A Totally True Memoir
by Jeremy J. Watson
I’ve known a couple for a while, a happily married man and woman just over forty years old. The three of us play with a strange kind of sex from time to time.
The man, Jerry, likes gentle things, which is contrary to what you might think from looking at him. He’s well over six feet tall, built strong, not fat, has longish hair and keeps his dark beard neatly trimmed. He has a typical number of tattoos. Although he has a kind expression, he doesn’t look like a guy you’d want to get in a fight with. When you see him without clothes, you are shocked to discover that he likes to keep everything shaved. Not only his crotch and ass, but his chest, underarms, upper arms and legs, too.
He mostly likes masturbatory things. He enjoys light stroking, tickling, very light touching of his scrotum, and especially frenulum pulling. That’s the little crease of skin on the bottom of the penis, just below the head. The minute his clothes are off, he’s rock hard.
Jerry’s wife, Monique, is short, a bit on the heavy side, and keeps her dark hair cut close. Unlike Jerry, she likes it rough. We have played with fisting, although I haven’t managed to get my hand all the way in her pussy yet. She also likes rough rubbing of her clit, and will have long, continuous orgasms.
Monique is quite attractive, as long as you don’t mind some weight. It helps make her breasts appealingly large. She has actually lost weight. A lot of weight. She says at one point she weighed over 300 pounds. You might not believe it seeing her now, until she takes her clothes off. You definitely believe it when you see the huge unexpected flap of loose skin that hangs over her belly, the last remnant of when it had to enclose a lot more body. She’s also had some things happen in her life. For instance, at just over forty years old, she already has two grown daughters.
One day, she really surprised me. I was sticking my fingers into her vagina as far as they would go. This was just before we started playing with fisting. Feeling around, I couldn’t find her cervix. That’s how I found out she had a hysterectomy.
I’m no special specimen myself. I’m older than this couple at just over 60, but in great health. I think it has to do with eating well, keeping a good attitude, and playing a lot of sports. I’m about as normal as you can get. I’m bearded, balding, most of my formerly brown hair is gray, and I’m average height and weight.
My one oddity is some lumps in my scrotum. Now, don’t be alarmed, they are just harmless cysts that have been there for more that 20 years. But when I start playing with people, I like to tell them, so when they first discover the lumps, they don’t think anything is wrong with me. I think the lumps came from having my balls tied so tight they’d turn blue, something I used to enjoy many years ago. When the bondage is released, they feel interestingly tingly as the blood starts flowing again. I believe the cord I used at one time or another may have been too thin, causing slight damage to the spermatic cords, resulting in the cysts.
You may be wondering how a guy who’s sixty-one years old came to be sexually involved with a couple who are forty-one and forty-three. I’m quite amazed myself that it happened.
I was looking over the Casual Encounters section of Craigslist, hoping to find someone interesting to play with. I had done it four times before, always finding a bisexual man who didn’t mind mutual masturbation, my favorite hobby.
I’m bisexual myself, leaning more toward women. I love my wife, and don’t want to jeopardize our marriage. My wife has gone through some sort of hormonal shift and so no longer enjoys sex. We’ve tried everything, to no avail. She finally told me to go out and find someone else safe to play with, as long as the sexual stuff didn’t interfere with our marriage. I was all for that!
I figured out that finding a woman to play with through Craigslist, or any other way, could be problematic. In my experience, women want everything to turn into a relationship. I only wanted a sexual playmate. It turns out men are generally better at casual get-togethers.
There was a posting from a man in my neighborhood. We exchanged cock pictures, and arranged a time. Feeling a bit nervous, and slightly weak in the knees, I showed up at his door, and was shocked when a woman answered. That woman was Monique. She invited me in, as I was trying to figure out how to ask whether I had the right place, without revealing I was coming to play sexually with a guy.
She answered that question quickly, as she explained what was going on. It turns out that Jerry didn’t place the ad on Craigslist. She wrote and posted it. She said he had wanted to explore bisexuality for a long time, and she decided to help him make it become real.
During our email correspondence, I made it clear that I was over sixty, and to my surprise, and delight, Jerry wanted an older guy, and Monique, too, seems to be more comfortable with people old enough to be her parents.
OK, I was on board with that! In fact, I was thinking how cool it would be if she’d watch.
As Monique was finishing her explanation, Jerry appeared from a back bedroom stark naked, and walking toward us with his fully shaved boner waving back and forth. I guess he was ready for me! Jerry and I shook hands, made a moment of small talk, and went to their bedroom, I was hoping Monique would follow, but she didn’t, turning to a movie on their TV instead. Oh, well. I’d still have at least as good a time as I was expecting with Jerry. She would have been the frosting on the cake.
So, in the bedroom, I took everything off, and Jerry and I played. I quickly learned how gentle he likes things. At one point, I grabbed his balls through his scrotum in one hand, squeezing what I thought was lightly. He yelled and jumped off the bed. I apologized, and handled him like a little kitten from that point forward.
I, on the other hand, like fairly firm testicle massage, solid frenulum and scrotum pulling, and what the Japanese call glans blame, otherwise know as apple polishing in the United States. That’s where someone puts lube on the palm of their hand, grabs your shaft with their other hand, and rubs that palm all over the glans, the tip, of your penis.
If you’ve never had it done, you’re in for a treat, maybe. Some guys love it, others don’t. You see, it makes your squirm terribly. In fact, some men have to be tied down in order to stay put, otherwise, they’ll wiggle away. But if you can take it, what starts out as a nearly unbearable tickle-like effect eventually transmutes into a sort of gotta-pee feeling mixed with gonna-cum. In most cases, neither thing happens. You stay in a sort of pre-orgasmic state for quite a while. Sometimes guys will cum, and one guy I played with years ago actually couldn’t help himself and let out some pee during glans rubbing. But most, if they can take it, love the feeling. I’m one of those guys.
I explained to Jerry how I like glans blame and the other things, but try as I might, I couldn’t get him to do the things I wanted. He just kept wanting to blow me. I don’t mind a good blowjob, but there’s so much more to life.
So, he and I were doing our thing, and I was enjoying it, but also thinking to myself, he’s not quite the right guy for me on an ongoing basis. About then, Monique came in. She was fully clothed, I explicitly invited her to play with us, but she declined, saying maybe next time. Instead, she sat on the edge of the bed and watched us play, which I found very hot, and before long, Jerry came in my hand, and I came in his mouth.
I thought that was a one-off, but three days later, I got a call from Monique. It seems Jerry had a very good time, and wanted more. I was thinking of declining, but then remembered that Monique might, possibly be willing to play with us. I felt I couldn’t just come right out on the phone and ask her if she was going to get more involved this time. I probably should have asked, and probably could have, but I didn’t.
I showed up at their place merely hoping that Monique would play this time, and figuring I’d still have a reasonably good time with Jerry, if not.
Jerry answered the door this time, and Monique was nowhere in sight. He and I sat on a sofa talking for a bit. He offered a beer which I declined. Having grown up with an embarrassingly drunken father, I decided long ago not to drink, even beers. We talked more than I thought was right for the occasion, yet he made no move to go to the bedroom.
Finally, I found out why. Monique had been in the bathroom shaving every bit of hair off her entire body except for her head. She had just run a bit late getting ready for me. She walked into the living room as naked as the day she was born, and at that moment, I knew it was going to be a good afternoon indeed.
That’s when I found out she’s the one I really liked playing with. She likes it rough, and I guess I do too.
The three of us went to their king-size bed and started rolling all around. She wanted to start by me giving Jerry a handjob. That’s what she really wanted to see, so he and I complied. He seemed close to cumming, so I stopped. Now, he started almost begging me to butt fuck him. That’s not something I normally like to do. I’m really more of a handjob guy, but since she was really interested in watching her husband get fucked by a guy, and since I was pretty horned up, I acquiesced. Jerry handed me a rubber which I put on. He got on his hands and knees, while I got on my knees behind him.
Knowing his preference for gentleness, I started very slowly, by just running my fingertip around his anus barely touching it at all, and not touching the middle of the anus itself. He moaned unintelligibly, but in a way that let me know he was very much enjoying that. I continued for a while, then touched the exact center of his asshole with my fingertip. Meanwhile, Monique was watching with very big eyes.
In time, I lubed my finger, and ever so slowly introduced it into his ass. He was obviously in heaven. I noticed that pre-cum was falling off his very erect dick which was pointed toward the bed. The pre-cum had formed a puddle about two inches in diameter that was soaking into the sheets.
I worked up to two fingers, and he seemed not only alright with it, but was enjoying it entirely. It was now time for the big event. My penis was a bit soft at first, so it took a bit of doing, but finally, I got the tip popped into his butt. Monique was watching very closely, and idly massaging a nipple with one hand, and rubbing her clit with the other.
My penis fully hardened at that point, and I worked it fully into Jerry. I have to admit that feeling the guy’s butt squeezed tightly around my dick felt very nice.
I’m pretty good at holding my cum, and was prepared to fuck him for an hour, but unfortunately no sooner did I get my dick all the way in then I started feeling his inner muscles pumping. He ejaculated all over the bed.
I slowly pulled out of him, and to my horror, the rubber was gone. I had put it on, but where was it now? I looked around on the bedding but it was nowhere to be found. It must have unrolled inside of Jerry. Now, I knew the likelihood of catching something as the fucker is much less than the fuckee, and I knew I was clean, but just the idea that a rubber could fail that badly bothered me. I can only imagine his surprise when he next went to poop, and out popped the rubber!
Shortly after, he said he enjoyed that very much, got up, walked toward the door, telling Monique and I over his shoulder that he wanted us to keep playing, and he went off to watch TV or something.
This was a great turn of events!
Monique asked what I would like. I told her my preferences, and she was more delighted than I would have thought. It seems, she likes it kind of rough also, and Jerry has never been her cup of tea, sexually. She has asked him repeatedly to fuck her harder, rub her harder, try new experiments, and so on, but he only wants plain old fucking, every time. Now, here I was, willing to be crazy along with her.
That’s when we got into the fisting and all that. I was really surprised how hard she wanted her clit rubbed, then surprised again when her orgasm went on and on. I had to ask afterward if that was really happening, because I had never seen it before.
Most women I have know fall into one of two groups. Either they come once, like a guy, and then they are done, or they can have multiple orgasms, but each orgasm happens in a discrete moment of time. She assured me that it was one long orgasm. She was really bucking shaking the whole time, so I can only assume as long as it was, that the whole thing was at least as strong as any ordinary orgasm.
Now, Monique turned her attention to me. She blew me a bit, and I hardened. She knew already, that oral wasn’t my favorite thing. I had told her about ball massage and glans rubbing. But she didn’t go for that right away. Instead, she had something of her own she wanted to try, and I was all for it.
She opened a bottle of rubbing alcohol that she just happened to have in her nightstand. (How long had she been planning for a moment like this?) She coated her little finger and the whole top of my penis with alcohol and let them dry. The cooling effect of alcohol on a penis is interesting. However, don’t let it get in your peehole, it can sting a bit.
Then she applied a liberal about of sterile lube to my peehole and the tip of her finger. I was shaking in anticipation, and perhaps a bit of fear. Would it hurt too much? She started pressing her fingertip against my peehole. I felt her fingernail digging in a bit, and said “Ouch.” She changed her position, and that problem went away. Now, it felt nothing but good. I felt my peehole being stretched like it never had before. She twisted her fingertip back and forth a bit, which did sting just a little, but the pleasure far outweighed the pain. She kept going, and it felt really good. If I was one to orgasm easily, I could have cum just from that.
I asked her if she was alright with what she was doing, giving me her full attention like that, and getting nothing in return. She assured me that she was getting a lot in return. She was absolutely fascinated by the idea of fucking my peehole with her finger.
She kept pushing and twisting. Now, it was starting to hurt, but still, not so much that I wanted her to stop. Suddenly, pop! It wasn’t an audible sound, but I could certainly feel a pop as her first knuckle suddenly made it through my badly stretched peehole and into my urethra. She felt the pop too, and it scared her a bit, so she immediately pulled her finger back out. Now that stung! Woah!
Next on the agenda was ball squeezing. She squished my balls this way and that with her thumbs and forefingers. Now, I realize that’s not for everyone, but I loved it. I had her start lightly, then build the pressure more and more. I had to instruct Monique not to press on the top area behind my balls where the cords attach. That part is just too sensitive. Once she got that, she was able to massage those testicles of mine quite firmly. She was incredulous that a guy could take that amount of pressure. Her experience with Jerry had led her to believe that a guy didn’t like any ball pressure at all.
I explained that a little testicle massage makes the balls sort of itch. They want more pressure once it starts. It’s kind of like having something large pressed into your ass, if you’ve ever had that happen. At first, it hurts, but then you get used to it, and not only does the pain go away, but you crave more and more. You want the object to be wider, and pressed in deeper.
Finally, it was starting to build into a dull ache, so it was time to move on.
She did the glans rubbing thing with the palm of her hand, and I was squirming with delight. I was too close to cumming, so I had to have her stop for a minute from time to time.
Thinking I might get chaffed if she went on with that too long, she decided that I had recovered from her first attempt at poking her finger into my peehole, so she repeated the alcohol and lube treatment, and reintroduced her finger. She pressed and twisted, and it did feel kind of like it was pinching, but I was loving it. Suddenly, pop, again, and I ejaculated. I couldn’t help it when I felt that pop.
The interesting part of this is that the cum couldn’t escape. I kept pumping and pumping, probably for nearly twice as long as an ordinary orgasm, and I could feel the pressure in my urethra. It was scary, but delightful! After I came, she left her finger in my urethra for a while, but after a few minutes, some sort of reaction was starting to happen inside me. I could feel an internal itch. I think my body wanted that cum to flow out, so I asked her to remove her finger. Ouch! It really stung coming out. When her finger came out, a bit of cum flowed out as well.
Even though peeing stung for the next three days, I really, really enjoyed the experiments with Monique!
The three of us got together one more time. That’s when I fully went to work on fisting Monique. Jerry kept interrupting saying, “You’re hurting her.” I wasn’t. She wasn’t flinching or anything. She told him, “Shut up, Jerry, it doesn’t hurt a bit.” It was Jerry that was flinching. The big guy is just too sensitive.
Finally, we got to a place, just short of actually getting my fist in, where she was starting to flinch and pull away, so I started to remove my hand. She asked me to keep pushing in, not come out, but I decided we’d leave it for now, which would only make the next time so much more fun.
As usual, Jerry came to soon. Again she wanted to see him get a handjob from a guy, with which I was only too happy to comply. But, again, he squirted his cum before the festivities had really begun. After that Monique and I played. I butt fucked her, which Jerry loved watching. Somehow, according to Monique, he didn’t mind seeing me butt fuck her, but he doesn’t want to do that himself.
I haven’t seen them since they moved out of town, but we stay in touch occasionally. Recently, I thought I’d drop them a fun little email.
I attached a picture I found showing two men with fully hard erections on the beach. they are laying back, side by side, looking at something apparently in the near distance.
Here’s what I wrote:
In my opinion, these guys are not gay – not that it matters. Don’t you two think it’s cool that two guys who are friends can hang out, show their arousal, perhaps at something or someone they’re currently looking at, or perhaps they are aroused because of something they’ve been discussing, or maybe, they just like to get hard when they’re outdoors and hanging with friends.
Wouldn’t it be great if in our society, that would be just the way it is? I think Jerry has a bit of that quality. That he is not afraid of what people think, and that, of course, is a good thing. I would love to get hard at a mixed gender nude beach, and just walk around letting everyone see my erected penis, and let them think what they may. They could believe that I’m gay, straight, whatever, and all is cool. And in my fantasy, they might start to participate with me. But I’m still way too shy for that in reality.
One day, a few years ago on Black’s Beach, the famous nude beach near San Diego, at a time when people simply didn’t show their arousal on the beach, I was just hanging out, along with a hundred other people. Most were just sitting or laying on their blankets on the sand. Most were white or Latino by the way.
One guy went briskly walking by. He was tall and very black. As he walked, he was casually stroking his dick, which was fully hard, and singing loudly. I wish I knew him, because I would have been proud to say he’s my friend. At least these days I would. At the time, I suppose I would have been embarrassed. What a shame!
On another occasion, I took a 19-year-old guy to the beach with me. He was a helper in my industrial refrigeration repair business. This was his first time at Black’s, and he was excited. When we got down the cliff and threw a blanket on the sand, he pulled off his shorts and was immediately hard. I told him that I was concerned people would get the wrong idea. (I was still afraid of being labeled ‘gay’ if you can believe that). I was also concerned because people didn’t just display hardons on the beach.
He somehow pretended not to hear, or understand me, and started lightly masturbating. He sat there for a half-hour and continued stroking himself lightly on the blanket, while I walked away. I went down the beach because I was actually afraid of being ‘with him.’
I came back, and he was still masturbating. There were now about six men and a woman standing around, and watching and chatting with him. Two of the men had developed their own erections as they were watching him. I mentioned to my young helper that it was time to get back up the cliff because we had an afternoon appointment. He jerked off harder and came right then and there.
I was shocked at the time. But, by God, what a chicken I was. Oh, how I wish I could have handled it differently. I would have jerked right off with him, and enjoyed all the company on the beach.
True story. Do you like it? See you two soon, Your friend! – Jeremy