I had made love to her.

"Stop teasing me, baby," I whispered.  "Make a man out of me."

"Does this make you a man?" she asked.

"It makes me more," I replied.  "After all, how many guys have the balls to
let their girlfriends butt fuck them?"

"Right," she said.  "And how many girls have balls at all?"

"One I know of," I said, "and that's all I need."

"Well, since you're so sweet, I guess I'll give you what you want," she
said.

She lifted her pelvis and I could feel her cock sliding out of me.  As it
reached my sphincter, I felt a brief moment of panic, but Rebecca had
cautioned me about this.  Sometimes when the head touches the sphincter on
its way out, it feels like something unpleasant is going to come out with
it, but it's just a sensory illusion.  I didn't have to worry about any
kind of mess.  It was just the nerves in my sphincter reacting to the
friction of the underside of her cock head.

Perhaps sensing my discomfort, Rebecca pushed back in.  I felt her cock
rubbing against my prostate gland and her smooth scrotum pressing against
my ass crack.  Her thighs pressed against my butt cheeks.  She withdraw
again, then pushed back in.  Her pace increased.  Soon her balls were
slapping loudly against my ass with each thrust.  She sucked in breath
through her teeth more and more rapidly.  I thought it would hurt more if
she fucked me harder but each thrust just loosened me up that much more and
I could enjoy the pleasure of having my girl's warm organ deep inside my
bowels more.  It occured to me that Rebecca had been denied last night.
She'd been waiting for hours to get a chance to fuck her loving boyfriend
and now she was in a frenzy.

"How does it feel?" I asked her through grunts of delight.

"Fabulous," she said harshly.  "Your ass is so hot and tight."

"Just be gentle," I said.

"No way in Hell," she replied with a laugh.  "I've fantasized about this
since ninth grade.  I'm going to milk it for everything it's worth."

"I think you're the one getting milked," I told her.

She laughed, then threw her hair back and continued plowing my ass.  Both
of our bodies were slick we sweat and we rubbed together each time she went
in deep enough for our bodies to touch.  Still, I felt she could go deeper.
I pushed myself to my hands and knees.  Rebecca wrapped her arms tightly
around my waist and planted the balls of her feet on the mattress.  I took
a moment to imagine how we must look - a girl barely over five feet fucking
a guy over six feet doggystyle.

Rebecca's breath became ever quicker and she was fucking me like a demon.
I knew her orgasm couldn't be too far off.  Although I could have done this
all day, I knew Rebecca must be dying for release.

"Do it," I told her.  "I want your cum inside me."

"I love you so much, baby," she whispered with a ragged breath.

"I love you too," I said.

Rebecca let out a cry and I fould feel something white hot spurting into my
colon.  She thrust again and I felt a second surge.  She thrust a third
time, deeper and harder than before, and emptied the last of her nut into
me.  I slowly lowered myself back on to the mattress.  Rebecca held on.
She lay on top of me for a good three minutes, trying to catch her breath,
as her penis returned to its normal limp size and slipped out of me.  I
felt empty without it in me, like I was more complete with Rebecca inside
me.

Eventually, Rebecca rolled off me and on to the mattress.  I snuggled in
closer to her.  She put her arms around my head and held my face against
her chest.  She was weeping softly.  I knew it wasn't from sadness, but the
emotions inside her had burst with that orgasm, and it would take a minute
for her to get things back under control.  I held her until then.

"Let's do it again," I said.

Rebecca laughed and kissed me.

"Our friends will think we're dead if we don't come down soon," she pointed
out.

"You're right," I said.  "Besides, there's always tonight."

"Tonight will be even better than last night," she promised.  "And every
night after."

We didn't leave the bedroom immediately.  We lay in the bedroom without
speaking, simply holding one another, feeling the strength and purity of
our love.  Rebecca was my girlfriend, emphasis on the word "girl."  I loved
her as much as any man can love any woman, whether they have a penis or
not.  As I squeezed her close and smelled her hair and felt the lingering
warmth of her seed inside me, I knew my love for her would last forever.

THE END