I would like to hear real instances of first time experiences especially between a young and a very mature person. How Doug all start.
I was watching TV with my mom and her boyfriend once when I was 14. He and I had a blanket over our laps. I felt his hand on mine as he slowly moved it to his crotch. I grabbed there instinctively and he was hard and getting harder. I started to stroke him, slowly, and then mot so slowly.My mom fell asleep pretty quickly, so he and I left to go to my bedroom. He practically tore my pants off and climbed on top of me on my bed. He held me down and fucked me missionary with no condom. He came quickly but didn’t pull out, just lay on top of me panting while he got hard again. He came in my ass three times total that night and called me a good little slut.
Even from the early days my male playmates have, mostly, been younger than me. The first few that were older than me were only by a couple of years. When I was twenty-five, I let a much older man, fifty-five, pick me up in an adult bookstore. He was rough with me, mouth fucked me, savagely, and plowed my ass with an impressive hard on for an old festus. The only action I got was a reach around. It was a sleazy one night stand, but, better than jerking off.
My neighbors had noticed that a handful of boys were sneaking in and out of my bedroom after a face-fuck with me in my sister's panties. I was a ripe twelve year old and he was in his twenties and has been there with other boys and knew what I was thinking before I thought it. Though a virgin twelve year old he asked me to, "No way! I'm never gonna do that with you or anyone!" I said defiantly shaking my head and moving away from the hand that firmly gripped my left buttcheek. I laid on my bed on my tummy on my underpants that night pretending that he was fucking me like he said so. He was watching me legs spread buttcheeks clenched as if I was being fucked through our bedroom windows and I knew it. I did this nightly for two weeks and then it happened. My two hands cupped my little hairless penis through my underpants as I lay on my tummy legs wide grinding in my imaginary man fucking my boy's ass fantasy, I came uncontrollably. It wasn't the dry-orgasms I was having, it was a real gusher of a first that flooded the whole front of my panties to the point of embarrassment. I walked to the window alongside the dimly lit desk lamp that showed me explicitly. I was naked except for my brief white cotton underpants that were totally transparent from the boycum that saturated them looking at his nakedness through our open summer night windows. He was beautiful, a man, thinly muscular and sporting a gorgeous hard- on that all of a sudden I wanted, I wanted it inside of me, my mouth, my tightly twitching boycheeks, just all the way in me! He waived me over and I nodded mouthing "Okay." My pouty lips mouthing "O-K-A-Y" got me as excited as him and I scampered to the bathroom to wash the sticky boy-cum off and in fresh underpants he helped me step from my roof's edge to his and held my butt through his window and out of my underpants as he kissed me into submitting. Or was it I kissed him till he fuck'd me?
I was 13, a fresh-faced boy with a natural feminine beauty that some boy's have. My mom's hairstylist admired it especially my over the top gorgeous ass. Mom was delighted that he was so interested in me and other than doing my hair his expertise doing my ass was very nice for me. Mom didn't figure that. I was quite the prize for showing off to his friends.
I was 16 and it was with my mom's coworker, he was 55. Something about him always turned me on. I knew he was gay and although I did have a girlfriend and was sexually active, I really wanted him. There was a huge party at an arena one night, live bands and all. I saw him there and went over to chat. He was really nice and did not hit on me at all. He said he was going to go outside to his car to get some cigarettes. I asked him if I could tag along and he said sure. It was pitch black in the far corner of the parking lot and could barely see anything. He told me he had to pee so he turned from me, puled it out and began to pee just like any guy would. I was shaking from excitement. Trying to sound grownup I asked him how it's hanging. He just chuckled and said straight down. I didn't expect that answer so I said "really". He said ya, look but it was so dark so I moved next to him. I told him I still couldn't see so he said I'll just have to feel it. I knew that was it and wanted him and wanted to give myself to him fully. We kissed and it was very hot and passionate. He was drooling into my mouth and I took it all. He gently pushed my head to his cock and I sucked him for all I was worth. He was getting close and told me to swallow and I did. I was hooked. We met often after that. He told me that I was a partier just like my mom but that's another story
Im a 30yo striaght male. 6'0", muscular with dark hair and dark eyes..My niece's friend is a trans girl. When I came to pick her up from her 16th birthday party the friend answered the door. We were talking while everyone else was downstairs and the whole time she was giving me googly eyes, looking at my crotch, flipping her hair, etc. I don't know what came over me but I told her I had a present for her and to close her eyes. She complied and I pulled her into me and kissed her. She didn't resist at all. We made out in the kitchen for a few minutes and I could feel her little dick getting hard. Against mine. I told her I was going to fuck her a dragged her into her room. We ripped each other's clothes off and fucked like crazy. She sucked me, I sucked her. I fucked her ass and jerked her until we both came. I've never done anything like that before, but it was so hot. She's driving now wants to meet up again. I really want her again. The feeling of my cock pounding her ass and her little dick throbbing in my hand as she shoots her load across the bed is the best I've ever felt. I like making her squirm when take her whole dick in my mouth and fondle her balls too.
I was 15 he was late 20's if that counts as mature. Me and my mates would go to his house and get stoned, then this last time all the guys had crashed and burned there was no where really left to sleep he could tell I was about to pass out and said there's a spare room at the back of the house, you can crash there if you want. I said thanks and at a ghere off down the hall past the bathroom into t honest door on the right saw the bed stripped to my jocks and fell onto the bed. I was sleeping in seconds. Some time during the night I a w one as my briefs were being pulled down then a cold hand was grabbing my Cock which hardened pretty damn quick, I had no idea who it was the room was dark, and the sheet seemed to be over their head. I didnt really care especially when those warm wet lips engulfed my Cock and immediately started bouncing up And down my hard cock. That mouth was like a sealed vacuum, I kinda felt like my body was lifting of the bed as it went up, it wasn't long before as my hands gripped the sheets by my sides tight I exploded and pumped what to this day I still believe to be the biggest load of my life into that wet sucking mouth. I felt so faint and drained by the time "Glen" whispered in my ear did you like that ?Do you want to suck me now, I timidly said no thanks. Ok he said back and I just went to sleep, in the morning he was gone to work and my mates had all left as well. I hitched home and the next weekend when we went back the house was empty. He'd moved. 100% true, nothing was changed, including his name.
I was 13 the first time I had a dick in my mouth. The guy was in his late 20s. I used to watch him sunbathing nude on his back deck. Every once in a while he would get up and piss off the deck. I guess I wasn't being to sneaky enough. He knew that I was watching him. One day he called me over and said why are you hiding in the bushes just come here and get a closer look. I was so nervous that I was shaking. I sat next to him and I couldn't take my eyes off his cock. He kinda laughed at me and said do you want to touch it.i did I was amazed how fast he got hard it felt heavy in my little hand.he stood up and said open your mouth. He pushed the head of it into my mouth it tasted so good. I didn't know what I was doing I licked it and tried to get more in my mouth but I gagged .he ended up jacking off in my mouth and I swallowed his cum . After that I was hooked. I couldn't wait to see him again. I was 14 when he finally fucked my ass. He broke me in slow. I loved every moment of time I was with him. I'm a lot older now and married. My wife knows that I love cock. Don't think I will ever stop. Thanks to him.
Had sex with my father in-law a few days before I married his daughter. But, we hooked up at a local gay bar with him before the first formal meeting of the family, being so far away in distance. We did not know each other before meeting in the bar. I was 24, 20 years later and we still fuck and suck each other soon as the wives leave to shop.
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