Author: wolfcub
Title: Transgender Boy
Summary: A cross-dressing boy becomes a little too much like a girl.
Keywords: bb exhib tg 1st oral anal

My parents are weird. I mean, everyone's parents are weird, but mine 
are extra, beyond-normal-weirdness, weird. And I'm an only child, so I 
get more than my fair share of their weirdness.

My dad likes showing off my body. When I was a baby, I rarely wore 
anything more than a diaper. Once I was out of diapers, I became Naked 
Boy (a nick name my aunt gave me that was used by most of our family 
and my parents' friends).

I rarely wear more than a pair of shorts outside, and  I'm always naked 
at home. Even when my parents' friends--and their children--are 
visiting, I'm still completely starkers. The kids used to play naked 
with me, sometimes, but around age 7, they started to keep their 
clothes on, as do my current friends, when they're over.

When I do wear clothes, its usually loose-fitting shorts (really short 
shorts--not those below-the-knee kind that most boys wear) and a tank 
top, muscle shirt, or some kind of mesh thing that only technically 
qualifies as a shirt.

My mom's into photography (she's really good at it, too), so the walls 
of our house are plastered with pictures of me--mostly either 
completely naked or mostly so. She even posts pictures of me naked on 
her online photo journal.

When I was four years old, my parents decided to go on a vacation to 
the Caribbean. Their last real vacation had been shortly after my mom 
got pregnant with me, so they were really looking forward to the trip.

Not to let an opportunity to be weird slip by, my mom decided it would 
be fun if I were to "take a vacation from being a boy." She found a 
bikini bottom with a frilly skirt in the front to cover the bulge that 
shouldn't be there. That and a white sundress were my only clothes for 
the week. I had wavy, blond hair that came down to my shoulders (like I 
still do, now) so I did a fair job of passing for girl. I was four, so 
what did I care? My dad was a little disappointed that he couldn't 
undress me at the beach showers, like he did at home, but I think the 
fun of showing off his topless "little girl" made up for it.

My parents enjoyed the vacation spot so much that they decided to 
return the next year. At five, I had to be let in on the 
pretend-to-be-a-girl gig, but Mom made it fun, so I was game. It became 
an annual event, and I actually enjoyed hanging out with girls, for one 
week out of the year.

At eight, it became a little weirder. Eight-year-old boys don't talk 
about girls--except the odd comment about how icky they are--so I was 
surprised to find that that was a primary topic of conversation among 
my eight-year-old girl playmates.

Most of the girls, including me, went topless and wore skimpy, 
string-bikini bottoms. (Mom had found me one with a frilly little flap 
in the front to conceal the fact that I was a boy, but otherwise, I was 
as near-to-naked as my girl companions.) A much-discussed topic was the 
fact that most of the boys here wore racer or square-cut 
swimsuits--unlike the ubiquitous board shorts common at home.

I learned quite a bit about what girls find attractive about boys (at 
that age, hair, eyes, smile, and muscular arms and chest were popular 
with almost no mention of butts or bulges; those came later), and I 
later made use of that knowledge to attract quite a few girls--once I 
was old enough to be interested.

At ten, the talk turned from attraction to sex. If you've never hung 
around ten-year-old girls, you may be surprised to learn that they talk 
about sex--but they do. And marriage. And making babies! The first time 
I heard a ten-year-old girl say, "He's hot! I'd like to have his baby!" 
I choked on my fruit punch and almost spit it out.

The next big change came at eleven. That's when the boys started 
showing interest in the girls. The first time an eleven-year-old boy 
came up to talk to me, I didn't think anything of it--at first. I 
talked to eleven-year-old boys all the time. It was when I realized he 
was acting sheepish, and his friends were giggling, that it occurred to 
me that he was hitting on me (in that awkward, eleven-year-old way)!

I had been on the other end of a similar encounter several times, 
myself, recently, and I felt for the boy. Plus, Mom had always played 
up the fun aspect of pretending to be a girl, so I decided to play 
along, not considering the implications of my actions.

"Is this your first time here?" the boy had asked, with all the weary 
of any "Do you come here often?" line. I'm pretty sure my smile came 
across as a sign that I was tickled to be taking to a boy rather than 
an indication of my amusement.

"No, my parents and I have been coming here every year since I was 
four. Is this your first time?" (Okay! Being the same age, I'm allowed 
to use the same, lame lines! Gimme a break!)

"Maybe you can show me around!" he said, with rather a lot of hopeful 
enthusiasm. "This is my first time here."

"Maybe," I answered, coyly, sizing him up with my eyes.

His strait, light-brown hair came over his ears and almost hung in his 
eyes, but it didn't reach as far as his shoulders. He had green 
eyes--like me--and a cute nose. His shoulders where broad, and his 
chest somewhat muscular--but not overly so. He had a taut belly and 
long, muscular legs.

From the outline on the front of his shiny, blue racer, I could tell 
his testicles were a little large for a boy his age, and his stiff 
penis was about average girth and length. I felt my own penis stir and 
worried that I'd blow my cover if I tented the skirt on my bikini 
bottoms.

"Let's go for a walk!" I said, taking his hand and almost dragging him 
from his friends. I didn't have any particular destination in mind--I 
was just avoiding giving him the opportunity to discover my secret. 
There was lots of giggling behind us--from both boys and girls--but 
none of either of our friends followed us.

When the giggling was out of range, I slowed our pace so that I was no 
longer dragging my companion. We were nearing the pool area of the 
hotel where my parents and I were staying, so I led him to the bar and 
asked, "What some ice cream?" Without waiting for an answer, I hopped 
up on one of the stools; my friend sat beside me.

While watching our sundaes being made, we chatted about nothing. Turns 
out he was staying with his parents in the same hotel. With our legs 
dangling from the bar stools, I found myself idly playing with his legs 
and feet with my own while we talked. When I realized what I had been 
doing, I saw that he was blushing, and the front of his swimsuit was 
fully bulging. I blushed, myself, and we were both thankful to be 
distracted by the arrival of our sundaes.

We continued talking while we ate. This time, I intentionally brushed 
my legs and feet against his. The stools were close enough that I was 
able to spread my legs and just touch his bare thigh with my own. 
Seeing the reaction I was getting--and thoroughly enjoying it--I put my 
hand on his shoulder, leaned into him, and whispered into his ear, 
"You're cute!"

I sat back and enjoyed the embarrassed smile on his face.

Next, I swiveled by stool to face his and made a more deliberate effort 
at massaging his legs with my feet. After a quick look around the bar 
to see that no one was looking our way, I pressed my foot into his 
crotch, curled my toes around his stiff penis, and gave a playful 
shove. He quickly brushed my foot away with one hand and adjusted 
himself in his swimsuit with the other.

Undeterred, I placed a hand on the upper inside of his thigh and gave a 
gentle squeeze. I teased him, mercilessly, doing all the things I 
wished a girl would do to me. By the time we had finished our sundaes, 
I was surprised he hadn't wet himself.

I took my new boyfriend by the hand and led him away from the bar, 
following the path that led to the bungalows. I let go of his hand and 
slipped my arm around his waist, hugging him towards me as we walked. 
His body stiffen, at first, but then he quickly relaxed, slipping his 
own arm around my waist.

I noticed a small clearing in the bushes, just off the path. On 
impulse, I led my boyfriend into the somewhat secluded cranny. I turned 
toward him, drawing him to me, and pressed my nose against his. We both 
had huge smiles on our faces.

His hands slid down my back and cupped the exposed flesh of my cheeks. 
I kept my hands on his hips so that I could prevent him from pressing 
his crotch against mine, as I was certain he'd immediately detect the 
bulge of erection raging beneath the thin skirt of my bikini.

I was surprised when he kissed me on the lips, but I kissed him back. 
Then, I tentatively pushed my tongue forward. Without objection, he 
pushed back with his, and we were quickly making out like horny 
teenagers.

His hands were all over my body, but I kept my own securely on his hips 
to protect my secret. Suddenly, I realized that he was trying to pull 
my bikini down. I grabbed his wrist and pulled away from him, ending up 
on my knees.

I had heard lots of talk about what girls do for boys. I had often 
thought about having a girl do those things to me, but I had never 
considered doing them to another boy; however, I knew that if I didn't 
do something quickly, this boy was going to push me onto my back and 
climb on top of me.

So, without really any thought, I hooked my fingers into the front of 
his swimsuit, pulled them down, and caught his springing penis in my 
mouth. Fortunately, the surprise checked his advance.

I finished pulling his swimsuit to his ankles as I sucked vigorously on 
his penis. I then cupped his buttocks with one hand and fondled his 
testicles with the other, all the while sucking for all I was worth.

After having teased him so viciously, he didn't last long. I was 
surprised by the quantity and force of his ejaculation. I had just 
started squirting, myself, a few months ago, but mine was just a few 
drops of thin, watery fluid. I now had a considerable amount of thick 
fluid in my mouth. Again, without really thinking about it, I swallowed 
to keep from choking.

A few more, much smaller squirts followed, and I swallowed them, too. 
It was then that I fully realized what had just happened--and that I 
had rather enjoyed it! I gave a long, hard draw on his softening penis 
and let it slip from my mouth.

The boy collapsed to his knees and pressed his nose against mine. We 
were both giddy with laughter and breathing heavily--his exhales timed 
to my inhales so that we were both breathing the same air.

After a minute or so, he asked, softly, "Do you want me to do you?"

I was puzzled, at first, then I realized what he meant. I tried to 
quickly think of a reasonable excuse for saying no, but then we heard 
the voices of some people approaching along the path. He hurriedly 
tugged on his swimsuit, and we emerged from the bushes just as two 
adult couples rounded the curve in the path. They smiled, and nodded a 
greeting to us, but they were too involved with each other to give us 
much notice.

On the way back to the hotel, we ran into his friends and mine. Both 
were anxious to hear what had gone on. We clustered in two separate 
groups, and while the girls peppered me with questions, I could tell 
from the reactions from his friends that the boy wasn't holding back 
any details.

"So, what's his name? You don't even know his name? Damn, girl!"

That night at dinner, I slipped out to the pool while my parents were 
dancing and ran into the boy. I was, as usual, wearing only a sundress; 
the boy was wearing khaki shorts and a light-blue polo shirt. Like me, 
he was barefoot. He walked up to me and shyly said hello.

"You know," I said, just as shyly, "We don't even know each other's 
names! Mine's Jayden." (My real name--which, conveniently, works for 
both a boy and a girl.)

"I'm Josh."

He smiled when I placed my foot on top of his.

"Are you going to the dance, tonight?" I asked.

"What dance?"

"There's always night-time activities for kids and teenagers--so the 
parents can have some alone time." I cringed at my unplanned use of my 
parents' corny, embarrassing phrase.

"I'll have to ask my parents."

"Cool! Where are they?"

He led me to the opposite side of the dining room from where my parents 
and I were seated. His parents were considerably younger than mine. 
They immediately noticed that I was holding their son's hand--and they 
seemed quite pleased about it. They gave their consent without 
hesitation.

My own parents gave me their "Are you sure you want to do this?" look; 
I replied with my best, "This whole thing is your fault" scowl, then 
Josh and I were on our way.

This dance was for the eight- to twelve-year-olds, so there wasn't as 
much dancing as there was standing close to each other and shuffling. 
The hotel chaperones saw to it that the boys and girls didn't 
congregate on opposite sides of the hall for too long.

Josh and I were soon shuffling together with our hands on each other, 
but the presence of so many other kids kept them from roaming 
around--too much.

If I had had a pair of panties, I would have worn them that night, as I 
was deathly afraid of tenting out my dress; however, even at eleven, I 
had a scant two inches stiff, so it turned out it wasn't a problem. 
Josh had no problem tenting his shorts with his beautiful four inches. 
Did I say beautiful? Maybe playing the part of a girl makes me think 
like one, but I didn't just think his penis was beautiful. He was 
beautiful! And I was proud to be dancing with him in front of so many 
other boys and girls.

Of course we ran into my girl friends--all the girls always went to all 
the dances--but we didn't run into any of the boys Josh had been 
hanging with earlier that day. There were enough boys so that my 
friends found dance partners without cutting in on me and Josh--which 
they sorely wanted to do and which I wouldn't allow.

"You're so lucky!", my friend Sierra gushed, after dragging me away 
from Josh to get some punch. "So, are you going to do more with him 
besides what you've already done?"

"Sierra!"

"Don't, 'Sierra!' me! I'm not the one who sucked off a guy I just met! 
I figured, if you moved that fast, you'd be spreading your legs for 
him, tonight."

"Don't!" I said, with my best girl-squeal, which I could do now without 
even trying.

"My parents are on that moonlight cruise," Sierra rolled her eyes as 
she said it, "So I'm hanging with Katelyn and her parents, tonight. I 
could give you my room key."

"Sierra! Stop!"

Just then, Josh came over to get some punch, himself, rescuing me from 
further torment from Sierra, but leaving me with the same predicament.

Josh talked me into going for a walk, and we easily slipped the hotel 
chaperones.

"So," Josh said, with some hesitation, "Do you wanna come up to my 
room!"

"And do what?", I asked, suspiciously.

"You know! We could, like, make out again--and maybe you could..."

I actually blushed, remembering what I had done.

"Are you sure you don't want to do something else?" I asked, with a 
sinister grin.

Josh's eyes widened. "Okay! I just thought you wouldn't want to--so 
quickly. You know?" His sudden enthusiasm made me laugh!"

"Slow down, stud puppy!" My mom had started calling me that after she 
found out I was getting interested in girls. "I'm not gonna do that 
with you."

"Oh." The dejection in his voice made me sorry I had said it, but there 
was no way that would end other than badly. Still, my devious smile 
returned, and I added, "Yet," which brought the smile back to Josh's 
face.

So, over the next few days, I managed to make out with Josh--quite a 
lot--and give him a few more blow jobs--greedily swallowing each 
time--without letting him gain access to the parts between my legs that 
would ruin our little pre-teen affair.

On one level, I felt kind of bad about what I was doing. Josh was quite 
the looker, and it was clear that he could have gotten a real 
girl--maybe even one that would let him do the thing that boys liked to 
do with girls--if he wasn't preoccupied with me, thinking I was that 
girl.

On the other hand, Josh was my first love. I realized that very early 
on. I was actually in love with him--in that pre-teen, puppy-love kind 
of way. I began wishing I could tell him my secret--and that he'd still 
like me after finding out.

"Dad?" I began, two nights before we were leaving, lying naked on my 
back on the bed in our hotel room with my penis sticking straight up 
toward the ceiling. "How can I make Josh like me."

"I think he already likes you," my dad answered.

"No, I mean as a boy. He likes me as a girl."

"After the way you two have been carrying on, I don't think Josh would 
recover from finding out you're not a girl. It's best just to let him 
go home thinking he had a good time with a beautiful girl on vacation."

"He wants to have sex with me."

"A lot of people want to have sex with you."

I sat up. "What do you mean by that?"

"Nothing. You know what having sex with a boy means. I don't think 
that's what Josh is looking for."

I crossed my legs and idly stroked my penis. My parents have no qualms 
about boys playing with themselves--and my mom has plenty of pictures 
of me doing it from infancy onwards to prove it.

"Maybe he doesn't, but he'd like it anyway."

"Jayden," my dad said, tenderly, putting an arm around me, "I'm pretty 
sure if you tell Josh the truth, he'll get mad and probably say a lot a 
mean things to you. I don't think you want to risk that, do you? It's 
better if you go home with good memories of Josh."

I sighed and stopped stroking my penis, which was beginning to deflate. 
My dad, who's usually good at figuring things out, came up with a 
solution for me that brought a smile back to my face.

The next day, Josh and I were sharing a lounge chair on the beach in 
the shade of an umbrella when I put my dad's plan into action.

"Josh, have you ever fooled around with a boy?"

Josh stiffened up and got all nervous. "What?"

"My girl friends and I--back home--fool around, sometimes. You know, 
practice kissing--stuff like that. I was wondering if boys do the same 
thing. My friend Emma says she caught her younger brother fooling 
around with his best friend, but he denies it."

"Um..." Josh's attitude made me suspect that the answer was yes, which 
was exactly what I was hoping for. "I...uh..."

"It's okay if you do! I don't mind. I'm just curious."

"Well, once--at a sleepover with my best--he and I sort of..."

"Sort of what?"

"Do we have to talk about this?"

"No, but I'd like to talk about it. Did he suck you, like I do?"

Josh's face turned bright red, so I knew that he had.

"And did you suck him?"

I wouldn't have thought it was possible, but Josh's face got even 
brighter.

"You did, didn't you? That's okay. I think it's cool to think of two 
boys sucking each other."

"You do?" Josh asked, a little relieved.

"Sure? Don't you? Otherwise, you wouldn't have done it. Did you do it 
more than just that once?"

Josh was squirming, again, so I knew he had.

"How often?"

Josh was getting more uncomfortable.

"You do it all the time, don't you?"

Josh looked like he was about to cry, so I leaned forward and kissed 
him on the lips. I pulled away to see that my kiss had cheered him, a 
little, so I leaned in and kissed him, again.

"Have you done anything else with him?"

"Like what?"

"Like the thing that boys do to each other that's like sex?"

"No," Josh answered, quietly, and with disappointment in his voice, "He 
didn't want to do that."

"Did you want to do that?"

"Kind of."

"Kind of?"

"Okay, I did want to, but there's nothing wrong with pre-pubescent boys 
doing that with each other. It's just experimenting." He stumbled over 
"pre-pubescent" and said the whole thing like he was repeating 
something an adult had told him.

I kissed him on the lips, again, took his hand, and led him to my hotel 
room, which my parents had promised to stay away from for the afternoon.

The door closed behind us. I stood in front of Josh and ceremoniously 
pulled on the ties holding my bikini bottom on. I let it fall to the 
ground. Josh's eyes widened, but he didn't run away screaming.

I put a finger to my lips, then walked over to the nightstand and took 
out the jar my dad had left for me. I scooped out two fingers full of 
the cream, then pushed the fingers into my butt hole. I climbed onto 
the bed on all fours, looked over my shoulder at Josh, and wiggled my 
butt at him.

Nothing happened for two full seconds, then Josh almost fell over 
tugging his swimsuit down. He pounced on the bed, wrapped one arm 
around my waist, and used his free hand to position the head of his 
stiff penis at my hole.

It hurt when he pushed in. He didn't go slow or in any other why try to 
be gentle. He was so anxious to avail himself of this opportunity that 
he just rammed his penis into me and started thrusting like a rabbit.

Even though it was painful, I liked having him inside me. I wanted to 
tell him to slow down, but he was lost in the excitement of the moment. 
Fortunately, he didn't last long. In less than a minute, he pushed hard 
into me and grunted. I felt his penis twitch several times, and I knew 
he was pumping his semen into my butt.

Eventually, he collapsed on top of me, but I was able to support his 
weight. It wasn't long before his penis softened, and he slipped out of 
me, at which time he rolled onto his back and laughed out loud.

I laid on my side next to him to avoid making a mess on the bed. I 
cuddled close to him and kissed him on the cheek.

When Josh had recovered, we did it again. This time--at my 
insistence--he went more slowly and gently. It was wonderful feeling 
him inside me! This time, it didn't hurt so much, and I was able to 
enjoy his stiff rod pistonning in my bowels. I loved the feeling of 
them opening up to receive his penis then collapsing behind it as he 
withdrew.

The next day, we put on the pretense of boyfriend/girlfriend for our 
friends--except that Josh was even more attentive to me than he had 
been all week. We were able to sneak away so he could fuck me twice 
more before I left with my parents the following day.

Sitting in the airport wearing my sundress, I caught the eye of a cute 
boy with red hair. He, his younger sister, and his parents boarded the 
plane with my parents and me. He looked about twelve and his sister 
maybe ten years old. I smiled while imaging a way to be with both of 
them.

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