My Man Ass Cherry

November 29, 2007 – 10:00 am

Little did I imagine when I agreed to due a favor for a
former girlfriend a few months ago that it would lead
me to my first wild experience in man-to-man sex and my
coming out. Anne and I had dated for a while in
college and ended up in the Bay Area afterwards where
we were both in graduate school.

We were still friends, so she asked me to help her on a
school project. As part of her training to be a sex
therapist, she needed to learn about gay men and their
social life. She wanted to visited a gay leather bar,
but the place would not admit a women unless she were
with a male patron. She asked me to be her escort.

I knew of my own strong sexual interest in men, but I
had never acted upon these feelings or told her about
it. Sometimes, though, women have a sixth sense about
us. Anne knew more about me than she let on.

When I showed up at her place, she told me she’d dress
me for the leather scene. The next thing I knew I was
wearing a black leather vest, studded leather wrist
bands, tight leather shorts with a removable crotch
piece that extended around to my ass, and leather work
boots. “My, you look like a fag,” she remarked, in a
matter-of-fact tone.

The words stung a bit (I certainly wasn’t comfortable
with the label then) and I reddened. Then I looked in
the mirror I saw a gay man ready to cruise looking back
at me. It felt weird – odd, yes, but also very erotic.
I got an erection on the spot that I had a hard time
concealing in my very tight shorts.

She drove us in her car to the bar. Several men
standing outside noticed me and whistled and made lewd
remarks. Again I felt embarrassed but turned on. No man
had ever made sexual suggestions to me before. Their
comments made me aware of myself, or at least the parts
of me they seemed to admire – my tight little ass, my
slim build, my thick, pouting lips.

Once we were inside, Anne turned to me and said with a
smirk, “You’re going to be very popular in here
tonight. Don’t do anything I wouldn’t do.” And then she
pulled out her notebook and pen and excused herself to
do some interviews with the leather-clad gentlemen
around the bar.

I bought myself a beer and began to look around.
Immediately I realized that I had never seen so many
gorgeous men before. Most were attired in revealing
leather vests, pants, and even a few thongs, and many
wore various kinds of harnesses. Some were magnificent,
muscular physical specimens; others were hairy and
heavyset. There were also a few who looked more like
me: smaller and slimmer, short hair and neatly trimmed
beards. I took a deep breath and decided to enjoy the
sights and fantasize about a couple of the hunks who
caught my eye.

While I was lost in my thoughts, I felt someone come up
from behind. Before I could turn around, a hand
caressed my ass and another was wrapped around my
chest. A man pressed against me from behind. I tensed
up, near panic, and looked around for Anne, but she
was across the room.

The stranger behind me licked my ear and whispered,
“Hello. What have we here: a pretty little chicken, a
cherry ripe for picking. I want your ass tonight, sweet
thing, and I mean to have it.” I tried half-heartedly
to squirm away, but his forearm, beautiful and
muscular, barred my escape.

“I’m here with that woman,” I replied. “She needed a
guy to get her in. She’s just doing some interviews.”

My captor was not impressed. “I saw who you came with,
but she ain’t who you’ll be leaving with. No, boy, you
and I both know you WANT to be here. You’re a bottom
man, a little butt boy, and I’m gonna teach you
everything you need to know about pleasing a top before
this night is out.”

With that he let go and stepped away. I turned around
to get a look at him as he walked around the bar. From
behind he was built like a Greek god — six feet tall,
rock-solid muscles, a handsome tattoo on his chest and
others around each bicep, dirty blond hair under a
cowboy hat. He wore work boots, leather pants, and a
harness. Studded leather bands adorned his well-defined
biceps and thick wrists.

Then he turned toward me and I saw that his face was as
beautiful as the rest of him. His eyes were grey and he
had a sexy stubble of beard. Our eyes met for a moment
and I involuntarily ran my hand thru my hair, a
flirting gesture I had seen many women perform.

Then I tried my best to ignore him and my surging heat
and desire to have him take me in any way he wanted. I
looked away and checked out the other patrons. But
every few minutes he’d pass by me, rest his hand on my
butt, and even kiss my neck. Soon I stopped protesting.
I realized I had to get out of the place soon or I’d be
at his mercy and begging him to do whatever he wanted.

Anne was nowhere to be seen, so I decided not to wait
for her. I paid for my drink and headed for the door.
My gorgeous admirer stood between me and the exit, a
half-smile/sneer on his face, staring at me. I dropped
my eyes but I was turned on by his gaze and felt like
teasing him, too. Walking with one foot directly in
front of the other, I wiggled my hips and ass.

As I tried to pass him, he grabbed me. Before I knew
it, he had pressed me back against the wall, my arms
pinned behind me, his body pressed close to mine. I
could smell the intoxicating aroma of his leather garb.
His thigh found its way between my legs and my cock
stiffened even more. I was overwhelmed by his strength
and manliness, his steely grey eyes just inches from
mine. “What’s your hurry, pretty boy,” he snarled.
“You’ve been teasing me with your little ass all night,
and now I want it.”

“Let me go,” I protested weakly. “I’m not even gay.”

“Then why are you still here?” he grunted. And then his
mouth met mine. I tried to squirm away, to keep my lips
closed, but I was helpless in his grasp. My inner
desires, now bursting to the surface, took over. I
stopped resisting his kiss and opened my mouth in

His tongue entered, the most intense, deepest kiss I’ve
ever experienced, one I never wanted to end. Giving in
to the moment, I sighed in pleasure and relief. With
that he released his grip on my hands and embraced me.
I made no effort to push him away – no, instead my
hands began to explore his body, trace the incredible
muscles on his bare arms.

As we kissed I sensed someone watching. I broke our
deep lip-lock for a moment and turned to catch Anne
staring intently at us, with a knowing look. She winked
at me and smiled. I said to her, “I think I’ve found
what I need here.” She replied, “The two of you look so
sexy together. Do you mind if I watch what happens
next?” A shiver of excitement went down my spine.

My new Adonis led me by the hand through a door in the
back of the bar and down some dimly lit stairs, Anne
trailing behind. We had to squeeze past men making out;
one cute guy was down on his knees happily sucking the
cock of an older teddy-bear type.

I realized I did not even know my companion’s name, so
I asked him. “In here they call me Drummer,” he
replied. “And we’ll call you Sweet Lips, because you
have such a pretty mouth.”

We continued through a corridor with many small rooms.
Some of the doors were closed, but through the open
ones I saw male couples or groups engaged in all manner
of hot man-to-man sex. I licked my lips and trembled
with anticipation.

Finally, Drummer found an empty chamber. Inside, under
a bare light bulb, I saw a mattress covered with cum
stains and a few pillows, the walls fully mirrored.
Maybe not the most romantic spot to be deflowered, but
I was too turned on by the whole experience to care.
Drummer wasted no time. He kissed me fiercely, then
pulled back and gazed down at me. “On your knees, Sweet
Lips. Let’s see what that mouth is good for.”

I kneeled before my top man. I rubbed my face around
Drummer’s crotch, inhaling again the delicious scent of
leather and sweat. With my tongue I traced the outline
of his dick and his balls, then I started lapping. I
felt Drummer fumbling with something and suddenly a
leather band went around my neck. He ordered me to look
in the mirror.

The image of myself wore a studded black dog collar; he
held my leash. I had never seen anything so sexy in my
life. “Thank you,” I murmured.

He yanked the chain up so our eyes met. “Say ‘Sir’ when
you speak to me, Sweet Lips.”

“Thank you, sir,” I replied, happy to submit, and I
dropped my eyes. I resumed licking his crotch and was
rewarded as the growing bulge showed his cock

From somewhere within me a moan arose, my lust
overwhelming all self-restraint even though Debra was
right there. “Please, sir, let me taste your cock,” I
heard my voice begging. Drummer grunted his approval
and I pulled down his zipper.

My reward was a beautiful piece of man-meat – his tool
was a good deal longer and somewhat thicker than my own
five inches, and it curved up. The mushroom head
glistened with his pre-cum. I grasped his cock and
stared at it for a moment, finally savoring the
sensation of a handful of hard male dick that I had
dreamed about for so long.

Then I started to pump Drummer’s dong and brought it to
my lips. I ran my tongue back and forth across the tip,
reveling in my first taste of jism. Right away I knew I
was hooked for life. It was delicious!

I took more of Drummer into my mouth and heard him
grunt his approval. His rough hands on the back of my
head forced me to swallow more of his manhood, until he
hit the back of my throat and I started to gag.
“Breathe and relax, boy,” he commanded me. I nodded and
followed his directions. I couldn’t get all of him into
my mouth, but he seemed quite satisfied with my first
effort. Sometimes I bobbed up and down on his dick;
then I’d stop and he’d fuck my willing mouth.

From his moans and quickening thrusts I realized it
wouldn’t be long before I was rewarded with my first
load of warm, creamy spooge. Drummer’s body tensed, his
head went back, and then his dick pulsed in my mouth
and spurts of man-cream flooded my throat as I heard
him roar his pleasure.

I gulped eagerly, trying not to loose a drop, but a
little seeped from the corner of my mouth. Then he
eased his softening shaft from my mouth and rubbed it
around my face, a trail of cum anointing me into the
world of cock-suckers.

“Congratulations,” Debra said softly. “You did that
like a natural.”

Drummer pulled me to my feet by the leash and kissed me
deeply, his cum and our saliva mixing. Then he directed
me to strip and kneel on all fours on the mattress. As
I obeyed, he removed his leather pants, so he was just
wearing his harness, studded bands, and boots. On the
floor was a bowl filled with condoms and lube. Drummer
knelt behind me.

Then he smacked my bare butt, hard, and I yelped in
pain and surprise. Quickly, though, I realized my
mistake. “Thank you, sir,” I gasped. He spanked me
again. My cock had gotten even harder. Then I felt his
tongue on my behind and in my crack. He found my butt-
hole and gave me my first rimming. The sensation of his
tongue, as it penetrated my shit chute, was electric,
and it sent hot flashes directly to my rigid dick.

After a few minutes of this intense pleasure, Drummer
paused to open a tube of lubricant. He greased up a
finger and inserted it in my waiting ass. I took him
easily. A second thick finger soon followed, and by
then I was groaning with pleasure and dying to be
fucked. “You want it, Sweet Lips?” Drummer sneered,
mocking me. “You want my big cock in your cherry ass?
Just like I told you when you first got here.”

I looked behind me and saw that he was erect again. He
paused to sheath his dick in a rubber. Now I begged for
it. “Yes, sir. Please, sir. I need your cock, I need it
so bad – like I’ve never needed anything.” I couldn’t
believe I was saying these things, not with Anne still
standing there, but I didn’t care. For me at that
moment nothing in the world mattered but to feel
Drummer’s man-meat inside me.

He kneeled behind me, spread my ass cheeks with his
strong hands, and pressed the head of his dick against
my butt-hole. I felt the pressure of the slick
mushroom-shaped knob and winced at the burning
sensation. “You can do this, boy,” Drummer coaxed.
“Relax and push back on me.”

“Yes, sir, I’ll try.” He pushed harder and I felt a
stab of pain. Despite my lust I tried to pull away.
“Ow, no, it hurts too much. You’re just too big.”

Drummer slapped my ass, hard, and yanked on my dog
collar to remind me of my position. “There’s no turning
back, Sweet Lips, if you want to be my bottom boy.” He
instructed me to breathe deeply and push back. His
greased hand went under me and began to stroke my stiff
man-meat. Suddenly, with an odd rippling sensation and
soft sound, his dickhead surged passed my sphincter and
into my back passage.

“Oh, God, yes, yes,” I groaned, overwhelmed by the most
intense pleasure I had ever experienced, radiating out
from my ass so that my whole body trembled. For the
first time I really knew what it meant to “take it like
a man.”

Drummer went deeper and deeper until I felt his cock-
hairs brush my ass cheeks. He leaned forward and I
turned my head to tongue kiss him over my shoulder,
sealing our moment of intimacy forever. “Thank you,
sir, thank you for taking my cherry,” I murmured
between kisses.

Drummer pulled out slowly, leaving just the head of his
shaft inside me, then pushed in again. He repeated his
strokes, sometimes faster or slower, and each thrust
sent a different kind of wave thru my man-pussy. I had
never dreamed that a cock could create so many erotic
thrills as it penetrated another human being. He
pressed a thick finger against my lips and I sucked it
hotly, fantasizing it was another cock.

Anne came over to me and rested her hand on mine. I
smiled at her and said, “He’s fucking me, Anne, he’s
really fucking me. It’s incredible. Why did I wait so
long? This is the manliest thing I’ve ever done.” She
gave me a little peck on the cheek. “I understand. You
belong here now.” She told me she was leaving and to
have fun – as if I needed the advice!

When she had gone, Drummer pulled my leash to lift my
head and whispered in my ear, “No more women for you,
boy, right?” “Yes, sir,” I eagerly replied, knowing I
had crossed the line into male sex for good. He sneered
in triumph, “You’re a bottom man who’ll take any cock
up his ass. You’re a faggot, and you love it.” Now when
I heard him use that word it made me feel warm and
excited, and I rejoiced in my new, true identity.

Drummer reached beneath me and began to stroke my cock
in time to his thrusts. His hand was coated with lube
and felt so smooth as he jerked me off. Before long,
all the sensations – Drummer’s thick dick plowing my
butt-hole, his coarse beard stubble rubbing against my
shoulder, my glimpses of our fucking in the mirrors,
his tongue probing mine, and his hand pumping my cock –
sent me over the edge, bucking into a mind-blowing
orgasm way beyond any sexual peak I had ever

I heard a voice crying, “Fuck me, sir, yes, fuck me,
oh, I’m cumming, yes, YES!” and realized it was my own.
Drummer gripped me tightly, buried to the hilt, as my
ass convulsed around his dick. My arms collapsed, and
my face rested on my leather wrist bands. “What a
ride,” he chuckled as I lay motionless and exhausted.
“Thank you, sir,” I replied.

Though I was spent and satisfied, Drummer still had to
take care of his needs. He pulled himself from me,
leaving me empty for a moment, and turned me onto my
back. When he rested my ankles on his shoulder, I
realized I was about to be fucked like a woman. A
thrill of excitement shot through me as I felt his
dickhead press on my waiting fuck-hole. He eased right
in this time.

I groaned as the sensations – the fullness, the warmth
– again washed over me. I loved being able to play with
his rock-hard stomach and his perfectly formed chest,
to run my small hands over his thick wrists, my fingers
tracing the metal studs on his wrist bands, and up his

I pinched his nipples and smiled at the reaction I
provoked, for Drummer began to long-stroke my ass.
Enjoying the new pleasure of letting my partner control
the pace of our fucking, I clenched my ass muscles when
he was deep inside.

I felt like a slut and I started to talk like one. “Use
my ass, sir. It’s your boy-pussy. Fuck me all night,
sir, never stop fucking it. It feels so good. More,
sir, give me more.”

His thrusts became faster, more urgent, more needy,
until I felt one final great surge that I thought would
split me apart. Pressing my legs down against my chest,
Drummer kissed me deeply, his tongue plunging into my
throat. I imagined the jets of his hot cum shooting
into the rubber deep inside me, the pulses slowly

Drummer went on kissing me for a while. I figured we
were done, but he surprised me. “You were so good,
Sweet Lips, now I’m going to introduce you to some of
the other real men here. You’ll service them next.” I
meekly agreed. Truth is, I was still so horny, I needed

Drummer hooked my leash to a nail and left me naked on
my knees. Although a couple of cute guys looked in, the
leash told them I was someone’s property and they left
me alone.

Two minutes later Drummer came back with two men. One
was a gorgeous surfer blonde who wore work boots and a
studded leather ring around his cock and balls, the
other a bearded, older man with a round belly, powerful
arms and thighs, a leather harness, and a very thick
dick. Drummer introduced them: the blonde was “Beach
King,” the bearded gentleman was simply “Daddy,” which
seemed apt.

Daddy took my leash and order me to lie on my back on
the mattress. Without any preliminaries, he proceeded
to straddle my chest and grip my head with his strong
hands. “I hear you’ve developed a taste for cock-
sucking, Sweet Lips,” he said, his voice deep and
commanding. Then he shoved his half-hard cock between
my waiting lips. I opened wide to pleasure him.

He thrust his man-meat deep into my throat, nearly
gagging me. As I sucked furiously, his dick became
stiff and oozed salty pre-cum on my tongue. I was able
to run my hands along the backs of his large, muscular
thighs, an incredible turn-on.

Meanwhile, having slipped on a rubber, Beach King
lifted my legs, pressing them against Daddy’s back, and
probed my shit chute with one finger and then another.
It was a strange sensation: pinned under Daddy, I
couldn’t resist even if I had wanted to (and I sure
didn’t want to object, as great as those fingers felt).
I couldn’t even see my next anal lover.

Then I felt the bulb of Beach King’s cockhead pressing
against my sphincter and heard him grunt as he entered
me. He slipped in easily, deeply, for my back passage
was now used to man love. I could feel his cock ring
with its studs rubbing against my ass cheeks with each
inward thrust. Moans of ecstasy escaped my throat,
muffled by Daddy’s cock.

I was dimly aware that Drummer had come over to the
mattress. His feet planted on either side of my head,
he stood over me and offered his cock to Daddy, who
swallowed it eagerly. My own dick was rock hard again
from the friction of Beach King against my prostate.
The room was alive with the sound of rutting men in
heat and my almost-girlish moans; the smell of leather
and sweat mixed with the funky aroma of my ass as Beach
King plowed me for all I was worth.

For me, who before this night had never had sex with
more than one woman at a time, the entire scene was
from somewhere beyond my wildest fantasies. Beach King,
unsnapping his cock ring, came first, giving me what I
wanted most, a throbbing dick shooting wads of jism
into a rubber buried inside me. Drummer followed,
filling Daddy’s mouth with warm spooge, some of it
dribbling down into his beard.

Daddy pulled himself from my mouth and ordered me to
stand up. When I moved too slowly on my trembling legs,
he turned me around and spanked me. “Thank you, Daddy,”
I promptly answered, now well-schooled to the
discipline I deserved. He led me off the mattress
toward a mirrored wall and ordered me to stand with my
legs apart, arms braced on the rail in front of the

While he wrapped his tool in protective latex, I looked
at myself in the mirror, cum on my face and hair, and
saw a stranger gazing back, eyes glazed over with lust,
a creature devoted to carnal pleasure. Yet I knew this
was the real me, and I smiled.

Encouraged by Drummer and Beach King, who stood next to
us with their arms around each other, Daddy stood
behind me and prepared to give my willing ass the love
I craved. The large bulb of his dickhead pushed against
my anus. Though I had taken Drummer and Beach King,
neither small, I hadn’t experienced anything the size
of Daddy’s piece. “Oh, it’s really big, sir,” I winced.
“I don’t think I’m ready for it.”

I should have learned by now that leather tops do not
take no for an answer. Three sharp whacks on my
backside brought tears to my eyes. “What did you say,
queen?” Daddy barked, and yanked on my leash. I
apologized and begged him to give me the fucking I
needed. He pressed his man-meat against my anus while
pumping my dick.

Again I felt, almost heard, the odd rippling sensation
as my back passage stretched to accommodate the
enormous intruder. I gasped when the head eased past my
sphincter and heard Daddy mumble, “Good boy, Sweet
Lips, take it in slowly.”

Though Debra had left, I imagined her staring at me
again, shocked at what she had caught me doing. Somehow
that thought aroused me enough so I could relax to take
Daddy in. He eased in very carefully, pausing often to
let me adjust.

“God, he’s a tight one,” Daddy boasted to the other
men. It thrilled me to accept the challenge of being
fucked by Daddy while these beautiful, macho men looked
on. I gave voice to my delight. “Ohhh, Daddy, you’re
incredible. I never felt anything so wonderful in my
life. I want all of you, sir, please.” In a few
minutes, I felt the hairs of his crotch scratch my ass
cheeks – he had buried himself inside me!

Daddy began to plunge in and out. He went slowly for a
few strokes, then rapidly, then slowly, concentrating
on his own pleasure. I felt like the well-used fuck
slut I had become, and that thought excited me. Nothing
mattered to me but pleasing Daddy.

Sometimes he’d pause when he was deep within me and
rest his enormous bulk on my back, his warm, round
belly pressed against me. Then he leaned back and said,
“Get to work, fag, and show me how you can use that
little butt-hole.” As he held still, I began to bounce
forward and back on his shaft, grunting each time he
penetrated me to the core. Drummer and Beach King
coaxed me, praising me for being such a terrific boy-

I reached beneath me to gently stroke, tug, and fondle
Daddy’s heavy balls. That seemed to send him over the
top. He pushed me forward, my face just inches from the
mirror. Daddy thrust hard and fast, his balls slapping
sometimes against my thighs, and finally gave one last
lunge that felt like it would come right through me and
out my throat. The heavy pulsing of his cock, the
shuddering of his body, and his heavy sigh told me that
I had brought my third man-lover of the evening to
orgasm in my ass.

When Daddy slid himself from me, my clenching ass
muscles were reluctant to let go. I felt satisfied but
empty, and I knew that the void would have to be filled
again soon. Each of my top men kissed me tenderly. A
look at the clock told me it was past two in the
morning – I had been sucking and fucking for more than
three hours.

As I pulled my leather pants on, I thanked them for the
best night of my life. Drummer told me he expected me
back again the next night to continue my education.
“What more is there to learn, sir?” I asked innocently.

“Tomorrow,” he replied, “I put you in the sling and you
learn to take my fist.” As he held up his clenched hand
to my face, my eyes widened in fear and lust, but I
knew my place.

“Sir, I’ll come back tomorrow night.” And so I did.

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