- Gay Stories -
I've never been attracted to men, but from an early age (about 12) I have had something of a fetish for being anally penetrated. Shortly after I started masturbating, I started experimenting with fingering myself and found that I came so much harder when I did it. From there, it escalated into pretty much anything smooth and phallic that I could safely insert and not get stuck.
By the time I moved out of my parents house, I was pretty adept at pleasing myself anally. I had even learned how to milk my own prostate. I moved to England when I was 18 (the legal drinking age) and found a fancy for the drink. The anal play evolved rapidly with alcohol acting as a catalyst. I started ordering anal toys online. At one point, I had several plugs and a few dildos. They kept getting larger every time I got a new one. My largest plug was 9.75 inches long and 3 inches in diameter at its widest point and the largest dildo was a monstrous 14 inches long and 4 inches in diameter. I had myself trained to take both of these entirely into my rectum.
I moved back to the states three years later for my job and got rid of my collection because I was paranoid of someone finding them while they were in transit.
Shortly after that, I met my wife and was married six months later. In the beginning, our sex life was pretty kinky and adventurous. Before I had even discussed my anal fetish with her, she started fingering my while sucking me off. I told her how much I loved it and wanted to go further which seemed to excite her.
One day, I thought it would be really hot to have her use a toy on me, so I went to the local adult store and bought an anal trainer kit (three progressively larger plugs). We spent a good hour of anal play while I fingered her and ate her out. It was amazing. However, she didn't enjoy it nearly as much as she thought she was going to. After that, she won't even finger me. I've brought it up several times and even posed the idea of having her use a strap-on on me, but she's not going for it.
One week, my wife went out of town to visit her family while I had to stay and work. The first day, I got really horny and jonesing to be filled so I went down to the adult store and bought a realistic dildo that was 7 inches long and 2 inches in diameter with a suction cup base. I played with it the next three days and came harder than I had in ages.
The next night, I started drinking and watching porn. Soon, I found myself looking up videos of guys being penetrated by women wearing strap-ons. I started masturbating and broke out the new toy. For some reason (probably the alcohol) it just wasn't satisfying me.
By this point I had a couple of six packs in my system, so I was feeling very brave (stupid). I got onto craigslist and started looking for a woman interested in giving it to a guy with a strap-on. I did actually find one, but she wanted to go all dominatrix and break out the whips and chains (which I'm not into). A beer or two later, I moved over to the male4male section and posted an ad.
Thirty minutes later, I had several replies. I sifted through them and settled on the guy that seemed the "hottest." About an hour later, he pulled up. I was incredibly nervous/excited to be filled. He was about 5 foot 9 inches, Dominican, and ripped.
I closed the door after letting him in and almost immediately started unbuckling his belt. He took his shirt off as I pulled his pants down. Without even thinking, I dropped to my knees and started licking and sucking his cock. It was even larger than my new toy and felt so hot and magnificent. I sucked his cock for about five minutes before I told him to make himself comfortable and that I would be back with lube and a condom.
I came back naked and started by pouring some lube on his cock and working it a little. I then turned around, spread my cheeks and presented my ass to him. I lubed it up and played with it just enough to get it a little loose (which didn't take long). I got down on all fours as he positioned himself behind me. I've never felt such an amazing rush as I did as he pushed his entire length into me. He took me from behind for a while before asking me to lie on my back, which I did promptly.
He lasted for what seemed like forever. It had to be at least an hour. I came three times from the prostate stimulation alone. Finally, he came deep and hard inside me. We cleaned up, got dressed and told each other what a good time we had and he left. I never saw or talked to him again. I've never before or since felt so sexy and desirable as I did with him.
I have been with two other guys since with less than satisfying results, so I am doubtful that I will ever do it again, but I still fantasize about that night. I guess I will just continue to hold out hope that my wife comes around and decides to indulge in this fantasy with me. Sex with her is great and I have very few complaints, but I will continue to enjoy my little fetish.
By the time I moved out of my parents house, I was pretty adept at pleasing myself anally. I had even learned how to milk my own prostate. I moved to England when I was 18 (the legal drinking age) and found a fancy for the drink. The anal play evolved rapidly with alcohol acting as a catalyst. I started ordering anal toys online. At one point, I had several plugs and a few dildos. They kept getting larger every time I got a new one. My largest plug was 9.75 inches long and 3 inches in diameter at its widest point and the largest dildo was a monstrous 14 inches long and 4 inches in diameter. I had myself trained to take both of these entirely into my rectum.
I moved back to the states three years later for my job and got rid of my collection because I was paranoid of someone finding them while they were in transit.
Shortly after that, I met my wife and was married six months later. In the beginning, our sex life was pretty kinky and adventurous. Before I had even discussed my anal fetish with her, she started fingering my while sucking me off. I told her how much I loved it and wanted to go further which seemed to excite her.
One day, I thought it would be really hot to have her use a toy on me, so I went to the local adult store and bought an anal trainer kit (three progressively larger plugs). We spent a good hour of anal play while I fingered her and ate her out. It was amazing. However, she didn't enjoy it nearly as much as she thought she was going to. After that, she won't even finger me. I've brought it up several times and even posed the idea of having her use a strap-on on me, but she's not going for it.
One week, my wife went out of town to visit her family while I had to stay and work. The first day, I got really horny and jonesing to be filled so I went down to the adult store and bought a realistic dildo that was 7 inches long and 2 inches in diameter with a suction cup base. I played with it the next three days and came harder than I had in ages.
The next night, I started drinking and watching porn. Soon, I found myself looking up videos of guys being penetrated by women wearing strap-ons. I started masturbating and broke out the new toy. For some reason (probably the alcohol) it just wasn't satisfying me.
By this point I had a couple of six packs in my system, so I was feeling very brave (stupid). I got onto craigslist and started looking for a woman interested in giving it to a guy with a strap-on. I did actually find one, but she wanted to go all dominatrix and break out the whips and chains (which I'm not into). A beer or two later, I moved over to the male4male section and posted an ad.
Thirty minutes later, I had several replies. I sifted through them and settled on the guy that seemed the "hottest." About an hour later, he pulled up. I was incredibly nervous/excited to be filled. He was about 5 foot 9 inches, Dominican, and ripped.
I closed the door after letting him in and almost immediately started unbuckling his belt. He took his shirt off as I pulled his pants down. Without even thinking, I dropped to my knees and started licking and sucking his cock. It was even larger than my new toy and felt so hot and magnificent. I sucked his cock for about five minutes before I told him to make himself comfortable and that I would be back with lube and a condom.
I came back naked and started by pouring some lube on his cock and working it a little. I then turned around, spread my cheeks and presented my ass to him. I lubed it up and played with it just enough to get it a little loose (which didn't take long). I got down on all fours as he positioned himself behind me. I've never felt such an amazing rush as I did as he pushed his entire length into me. He took me from behind for a while before asking me to lie on my back, which I did promptly.
He lasted for what seemed like forever. It had to be at least an hour. I came three times from the prostate stimulation alone. Finally, he came deep and hard inside me. We cleaned up, got dressed and told each other what a good time we had and he left. I never saw or talked to him again. I've never before or since felt so sexy and desirable as I did with him.
I have been with two other guys since with less than satisfying results, so I am doubtful that I will ever do it again, but I still fantasize about that night. I guess I will just continue to hold out hope that my wife comes around and decides to indulge in this fantasy with me. Sex with her is great and I have very few complaints, but I will continue to enjoy my little fetish.
- That's Juicy! 46
- Remove It! 1



