Winning the bet by like2watch1576

A literotic sexstories: Winning the bet by like2watch1576 ,

True Story, Bi-sexual, Boy / Boy, Oral Sex

I’ve always considered myself and portrayed myself as straight. But in the back of my mind is an experience from my past that calls me a liar.

When I was in my early teens I had more freedom than most of my friends. My parents were divorced and my mother worked the third shift. She’d be asleep when I got in from school and would be leaving for her 11PM to 7AM job by 10:30. So I’d be alone all night. And lots of times I’d go out and ride my bike to a nearby convenience store and hangout checking out all of the men’s magazines. I had kind of an unspoken deal with the guy who worked nights there. I’d help clean up and stock the cooler and he’d give me a magazine every couple of weeks and buy as many as I wanted despite being nowhere near old enough to.

One of my friends would spend the night a lot when school was out, his parents having no idea my mom worked nights. Something we liked doing was going out peeking in people’s windows. And we lucked up on several occasions seeing women changing clothes for bed and a few times see couples having sex. One night we went to the store and I told him I was going to buy the new playboy magazine and he just laughed and said there was no way they’d sell it to me. I said I bet they will, and he said if they do I’ll suck your dick. I laughed and said Ok. I took it as just an off the wall comments like when you say if so and so happens I’ll kiss your ass. You don’t really plan on kissing their ass. So I go in and as expected buy the magazine.

Jeff just shook his head and said I’ll be damned. We went back to the house and undress down to our underpants as we always did and got in bed and started looking through the magazine. By the time we were finished, I wished Jeff wasn’t there because I wanted so much to jerk-off. But I put the magazine under the bed and turned off the light. A couple of minutes later Jeff said he guessed he needed to pay off on the bet. By then I’d forgotten all about the comment he’d made at the store. I still thought he was joking and I said yep and you’re going to have to open wide. Still thinking it’s all a joke. Then I feel his hand sliding inside my underwear and wrapping around my hard cock. Then the weight on the bed shifted and he was on his knees beside me.

I’m lying there frozen in place not really sure what’s going on. I’d known Jeff for almost a year and never thought of him as bi or gay. Then I feel my underwear being pulled off and once I’m naked his hand’s wrapped around my cock stroking slowly. Then he spreads my legs and gets between them. By now my eyes have adjusted to the dark and I see him leaning forward. Then I feel his hot mouth wrap around my cock. I knew I should stop him but I just laid there. He’s slowly sucking it as it slides in and out of his mouth. And he’s fondling my balls and ass. As he gradually swallowed my cock deeper and deeper in his mouth. Occasionally taking it out of his mouth licking up and down the shaft and around the head.

Then saying mine was one of the biggest cocks he’d ever sucked. He kept sucking & stroking it until I shot my load in his mouth. After swallowing my cum he kept licking my cock and went down and sucked on my balls as sliding one of his fingers in my ass just a little. I got hard as a rock again and was shocked when he asked if I wanted to fuck him in the ass? I said no, but told him he could suck my dick again if he wanted. He went back to sucking and stroking my cock. And started telling me how his family moved a lot because his father was in the military and said some of the soldiers had taught him how to suck cock at one of the bases. And said I was the first guy his age he’d ever sucked off. He kept sucking until I shot a second load and he swallowed every drop.

After that night every time he spent the night he’d without a word start rubbing my cock then pull my underwear off and suck my cock. So I got to where I just started going to bed naked. Soon he was going to bed naked too, and after sucking me off he’d jerk-off while telling me how much he liked sucking my cock and about fantasizing about me fucking him in the ass. After a few months of this, he started asking if I’d suck him off and I always said no. But did finally agree to jerk him off every once in a while. And I must admit feeling another guy’s hard cock in my hand and seeing how turned on he got while I stroked his dick was kind of hot. It went on for about six months with him sucking my cock a few times a week and me jerking him off. Then I found out his dad was going to be transferred again. A few days before they were to move he spent the night for the last time.

We got naked and got in bed and he wasted no time in going down on me and getting me off. Then I started jerking him off. But surprised him and myself when I leaned over and took his cock in my mouth and started sucking him off until he shot off. I assumed it was a one-time thing. Then 30 yrs later I sucked off 5 guys at gloryholes over about a 2 month period. That was 15 years ago and haven’t had the desire to go down on a guy since. But oven my entire life I have let guys suck me off. Mostly at gloryholes. But a few when my wife and I were swingers she liked seeing guys suck me off and I’d let a guy occasionally suck my cock and act like it was a favor for her. She had no idea how much I enjoyed it. Once when I was in my 40’s she told an 18-yo boy who’d been watching her on the beach that he could fuck her. But to be sure he wouldn’t tell anyone he had to suck my cock first. He was straight but she was so hot he agreed. And it felt so good having that young guy sucking my dick. Then seeing him fuck my hot wife.