I had reached my twenty fifth birthday and outwardly my life looked rosy. I was living in Chicago with a freshly minted MBA, a fast track career, nice apartment and clothes and was making new friends. I should have been happy but sexual confusion left me with a feeling that something was missing in my life.
I grown up in a conservative family and community where gay men were stereotyped as prancing, effeminate queens who liked decorating their homes and listening to Broadway musicals. I had no outward affectations of gayness and had no trouble getting dates with girls. I did not consider myself to be gay even though my masturbatory fantasies were largely ones in which beautiful men screwed women and in which my attention was focused on the man's nude sweating body fucking a woman into ecstatic oblivion. If I had to honestly describe my sexual orientation I would have to say "Confused".
Sex did not live up to the hype but I assumed it was the lack of talent or experience on the part of the girls I dated. In high school and college I moved through many relationships, none of which lasted long. I mostly avoided women who had the reputation of being loose and easy. There was less pressure to fuck them right away. I was not much interested in sex with women but I knew not having a girlfriend would lead my parents to suspect I was gay.
Throughout high school I competed on the school swim team. I won a few championship medals and enjoyed the competition and self discipline demanded of a swimmer but mostly I loved the male comradery. The woman on the team were great buddies. I thought of them as sisters and liked going out with them as friends. Stories of these "dates" kept my mother happy with dreams of planning my wedding. The men were another story. I loved them all dearly, dreamt of them, but quietly feared that if they ever knew of my sexual curiosity about them I would lose their friendship. I occasionally allowed dreams of bedding one of my team mates to rise to the level of consciousness but in less lust crazed, more rational moments, I would recognize that a good roll in the hay was not worth being permanently ostracized by my teammates.
Away at college I continued to swim competitively. I was becoming increasingly aware of my sexual curiosity toward men. As a swimmer I spent several hours a day around nude or semi-nude men. Dreams of the smooth, perfectly developed bodies haunted my nights though I still did not think of myself as gay. Nobody on the team ever made a sexual advance toward me and I was not daring enough to make one myself. I, like most young men, reveled in the liberation from the confines of my parent's house. I made new and different sorts of friends, one of whom I ended up in bed with in a mutual session of oral sex. The physical act was deeply satisfying but neither of us had the maturity to handle what might come next and it caused an unspoken, mutually acknowledged end to our friendship.
In graduate school I ran and competed in triathalons to hold onto the buff physic that had developed from my years as a swimmer. I spent a lot of time in the gym where my workouts invariably ended in the steam room where I discretely eyed the other nude men and on a couple of occasions engaged in some mutual jack off sessions. These experiences left me feeling a little sleezy, like the overweight trolls who prowled the locker room looking for jack off partners, but at the same time I liked the attention my body commanded. I was increasingly being forced to admit to myself my lack of desire for women and my lust for men but could not identify with the gay community. When the confusion was to much to handle I could always through myself into my studies.
Once settled in Chicago I made no effort to enter the city's large gay community. I knew I liked sex with men but did not identify with people strictly on the basis of my sexual urges. Moreover, although I could appear personable enough I was inwardly quit shy. I had no idea how to approach a stranger, male or female, in a bar, strike up a conversation and get the target into my bed. It seemed my right hand was destined to forever be my best friend until Jim changed my life.
I had been working with the company for a couple of weeks and was still getting settled in when we were introduced. I would be working closely with Jim although he spent a lot of time on the road, meeting with customers, selling the company's services. After a long morning reviewing business we decided to break for lunch in a nearby bar . Jim and I instantly bonded. He, like me, had been a college swimmer. We liked the same sports, books and movies. He was light and jovial up front but inwardly he was a deep, thoughtful person.
I was immediately struck by his physical appearance. Two years older than me he was the masculine ideal. The sort of guy you see pictured on the front of Men's Health. He had a classic broad shoulder, tight butt swimmer's build. His dark hair was perfectly styled. His strong, sculptured facial features commanded your gaze. There was no secret about the reason for his success in dealing with woman customers. He looked incredible.
As we talked we found we both missed our swim team days and retained a strong desire to stay in shape. Being new in town a queried Jim about good swimming pools. The one's I had seen so far were largely inhabited by overweight sixty somethings in baggy trunks, more interested in dog paddling than training. Jim assured me that his health club pool was large, clean, rarely crowded and the users were young, athletic, serious swimmers. He extended an invitation to be his guest at the club after work the next day. I had not swam much in the past several months and I was filled with anticipation as I packed my gym bag that morning.
The health club was new, expensive and located near the office. The clientele seemed to consist largely of attractive, athletic twenty and thirty somethings though even in this crowd Jim's physical beauty stood out. We entered the men's locker room where we choose adjacent lockers and began to strip.
Jim hung his suit coat in the locker and then sat down to on the bench to remove his shoes and socks. Next he took off his tie and his shirt. I tried not to be obvious as I glanced at him, eager to satisfy my curiosity about his body. His torso was tanned and beautifully muscled. His pecs were covered with a light coat of hair which extended in a thin line down his washboard abs. He next took off his pants and hung them up. With his back to me and dropped his boxer shorts.
I could not see his cock but his ass was a dream. A light dusting of hair came out of the crevice between his perfectly formed buns. My heart rate increased as he reached into his gym bag and pulled on a brief speedo. I had done the same and was ready to swim.
As he led me to the pool I glanced at our reflections in the locker room mirrors. We didn't make a bad pair. I was well tanned and had lost none of my swim team muscle tone. Unlike Jim, my body was smooth. My light brown hair had been bleached blond by a summer in the sun. Like Jim, my token piece of clothing met the legal requirements without leaving much to the imagination. Both of us displayed large bulges in the fronts of out suits.
We took adjacent lanes and started our work out. Side by side our powerful bodies sliced though the water as we did sets of the crawl, breast stroke and butterfly. After an hour Jim signaled a halt. I was tired but invigorated by the work out. I followed Jim to the exit where we grabbed towels from a stack by the door and dried our selves. Tossing the towels in a bin we returned to our lockers. Jim opened his locker and tossed his goggles inside. Next he pulled off his suit, wrung out the water into a floor drain and then flipped it into the locker and closed the door. Assuming we were heading for the shower I did the same.
Jim looked at me and asked if I was in a hurry. I had all evening. He had an hour to kill before a date with a girlfriend and wanted to hit the steam room. I followed Jim through the locker room. I could not help but staring at his body. He was deeply tanned except for the outline of a brief suit. The whiteness of his ass only enhanced its perfection. He passed a stack of towels but did not pick one up, instead entering the spa area buck naked.
The spa area, which had a steam room, sauna , jacuzzi and showers was filled with a couple dozen men. All were reasonably attractive. Not a single one had a towel modestly drawn about his waist. Full nudity was the norm. We entered the steam room and sat down on a bench. I glanced through the clouds of steam. I could make out at least six mist shrouded figures.
I stole a glance at Jim. Steam and sweat were glistening on his skin. In the intense heat his large balls were hanging low.
His cock was long and thick and, I estimated, 8-1/2 inches when hard. Mine, at nine inches full, was longer but about the same thickness. He sat casually back against the wall with his legs apart and his attributes on clear display. As I looked through the clouds of steam it seemed that a couple of the other men were stealing peaks at us.
After a few minutes Jim stood up and began stretching. He put his hands up against the wall and began pushing against it.
The hamstring stretch highlighted his perfect ass. He then dropped to the floor and began doing push ups. As I watched the muscles flex on his beautiful, sweating back I felt dizzy with confused feelings. My sexual curiosity about him was strong but what if he knew and was turned off by it. Through the clouds of steam I saw one of the other men watching Jim and trying to look casual as he held is hands over his erect cock. My head spun. Coming in without a towel was a mistake but what could I do. Nudity was a de facto requirement in the spa area. My cock was starting to harden. I tried every mental trick to distract myself from the gorgeous flesh on display. I could not get my cock completely flaccid but at least it was not fully hard. I was terrified that Jim would notice and I'd loose my chance to win his friendship.
After fifty push ups Jim rose, panting lightly, and said "Let's cool off." As we left the room I thought I saw him trade glances and a slight smile with the stud with the hard on. In the shower I turned the water to cold and let the bracing stream pour over my body. The water temperature was heart stopping but at least it deflated my cock. I hoped Jim had not noticed my semi-aroused state. Jim called "Sauna Time!" as he exited his shower stall.
The sauna was empty when we entered. The heat was even more intense than the steam room. I took a seat on the lower bench while Jim lay down on his back on the upper bench on the opposite side of the chamber. He folded his hands behind his head and lay back. We chatted about me getting a club membership and his upcoming date. Then Jim fell silent and closed his eyes. I closed my eyes for a couple of minutes and then looked up at Jim. Sweat was streaming off his body and dripping on to the lower bench. His chest rose and fell lightly with his gentle breathing. His cock, oh God! His cock was starting to thicken and rise. What was he thinking about? The woman he would almost certainly fuck tonight? The man in the steam room? What could I do? I considered fleeing back to the cold shower but longed to see if my new friend's cock would become fully hard. At least the heat in the sauna was so intense that I could not have gotten an erection even if I wanted to.
Just then I heard the door open and the man from the steam room entered. Jim looked up, smiled at the man and said "How's it going?" He sat up and moved to the lower bench while the new arrival sat on the sweat drenched upper bench. Jim and he exchanged a few words about work outs. From their conversation it seemed that the man was a regular in the club and he and Jim were vaguely acquainted with one another. So that was it. Jim had nodded at man while leaving the steam room because he was friendly. There was nothing sexual about it. Jim's cock was now flaccid.
Jim announced he had to go and left the sauna. We both took long showers and dressed. Then, while Jim left to meet his lady friend I spoke to the club sales rep about a membership. That night, alone in bed, I replayed the whole locker rook scene as I whacked my torpedo. Cum sprayed all over my face as I ejaculated to visions of Jim's naked sweating body.
The next day Jim left town for a three month assignment at our Honolulu office. I worked like a fiend, ran and swam almost everyday and made a half determined effort to meet some guys through personal adds in the local alternative paper. My dates were pleasant enough but they never went beyond an initial meeting over a cup of coffee. My nights were spent alone whanking off to fantasies of Jim.
On the first day after the New Year holiday my boss announced that I was to accompany Jim to a two day meeting with an important client in Boston. I could not have been more thrilled. A successful meeting with the customer would be an important stripe on my sleeve. Plus, two days alone with the man of my dreams. I couldn't have been more happy. We were scheduled to fly out on Tuesday morning, meet with the client, spend the night in Boston, more meetings on Wednesday and then fly home that evening.
We arrived at mid-morning under a steel gray sky. We rushed to the client's office and spent the whole day giving product presentations and talking deals. The first day went splendidly. Both of us hit it off great with Chet, our client contact. We were all into triathalons so Chet invited us to his club for a swim before we headed off to dinner. Neither Jim or I had brought swim gear with us but Chet said he had extra in his locker.
The club was located in the Back Bay and reeked of old money. The members seemed to fall into two categories: people who looked like friends of George Bush and people who were friends of George Bush. In the changing room Chet opened his locker and tossed some goggles to Jim and I and started to remove his clothes. "Suits?" I asked. "The club is men only. You swim nude." I smiled inwardly. I loved the freedom of swimming naked and what better way to do it than with two attractive companions.
Chet's wedding ring and children's photos on his desk declared him off limits but he was still easy on the eye. More lightly built than Jim or I he had more of what you would call a runner's body. He was lean and well toned with a full rug on his torso. The swimming pool was a beautiful old tiled thing though disappointingly the only other men in it were old and flabby. At least I had Jim's and Chet's cocks to look at while I did my laps.
We swam for about an hour. I had grabbed a lane between Chet and Jim so it would be easier to steal glances at them under the water. The wonderful freedom of swimming without a suit and the gorgeous hunks of male flesh were making my cock semi-stiff. I stopped at the end of the lane after a brutal set of the fly. Jim swam up and stood to reach for a kick board. The board was several feet from the edge of the pool and he had to rise well out of the water to get it. A he stretched for the boad I could not help but notice his cock seemed to be slightly engorged. I shuddered to think of him next to me. So close and yet so far. It took every cock softening mental trick in the book to keep me down as we finished our swim, steamed and showered.
Work went well the next day but as I glanced out the office windows I could see a blizzard building. At 5:00 Jim and I said our good byes and grabbed a cab to Logan Airport for our 6:30 flight. We barely reached to airport in time and ran to the gate only to find all flights had been cancelled. While I stood in an interminable line to get us booked on something tomorrow Jim went to a phone to locate a hotel room. After nearly two hours in line I got us scheduled on a flight back to Chicago the next afternoon and went to find Jim. He announced that due to the storm and big conventions in town he couldn't get two rooms. We would have to share.
We managed to catch a cab to the hotel downtown. As we had worked through lunch we were both ravenous and decided to eat before going upstairs. The hotel restaurant was closed but the bar was still open and served sandwiches. We sat there for a couple of hours drinking pitchers of beer, gloating over our success and generally talking shit. With a good buzz going we grabbed our bags and headed up to the room.
Inside, Jim hung his over coat in the closet and then removed his suit coat and hung that up. Next, he opened his suitcase and pulled out a shaving kit and set it on the sink. Then he sat on one of the beds and removed his shoes, socks and then his neck tie.
Jim said "11:30. Time to get into our jammies and get some sleep." "Jammies" I responded. "I hope I don't' scare you. I don't wear pajamas."
"You won't scare me. Actually you have a nice body and I'm not getting into pajamas either. I haven't slept in clothes since I was 15. If you don't need the bathroom I'm going to get into the shower."
I assented and tried to act casual as I watched him strip off his clothes and walk nude into the bathroom. The months in Honolulu had rejuvenated his tan and he was fucking beautiful. I watched his hot tight ass wiggle has he headed into the bathroom, half closing the door behind him.
As he showered I undressed partially, leaving my pants on. After a long time he came out of the bathroom with a towel wrapped around his waste. I pulled off my pants and briefs and headed into the bathroom. I stood under the shower for a long time enthralled with the idea of sharing a room with this gorgeous stud.
I wrapped a towel around my waist and walked back into the room. Jim had turned off all the lights but the one between the beds. I was pleased he had not put on his underwear for sleeping but was still in his towel. Jim's eyes were transfixed on the television. I heard the sound of low groans and moans of pleasure. Jim was watching one of the cheesy soft core porn movies on the hotel video system.
"Ah, some quality entertainment." I remarked, trying to sound manly. "Actually its pretty boring. Want to watch?"
"No. I'd rather get some sleep" . Jim clicked off the television and walked into the bathroom. I heard him get rid of some beer. He walked back in to the room sans towel. I was sitting on my bed still covered in a towel. The site of Jim brought my cock to a semi-hard state.
He sat down on his bed with his legs on the floor facing me. "Pretty swanky club Chet has." He remarked.
"Yea. Great pool." I replied.
"Yes. I wish we had some place in Chicago where a man could swim without one of those ridiculous suits" said Jim.
"Three most useless pieces of clothing ever invented. Neck ties, pajamas and swim suits. Back when my father was on the college swim team they always trained in the buff. Of course it's better when all the guys are as good looking as Chet"
I was a little surprised at this statement. "Most guys don't want to admit another guy is good looking."
"Well, I'm not most guys" he said. "Call me what you want. I'm not afraid to say I find some other men attractive. I think in a way we are all a little bi-sexual, or at least would try it once if they had the chance."
My cock was fully hard by this point. "Have you ever done it with a guy?"
Jim remained completely casual.
"Yes. I've done a guy or two. I've always been pretty bisexual. How about you?"
I gulped. "Yeah once or twice. Be right back. Time to get rid of some beer."
I stood up and walked to the bathroom. I had been sitting in a position where he could not see my erect cock. Now there was no hiding it. The towel was nicely tented as I walked across the bathroom. I removed my towel and stood over the toilet, forcing my cock down and got my urine stream going. I concentrated on relaxing. If anything is going to happen it was now or never. I dried off the last drops of piss and hung the towel on the rack and headed back trying to act casual but making no effort to hid my nine inch glory.
Jim was sitting with on his bed with his back against the wall, his feet on the bed, his legs apart and a boner on full display.
He looked at me as I walked toward my bed. He reached out with an arm and touched me gently. I looked at him. Like a sleep walker I stood over him. He gently brushed my cock with his hand and then reached up to me with open arms. I knelt down and embraced him. He pulled me down on top of him and started to kiss me. His tongue invaded my mouth and then mine his. His rough beard scratched against my face as he kissed me all over my mouth, neck and ears.
This is what I had waited so long for? It felt to good, so right, so natural. His hands were stroking my body as if it were his own. He knew where to touch me. First he cupped my buns in his hands and then started to stroke the small of my back. I began to lick and kiss down his chest. I licked around his defined pecks and then moved to his nipples. He sighed with pleasure as I sucked on them. He rolled me over so he was on top and then started work his way down my torso. He licked my nipples lightly and then continued toward my cock. He licked my balls and cock without hesitation. The sensations were phenomenal. He did not take my cock in his mouth but kissed and licked it. He knew just where to lick. I was in heaven. My breathing became heavy. I was ready to blow when Jim sat up.
I reached out to him but he moved away. "Relax" he said. "We have all night" and moved off to lie next to me holding my hand. He started commenting on the merits of the men's bodies and how much he enjoyed touching and being touched by another man. My hardon was not subsiding but the eagerness to cum was passing. I reached over and began to stroke his cock. His eyes closed. Then, I bent down and took the head into my mouth. I almost gagged on it but my lust overcame the instinctive reflex. I started to lick the head of his cock and tried to force my tongue into the piss slit. Jim had done this to me before in my fantasies. His breathing quickened and then without warning he reached down with his hands and gently pushed my head off him.
"I want you inside me" he said. I stared at him uncomprehendingly. I couldn't believe I heard what he said. "I want you to fuck me" he said again. I gently ruffled he hair. "We'd better grease up. You're pretty big."
He stood up and walked over to his shaving kit on the sink. He reached in and pulled out a tube of vaseline and walked back to the bed. His huge cock was standing almost straight up. It was wet with my spit and his precum. His eyes were glazed with lust.
I lay on my back watching him, not sure what he was going to do. He sat down next to me and kissed me deeply. Then he said "I've never had anyone as big as you. We have to start slow." He opened the tube of jelly. He squeezed some on my cock and slowly stroked it around. The sensations of his touch blocked out everything else. Then he lay on his back next to me. He handed me the vaseline raised his legs in the air. I moved to kneel between his legs. I started to run grease around his butthole. "Get some in me" he said gently. I inserted one then two then three greasy fingers in him. Our breathing was heavy with anticipation of what was about to happen. My cock was twitching, so stiff it was painful. As I finger fucked him he moaned with pleasure. I stopped moving, leaving my fingers in him. We looked at each other. It was time.
He lifted his legs high and wide. I pulled out my hand and I lined my throbbing rod up against his love tube. I started to push in. It was hard to get in but I was too insane with desire to stop. I pushed and pushed. My cock began to open the sphincter muscle. He grimaced in pain. I held back. His breathing was labored. I pushed a little more and paused. Jim's hands clutched the sheets. I pushed again, this time with force. Jim cried out in pain as I passed the muscle. "Stop" he begged.
I was glad to. The sensation of being in his ass was overwhelming. My cock was in the hottest tightest space it had ever been in. No woman's pussy could match this sensation. If I made any movement I was going to cum and I wanted this to last forever.
We lay connected but not moving for several minutes. Jim's eyes were closed, his face in a grimace. Sweat was breaking out on our bodies. I slowly began to push gently further into him. Jim began to nibble on my ears. I turned his face to mine and we traded rough man kisses as his hands worked roughly down my back and began to caress my ass, crawling up my back to stroke my hair and then down. He pulled my checks apart and started to put to fingers into my anal canal. I thrust forward roughly. He yelped.
I started to move in and out slowly at first but once I started I could not stop. There was to much friction. I had never experienced sex like this. I was excited beyond belief but I always had good control over my orgasms. I propped myself up over Jim and kept thrusting as he started grunting. He moaned out "Fuck! This is great!" I looked down at his cock. His huge beefsteak was rock hard. As engorged as it could get, it was dark purple and precum was dripping out of it and pooling on his stomach.
The site of this drove me insane. I frantically kissed and bit all over his neck and ears while he pawed my head and back. I bent lower and bit one of his nipples hard. He screamed in pain but grabbed my ass and started trying to pull me deeper into him. I started thrusting harder and moved to the other nipple, almost chewing it off. I reared up, looking down on him. His eyes were crazed. Blood was coming off his nipples. His cock was pulsing in time with his wildly racing heart. Sweat poured from my body and dripped down into the streams that were flowing off Jim. He moved his legs from around my waist up onto my shoulders. I started to thrust faster and deeper into him. As I'd pull almost all the way out he'd stick his fingers into my butthole. I grabbed his cock with my greasy hand, gripping it firmly and stroking slowly.
Our cries and groans were building. I pounded madly. We were two athletes crazed with lust, insanely seeking release.
This was not love making. It was raw sex, incredible man on man fucking. Only two strong, athletic bodies were capable of what we were doing. If I had tried to do a woman as I was doing Jim it would have killed her. Jim's sphincter muscle tightened on my cock with all the force he could muster. He began to babble hysterically and then scream. His body thrashed wildly. I couldn't have pulled my cock out of him had I wanted to. His grip was too tight When I had thought about anal sex I had envisioned the bottom as being in a passive role, giving top pleasure while getting nothing in return. The realization that Jim was experiencing as much pleasure as me was as exciting as the intense stimulation my cock was getting.
I thrust with all the force I could muster. The pressure at the base of my cock was overwhelming. I began to shake. I was about to go. I felt Jim's asshole pulse madly. He screamed at the top of his lungs. His face was clenched in an indescribable grimace.
Torrents of cum came flying out of this cock. That was it. I threw my head back and howled as wave after wave of intense sensation moved from my cock up my back and down my legs. I thought my brain was going to be blown out my dick. Then my vision went blank and my muscles collapsed. I fell down on top of Jim.
Slowly as I became able to focus again I became aware of Jim sobbing quietly. "Are you all right?" I softly gasped, still out of breath. "I never believed my body could produce such sensation." he whispered weakly. I slowly rose up and looked around.
The lamp had been knocked on the floor and we had not noticed. The mattress was half off the bed and the sheets where lumped up and soaking wet with our sweat. Most amazingly, Jim's cum was everywhere. Streaks slowly dripped down the wall. More cum covered the sheets. Our hair, faces and chests were streaked with his jism. I must have gushed out has much as him.
Slowly I eased my softening dick out of his intestine. Jim couldn't move. I helped him stand and walk to the shower. I put him under the water and got in with him, helping him stand until he had regained his strength. Then, we soaped and washed each other's bodies, kissing deeply. It was clear he had no regrets. We toweled each other dry and got into the clean bed, falling asleep in each other's arms, dreaming of what was ahead for us.