Mixed-Gender Circle Jerk

by Jeremy J. Watson

What you are about to read is entirely true. Only the names and locations have been changed.

My wife has gone through some hormonal changes which left her uninterested in sex. We talked about me getting my sexual satisfaction elsewhere. At first she was reluctant to accept my idea. I’m a high libido person. I explained to her that I’d love her forever, and wouldn’t run off or anything, but I needed something more.

She replied that it might work out to her advantage, after all, because I’d stop pestering her to ‘put out.’ I’m somewhat bisexual, and she thought it might be better if I would just focus on hanging out with guys. I said I couldn’t guarantee it, but I’d give it a try.

A couple of days later, I was looking on Craigslist, in the Personals section, and then under Casual Encounters.

It seemed like I struck a goldmine, there were literally over a hundred ads from mostly guys, looking for no strings attached encounters.

Most were not to my liking. I guess you’d call me bisexual, but in a strange sense. I have no interest in kissing guys, oral sex, anal sex, or even frotting – rubbing bodies together. I’m a handjob guy when it comes to men.

On the other hand, with my wife, in earlier years, we did everything, and I fully enjoyed it. Oral both ways, hugging, kissing, even buttfucking, which seemed to give her almost instant orgasms, while she seldom had orgasms from ordinary sex.

She wasn’t quite as experimental as I have been. I like exploring techniques. I’ve played with BDSM, electro stimulation, even sounding – sticking things in one’s peehole. Having experienced all that, these days, I’m really more interested in the simpler manual things, like glans rubbing, testicle massage, anal fingering, and of course handjobs. For instance, I have found that with me, and many other men, simply pulling on the frenulum and holding it awhile can bring on an ejaculation.

Most of the guys advertising on Craigslist wanted kissing, anal sex, and most of all, they seemed to want to give and get blowjobs.

One day, I came across an ad that made sense to me. It was simply stated in about two sentences. A guy wanted to trade handjobs. He was ten years younger than me at 44 years old, taller than me, thin, and good looking with sparkly eyes and long, dark hair. His hair was tied in a pony tail that ended half-way down his back. He had a neatly trimmed goatee. I didn’t know much about his appearance at first, because by email all we did was trade cock pictures, as is the way it is generally done via Craigslist.

We made arrangements, and I came over to his RV. I knocked on the door. It was answered by a short, slightly heavyset woman. ‘What the fuck?’ I was thinking.

She invited me in, and I sat down tentatively on the edge of her sofa, ready to jump out, and go home at the slightest irregularity. I’m sure you get the idea. When meeting someone new for a sexual encounter, you do tend to worry that they might be weird, or have their own screwed-up agenda.

Actually, it’s safer to meet someone for sex through Craigslist, than for buying a used car. Why? Because the car buyer is bristling with cash. There are people out there who’d like to take that, even if force is required. With sex, there’s no cash to be taken.

Her husband came from the bedroom into the living area after a few seconds. He was as advertised. I hadn’t seen face pictures, but he matched his description. But what about this woman? What was the deal?

She did the talking, and explained it to me in just a few minutes. It seems her husband, Charles, isn’t computer literate. He’s also shy. So, she took it upon herself to place the ad for him. He didn’t know she was going to place the ad, but they had talked about his bisexual interests, and he knew she was thinking of arranging something, someday.

So, when I responded to the ad, and emailed back and forth a few times to set it up, I was corresponding with her, masquerading as him.

Charles started pulling off his clothes, right there in the middle of the RV. His totally shaved penis was already hard. It was rather attractive. Circumcised, and somewhat bigger than average. I’m exactly average, and also circumcised.

When in Rome, right? So I took off my T-shirt and shorts, also. I had arrived freeballing, so there was no underwear to remove. I wasn’t hard yet, still being a bit freaked out by this unexpected situation.

The truth is, anytime I’m in a new sexual situation, it takes me a while to get hard. But when I do, I get fully hard and stay that way. Why it takes a while, I don’t know. My theory is that I have spent a lot of time in locker rooms and on nude beaches, where having an erection would be totally embarrassing. I have trained myself not to get hard in front of strangers, so it takes a while to overcome that.

I invited the wife, Sue, to join us, but she politely declined. I was thinking it would be nice to have her watch, at least. Because, other than the delayed erection thing, I do get a kick out of people watching me, seeing me play and having an erection waving all around.

Charles, who doesn’t like to be “Chuck,” “Charlie,” or anything like that, guided me to the bedroom in the RV, while she stayed in the main living area and started watching a movie. ‘Oh, well,’ I thought. ‘I hadn’t been expecting anything more anyway, and it would be fun to play with Charles.’

His wife was mostly truthful. He was satisfied with a handjob, as was I. I tried to explain to Charles that it would be particularly fun for me if he’d give me a testicle massage, pull on my frenulum, rub my glans, and other ‘non-standard’ techniques, and he said ‘sure’ but then didn’t do any of those things.

As for him, he asked me whether I would buttfuck him. I declined, and he was OK with that. I started in on a very gentle testicle massage, which he enjoyed. I went a little firmer, and I mean just a little bit, and he said it was too much for him. I started stroking him up and down, I just got started when he came way too soon.

He was done, and I hadn’t cum. That’s OK, really. I’ve learned over the years that not cumming, which I used to think would be some sort of torture, works out just fine. You stay sexually charged for the rest of the day, until you can jerk off later, which has its advantages.

I thanked both of them, and went home, figuring that was the last with Sue and Charles.

A week later, they invited me back. I was somewhat reluctant, but also somewhat horny. I figured if it was only a repeat of the last time, it would be better than nothing, so I went on over.

Charles greeted me at the door this time. We went in, and made small talk for a good ten minutes, fully clothed. I tried to urge him to get something going, but it wasn’t happening. He was reluctant to get started for some reason. Meanwhile, I assumed Sue was not at home. Then I felt the RV move a little bit, and figured out she had been in the bathroom the whole time.

She came out a few minutes later, totally nude. She had been in there shaving everything but the hair on her head. Now I knew why Charles was delaying. She was going to play with us!

Now Sue isn’t your typical pretty girl. Oh, she’s cute, with dimples, a pretty smile, and a wide, innocent face surrounded by long, straight black hair. But, she weighs somewhat more than you might call ideal. Not a lot more. Some guys would call her curvy.

I noticed something strange right away. She had a flap of skin hanging all the way across her belly. Being quite unusual, I asked her about it.

“Oh, I used to weigh over 300 pounds.”

I was astounded. “What happened? How did you manage to lose so much weight?”

“I just decided.” She seemed to act like it was easy to do.

Evidently, when one weighs that much, the skin stretches to accommodate, but does not unstretch when the weight is lost. She was still attractive to me. Frankly, any woman, when totally naked, delights me.

The three of us went to the bedroom, and us two guys removed our stuff. Charles was hard right away again, I was soft.

At first Sue only wanted to watch. I was only half-disappointed, because again it was more than I had been expecting. Plus, as I have mentioned, I like being watched. I guess I’m a bit of an exhibitionist.

I had Charles lay on the bed with his legs hanging off the edge. I slowly introduced one lubed finger into his ass. His penis twitched with anticipation. Once the finger was all the way in, I just started gently stroking him. Bang! He came again, way too soon. I was surprised how much cum landed on his belly. It was maybe ten long squirts. Unfortunately, that finished him off.

You probably know that most guys lose their erections, and their interest, right after ejaculating. In fact, most guys can’t stand to have their dicks touched for at least fifteen minutes, if not for days afterward.

He excused himself to go watch TV in the front room. I was not entirely sure it was OK to play with Sue, so I asked.

Charles was like, “Oh, yes, she’s been hoping…”

I didn’t feel right just fucking Sue. Plus, I really am more of a handjob guy. I asked what she liked, and she said she liked having her nipples rubbed lightly, then later, pinched quite hard. She wanted clit rubbing, and she wanted to try fisting. I started with her erect pink nipples on her ample breasts, and she was immediately in heaven. I rubbed her clitoris a bit, and she was even happier. I found that she was self-lubricating, and used that for ongoing clit rubbing. She started to get close to orgasm, and thinking she might be a woman who enjoys edging, I stopped, planning to do more later.

Then she turned her attention to me. She asked what I liked. I told her, and she went to work. She lubed up her small hands, and started right in with glans rubbing. Ordinarily a very squirmy or seriously ticklish sensation, it was even worse because I was still not erect. I asked her to come back to that later.

So, she started massaging my balls. She was gentle. I don’t always like gentle. I asked her to increase the pressure, squeezing my balls between her thumbs and first two fingers, one ball in each hand, until I said it was too much. Slowly, she worked up to where it was painful, then backed off just the right amount.

I can cum from good testicle massage, no penis manipulation needed. So when I was getting close, I had her stop. By now, I was fully erect. Way, super-solid erect! She had done a great job on the testicle massage, explaining that Charles likes everything conservative and soft. She was delighted that I was experimental and liked things rougher.

Turning the attention back on her, we worked on fisting for a while. Charles had always refused to do that to her. Not only did he like gentle treatment, he didn’t like treating her rough, even if she wanted it, she explained. As we were fisting, she moaned, and even shrieked, which had me trying to stop, but she wanted me to keep going. She was loving trying to take my whole fist in her pussy. But it wasn’t happening. I only got four fingers in. However, she did start orgasming during the process. I could feel her slight jittering and contractions, which turned me on even more. I kept going, just with the four fingers, and added clit rubbing with my other hand. Unlike most women, but like some I have known, Sue could have back-to-back, or essentially continuous orgasms. I just kept going until she finally settled down.

Early in the fisting, when I had only inserted two fingers, I started feeling around for her cervix and couldn’t find it. Asking about that, she explained that she had had a hysterectomy.

When I was younger, with one of my first girlfriends, I had been fingering inside her pussy, and found a big bump in there. I was sure it was a tumor, and didn’t know whether I should tell her, or what. Fortunately, before I opened my stupid mouth, I figured out that it was the cervix, something I had read about, but hadn’t discovered in person.

I asked if Sue was done.

“Hell no.” She wanted to do more to me. Of course I was all for that.

Something she wanted to try was to see if she could jam her little finger in my peehole. I was totally delighted that she wanted to try.

She coated her hands, and the tip of my penis, with hydrogen peroxide. I’m glad she did, because this sort of thing can bring on a nasty infection if one isn’t careful to be sterile.

After putting a generous amount of lube on the tip of my dick and on her little finger, she slowly introduced it into my peehole. I enjoyed the stretching feeling as she quickly got her finger in half-way to the first knuckle, or a little less than a half inch.

Then, it was tough going. She pushed, and twisted, and I was on the verge of pain, but we both wanted to keep going. It took a while, when suddenly, “pop” Her first knuckle slipped in. That was just too exciting for me, and I started ejaculating right then and there. Nothing came out of me, because my urethra was plugged with her finger. That caused me to keep contracting for about twice as long as the usual orgasm. When it was over, she slowly pulled her finger out. Now, that hurt! The sting was pretty severe, but when she was done, my juice flowed out, and I was relieved. Also quite happy. Weird though it was, I had a great time!

We got together a couple more times. She turned out to like anal fingering. Charles managed to last longer. He also talked me into buttfucking him once. That’s usually not my thing, but I was happy to comply, especially with Sue laying right there watching. She put the condom on my fully hard penis while Charles got on all fours with his butt up in the air.

I slowly applied pressure, and his butt accommodated me nicely. I started stroking in and out, while his wife reached under him, wrapping his fingers around his penis, and jerking him off. He came too soon again, in my opinion. Again, he came volumes, completely wetting the sheets. Shortly afterward, I slowly pulled out.

From experience I knew that when an object is pulled out of a man’s ass quickly, it is a real eye-opener, and not necessarily pleasantly so.

Sue then started playing with my dick and my balls, as Charles went back to the TV in the main room. Soon, I came.

Later, I became concerned because I didn’t remember removing the rubber. I think it must have unrolled in Charles’ rectum. I’m glad I was the guy fucking him, because I know I’m clean. I haven’t been buttfucked since I was a teenager, and don’t intend to experience that any time soon, or ever. Oh, it can be enjoyable, but there are so many other things, better things in my opinion, that people can do, that there’s no need to take any risks.

I’d like to tell you that Sue, Charles and I played for years afterward, but shortly thereafter, she went to Seattle to help with one of her grandchildren. She stayed for weeks, while Charles started to freak out. Sure enough, one day she phoned him, saying she wasn’t coming back.

He came to my place crying and crying. He was a good man. I don’t know what went wrong with them, but in my opinion, Sue really lost out.

That was the last I saw of them.

That’s not the story I want to tell you about, however. This recent one really was a mixed-gender circle jerk.

I saw the posting on Craigslist. The writer spelled out the arrangement: It was expected to be approximately eight men, and possibly, just possibly a woman. No one was to touch anyone else without permission. Especially, if the woman showed up, no one was to do anything with her without her explicit permission.

I was good with all that. Very good. Even if the woman didn’t show up, I knew I’d have a good time. I like circle jerks.

Speaking of circle jerks, I attended the Masturbate-A-Thon in San Francisco three years in a row. This event was like a walk-a-thon, or a bike-a-thon, in which the participants gather pledges for charity based on performance. However, for this, rather than an amount of money per mile, it was amount per minute, or for some, amount per orgasm. If one could get any pledges at all, the admission was free. Otherwise, people could just pay $40, and enter without pledges. The money they gathered went to several good social programs, including the Center for Sex and Culture, which supports positive sexual education.

As soon as I saw the listing on the Internet, I was excited beyond words! I thought it would be nice to remain closeted as it were, and just pay the $40. But the more I thought about it, the more I aligned with their mission, which was to educate people on sexual health, including the still new idea that masturbation is not only a good practice, but good for one’s physical and mental health.

Among other things, masturbation allows people to reduce frustration, thereby eliminating unnecessary or ungood sex, which reduces incidence of sexually transmitted diseases and unwanted pregnancies. I was all for that, and if my attempt to get sponsors would help promote the message, that was all for the good.

At first reluctantly, I carefully brought the topic up with my friends and coworkers. I thought they might make fun of me, or say I was a ‘weirdo’ or worse. To my surprise, every single person I asked, about forty people in all, were supportive. Most admitting that they enjoy masturbation. Many may have admitted that for the first time out loud. I got eight sponsors. I asked most of the forty people whether they might like to attend also. I thought it would be nice to have their company at this event. I mean, how cool would it be to be naked and jerk off with your coworkers?

The only one who was willing to attend was my wife. That surprised me, because she hadn’t been sexual for quite a while. Then, the day before the event, she backed out, and told me I couldn’t go. I went anyway!

I arrived early. I couldn’t help myself. I was just too excited. Knocking on the door of the old warehouse where it was to be held, I was met by a small, young woman with very short, curly black hair. I told her I’d like to volunteer to help set up. She told me to wait, while she went inside to ask whether they wanted a volunteer. She came back, and let me in.

I went up a junky old metal stairwell, that led into a sort of foyer, with some doors and an old industrial hallway. Walking through one of the doors to a huge room with a paper sign that said “Masturbatorium,” I saw about a dozen other volunteers setting things up. Most of the volunteers were normally clothed, but one of the volunteers was fully nude, and was sporting an erection. He was standing on a step ladder, stringing a microphone wire through the rigging in the ceiling. He looked vaguely familiar.

I kept wondering if I knew the guy on the ladder, and then it dawned on me. He looked just like a well-known television personality.

I took off all my clothes and laid them over a nearby chair, then asked the guy how I could help. First, he put me on floor sweeping detail. I was to run an industrial but hand-pushed carpet sweeper-like thing throughout the room, picking up any foreign material that might bother people’s feet. That took quite a while because the room was very large.

Upon completing that task, I put my clothes back on. I felt funny being only one of two naked people around everyone else being clothed.

I accompanied the fellow down a freight elevator to the street. We each had an empty hand truck. We were to pick up cartons of drinks and snacks, and bring them back upstairs. As the back elevator door opened, I realized it faced directly on the sidewalk of a busy boulevard. He stepped right out, as naked as the day he was born. Worse, he was still fully erect.

“Aren’t you worried about being seen like that?” I asked.

“This is San Francisco!”

Then I asked, “Aren’t you…” and I said his name.

“Yes, I am.”

“Don’t you worry that people will recognize you?”

“Funny thing about that. They always think I’m someone who looks like me, but that I’m not me. I don’t tell them otherwise.

“But, if you don’t mind, I’d like to keep my participation here a secret. It could be bad for my career.”

Of course, I told him I’d keep his secret.

We returned to the warehouse and helped a video crew set up their cables and lights.

Soon, members of the public started straggling in. Then, a torrent came in, and pretty soon, there were around 120 people in the building. There was a coat check room that was actually a clothes check room manned by volunteers. People started exchanging all their clothes for wrist bands. Soon, all 120 of us were naked, and milling around, making brief, hesitant introductions, and essentially waiting for instructions.

There were people of all descriptions, but most seemed like well-educated, upwardly-mobile young people. One woman was in her eighties. I thought it very impressive of her to show up for this. Approximately seventy percent of the group were male, and of course thirty percent female.

Most of the volunteers I had met earlier, plus some others who came in later, were psychology graduates. In order to get hired as psychologists in the state of California they needed to put in 2,500 hours of internship. This even would qualify for some of those hours. The Masturbate-A-Thon was conceived of, and run by two well-known sex researchers with PhDs in psychology. The interns were all quite young.

Finally, one of the organizers grabbed a microphone and told us the details. We were wanking for charity. Most of the participants were going for minutes, but a few for orgasms. For those who were counting orgasms, there’d be volunteers to watch and confirm. Everyone else would masturbate for 55 minutes out of every hour, and have a five minute bathroon and refreshment break. No one could touch anyone else. Anyone who wanted to be recorded for the live video stream or files that would be available on the Internet afterward had to sign a waiver, and get a second wrist band.

Like everyone else, I signed in, then somewhat nervously disrobed and signed the video waiver. I had no intention of being on camera, but, well, just in case.

A whistle blew, and people started wanking. Some were reclining on a wide assortment of sheet-covered furniture or pads on the floor. Some were standing. Natural groups formed, where, for instance, a dozen guys were sitting cross-legged on the floor, and talking about motorcycle technology as they wanked.

No one was supposed to touch anyone else, but there was a lot of rule-breaking the first time I attended. In subsequent years, that was more clearly enforced.

Many of the volunteers became participants. The small, short-haired girl who had greeted me at the door was naked throughout most of the evening, and at one point she demonstrated how she masturbates, taking herself rapidly through all the stages, and having a nice, wet orgasm in front of an audience of about fifteen guys.

There was entertainment. There were several fully-clothed bands playing very nice music in the main room. If one wanted to converse, there were other rooms off to the sides, where a number of people gathered.

There were several stars from the porn industry who got on stage and did things like pole dancing, or reading homemade poetry while nude.

One poor guy, evidently a porn star that I didn’t recognize, tried getting hard and masturbating on stage in front of everyone, but it wasn’t working. He couldn’t get erect.

I saw a beautiful red-headed woman who was laying on a pad on the floor on her belly. She had her hand underneath and was wanking blissfully. Her ass was facing up, and her legs were spread in such a way that her little pink asshole was on full display. I almost lost it and ejaculated while seeing that.

At one point, Nina Hartley, a famous star from the 1990s was on stage. She was entirely naked except for Xs made from black electrical tape on her nipples. I didn’t understand the fashion, but liked seeing the rest of her fully naked.

She asked for volunteers. To my own surprise, my hand shot up in a second, and she invited me up.

Suddenly, I was in the lights and being filmed for an unknown crowd across the world. Every one watching the Masturbate-a-thon live saw me. It might have been a few hundred viewers, or it might have been tens of thousands. You’d think I would have been nervous, but no, I was just enthralled to be with Nina Hartley under such circumstances.

“What do you like?” she asked.

I said the first thing that came to mind. “I like testicle massage.”

She had me sit in a folding chair and knelt in front of me, as two guys with huge TV cameras supported on their shoulders moved in for close shots. She started massaging my balls in front of the whole crowd there, plus all the Internet viewers. The exhibitionist in me was absolutely delighted. She didn’t touch my dick, and that’s a good thing, because if she did, I probably would have ejaculated instantly. She massaged my balls perfectly, applying just the right amount of pressure.

All too soon, that was over, and she invited another guy up.

“What do you like?” she asked him.

He said he wanted a blowjob, and she proceeded to give him just that. If only I had known she was willing to break the rule in that way at the Masturbate-A-Thon! From her, I’d happily have accepted a blowjob. But, I was happy with the testicle massage by Nina Hartley. Very happy. I’ll remember it for the rest of my life!

A few men ejaculated quickly, then left. Others, such as myself, were having such a great time, we wanted it to last. To my own amusement, I lasted eight hours and twenty minutes, ending up in the early hours of the morning, with only around ten people left, most of which were volunteers. If I had only known, I might have had the record that year. The winner lasted eight hours and forty-some minutes. But, then, I wasn’t interested in a record, and certainly not interested in the publicity that came with it.

The second and third years I attended were just as good.

But that, too, isn’t what this story is about. Just recently, I attended the mixed-gender circle jerk I mentioned earlier.

It was held in a motel room. I was the second to arrive, so there were three men to start with. We disrobed quickly and started wanking while watching some porn on the large TV to which the host had hooked his laptop.

The other guy asked if either the host or I would like a blowjob. I usually don’t care for such things, but this time, it felt right, so I said yes. I laid on the bed with my feet hanging off the end, while he knelt on the floor and went to work. I hardened quickly, unusual for me. As he was sucking away, two more guys were let in. The first thing they saw as they entered was me getting my dick sucked. I was somehow proud of that, but it was a bit weird too. Other guests or hotel staff could have walked by the door while it was open, and they certainly would have seen me all naked and erect. Perhaps people did.

In a while, a total of ten guys arrived, and we were all jerking off, watching porn, or other related activities. There were a few blowjobs going on, and one pair of strangers, foolishly in my opinion, were buttfucking without protection.

About twenty minutes after the starting time, there was one more knock at the door. It was Lilly. She was a bit on the older side, perhaps forty-five years old, but still looking like a million bucks. She seemed to be of dark Italian descent, had large breasts, and was short and otherwise skinny, with long black hair. A dreamboat, actually.

I have been amazed over the years that someone like that would attend an event like this, but have seen it many times. Evidently, she likes casual sex as much as many men do. Either that, or she was a true nymphomaniac. Or both.

I knew a nympho once. I was twenty-three at the time, and she was nineteen. She was remarkably tall at six feet and one-half inch tall. Technically, any woman over five-eleven is a giant. Did you know that? I was a couple of inches shorter than her. She looked quite a lot like Wonder Woman. At first, I wondered what she saw in me. With her outgoing personality and great smile, not to mention her extreme interest in sex, she could have had any guy.

But she was not quite right. The day we met, we fucked. Twice. Then every day, she wanted to fuck. She was wearing me out. She’d come over after work – she was a television camerawoman – and we’d fuck until eleven o’clock. Then she’d come back at three in the morning, uninvited, waking me up and wanting more.

After two weeks, I gave up, and introduced her to a virgin friend of mine. He was delighted, at first.

So Lilly showed up at the circle jerk, and didn’t immediately take off her clothes. I was feeling a touch of frustration. Although I was enjoying the guys, I’m more hetero than homo, and would have really enjoyed seeing her nude, if nothing else.

The room was warm. The air conditioner couldn’t keep up with the heat generated by all the people, so soon, Lilly was down to her bra and panties. Shortly after that, she was totally naked. It was great seeing her, especially those large boobs of hers topped by large diameter, dark, erect nipples.

The host, who seemed to be acquainted with her, held her on his lap and they kissed for quite a while. Then she got on the bed, as I and a couple other guys moved aside, and put a condom on the host. They fucked, while us guys stood around, enjoying the show, and idly masturbated ourselves.

The host blew his load, then another guy condomed up, and fucked Lilly. All in all, one after another, she took about six guys.

I wanted to participate but didn’t want to fuck. While a guy was fucking her, I placed my finger against her asshole, but didn’t press in, kind of asking permission. She nodded her head while looking at me, so I took that as “Yes!”

Lubed up with her own juice, I pressed my finger all the way in, and suddenly she had her first orgasm of the evening.

The man who had been fucking her came, and pulled out. The host came back, and while my finger was still in her ass, and she was still calming down from that orgasm, he placed two fingers in her pussy and curled them upward, finding her G-spot. The two of us got her off to another crashing orgasm.

Soon every man had cum, and we all went home, quite happy.

All of that, for better or worse, is the truth.

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