Author's notes: I first published this story on Literotica in April of 2007. It has since been republished on various sites, both with and without my permission. I am the original author of this work and can easily verify this fact if necessary.
This story is a work of pure fiction. All similarities to persons living or dead is purely coincidental.
The Babysitter's Secret: Part 1
The story that I am about to tell you took place on a day that started out
very ordinary, but would end up as the least ordinary day of my life.
Until that particular Winter day, I thought I knew who I was. I was Peter
Fuller - respected educator, devoted husband, loving father. I had never
cheated on my wife, I had never lied to a friend, and I had certainly never
slept with a girl that young before (at least, not since I was eighteen myself). All of that changed within a matter of hours. But you know what? I wouldn't change what happened for the
In 1998, I moved to the small town of Emberton, Rhode Island to take a job
teaching biology and psychology at Emberton High School. I was
twenty-seven years old at the time. My wife Shawna had recently given
birth to our twin c***dren, Nathan and Johanna, and I thought the job would
at least provide a stable source of income. Little did I realize how much
I would enjoy teaching. It really became my calling and, for the last
eight years, it had been the single greatest joy in my life besides my
We had been in Emberton for about four years when I first met Jenny Rove.
She was the daughter of an old friend of mine from high school named Tim
Rove with whom I'd lost touch over the years. Tim and his f****y had
moved to Southwater, the town that bordered Emberton. He had seen my name
in the paper and gotten in touch. Our old friendship had been rekindled
and now we were closer than we'd ever been. Tim and his wife, Cassandra,
had three c***dren. Jenny was the eldest. When I first met her, she was a shy, boyish-looking k** who I always suspected of having a little crush on me.
It wasn't until Jenny was eighteen that she first babysat the twins.
Shawna and I had been wanting a night out alone but we needed someone to
watch the c***dren while we were gone. None of our regular babysitters
were available so Shawna suggested we call Tim and Cassandra to see if
Jenny would be available to sit for us. As it turned out, Jenny had so
much experience watching her own siblings that she was a natural for the
job. My k**s loved her and she loved them. Everything worked out so well
that Jenny became our first choice every time we needed a babysitter.
I never suspected where it would one day lead.
It was a particularly threatening Thursday night in early December when I
called on Jenny for the visit that would change my life forever. Shawna's
mother was performing in a musical put on by a local theater group and my
wife had decided to drive the two hours to watch and support her mother.
The k**s and I would have gone under normal circumstances but the
performance was being given two hours away and the next day was a school
day. I would have to be at work in the morning. There simply wouldn't be enough time. Shawna decided to stay overnight to avoid a late-night drive home so it would be just me and the k**s.
Then I received a last-minute call inviting me to an emergency meeting of
the Teachers' Union to discuss a possible strike. Despite the forbidding
skies, I couldn't just refuse such an important meeting. I couldn't leave
the k**s alone, either. I called Tim and told him the situation.
"Do you think Jenny could come and watch the k**s for a few hours?" I
asked. "I know it's a school night but I'm really in a bind."
"I'm not sure . . ." he said hesitantly.
"Please, Tim," I pleaded. "I don't have any other option."
"Alright," he said after another moment. "Let me go ask her."
I waited nervously. A minute or two later, someone returned to the phone.
It wasn't Tim, though. It was my favorite babysitter. "Hey, Mr. Fuller!"
Jenny said in her bubbly voice.
"Hey k**do," I replied. "So what's the final report?"
"My dad is just getting his boots on and then he's gonna bring me over,"
"That's great, Jenny," I said. "Thanks so much. You're really helping me
"No problem! Oh wait, here he comes. See you in a few!"
I hung up the phone, then told the k**s what was happening tonight. They
were both thrilled that Jenny was coming over and could barely contain
their excitement. Twenty minutes later, the doorbell rang and I opened the
door to find Jenny on the steps outside my house. Her adorable, cherubic
face was haloed by copper red hair and freckles dotted her cheeks and nose.
Her green eyes seemed to dance.
I invited her inside and took her coat. Jenny was wearing a sky blue
angora sweater and a tight pair of blue jeans, both of which seemed
form-fitting to her lithe body. Although Jenny had been boyish when she
was younger, she was downright sexy now. I tried not to think about it,
but I couldn't help but notice how her breasts had grown from non-existent
to a medium C cup in just a few short years. Her face had become more
pretty and feminine. Her hips now had a lady-like curve. Her butt had
formed into a round, heart shape that I couldn't help but stare at as she
walked into the living room to greet the k**s.
"Hey there, you little munchkins!" she cried. The twins threw their arms
around her and Jenny hugged them tightly. She then launched into an
immediate tickle attack that saw Nathan and Johanna rolling on their backs,
laughing madly. I had to smile.
"I'm going now, Jenny," I told her.
"OK, Mr. Fuller!" she called. "Drive safe!"
"Thanks, Jenny," I replied. "Remember, if anything happens, call 9-1-1.
Or if it's not an emergency, just call me or your dad."
"I will. Bye bye!"
"Bye, Jenny. Bye guys."
"Bye, Daddy!" the twins called back in unison.
I cast one last, lingering gaze at Jenny. I was amazed at how she had
transformed from an awkward tomboy into a sexy nymphet who seemed to
virtually ooze hormones. She was on her hands and knees, tickling the k**s
again, and my eyes fixated at her bubble butt. My cock immediately grew
hard in my pants and, for a brief moment, I felt a kind of a****l lust rip
through my body. I suddenly wanted this eighteen year old girl more than
I'd wanted any woman in my life. But the moment passed. I walked out the
door, thankful for the cold, and climbed into my car to begin the drive to
It was already snowing when I arrived at the appointed location for the
meeting. By the time I left, about two hours later, it was coming down pretty heavily. The roads were treacherous as I drove home. In fact, by the time I reached my street, I was slipping and sliding so badly that I decided not to risk going down the driveway because of its steep incline. Instead, I parked on
the street, and gingerly walked down the front lawn to the door.
I opened the door quietly because I knew the k**s were probably asl**p by
now and didn't want to disturb them since their room was right above the
front door. I stepped inside and immediately heard strange noises coming
from the living room. Curious, I walked into the hall and towards the
living room door. When I peeked inside, I got the shock of a lifetime.
On the big screen television was one of the adult DVD's I kept hidden in my
study/office. It was pretty standard fare - a buff man nailing a woman
with fake breasts - and I rarely ever watched it. On the couch on the
opposite side of the room, I caught Jenny with her eyes glued to the
screen. With her left hand, she was fondling her breasts, which were
clearly visible since she had pushed up her sweater and bra. With her
right hand, she was masturbating furiously to the action on screen. That
wasn't the big shock, though.
Instead of her fingers digging eagerly into her pussy, they were wrapped
around a hard, pink cock that was sticking out of her panties.
Suddenly, things seemed to fit into place. I now knew why Jenny had been
such a tomboy when she was younger. I now knew why the Rove f****y had
made such an unexplained move from the other side of the country when Jenny
was younger. The only thing I didn't know was what to do next. In a split
second, I decided to sneak back out of the house without Jenny noticing me,
and then come back inside. This time, I would make a lot of noise and take
my time so that Jenny would know I was back and could cover herself up. I
didn't want to humiliate her if I could avoid it. But it was already too
"Mr. Fuller!" Jenny shrieked. "Jenny, I'm so sorry!" I cried. "I just
walked in a split second ago! I had no idea what you were doing!"
"Please don't be mad!" she replied, now sobbing. She was desperately
trying to stuff her erect penis back into her jeans. Meanwhile, she was
apologizing for what she was doing and pleading with me not to tell her
parents. "I just found it and I didn't think you'd be home so early and
. . . and . . ."
"It's OK," I told her. "I'm not mad at you."
"I'm so sorry, Mr. Fuller . . ."
"It's alright, k**do," I said, trying to calm her. "Just relax. I won't
tell your parents anything, I promise."
At last, Jenny got her dick back into her pants and pulled her sweater back
down to cover her chest. Hesitantly, I walked across the room and sat down
on the couch beside her. I picked up the remote and turned off the porno
movie. Jenny was no longer sobbing, but tears were still running down her
cheeks. Her eyes were red and her face was puffy. She wiped at her nose
"I'm not mad at you, Jenny," I told her. "There's nothing wrong with what
"Did you . . ." she began. "Did you see . . . that I have . . . that I'm
. . ."
"Yes," I admitted.
"This is so embarrassing," she said, sniffling.
"Don't be embarrassed," I said. "It's normal for teenagers to masturbate,
"But most teenage girls don't have dicks!" she exclaimed.
"That's true," I said. "Do you mind if I ask why you have one?"
Jenny hesitated for a moment, then began her story:
So I sat beside Jenny on the couch and listened attentively as she told me
the story of her life, how she had come into this world as a boy but
quickly realized that had been meant to live as a girl all along. As she
described the difficult times she endured as she came to this
self-discovery, she began to cry softly, and I u*********sly put my arm
around her shoulders to comfort her. She leaned against me and I couldn't
avoid noticing how soft and warm her body felt.
Jenny continued with her story, recalling how she had managed to come to
terms with her identity, and how her parents dealt with it. To their
credit, both of them were extremely understanding and concerned for their
soon-to-be daughter. Neither hesitated in making the decision to move to a
new town so that she could begin a new life as a girl without anyone
knowing her past.
"You're an amazing person," I told her with sincerity. "I can't imagine
the kind of courage it took to change your life like that."
"I knew I'd die if I tried to pretend I was a boy at heart any longer," she
said, sniffling away the last of her earlier crying. "This was who I was
meant to be."
"I hope you don't mind me saying this," I said, "but I never would have
suspected you were anything but a gen- . . . what was the word?"
"Right. I never would have suspected you were anything but a genetic girl
in a million years. You honestly look like any other girl. No, not just
any other girl. You're even more beautiful and more sexy than most girls
who were born that way."
"Thanks, that's really sweet," she said as she turned her face up towards
mine. Her whole face seemed lit up by the compliment. "I think you're
really sexy, too."
"Jenny . . ."
"I know you're married and you have k**s and stuff, but sometimes I wish
you didn't so that you and I could be together." I was speechless and
unable to respond. "Do you ever think about me that way? I mean, what it
would be like to be with me?"
"Yes," I finally admitted. "I do sometimes."
Jenny closed her eyes and lifted her face closer to mine. I knew I should
push her away, tell her no, take her home and forget all of this had ever
happened. But feeling this nubile teenager so close to me, knowing how
badly she wanted me, I was powerless to do anything except close my eyes
and lower my face to meet hers. Our lips met in a tender kiss.
Jenny pulled her face away from mine and her eyes flitted open. I smiled
at her and she blushed. Then she reached a hand towards my face and gently
stroked my cheek. Her hand descended down my chest and torso until there
was no question in my mind about where it was going to end up. Her hand
came to rest right on the bulging mass inside my pants, already rock hard
from the feel of Jenny's body and the kiss we had shared.
She began rubbing me through the fabric of my pants until my cock, which I
thought couldn't possibly get harder, felt like it was about to burst
through the zipper. I groaned slightly and Jenny laughed softly. She was
a born tease, I thought.
Well, she wasn't the only one who could tease.
I stretched my arm out over Jenny's and let my fingers rest on her crotch.
Like mine, her erection was straining mightily against the denim of her
jeans. It was a strange thing to be touching another person's penis, I
think now in retrospect, but at the time it seemed totally natural to do.
Jenny wasn't a boy who happened to look like a girl; she was a girl who
happened to have the same equipment as a boy down there - equipment that
suddenly aroused my desire like I never thought it could.
For a while, Jenny and I rubbed each other in silence. Neither of us
wanted to speak, it seemed, for fear of breaking the atmosphere. At last,
I knew we would have to take a step further or else stop entirely and I was
not prepared to finish this yet.
With one hand, I popped the button on Jenny's jeans and unzipped her fly.
My fingers slid under the elastic waistband over her pants and the
reddish-gold pubic hair felt soft and silky against my skin. My hand
continued its expedition until I found her swollen cock. At my first
touch, Jenny's entire body began to tremble and a moan escaped her lips. I
wrapped my fingers around her shaft and began to stroke her gently.
Meanwhile, Jenny's hand had found its way into my underwear as well. At
the touch of her supple fingers, I closed my eyes and allowed the sensation
to overwhelm me.
Again, it seems like a strange thing in retrospect, but at the time I did
not suffer any earth-shaking notions of: "I can't believe this, I'm jerking
someone else off!" or "I can't believe I'm doing this with an eighteen year
old!" It just seemed to fit together so perfectly.
However, it soon reached that point once again where we had to stop or take
a step further. This time, it was Jenny who took the giant leap for the
two of us. She pulled my hand out of her pants and rose gracefully to her
She turned to face me, smiling mischievously, then in one smooth motion
pulled her sweater off over her head. She was now topless except for a
black bra. She reached behind her back, unclasped the bra, and allowed it
to fall away, revealing the most perfectly pair of breasts I had ever seen
in my life. They were lovely, round b-cups with pink nipples the size of a
half-dollar in the center.
She leaned over, grabbed the waist of my pants, and yanked them down to my
ankles. I compliantly lifted my feet so she could pull my pants and boxer
shorts off entirely. Then Jenny knelt down between my legs and pushed my
At first, I thought she was going to give me a blowjob right then but, like
I said, Jenny was a natural tease. She wanted to warm me up a bit more
first. She leaned forward and blew warm breath on the tip of my cock,
causing it to twitch erratically. Then she took a hold of my dick once
again and began to slowly stroke me up and down. She did it so
deliberately that it almost felt painful. I wanted so bad to shoot my load
but I couldn't at this slow pace.
Jenny leaned forward, placing her chest against my crotch, so that my shaft
was directly in between her breasts. She rubbed herself up and down
against my dick, pushing her breasts together on either side of it. This
again she did with deliberate care and slowness.
Finally, after an unknown amount of this exquisite agony, Jenny lowered her
mouth towards my cock. She opened her delicate lips wide and took the head
inside. Her lips sealed around it, then began to gently massage the flesh
as her head bobbed ever so slightly up and down. She worked for a while
just on the head, sucking it and wetting it with her saliva until her spit
was running down my shaft. She paused to lick it up by running her tongue
from the base of my shaft to the very tip, where my precum would form a
tiny, translucent line between my dick and her tongue.
Jenny increased her pace. Soon, she was sucking harder and faster, taking
more of my cock into her mouth each time her head bobbed down. I thought
she might have trouble with all of my eight and a half inches, but Jenny
sucked cock like a pro. She gobbled it voraciously while stroking the
lower part of my shaft with one hand and fondling her own left breasts with
"I'm going to cum," I whispered raggedly. I could barely breathe.
Jenny didn't remove her mouth from my cock, as I thought she might, but
instead looked me dead in the eye. Our gazes locked and held fast while
she continues to suck and stroke me for the final few seconds. At last, I
erupted. Jenny continued to beat furiously with her hand as I pumped shot
after shot of semen into her mouth. Jenny guzzled it all down without any
show of disgust or distaste at all. In fact, she seemed to become hungrier
and hungrier for it with each dose I gave her. By the end, she was sucking
futilely at the head of my cock, trying to coax more from me.
Finally, I began to go limp. Jenny pulled her face away from my crotch and
wiped a tiny spot of her cum off the corner of her mouth.
"Thank you for letting me do that," she said.
"Thank me?" I replied incredulously. "Honey, that was the greatest blowjob
I've ever received. I should be thanking you!"
"It wasn't the best," she said, blushing and looking away.
"It was," I replied. "You're amazing. I get the feeling you've done this
before . . ."
"No," she said plainly.
"Really? How did you get so good?"
"I spent a lot of time imagining what it would be like to suck you off,"
she told me. "Plus I have one myself so I know what feels best."
"That must be it," I said with a laugh.
"It's getting really late," Jenny said. "I wish I could stay longer but my
parents will be expecting me home soon."
"Wow, you're right," I said. "We'd better get dressed and get you home."
I stood up and helped Jenny to her feet. I picked up my boxer shorts and
pulled them over my legs, then picked up my pants and pulled them on as
well. As I searched for my socks, I watched Jenny as she dressed. She
buttoned her jeans first, then found her bra and sweater. Rather than put
the bra on, she stuffed it into her pocket, and pulled the sweater over her
head. She pulled her hair back, tugging it out of the shirt collar, and
let it fall over her shoulders.
Once Jenny and I were both fully dressed and ready to go, we made our way
towards the door. I stepped outside and was immediately hit in the face
with a blast of cold, snowy air. One look into the night told me what the
conditions on the roads would be like. It was suicidal for me to take
Jenny home tonight. She would have to stay over.
"Oh darn," she said with a very sardonic tone. I looked at her and raised
an eyebrow. "You and me. All night. The k**s are asl**p. Your wife is
gone. I'm hornier than I've ever been in my life. I think this is an
answer to my prayers."
"We don't have to do anything else if you . . ." I began.
"Yes, we do!" she exclaimed, laughing. "I'll call my Dad."
Jenny skipped away to the kitchen to call her house. A few moments later,
she asked me to come in, and handed me the telephone. I was nervous
speaking to her father, fearing that Tim somehow psychically knew what I
had just done with his daughter, but he was very understanding of the
situation. He agreed that it was complete reckless to drive and was very
grateful of my offer to let Jenny sl**p "on the pull-out couch."
When I was done, I handed the phone back to Jenny. She said goodnight to
her father, then to her mother, and then hung the phone up on the receiver.
As soon as it was down, she squealed with excitement, and threw her arms
around my neck. We kissed again, but more passionately and intensely than
before. Already, my cock was hard again.
"We just have to keep it down," I said. "We can't wake the twins."
"Those two can sl**p through a fire alarm," Jenny pointed out as she kissed
my face and neck.
"Good point," I remarked, "now let's go upstairs."
I scooped Jenny up and held her in my arms. She laughed and kicked her
feet excitedly as I carried her out of the kitchen. Up the stairs I
carried her into the room that I had shared for years with my wife and was
now about to share with a transsexual teenager. I have to admit that there
was some guilt about my infidelity, but I could not stop now, even if I
I placed Jenny on the bed, then climbed on top of her. I spread hungry
kisses all over her face, then on her neck, and of course on her delectable
lips. Jenny wrapped her arms around my neck and her legs around my waist,
clinging tightly to me. My right hand founds its way to her breast and
began to massage the tender flesh through her sweater. To my surprise,
Jenny pushed my hand away and drew her face from mine.
"What's the matter?" I said, suddenly frightened and disappointed.
"Go into the bathroom for a minute," she told me as she slid out from under
"Why?" I asked.
"Trust me," she said with a smile that let me know our fun was far from
Doing as I was told, I climbed off the bed and walked into the master
bathroom which was attached to the master bedroom. I shut the door and
waited patiently for Jenny to do whatever it was she wanted to do. I heard
movement from inside the room but resisted the urge to put my ear to the
door. I knew Jenny wanted to surprise me.
A minute or two later, Jenny beckoned me back into the room. I opened the
door and stepped into the bedroom to see my eighteen year old babysitter
lying on her side, elbow cocked, head resting in her hand as she faced me.
She was dressed in a black babydoll with black fur trim and a matching pair
of g-string panties. The material was transparent so that I could see her
nipples through the top and, through the panties, her small cock as it
strained against the fabric.
"Holy God . . ." I breathed.
"I always wanted to wear something like this for you," she told me.
"But where did you get it?" I asked.
"It's your wife's," she explained. "I saw it when I came up here one time
to borrow a sweater. I think she must have been saving it for a special
"Well, this is a very special occasion."
"It sure is. Now don't keep me waiting."
I jumped on top of her and at once we were passionately kissing. She put
her arms around my neck, pulling my face closer to hers, kissing me with a
ferocity brought on by teenage lust. I was actually a little surprised
since, back when I was younger, girls her age weren't nearly so into sex.
Maybe it was the change in the social climate but more likely it was simply
that Jenny might be a teenage girl, but she had the sex drive of a teenage
boy and that's a f***e that's nearly impossible to resist.
I kissed Jenny's freckled face, then worked my way down to her neck and
throat. I planted hot kisses all over the tender flesh before proceeding
down to her collarbone. I kissed the bare skin of her shoulders, breathing
in the clean, pure scent of her skin. Before long, my hands were on her
breasts, and my mouth was on her nipple. It was poking through the flimsy
material of her lingerie and I licked and sucked the fabric eagerly.
Jenny wasn't satisfied with this so she unhooked the straps of the babydoll
and pulled the garment down to expose her perky, teenage tits. I wanted no
time and practically devoured the supple flesh. Her pale pink nipples were
hard as tiny pebbles between my lips. All the while I nursed and teased
Jenny's breasts, her hand was buried down between her legs as she rubbed
the palm of her hand up and down the shaft of her little, girly cock.
Unless you've ever touched or sucked the breasts of an eighteen year old
girl, you can only imagine how tender and soft they feel. True, Jenny
wasn't like other teenagers, but in this attribute she was all girl. I
kissed and licked every inch of Jenny's tits while she sighed and cooed her
enjoyment of the experience. I remembered her fondling her breasts while
she jerked herself off so I made sure to keep at least one hand on a breast
at all times. Every time I pinched a nipple, Jenny's frame shivered and
she sucked in breath.
"You really love having your nipples teased, don't you?" I asked.
"Mmm, yes," she replied.
"Maybe I could do a little more. Just let me know if it hurts."
I placed my lips over Jenny's left breast and kissed her pale, pink nipple
lovingly. Then I parted my teeth and placed them gently around the tip,
adding no pressure just yet. Jenny put a hand on the back of my head and
caressed my hair. I closed my teeth just a millimeter and Jenny's body
shook with delight and she dug her nails into my scalp.
I bit down again - harder this time - and Jenny's back arched, bringing her
chest closer to my face. She yelped in a mix of pain and pleasure. I
pressed my teeth into her nipple with a little more pressure and she was
soon panting wildly.
"Does it hurt?" I asked.
"Yes," she said. "Do it harder."
Who was I to refuse? I clamped my teeth firmly around Jenny's nipple and
she quickly covered her mouth with her hand to stifle a small scream. I
didn't relent and Jenny didn't mind. I bit and chewed her nipple for a bit
longer until Jenny's reactions seemed to be diminishing, then I moved on to
the other one. The entire process began anew and Jenny loved every second
After I'd tormented her nipples for a good while, I decided it was time to
move on from her breasts. I was nervous, I'll admit, but Jenny had done it
for me. Besides, I had come this far. It's not as if I had anything left
I kissed my way from Jenny's tit to her sternum, then down her flat tummy
to her belly button. Soon only a thin layer of fabric lay between my mouth
and Jenny's penis. It was clearly visible through the flimsy material and
I took a moment to admire it. There was nothing intimidating about it.
Even questions I felt about my own sexuality were immediately erased when I
looked at the girl this dick belonged to. She was as feminine a girl as
I'd ever met.
"You don't have to do anything to it if you don't want," Jenny said.
"You sound disappointed," I replied.
"I just mean that I understand if it's too gross for you."
"It's not gross at all. I think it's beautiful. Just like you. But this
is so new tome."
"You don't have to."
"It's OK, honey. I want to."
I wasn't surprised at all to discover that I truly meant it. I was going
to suck this girl's cock and I wanted to do it. I kissed the tip through
the material of the g-string and Jenny trembled and moaned. Her cock
immediately stiffened, pulling on the material. I kissed down from the tip
to the bottom of her shaft and it got harder each time my lips brushed it.
When I reached her nutsack, I noticed that little flaps of skin were
sticking out on either side of the g-string in a way that was somehow cute
At last, I was ready for the real thing. I hooked my finger under the
g-string and pulled the material aside. Jenny's balls flopped free and her
dick sprung to full attention. She held her breath, perhaps waiting to see
if I would really go through with it.
She didn't have to wait long. Without a second thought, I wrapped my lips
around the head of her cock and held it in my mouth. It was warm and
meaty. I touched it with my tongue and tasted salty precum. My tongue
explored the underside of her cock head and found it smooth and delicious.
I opened my mouth wider and took another inch into my mouth. I could feel
the bl**d pulsing through her small prick and imagined that her heart must
be pounding as hard as mine. I looked up at Jenny and saw her watching me
with the tip of her pinky finger in the corner of her mouth. Her breasts
were rising and falling as she breathed heavily. I reached out and took
her hand in mine.
With that, I began giving the girl her first blowjob. At first, I just
tried to do it fast, like I saw women doing to guys in porno movies. After
a minute, though, I realized this was stupid. Like Jenny had said earlier,
I had one myself so I knew what felt best. I liked it slow and deep and I
hoped Jenny would to.
I took all of Jenny's cock in my mouth. It wasn't very big, so it wasn't
difficult to lower my face until my chin was against her balls and my nose
in her auburn pubic hair. I closed my lips tightly around her shaft and
began slowly bobbing up and down.
Jenny's response was immediate. Her body began to writhe and twist beneath
me, as if she were trying to find a more comfortable position, but
couldn't. Her fingers tightened desperately around mine and I squeezed
back hard to reassure her. I could only imagine the rush of emotions that
was hitting her, not to mention the hormone overload. I remembered my
first blowjob as an eighteen year old and thought she must be feeling a lot
of the things I felt - although the circumstances were quite different.
With my free hand, I cupped the side of Jenny's thigh, and rubbed it up and
down. With Jenny's free hand, she toyed with her breasts. We soon fell
into an easy and natural rhythm. Jenny moaned and sighed and gasped the
entire time, although she was always careful to keep the volume low.
I wasn't keeping track of the time but I know it wasn't long before Jenny
began to approach orgasm. After all, she'd been highly charged for hours
now and hadn't had any chance for release. I didn't back down but sucked
even harder and deeper. Jenny would thrust her hips up as I lowered my
head. I took my hand from hers and cupped her ass with both hands. As
Jenny thrust, I pushed her up until her cock was as deep in my throat was
it could get.
"I'm going to cum," Jenny said. She was sweaty and her face flushed. I
didn't reply but kept on sucking. "Are you sure you want to?" she asked,
divining my intentions. I only nodded and kept sucking.
Moments later, the deluge came. Jenny gave a shuddering sigh and my mouth
was suddenly filled with a creamy, gooey liquid. She sighed again and more
pumped into my waiting mouth. I swallowed it down quickly but I could
still feel the strange taste coating my tongue. A few more squirts
followed as Jenny emptied the last of her seed into me. I drank every last
Jenny's body relaxed. Her cock went limp and slid out of my mouth. I
crawled up to lay beside her. For a moment, Jenny just lay on her back,
staring at the ceiling. Finally, she rolled over towards me, nuzzling her
head against my shoulder.
"Thank you," she said. "That was unbelievable."
"It was unbelievable for me, too," I told her.
"Are you sure you've never done that before?" she asked.
"Beginners' luck," I said. "I guess we both have it."
Jenny laughed at that and nuzzled closer. I put my arm around her and held
her tightly against me. While I lay there, holding this sexy, teenage
transsexual and with the taste of her semen still fresh in my mouth, I
thought about all the other sexual experiences of my life, wondering if any
could compare. The only thing that came to mind was my wedding night, when
I was so rapturously in love that every physical sensation felt matched by
an equally powerful emotional one.
But that thought made me feel guilty, thinking about my wife. I knew I had
come back too far to turn back, even if I wanted to, so I pushed the guilt
away. I would have time to hate myself tomorrow but I was going to enjoy
tonight no matter what cost I would have to pay in the morning.
Jenny was quiet. She hadn't stirred or said anything in a while so I
thought she might have fallen asl**p. I was about to wake her up, to have
her move down to the couch as I knew she eventually must, when she spoke.
"I need to feel you inside me," she said.
I swallowed. "You want me to enter you, then?" I asked.
"I need you to," she emphasized. She opened her eyes and looked at me
fiercely. "I need you to make me feel like a complete woman for the first
time in my life."
There was no way I could refuse. "Of course, angel."
Jenny extracted her body from mine and moved into a doggy-style position.
I made a vague comment about finding some condoms but Jenny stopped me
before I could complete the thought. She wanted my cock in her butt with
nothing in between.
I moved to a kneeling position behind Jenny. She reached back with one
hand and hooked the band of her g-string and pulled it down to mid-thigh,
exposing her firm, healthy ass to me in all its loveliness. I reached out
and gently caressed her cheeks with my hands. Her butt was milky white
with a sprinkling of freckles across it - absolutely beautiful.
I spit a puddle of saliva into my hand and rubbed it over my dick. I did
this repeatedly until I had no more saliva left. Once I felt certain I was
as well-lubricated as I was going to get, I shuffled forward on my knees,
bringing myself closer.
I spread Jenny's cheeks apart. Her tiny, pink butthole looked like a
glorious treasure that only I could claim. I ran my slippery wet cock up
and down the crack of Jenny's ass and she breathed airily as the tip
brushed against her expectant opening. It almost seemed to dilate
slightly, as if opening itself to me. My cock was now rock hard and I
resisted every urge to simply slam it inside her.
Instead, I pressed the tip against the hole, and gently pushed. I met with
resistance and didn't penetrate at all. I tried harder and Jenny cried out
"Maybe we shouldn't," I said.
"No," she replied firmly. "Don't stop no matter what."
"OK . . ." I said dubiously.
I pushed hard again. Jenny cried out but quickly buried her face in the
pillow, stifling the noises she made. I suspected that it was not so much
discretion about the c***dren hearing, but fear that I would refuse if I
thought I was hurting her too much.
Finally, her butthole began to yield, and the cock slipped in. With that
progress made, I pushed harder. I felt Jenny's body shake as she began to
cry softly, the sound still muffled. I didn't stop, though. I kept
pushing until my cock was past her sphincter. At that point, all
resistance ended, and my shaft slid effortlessly deeper into her body.
When I was about six inches in, I stopped. Jenny lifted her head from the
pillow and looked back at me. Her face was wet but she smiled at me.
"Make a woman out of me, please, Peter," she said. I pushed my cock
farther in, wondering if her small body could take all of it in. To my
happy surprise, the rest entered without a problem. Once I was in up to
the hilt, Jenny let out a long breath.
Now it was truly time for me to turn this sweet girl into a woman. Placing
my hands on Jenny's hips, I pushed her forward gently and watched as inch
by inch of my dick appeared from between her tender cheeks. Once I was
about half way out, I pushed back in again. Jenny grunted but I continued
This became our rhythm for the first ten minutes or so. I would pull her
towards me, letting my rod slide slowly into her, then I would push her
away, letting it slide slowly out. I could feel the tight muscles inside
Jenny's bowels loosening, which was a good thing. I couldn't begin to
really fuck her until I knew she was in no danger of any serious damage.
Jenny's body movement gave me the indicator I needed that it was time to
proceed faster. As I pushed, she pulled herself. As I pulled, she pushed
herself. Soon, she was pulling faster than I was pushing, and pushing
faster than I was pulling. Effectively, she was fucking my dick with her
ass, rather than the other way around. I began increasing my pace to match
her. My dick was soon moving in and out effortlessly, although it was
still deliciously tight in there.
As the minutes floated by, our tempo increased to a steady, rapid pace. In
and out, in and out, I pushed my cock in and pulled it out. Soon, my
conscious will no longer mattered, and my body was acting of its own
accord. Jenny's body too seemed to be acting without instruction.
Our perfect love-making continued for an unknown amount of time. My thighs
slapped against her ass and my balls bounced against hers with each
successive thrust until the room was full of the smacking sounds of our
frenzied passion and the air began to stink of sweat and other smells which
might have been unpleasant at other times, but not at all right now. I was
at last truly slamming my cock into her ass as I had been aching to do from
I looked up and down Jenny's body. Her babydoll had bunched around her
chest so I could see the smooth, white skin of her back. I leaned forward
and kissed the back of her neck without breaking my stride, so to speak.
Jenny turned her head and tried to kiss me, but couldn't quite reach. I
knew what had to be done.
I slowed my pace until we had both stopped, then reluctantly withdrew my
cock from her asshole with a sucking noise. I took Jenny by the thighs and
flipped her over on to her back with one movement. She bounced on the
mattress and giggled c***dishly.
"I want to see your face while we make love," I told her.
"We can kiss this way too," she said.
"That's right," I said. "It will be so nice to be able to . . ."
"Less talk, more cock," she said, cutting me off.
"As Her Majesty commands," I said.
Jenny was flat on her back with her knees up. I moved into a kneeling
position between her legs. Placing my hands under her knees, I lifted her
butt slightly off the mattress. I leaned my weight forward to keep her in
that position. I peeled off Jenny's g-string and tossed it aside. She
reached down to cup her balls and hold them out of the way while I
renegotiated my way back into her steaming hot bowels.
It didn't take long. Her hole was plenty loose now. My dick entered
without a problem and soon we were back to our old pace. The sounds of
humping filled the room once again. I admired Jenny's taut body, my eyes
wandering from her breasts down to her crotch. Her two little balls were
bouncing up and down each time I railed her and her cock slapping against
her pubic hair.
I gazed into Jenny's beautiful eyes, then leaned forward and kissed her on
the mouth. Jenny put both arms around my neck and held me there tightly.
Our tongues wrestled and fought inside our mouths while my cock plunged
inside her ass over and over again.
Jenny lowered her head back down to the mattress and raised myself back up.
She reached down and took a hold of her wildly-flapping girlcock. She
began jerking herself off almost as hard as I was fucking her. The sight
of this sexy nymphet stroking her dick, and the intense look of a****l lust
twisting her face, made my testicles begin to churn. It wouldn't be long
As I was drawing closer to my orgasm, Jenny began to pant heavily and she
pulled on her dick was hard, slowly strokes. Her body stiffened, then
relaxed, stiffened, then relaxed. At last, a white stream of hot semen
spurted out of the tip of her cock and splashed across her belly with one
glob even landing square between her tits. She continued pumping it and
more came out. I couldn't believe she had so much left in her after all
she'd given me to drink.
It was irrelevant to me, though. The sight of Jenny blowing her load was
enough to push me past my threshold. I pounding her ass furiously, feeling
my climax building. Finally, after agonizing seconds of waiting, I felt
the dam burst. I jettisoned my cum into her body, as deep as my thrusting
cock could go. Jenny gave a satisfied sigh as she felt the liquid oozing
into her. I didn't stop until every last drop was expelled and my cock
could no longer remain hard.
Sadly, I withdrew, until Jenny and I were once again two separate beings.
Soon, Jenny and I would step into the shower to clean ourselves off before
going to bed. Soon, Jenny would get dressed back in her normal clothes and
head downstairs for the night, as we both knew she must . . . just in case.
Soon, I would crawl into bed, alone, and wish Jenny was there with me, her
little cock poking against my leg as she snuggled against me.
That would all come soon. For now, I was content just to hold her close to
me. This girl, who only hours ago had been no more than a babysitter, was
now my lover and I knew would be my lover for as long as she wanted to. I
had known her for years but, in one night, she had changed my life.
"I love you, Peter," she said sl**pily.
"I love you too, angel," I told her, and kissed her on the forehead.
I did love her. What that would mean for the two of us, for my life, for
my f****y, I could only speculate. But now was not the time. I closed my
eyes, drew in her smell, and was content.
Posted by Desangel 3 years ago Views: