Straight Neighbor Jay
Jay lived in the next door apartment with his mom. They didn't get along too well, so Jay
hung out with me and my roomate. I developed a on him immediately. He was
about 6' 1", dark brown hair, beautiful brown eyes, high cheekbones and a wicked
smile. A cute masculine farmboy face, with a strong brow and killer eyebrows. He was
beefy, broad shouldered and naturally muscular, with a deep sexy voice... in a word,
hot... totally my type.
Jay had admired my cowboy boots (which was a turnon in itself, having a straight guy
frequently comment on my boots). He always wore black leather Nike hightops (which on him,
was a turn on in itself), and I frequently encouraged him to get a pair of cowboy boots. I
had a pair of brown bullhide Tony Lamas (pointed toes) that were a bit big on me, so I
offered to let him wear them around to see if he'd like them. He agreed to it, so when I
got them from my room and he started to take off his Nikes, I got so excited I became hard
(BTW, his Nikes smelled incredible... a rich ripe, masculine/jock smell that drove me
nuts! A few weeks earlier, he crashed on our couch, and I sneaked off with his freshly
removed Nikes and jacked off with them, by burying my nose in one shoe, and pressing the
other on my dick until I came, while thinking about his gorgeous face and body).
He slipped the first boot on and flashed his wicked grin... the one I'd seen many times on
guys who try on cowboy boots for the first time (I worked at a western wear store at the
time). After he had them on, he adjusted his jeans and strutted around the living room
with that sexy grin, looking down at the boots. I couldn't tell for sure, but it looked
like he was getting hard. Probably just wishful thinking!
He had worn them almost every time I saw him... such a turnon! My goal was simply to get
those boots back after hed imparted his smell into them and fantasize that he's wearing
them and I masturbated with the boots. However a few weeks later, things got a lot more
interesting indeed!
My roomate and had planned to go to a rave (it was around '95), but he went to the rave
ahead of Jay and I. Jay had bought a bottle of Jack Daniels, and we proceed to have a few
on the rocks. I was wearing my Nocona lizard (peanut brittle color, pointed toes, shiney
as hell, and sexier than @#%$), which Jay seemed to admire the most (so of course I wore
them whenever he was around), sometimes staring at them for a long time. Jay was wearing
the cowboy boots I'd loned him, and much to my suprise, he began ocassionally playfully
kicking me in the backside throughout the course of the hour or so! It was such a hugh
turn on... and tease! He didn't kick hard enough to hurt, just in a friendly rough-house
kind of way... but always right in the crack of my butt! I later did the same to him, and
we started to rough house. He grabbed me in a head lock (I'll never forget how good he
smelled, or how good his muscular arm felt around my neck!). "You wanna lick my
boots?!" he said mockingly. It was all good-natured, and I didn't even hope that he
meant it, but it was a cruel tease!
We calmed down a bit, and sat on the couch and decided to watch a movie. After it had
started, Jay swung his booted up on the couch... on my lap! My
heart nearly leaped out of my chest as those beautiful size 10.5EE sh*tkickers landed on
my lap... just millimeters of denim between his boots and my dick! I couldn't believe was
was happening. The contact of his cowboy boots on my basket caused a tickling rush of
pleasure that was so intense I almost groaned! I didn't come, but it was the first time a
man had ever put his booted on my dick (#1 turn on for me,
and the main way I get off), so the pleasure of that simple act was better than many
orgasms I'd had in my life!
I got pretty uncomfortable, being afraid that he'd see that I was so aroused. Although his
boot was covering my erection, I was afraid he'd feel it. After about half an hour, he we
started talking about cowboy boots, what we like about them, how we feel when we wear
them, and how cool it'd be to be a cowboy. I started to relax a bit, and (thanks to Jack
Daniels!) got comfortable enough to rest my hand on one of his boots, and thumbing the
toe. I became hard again, and suddenly he started rubbing my hardon with his boot! Again
the pleasure of that action was so intense and I bacame apprehensive that he'd notice
it... but he kept on doing it, applying even more pressure to my rock hard dick. Then my
heart raced as he slowly lifted the boot (I was afraid he was looking to see if I was
hard, and would be pissed), and held it inches from my face! "I really like the was
my boots smell" And at that, he moved the toe of the boot just under my nose. It seem
appropriate to smell it... or if it wasn't, I wasn't going to miss the opportunity! They
did indeed smell incredible... the smell that a young beefy man who wears them every day
gives his boots: rich, sweet, slightly ripe, manly cowboy boot smell... one of the most
erotic smells on the planet in my opinion. The smooth bullhide even felt good on my
nostrils. He then placed the boot back on my jean covered hard on, and continued to stroke
it by moving his up and down.
One one hand, it was everything I'd ever wanted sexually (cowboy boots on my dick worn by
a beautiful stud like him), but I knew he was straight, so it was confusing and a little
awkward... but heavenly all the same! There's no way I could have come in that situation,
but I was enjoying every second of it.
I found myself staring intently at his georgeous sh*tkickers, admiring their beautiful
curves and lines.. the sexy way the of the boot curves down from
the heel, and then gently curves up again to the cocky pointed toe... and the brutishly
masculing shape of them... the sexy wrinkles his gave them...
He started to say something, but hesitated. But finally, "You ever... mess around
with your boots?" he said somewhat sheepishlly. Once again, my heart was in my
thoat... I couldn't believe what he said! "Yeah..." a said quietly, voice
quivering, blushing and rubbing my brow awkwardly. There was an uncomfortable silence
between use until, "How do you do it?" Jay asked... I hummed and hawed... very
awkward, but very turned on at the same time! "Uh... I ... kinda rub 'em on...
between my legs.. I dunno..." Blushing furiously, heart pounding. Jay sounded like he
felt the same as he said "You wanna maybe... do some stuff?" My adrenaline
red-lined! I couldn't believe what was happening! This is every sexual fantasy I'd had
since I was 5 years old, and that I never thought I would every get (at the time, I didn't
know anyone in the world shared my fetish). "Yeah sure..." I said, failing
miserably to conceal my manic excitement. By then, my underwear was wet with precum, and
my c*ck ached painfully from intense arousal, and for some reason, I was uncomfortable
with him seeing that (maybe he'd back out of it when he saw how turned-on I was).
"How do you wanna do it?" he asked. I thought to myself, screw it, I'm just
going show him straight out (but non-threateningly) what I like. I pulled my pants down
around my ankles and got on my knees in front of him, glancing at his obvious erection
(same size as me, from what I could tell). I grabbed his boot by the ankle, guidling it to
my still-underwear-clad manparts. The toe of his cowboy boot touched my scrotum, and a
huge rush of ticking pleasure once again rushed over my c*ck and balls, seeming to eminate
from the boot itself. Jay started to breath heavier... hopefully out of arousal! I then
began to hump the toe area of his left cowboy boot... it was as if I'd never really
experienced sexual pleasure until that moment! I couldn't believe how good it felt to f*ck
his boot! It felt as if his cowboy boot was vibrating with sexual energy. I then pulled my
briefs down (thank god! No skidmarks!) and resumed my position. He started poking a
proding my c*ck and balls himself, each poke and stroke a universe of c*ck pleasure. I
gasped at the rush of pleasure, rolling my eyes in the back of my head, trying to supress
groaning... and failing, letting out quiet, closed mouth whimpers and groans. Finally, Jay
pressed the of his left boot full bore onto
my dick, the pointed to digging hard into my scrotum at the base of my c*ck (he's found my
G spot!) and the upper of the boot pressed to my c*ck. I instinctively grabbed onto his
boot at the shank, and clutched his beefy muscular calf (he had beautiful legs, btw). I
humped his boot furiously. It felt like he was f*cking me with his boot, his cowboy boot
going inside me... it was incredible. The smooth warm leather felt awesome on my throbing
member, and I could feel the heat from his hot, sweaty , his boot felt so hard and manly.
I looked down and saw dripping precum on his jeans and on the boot, which suddenly began
to lubricate my c*ck's trip over his Tony Lamas... which increased the pleasure 10 fold! I
groaned long and loud, and the orgasm began to build... Hot tickling waves to pleasure
bagan to throb into my c*ck from his boot, and from his manliness.. his incredible face,
his muscular body, his smell... his voice... all channelling down into his amazingly sexy
cowboy boots, and injecting them into my @#%$ through the pointed toes. Finally the orgasm
his me like a ton of brick. Immense waves of pleasure eminated from his boot and ripped
though my c*ck and balls mercilessly, I groaned loud, lost in the sea of c*ck pleasure, by
far the most intense orgasm of my life at that time. My spurted all over his pant
leg, his boot and on the couch and floor... it looked 2 or 3 cumloads. After I came,
panting, I didn't want to let go of his booted ...
But Jay was more than eager to get his first taste of cowboy boot sex, and he hurriedly
jumped up from the couch and started to pull his pants and underwear down and assumed the
position I had used. I started to poke and prod, as he'd done, causing him the whimper,
though shallow uneven gasps. He had a beautiful dick... slighly larger than mine, and
fatter, perfectly shaped, like the rest of his body. I poked the toe of my right boot deep
into his crotch under his balls, and he
lifted up slightly, as if in apprehention, taking a deep breath, but settled down with a
quite whimper as my pointed toe
stroked the skin under his balls and then the balls themselves. He was precumming like
crazy as well, and I deeply
wanted to suck his dick (and to smell him, rim him, smell and lick every square inch of
his incredible body...). "Why don't you to step on me?" he said, laying on the
floor in front of me, head pointing away. I instinctively knew what he meant, and I
stepped on his dick, the heel on his scrotum between his ball, and started to
"massage" his dick. He groaned and reached down and held my boot to him, rubbing
it all over, looking down at the action. I threw him a pillow and he quickly proped
himself up and resumed stoking my cowboy boot, groaning softly, staring intently. I sped
up the rate of my c*ck/boot massage and he started groaning louder and breathing harder. I
stepped my other boot on his leg, grinding the sharp edges of the heel into his powerful ,
which clearly excited him even more. "Stomp on me.." he said softly though heavy
breaths. I obliged gently at first, which elicited an excited high "hurumph"
type pleasure cry. I continued to do his untill he asked "kick by balls with the toe.
I stood, and pointed my toe down, and gave him a gentle kick, causing a loud open mouth
cry of pleasure. I alternated stomping and kicking until his body started shuddering. When
he started to , I instinctivly stepped on
his dick, pressing hard and massaging his dick and balls thoughout his orgasm, his body
arched forward, eyes rolling in the back of his head, seeming to holding his breath for
the first few spurts of . them he screwed up his face
and let out a huge shout of emense pleasure. He lay back down, still groaning higher and
higher, then letting out what sounded like sobs with each breath, eyebrows sad, c*ck still
spurting. His face relaxed as the orgasm subsided, his chest and stomach covered in ...
probably a typical load for his huge balls!
After he came, I continued to step on his c*ck, intent to milk every drop if pleasure out
of his bootsex experience. When he begain to open his eyes I quickly walked into the
bathroom to get him a towel, and telling him he could shower if he wanted to (I tried to
act as if nothing had happened, so we could resume being friends, and so that he wouldn't
regret what I assume was his first homosexual experience... and to that maybe we could do
it again, of course!).
He seemed to be avoiding me somewhat after that experience, but warmed up to me again a
few weeks later. He later confided in me (with the help of our friend Jack Daniels again!)
that cowboy boots have always turned him on. And that once when I was at work, and my
roomate had left him alone to go to the store, he had snuck into my room and played with
my Nocona lizards! We never did again have boot sex, but I fantasize about the experience
to this day. Unfortunately, he couldn't handle his mom anymore (raging alchololic) and
moved in with a relative. Although it wasn't far away, we just lost touch.
Houscowboy