TyLeR's True Story, New Beginnings
By: TyLeR_College_Wrestler@msn.com
I wanted to personally thank each and every one of you guys who have e-mailed me with such overwhelmingly positive comments after reading some of my other stories, especially "TyLeR's True Stories, Parts 1, 2 and 3", under the BEST FRIENDS section of this site. Many of you have asked me what my very first sexual experience with another guy was, so I've decided to finally share that with all of you.
Of course as wrestlers on our high school's team, my straight teammates and I often popped big boners from the physical exertion of the event. At first, we would discretely jack-off afterwards in the locker room showers. Then somehow over time it became a group circle-jerk. It slowly progressed until we even started having contests, like who could shoot the farthest, the most, etc. We all had girlfriends, so there was never any concern about any of it ever being considered "gay" in any way. We were all very close friends and extremely comfortable with one another, so it was no big surprise that we soon progressed to actually jacking each other off in the showers. Because I had the largest cock on the wrestling team, the guys seemed to take great pleasure in discretely handling it. Of course Coach had no idea what we were doing. We were always very careful not to get caught. But I don't consider any of this as being my first experience with another guy at all, because there was nothing really sexual about it in our minds. We just needed to relieve the built-up tension in our rock-hard cocks and aching balls so we were simply helping each other out. My true first sexual experience with another guy happened much later, after graduation from high school.
Well, let me start off by saying that this story is also absolutely TRUE! This is really a PRELUDE to all of the other stories I have written so far.and should be called "TyLeR's True Story, New Beginnings"!
As you know, my name is TyLeR, and I'm now a 20-year-old, college wrestling jock from Canada, 6'4" tall, 195 lbs. of solid muscle, with long shoulder-length, light-blond hair and cobalt-blue eyes, a buff, hairy, jock body, and an 11" uncut cock. I was born in Canada, but raised in Bloomfield Hills, Michigan, and abroad. I currently attend university in Windsor, Ontario, Canada, mainly to be near my awesome grandparents.
Until this event happened, purely by accident, that summer, I had considered myself to be totally "straight". I had been with tons of girls from an early age, so I never even thought about sex with other guys. There was no need. I was getting plenty of action with most of the girls at my high school, especially from my girlfriend, Tiffany.
My girlfriend and I had just graduated from high school and planned to attend the same university in the fall. We had made plans to move in together and share an apartment off-campus. I was planning to study advertising/marketing/business, while she was very interested in photography. I was still 18 that summer, hardly waiting to turn 19, the legal drinking age in Ontario, on the 4th of July, and I had to work at my father's offices in Detroit, Michigan, starting in June.
My parents owned a large international advertising agency. My two older brothers, Chandler and Christian, were identical twins, both 26 years old at the time, and married to two very sexy women and had infant children. They already worked for my dad. Chandler lived in Toronto, Canada, with his family, and ran the Canadian offices, while Christian lived in London, England, with his family, and ran the European offices of my dad's company. My dad ran the corporate head office in the United States. The plan was that once he retired, I would take over the U.S. offices, and they would become three equal branches: offices in the U.S., Canada, and Europe. In the meantime, the plan was for me to go to university in the fall and start working on getting my college degree.
I grew up in the family business so I knew it inside and out. Even though I was not there on a full-time basis yet, like my brothers were, I already had certain clients requesting me for presentations; usually, they were women. During my first few weeks at the office last summer, I noticed that there was this one particular Federal Express deliveryman who made daily deliveries to our offices. Each day he would show up with overnight letters and packages, and he would always stare at me, especially at the large bulge my big cock and balls made at the crotch of my tailored suit pants. It was kind of obvious. I just figured he was a "fag" and ignored it.
Well, one night I was working late on a client's creative campaign. Everyone had gone home for the evening. Tiffany and I had had an argument over something totally stupid earlier in the week, and she was punishing me by withholding sex from me, as women often do. So I was extremely grumpy and sexually frustrated all that week. I suddenly heard a man's voice shout from the lobby. I walked down the hall and went into the reception area to find the same FedEx dude with a package. As I was signing the forms, I noticed him staring at my crotch again. I don't know if it was because I was angry with Tiffany, or was just plain horny as hell, but I looked directly into his eyes and bluntly asked him why he always stared at my crotch whenever he made deliveries to our offices.
The FedEx dude was in his early twenties, an inch or two shorter than me, but he was very muscular. He obviously worked out at the gym in his spare time. He had dark hair, blue eyes, and a nice tan, I noticed, as he stood there in his uniformed shirt and shorts, his face blushing a deep crimson with embarrassment. He quickly denied it. I don't know what got into me at that moment. I became very aggressive and simply unzipped my suit pants and hauled out my big, fat, uncut cock! It was limp but felt very thick and rubbery in my hand.
"Is this what you've been dying to see?" I remarked with what I just know had to be a smirk. Looking back, I don't think I really had any intention of having him blow me. I was just being sarcastic and rude.
Needless to say, he dove for it! He quickly knelt down in front of me and swallowed my cock into his talented mouth. I must admit that I was surprised by his lewd actions. He caught me completely off-guard. I forcefully pulled his mouth off of my cock and stared directly into his eyes. I could see the lust in them! He was hungry for my big cock. He wanted it real bad!
My first impulse was to punch his fucking lights out! But I suddenly noticed that my cock was starting to get hard. His mouth did feel good on my big cock! Deciding that I needed to shoot a big load, a week's worth thanks to Tiffany's punishment, I grabbed my cock and swung it in front of him, teasing him with it. I slapped it hard against his face. He kept opening his mouth and trying to swallow it again. He would dive for it, and I would pull it away from his cock-hungry mouth at the last second. I peeled back my foreskin and touched the fat head against his wet lips. His tongue shot out and licked at it. It felt so damn good! This time when he lunged for it, I let him have it. He swallowed it into his mouth and his talented tongue and deep sucks quickly made my big cock rock-hard!
He gripped my cock at the thick base and gently stroked it as he sucked on the flaring tip. He played with my foreskin, pulling it back and forth over my bloated cockhead. He slipped his tongue in between my foreskin and cockhead and gently chewed on it. No girl had ever done that to me before. I started oozing pre-cum, and he eagerly lapped it up. As he sucked my cock, he reached up and undid my leather belt and the top of my suit pants, opening the flaps of my fly. He dug his hand inside and pulled out my big, low-hanging, hairy balls. With one hand, he cupped my heavy balls and gently squeezed them, as he stroked my cock with the other and continued to give me one of the best blowjobs of my life!
I quickly pulled my double-breasted suit jacket off and tossed it on the reception desk in the lobby. He pushed my suit pants and boxer-briefs down my muscular thighs, as I undid my necktie and the buttons on my dress shirt. I tossed my necktie and shirt on top of my jacket and stepped out of my underwear and pants. I kicked off my leather dress shoes and stood naked in the lobby with just my dress socks on. He cupped his hands on my hard-muscled ass and pulled me deep down into his throat. Soon his nose was buried in my pubes and his chin was banging against my hanging balls. My huge cock throbbed and twitched deep within his clasping throat. His fingers on my ass slipped inside my hairy ass crack and rubbed my puckering hole without entering it.
"Ohhhhhhh.fuckkkkkkk!!" I loudly moaned. I couldn't believe how good he was at sucking my big cock! I grabbed his head in my hands and started guiding it along my giant prick. I was leaking so much pre-cum, and he was feasting on every drop.
He withdrew his mouth from my cock and tongued his way down the sides of my fat shaft. He pumped his fist on it as he began to mouth my aching balls. He took one of my big balls into his mouth and ran his tongue all over it, wetting it down with his saliva, then withdrew it and swallowed the other one. He gently tugged on my chunky balls with his teeth.
Suddenly he stopped and turned me around, with his face buried in my ass. "Hey!" I protested, until I felt his tongue make contact with my tiny hole, and my whole body seemed to tremble. "Ohhhhhhh, my God!" I couldn't believe how good his tongue felt on my twitching ass hole. He kissed it softly at first then licked it. He wrapped his lips around my puckering ass lips and sucked so hard on my quivering hole that it felt like my insides were being pulled out from it! He was sucking the hair right out of my butt hole. His tongue slowly pried deep into me, feverishly fucking my "cherry" ass hole. My quivering hole was dripping wet with his saliva. He gently blew cool air on my wet butt hole, which made it pucker open and closed like crazy. Goosebumps popped up all over my muscular body. My girlfriend wouldn't go anywhere near my ass. She always thought the act of rimming was "too dirty", yet this guy was devouring my ass with the same kind of hunger that I had for eating a girl's pussy. My legs were quivering from the pleasure his mouth and tongue brought me.
His fist continued to stroke my giant, pre-cum-oozing cock, as he hungrily ate my jock ass. I slightly bent over and spread my ass cheeks far apart, so he could get his tongue even deeper inside my virgin hole. He was tongue-fucking my tiny hole, and I was moaning and groaning loudly from the highly pleasurable sensation. He pulled my throbbing cock down between my thighs and eagerly sucked on it from behind me. He'd deep-throat my cock, suck on my low-hanging balls, and eat my trembling ass in a passionate rotation.
Suddenly he stood up from his knees and unzipped his uniform shorts. "I need that big fucker up my ass!" he breathlessly said, as he undid his shorts and dropped them to the floor, along with his white cotton briefs. His average-size, circumcised cock was fully erect and dripping pre-cum from its swollen head. He leaned over the desk in the lobby and presented his muscular ass to me. "Fuck me with that monster," he moaned.
Without even thinking about what I was just about to do, I quickly grabbed my suit pants from the floor and pulled my wallet from the pocket. From my wallet, I slipped out a condom. I always keep a condom or two in my wallet, ready to fuck a juicy pussy at a moment's notice. I tore the wrapping with my teeth and pulled the condom from it. As I slipped the condom on my twitching cock, he asked me to stand in front of him so he could wet it down with his spit before I fucked him. He didn't want me to fuck him dry. I did as he asked, and he quickly started sucking my condom-covered prick. All the while, I slapped his muscular buttocks hard with my hands. I slipped a finger in my mouth to wet it down, then slipped it into his tiny ass hole. God, he was tight! Tighter than any pussy I had ever fucked!
I pulled my cock from his mouth and walked around behind him. I didn't waste any time at all. I just rammed my big, fat cock up his ass in one powerful thrust. A loud scream escaped from his throat, as I abruptly entered him. I was so horny that I just started fucking him, without even giving him a chance to get used to having my 11 inches deep inside his super-tight ass. I pounded his ass hard, long-dicking him. The rougher I fucked him, the louder he groaned and the more he seemed to love it!
He jacked himself off, as I jackhammered his ass with my blood-engorged cock. I couldn't believe how good his ass felt wrapped around my hard cock. I must admit I loved fucking that hot ass! It felt very different than fucking a girl's pussy, much better. I was hooked! I grabbed him by his waist and pulled his ass down hard on my big cock, sinking deep in him. My abs kept smacking against the top of his buttocks, and my heavy, hairy balls kept slapping against the back of his thighs, as I repeatedly pounded his prostrate. His ass muscles tightly squeezed my cock, as he shot his big load all over the top of the desk, which in turn caused me to shoot my week's worth of cum into the condom covering my big dick up his ass.
Just as my orgasm was winding down, we were abruptly interrupted by my cousin Ryan walking in on us! Supposedly, Ryan had forgotten his cell phone at the office and returned to get it. I froze in fear, the FedEx dude grabbed his discarded clothes and ran, and Ryan just stood there and laughed his ass off! Ryan is a year older than me and also worked that summer while out of school. I quickly pulled the condom off of my spent dick and started getting dressed, my face burning red with my embarrassment. It was that day that Ryan told me that he too was bisexual. Since then, he and I became very close friends. We've never had sex together, but we've played together in group sex after that (one such group sexual encounter with Ryan was in "TyLeR's True Story, Part 3").
Since my first encounter with another guy, I have gone through an evolution of sorts from being "totally straight" to being "bisexual". After that summer, I often thought about having sex again with another guy but didn't act upon my impulses until my winter break trip to my parents' vacation condo in Florida with my cousin Ryan and my straight wrestling buddies.
While in Florida, I was approached by many guys. Our girlfriends took their own trip, so us guys were all alone and free to roam. We got drunk and high almost every night. One night we even played "Truth or Dare". On a dare, my straight buddy Josh (who later experienced his own first time with another guy in "TyLeR's True Story, Part 1") was told to kiss me. I was stunned when he did, giving me tongue and all. My drunken buddies laughed their asses off, thinking it was funny, while Josh and I French-kissed. Later that night, Josh drunkenly cornered me in the kitchen and wanted to kiss me again. I should have known right then and there that Josh was open to sex with another guy, but I was so concerned with hiding my newfound bisexuality that I laughed at him, told him he was too drunk to even know what he was doing, and pushed him away. Josh was a fucking hottie, so I was strongly attracted to him, but I didn't want my straight buddies to know about my secret desires.
Later in the week, we went jet skiing. At the Jet Ski rental place, the manager, a hot blond dude in his early twenties, kept staring at me and at the big bulge my cock and balls made in my Speedos. I could sense his obvious interest. He asked me to join him at a midnight beach party that night, and I quickly accepted.
At the beach party, he walked me away from the crowd to under a nearby pier. Under the pier, he groped my crotch and kissed me. He knelt down and started mouthing my cock through my Speedos. Using his teeth, he pulled my Speedos down my thighs. He hungrily sucked me off and ate my ass. I was surprised when he swallowed all of my cum when I shot my big load down his throat. We quickly returned to the party.
A few days later, while I was in the men's changing room on the beach, I noticed a married man in his early thirties, with two small boys, bluntly staring at me and at the big crotch bulge in my Speedos. I thought it was simply his envy. I had no idea he was actually interested in me. He took his two kids out to his wife on the beach and returned to the men's changing room alone. I was stripped naked and showering the sand off my body when he returned. He commented on the size of my "big cock". It was then that I knew what he wanted. He walked over to me and grabbed my cock and started stroking it. Since I didn't protest, he quickly dropped to his knees and proceeded to suck me off and eat my ass. What excited me most was the fact that any guy could walk in on us and catch us in the act. The danger was thrilling. After he swallowed my big load, he stood up and left. That night as I lied in bed trying to sleep, I couldn't help but think about what had happened to me on the trip so far, and my cock was rock-hard.
A few nights later, my buddies and I went bar hopping and ended up at a dance club. Thank God for fake IDs! At the club, one of the bartenders, a sexy dude in his late twenties, kept sending me free drinks all night long. I walked over to thank him and talk to him for a while. He and I quickly hit it off. He had the next day off and asked me if I wanted to go with him to Disney World for the day. I readily accepted. My straight buddies were too busy dancing with some of the hot girls in the club, trying to get in their panties, to notice my conversation with Michael, the bartender.
The next day, Michael picked me up and drove us to Disney World. We had a ball! We rode all the amusement rides, especially the roller coasters. We went back to his apartment that night. He fixed us some drinks. As we sat on his sofa, he groped my crotch and kissed me. He proceeded to undress me. He hungrily sucked my cock and ate my ass. He twisted his body into a 69-position on the sofa, and I quickly pulled his shorts down to mid-thigh and sucked my very first cock.
He had a fat, circumcised cock about 8 inches in length. The salty taste filled my mouth. The way his hard cock felt in my mouth drove me wild. I wanted more. I tried to swallow all of it down my throat but gagged. I sucked his big cock and balls and rimmed his sweaty ass, as he did the same to me. I couldn't believe I was doing it all! Nothing could stop me now! I wanted to experience as much as I could! I wasn't disgusted at all by eating his ass. It was as if I was eating his man-pussy. The musky smell and taste excited me. When I sensed that he was about to shoot his big load, I pulled my mouth off of his cock and let him shoot his cum all over my chest. I was surprised he swallowed my big load when I came. I was still rock-hard, and he wanted me to fuck him. He didn't have to ask me twice. I pulled a condom from my wallet and quickly slipped it on, as we both stripped completely naked. I had him on his back on the sofa, with his legs up in the air and resting on my shoulders, as I fucked him hard. He had an awesome ass!
After I came and pulled out of him, he wanted to fuck my ass but I wasn't ready for that yet and wouldn't let him. Instead, I fucked him again! I stayed at his apartment for 3 nights. We sucked each other off, ate ass, and I repeatedly fucked him the whole time there! When I returned to my parents' vacation condo, my straight buddies had automatically assumed I found a hot girl and spent the last 3 nights with her. They all patted me on the back as if I was their hero. If they only knew I was really with another guy!
That Christmas, my parents surprised me by flying down to Florida on my Dad's company plane with gifts for me and all my buddies. It was a nice surprise. My uncle, who works in the film industry and lives in Bel Air, California, was throwing a major Hollywood-style New Year's Eve party and invited all of us to attend. My parents offered to fly all of us out there from Florida, and we readily accepted. My buddies were thrilled. It was at my uncle's wild party that I had my first 3-way.
There were over three hundred guests invited, and I met this really hot married couple there. I snuck the guy and girl up to my guestroom. They were both in their late twenties. She was very conservative, but he was a really wild fuck. While I ate her pussy, he sucked me off and ate my ass. I then fucked them both, first her, then him. She was quiet, but he was a real screamer. I had to use my pillow to stifle his loud screams, as I fucked his hot ass. I could tell that she was a bit jealous, as she watched me fuck him. I went through so many condoms that night, as I repeatedly fucked them both. As they were leaving, he slipped me a piece of paper with his name and phone number written on it, asking me to meet him alone the next day so we could fuck again. Not wanting to hurt his wife in any way, I didn't meet him the next day.
After all of my wild times during our winter break from school, things calmed down somewhat when we returned home to our girlfriends and got back to the grind of school. As I did after my very first time with a guy, I felt very guilty about what I had done. Yet, I was absolutely thrilled I had experienced the things I had.
About a month later, I was at Hockeytown Cafe, a sports bar in Detroit, one Saturday night when this really sexy guy walked up to me at the bar and started talking to me about Red Wings hockey. His name was Todd (that night we became regular fuck buddies, and I talk about him more in "TyLeR's True Story, Part 2", where he seduces my straight buddy Josh in a 3-way that suddenly turns into a crazy 4-way). He invited me to his home for some more drinks.
I knew something very hot was about to happen between us. I was strongly attracted to him. He was a very handsome gym jock, who was 37 but looked more like he was 27 years old. I followed him to his house. We ended up in his bedroom, where we 69ed and I fucked him raw. Todd was an awesome "bottom". It was then that I realized I was referred to what most gay men would call a "top".
After that night, Todd and I became regular fuck buddies. Todd was a very thoughtful dude. Before we even had sex that first night, he showed me the results to his recent medical tests to prove to me that he was "clean". How many guys do you know who would do that? I was very impressed. I told him that the university often tested us jocks and that I was "clean" as well and planned to stay that way. I felt very comfortable with him from the start. I had my first unprotected gay sex with him. I "barebacked" his hot ass over and over again that night. It was awesome!
We met regularly after that, promising to only have gay sex with one another. We made a deal. If we were to ever desire sex with a new guy, we would tell the other about it first. It was a deal that worked well for us until I went on my spring break trip to snowboard in Colorado with my cousin Ryan, my straight best buddy Josh, and all of my other straight wrestling buddies a couple of months later. Please read "TyLeR's True Stories, Parts 1, 2 and 3" to see what has happened since.
If you liked my true stories, I'd like to hear about it. E-mail me at TyLeR_College_Wrestler@msn.com