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Strange Approach to Lesbianism

Piano teacher, strange approach to lesbianism

I’ve been taking piano lessons from Helen forever. Well, actually, ten years, since I was eight years old. I want to be like her someday. Helen earns a nice living at $60/hour teaching kids, and adults.

I already have some students. I love a genre called ‘Roadhouse Boogie,’ but can also play and teach jazz and classical. In fact, I like most types of music. But what I really enjoy is imparting a can-do attitude on my students that comes with learning music. I also like the interaction. One gets to know one’s students, and it’s almost like having a large and wonderful family.

Helen is like a mother to me. She kind of looks like a 30-something version Meg Ryan, with shortish, curly dark blond hair, a thin body, a very thin neck, and rather large boobs.

Me, I’m Hawaiian, through and through, although people who don’t know any better have mistaken me for Korean, Japanese, Sumoan, even Chinese, if you can believe it. I keep my shiny black hair really long. I can almost sit on it.

Even though I’m already a pretty good pianist, I still take lessons from Helen. These days, the lessons are more about business coaching in the world of teaching piano.

I find Helen rather attractive, and I have a feeling she kind of likes me. I mean, to see her eyes sparkle when she looks at me sometimes. Well, I like that. I never thought of myself as lesbian or anything. Yet, dare I admit, I have masturbated with her in my mind at times.

We’ve talked about everything. She knows about my family situation, and I know hers.

So, it wasn’t too much of a personal stretch the other day when I brought up my little problem. For the past couple of months, I’ve been constipated.

She just came out and told me I have to eat less junk food, especially sugary things. She said I have to cultivate an enjoyment of salad. I didn’t really want to hear that, and I’m sure she knew, because she then rocked back on her piano bench the way she does, looked me right in the eye, and then… hesitated.

“OK,” she said, “I don’t know whether I should tell you this…”

“What?”

“Well, uh… I read an account recently about a man who claimed to his girlfriend-to-be that a finger pressed into the anus brings temporary relief from constipation.”

I don’t know why, but I found just hearing that terribly embarrassing. Was I embarrassed for her, having brought up such an intimate thought? Or, was I embarrassed for me for some reason?

The discussion soon turned back to business, and that was that.

However, the thought rattled around in my head for a few days. The idea of Helen sticking a finger in my ass brought instant chills to me, and I had to go in the bathroom and give myself an orgasm more than once.

At our next meeting, Helen asked whether I was eating better, and how my constipation was coming along. I had to admit that I was still hooked on eating cereal in the morning, sandwiches for lunch, and so on. I was still constipated. However, the line of questioning caused shivers in me, and I couldn’t resist asking, “Hey Helen, can you tell me more about the finger in the anus thing?”

“Does that sound like something that might be useful?”

“Actually, maybe… yes, yes I think it might be helpful.”

“Would you like me to help you with that?”

Oh, my god! As soon as she asked, my heart leapt into my throat and started beating a hundred miles an hour. I’m sure I blushed big-time.

“Um…”

I realized I couldn’t even complete a sentence. Couldn’t even work out the thought. I would love to experience such a thing, but dare I admit it?

Realizing I had paused for a long time, I rushed to form a complete sentence. “I suppose it might be worth a try.”

Then editing myself out of some sort of worry that I had said something really bad, and at the same time not wanting to kill a possibility that this could really happen, I added, “I mean, this constipation is really quite annoying, and well, maybe, well, I think it might be… yes… a good thing, I think.”

Unfortunately, Helen had students all day. She invited me to return to her house at six that evening. I can tell you, I was full of springs all day. I could hardly think straight. It just seemed like forever for 6pm to roll along.

Finally, there I was in her living room. She said, “Let’s go through to my bedroom. I think we’ll be more comfortable there.”

Once in her room, after a long and uncomfortable hesitation, Helen said, “OK, let’s just do this. No fanfare is necessary. Why don’t you take off your clothes?”

“All of them?”

“Well, you could just pull down your knickers, but that seems kind of inelegant, don’t you think?”

After some more hesitation and awkward small talk, I found myself fully naked in Helen’s presence. I also found myself shivering, although it was actually warm in her bedroom. Helen, meanwhile, was fully clothed.

I was kind of embarrassed about my small breasts, and the fact that I keep my pussy hairless. I also didn’t want to seem too eager, for some crazy reason. And yet…

“You know…” I began, with my voice actually shaky, “I’d be more comfortable if wasn’t the only naked person here,” and I tried to laugh.

“Ah, I understand. Furthermore I was hoping you’d ask.”

At this point, I knew we were BOTH too far gone to turn back. We had both essentially admitted to each other that we’d like to do what it was obvious that we were going to do.

Helen stripped, and I have to say, that woman has the most beautiful breasts I have ever seen. Very white, full, heavy, hanging down against her chest, with big nipples, Oh my! She turned at one point, and her ass was to die for. I guess I find white people very attractive, or at least Helen sure was.

I found myself face down on Helen’s bed. She had me spread my legs wide so she’d have access to my asshole. Evidently, she had prepared for this, because she had some coconut oil, which she spread on her finger. I felt the gentlest and slightly cold touch against my anus itself. The very center of my being in my opinion. My, did that feel great! If nothing else had happened, I’d have a memory to masturbate to for years to come.

But much more did happen. True to her word, Helen worked her finger deep, really deep, into my rectum, and it felt so good that I was wetting her bed with the juices flowing from my vagina. I orgasmed. I tried, mostly unsuccessfully to suppress a moan.

Helen laughed good-naturedly. “Was that an orgasm?”

“I’m afraid so,” I squeaked out as I was coming down from the sexual high.

“Do you want more?” Helen asked, even though she didn’t wait for an answer. That delicious finger of hers started pushing in and out only about 1/4-inch. I was so sexually high at that point, I couldn’t even speak. I was just like, “Ummmm, ohhhh.”

“I hope this isn’t too intimate,” she said, and with that, she managed to place another finger in my very wet and slippery pussy. Orgasm city!

I had, never in my life had more than one orgasm at a time. This was the first occasion where it was just orgasm after orgasm.

When things finally died down, she withdrew her fingers very slowly. The one in my ass seemed super-long as it kept coming out for what seemed a very long time.

I rolled over on the bed to face Helen. She climbed on top of me, embracing me in the best hug of my life, and then she started kissing me.

Who knew? I mean, up until then, I had the occasional random thoughts of a sexual nature with Helen, but men had been in my sex fantasies also.

As the weeks went by, Helen and I played often. It’s true that eating better cures constipation. Or maybe it was the repeated butt-fingering. I did the same for her, even though she wasn’t constipated. I did much more for her too. She taught me how to really be a woman, with all it’s sexual context.

At first, I worried about this lesbian ‘thing’ quite a bit. I couldn’t even bring myself to say the word ‘lesbian.’ I watched a couple of Netflix movies involving homosexual women, and didn’t really care for them. But in time, I came first to reconcile being lesbian, and then to embrace it. A year later, I was a major LGBT advocate.

I was scared to death when I finally came out to my parents. It was needless. My dad just went, “Hmpf,” the way he does when he learns something that doesn’t particularly interest him. My mother was more verbose saying that both of them knew for quite some time that I’d probably be interested in girls. Evidently, they were totally fine with it.

Just last week on my birthday, Helen had a huge surprise for me. Her brother was at her house. I had met him before. He’s a big, strapping police officer.

With the two of them smiling at me in a certain way, and the way they were carrying on, it was soon obvious to me what they were planning. More than once I had told Helen that I wondered what it would be like fucking a guy. She had tried to give me the effect with a hairbrush handle, and then a soft dildo she bought on Ebay, but I kind of wanted to experience the real thing.

That evening I lost my virginity. On the one hand, I was rather intimidated by his massiveness, his hairy body. On the other hand, I have to say, having your vagina, your body, spread wide and filled with a penis is a super fulfilling feeling. Helen sat there rubbing herself to orgasms as she watched me and her brother getting it on. I love Helen!

I’m a Nudist Nonbinary Man

I'm a nudist nonbinary man and I masturbate

I’ve never felt like I was fully a man. There was no doubt about it
physically and I was always interested in my body and in masturbation. But
while I loved women, I never had that desperate need that so many men have;
in fact, I was seldom able to perform adequately with a woman, no matter how
much I loved her. And while I’ve always had a strong feminine side, and
have dressed essentially androgynously (jeans, shorts, t-shirts/tank tops,
sandals, and I love wearing short men’s skirts), that was the extent of it.

Complicating this was serious PTSD from being sexually abused at a very
young age by my grandfather. I’ve slowly recovered vague memories of him
having me be his “naked slave”, a pattern of behavior that resurfaced after
the divorce from my first wife, and which I adopted completely – the idea
that because I could not perform with women I had to become a slave to the
Goddess and serve her through naked service to women. There’s nothing wrong
with that if it’s sincere. The article “Slave Michael” here on
Sex270.com is about my life when I was seeing myself as a slave.

Then I caught Covid, which was mild, followed by long Covid, which laid me
low. I was bedridden for weeks, with a slow recovery to follow. It
affected my brain and my thinking, and as I came back to life I realized
that the PTSD and slavery had vanished. While I still love to be and be
seen naked, the urge to submit myself to a subservient relationship was
gone.

While I was sick I got acquainted with current thinking about gender
identity, and soon realized that, in modern terms, I am nonbinary. I
strongly identify physically as male, but sexually I’m female. This is why
my sexual relations were not successful – I was supposed to be the one
getting fucked. I realized I had lost all interest in having sex with
women. Like most men, I’ve experimented with anal sex and liked it OK.
Alright, more than OK when it came to wearing a butt plug and the few
occasions when a woman used a dildo on me. But the thought of being fucked
by a man was anathema to me. I obtained a dildo which is almost exactly like
my own penis but two inches longer, and using it on myself turned out to be a
delight, so much so that I began collecting photos of attractive penises from
the Internet, having prints made of the best ones, and fantasizing about them
being used on me.


Oddly enough, though, I still have absolutely no actual
sexual interest in other men – I just want to be fucked by a beautiful penis.
It was a revelation to find that there was very little actually sexual about
being fucked, but I love not only how it feels but also the idea of having
to allow my body to be penetrated and used for someone else’s pleasure, for
as long as he wants to. But the pandemic, and then monkeypox, make it all
too obvious that it’s way too risky to be meeting people I don’t know well
and allowing them to use my body these days.

Michael, nonbinary nudist

I’ve lived for years as a smooth (shaved) nudist full time at home, and
sometimes when visiting friends. My useless-for-sexual-relations genitals
are not just visible all the time, the lack of pubic hair puts them on
display. It’s impossible for me to ignore them. The realization that they
can only be used for masturbation now has freed me to see them in a
different light: that’s what they’re for, and there’s no shame or guilt in
it, any more than using my legs to walk around, because it’s no longer about
sex in the traditional sense. I don’t do it because I feel deprived or
sneaky, I do it because it brings me pure, unadulterated joy. And honestly,
is there anything more beautiful than a big erection?

Things I think about when I masturbate:

* Having my anus exposed and available all the time

* Going out in a skirt and getting fucked

* Having friends who come to my house and fuck me sometimes

* The first time I get fucked being videoed and posted online

* Living as a roommate with a man, on the condition that I live naked all the time and he can fuck me

* There are lots of photos on the Internet, most on Wikimedia, of me naked that get lots of views and that I can’t take down, and I think about people looking at those and seeing me the way I actually live.

* People seeing my naked pictures on the Internet and thinking about me getting fucked

* Also people looking at pictures of my bare feet on the Internet

* Always being naked and shaved with my genitals on display

* Everyone knowing my genitals will never again be used for sex with another

person, and that they are only for viewing and masturbation

* People reading this article

I don’t masturbate with the goal of ejaculating, quite the opposite. I’m a
tantric edger, getting high on sexual energy, and prolonging the high for as
long as possible. In that respect, masturbation is sacred, since tanra is
one of the seven yogas, on a par with the hatha yoga practiced by many.
There is a spiritual element to the high that elevates the spirit and lasts
afterwards. In the interest of keeping the plumbing healthy, I do
occasionally cum, and it’s a rare treat when I do.

Nonbinary Michael masturbating

Sometimes I will take yohimbe, an herb which acts a lot like Viagra, and
spend hours enjoying the extended state of arousal. It also makes my body
look sexier to me, especially being shaved. I wish I could feel like that
all the time, but the herb has side effects that make it impractical for me
to use it too often. The new freedom I feel about masturbating means
promoting and dedicating time to it no longer carries any stigma. After
all, how is it any worse a thing to do than to self-indulge watching
football and drinking beer all day? And I wind up feeling fulfilled, not
drunk.

I should add that I never masturbate around others unless it’s part of the
context of a situation. Similarly, if a visitor is not comfortable with
nudity, I wear clothes in their presence. I get no pleasure from someone
else’s discomfort. I do often regret that necessity, since it’s all about
pleasure and joy, but members of this society are conditioned from early in
life to be ashamed of their bodies, and to fear being in the presence of
nudity. I would love for masturbation to be widely viewed as I view it, a
personal activity that’s good for physical and mental health, and not one
more thing to feel inhibited and guilty about. Maybe someday we’ll get
there.


Create Your Own Story

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Swinger Memoir

by Spurtz

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.

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