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Subject: {ASSM} A Jack Valentine Adventure: Jamie's Worth (Pt.2) (M/F, M/f, M/m,  pedo, romance, oral, anal, cheat, cd)
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Jamie's Worth
By Jack Valentine

Copyright 2008 Jack Valentine all rights reserved.
Note: This is the second part of a multi-part post. Please see
"Jamie's Worth Part 1" for story codes and synopsis.

=-=-=-=-=-=-=-=-=-=-=-=-=

Jamie's Worth
By
Jack Valentine



Chapter Three


I was free, or as free as a guy like me could be. The evidence was
destroyed, there was just Jamie's word to incriminate me and I knew
how to take care of that. Trusting young girls to keep a really big
secret like having sex with a teacher was a real risk, but a necessary
one. Making sure they were happy and hopelessly in love was the key,
that and picking a girl not only for her appearance, but much more
importantly for her personality. If you know what you're doing, you
can tell which girls will keep a secret forever. Lonnie could do it
and she would, so long as I never hurt her.

The day would come when she found herself in love with someone else. A
boy closer to her own age and all I had to do was wait for it. In her
mind I'd be broken hearted, maybe even a little jealous, but more than
anything else, I'd be happy for her. That was the important thing:
Rewarding the girl for her maturity, and respecting her desires would
ensure the best possible outcome for both of us. I'd send Lonnie off
with a kiss and a small remembrance, a bracelet maybe, or a ring, and
she'd be happy, so happy. She'd remember me forever and keep the
secret, comparing me with every boy she'd ever date, and usually
finding them wanting, I was sure. I enjoyed that part even more than
the seduction, I think. The breaking up and I was good at it.

The only one who'd ever broken the mold was Amy, but she wasn't like
anyone else anyway and I'd married her to keep our secret safe. She'd
been the proverbial thirteen going on thirty and that was no joke. I
don't think Amy had ever been a child really,

Jamie was a child though and he could keep a secret too, and the boy
was vexing me. I loved girls, yeah, but if I'm to be honest as I've
been, I have to admit I loved what they were, more than who they were.
Like Lonnie. I loved her fourteen year old body. I loved her
personality too; she was smart and funny, and completely adorable with
her soft brown eyes and kinky brown hair. The braces she was so self-
conscious of made her deliciously cute. I knew she'd grow out of it
though and so I knew I wouldn't love her for more than a year or so.
She wouldn't be the same at fifteen.

But Jamie...It wasn't a thirteen year old boy I loved, it was him. I had
no interest in boys before and none now. But he was the one I was
infatuated with and I couldn't see it ending. I was confused and
unsure of what it meant. There wasn't any rationale for it. I told
myself it was because Jamie was a boy, that's what was confounding me.
Would I have felt the same if he were a girl though? I suspected I
would and that just made it worse. I had plans and plots and ideas in
my head, but I didn't know what I was doing, not really.

"Jamie, can you stay after class for a second?" I asked him as the
bell was ringing.

We hadn't really spoken in the few days since I'd visited his home. We
saw each other at school and smiled, and I worried that we were being
obvious, when in fact I knew there was nothing out of the ordinary for
anyone to notice. I was nervous though and so I'd kept some distance
between us and Jamie had been waiting for me, patiently for a boy his
age, but waiting nonetheless and now his blue eyes lit up as he
nodded.

"Hi," he said, standing by my desk as the last of the other kids filed
out for lunch.

"Hi," I smiled back at him, barely able to keep myself from reaching
for his long golden hair. I wanted to stroke it. I'd been wanting him
for two full days. "Hey, I'm picking up that new computer after school
today. Can I bring it over to your house?"

"You want to come over?" he asked and his grin was making my heart
jump into my throat.

"Yeah," I nodded. "Is your mom going to be there?"

"Tonight?" Jamie shook his head. "It's Friday, mostly she goes
someplace."

"Oh, well..." I wasn't surprised. "She leaves you home alone?"

"Yeah," he shrugged. "You can still come over, right?"

"Sure, I just really want to meet your mom too," I said.

"Why?" Jamie narrowed his eyes, maybe worried I was going to tell her
about his dress or something.

"I just don't think it would be good if I came over and she wasn't
there," I said truthfully. "What time does she go out usually?"

"After dinner," Jamie told me. "I dunno, like seven maybe."

"Hmmm, okay. I'll come over early, okay? You can tell her if you
want."

"She's gonna think I'm in trouble," Jamie bit his bottom lip.

"No...Here..." I wrote a note on a piece of paper explaining that I was
going to stop by and drop off a computer for Jamie, an old one I had
just sitting in a closet.

"It's an old one?" Jamie asked, reading the note and I chuckled.

"No, it's new," I smiled. "But she doesn't have to know that, right?
It might make her wonder."

"Okay, yeah," he giggled like a little girl and I took a deep breath.
Fuck, that was sexy.

"So, I'll be over about six, okay?" I asked and the boy nodded.
"Good."

=-=-=-=-=-=-=-=-=-=-=-=-=-=-=

I went shopping after school and not just for a computer. I had to
guess at sizes, but I found a sweet dress that I thought would fit him
nicely. It was blue with pink trim, all satin and lace and rather too
nice just for casual wear, but oh! it was beautiful and with his pale
complexion and blonde hair and those eyes...

I picked out a training bra for him and three pairs of panties in a
package, white, pink, and baby blue like the dress. They had small
bows on the front. Some anklet socks, the sort with lace around the
top and a pair of shoes. Again, I was only guessing, but I'd done this
sort of shopping many times and I was more comfortable buying clothes
for a teenage girl than I was buying my own.

Some cute and inexpensive jewelry, little things like clip on earrings
and a gold necklace with a heart locket. Some bangles and bracelets,
the sort of thing girls his age liked and looked so cute wearing. I
bought some pink lip gloss and a purse, hairbrush and comb set, small
compact mirror with some blush in it. Bobby pins and perfume, a little
body spray. It was fun and my cock was throbbing as I imagined Jamie
using those things, wearing those clothes for me.

It was a good trip to the mall and I was satisfied.

"You must be Jamie's mom," I forced myself to smile at the woman who
opened the door.

"I must be," she gave me a genuine smile. "I'm wearin' her panties."

"Great," I blinked at her. "Well, um, I'm Mr. Valentine, um, Jack...and
I teach math at...

"Valentine?" She was in her late thirties, I supposed, and trying to
look twenty years younger. Too much makeup, too much red coloring in
her hair, too much alcohol and cigarettes and too much...Everything.

"Yeah," I nodded, waiting for it.

"I didn't know it was Valentine's Day!" she giggled and gave me what
she must have imagined was a sexy look. "Can you be my Valentine?"

"I'm my wife's Valentine, actually," I held up my ring finger and she
waved that away.

"She ain't gotta know," the woman laughed. "I'm Paula, you want a
drink?"

She was walking away, leaving the door open so I stepped in after
glancing at my car. I'd left the computer in the back seat and I
wondered briefly it would be okay there.

"No, thanks," I said. "I just wanted to bring a computer by for Jamie.
I had an old one and..."

"That's sweet," she leaned against a dirty kitchen counter. "I was
just getting ready to go out; maybe I'll stay in though."

"Uh, well, I can't stay long," I cleared my throat "Is, uh, Jamie
here?"

"I sent him up the corner for some cigarettes," the woman said. "He'll
be back. You sure you don't want something?"

"No..."

"You can have whatever you want," she was grinning at me, striking a
little pose and I was feeling nauseas. "Anything I got..."

"...That's okay," I said. "Maybe I'll just bring that computer inside
and..."

"Yeah, yeah," the woman waved and she was losing interest, thank God.

Jamie was just returning as I was taking one of the two boxes out of
the back seat. We smiled and said hello and I could tell he wasn't
real happy I'd been here alone with his mom. I think not finding me
fucking her both surprised him a little and pleased him a lot. It
earned me some real gratitude in his big blue eyes and I wondered how
much hell this boy had been put through growing up.

"That's an old computer, huh?" Paula was in the bedroom doorway
looking at us as I showed Jamie how to connect everything.

"It's kinda old," I shrugged. "I never used it for anything and so..."

"Well, I gotta get to my appointment with a certain gentleman," she
smiled and I hid my jealousy well, believe me. "His name's Jack too,
but you can call him Mr. Daniels."

"Uh, right. Well, I should get going then," I told her and Jamie was
frowning at that.

"Can't you stay and show me how to use it and stuff?" Jamie asked me.
"Mr. Valentine can stay a little, right mom?"

"I don't care," she shrugged. "Just don't burn the goddamn house
down."

"No, I should..." I started getting up.

"It's okay," Jamie smiled at me and lowered his voice. "She's gonna
go."

Soon enough the woman did leave and we played with the computer for
about fifteen minutes; until I was satisfied Paula hadn't forgotten
something.

"Hey, uh..." I dug my keys out of my pocket. "There's a couple plastic
bags in the trunk of my car, why don't you go get them, bring them
back here?"

"What's in them?" Jamie wondered, taking my keys.

"A surprise," I grinned at him. "Go on."

"Okay, yeah," he smiled and practically ran in his excitement.

Dressing Jamie was fun.

"You're very pretty," I said, watching him stand in front of me naked.
"Don't hide, don't be shy."

"I'm not," he replied softly, but he was nervous and it was sweet.

His body was light all over, without any birthmarks or scars, just a
few small moles maybe and none of those could hardly be called a
blemish. It just added to his beauty. Jamie was short for his age and
thin, perhaps I liked that the most but I suspected it was due to a
bad diet as much as anything else. How he appeared as a frail angel,
with his blonde hair loose and falling around his pretty face. Even
seeing his small penis, pink and circumcised hanging against his plump
little balls, it was sexy. He was sexy and his tits, those nipples
were wonderful and just as swollen as I remembered. I had him turn
around for me, so I could gaze upon his wonderfully pert ass. It was
perfect to my eyes, as it had to be.

"Put the panties on, the pink ones," I suggested and he nodded
quickly. I watched him open the plastic carefully and unfold them,
stepping in one leg at a time and pulling them up.

"Like this?" Jamie looked down at himself and there was just a faint
bulge, barely noticeable and I smiled.

"Perfect," I said. "Get the bra, I'll help you."

The boy had no idea how to put one on, of course, and I was only to
happy to help him. I stood close behind Jamie, fitting his arms
through the bra and pulling the soft elastic tight so the soft cups
pressed against his tits. I closed the back, the two small hooks, and
adjusted the shoulder straps for him.

"It feels tight," Jamie said.

"Turn around, let me see," I whispered and he was there, a foot away
in his new pink panties and small white bra and I had to kiss him
then.

I pressed my right hand to his breasts, feeling him through the cotton
of his underwear and all the while I explored Jamie's eager mouth with
my tongue. He was holding me as well and it was a lovely kiss, one of
the best I'd ever experienced, and I let him go reluctantly and only
because I wanted to see him in the dress I'd bought him.

The dress was satin, as I mentioned, and a wonderful shade of light
blue that set off Jamie's eyes like magic. It was a good fit too and I
had a real eye for such things. It could have been a little longer
perhaps, but no, it was nice just the way it was. I helped the boy
into it and turned him around so I could close the zipper.

"It's beautiful," Jamie said, over and over, stroking his dress like a
new kitten.

He was trembling with happiness and I imagine that for whatever
reason, Jamie had long dreamed of having clothes just like this. I'd
never been much for the debate on heredity versus environment, but I
believed just then, looking at Jamie and his obvious pleasure, that he
really was a girl inside. Being born with male genitals was just bad
luck and it was another part of the boy's life that I found myself
unhappy with. How much rotten luck did any one person deserve, I
wondered? Not this much and I found that nothing mattered to me so
much as seeing Jamie happy.

"Do you like it?" I asked.

"Yeah," he looked ready to cry and I laughed at that.

"It's okay, you can be happy," I told him. "Put on the socks and
shoes."

"Alright," Jamie agreed and I watched him sitting on his bare
mattress, pulling on the ankle socks and fluffing the lace with a
giggle. He put on the shoes and I was thankful that I erred on the
larger side rather than the smaller. Jamie would grow into them soon
enough and he could wear them now anyway. Little Black Betty's with
silver buckles and half inch heels.

"That's perfect," I nodded with a small sigh. "Can I fix your hair?"

"What are you going to do?"

"Oh, I dunno," I shrugged and I was already brushing it, finding some
of the bobby pins I'd bought.

It was easy to pin his hair back on the sides, so that it fell in
golden tresses behind both ears. It was simple, easy, and effective. I
combed his bangs and promised him I was going to cut them soon, just
to straighten them out, but it wasn't bad. I really wanted to bring
him to a beauty parlor, that would have been something. I applied some
gloss to his lips, just to give them a bit more pink and a soft, moist
appearance which he already possessed in any case. Mostly it was just
fun, like putting on his jewelry. The heart necklace and some little
golden bracelets around his narrow wrist.

"How do I look?" Jamie asked, standing nervously in front of me.

"You're the prettiest girl I've ever seen," I told him and maybe it
was true, maybe not, but at the moment I didn't doubt it.

"I am?" he giggled and I could see his little pink tongue.

"Yeah, you are," I said.

"I'm your girlfriend now, right?" he asked me and I nodded.

"Are you ready to go outside?" I asked with a smile.

"Out...Side?" Jamie widened his eyes. "Where?"

"I don't know," I told him and that was truth. "I don't want to stay
here though."

Jamie looked around and he nodded.

"Me neither," he said.

"I want to kiss you more," I decided and I was making up my mind, as
if I hadn't already.

"Okay," Jamie was smiling shyly, licking his lips and lowering his
eyes.

"Do you know what boyfriends and girlfriends do?" I asked him. "When
they kiss? After they kiss..."

"Are we going to do sex?" Jamie wondered in his sweet sexy voice.

"Have sex? Only if you want to, Jamie," I said.

"I do," Jamie replied quickly. "But I'm...I never did it so, maybe I
don't know how?"

"I'll show you," I promised him. "But not here."

"Yeah, not here," he agreed. "So...Where?"

Room 217 at the Motel 8 out by the airport was a nice enough room and
I was only a little nervous. I'd used this motel before with my
girlfriends and it was reasonably safe. I could get a room and drive
around to the back, entering out of sight and bringing Jamie up that
way. I locked the door behind us and he was shy and compliant, and
even getting him to leave the safety of his house wearing a dress had
been easy. Jamie trusted me completely and I liked that a lot.

We were on the bed, fully clothed and I was kissing the boy again. I
couldn't get enough of his mouth and Jamie was learning quickly. His
small tongue chased mine and I let him lick across my teeth and tickle
my cheeks and the roof of my mouth. He was slow and cautious and so
very sweet. My hands roamed his body through his dress and I felt
Jamie's hands doing the same with me.

Making out with Jamie was every bit as good for me as making out with
any young teenage girl. I really couldn't tell that he was a boy, not
while we were clothed and I was in no hurry to undress him. We'd go at
Jamie's pace, that was the rule. If he didn't like something, or if he
said no for any reason, I'd stop immediately. That was how it had to
be with thirteen year old girls and Jamie wasn't going to be an
exception. We were partners in this, he wasn't some sort of love slave
or sexual plaything. I just wanted to be his teacher.

Jamie was sexy as hell too and after probably half an hour or forty-
five minutes of kissing and touching each other through our clothing,
he was ready to go further. I was hard as a rock and the boy was
rubbing my bulging cock, lightly at first, but then harder as he
realized I wasn't going to stop him. Jamie would suck my tongue,
moaning into my mouth while his small hand massaged the obvious
erection in my trousers.

My own hands were all over the boy as well and Jamie didn't protest at
all when I found his own smaller cock with my fingers. He merely
spread his legs for me, lifting his hips while my hand cupped the
boy's innocent sex through his panties. I squeezed him gently, feeling
the small wet stain growing as Jamie's cock was already getting moist
with precum. He wasn't so different from a girl, not at all. That was
especially true when I pushed my hand lower between Jamie's pale
thighs, so that I could play with the crack of his ass through the
thin cotton. It felt just like a pussy, hot and tight and sweet, and I
was fingering him gently with just his panties to separate my fingers
from his virgin hole.

When I finally opened the back of Jamie's dress it felt like Christmas
and I started all over again, touching his chest and tummy, kissing
his skin. I played with his bra, loving the way it fit his immature
body. I pushed it up, above his tits so I could kiss the boy's
nipples. Jamie gasped softly and his fingers were in my hair as I took
them into my mouth one at a time, sucking them gently at first, giving
him small bits and then harder as they grew stiff beneath my tongue.

"Ummm..." Jamie was nodding and smiling with his eyes closed and I
started giving him a hickey on his left nipple, biting it and chewing
lightly while I sucked.

Several minutes later it was dark as an over-ripe cherry and his tit
was a nicely pointed cone now, a beautiful little girl breast. I did
the same thing with the other one, bruising his pale flesh as I drew
blood hard to the surface. I slipped my right hand under his skirt
while I was doing that and spread the boy's legs, feeling his buttery
smooth thighs part easily so that I could rub his crotch like a little
pussy. I pressed my palm against his cock and balls, finding him stiff
with excitement, and my fingers found his asshole and I loved playing
with him there.

I slipped his panty aside and worked the end of my middle finger
around Jamie's tight puckered anus, forcing the tip against that soft
ring and slowly into him. He was tight and dry and the boy jerked
slightly. I brought my finger to my mouth, pausing my kisses around
his tit just long enough to get my finger wet with saliva. I pushed
harder then, worming my finger inside Jamie's virgin boy pussy,
fingering him like he was a little girl, and he rocked his hips, not
fighting that new experience at all.

"Open my pants," I breathed. "Unzip me."

"Okay," Jamie swallowed thickly and then laughed; giving me a soft
nervous giggle while his fingers worked to free my straining cock.

"Yeah, that's it," I said softly, turning his mouth to mine once more
as the boy's hand went into my boxers.

He touched my cock tentatively, exploring it for a few minutes while
we kissed, but soon he was gripping my manhood tighter and that felt
great. I was still playing with him too, my hand between his thighs
and I massaged Jamie's balls and hard little cock with my palm while I
fingered his tight little ass. It felt just like a pussy, except not
as wet maybe and I was working on that too. His small cock, only an
inch or two longer than my thumb and about that thick, was leaking
precum steadily and I rubbed my fingers over the sensitive head
repeatedly, bringing that wetness to the boy's asshole and working my
middle finger slowly deeper with every little push.

I kissed him hard, still making out with the boy and like all girls
his age, Jamie couldn't get enough kissing. Everything I did to him,
Jamie would try on me. I sucked his tongue gently and then his lips,
nibbling and even biting them because they were so wonderfully soft
and full. I pushed my tongue into his mouth, sliding it in and out
like a cock while I fingered his ass pussy gently, and Jamie closed
his lips around it, sucking my tongue while his delicate hand stroked
my cock blindly. He bit and nibbled at my lips as well, rubbed his
small thumb over my cockhead, and wiggled his ass invitingly, hunching
my hand with his hips like all girls do when their little pussies are
on fire.

We didn't talk very much; we didn't have to, and Jamie sat back
smiling and breathless while I undressed completely. He started
removing his own clothes, but I stopped him with a smile. His dress
was bunched around his waist and his training bra askew and pushed up
his flat chest, above those ripe red titties that were beautifully
swollen from the love bites I'd given them. Jamie's panties were loose
and pulled to the side, exposing his stiff little cock, pink and red
and glistening with precum. Between his pale thighs, the boy's
hairless balls lay just above his asshole, the sexy crack and sweet
pucker that I'd only barely stretched with my finger. Fuck, he was
sexy as hell and I didn't want him to move.

I took off all my clothes and found the small tube of KY Jelly I'd
bought just for him, like everything else that day, and he was
curious, but didn't ask. Jamie was hot and flushed all over, breathing
hard and licking his swollen lips. I lay back down on the bed and held
out my arms, inviting him to join me and Jamie didn't hesitate. We
were lovers now and the boy pushed his body close to mine so that I
could embrace him, his mouth pressing against mine with renewed
urgency and I stroked his back and then his ass while Jamie's hand
found my cock once again. We had a lot more making out to do before we
went too much farther and that was fine with me.

"Do you want me to, um, suck it?" Jamie asked me sometime later and he
was smiling, looking shy and slutty and nervous and sexy all at once.

"Do you want to?" I asked him, pulling his blonde hair from his eyes
and it was a hopeless tangle by then and cute like you wouldn't
believe.

"I think so," he whispered and the boy was holding my cock tightly in
his small fist, jerking me off slowly and at times I'd had to stop him
for fear of cumming.

"Try it then," I smiled. "Give it a kiss first."

"Okay," Jamie giggled softly and my heart was pounding with
excitement, as I'm sure his was.

Jamie slid down my body slowly while I watched him, kissing my chest
and stomach lightly, wanting to do more but still uncertain of
himself. That was the best part for me, one of the reasons I loved
girls Jamie's age, they were so innocent and shy at first, wanting to
try new things and desperate to please me and afraid of doing
something that they perhaps shouldn't. The first time was always the
best and seeing Jamie kneel over my erect cock, holding it now with
both hands and staring at it with every emotion imaginable crossing
his pretty face, was almost unbearable for me.

"Take your time, Jamie," I said, contrary to everything I was feeling
just then. "You can do whatever you want. You're beautiful. I love you
so much."

"I am? You do?" Jamie looked up at me, smiling and looking so hopeful
with those big blue eyes. "I love you too. I want to do it, okay?"

"Yeah," I sighed, staring as the pretty little boy gave the tip of my
cock his first kiss.

A long silvery strand of precum connected my swollen cockhead to
Jamie's lips for a second and even as it broke the boy was coming back
for another. He kissed my cock all over, exploring it slowly with his
closed mouth and finally his tongue once Jamie was used to it. It
didn't taste bad, his smile told me. It was hot and heavy and
throbbing just for him and I told him that. I made sure Jamie
understood that he was the reason my cock was so hard. I reassured him
over and over, enjoying the way he was licking my cock like an ice
cream cone, dragging his tongue along the bottom of the shaft and then
around the head. Jamie was losing his fear and gaining confidence and
it was just a matter of time before he opened his mouth wide and
started sucking my cock like the little girl he was.

"Mmmm...Baby, that's it...That feels so good," I told Jamie, resisting the
urge to hold his head in my hands and fuck that sweet sucking mouth of
his.

He was doing fine by himself anyway, bobbing his mouth up and down on
my aching cock slowly and learning how to suck it nicely for both of
us. He was able to get the smooth head and just an inch or two more
into his mouth before Jamie would gag on it, but that was alright.
He'd figured out how to use that soft little tongue of his and the
sensation of it wriggling around my cock was driving me a little crazy
with lust. I soon had my fingers in his soft blonde air, I couldn't
help it and Jamie was okay, he liked that attention and rewarded me
with shining eyes filled with pleasure. He wanted to take more of me
and he would try every now and again, but the boy's mouth was just too
small and he wasn't ready to try opening his throat for it. I wasn't
going to force him at all. After a few months of practice, Jamie would
get better at it and maybe even learn to deep throat me; that would be
really nice.

"Mpphhh...It's big!" Jamie giggled, pulling his mouth off my cock with a
loud wet sound that made me smile.

"No, not too big," I chuckled, stroking his red cheeks with my fingers
and admiring the way his chin and neck had become wet with spit and
precum. He'd been drooling a lot, giving me a sexy sloppy blowjob and
I really wanted to fuck him now.

I had to be patient though, Jamie wasn't finished and I was a little
surprised when he started kissing my balls, but I shouldn't have been.
This boy was going to be a little cockslut, I thought, much the way
Lonnie was. The way they all were once they got used to it. It was
amazing how quickly a thirteen year old will accept almost anything so
long as it's fun and doesn't hurt. Jamie was licking my scrotum like a
kitten and practically purring as my wet cock slid over his pretty
face. He was sexy as hell like that, giggling and making muffled moans
and sighs. He opened his mouth without any prompting from me and I
nodded happily as the boy took one of my balls into his warm wet
mouth, washing it carefully, rolling it around with his tongue. He did
the other one as well and that was just getting me hotter to break the
boy's cherry.

"I want to make love to you," I whispered, unable to contain my
desires any longer. "Do you want to try that?"

"Yeah," Jamie looked up at me, licking his lips and nodding slowly. "I
want to, but...Will it hurt?"

"A little," I said, because I'd never lie to the boy. "I'll be really
careful though, I promise."

"Okay," Jamie said softly, making my heart ache and cock my throb with
anticipation. He was so beautiful just then, so innocent and trusting
and I did love him.

"Like this...Come here, I have some stuff to make it feel good..." I told
him, moving Jamie so he was laying on his back.

I was going to fuck him like the little girl he was, staring into his
eyes and kissing that sweet mouth of his while I took his cherry.
Jamie smiled and giggled nervously as I pulled his panties off
completely. His smallish cock was so hard it looked almost painful and
I knew he wanted to cum. I thought perhaps he'd been trying to ignore
it, or possibly Jamie had just been afraid that I wouldn't like his
cock because it was proof that he wasn't the girl that he wanted to be
for me. It was only slowly that I realized the boy had never had an
orgasm in his life. Jamie honestly didn't know what to expect and I
shouldn't have been surprised by that, very few of the girls I'd been
with had known anything about sex before I'd taught them. Jamie was no
different.

"You need to cum, don't you?" I asked him and I was getting my fingers
wet with a large dollop of KY Jelly.

"Ummm..." Jamie laughed softly and gave me the tiniest shrug. "I think
so."

"I think so too," I smiled, pushing his legs up so I could spread the
lubricant around his virgin anus. "Have you ever cum before?"

"I don't know," Jamie said seriously. "Maybe."

"If you did, you'd know...How does this feel?" I asked him, rubbing his
tight little asshole with two fingers, getting him slick and ready for
my cock.

"Goooood..." Jamie sighed and he was trying to relax, his sphincter
muscles contracting every few seconds so that I could see his pink
asshole winking at me. It was cute.

"I'm going to get you wet inside too," I told him. "Just relax now,
this will feel nice, okay?"

I worked one finger past the ring of as anus, pushing the jelly into
his asshole as I went. Jamie was tight, incredibly tight and hot
inside. It felt like a virgin pussy though, seriously. His asshole
spasmed around me and Jamie's cock jerked, a large drop of precum
spilling across the pink tip and running down the shaft while I
watched it. He was enjoying my finger in his ass, that was obvious,
and I pulled it out so that I could apply more KY, squirting it onto
Jamie's asshole. I finger fucked the boy like that for a good five
minutes, eventually working a second finger inside and making him gasp
at the sensation of being stretched so gently. I was slow and careful
and comforting with my voice, telling the boy how beautiful he truly
was.

Finally I spread lube all over my own cock, stroking myself with
slippery fingers while I looked down on him. Jamie was waiting
patiently, but he was nervous and a little frightened, his thin body
shaking with anticipation. He wanted me to fuck him, I knew that, and
it was just the newness of it that made him uncertain. I had to make
this good for him, I reminded myself. I wanted Jamie to enjoy it as
much as I would and like all my girls, he'd soon lose his apprehension
and come back for more. We'd fuck a lot over the coming months, I
thought. All I had to do was make the first time really good for him.

"Shhh...Just relax now, it's going to be nice," I whispered, lying atop
the boy with my erection stroking his.

"I know," Jamie said, wanting to believe me and his eyes were staring
into mine as I brushed his hair from his eyes.

Jamie's legs had naturally gone around my waist and he lifted his butt
off the bed, needing to feel more pressure against his horny little
cock and we were kissing again. I explored his now familiar mouth
gently, grinding my cock against his and it was something I'd never
imagined myself doing, making love to a boy, but Jamie was so pretty,
so sexy that I could barely think of him that way.

We kissed for several long minutes, until he seemed relaxed and ready
to let me inside him. I reached down between us, pushing my cock to
his vulnerable ass and I rubbed my slippery cockhead over the boy's
tightly puckered anus. I knew he was as ready as I could make him. I'd
been generous with the lubricant, pushing as much of the jelly into
his tiny rectum as I could, but still I felt a twinge of hesitation. A
pussy was made for cock, even a thirteen year old girl's virgin sex.
They stretched easily, even eagerly once the girl was used to it.
Cunts were made for cock, but Jamie...All I could do was try, there was
no going back now and he wanted it anyway. We both did.

"Ummmm..." Jamie scrunched up his face, the corners of his mouth turning
down as I began to push the head of my cock into his ass.

"Relax, baby. Let me in," I whispered, kissing his face and gripping
his narrow shoulders in my hands.

"It's too big," he breathed, letting out the breath he'd been holding
and that seemed to help as the head of my cock suddenly popped inside
his asshole.

"Oh! There!" I smiled, pausing as the wonderful sensation of his tight
asshole gripped my cockhead like a vise.

"It's in me!" Jamie smiled with some surprise. "It doesn't even hurt."

"Are you sure?" I asked and he nodded.

"It just feels...Big!" he giggled and I took advantage of the moment,
pressing my mouth to his, pushing my tongue between his open lips and
then thrusting hard with my hips, driving slowly into him.

I didn't stab into Jamie, but just gave the boy a constant, steady
pressure to force his tight rectum open for me. My cock inched
forward, burrowing deeper with every passing heartbeat and Jamie's
legs tightened around my waist with the effort of taking his first
cock. I imagined I had to be completely inside the boy, but I wasn't.
I had only half of my cock inside him, just the head and three inches
more maybe, and that was enough for now. I was content to work just
that much in and out of him slowly, breaking our kiss so we could
catch our breath.

"Are you okay? Does it hurt?" I asked Jamie and he shook his head.

"It's okay," he said, but his voice quailed and he was shaking beneath
me. His legs were tight, scissoring me with his ankles in the small of
my back.

"I don't want to hurt you," I told him. "We can stop if you want."

I meant what I was saying too, although at the same time I was moving
my hips, working my cock an inch or two back and forth, fucking the
boy slowly. I'd stop if I had to, but I really didn't want to. His
asshole was tight and hot and wet with lubricant and my own precum. He
felt like the smallest virgin pussy I'd ever had in my life, better
than that even, and it wasn't going to take much to make me cum. A few
minutes of this, just short stroking the boy with half my dick buried
in his rectum would do it. I was going to fill his ass with a big load
of man cream if he'd let me.

"It doesn't hurt," Jamie promised me. "I like it. I love you, Mr.
Valentine."

"Heh," I had to smile at that, but they all called me Mr. Valentine
and I wasn't going to change it. The only one who called me Jack was
my wife and only after I'd married her. It was better that way because
the kids wouldn't forget and slip up at school, but more than that, I
really liked the way it reminded us that I was Jamie's teacher, an
adult, and he was still my student, a child struggling to grow up.

I kissed him again and worked my cock a little faster, going a little
deeper and wondering if I couldn't get every inch of it inside the
boy. That would feel amazingly good, I was sure, and Jamie wasn't
protesting at all. If anything he seemed to want as much as I could
give him. Jamie pulled at me with his legs and his arms were around my
neck, tugging at me there too. He lifted his ass with every thrust,
meeting my cock and trying to help me get deeper. Jamie was learning
how to fuck a cock and the thirteen year old was loving it.

"It's good...I like it..." Jamie whispered, as if reading my mind and that
was when I decided I'd have to fuck him right.

"Lift your legs, Jamie," I told him. "Up like this...Over my shoulders..."

"Oh!" Jamie grinned and his blue eyes got big as I pushed his knees to
his chest.

Jamie's ass rolled off the bed, his cock-stuffed hole turned upward as
I leaned over him, pinning the boy down with his legs trapped by my
arms. He was helpless as a butterfly, vulnerable and wide open to
whatever I wanted to do with him. I had a straight shot into the
depths of his boy cunt and I had to resist the urge to drive my cock
balls deep into his body with one quick thrust.

Instead I just pushed slowly, working my dick in and out with longer
strokes than we'd managed before. This was good and whatever
discomfort Jamie felt, he didn't voice it at all. He just watched my
eyes, smiling and gasping every so often as my cock would stretch him
a little more, opening a part of him that had never been touched
before. I was working his asshole nice and gently, driving my cock
deeper without hurting him in anyway. It was a great fuck, a perfect
fuck and I wished they were all like this.

"Oh ohhh..." Jamie's eyes went wide suddenly and his mouth opened in a
big round O as the head of my cock touched bottom.

"Fuck..." I breathed, swallowing hard as I held myself there, knowing my
swollen cockhead was massaging the boy's immature prostate. He was
shivering at the sensation, a pleasure he'd never imagined and I was
surprised to feel a wetness on my stomach. Jamie had orgasmed in that
moment, his cock was jerking wildly between his thighs, spraying hot
boy cum like a fountain. Some of it reached me, but mostly it was
landing on his own tummy, on the dress that was still bunched up
around his waist.

"That was...It hurt...Kinda..." Jamie looked at me with a confused mix of
pleasure and pain, nothing terrible of course, it was just unexpected
and new.

"You came for me," I smiled at him and lowered my face to kiss his
lips and eyes. "Are you okay?"

"Yeah, I think so," he giggled weakly and I felt his asshole
contracting sweetly around my cock. It had felt especially good during
his orgasm, the boy's rectum seeming to tremble with the effort to
empty his balls.

"I'm going to cum too," I told him. "I want to cum inside you, Jamie.
I want to make love to you now."

"Yeah..." he breathed, smiling like he'd never stop and I kissed him
again.

We fucked after that, the way I'd have fucked any girl's sweet pussy.
I stroked the length of my cock in and out of the boy, gaining speed
as I felt my orgasm drawing closer. He was so incredibly tight, his
asshole clenched around my dick like a fist. Jamie's ass was a perfect
fit for my cock too, when I was all the way inside him, when my sperm
filled balls slapped his ass, the head of my cock was touching bottom,
kissing the pillow of his prostate like we were made for each other.

"Oh fuck!" I groaned after not nearly enough minutes of fucking him. I
gave him one last thrust, jamming my prick as deep inside the boy as I
could and arched my back against my orgasm. My balls drew tight and my
cock seemed to explode with a rush of semen, spurting rapidly into the
depths of Jamie's clasping boy cunt. He was clutching at me, feeling
my cock jerking inside him as a flood of hot man cream filled his ass.
I felt the walls of his rectum squeezing me with little contractions,
the boy squeezing his asshole to milk my balls for every drop he could
get. Jamie was letting me love him and loving me in return.

I held myself there for a long while, both of us enjoying it while we
cooled down and caught our breath. I was panting for air and Jamie was
licking his lips, nodding and telling me with his eyes that it was all
good. He was undoubtedly sore down there, his tender asshole stretched
and the muscles tired from struggling with his first ever fuck. Jamie
was a little high now on adrenaline and endorphins, but he'd feel some
pain later, I was sure of that. He'd fucked me as well as any pussy
I'd ever had though, better than most actually, and only reluctantly
did I finally pull out of him.

"One thing left to do," I told the boy playfully, cradling him in my
arms and stroking his smooth skin.

I'd found the cool stain of his orgasm and played with it, massaging
Jamie's cock and balls with my sticky hand, working his own cum onto
his flushed skin. It had made him hard again while we kissed in the
afterglow of our lovemaking.

"What's that?" he wondered and I was jerking him off slowly, much as
Jamie was doing for me. My own cock hadn't gone very soft at all and
our arms were crossed, both of us moving slowly while we cuddled.

"I'm going to give you a bath," I kissed him. "Make you feel better
before I take you home."

"Do I have to go home?" Jamie asked me, his blue eyes searching mine.
"Can't we stay here?"

"I wish we could," I said seriously. "But it's getting late. You need
to get home before your mom does and I need to get home before my wife
divorces me."

"Oh," Jamie frowned and I kissed him softly.

"We'll do this again, okay?" I said. "We'll do it as much as we can. I
love you, Jamie. I always will."

"Can't I go home with you?" Jamie asked me and I smiled at that.

"I don't think my wife would understand," I told him. "Maybe sometime
you can come to my house, we'll have to wait and see."

"I wish you weren't married," Jamie sighed. "I wish I was your wife."

"I know," I said gently and the idea of bringing Jamie back to that
crappy home his mother had made for the boy didn't make me very
happy.

I bathed Jamie in the tub, washing his body everywhere, especially his
ass. It made him a little self-conscious when I had him get on his
hands and knees for me, spreading his cheeks and inspecting his anus
gently. I'd been very careful with him, but even so he looked red and
puffy down there, swollen from our fuck and bruised possibly, but at
least there weren't any tears in his soft skin. Jamie wasn't bleeding
or anything like that and I was glad. I washed his asshole thoroughly
with soapy fingers and the warm water was soothing, I think.

The hardest part of the whole thing was not giving into the temptation
to fuck him again. My cock was stiff and ready, and Jamie's cock was
swollen with his own arousal. I could withstand my own desires, but as
the boy's bath was finished I realized I couldn't bring him home
without some relief. One orgasm wasn't enough for a healthy boy his
age, especially since it had been his first.

"What are you doing?" Jamie gasped and he was standing in front of me
while I knelt on the bathroom floor and toweled him dry. What
surprised him though was when I leaned forward and took his small cock
into my mouth.

I'd never sucked a cock in my life, never wanted to for that matter,
but Jamie wasn't much of a boy anyway. His cock wasn't large either
and his balls looked sexy and feminine almost, so smooth and pink. He
didn't have a hair on his body except for the top of his head and I
didn't think of it as giving Jamie a blowjob. He was a person I loved
and I wanted to make him feel good, so I took his cock into my mouth,
exploring it with my tongue and there was nothing bad about it.

I took Jamie's ass in my hands as well, squeezing his small round
cheeks and pulling him closer. The boy soon had his hands on my head,
his fingers in my hair, and I heard the soft gasps and low moans
rising from deep in his throat. This was good for him, what Jamie
deserved after being so brave and taking my cock in his virgin ass
like he had. I suckled his sweet little dick gently, washing it and
swallowing the precum and saliva that filled my mouth. I let him move
his hips, like he was fucking my face and I made a tight O of my lips
for him to use.

It was new and fun and my own cock was throbbing with excitement when
Jamie groaned after just three or four minutes. His body went stiff as
he felt the second orgasm of his young life rising from his balls. He
came in a torrent of hot sperm, flooding my mouth and I couldn't hope
to swallow all of it. I'd never given a boy a blowjob in my life and
it surprised me how quickly his sweet cream came out. It was sweet
too, salty but hardly bitter, and I was pleasantly surprised by the
taste. Jamie was sweet and hot and only the texture was strange, but
even that didn't turn me off at all. It was Jamie and I wanted him to
know how much I loved him.

I swallowed as much as I could and scooped the semen that I'd missed
off my chin, sucking my finger clean while Jamie beamed happily. It
was the best part of the night for him and the boy spent the next half
hour telling me how good it had felt cumming in my mouth. I just
smiled and laughed, loving Jamie all the more while we dressed him in
his normal boy clothes from the plastic bag we'd brought. His girl
clothes went into it and Jamie wanted to keep them, to bring them
home, but I told him I'd wash them first.

"You have some new clothes at home anyway," I laughed, meaning just
the other panties I'd bought. "Don't worry, I'll bring these back.
I'll even buy you more, okay?"

"Okay," Jamie agreed and he was frowning at himself in the mirror.

"What's wrong?" I asked him.

"These clothes feel funny now," he said and then giggled with a little
blush. "I wish I didn't have to be a boy anymore."

"I know," I said, turning him around so I could hug and kiss him.
"Just remember, you're not what you wear, okay? You're who you are
inside."

"Yeah," he looked up at me, smiling gratefully because I think he'd
been a little worried I wouldn't like him now that he was a boy again.

"You're going to be okay," I promised. "Do you have a place you can
keep your new clothes?"

"Oh yeah," Jamie grinned. "I got some good hiding places. Mom never
looks anyway."

"Okay," I said. "We just have to be careful, right? I know you can
keep a secret."

"I can," he said. "I won't tell anybody, I promise."

"I know," I kissed his mouth. "That's why I love you, cause I know I
can trust you, Jamie."

"I love you too," he said.


=-=-=-=-=-=-=-=-=-=-=-=-=-=


Epilogue


"Where have you been?" Amy asked and she was waiting up for me like
she always did.

"Missing you," I grinned at her, undressing quickly and I had to fuck
her soon or my balls were going to explode.

"Hey...Ohhhh!" she giggled as I crawled between her legs, pushing her
short nightie up and pulling her virgin white panties down. "What's
gotten into you?"

"Have I told you how much I love you lately?" I grinned at her,
bringing my cock to Amy's pussy and she wasn't very wet, but she'd get
there soon enough.

"Noooo..." she said slowly, sliding down her pillow a little, getting
comfortable beneath me.

"I do," I said softly. "I love you very much, Amy."

I kissed her softly, seeing the girl I'd fucked ten years before on
her pretty pink bed looking up at me. I'd been filling in for her
regular babysitter and by the time the night was over, I'd become
Amy's boyfriend, popping the little girl's cherry while she cried and
made me promise to love her forever. It had been an easy promise to
make, especially while I was stretching her tight little pussy with my
hard nineteen year old cock, but I'd meant it too. I still did and
even though she was older. Too old it seemed sometimes, but Amy was my
wife and I was very happy that she was.

"Ohhh...Ah...Ummm..." she stiffened and winced and then relaxed as I pushed
my cock inside her pussy slowly. Amy was dry, but that was good for me
too, it made her feel like a twelve year old again.

"Sorry," I whispered, not meaning it at all and she laughed at me. Amy
knew me too well.

"Just slow...Hmmm...Good..." Amy held me tight and this was a nice surprise
for her, making love like this, and I made a promise to myself to do
it more often.

The reason, of course, was Jamie. I still had the boy in my head and
the taste of him in my mouth, and I could have fucked the boy all
night long if it were possible. This was good though, fucking my wife
the way a husband should. She knew I'd been with someone else, some
little girl that Amy didn't want to know about. She knew me well
enough, like I say, and that was all that mattered. Amy had never
tried to change me. She knew I had to have my little girls, but...

"What would you think of..." I hesitated, looking for the right words as
I fucked Amy slowly, feeling her pussy still hot and tight, but
growing wet now and taking me easily.

"Think of what?" she asked, lifting her hips and pulling me into her
with her legs around my waist, much as Jamie had done earlier.

"Adopting a kid," I told her.

"Adopting a baby?" Amy smiled and we'd talked about babies before.
"Why don't we just make one of our own?"

"Hmmm?" I grinned at her. "You're still on the pill, right?"

"Yeah, yeah..." She stroked my shoulders with her fingernails. "...But I
could stop. It would be really easy."

I smiled at that, but it was hard. I'd never told Amy that I'd had a
vasectomy. I couldn't very well run around fucking twelve or thirteen
year old girls, trusting them to remember the birth control pills I
bought them. A secret was one thing, but anyone could forget a pill
and I hated condoms. I'd used them as a teenager when I had to, but as
soon as I'd turned eighteen, I'd figured out what I had to do. It had
been a big decision and I'd had my whole life ahead of me, but at the
time I'd never planned on getting married either. Some kids saved up
for cars, or college; I'd saved up for a vasectomy and only sometimes
did I regret that decision.

I hadn't lied to Amy, but I'd never found a way to tell her the truth
either and I was very much regretting that too. The reason she was
taking birth control pills was so I wouldn't have to come out and say
that I wouldn't ever be able to give her the baby she wanted. I was
just putting off the inevitable. Lonnie was the same way. That little
girl wanted to get pregnant and I'd gotten her on the pill not only to
reinforce the idea that she shouldn't, but to protect her too. Lonnie
loved to fuck and I knew it wouldn't be long before another cock found
her barely fourteen year old womb. I was doing her parents a favor,
believe me.

"There's a boy I know, one of my students," I started explaining.
"He's a special kid and..."

"A boy?" Amy stopped moving, searching my face with her eyes, blue
like Jamie's. "You didn't...You fucked him?"

"He's more of a girl than a boy," I said and Amy didn't know whether
to laugh or cry and we were both rather still just then, my hard cock
still buried in her moist cunt.

"Are you gay?" she asked and I laughed at that.

"No, not at all," I said. "I just...He's special. You'd like him."

"I don't want to like him," Amy frowned and I started moving again,
testing her reaction and she didn't object. "Girls are one thing, I
know you love girls, but...A boy, Jack?"

"You should see him in a dress," I grinned at her and that actually
made Amy almost smile. "I swear, he's so sweet. Jamie's like..."

"Jamie?" she rolled her eyes. "That's why you wanted to fuck me in the
ass? So you could pretend I was a boy?"

"What? Come on..." I kissed her frown. "You liked it."

"Yeah," she sighed. "Thanks a lot."

"I'm serious though, Amy," I said, making love to her now, moving my
cock in and out the way she liked it. I wasn't going to fuck her into
changing her mind, I knew that, but every little bit helps and our
relationship was strange anyway.

"Serious about what?" she asked me. "You want to adopt the little boy
you've been fucking? What does that make me?"

"What do you mean?" I asked.

"I mean you're my husband, Jack," Amy said. "I'm your wife and I can
deal with you fucking around, but not if I have to see it. You can't
have both of us."

"You might like him," I said gently, kissing her again and Amy made a
face. "Really, I wouldn't mind seeing him with you."

"You want to see me having sex with your little boyfriend?" Amy
laughed. "You're crazy, Jack. You always were, but this..."

"He's a smart kid, straight A's in school. He's sweet like you
wouldn't believe, Amy," I said. "He lives in a dump with a mother,
who, well, she's a dump too, put it that way. I can't leave him there.
He deserves better."

"There's a lot of dumps in the world," Amy sighed and she was moving
again, enjoying our slow fuck despite herself. "You can't save
everyone. You can't kidnap this boy and you can't be his father and
his lover too, Jack. It doesn't work like that."

"I know," I said.

"And you're already married," Amy told me and that was her real point.
The one she wouldn't let go. Bringing Jamie here to live with us would
be a lot like marrying the boy and we both knew it.

"Can I bring him over?" I persisted, helpless to do anything else. It
was in my head now, bringing Jamie here to stay with us, for so many
reasons and some of them probably wrong, but some of them had to be
right too.

"Jack..." Amy sighed.

"Please? Just meet him? Will you do that for me?" I asked her. "I
promise, if you don't change your mind, I'll let it go. If you don't
like him or...Whatever."

I'd almost said 'love him' but that would be expecting too much.

"You promise me?" Amy asked and she knew I'd never break a promise to
her. Not in a million years. I made promises to other girls, like
Lonnie wanting a baby, but those hardly counted. With Amy, I had to
play it straight every single time.

"Yeah," I swallowed hard, looking into my wife's eyes. "I promise."

"Alright, Jack," Amy said after a long heartbeat. "I'll meet him,
but..."

"Shhh..." I smiled then, pushing my cock hard inside her with a gentle
grind and holding myself there. "I love you so much, Amy."

"I know," she kissed me. "I just wish I was the only one you said that
to."

We made love several times that night and I did everything I could to
make Amy feel loved. It was all about her and all the while the wheels
were turning in my head. I'd call a lawyer in the morning, I decided.
Find out about getting social services to look at Jamie's home and
mother. I'd been to his house, officially invited in by the woman and
now I could file a legitimate complaint without arousing suspicions.

I'd find out about getting custody of Jamie, that couldn't be too
hard. I was a well-respected teacher, financially secure and married,
a fine upstanding citizen in the community. All we had to do was get a
social worker to declare the mother unfit. It would be hard on Jamie;
I was sure he loved his mother, but he didn't deserve her. He deserved
to be loved and spoiled. Amy would like him, she had to. Amy was a
good person, beautiful inside and out, like Jamie was. They had to get
along, didn't they?

I prayed for it briefly, striking another deal with God and it was
such a good plan, He had to see it...

If Jamie lived with us, if Amy agreed to it and we got custody of him,
how hard would be to bring them together? It would work, I was sure of
it. The three of us could be happy and Amy could stop her birth
control. She could have a child with Jamie, my child. The boy looked
like her, the same blonde hair and blue eyes. We'd have a baby that
looked just like its mother, that's all and if I had to finally
confess the one secret I had from my wife, she'd forgive me, I
thought. Amy would understand and maybe even appreciate my
precautions, but most of all; Amy would know that it was our baby.
Hers and mine and we'd love it, just like we'd love Jamie.

All I needed was a little help from on high, and maybe not even that
much.



=-=-=-=-=-=-=-=-=-=-=-=
End
Jack Valentine
jack.valentine.adventures@gmail.com

-- 
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