I was only 14 and he was 36, hot as can be and married to a super hot woman.
After doing yard work for Don and his wife for 3 years, I was 14 and with the wife out of town for a couple of weeks, Don invited me in the house after my work,. Suggesting I should shower to get all the sweat off me, I came out of the shower and my clothes weren’t there. Don was only wearing his normal shorts and tee, right now the tee wasn’t on either. He told me he was washing my clothes for me just to come out anyway. We were both guys, no need to be shy. With that he said that he would be too, and pulled down his shorts, he wasn’t wearing any underpants. He had some sandwiches and said he may have “accidentally” poured a glass of beer for me too. Holding the towel in front of me he pulled it away. I was acutely aware that I was staring at his cock and didn’t try to stop, not sure I could have stopped. I really hadn’t thought about being interested in other guys, but hoping for girls but his cock. . . it was actually pretty. It was about 6 inches long when soft, and was an inch and a half thick but it was perfect in color, the head was so pretty. He looked at my 3 inch soft and thin one and said “Nice, I like” I mumbled a thanks, and he said “Looks like you’re kinda liking mine too”.
I was, I didn’t know why. His pubes were trimmed and shaped they went from the sides of his cock trimmed into about 4 inches wide at the top of his hair. His balls were totally trimmed. I didn’t realize that at the time, I didn’t get hair on my sack at that time. “We can look all we want later, lets eat while everything is still ready” he said. We took plates into the living room, and there was porn playing on the television. Watching a woman get anally gangbanged was hot, she was a lot like his wife in looks and body type. “Does Cindy (his wife) let you do that to her?” I asked him. “Oh yeah, she lets me put my cock anywhere in her”. I commented “But she has a pussy, why do you put it in her butt?” He explained that after a while a couple needs to add variety into their sex life, but buttfucking was one of his favorites, the feel of a butt clenching rubber-like around your cock is totally unlike fucking pussy.
The video had added another character, a man dressed like a woman. He too got buttfucked by several of the cocks, and banged the hot woman in her butt. I was hard and he noticed. “No problem getting hard watching that, fucking any butt or getting your butt fucked is hot no matter what you’re doing” he said. “I like your hard cock, it’s looks really great, and by the way, your legs and ass are cuter than Cindys’” Out plates on the coffee table, he reached over and touched my cock. “Feels really good, do you like this?” he asked as he was moving his hand up and down on my cock. “YES” I answered. “Do you do this yourself, don’t worry I am married and I still do it”. I told him that yes I did it but this felt better. He said that having someone else do anything on your cock is better than yourself. “Watch what I mean” he said. With that he leaned over me, laid me back a bit and started sucking my cock. I’d seen porn of it, but this was the first time anyone gave me any feelings like this at all. It was incredible and after only a couple of minutes he used some saliva and pushed his finger into my butthole. I was even harder if possible with that and in about 5 minutes I was telling him it was about to shoot he’d better stop. He mumbled a negative and kept sucking and I shot off in his mouth. He pulled off, and made a point of swallowing it in front of me. “Like?” he asked. “Oh yeah, that was great” was my answer. He kept lighting rubbing my balls, and my thighs, then asked me to roll over. I asked why and he said it would get me hard again. Soon with some lotion on his finger and on my butt there was a finger fucking in and out of me, he was purposely rubbing on my prostate and it was working. Then it was 2, then 3 fingers. I was hard again.
Before he got me off again, he wanted to get off himself. I started to pick up like I was going to suck on his cock, but he kept me down. He got more lotion, and was laying totally on top of me. I automatically spread my legs for him, I didn’t know why I did that. Soon his cock was inside me, his trimmed hair up against my body he was making small little pushes deeper in and out. Then those pushes lengthened, bigger and bigger and soon I was being fucked. I knew he was fucking me, and I liked it. The initial pain was all worth it now. He was talking to me in whispers, telling me how good I felt all the while, then telling me I was so hot he couldn’t has too long and I told him to go ahead, do what he needs to do. That was my first time getting sucked, my first time getting fucked, my first time having a man unload his full load of cum into my backside. He gently pulled out and sitting back up, he put a towel under me to sit on and got me another glass of beer. “How do you feel?” he asked me and I told him I felt wonderful. “So you liked it, what I did to you?” he asked “OH yeah, I liked it, I liked what you did that first time with me too” I answered. With that he was sucking my cock again, and after about 15 minutes he was swallowing another load,.
I had to get going, get back to my parents house. He asked if I wanted to come back the next day and I did. I went back for three days, I got sucked, I sucked him off too, and mostly I got fucked. I got loads of cum up my tight boy butt. Then on the fourth day, He had porn of his hot wife Cindy getting fucked over and over by 6 guys plus him. She was wearing a very sexy lingerie set, all white, matching, even the garters and stockings her panties were already off. Then all the guys in the video left but the camera was still on. Cindy was fucked many times, all with cum in her pussy, or on her pussy, on her tits even on her face. Then Don started kissing her, licking the cum from her face and from her tits. He got a jar of lube and put it on her butthole, then she laid down on her stomach and he fucked her in her butt. I was hard as a rock again and so was he. “You like what she is wearing? Sexy isn’t it?” he asked, it was sexy as hell. “Come here” he said and walked to their bedroom. On the bed was the same outfit. “You’d look so damn hot in this, and I’d love to suck you and fuck you too while wearing the same outfit OK?” I didn’t know what to say but he was taking the stockings and draping them over my cock and my balls and gently rubbing them, they felt so good. I agreed, a little reluctantly but agreed. He helped me put things on, and then got her high heels. I had modestly longish hair and it was dark blonde like hers, he took me to the mirror and I did look like Cindy. He pulled me to him kissing me just like he did her in that video. I started to pull away but his tongue in my mouth dancing around made me stay. We recreated that video, where this time I was his wife in lingerie and he buttfucked me, not her, and did it in their own bed.
It was summer, so we talked to my parents explaining that while Cindy was gone for a couple of weeks Don wanted to do some work on the house for when she gets back and I was a good helper. They agreed that I could stay with him during that time. Soon I was dressing in the daytime in her regular woman clothes, and in the evenings and nights I was in sexy undies or lingerie for “my husband” as he called himself. I slept with him in their bed, I let him fuck me in their bed, I sucked his cock in their bed and he sucked mine there too. I was his wife for about 12 days before she came home. Don and I continued to meet up, sometimes a quickie in their basement when Cindy was home, sometimes out in their garage, but when she’d travel he’d have me over and I was again his “wife”.
Don and I carried on for 4 years. I’m 18 now and I still have sex with Don, though he got divorced from Cindy. I have had 5 other teens fuck me or me suck them, and 3 other older men. I crossdress with anyone that will let me. Don keeps a whole closet of girl clothes for me. Right after Cindy left him, they weren’t divorced, not even sure there were going to get divorced, she used her key and came in the house. Don wasn’t there, and I thought it was him and walked out of the bedroom in total en femme mode, and yelled “You ready to give me that beautiful cock now baby?” and coming around the wall was Cindy. “Well, well don’t you make a cute little fuck bitch” she said. “How long has this been going on?” she asked “3 years” I answered. She turned around and walked out.
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