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Nifty - Transgender - Young Friends - Sissy Boy Neighbor - Sissy Boy Neighbor 4

Date: Tue, 8 Feb 2000 19:54:40 -0800 (PST)
From: Bill <>
Subject: My Sissy-Boy Neighbor, Part 4 (b/b, b/t)

NOTE: Sorry I take so long to write these things.
You may want to go back and read the previous parts.
BTW, this story is absolutely, completely fictional.

My Sissy-Boy Neighbor, Part 4

When we left off last time, Billy Hamilton (that's me - age 12)
and Freddy Simmons (13) were in the old abandoned barn,
clad only in black silk girls' panties, awaiting the arrival of
16-year-old Clem Bartlett for a replay of the sexual escapades
of the previous day. Clem and his brother Bobby (14, and
unexpected by Freddy and me) had just walked in and found
us younger boys hugging and kissing each other. As my sissy-boy
neighbor and I look on excitedly, our erections stretching
out the front of the panties, Bobby pulls off his lacrosse shorts
and Clem his sweat pants. Both are wearing jockstraps.

"Well, Bobby," said Clem, rubbing the front of his jock
and grinning; "time to get serviced by these sissy-boys.
Which one do you want?"

"Well, I know from experience that Freddy gives a hell of a
good blow job; but I think I'll go with the new kid. He's got
such a pretty mouth." Looking over at me with a practiced
sneer, and adjusting the growing bulge in his jockstrap, he said
"come on over here and kneel in from of me, cocksucker;
I got you what... Bet you'd like to take my hard cock up
your ass too, huh?"

Freddy chimed in, brushing his shoulder-length blond hair
off his forehead like a Hollywood starlet. "You can fuck MY
pussy anytime, Bobby" he vamped in a smokey feminine voice.

My heart was beating rapidly. Was I ready to be fucked by this
handsome 8th grader? Should I admit I'd never done it before?
The thought of getting fucked was very exciting... in concept.
Having already experienced the pleasures of a probing finger,
as well as two sessions with Freddy's vibrator toy, I knew that
anal stimulation sent me to the highest reaches of erotic pleasure.
But I was also apprehensive. Watching Clem fuck Freddy's ass
the previous day with his thick 7" cock had caused me to wonder
whether I would be able to do the same. Would it hurt?

Finally, I answered Bobby in a quiet voice. "Well... uhhh... nobody's
ever put their cock in my ass before. But... I'll try.... OK?"

Clem let out a long whistle. "Well I'll be, Bobby! You're gonna
get his cherry!" But then looked at me with a genuinely warm
expression and said "Bet you're scared, huh? Ain't nothing the rest of
us here haven't done. My big brother Frank cornholed me a couple
times a week when I was your size, before he went off to the Navy.
And I used to give Bobby's butthole a good workout a few years
ago. Ain't that right, Bobby?" Even in the dim light of the barn, I
could see Bobby blush as he stared down at his feet and grunted
noncommittally. Clem looked over at Freddy and winked, saying
"... and God knows how many times Blondie here has been fucked.
Yep; a regular 'right of passage'; that's what it is." Looking back at
me dressed only in skimpy silk panties, he added "And I'd guess that
you're such a natural-born little sissy-boy that you'll love it just as
much as Blondie does."

I actually felt affection for Clem and wished Bobby had chosen
Freddy instead of me. As I watched the strong 16-year-old taking
off his shirt and standing there in just a jockstrap, my mind flashed
for a moment on an image of him taking me in his arms and kissing
me... of him making love to me gently and carefully... of protecting
me in his muscular embrace....

But I realized that Clem - not to mention Bobby - would never
accept that kind of emotional component in sexuality between boys.
They only wanted physical gratification and had only disdain for
the kind of love that was developing between Freddy and me. For
them, queers like me and Freddy could be used and discarded...
with a modicum of humanity if they were decent guys like Clem.
Or accompanied by random bullying and humiliation if they were
like Bobby.

So why was I doing this? Well, for one thing, because Freddy was
so totally psyched for it and wanted me to be with him. But also
because I could sense from my own surging erotic excitement just
why this game - this faggot lifestyle - appealed to him so much.
The previous day, while walking home from our first encounter
with Clem, Freddy had tried to explain it to me. The gritty eroticism
of encounters with hyper-masculine teenagers... the thrill of living
dangerously... the turn-on of submitting sexually, of giving yourself
over to serve the lust of a strong and dominant partner... and the
subtle reversal of power that occurred when that lust became so
overwhelming that it brought the stud to a moaning, quivering, helpless
orgasm - a few moments in time when the athlete was controlled by the
faggot through the talents of his cocksucking mouth or the sexual
desirability of his tight hot ass.

Yes; I knew that I felt these same queer-boy desires. The sexual
excitement I was now experiencing led me to an inevitable
conclusion - that I actually DID want to be like Freddy... a faggot
slut, eager to be used by older stronger boys. And I wondered briefly
how often I would find myself on my knees, with my cock
throbbingly hard, to suck another boy - even (or especially!) one
who thought it was fun to bully and tease queers like us.

Clem and Bobby stood side-by-side as Freddy and I knelt down in
front of them. The older boy wore nothing but a jockstrap; his
muscular chest, weight-trained biceps, and solid abs were even more
of a turn-on for me than they were the previous day. Bobby was
pulling off his half-length lacrosse jersey, but left on his long athletic

socks and his practice cleats. He had the body of a teenage Greek
god - lean and muscled, though without the dramatic muscular
prominence that his powerful brother displayed. His smooth chest
was lightly tanned and he had a tuft of dark hair under each
armpit. A masculine growth of sun-bleached hair on his legs and
around his navel made his 14-year-old body irresistible. My face
was only inches from the full pouch of Bobby's jockstrap, and I
reached up to pull down the wide elastic waistband.

"Don't pull it down yet. Lick it. Start out by sucking me through
my jock, you sissy faggot" said the arrogant 8th grader. An erotic
shiver ran through my body. Not only did I not mind being called
a 'sissy faggot' and actually enjoyed being ordered to run my
tongue and lips over his sweaty athletic supporter before earning
permission to take his cock in my mouth. I licked along the ridge
of raised fabric, below which lay the object of my desire. Long
strokes of my tongue soaked the jockstrap material with my spit
and made his cock rise from a half-hard sideways angle to a straight-up
powerful erection. The end of his boner pushed the mesh material
up above the lower part of the waistband. I forced my mouth down
on it, sucking his cloth-covered cockhead. I tasted the sweat of
Bobby's recent lacrosse practice and inhaled the musky aroma of
his unshowered masculinity.

Looking over at Freddy, I saw that he was sucking one of Clem's
egg-size hairy balls. The pouch of Clem's jock had been pushed to
the side, and his thick 7" cock and low-hanging ballsack were free
of the confines. I really wanted Bobby's erection in my mouth where
it belonged. I wanted to remove the cloth barrier that held me back
from the intense sensual pleasure of sucking cock. I sent a silent
plea with my brainwaves: 'Please, Bobby,' I thought; 'let me see
your manhood; let me suck you for real!'

It worked! "Pull down my jockstrap, faggot, and suck me good....
But don't make me cum. I want to save that for your virgin
asshole." My fingertips slid beneath the broad elastic band.
The backs of my fingers brushed against the silky brown hairs
below his navel as I it pulled out and down. My heart was
pounding in my chest as I pulled the jockstrap down Bobby's
lean muscular thighs. There, inches from my face, rose an icon
of teenage male eroticism. An erect penis so... so PERFECT...
that I felt lightheaded. A little over 6" long, of moderate thickness,
smooth and flawless. His pubic hair was thick just above his cock,
but far more confined than the hair surrounding his brother's thick
rod. Another difference was the cockhead... just slightly broader
than the shaft... sculpted in perfect esthetic harmony, and not so
prominently mushroom-shaped as the fat battering ram atop Clem's
adult-size stalk. The foreskin of his uncut penis nestled just behind
the cockhead's ridge like a turtleneck shirt.

My fingertips traced lightly along the shaft and down to the dangling
ballsack, then back up again. My fingers wrapped gently around
the smooth hard penis and pulled down the loose skin, making the
beautifully shaped cockhead stand out above the taut skin. A drop
of pre-cum clung to Bobby's piss slit, and he moaned in a husky
voice "Do it. Suck me, sissy-boy." I licked my lips and let them
glide over the smooth flesh. My tongue followed right behind,
flicking into the piss slit to lap up the drop of precious fluid, and
then swirling around the entire knob as my lips descended lower
on the shaft. Slowly, my lips moved up and down the top 2 inches
of cock, with my tongue dancing over every surface of sensitive
flesh that my lips enveloped. My mind was almost in a trance...
single-minded in its concentration, giving and getting pleasure as
I marveled at the incredible sensuality of the act.

I reversed the action of my fingers, bringing the loose skin back
up over the ridge and around the cockhead, making a small
volcano of sensitive skin, into which my tongue-tip probed...
swirling between cockhead and foreskin flesh... hot wet tongue
against hot wet cock.

"OH, GOD! YEAH!" cried Bobby, as his fingers slid along the
sides of my head, gliding through my short brown hair. At the
same time, his hips jerked forward with the automatic reaction
of his brain and body driving harder toward the source of pleasure.
I thought to myself 'It's time to take him all the way', and I let
my hand slide down to his ballsack. I caressed the pecan-size
balls, dangling within a sling of the softest flesh, as my wet lips
moved down, followed always by my teasing tongue. My head
slowly rose and fell above Bobby's crotch, plunging his boner
deeper into my hungry mouth with each descent. I paused only
a moment to let my throat adjust to the entry of the smooth
narrow-headed cock, and then willed myself to take him all the
way... all 6 inches in my mouth, my lips pressed against his pubic
hair, the muscles of my throat pressing against the head of Bobby's
stiff penis. My lips slid up and down Bobby's slippery shaft several
more times, each time running the entire length from cockhead to
base and each time pausing while his cockhead lodged deep in
my throat. Then I turned my full attention to his cockhead and
foreskin, sealing my lips around the shaft and sucking while my
tongue inflicted intense pleasure.

"Oh, SHIT!! Yeah! Suck it, kid! Oh, God! Yeah; like that!"
moaned Bobby. His ballsack pulled his nuts up close to his
body as my left hand squeezed them firmly. My right hand
rubbed my own 4" erection through the front of the silk panties,
and then I quickly pushed them down a bit so I could stroke
myself more easily. Bobby's hands were entwined in my hair
and his moans of pure lust signaled his satisfaction with my
efforts. I looked upward at his face. His eyes were closed and
the expression on his face could easily have been mistaken for
pain, though I knew he was feeling the most exquisite sexual
pleasure. His mouth hung open as rapid breaths interspersed
with incoherent grunts. I believe he was nearing the point of
no return, but I couldn't stop even if I'd wanted to. Bobby's
hands held my head firmly, locking his throbbing penis inside
my cocksucking mouth.

Glancing over to the side, I saw Freddy serving Clem with
his mouth in much the same way I was servicing the younger
brother, mixing long deep-throat plunges with vigorous suck
action centering on the older boy's sensitive cockhead. Freddy's
mouth strained to take the thickness of the 16-year-old's 7"
cock, but he clearly enjoyed it, and was making almost as many
noises of pleasure as the two farm boys were.

It was Clem who stopped the action short, pulling Freddy's
mouth off his rigid cock. "Whoa! Hold up, there Blondie" and
his boner emerged from Freddy's mouth with an audible 'plop'.
"Hey little brother. You're gonna lose your chance to cornhole
that pretty faggot if you don't take a breather." Bobby's hips
backed away from my face as his hands pushed my head out
a bit. I was sweating from the exertion and breathing hard, but
I was totally exhilarated. My right hand held my boyish stiffy
as I stared at Bobby's spit-slick boner, throbbing with lust
above his tight round ballsack. Freddy and I stayed on our
knees, looking up at the two older boys and awaiting our orders.

"Let's get our sissy-boys ready to be fucked" said Clem, and he
directed us over to a couple bales of hay lying close together,
telling us to kneel facing each other on opposite sides of the bales.
Freddy collected our clothing and spread it out on the hay so it
wouldn't scratch our naked bodies. We both took our panties the
rest of the way off and knelt down, our arms and chests resting
on each hay bale, our faces close enough for me to feel Freddy's
excited heavy breathing. I think Clem wanted to watch Bobby as
they were fucking us, but I appreciated being so close to Freddy,
and my love for him warmed my fast-beating heart. Freddy had
handed Clem the small bottle of lube that he always seemed to have
with him, and the older boy slathered some on his straining erection
before passing it to his brother. As Bobby did the same, Clem said
"Put some on his asshole. You gotta give the boy the gentle treatment
when you first start out. Remember how I took care of you that first
time... back when you were just a young'n?"

I felt Bobby's slippery fingers smoothing cool lube on my anal
area, then poking his index finger into me - a bit to roughly for
comfort. He quickly added a second finger and twisted them
inside me. My heart was pounding in my chest as he knelt behind
me, spreading my knees more apart and placing a hand on each
of my slender ass cheeks. But what I was watching was Clem,
pushing up against Freddy's ass, and Freddy's face - reacting to
the insertion of the mushroom-head cock into his body. It appeared
that my 13-year-old lover was feeling a combination of pleasure,
discomfort, and excited expectation as the older teenager grunted
his satisfaction at sliding into Freddy's accepting fuck-hole. In
another moment it was my turn. I felt Bobby guiding his cock to
my asshole, rubbing it back and forth at the entrance a few times.

"Remember to push out" whispered Freddy, his face only inches
from my own. "And if it hurts, bite down on something... like this
belt" he said, pulling the end of the thick leather belt from the
folded pants that separated his chest from the prickly hay. As Bobby's
cockhead pressed against me, my anal muscle opened to accept him.
As I felt him gradually slide into me, I felt an intense burning
sensation and clamped my teeth down on the doubled-over
strip of leather, my body tense and my eyes tightly shut.
The fire spread deeper into me, and tears started rolling down
my cheeks. Bobby's cock was slow but steady as it slid into
me, deeper and deeper, not stopping or pulling back, filling
my rectum, and stretching the virgin ring of muscle at its entrance.

"Oh, YEAH! God, boy; you got a tight hot ass. Ahhhh; that
feels so damn good!" groaned Bobby when he finally stopped
his inward thrust... with his cock pushed all the way into my fuck hole.

As I caught my breath, it flashed through my mind that I was
serving as the little brother that Bobby never had. I envisioned
myself in a dark farmhouse bedroom, late at night, silently
accepting sexual domination by an older brother - just as Bobby
and Clem had at my age. I thought of how these two must have
felt when they were being fucked for the first time, kneeling
naked and submissive, with ass upraised, trembling with a mixture
of excitement and apprehension; resigned to being sexually used
by a sibling that they... they what? Admired? Feared? Both?

But I was not a younger brother following an incestuous family
tradition. I was a virtual stranger. A middle-school faggot who
was doing this because of some budding sexual compulsion.
But the pain made me reconsider the whole thing; made me
wonder what I had gotten myself involved in. I felt Freddy's
hands grasped my own and I squeezed. Then I felt the cock that
filled my insides reverse direction and draw back; and still my
teeth bore down on the leather belt. When the direction reversed
again, Bobby's 6" cock entered me faster, again pushing to the hilt.

With my brain swirling with disjointed thoughts, I let out a muffled
grunt with each thrust of Bobby's stiff penis into me. Yes, partly
from the burning discomfort, but also from the jolts of unique
sensation that ran through me. My mind focused on those more
pleasing feelings and thought 'Hey! I'm actually being fucked!
I'm offering up my ass to this hunk of a lacrosse player, and I can
take it! Maybe I'll never do this again, but I can see this through
ok this time.' Bobby settled into a steady rhythm of long fuck
strokes, holding onto the knobs of my hip bones as his strong
lean body pushed forward into my butt-hole.

And then something magic happened... the burning pain was
being transformed into sensuous warmth; the feeling of being
invaded turning into the excitement of receiving the rhythmic
slippery thrusting of Bobby's beautifully erotic teenage cock.
And each time his 6" cock pushed all the way into me, my
own stiff penis throbbed. Without knowing when the transition
has occurred, I realized that the belt had fallen from my mouth,
and I was moaning with pleasure to mark each in-stroke. The
initial pain and apprehension was almost completely replaced
by my animal lust. I opened my eyes and was face-to-face with
Freddy. He was blissed-out... loving the sensations he was
feeling... glorying in the anal assault of Clem's thick battering ram.

"Oh, Billy" he gasped as he looked into my eyes lovingly; "this is
so WONDERFUL. I'm so glad we're doing it together. It's just
the ULTIMATE turn-on for me." He let go of my hands and touched
my face, then stretched his body forward so that our lips could
ouch. With the Bartlett brothers behind us, pumping away at our
assholes, Freddy and I kissed... our tongue tips making first
contact, then merging in the passion of wet lips and open mouths.
Our hands wandered over each other's arms, shoulders, hair,
and faces. And then my right hand snaked its way between my
hips and the hay bale to grasp my rigid erection. It was exquisitely
sensitive to my touch and primed for a quick orgasm.

"Oh, MAN! These faggots are in sissy-boy heaven!" said Clem,
breathing hard. "How you doin' there, Bobby? Don't know
about you, but I think I'm ready to finish this up."

"Oh, Jesus!" Bobby gasped. "I'm about to fuckin' explode!"
With his sweat dripping down onto my lower back and ass,
Bobby's thrusting body went into high gear, his hands holding
tight to my slender hips. I responded by jacking my cock fast
and hard, feeling the approach of orgasm infusing my body
with that indescribable sensation of sexual pleasure.

All four of us were vocalizing our lust as sounds of orgiastic
sex echoed through the old barn. The long sliding strokes of
Bobby's cock compounded the feeling produced by my stroking
fingers. The circuits of my nervous system were heavily
overloaded, and my brain was focused on the overpowering
feelings. With each fast thrust into my butt, I babbled fragments
of thoughts. "Oh...yeah!... Fuck!.... Fuck... me!... Oh... Yeah!...
Shove it... In me!... Oh... YEAH!"

I had stopped kissing Freddy because my entire being had
turned inward. My breathing stopped and my body went rigid
as the fast-building tension exploded in the release of orgasm.
Cum spurted past my feverishly-stroking hand and my anal
muscle spasmed rhythmically with each pulse of my cock.
Almost immediately, Bobby's thrusting tool erupted inside
me, splashing hot fluid deep within my body, accompanied
by his groans and whimpers.

Bobby collapsed across my back, his twitching cock still buried
in my ass, and he gasped for breath and moaned "Oh, God...
yes... so good; oh God!" I could feel his heart pounding as he
brought his arms underneath my body and around my chest.
I lifted myself on my elbows to let his strong arms surround me.
His hot breath flowed over my back, and I'm positive I felt his
moist lips press softly on my skin before he lay his cheek down
between my shoulder blades. I felt drained, but exhilarated. I
was especially thrilled by Bobby's protective embrace and tender
kiss on my back. But then he quickly realized that these actions
conflicted with his macho imperative, and he suddenly pulled
away from me and stood up. Both of us watched as Clem and
Freddy finished their dance of lust.

"Oh, you incredible stud! Fuck my hot pussy!" Freddy urged
in a breathless voice. "Fuck me like a whore! Oh, yes! Shoot
your cum deep in my boy-cunt!"

With the triumphant roar of a rutting animal, the 16-year-old
hunk gave one last thrust and released his pent-up load of
hot semen, coating the inside of Freddy's love channel with
spurt after spurt from his throbbing hose.

Maybe it was because I was in a daze, but it seemed like Clem
and Bobby were gone almost before I realized it. The Bartlett
brothers dressed, with only a little bantering between them,
as Freddy and I lay there face down on the hay bales, still
naked... touching each other, kissing a bit, smiling with groggy
satisfaction. But I distinctly remember Bobby's parting words
to me: "That was good, faggot. I think I might enjoy using
your mouth and butt again sometime. See ya around school."

When they were gone, Freddy got up and sat beside me,
taking me in his arms and kissing me. He must not have
cum yet, because his boner strained up against his belly.
I held the throbbing erection as we kissed romantically.

"Did it hurt you much?" he asked in a soft voice. "I felt so
bad when I saw your pain at the beginning."

"Yeah; it hurt like hell at first. But I really enjoyed it at
the end. I'm kinda sore down there though."

Freddy kissed me warmly and said "let me make it feel
better. Lie down on your back."

'Oh, Christ!' I thought to myself. 'He's not going to fuck
me too, is he?' But when I lay back on the clothing-covered
hay bale, Freddy brought his face down to my crotch. He
pushed my legs back and brought his tongue tenderly to my
fuck-worn ass hole. With gentle licks of his warm, wet tongue,
my 13-year-old lover soothed the soreness. Since the muscle
was still dilated from the recent fuck, he could easily sink his
tongue into me, and cork-screwed it around in the most incredible
way. God! I was getting horny again! I brought my fingers to
my stiffening penis and stroked gently. Oh, yeah; what a
combination! As Freddy's tongue licked and probed, I jacked
myself in urgent fast strokes. In a minute, my body was shaking
with intense vibrations of another orgasm. Only a few drops
appeared at the end of my cock, but it was intense!

Freddy's head rose up and he smiled at me. "Feel better now, lover?"

"Oh yeah!" I breathed. And after a few moments added "want
me to do that to you?"

"Oh, darling; yes! That would be heaven!"

As we were trading places, I watched his 6" erection swaying
enticingly as he walked over and picked up one of the silk
panties and held it in his hand. Then he lay on his back and
pulled his slender legs up so his ass was fully exposed to my
view. The skin around his tender hole was an angry red from
the vigorous thrusting of Clem's thick erection. It glistened
with lube, and a small trickle of white cum leaked down. I don't
know why I felt no reluctance to do this; a week ago nothing
could have convinced me to bring my tongue to another person's
ass hole. But here I was, doing it as if it were a sacred rite...
something that actually excited me.

The tip of my tongue touched the secret place and Freddy
moaned. My tongue explored in tentative motions as I gently
circled around the puckered reddish flesh, tasting the sweetness
of the lube, the saltiness of teenage cum, and the earthiness
of Freddy's natural essence. My lover started to masturbate
himself, holding the silk panties in his hand and brushing
them up and down on his erection.

My hands spread his ass cheeks wide and my tongue zeroed
in on rosebud of quivering nerves that he called his pussy...
his boy-cunt. I pressed, and easily penetrated the circle of
stretched muscle. I imitated the cork-screw twisting that he
had used on me, and also pushed straight in with tongue held
rigid and fucking in and out. Mostly, though, I just lapped at
this mysterious source of pleasure with the flat part of my
tongue. Gazing up, I could see Freddy's stroking hand jerking
wildly and his hairless ballsack pulled up tight, only inches my
eyes. With cries of pleasure, Freddy quickly brought himself to
a crashing orgasm as I stimulated his love hole as intensely as I
knew how.

We dressed slowly, with frequent kisses and loving caresses,
and finally headed for home. We'd only been in the barn for
about 40 minutes, but it seemed an eternity of sexual discovery.
As we walked home, Freddy talked about getting together at
his house for a sleep-over the following weekend, making vague
references about us getting "dressed-up" and some clothing
that he was dying to show me. I was so naive; I silently wondered
why we'd get dressed up if we weren't going anyplace special.

The next day at school, I tried to concentrate on studies, but
my mind kept wandering to sexual images and feelings,
especially when Freddy was with me in the classroom. As I
was walking to gym class near the end of the school day, a
husky 8th grader fell into step next to me. I vaguely recognized
him as someone I had seen around school, but I didn't know
his name.

"Hey kid.... Yeah, you.... I'm a friend of Bobby's, and he says
you're a really good sport." Then lowering his voice a bit, he
said "how about you meet me in the grove of trees behind the
gym when school lets out?"


"No buts, faggot" he whispered. "Just be there."

[to be continued]

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Nifty - Transgender - Young Friends - Sissy Boy Neighbor - Sissy Boy Neighbor 4