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My Man Ass Cherry

My Man Ass Cherry

       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 surrender.

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 hardening.

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 experienced.

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 arms.

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 receding.

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 more.

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 mirror.

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- whore.

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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