Welcome to the Circle

by Cleanshaven

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma, Consensual, Gay, TransGender, Orgy, Oral Sex, Anal Sex, Masturbation, .

Desc: Erotica Sex Story: A masturbation club attracts a diverse group of guys who are out to have kinky fun!

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 former 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 personal 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.

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Story tagged with:
Ma/Ma / Consensual / Gay / TransGender / Orgy / Oral Sex / Anal Sex / Masturbation /