4 comments/ 33176 views/ 14 favorites My First Time: Fucked on the 50-yard Line By: sapphire905 It's football playoff season again and when I watch the odd game or highlight reel I can't help, but drift back to my first time and losing my M2M cherry on the centre of a football field. I was 21 and my only experiences had been fooling around with the boy next-door: games of "you-show-me-I-show-you" which turned to "you-suck-me-I'll-lie-that-I'm-allergic-to-dick". I had a couple of girlfriends and enjoyed the straight role, but I always felt I was missing something. When the internet became more mainstream I was able to explore different websites and my curiosity for guy-on-guy stuff started to get the better of me. I posted a few ads, got some responses, and would stroke myself silly at nights thinking of a guy playing with me. I e-mailed back and forth with an older guy in a nearby city, we sent each other fantasies, and I would print them off to read that night. In a few weeks I had a little stack of favourites I would use to fulfill my imagination. It was late June when I re-connected with Rod. He had been the awkward new kid when he moved to town in Grade 6, but we became fast friends. All through junior and senior high he would tease me that "the beef wants out." People would talk about him and I think the jury had decided he was gay -- I was never sure, but he seemed to take a special interest in me during gym class when we had to wear the regulation uniform with the too-tight-too-short shorts. After high school we had a few classes in university together, but then went our separate ways -- him into business, me into environmental. He was never far from my mind though, especially as I was discovering the bi-gay side of the internet. I guess I fantasized that the rumors were true and when I heard he was back in town after exams, I gradually worked up the courage to phone him and see if he wanted to meet for a movie and catch up. He agreed and I knew I had to make a move. God I hoped those rumors had some truth. When that fateful early summer Friday arrived, my body was almost quivering with what I hoped would happen. I showered and admired my slim, swimmer-build body that was still smooth and hairless except for my legs and pubes. I dressed in jeans and a t-shirt to get out of the house and after driving to a mall parking lot I changed into what I hoped would seduce Rod -- tight nylon shorts and a t-shirt I had almost outgrown - too worn to be even called threadbare. Nothing was left to anyone's imagination. I drove on to Rod's house, rang the bell, and was greeted by his younger sister who gave me a quick, eyebrow-raised, once-over and pointed to the basement. When I got downstairs there was Rod -- toned from working out, and still with the same tan-coloured skin and long black hair. We greeted and the conversation started up pretty much where we left off three years before -- sports, life, finally girls and sex. As always he never gave up any information on the girls and sex, but was always good and pumping me for information. After a few minutes we took off for the movie then hit a burger joint. Neither one of us felt like going home, so we drove around the city, eventually finding our way to the football field of a high school where I know people would park and meet for their awkward intimate encounters. Parked beside the field, the conversation turned again to sex, what I had done, what it was like, what else I wanted to do. On that cue I reached behind the seat and pulled out the printed fantasies I had e-mailed and gave them to Rod to read. He read them in the dim light, his eyebrows raised. Was that interest? Disgust? I licked the lips of my rapidly drying mouth. "These are... interesting," he said. "Ever go through with it?" At least his reaction wasn't disgust. "N-no," I stammered, "Never really got around to it." We talked about 20 minutes more with him probing me for other fantasies. Finally the large drink from the burger joint was taking its effect. "I gotta drain the snake, man." I said, trying to act nonchalant. "Yeah, me too," he answered. We got out of the car and made our awkward way to the side of the sports field. I faced the bushes and pulled out of my tight shorts, letting a torrent go. I saw Rod pull up beside me, hiding himself, but clearly checking out what I had. "Nice," he muttered. I swallowed hard, my throat tight and dry and turned slightly toward him, giving a better view. When I was done I kept holding my limp cock, giving a slow stroke. I felt myself start to harden. I swallowed again, my raw throat feeling like I was trying to swallow razor blades. I looked up and saw Rob smile. He moved his hand along his shaft and gave me a view. He was holding a half-erect, uncut cock that was already larger than mine. We turned to fully face each other. I stepped closer and reached my hand out to his cock. He moaned as my fingers tightened around his shaft and slowly stroked him. He was getting harder and larger. I looked up to see his eyes closed, he face smiling in pleasure. I knelt down on the dirt running track, eye-level with my first real cock. I leaned forward, opened my lips and kissed the tip of his manhood. I used my hand to peel back his foreskin and slipped the head in my mouth, gently licking it with my tongue. Slowly I slid more into my mouth, taking his rapidly hardening cock into my mouth. I slid deeper until I felt it hit my throat, making me gag. I slid off only to swallow more. His cock reached its full hardness. From what I know now he must have been at least 8.5" and a good 6" around. I continued my oral attention on him, giving my first, awkward, sloppy blowjob. I could hear his moans as my mouth pleasured him, one hand holding his shaft at the right angle while my other hand stroked my hard 7", dripping pre-cum onto the track. I stood up and faced him, sliding my cock beside his and wrapping my hand around both, giving us both a slow handjob. We looked into each other in the eyes and I leaned forward. Our lips touched -- my first kiss with a guy. His hands grabbed the sides of my head as his tongue pushed against, then past my lips. I moaned as his tongue explored my mouth. His hands slid to my hips as our lips broke apart. "I want you to fuck me." I whispered. He moved my hand away from his cock and took mine. We bent down in sync to pull our shorts up to mid-thigh, enough to walk with as he led me across the football field. We stopped at mid-field, dead-centre of the school's sports crest - the Jaguars. We faced each other and kissed again. He slowly knelt down, pulled my shorts to my ankles, I kicked off my sneakers, I stepped out of the shorts. My bare feet feeling the cool summer grass. I pulled off the threadbare t-shirt as he leaned forward, taking my cock in his mouth. Slowly and gently he swallowed me. I leaned forward and moaned. No one had ever swallowed my cock like this. My head was swimming as his lips rode my shaft. His tongue massaged me. I could feel the load building as my hands gripped his head. "S-stop.", I whimpered. I looked up and obviously could tell how close I was. He stood and I knelt, taking him into my mouth again. He grabbed my head and pushed his cock into my mouth, making me gag. He held himself deep, I could feel my eyes start to water as I fought to pull off. He ground the tip of his cock into my throat. I couldn't breathe and my tears were streaming down my face. Suddenly he pulled off and I gasped for air, a string of slime connecting my mouth to his cock. He smiled and leaned toward me, pushing my shoulders down until I was on all fours. He moved around behind me and I could sense him kneel between my legs. I felt his hands touch my hips and slide slowly across my asscheeks, spreading them to expose my virgin ass. I could feel his hot breath on me, a sudden contrast to the cooling night air. Suddenly I felt a tongue on me, licking my hole. His hands massaged my asscheeks, fulfilling the evil deed of spreading me wider. My head was swimming, my heart was pounding, my body was on fire. He licked away at my precious cherry until I felt a finger press against my hole. Slowly it slid into me. I groaned in pleasure. He started fucking me with that finger and my hips began to buck in rhythm. Soon I felt a second finger stretch me. I gasped as he probed into me deeper. I felt a third digit attempt entry, but I was too tight. He stopped the finger fucking and replaced his tongue. I felt that wet muscle point and work its way into me. My shoulders slumped lower, raising my hips. He licked away for a few more minutes then withdrew. I felt the cool night air on my boy-pussy. "Ready?" he asked. I moaned my approval. I heard him spit and the sounds of him slowly jacking his shaft. A second spit and I felt warm, natural lube at my hole. His knees shuffled him closer to me. I could feel his cockhead pressing gently on my virgin pussy. "Relax" he said calmly. I took a deep breath and closed my eyes. His cock pressed harder against me. My hole was tight and doing its best to prevent the invasion. He pushed harder and I could feel my virginity straining. I exhaled slowly as he pressed harder. I stood no chance. I wanted it. I begged my ass to let that hard cock in. Slowly I could feel my ass stretch, slowly giving up the fight. Finally in a shock of pain and stabbing lights flashing against my tightly closed eyes I felt him enter, robbing my anal cherry from me. I gasped and whimpered. He held my hips and gave me a minute to accept him, then slowly pushing onward, invading me. My breath was shallow and rapid, panting against the pain of being de-flowered. Slowly he pressed on, determined to finish the job. Eventually I felt his hips press against my asscheeks. He was a deep as he could be, buried up to the hilt in my pussy. He stroked my hips and gave me time to accept him. Slowly my breathing returned to normal. The pain was slowly fading to a warm, good feeling. He began to pull out, slowly at first, leaving nothing but the head of his cock in my ass. Then he pushed forward again. I moved back and forth in rhythm to his thrusts. I got used to the motion as he gradually picked up the tempo. He reached under me and started playing with my cock. I got hard quickly and soon he was stroking me in unison with his thrusts. Faster he drove me, stroking my hard cock. I could feel my load building. I closed my eyes tighter. I was getting very close very fast. Finally I gasped I had reached my peak. He continued stroking and fucking as my body climaxed, stars flashing across my eyes as I shook with my orgasm, my cock erupting pulse after pulse of hot cum. I gasped as he picked up steam, my ass clenching his growing cock. I opening my eyes and looked down, the jaguar logo plastered with a perfect facial of my cum. I felt Rob grip my hips tightly and drive deep into me, pushing my body into the grass, the jaguar, and my own cum. He grunted and moaned as I felt his cock swell and explode into me, throbbing as his cum filled my ass with its first load of cum. He collapsed on top of me, our sweaty bodies laying together, his cock slowly wilting in me. I was no longer a virgin and it was the first of three times I ever trusted someone enough to let them in.