First Time - A True Story

by Scootercray

6 Apr 2016 6578 readers Score 8.3 (70 votes) PDF Mobi ePub Txt


In high school, I was the lonely closeted queer, the quiet outsider. I joined the swim team in my sophomore year to appease my father and a fascist PE teacher, who found that I was a good sprinter after staging an impromptu swim tryout. The only thing I liked about swimming was seeing the developing bodies and young cocks of my teammates and competitors. However, if any of them were gay, they either kept it to themselves, as I did, or hid it beneath a façade of youthful sexual bravado.

To relieve my feeling of estrangement, I would often drop in on the nearby State University campus during my lunch hour often thinking my final last three years of high school could not be over fast enough. Although I didn't know anybody on the college campus, I was more comfortable in the university surroundings than among my high school classmates, who were largely preoccupied with sports or their hormonal urges for the opposite sex. I liked sports well enough, but I didn't engage in the banter about girls. I suspected that most of the stories were bullshit anyway. There were a few girls who hung around the team, providing some with opportunities for real, exaggerated or imagined sexual dalliances. Because of my aloof demeanor and athleticism, nobody suspected my sexual orientation. I was perceived as the strong silent type who was shy with girls. That's what I thought anyway. I certainly didn't exhibit any femmy gay boy mannerisms which could get me thrown out of the house or shunned by the team.

I did pop a boner in the shower once, after seeing one of the hunkier seniors rubbing his cock to an erection. Somebody shouted, "Hey, Rolf are ya gonna jack off in the shower?"

"I got something for you right here, faggot," was Rolf's reply. He began to pump his thick cock to full erection, shamelessly masturbating in the communal shower. As an upperclassman and overall BMOC, Rolf's sexuality was never in doubt. My teammates worshipped his aura of confidence and his popularity with girls, I thought he had the face and intellect of a Neanderthal, the body of Apollo and he carried heavy lumber between his legs.

The shower room broke out into a spontaneous circle jerk with several teammates jacking off in the shower. The sight of all those stiff, young cocks being jerked off in unison was the most erotic memory of my first fifteen years on earth -- my mind still drifts back to that moment when I masturbate. I joined in the cock pumping fest and fired several blasts almost half the length of the shower, earning new respect for my length and distance. Little did they realize how charged I was by their dick pumping. We left the shower looking pretty pruney and the coach muttering about taking too long.

Sean was just sitting on a couch at the Gay and Lesbian Center reading a magazine when worked up the nerve to pop in for a look. I did it out of curiosity and a longing to make contact with my kind. My gaze was met by his twinkling blue eyes and easy smile and a friendly "Hello". Sean was a sophomore psychology major from Wisconsin. His blue eyes and blond hair hinted at his Norwegian roots. Tall and slim with high cheekbones, he was handsome but not what I would consider hunky. I introduced myself and told him that I was a local high school student. After chatting with Sean and a few others at the LGBTQ center, I felt quite at ease and began spending more lunch hours on the university campus. I was particularly fond of the erotic male literature at the center and the college library as it was fuel for my nocturnal masturbation fantasies about making love to another man.

Sean was always glad to see me and we became close friends. Despite the four year difference in our ages, it seemed that we had much in common. He didn't seem particularly athletic, but he told me that he was a pretty strong swimmer. When he invited me to the college pool to swim laps with him after school, I quickly accepted.

Sean was slightly taller than me at the time but thinner. While he was a good swimmer, he was not in my class as a sprinter. He swam laps in the early evenings to relieve stress and to work out. After our late afternoon swims, I would often follow him to his apartment where we would talk, have a beer or smoke a joint. Sometimes, all of the above. After one particularly late swimming session, we went to his apartment. I told him that I scored some good grass. He was pleased and picked up a pizza on the way to his apartment. We devoured the pizza and washed it down with Michelob. I pulled out a Ziploc baggie with four joints. We began to smoke the joints one after another while talking discussing openly gay celebrities and politicians. I passed the last bud to Sean, who took a long last drag from it. "Well, that's the last of the weed," I said.

"Another beer, Scotty?"

"No thanks, I gotta piss like a racehorse," I said as I pushed off Sean's knee to get off the couch and go to the bathroom. I felt like I just pissed half a gallon of beer because it seemed to take fifteen minutes to empty my bladder. Over my shoulder, I noticed that Sean was watching me relieve myself.

"About time," Sean said as I shook off my penis and flushed the toilet. We passed each other awkwardly through the doorway avoiding contact. I plopped down on Sean's couch and watched the ceiling slowly spin around then heard the toilet flush. I was starting to get an erection and had to adjust my inflating cock to relieve the pressure under my jeans. I looked up and saw Sean eyeing me as I was pulling my hand from my bulging groin.

"So you wanna watch some TV?" he asked sliding next to me.

"How about some music instead."

Sean got up and turned on his stereo. I heard the Beatles' "Come together" begin to play. The combination of the hypnotic beat, the alcohol, and the marijuana was making me lightheaded. I barely noticed when Sean seated himself next to me, but I could feel the heat from his slender body. He was now wearing a plain white T-shirt and shorts and I could feel the warmth of his thigh through the heavy denim of my Levi's. Sean seemed to get up, but he leaned into me and turned toward me. As our lips met, Sean rested most of his weight on me and slipped his tongue into my mouth. He began exploring my teeth and tongue. His thin blonde mustache tickled my cheek and my left hand reached under his T-shirt to rub his chest and back.

With his left hand, he pulled out my shirttails, while his right hand fumbled with my belt. My excitement heightened when I felt the hardness in his loins against my thigh. Finally, he worked loose my belt and I helped him with the zipper and the top button of my jeans. Electricity coursed through me when Sean grasped my penis, the first time anybody else had touched my erect cock. As he stroked me, I felt my pulse pounding through my temples and my cock, and especially my chest. Our breathing became deep and heavy. I lifted my butt off the sofa so Sean could pull my pants and jockeys down to my ankles. I kicked off my shoes, socks, pants, and shorts, as Sean helped me with my shirt and undershirt. I was now naked on Sean's couch and passionately embracing him. Sean quickly pulled off his T-shirt and shorts, revealing his almost hairless chest and the sharply pointed shoulders of his tall sensuous frame. Also, his rigid manhood, which like Sean, was slender and pale except for the swollen pinkish, purplish head.

We kissed again with each other's cock in hand. I let out a low moan as his hand tickled and caressed my very sensitive testicles, and he started kissing my neck then my chest and sucking on my erect nipples. Sean worked his way down my chest and abdomen while stroking and caressing my male hardness and my testicles. My breathing deepened as I felt his tongue on the underside of my cock head, and my thoughts raced as the hot wetness of his mouth enclosed the head of my penis. My body reflexively arched back in ecstasy, as Sean's skilled tongue swirled around my manhood. Sean then began licking my shaft and low hangers. He took each testicle in his mouth and began working them with his tongue. I started rubbing and pinching my nipples, as I looked down at the erotic sight of Sean engulfing my testicles with his mouth and stroking my straining cock.

With his face buried in my crotch, Sean looked like he'd sprouted a bushy mustache of teen-aged pubic hair and had an upward-pointing meaty arm appended to the tip of his nose. He stopped kneading my balls with his tongue and resumed licking my shaft from tip to testicles. Then Sean took my cock in that hot mouth and started working over the head with his tongue while still stroking the base of my cock. My grunting and moaning became louder and I started to buck my hips when he stopped and told me not to cum yet. He then drew in more and more of my cock into his mouth until I could feel his lips at the base of my cock. He bobbed his head up and down taking the entire length of my cock and finishing with a swirl at the tip. After a few strokes, my breathing became forced, shallow gasps of fire; my face flushed; every muscle tensed and tightly bundled. I ejaculated on the next half dozen downward head bobs. I had discovered masturbation less than two years ago but nothing in my auto-erotic experience matched this explosive orgasm, my first sexual experience. This was more than just another undercover wank or impromptu shower room circle jerk.

Sean lapped up the semen that leaked from the corners of his mouth and milked the last drop of me from my subsiding erection. He finished cleaning me, got off his knees and kissed me. I could smell and taste my slippery saltiness on his lips as it flowed from his mouth and I felt him grind his inflamed manhood against my flaccid member. The mix of our saliva and my male seed tasted and smelled and felt great as we twirled it between our tongues. My turn.

My clumsy, toothy initial effort was more hand job than blowjob, but Sean appreciated my enthusiastic, albeit slobbering, effort. I eagerly licked up his male spray from his abs and his smooth chest and held it on my tongue to taste it more completely before swallowing it. I was grateful that Sean had an orgasm from my freshman effort. My love of savoring the musky bleach smell, the salty taste and slickness of freshly ejaculated semen started that day. Relaxed and satisfied, we fell asleep in each other's arms.

When I awoke, it was nearly 9 o'clock and I felt that I should be going home. Sean was silently looking at me.

"I've got to be going home."

"Please stay. I want to fuck you."

I hesitated, "Okay, but I'm kind of nervous."

"Let's go to the bedroom."

We got off the sofa and I followed him to his bedroom. Sean had me lie on my stomach, then he massaged my shoulders and back. He reached into a drawer and retrieved a bottle of floral-scented oil. After pouring oil on his palms, rubbing them together to warm the oil, he resumed massaging my shoulders and back and worked his way down my buttocks and my legs. He straddled me below my butt and resumed massaging my shoulders and back again. I was very relaxed and warm and noticed his hardening penis in the crack of my ass as he leaned forward to massage my shoulders. The underside of his swollen and well oiled erection rubbed between my ass cheeks against the upper rim of my asshole. The friction was exquisite and I reflexively let out a soft moan. Sean paused rubbing my hole with his hard cock to put more oil on his hands and spread my legs. I felt fingers rubbing from my asshole, across my perineum to my balls and back. My dick was rock hard and I needed to adjust it so it could be more comfortably positioned beneath me. Sean shifted his position and a jolt of electricity shot through me as his tongue swabbed my asshole up, down and around. He started to push that magnificent tongue into my hole and I started moaning and bucking to get his tongue deeper into me. Sean replaced his tongue with a finger. At first, rubbing outside my asshole and then penetrating my sphincter, which didn't feel so good. He was able to easily slip his thin index finger into my ass but the feeling of pleasure was being replaced by anxiety.

Sean held his finger in my ass for a couple of minutes so that I could get used to the sensation, then started to fuck me with it. I wasn't getting any more relaxed by the finger fucking. He had me get on my hands and knees doggy style and reinserted his finger. I still couldn't get comfortable with it but he persisted in finger fucking me. Sean stopped finger fucking me and used his tongue to relax me and it worked. This time Sean used two fingers to fuck me and I started to loosen up, especially as my nerves calmed and I was responding to the massaging of my prostate. More tongue and then I felt his hands grab the side of my hips and the head of his manhood against the entrance to my asshole. I panicked and clenched as I felt the pressure of his penis pushing into me. Sean stopped and worked to relax me with his tongue and fingers again. He tried entering me again but I tightened up again. Rinse, repeat, the same result. Sean managed to get the head of his penis through my sphincter but I had tightened up so much that it was very painful and I was afraid of tearing if he pushed further. No additional amount of lube was going to work. Finally, we gave up.

"I'm sorry, Sean, I'm just too nervous."

"That's Okay. First times can be tough and I don't want yours to be a bad experience."

Sean laid on top of me and we kissed.

"How about you fuck me?"

"Umm, sure."

I felt bad about not being able to receive his manhood while he was willing to take mine into his body. He started kissing me again and worked his way down my torso and stomach, making sure to suck each nipple to an erect state. He tongued my cock to a full erection and deep-throated me a couple of times before applying a liberal amount of oil to it. I wished I could do the same to him without gagging. He straddled my erection and rubbed it across his asshole and perineum which felt really good. He momentarily stopped to flick the pre-cum from my penis slit with his tongue and to finger himself. After a few deep breaths, he positioned himself over my erection and lowered himself onto it with one hand guiding it to his butthole. As excited as I was, I kept still as he pushed the head of my cock through his sphincter and slowly engulfed the rest in his ass. It felt very tight and hot around my cock. His breathing was measured but deep and he let out a low groan when I was completely inside.

"Are you okay?"

"Yeah, I need a minute to get used to the size."

"Does it hurt?"

"No, it feels great actually."

I wished I could derive the same pleasure from riding his cock instead of anxiety and pain. Sean began to rock back and forth on my manhood and then started to pump my cock in and out of his ass.

"Ahhh, fuck me."

I complied and our strokes lengthened until my cock was almost completely out and then back in. We established a mutual rhythm and I moaned with pleasure as Sean's tight, educated sphincter worked my cock. He introduced a grinding motion when fully bottomed on my cock. His groans of pleasure were becoming yelps and barks.

"Are you ... ahhh ... ready to come?"

"No, I can keep gong."

"Because ... because ... uh ... uh ... I sucked you off?"

"Yeah," I replied

"Fuck me doggy style." Pause. "Fuck me doggy style"

We stopped and I reluctantly pulled out of his tight manhole. It felt like I could have kept fucking him for hours. More lube and Sean got on his hands and knees as I positioned myself behind him with my cock twitching and spasming, eager to re-enter its new found home. I put the head of my penis against Sean's beautiful, pink butthole.

"Don't come in me."

"Okay. You want me to stop before I come?"

"Let me know. I want to face you when you come."

I started pushing my cock into Sean slowly, he pushed back forcefully and took my cock all the way in with a single backward lunge. We quickly re-established a cadence with a grinding in and out stroke. Sean resumed barking and yelping in pleasure. My moans became louder and my breathing heavier as I closed my eyes, giving into the raw sensation of sex. Ahhh, sensations felt so good with this hot man wrapped around my manhood in its full glory.

"I'm getting close," I announced.

I stopped fucking when Sean clamped down hard on my cock and I reluctantly pulled out of him again. Sean got on his back and pulled his legs back toward his shoulders. With more lube applied and I pushed his legs back further, his well-worked anus was presented to me and ready to receive my cock now leaking clear pre-cum. My excited manhood slipped into Sean easily and he let out a sigh as my balls rested on his ass. I pinned his legs over his shoulders, started fucking and leaned in to kiss him. In this position, Sean was immobilized and my fucking provided all the impetus. My strokes were longer, the cadence slower. Face to face, I penetrated Sean as deeply as physically possible, our teeth and tongues intertwined and wrestled for dominance. My tempo quickened as my strokes shortened and increased in force, my balls were ready to explode. The headboard banged against the wall with the authority generated by our rapturous exertion.

I loosened three ropes of semen, not as much as my first orgasm but the spasms were more powerful and mind-blowing. Enormous sexual energy transferred through my seed into Sean. Our mouths locked in a desperate exaltation. Sean wrapped his legs tightly around my waist. At that moment, we became a single melded being, a primal lover, until my erection subsided and withdrew. The sheets were drenched in our co-mingled sweat. We showered, tenderly washing each other's backs. In the shower, Sean bent over and spread his ass cheeks. I could see the seed I planted oozing from his haunches. I resisted the urge to get on my knees and lap up my transferred essence.

"Stay with me tonight," Sean pleaded.

"Okay," I agreed.

Sean's alarm sounded at 6 o'clock. He reached over me to silence the alarm and we spooned enjoying the warmth of our bodies. I pushed my ass against Sean's groin as he nuzzled me, wriggling and grinding to stir his cock. I reached back and grasped his rising cock to stroke it. I thought about jacking him off as a wonderful way to start his day. Sean started fucking my hand and I turned to kiss him.

"I want to try to fuck you again."

I nodded and he stopped fucking my hand turned me on my back and reached for the lube. He applied lube to his now fully erect penis and my asshole, taking care to work in one then two fingers. This time I was fully relaxed and easily accepted a third finger. Sean pushed my legs back and went down on my ass aggressively with his tongue. I moaned with pleasure at the muscular tongue caressing and probing my asshole. More fingering and tonguing as I closed my eyes and let the waves of pleasure roll through me. Sean dripped lube directly onto my asshole, the coolness of the lube soothed me. He pinned my legs over my shoulders and I was completely open to his manhood. I took a deep breath and exhaled as his cock pushed into me.

"Push out like you're taking a shit," he commanded.

The head of his cock cleared my sphincter with only a slight pang. Another breath and a couple of inches were in me. I nodded that I was good to go further and he let his weight bearing down on me until his manhood was buried to the hilt, I was completely at his mercy. Nuts on butts. I felt the pressure of his cock in me, but there was no pain this time. I wrapped my arms around his head and pulled him in to kiss him; he proceeded to fuck me. Sean built his pace steadily while long cocking me. The frisson from the sliding sensation against my prostate was fantastic and I moaned with joy. The ecstasy surging in and out of me intensified as Sean's pelvis met my ass with greater force and frequency. His breathing became labored and his grunting and moaning louder as he approached orgasmic release. Sean's body tensed and he bucked hard into me as he filled my core with his seed. I felt cum drip out when Sean withdrew his manhood and collapsed atop me. I was kissing his neck as the weight and heat of his body covered mine, his wet and flaccid cock pressing against mine.

My body relaxed and a feeling of satisfaction washed over me as I caught my breath. I wanted to retain Sean's male essence in my body as tangible evidence of our coupling. With that big, sloppy, sweaty fuck, I joined the Ancient Brotherhood of Man. My body belongs to the Brotherhood forever.

I would learn to be a proficient cock sucker and Sean introduced me to his friends and to other lovers.

by Scootercray

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