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Create Your Own Story

Hi Folks! Jeremy and I would love to hear your stories. Please write a story in the comment area below, or you can send direct to me using jenelle@sex270.com.

You do not need to identify yourself but you can if you wish. Your story can be a true memoir, how-to information, fiction, or whatever you want. It would be great if you could let us know whether it’s true or fiction, however. It can be from any perspective.

The length can be anything from a sentence to a complete ebook.

If you’d like to include video or pictures, that would be great. Email them to Jeremy.

Please don’t send any copyrighted material unless you are the owner.

We can’t pay anything for your submissions, and do not guarantee to publish every one, but we’ll do our best to publish anything that’s of reasonable quality.

Swinger Memoir

I’ve been involved in swinger activities for a number of years. When my wife and I first started, it was with a like-minded neighbor couple. We used to get together with this other couple frequently and socialize. Despite being very close friends, the subject of trading wives had never come up.

But one evening we were visiting at their house and we all had a bit too much to drink and it just happened. I had gone into the kitchen to freshen my drink and when I came back to the living room, my wife was sucking Larry’s cock. My initial reaction was a fit of rage but as I saw her lips caressing his throbbing penis I got strangely turned on. Melissa, Larry’s wife, called to me and I walked over to her, unable to take my eyes off of my wife Sandy’s bobbing head. As I continued to stare, Melissa unzipped my pants and pulled out my hardening penis. She peeled back my foreskin and sucked the head into her mouth.

Before the night was over I had fucked Melissa twice and although my attention was diverted from what Larry and Sandy were doing, I’m pretty sure he shagged her at least three times. She told me later that he had even fucked her in the ass, something I had never done with her.

The funny thing about the whole experience was that after the last cum, all four of us lay naked on the bed together and talked about how much fun we’d all had. No recriminations and no hard feelings. Even as we lay there and talked, Sandy continued to fondle Larry’s now limp penis and I gently stroked Melissa’s wet clit.

This was the beginning of our swinger life. We managed to get together with Larry and Melissa a couple of times a week. It was always the four of us together. There was something about sharing the experience that really made it enjoyable. I’ve never been able to fully understand it but it gave me great joy to see Larry’s erect prick slamming into Sandy’s wet cunt. As our meetings progressed I learned how much fun it was to suck another man’s cock while the two women lapped each other’s pussies. One of my favorite things to do was to literally pull Larry’s cock out of my wife’s pussy and suck her juices off of it. Larry had a really nice cock and when he got hard it was like a bar of steel. I grew to love his dick as much as I loved his wife’s sopping wet cunt. And he sucked mine with equal enthusiasm.

Our love of swinging sex with Larry and Melissa led us to wonder what it would be like to broaden our experience. Larry had learned about a swinger club that operated in our town. It was in a very large, but old mansion. Two lesbian women owned the house and held swinger parties there about every third week. It was by invitation only and no singles allowed. I never did know exactly how Larry got us an invite but he did.

There was a fee to attend but the house supplied condoms and lube as well as snacks and drink mix. Plus clean linen on the beds. If you wanted the hard stuff you had to bring your own. Fresh, clean white towels were in abundance for clean-up purposes and there was always a need for clean-up. By the end of an evening at the club, a generous amount of cum and pussy juice had been secreted.

The house rules stated that men had to be totally naked. Sandals were supplied for your feet. Women were allowed to wear teddies or a loose cover up but after the first hour or two pretty much everybody there was naked. I suspect that the invitations were limited to a certain age group. My estimate is the age of the members ranged from about 30 to 45. And everybody was quite fit. Other rules were you were free to invite anyone to have sex with you but “no” meant “no.” Anybody who was overly pushy was asked to leave, never to return. I only saw one couple ejected and surprisingly it wasn’t the guy who broke the rule but it was his wife who constantly pestered one of the male members who had politely refused her advances on numerous occasions.

On our first few visits Sandy and I had kept our sexual activities limited to Larry and Melissa. But at one point, an extremely good looking guy, with a very impressive erect penis, had approached Sandy. I could tell she was immediately interested. She looked at me with a question in her eyes and I slightly nodded.

The house layout had two main large rooms that had originally had been the living and dining rooms. It also had a large number of bedrooms. Although the large rooms were more of a communal meeting area, some sex occurred there. I’ll be honest, I was totally shocked when Sandy and the new guy, who I later learned was named Rex, wasted no time whatsoever. They sat down together on a couch and within minutes she was sucking his large dick and that quickly led to her laying back while Rex shoved his dick in her pussy. She had her legs up over his shoulders and he pounded away with a real frenzy. They ended up spending the entire evening together going off into various rooms. She told me after we got home that he had fucked her five times and she sucked him off twice more. She admitted it was the best sex she’d ever had.

Now you would think I would be upset hearing that. But truthfully, I was just happy for her. As we had sex with more and more different partners, we both learned that it made us happy when our significant other had a great experience. Sandy and Rex fucked on a fairly regular basis but slowly the novelty wore off and she tried out other partners. I had a few women who I was partial to and they were to me, and we regularly had sex together. Sometimes just the two of us and sometimes with a third or fourth partner, usually including my wife and/or Larry and Melissa.

There was a surprising amount of male to male and female to female sex that occurred. In my younger days I had always assumed that same sex action occurred only between gays but my eyes were opened to the fact that almost every person there was bi-sexual. They just enjoyed sex and it didn’t matter what the partner’s gender might be. Then one thing occurred that I thought I would never do. Sandy and I were in a foursome with another couple. They were a bit younger than we were. She was very cute with a perfect body. The guy was in great shape but had a relatively small penis. Probably about 5-1/2” long and slim. Actually that is about the average penis length but I had noticed that as a group, most of the club members had larger than average cocks.

Anyway, I was fucking his wife Marie in the missionary position while Sandy sucked his dick. I wasn’t paying too much attention to them when I felt fingers wiping some lube on my asshole. Before I totally realized what was happening, John was penetrating my ass with his hard cock. It slid right in and although I had always said I would never let anybody fuck me in the ass, it actually felt really good. My wife knew of my aversion to being ass-fucked and was getting quite a kick out of me having a dick up my ass. I learned later that she put him up to it. She figured with his small size that it wouldn’t be that difficult to penetrate my ass.

I have to be honest, the sensation of my hard cock pumping Marie’s tight pussy while John thrusted his cock in and out of my rectum was almost more pleasurable than anyone had a right to expect. It wasn’t that long before I felt John’s cream spurting in my asshole and that triggered my orgasm and I flooded her cunt with a major cum load. Then as John pulled his cum covered cock out of me, Sandy grabbed his dick and sucked it clean while Marie did the same thing to me.

After we got home that’s all we could talk about. We relived the experience over and over. I sucked her clit to several orgasms and she coaxed another one out of me with her expert oral action. That led to a few days later her ordering a strap-on online. The cock on the strap-on was bigger than John’s and it took a bit of getting used to by me as it was initially a bit painful. I never understood what a woman gets out of using a strap-on but she said it gave her a feeling of power and that she usually had an orgasm. She had become extremely orgasmic as our sex experiences expanded, so I didn’t doubt that fucking me could make her cum.

She took the stupid thing to the club and she talked both Larry and Rex into letting her fuck their ass as well as several other willing club members. There was one guy in particular who really got off on her fucking his ass. He would get on all fours as she knelt behind him and fucked away. You could see his big hard dick dangling down and after ten minutes or so of her banging away, huge streams of jism would spurt from his dick. This became the talk of the club and it got to where they would do it in one of the main rooms with many members grouped around watching. The guy admitted to Sandy that her strap-on gave him the best orgasms of his life. Any time we were at the club and he showed up, he would beg her to fuck his ass. And she would. I told her she should start charging him a fee.

There was one gal who I was particularly taken with. She was probably the youngest woman there and was only 23 or 24. Her husband was older. Maybe 35. She had a very athletic body which I find especially attractive and a terrific set of real tits without any sag at all. She had a beautiful face and of course was in great demand but she was very particular about who she had sex with. Fortunately I was one she liked. Sandy used to tease the hell out of me about Gina preferring me over some of the studs that were members. Gina and her husband didn’t come regularly, maybe every other couple of months. But when she was there she always looked me up and I was only too happy to oblige. But the odd thing was, her husband did not want her to fuck anybody. Only blowjobs or handjobs. She preferred blowjobs. In fact she once told me she would rather suck a dick than fuck one. I don’t know if that was true or if she was just sticking to the party line.

No matter. Whatever the truth was, the girl sure loved to suck a cock. She gave, without a doubt, the best blowjobs I’ve ever had. It’s hard to describe exactly what she did that made her blowjobs so good. Part of it was she literally worshipped my cock the whole time she was licking and sucking it. To her, it was like my cock was the only thing that existed in the world. She would pull her lips off of it and then stare at my dick like it was the most wonderful thing in existence. She was also adept at deep throat. I’m only about 7-inches so it wasn’t a major feat to deep throat me but the frosting on the cake was as she took my entire length, her tongue would flick out and lick my balls.

On several of the times when she sucked me off, Sandy would be there just watching. Not participating in any way because she didn’t want to be a distraction. But she was hoping to learn what this girl’s secret was because I had raved about the quality of her blowjobs. And it paid off. Sandy became the second best cocksucker in the world. She never fully approached Gina’s competence level but came close enough to make me happy. Even Larry commented about how great her blowjobs had become.

I know it’s probably hard for some of you to believe, but our swinging lifestyle has really cemented our relationship. I love Sandy with all my heart but there’s nothing wrong with mind-blowing sex with other partners. Feeling those spurts of cum go down some stranger’s throat or vagina makes living really worthwhile.

That’s it for now.

My Sister’s Friend’s Anus

My sister's friends' anus

I thought I knew a lot about most things, as 18-year-olds will do, but I didn’t have a full grasp on sex yet. I met one of my sister’s friends, and found her immensely attractive. She was slim and short, like 4’10,” with long black hair. Somehow, we struck up a conversation that turned into a mutual liking. Boldly, I suggested we go for a walk.

She asked where. I replied that there was an unmanaged park a couple blocks away. It was a place of cool, dark forested trails. Just the thing for a hot summer day. So, I drove her over there, and we started walking around.

There was no one in sight. I tried to steer the conversation to sexual matters, and she more-or-less went along with it. I put my hand on her shoulder, and she didn’t object. Just that little bit of touch excited me.

Thinking maybe I could get a little luckier, I moved my hand to her lower back. Very lower back. Still, no objection. Meanwhile, I brought the conversation around to masturbation. She admitted that she did it, but didn’t volunteer any specific information.

My fingers slipped under the waistband of her shorts and panties. Fortunately, they were elastic, so soon, my hand was on the round globe of the right side of her ass. She didn’t say whether she liked it or not, but I took it as affirmative, since she didn’t ask me to stop. I was super-excited to feel her pretty, small, smooth round ass in my hand.

Here’s where I got really crazy: I moved my hand over her ass crack, and as we continued walking, and I could feel the muscles of her butt working with each step, I slowly worked my forefinger between her ass cheeks. Still no objection.

I pressed my finger directly against her anus. Still no objection. Instead, she uttered, very quietly, “Hmmm, nice.”

It took a while because we had no lubrication, but I managed to work my finger gently into her asshole about an inch. Mind you, we were still walking. Weird, eh?

All this was because I was such a nerd at that age, that I didn’t know a more elegant way to do things.

I so wanted to stop, lay her down in the soft late summer leaves, and fuck her big-time, but didn’t know how to steer the conversation. If that wasn’t going to happen, at least maybe there was a way I could see and feel her vagina. Maybe I could show her my super-stiff penis, still trapped in my shorts, and she’d want to play with it. Some variation of this seemed inevitable.

We continued walking and conversing. I kept trying to bring the conversation back to sex, but it kept veering back to other, more general things. The walking and finger-in-the-ass thing was getting awkward, so I removed it, taking a moment surreptitiously to inspect and smell it. The finger seemed perfectly clean, but smelled out-of-this-world beautiful!

Our walk came to an end, and nothing more happened. We said our goodbyes. I was convinced this was the first girl I would fuck. I was sure she’d become my girlfriend. It never happened. I saw her a few times, but she was always with my sister. Somehow I was too shy to ask her on a date. Then my sister went back to college, and that was that. I never saw the lovely young girl again.

My Brother Laramy

I’ve always been interested in all things sexual. It started before I can remember, but by the time I was fifteen not only was I masturbating at least twice a day, but I was always on the internet, looking for new information about sex.

I had figured out early on that I didn’t want to fuck. Too problematic in many ways. For three years after opportunities started coming my way (pun intended), I was still technically a virgin. However, in my early years, I had all sorts of objects stuck in any place they can be stuck, by both guys and girls. And, of course, I’ve been not only the stuckee, but the stucker, also.

But back to when I was fifteen. I had read that some women can orgasm from anal stimulation. I had already experienced clitoral and vaginal orgasms – plenty of them. All by myself, however. I hadn’t yet done anything with anyone else. It almost happened with this girl I know, but she geeked out at the last moment, so we didn’t even kiss.

The more I thought about the idea of orgasming from anal stimulation, the more I knew I had to try it. Oh, I had pressed a finger into my own butt, and sometimes an object or two. While enjoyable, nothing brought me close to orgasming. I started to realize I needed someone to help me out. I just couldn’t get it right by myself. But who?

The idea of my 13-year old brother came to mine. He’s a lovely kid, and would do any reasonable thing I asked. but no. Too crazy, right?

Well, you know how it is. An idea builds in your mind, and like a bulldog with a bone, you won’t let it go. So, feeling all sheepish and silly, and hell, downright embarrassed, I asked him.

“You want me to do what? You’ve gotta be kidding,” he ejaculated – in the old-fashioned use of the word. He was a late developer. I was pretty sure he couldn’t ejaculate yet, in the more modern use of the word.

I’m sure my face turned red. Now I felt like an idiot asking him to finger my ass.

Then he surprised me by saying in a bright, enthusiastic voice, “You bet!”

We got naked. It wasn’t like we hadn’t seen each other naked before, but that was like 8 years ago, when I was seven and he was five.

I was so horned up already, but then seeing him, with hairless little boner all hard and sticking straight out, well, I orgasmed, and I hadn’t even touched myself. It’s a good thing I’m a multi-orgasmic girl. From what I had read, not all women are like me. Some cum once, then like the boys I’d read about, they are totally done.

Now Laramy, my brother announced, “I can cum, you wanna see?” as he immediately started stroking his penis.

“Wait,” I practically yelled. I knew if he came he might lose interest in doing anything with me. I explained why I wanted him to wait, and he stopped. But he didn’t stop looking at my breasts. He was just staring, almost drooling like a fool. I was rather proud of my boobs, even though I was hoping they hadn’t fully grown in yet. They hadn’t reached that stage where they fold over and lay against my chest. I didn’t know if they would ever get that big or not. At the moment, they were really just bumps with little pink nipples on them.

On that occasion, Laramy did indeed cum, but it was like two little clear drips that seemed like water, or clear piss. I put my finger on one of the drips on his tummy, and it was kind of sticky, so I guess it was truly cum.

That was the first of many sexual explorations. He and I eventually became quite oral. There’s nothing like a dick in your mouth from a guy that you really and truly trust. Then, when that guy turns around and licks your clit, sucking your inner labia into his mouth, well, call it “Heaven!” We sometimes did 69, sucking each other at the same time, but more often, we’d take turns so we could more fully get the experience.

Around age seventeen, I met a guy named Ken. He and I hit it off. It wasn’t long before we were sexual. Oh, I know, but look, we were careful, always using condoms. As I’m sure all adult women know, the fulfilling feeling of a penis in your cunt can’t be beat, right?

The only problem with Ken was that Laramy became sort of jealous. Well, not quite that. He just missed our sessions together. Fortunately for Lar, that didn’t last long. One day Ken mentioned an interest in bisexuality. It took me like one second to figure I should set up something with Ken, Laramy, and me.

Fast forward ten years. My breasts never grew bigger. Oh, they’re OK, but they don’t flop down like I think I would have enjoyed. I’m still with Ken. Can you believe it? Laramy, Ken and I did fully play several times. A couple of times, in front of Ken’s delighted eyes, I did actually get fucked by my brother. Even in the ass one time. Always with condoms of course.

However, it didn’t last. It was inevitable that Lar would meet a girl. In fact. He’s been a serial monogamist for the past several years, but has totally lost interest in playing with Ken and his sister. Oh, well. Ken and I know how to have a good time with each other, and some other people we’ve met. But all that’s for another story.

Mrs. Sanderson’s Prostate Massages

Mrs. Sanderson's Prostate Massages

I’m assuming this story, told to me by a client is true. Knowing the guy, I suspect it is. Here you go:

So, as you know, I was diagnosed with benign prostate enlargement. It’s typical for a man of my advancing age, and harmless enough, as long as one takes care of it. Let it go, and you get to where you can’t pee with a forceful stream like you should. I was supposed to get some physical exercise a few times a day for fifteen minutes each time, avoid sitting for long periods, eat healthy, and one other thing.

The doctor asked whether I would like prostate massage, then explained what it is. I’m fortunate to have a gold insurance plan, which covers such things with only a tiny co-pay. In this case, $10.

So here’s the deal. The doctor’s office set me up with weekly appointments with a Mrs. Sanderson. She’s a massage therapist. She is trained in several modalities and seems very professional, if perhaps a bit on the spiritual side. Like, she’s into astrology, and uses Indian terms, such as ‘lingam’ to mean ‘penis.’

Anyway, I went to her. She draped me except for the necessary portions of my lower body. Then she placed a gloved finger in my rectum, and pressed all around for quite a while. What an interesting feeling! You feel sort of like you’re going to pee, but you don’t and it’s actually much nicer. I’d love to get this treatment even if I didn’t have BPE.

So, the first time was great. I felt like I was starting to get an erection, but laying face down on the table, it didn’t much matter. I figured she couldn’t see anything.

The next time, she asked whether I felt a need for being draped.

I boldly said “No,” and for some reason, being entirely naked in front of this woman felt very erotic. It didn’t make any sense. She’s older than I am, gray haired, and quite overweight. But friendly. I did get an erection, and there’s little doubt she saw it. You’d think I’d be embarrassed about it, but I quickly told myself it must happen with many of her clients, and so my embarrassment turned to a weird sort of pride. She said nothing about it, and neither did I. It was a bit strange, however, to have an erection, to be sexually aroused, and not have an orgasm. I wanked big-time when I got home.

Oddly, I did ejaculate a bit during Mrs. Sanderson’s session. Well, not really. The prostate massage causes a bit of semen to work it’s way down the urethra and show up at the tip of the penis.

The next appointment was the same. Erection with no one reacting to it.

The fourth appointment, Mrs. Sanderson asked whether I’d feel more comfortable with a release.

I had to think about it for approximately 1/2 second. “Yes, of course!”

After the finger in the butt thing, she removed her glove, put on some massage oil, and gave me an expert handjob. I mean really expert. Somehow, she was able to read my physiology, and know when I was close to squirting. She kept me on the brink of ejaculating for two or three whole minutes. Finally, I squirted quite a bit of cum all over her hand and my belly. It resulted in a big smile from her, and from me.

I have been going to this woman for over a year now, and of all damn things, my prostate has returned to nearly normal size. The doctor is amazed. He says none of his other patients have made as much progress. I attribute it to good diet, the exercising several times a day as he recommended, and of course Mrs. Sanderson’s treatments. Her handjobs have been so good that sometimes she can keep me in actual orgasm, contractions and everything, without squirting any cum for minutes at a time. Finally, she purposely takes me beyond orgasm into ejaculation. Amazing!

My wife knows all about it, and is surprisingly fine about it. I’d think she’d be all crazy, or jealous, or at least I thought she’d say “You’ve gone too far this time.”

But no, she claims to be relieved because I’m not so ‘demanding’ of sex with her. I don’t actually demand it, but that’s the way she feels about it. Since menopause, many years ago, now, she has been much less interested in sex than I. It used to be the other way around. Oh well, Mrs. Sanderson fills the gap nicely.

Oddly, those handjobs of her’s are better than actual sex. Go figure!

36-Inch Flexible Dildo

36-inch dildo pressed into friend's anus

I have a friend that I play with from time to time. We usually just jerk each other off, but he does like anal play – a lot. I on the other hand, am not much into anal at all. Or, I should say I don’t like things stuck in me. But I do enjoy sticking things in my wife, and in my occasional male friends.

Usually, he likes ordinary dildos and things a few inches long. We have also experimented with fisting, and on a couple of occasions, I have gotten my whole hand into his rectum. He wants me to go farther, but I find he has a restriction about ten inches (25cm) in that I cannot get past.

One day, he showed me his new 36-inch (90cm) flexible rubber dildo. To give you some perspective, a typical man’s pants are only 31 inches in length.

He wanted me to put that in him. I was skeptical, and worried about physical injury. Still, he wanted it.

Se I lubed him and his dildo and went to work. He laid on his back with his knees up, and I started pushing it in. At about a third of the way, it was going nicely. At two-thirds, he had me stop a couple of times. He said it didn’t hurt, but he had to get used to the feeling. I resumed. It seemed stuck. I pulled back a little bit, then pushed forward again. It continued to enter him. There’s no doubt it was well into his transverse colon.

We kept playing, and finally, I was holding the last two inches (5cm). All the rest was in his large intestine.

He couldn’t see what I was doing, so he asked, and I told him how far it was in. That excited him. His penis, which had been semi-hard the whole time became like a flagpole. He wanted me to push in further. All the way in. I thought that was irresponsible. Like, what if he couldn’t push it back out? Something short in the rectum can be pushed out, but that long? I had my doubts. But I was willing to go another inch. I believe the far end was right up against his appendix, because that last inch was impossible.

He said he wasn’t feeling any pain, but his physiology told me otherwise. He was kind of wincing. So, ever so slowly, I pulled the whole thing out. As I was doing so, he rubbed his own penis to a fantastic orgasm.

In fairness to you, dear reader, I should point out that a year later this fellow was hospitalized for a serious intestinal problem having to do with an overzealous enema. So, it turns out there are limits to sexual play that should be regarded. Over the years, I have found many ways to have fantastic orgasms without taking any health risks.

Juggling Club

Male solo-sexual play with a juggling club

I had recently taken up the sport of juggling and bought a set of three juggling clubs. These things were about 20 inches long, made from thick but hollow plastic, with a spherical knob at the end about an inch in diameter.

For the longest time, I wondered if one could be popped into an ass. My ass, specifically.

So one, cold winter night, when it was nice and warm inside, and my roommate was gone for the night, I had to play. It was my one-time fetish. I had been building up to trying this for a long time.

I got naked. Just having the run of the basement apartment with no clothes on was a rare treat. I became erect immediately.

I looked around the apartment, and the only lubricant I could find was Vaseline. It would have to do.

Standing in the living room, I coated the knob of a juggling club with Vaseline. For good measure, I stuck my greasy finger an inch into my ass and rubbed the Vaseline around in there also.

Then, it was time to get to work. I touched the knob end of the club to my anus. It was deliciously cold. My penis, already erect, got even harder. I pressed a little bit, but it wasn’t going in. At least not easily.

Realizing that the standing position may not be the best way to accomplish my task, I went to my bedroom, and laid face down on the bed. Again, I pressed the knob against my anus. I pressed quite hard, but it wasn’t going in. Oh, well, I was prepared to give up, and just jerk off to a nice orgasm.

As I started to get off the bed, I realized that if I would place the juggling club on the floor, then sit down slowly and carefully, it might just go in. So I did that, and I felt my anus slowly slipping open. What an interesting feeling! Then, almost with a pop, the club slipped fully in. I should have enjoyed it, but instead, it kind of scared me. So, I tried to pull the club out. It was quite firmly being held in by my anal sphincter. It took me over a minute to relax enough, and finally, with a bit of a pooping force, I was able to extract the club. That action felt nice.

My ass wasn’t hurting or anything, so I decided to stick the club back in. This time, it went in more easily, although I still enjoyed the very wide feeling of my anus as the knob slipped through. Oddly, my eyes felt like they were opening very widely at the same time.

I noticed the club could just hang there. That was exciting. I started walking around the apartment with the bulk of the juggling club hanging out my ass, like a tail. I walked around some more, just enjoying the feeling as the club swayed and bounced back and forth, slightly rotating and pulling the knob within my butt.

Without warning, that ‘gonna-cum’ feeling overtook me, and I ejaculated immediately, and I hadn’t even touched my dick. Quite a bit of cum spilled on the carpet. I got some toilet paper to wipe it up, with the club still trapped in my rectum. It turns out you can’t use toilet paper to wipe up carpet. It breaks into little pieces. So, I walked to the kitchen, with the club still hanging out of me, and found some paper towels.

Finally, the mess on the carpet was cleaned. I noticed my penis had stayed hard, and the club still felt nice in my butt. But I was also starting to sting just a little bit. Reluctantly, I pulled it out. As I cleaned the knob with a paper towel, I was surprised to find how warm it had become. 98.6, just like me.

After cleaning, the club still smelled. Not like poop, but a sweeter anal secretion smell, much like a girl’s anus. I had to clean the club more thoroughly before the odor went away.

Meanwhile, I was getting horny all over again. After putting the club away, I jerked off to my second ejaculation of the day, before falling asleep naked and happy in my bed.

I’ve never done that since, but have found many other interesting masturbatory pursuits.

Ickiest Thing

The ickiest thing: fisting another man's butt

I was recently asked about what was the ickiest sexual thing I have done.

I once put my whole hand in another man’s butt.

He was a friend. We had jerked each other off several times. He’d ask for anal fisting now and then, and I’d always decline. He kept practically begging, and finally, I caved.

He put some very viscous fluid in his microwave to warm it. He said it was some sort of veterinary liquid. It was clear, had no odor, and was very thick and slippery.

He got on all fours while I coated a finger in the slippery goo. I slowly introduced my finger into his anus. That wasn’t so bad. I’ve joyously put my finger in many female and male asses in my time. I’ve always enjoyed the tight feeling around my finger, especially when they are orgasming.

I pulled it out slowly, and went in with two fingers. I massaged his prostate gland for a while, which he was loving. A few drops of semen dripped out of his erect penis. I’ve learned this is natural. From compressing the prostate, where semen is stored, it will naturally be expelled.

My penis was also erect, but I ignored it.

I withdrew the two fingers, and put in three – ever so slowly. That went well, so I put in four. His anus was becoming relaxed.

Now was the time to go for the big event. I coating my whole hand with goo. Then, just in case we were successful, I also coated my lower arm half way to my elbow.

Slowly, very slowly, I pressed and twisted, and soon all five fingers were within him. He had me stop for a while to get used to it. When he was ready, I pushed and twisted some more, and felt his anus expanding to take my whole hand. Finally, I made it all the way in. He was in heaven. I just held still for a bit, then decided to go exploring. I pushed in farther, which was easy now, since the bulk of my hand was past his sphincter. I found a constriction about ten inches in that curved off to one side. I believe this is where the rectum meets the large intestine. He was wincing and going ‘ouch’ now and then, but he wanted me to push on. Finally, I was about 12 inches in with my fingers worked in around the curve, and as far as I could go. Or at least as far as I could safely go, in my opinion. I was worried that I could actually burst or damage his colon.

We had seen videos where you see a man on all fours like my friend was, but the other man’s arm is buried inside almost to the shoulder. In other videos, you’ll see a man on his back, and you can watch a bump move around within his stomach area, pressing upward against the abdominal wall, all the way up to the rib cage.

We weren’t able to accomplish that. I was happy with my 12 inches. In fact, I pulled back out a little bit so I could do some exploring. I figured I might be able to feel his kidneys, stomach, spleen and liver from within there. I imagined doing this to a woman, and finding and gently massaging her ovaries. Would that be as delicious for her as testicle massage is for us guys? I was thinking how fun it would be to get my fingers around his bladder and give it a little squeeze. I’ll bet that would be interesting if it had some fluid in it. But the definition of what I could feel inside him wasn’t very good. It was all just squishy feeling, except for his backbone.

After a while, he expressed doneness, so I very slowly removed my hand. It was difficult for him to expand enough for me to get the widest part of my hand back out, but of course we managed it. I figure anything that goes in can come out.

I went into his bathroom expecting the worst. I figured I’d be covered in poop. But no, I was clean as a whistle except for the goo on my hand and arm. However, that stuff wasn’t particularly water-soluble, so it took forever to wash it off. BTW, I should mention too, that there was never any odor. It seems my friend had given himself an enema before my arrival, for which I was very thankful.

In conclusion, while anal fisting isn’t something I’d want done to me, and I’m not particularly a fan of doing it, it made my friend very happy. I did stay erect the whole time, so I must have enjoyed it more than I’ll admit. He and I jerked each other off afterward.

Shortly after that day, I moved out of town, so we never repeated the experience. I’m not sure I would have if he had asked.

I believe this practice is highly dangerous. I present this account only for your amusement, and strongly caution you not to try it yourself. I actually met a guy who had undergone a colostomy from giving himself a high-pressure enema, so accidents, horrible accidents, can happen. I’m not sure how strong the rectum and large intestine are, but since there are so many other and fun ways to have fun and give yourself orgasms, I recommend those instead.

Clueless

In my lifetime so far, I have run into a few clueless, oblivious, or just plain stupid people or sexual situations.

I was dating a beautiful woman. I knew it might be pushing beyond her boundaries, but I asked her whether she’d like to go to the nude beach with me. To my delight, she accepted. However, there was one condition: She wanted her two brothers to come along. I figured a chance to see her nude would be worth it, even with those encumbrances.

The weather was perfect. We got to the beach and stripped off all our clothes. I was very happy to see her naked, and have her see me. I guess I’m a bit of both a voyeur and an exhibitionist. I kind of liked the idea of being naked with the guys, too. Her older brother turned out to be a nice and interesting guy. The younger brother was a bit slow in the head. I think maybe he had something like autism, although he was fairly chatty. What was rather amazing about the kid is he sported an erection almost the whole time we were there. Everyone ignored his erection, and a good time was had by all.

For a short time, I dated a woman who turned out to be more of a nymphomaniac than I could handle. For instance, she’d knock on my door at 11pm wanting sex, even though I had told her earlier in the day I needed time to myself. We’d fuck, then she’d wake me up again at 3am wanting more. It was just too much!

One time at a restaurant with this woman, she started trying to unbutton my pants under the table. The tablecloth may have partially obscured the view, but I wasn’t so sure. I pushed her hand away, and a minute later she tried again. I scowled and said I didn’t want that. Still, she continued to try to unbutton me, ostensibly to give me a handjob, like five more times.

I was in the YMCA shower. It was the older style, open shower room. No stalls. It also didn’t have doors. Instead, there was a wall and another wall arranged in such a way that coming from the gym or the pool, you could walk right in, but no one could see inside. It was not soundproof. Just the opposite, as the quietest voices would echo off the tile walls. I was the only one there at the time except for a child about 11 or 12 years old. I could see by the look of his face that he was off in some way. Maybe Mongolism or mental retardation. He just came out and asked, “Does it feel nice when you touch your penis?” I don’t remember what I said if anything, but you can bet I grabbed my towel and got out of there right away.

I found another girlfriend who was more balanced than the nympho. I had a friend who knew my girlfriend was visiting. Her car was in the driveway, and there’s no way he didn’t notice. It was a good neighborhood so I left door unlocked. It was around 10pm. He just came right in as we were both naked on top of the bed. She was on her hands and knees, and I was fucking her from behind hard and long, but making sure not to cum too soon. He sat on the edge of the bed and started a conversation about politics just as if we were clothed and having tea. He didn’t make any move to participate in our activity or anything else. He just kept on talking.

She and I didn’t quite know how to react. My penis started to soften, but to her credit, she wanted to keep going. Soon I was fully erect again as Keith kept talking. She and I had a simultaneous orgasm. I’m sure it helped her that I had a finger in her ass. I think it also was helpful to have him watching. He was looking right at it, yet he didn’t say a thing about what had just happened. He just kept going on about Republicans and Democrats.

When I was working as a general welder, I would sometimes hire a kid to fetch and carry. It was better than arranging clamps to have him just hold things in position while they were being tacked. He was fine kid but his thinking was kind of slow.

One day after work, I invited him to the nude beach. He had not been to a nude beach before, and was excited. I explained that when people get to the end of the trail at the bottom of the cliffs, they take off their clothes and enjoy the sun. This was the more conservative kind of nude beach where nothing of a sexual nature takes place.

As we were walking down the trail, he removed his shirt then his shorts. He was nude half-way down. People just didn’t do that there. I was embarrassed, but didn’t say anything. When we hit the bottom, he spread his towel right away, and started slowly jerking off. His penis was fully erect. I explained to him that it wasn’t proper etiquette. He surely heard my words, but didn’t change what he was doing in the least. I was so embarrassed, I walked away and headed up the beach. In retrospect, that was inappropriate of me, but hey, I was young.

When I returned, he was still masturbating right there in front of everyone. The funny thing is, there were around 6 men and two women standing around him, admiring what he was doing, and holding on a conversation as he continued to wank.

In my late teens, I had a jack-off buddy. This was in a time when masturbation was pretty much never discussed, and considered bad news in much of society. One day, while standing in front of a store with a lot of people standing around, he quietly asked whether I’d like to get off with him later that day. No one could hear him, but as he said it, he made the universal sign of forming his fingers in the shape of holding his penis, and moving his hand back and forth in front of his crotch. I don’t think he was aware of his gesture.

I had a friend who loved everything anal, but he was willing to do the things I liked also, such as practicing multiple dry orgasms, post-orgasm stimulation, and glans blame (rubbing the oiled palm of a hand over the tip of the penis). The poor fellow had no limits. He wanted me to fist him, which I did reluctantly. It should have geeked me out, but actually, I found it quite intriguing to have my hand that deep inside another person. I tried to feel and identify his internal organs. I figured I might be able to feel his kidneys, his bladder, maybe even his stomach. But all I could make out was his backbone.

On another occasion he had a 36″ (92 cm) soft dildo which he had me insert all the way except the last inch. The thing must have gone most of the way to his appendix. He loved butt plugs, enemas, everything to do with his butt. Then one day, I heard he was in the hospital. It seems he had given himself such an enema that he burst his colon and needed surgery.

I had a girlfriend who I asked to tie me down and do whatever she’d like. I had assumed this might be things like testicle massage, tickling, or an edging handjob. First she crawled all over my body and kissed me extensively. I rather enjoyed that. But then, she had this notion that somehow I’d like her to open a little box of cockroaches she had collected, and set them loose all over my body.

I went to a convention. In the hotel on the first evening, I had nothing to do and was thinking about sounding, the act of inserting something in my peehole. Looking around the room, I found a ballpoint pen with a long tapered end. That would make a nice sound, but what to use for lube? The only thing there was a packet of shampoo. OK, I figured, that’ll be sufficiently slippery.

I coated the pen with the shampoo, and stuck it about 4 inches (10 cm) into my dick. It started to sting, so I removed it. It turns out shampoo and urethras don’t get along well together. The sting continued to build and build. It got so bad that the next morning, when I tried to pee, it took twenty minutes, letting out one little, but extremely painful squirt at a time. It took three days before I could walk fully upright again. The pain was just that bad. I told people at the convention I had hurt my back.

Back in the days when one could hook up with people on Craigslist, I encountered a guy who was willing to offer exactly what I wanted at the time. I was really intrigued by glans blame. For those who don’t know, when done right, it really makes a guy squirm. Then after a few minutes, the feeling changes, and a guy might feel like he’s going to pee or cum, simultaneously. In most cases, he doesn’t urinate or ejaculate, but sometimes one does let out some pee involuntarily.

So this guy started rubbing my glans, and although he was a bit too intense for my taste, it was wonderful. Then, while he was still doing that, I ejaculated. But he didn’t stop. It was terrible, excruciating, exciting, actually quite wonderful. I squirmed and tried to get away, but he just kept going. It started to sting. Finally he quit. For the next few days, there was a scab on the end of my cock, because he had worn right through the skin. It healed without a trace within a week.

When I was around 13 years old, I was into photography. This is in the days when serious photographers had a darkroom to develop their own film and make prints. I knew in my adolescent brain, that ‘real’ photographers do nudes. After all, there were always artistic nudes in Popular Photography Magazine. Not knowing any willing girls at the time, and I think not even noticing that the pictures in the magazine were all female, I asked a 13-year-old fiend to pose. He took off his clothes, and I took a bunch of pictures. When my dad came home from work that evening, he saw the negatives hanging up to dry. I got a pretty good lecture about what’s what in the sexual world, including, ‘keep my hands off boys.’ As you can tell, that lesson never completely sank in.

Those are a few of the clueless situations I’ve encountered. Leave a comment below telling us about what clueless sexual things you’ve seen, heard, or done.

Girl Likes to Show Asshole

I’ll admit I’m a little weird. But, I’m not hurting anyone, and everyone has fun, so why not, right?

It started when I was really young, playing doctor with my brother. I got a rather excited kick out it, especially when he’d have me get on all fours and ‘examine’ my asshole.

Then in school, we had a sex education day. For the most part, it was pretty ridiculuous, with a somewhat embarrassed teacher telling us boring stuff we already knew, and a whole class of kids tittering and carrying on. The only good part was where we all got bananas and condoms, and had to practice putting them on. The teacher then handed out a second condom to each kid, both the girls and the boys, and told them they were ours to keep, and use if needed. How weird is that?

The teacher said one little thing that I found particularly interesting. I doubt it affected the other kids in the same way. She said the girls should get hand mirrors to look at their vaginas, and both girls and boys could use hand mirrors to become familiar with their own anuses.

Oddly, I was greatly affected by that. When I got home, I couldn’t wait to grab my mother’s mirror, get naked in my room, and look at my asshole. I didn’t care that much about my pussy – I don’t know why, but really wanted to see my asshole. And when I saw it, I went nuts. Well not entirely. It just struck a chord in me, and I masturbated something silly, giving myself two orgasms in a row. That’s the first time I ever had two like that. I didn’t even know it was possible.

So now, the image of my anus was permanently front and center in my mind. I decided to take it step further. Although it was difficult to get the angle right, I took a picture of my ass on my phone. Over the next several days, I studied that picture over and over, for minutes at a time.

I started to want others to see my butthole. It took a few days to figure out what to do. I tried it on my brother first. When my parents and sister were out, I knocked on his door and asked, “Hey Kyle, I’m worried about something.”

“Yeah, what?” he asked, evidently annoyed.

“Well…” I hadn’t expected it to be so hard to ask. I decided it was now or never. “I don’t think my anus looks quite right. Will you take a look?”

“What’s wrong with it?”

Oops, I hadn’t thought that far ahead. What should I tell him? I couldn’t hesitate long, or he might know something was up. Finally, I got an idea. “It itches.”

“Why bother me with that? Go ask Mom or Dad.” he replied, but his voice was oddly squeaky.

“I can’t. Too embarrassing. Remember when we used to play doctor, like a hundred years ago? Well, you’ve already seen it, so what’s the big deal?”

“Oh alright, pull your pants down.” he said a little too quickly.

I did just that, and with them bunched around my ankles, I hobbled over to his rolling office chair, facing away from him. I felt him touch my ass with both hands, and gently pull my cheeks apart. That alone, was absolutely amazing. What a feeling! And the cool little puff of a breeze from his air conditioner suddenly blowing against my anus – to die for!

“I can’t see anything. Here, why don’t you take your shorts off, and get on your hands and knees on my bed.”

Without a word, I complied. I didn’t trust my voice. It would have come out all shaky.

He got behind me, and looked and looked. I was in heaven!

Finally, he said, “I don’t see anything wrong. You say it itches?”

“Um, yeah.”

“Let me know if this itches.” and with that, he started ever so gently rubbing his finger around my anus. Oh my god! Then, he started pressing his fingertip right into the middle. Just a little bit, but that was enough for me. I was orgasming. I don’t think he noticed, or if he did, he didn’t say anything.

“I guess not,” was all I stupidly said. For some reason, I was suddenly embarrassed. I grabbed my undies and shorts, put them back on, thanked him, and left his room. I heard him setting the lock on his door behind me. I didn’t realize it then, but he must have masturbated as soon as I left.

Next, I wanted my mother to look. I told her it itched. She said, “Put some cream on it,” and that was that. I couldn’t work the conversation around to asking her to actually take a look without seeming too weird.

OK, so there was my father. I told him my anus itched. He said that was something to bring to my mother, and went back to reading his tablet.

Now who? It took me days to realize I could ask Becky, my best friend. Why I didn’t think of her right off the bat, I don’t know. I found her sexy in a way. Goofy I know, but I’m just telling the unvarnished truth here. But how to bring it up? How in the world could I get Becky to look at my asshole? Oh my god, just thinking of her looking at it had me wanking away in my bedroom.

I realized what I had to do. I just had to come out with the itchy ploy, and hope for the best. What’s the worst she could do?

She could call me a ‘perv.’ She could tell a teacher, or her parents! Bad idea. My heart jumped into my throat.

A few days later, my horniness overcame me. We were in my bedroom. I squirmed around on the edge of my bed, hoping to make it look like I was dealing with an itchy butt. She fell for it. “What’s up with all that squirming?”

“My butt itches.” – OK, I came right out with it. My heart started racing. What was she going to do?

Well, what she did was totally unexpected. “Maybe I should take a look.”

I couldn’t believe I was hearing that. She offered! I pretended to be all embarrassed and shy, because I didn’t want her to think I was weird, but I went a little too far with the pretense. She said, “OK, then,” and left me hanging there, butt-unseen. I was so disappointed. If only I had not pretended to be shy to quite that degree.

We returned to our homework, or so I thought. While I was doing a math thing on my tablet, she was doing something on hers. She turned to me, holding up the tablet, and showed me a full-screen picture of a slightly hairy anus! Hanging below the anus, was a pair of testicles. She said, “Does yours look like this?”

Bang! Instant horniness! Thinking quickly, I answered, “Not quite like that. But I wonder if I have a rash or something?”

“So, you want me to look after all?”

“Yeah, I guess so,” I said, feigning moderate indifference.

A minute later, my school skirt and panties were off. I was laying on the bed, and my best friend Becky was spreading my ass cheeks and looking at my anus. Heaven!

You could have knocked me over with a feather with what she said next. “Mmm, it smells nice.”

I know I shouldn’t have, but I was thinking with my ovaries, not my brain when I answered, “I wonder if yours smells like that?”

About five minutes later a fly on the wall would have seen two naked girls, hugging, kissing, and rolling around on my bed. We explored not only our anuses in great detail that day, but our pussies, too. It turns out that as excited as I am by showing my anus, Becky just loves having her peehole seen. That’s right. She wanted me to spread her slippery inner labia and look at her peehole. Who knew?

On another occasion, we experimented with me looking at her peehole while she tried to let out a single drop of urine. To our amusement, that didn’t work out too well. She splashed me right in the face with a big squirt. It took us several practice sessions before she could let out a single drop of pee. But it’s something we had to learn, right?

One time, we got in the bathtub. I was on all fours, and she was sort of half-standing over me. She peed right on my anus. Taking it a step further, I tried to kind of hold it open so she could pee inside. We managed to do that a little bit. It turns out to be difficult to relax your asshole enough that you can hold it open. That’s especially true if you’re in a bathtub, reaching around to your own butt. It hurts your knees.

The rest of high school was quite a bit different than the beginning. That’s because for my next trick, I started ‘accidentally’ showing pictures of my anus on my cellphone. I’d let people see pictures of my dog, my house, or something like that, and either they’d scroll and find the next picture was my naked butt, or I’d scroll and go “Oops!” faking great embarrassment. This opened great conversations that almost always led to fooling around.

It was more boys than girls, although I enjoyed both. Some of the boys wanted to fuck, but I managed to keep it to just showing my ass, or maybe giving them a handjob until my first days of college.

I rather liked giving handjobs. One day, this guy, Juan, invited me to his house after school. It was a short walk. He assured me both his parents work. His older brothers were out working, so the house would be empty. I knew Juan fairly well from school, but I was still nervous. One hears stories about being alone with guys.

He was a perfect gentleman. We went through the actions of me showing him my butt, and I was all set to give him a handjob. I was even considering giving him a blowjob, something I had never done, but instead he instructed me to lay on the bed. He started rubbing my anus very lightly, as if he knew exactly what I wanted. He spit on his finger, and pressed it part way into my anus. I felt an orgasm coming on, but he pulled his finger back out.

He excused himself, and came back with a bottle of alcohol, and a tube of something. He coated his finger in alcohol, then put some cream on all the fingers of his right hand. Instructing me to roll over, he placed a finger against my labia. I wasn’t sure I wanted that. After all, I’m an anus freak, right? But his finger actually felt rather nice. I didn’t say anything. He kept just lightly touching my labia. Soon, his fingertip was entering my virgin pussy, and soon after that, there were two fingers all the way in there as I was orgasming over and over.

I don’t know where he learned it, but he was curling his fingers around and rubbing what I later came to know as my G-spot. Oh my, oh my! It was the best feeling in my life. But he wasn’t done. While he was doing that, he snuck the index finger of his left hand under my butt, and penetrated my ass all the way with that. Orgasm City!

Juan and I became an item until we went off to separate colleges. In college, my horizons have expanded. First, I learned all about intercourse. Fucking is great! However, for me it always has to start off by the guy looking at my asshole. I don’t know why, but I’m not going to fight it. I still really love people seeing that. I have also experienced anal intercourse, Oh, it’s lots of fun, no doubt, but still, when I can get a guy, or a girl, to just look in between my spread butt cheeks, and just study my asshole, I’m in heaven.


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