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My first experience with a man
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This is the story of my first bisexual experience. I am from a rural and mostly religious community. I was probably 20, in college. I had a casual interest in pornography, eventually developing an infatuation with interracial porn that focused on hung men, and finally began seeking out videos with just men. I specifically enjoyed cumshots. I bought a small anal trainer dildo and started playing with it in the shower, sucking it while I stroked, and using it in my ass occasionally. I really enjoyed how submissive and sexy it made me feel. I desperately wanted to try something with a man but I was too shy and too nervous to pursue anything. I mentioned it to one ex-girlfriend and it was not well received, so I kept it to myself.

I had a very good long time friend who was just back from the army. We went to high school together and had spent alot of time together hunting and working out and other things. He confided that he was frustrated in his long term relationship because his girlfriend wouldn’t try anal and always made him wear a condom. At first it didn’t go anywhere, but it came up a few more times, and I felt he was hinting at something. We beat around the bush for hours until we both knew what we were getting at. Finally, I went out on a limb and laid it out there. I texted him “I think we can help each other out.” From that, our lust grew. We started out shy, but soon began to send photos. I was trim and fit and was able to take some really good pics of my butt that made it look almost girly. He sent pictures of his cock, and it was hot. I was turned on just looking at them. He was thick, proportional, manicured, circumcised. I sent him videos of me using my toy, and he would send videos cumming to them. We started writing stories about our future encounter to each other. They were graphic, sexy, satisfying. We learned a lot about what we wanted this way.

At the time we lived about 1.5 hrs away from each other. We planned a weekend and I came home from college to visit. He came over to grill with my family and it all felt totally normal. He pretended to leave and snuck into my old room. We were both nervous and shy, totally sober. I finally asked him if he had a favorite picture from those I’d sent. He smiled slyly and said yes, and described it. I pulled out my phone and showed him the picture. “This one?” It was. I had butterflies and my mouth was dry. I asked him if he wanted to see it in real life? He said he did. Nervously I turned around and pulled down the back of my pants, exposing my ass for him. I felt exposed, vulnerable. I felt sexy. For a moment he didn’t say anything and just stared. He crossed the distance between us, and grabbed my cheeks. He felt me, squeezed me, explored it with hands. We didn’t say anything, it was dead quiet, just the sound of our breathing. The suspense was palpable. Eventually I pulled up my pants and asked if I could see him. He pulled down his shorts, exposing the cock I’d seen in so many pics and videos. My heart was racing! He said I could touch it if I wanted to. I wanted to. I grasped it, and was surprised at how it was warm and felt so soft. I stroked him lightly and asked if I could suck it. He said yes. I got on my knees in front of him and stared at it, pointing directly at me. I put the head in my mouth, immediately feeling the slick precum and tasting it’s saltiness. I did my best to suck him like I’d practiced and been sucked. I felt him get hard in my mouth. I didn’t want the experience to end so I sucked until he pulled me back up and he pulled down my shorts. He turned me and bent me over the bed. I was SO turned on that he was taking charge. He rimmed me and it felt incredible. I loved being the center of his attention. Finally he stopped and asked me if I wanted to continue. Of course I said yes. I kicked off my shorts and got on my back on the bed and spread my legs for him. He had told me previously he wanted to use Vaseline. I wanted something like astroglide, but I obliged. He mounted me and gently worked his way in. He was thicker than my toy, and it hurt a little, but he was patient. Finally he was completely inside me, and I’ll never forget how he said: “I can’t believe I’m all the way inside you!” It was surreal because we had been friends for years. He fucked me gently, softly, and slowly picked up speed. We had agreed no kissing, but his warm skin and weight on me was sexy. I tried riding him briefly. Then he asked if I wanted doggy. Of course I did! I turned around and he entered me, fucking me from behind while I was bent over the bed. I was rock hard. He reached around and stroked me, and I came harder than I’d ever came in my life. It felt incredible. I was breathless and he smiled when he saw the mess I’d made. I got on my back again for him, and he stroked over me. He got himself close (I think he was tired) and entered me again. Then he fucked me a little harder and faster than before and I begged him for his load. By this time my butt was sore but I felt him finish inside me. We were breathless. We cleaned up, and he left. We did this once more in his SUV, then we lost touch and never spoke again.

It was over 10 years ago but was the first experience I had. I still get off to it. I wish I could do it again. I had 3 more experiences after that, each fun in their own way but not even close to the first. Since then I’ve found my prostate and know myself better sexually. Even though I’m married to a beautiful and perfect woman, I still crave cock. She knows, but we don’t really talk about it.

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1 year ago