Gay Erotic Stories

I have masturbated since I was ten years old, but I‘ve always had to do it in secret because I was taught that it was a shameful act. It was first referred to in the Bible (Genesis 38:9) where it was called “Onanism” and it was considered a sin in those days because the act wasted semen instead of using it for reproduction. Well at the age of ten, I didn’t even know who Onan was or why he was put to death by God for his actions, but I didn’t really care. I just knew that, in my case, Onanism relieved sexual tension and made it easy for me to fall asleep. Besides, I didn’t want to reproduce anyway.

So I have enjoyed masturbation all my life and I have always wished that it didn’t have such a stigma attached to it. I think almost everybody masturbates, especially men, so why should we be so ashamed of it? I believe it’s because our country was founded largely by Puritans and so our laws and imposed morality are based on Puritanical thought that is thoroughly ingrained in all of us. And everybody knows that Puritans don’t masturbate; or at least they wouldn’t admit it if they did.

I’ve never really had an opportunity to masturbate openly except with one girlfriend who also enjoyed masturbation and had no problem with me doing it. Sometimes we would watch porn together and masturbate if the notion struck.

So what’s the deal with men? If most of us masturbate, why won’t we do it together? We watch football together, we drink beer together, and we go to strip clubs together, but suggest one time to your buddies that you guys sit down and jack off together and all of a sudden you’re a queer, a faggot, a homosexual! I maintain that you don’t have to be homosexual to enjoy jacking off together; it should just be a “guy thing.” Did you notice how easily I transitioned from the clinical term “masturbation” to the warm and fuzzy term “jack off?” I think I’ll stick with jack-off.

After this deep contemplation, I decided that rather than jacking off in secret, I wanted to form a group of guys who would enjoy doing it together. So I put an ad in Craigslist looking for potential members. I wanted to name the club “The Circle,” short for “The Circle Jerks.” I thought “The Circle” might be more Politically Correct and wouldn’t raise eyebrows if was seen on a bowling shirt or a team jacket.

I received many responses from interested parties; guys of all ages and orientations. After many e-mail exchanges, I was finally able to set a date that all could attend. The party was to be held on a Saturday at my house. I prepared everything by myself and made sure that I had a variety of DVDs available for my guests along with snacks and drinks. The DVDs included straight porn, gay porn, and even a couple of bestiality flicks.

On the appointed afternoon, my motley crew began showing up. It was quite a cross-section of perverts: a seventy-year-old straight man (Carl), two gay twenty-year-olds (David and Matt), and a thirty-year old transvestite (Dawn). Carl was a big guy that looked like a dock-worker and hardly someone that would participate in a Circle Jerk. He was a nice guy, though; very jovial and outgoing. David and Matt looked like yuppie stock brokers, very well-dressed and with good manners. However, Dawn was the one that interested me the most. He/she actually pulled off the transvestite image with a good figure, breast implants, gorgeous legs, and long, luxurious hair. He/she was also dressed to the nines in a sexy miniskirt and high heels. The other guys treated him/her with respect and even seemed somewhat shy around him/her, as if he was really a woman. He/she explained to us that he was a pre-op transsexual and would complete the transformation when he could afford it. Until then, Dawn was living as a fulltime female at work and in private.

We went through our introductions in the kitchen and spent some time talking about occupations, experiences, and past histories. Carl in particular seemed to take an interest in Dawn and at one point they seemed to be flirting with each other. I brought out the snacks and drinks which were a big hit and a great way to get everyone relaxed and in the mood. When I was able to excuse myself, I went into the living room and put a DVD on the big screen.

As everyone loosened up, they started noticing the sounds coming from the DVD; plenty of “oohs” and “aahs” and “fuck me harder.” I retired to my bedroom to give them some time to let nature take its course and when I came back out, everyone had moved into the living room and were sitting on the couches and chairs in various states of undress. Matt and David had stripped completely and were alternating between stroking their own cocks and stroking each other. Dawn had stripped down to his/her panties and if I didn’t see the bulge in his/her panties, I would swear that she was a woman. Her boobs looked fantastic and her tanned legs were the most beautiful I had ever seen. Old Carl was sitting in his underwear kneading his cock as he watched the gay boys and Dawn. I took my clothes off and threw them in a pile and sat down to stroke my cock.

When he saw that almost everybody was naked, Carl stood up to pull off his underwear and gave all of us a surprise. His cock was at least eight inches long and as thick as my wrist. The gay boys openly complemented him and even Dawn purred his/her approval. I’m sure that he must have felt like the star of the show! Then Dawn decided to take off his/her panties, which captivated all of us. He/she had a small penis and her pubic area was shaved completely bare. It was almost impossible to comprehend! From the waist up, Dawn was a sexy woman, but from the waist down, she was 100% man. Once she was naked, she went over to sit next to Carl. He stroked his long cock, aware that she was watching him closely. At one point, he encouraged her to touch him, which she did willingly. He also reached out to her and fondled her stiffening penis gently as if he were afraid of breaking it off.

I excused myself to get another soda and prepare some more snacks and when I came back, things had taken an interesting turn. Matt was on his knees sucking David’s cock, which I expected to happen eventually, but Carl and Dawn were the real kickers! Carl was on his knees between Dawn’s widespread legs massaging his giant cock. She had her feet on his shoulders and was holding her cock and balls out of the way to expose her asshole. Carl wet his index finger and gently corkscrewed it into Dawn’s ass. She moaned like a bitch in heat which gave Carl the encouragement to replace his finger with the fat head of his cock. Dawn reached down to pull his/her ass-cheeks wide apart to give him full access. I sat down next to them because I didn’t want to miss a thing and I wanted to hold Dawn’s cock and balls out of the way for her. Slowly, Carl pushed the head of cock into Dawn and she grabbed his immense cock to help him. It was unbelievable for me to be sitting there holding a guy’s/girl’s cock in my hand as I watched a monster cock invade her ass. Needless to say, my cock was as hard as a rock and I knew that I would cum the instant I touched it.

Over on the other couch, David was lurching back and forth as Matt sucked a load of cum out of his cock. Matt had been stroking his own cock and blasted a glob of cum into the carpet at the same time that David came. This inspired Carl to drive his cock all the way to the hilt into Dawn’s ass. I released her cock and it draped loosely over Carl’s cock. The scene was too bizarre and erotic to resist and I rose up from the couch to jerk off. I faced Carl and Dawn and when he/she saw that I was on the edge, he/she motioned for me to put it in his/her face. I sort of climbed over Carl’s back to reach Dawn and I barely made it before I started cumming. I got as close as I could to Dawn’s face and he/she opened her mouth wide. I think I made the longest cumshot in my life, my personal best, which landed squarely in Dawn’s gaping mouth. When Carl saw what was happening, he pushed into Dawn forcefully and with one great sigh, unloaded into her asshole. I watched Dawn’s asshole closely which was stretched around Carl’s invading member and it excited me to see Carl’s cum squirt out from around the edges like cream from a Twinkie.

After the excitement was over, it took us a while to clean up. The gay boys retired to the bathroom to shower and get dressed while Carl and Dawn sat on the couch and made out. I wonder if Carl ever imagined in his seventy years that one day he would be making out with a transvestite as he felt his/her shapely tits. And I wondered if Dawn ever imagined that he/she would find an old straight man that would be completely smitten by her and could fuck her into oblivion.

Months later I learned that Carl had financed Dawn’s surgery and that they were making wedding plans. It was a match made in heaven! Or would our Puritan forefathers consider this a match made in Hell? Either way, it looked like they had all made a “Love Connection” and I was happy for them. Of course, I’m still here jacking off by myself.

Well, my Circle Jerk had exceeded all expectations and we agreed to make this an ongoing event. I agreed to keep looking for newcomers to participate although I don’t think I’ll ever find a more strange and diversified group to participate in “Th