I recently started remembering this after not thinking about it for many years. Not that I ever really forgot about it, but in a way I just didn’t dwell on it too much for a long time. Recently though something has happened in my life that has got me reflecting on my sexuality and I realize that what happened over at my friend’s house when I was a teenager probably had a big effect on me. Spoiler: it’s not really a happy story, even though I don’t myself feel particularly negatively affected by what happened.

This guy was my best friend, and I would frequently visit him at his house (which was only a few streets away), and slept over all the time. His mom, who was divorced, was a terrible cook, but other than that she seemed way “cooler” than my parents. She would let us do all sorts of stuff, e.g. ride our bikes in traffic, drink soda, watch anything we wanted on TV, or see R-rated movies, that my parents would never have permitted, and — being extremely well off as a result, I guess, of the divorce — they had all the latest stuff (for example, a computer, a VCR, etc. - this was a long time ago!) that we didn’t have. So naturally I went over as much as I could.

One thing that was very different at his place was that his mom (who was divorced), my friend, and his brother were very casual about being in various states of undress. This was strange to me - in our family, my parents wouldn’t have dreamt of emerging from their bedroom not fully dressed, and neither would I or my sister. However, “when in Rome” and all; I quickly got used to the idea that, when I was over at my friend’s, we’d often all be running around in just our underwear.

I don’t mean that everyone would automatically get undressed as soon as we walked in the door, but for example typically if I was sleeping over, we’d just put on underwear after taking baths in the evening rather than getting dressed again. Indeed, his mom would typically put our clothes in the laundry while we were in the bath, so I at least didn’t have any choice - the first time it happened I had to wear a towel - at least I quickly learned to bring a change of underwear. Then we’d sleep in our underwear (that habit, at least, I picked up and I ditched the PJs at home as well), and then the next day we’d all get up and hang out in our underwear for most of the morning, only getting dressed when we finally got organized to go out.

All this was really no big deal - I felt intensely embarrassed the first couple of times I stayed over (especially about the “towel incident”) but I quickly got used to it and didn’t think twice about it. I got used to other stuff too - for example, she she would point out, laughing, if one them randomly got a boner (obviously hard to hide in tighty-whities) - she didn’t do this to me that I recall, but it definitely felt weird that she was calling attention to my friend’s hard-on.

That was the sort of thing that would be studiously ignored in my family. However, without any real reference point, I just accepted it as normal for this family. I also was aware that this wasn’t unique. For example, my sister and I had a friend (whom we were both close to) who, when we went over to her house, would run around in just skimpy panties and encouraged us to as well. Her mom (come to think of it, also a divorcée) apparently saw nothing weird about this — two girls running around half-naked with a boy a couple years older! - although (unlike my friend’s mom) she mostly just ignored us entirely, whatever we were doing. The point is, so far as I knew, based on these two data points, it was our family that was weird about being dressed all the time.

My friend’s mom was also a very “touchy-feely” person - she’d often be hugging me, play-wrestling with my friend and his younger brother, and so on - again, this was something that initially embarrassed me (especially if she did it when we were all in underwear!) but that I got used to. Eventually I got to the point that I didn’t even worry about springing an erection, as sometimes happened, if she was horsing around with us - as I said she never called me out on that, even though she teased her own sons, so that probably helped.

The thing is, things kept escalating, really gradually, so that I never really reached a point where I said “this is too weird, stop it now.” For example, at some point she started encouraging me to take baths with my friend and his brother. They had a fairly big, luxurious bathtub and she made some joke about saving water (not that they would have had to worry about the water bill).

For my part I usually took showers at home, but the first time I’d stayed over my friend’s mom had run the water in the bath for me, and showed me how to turn on the jets - as I said it was a lot nicer tub than the grotty one we had at home! - so I was used to taking baths there. However, the brothers would take theirs together - apparently they always had - and neither seemed to think their mom’s suggestion that I join them was weird.

The first time, it was no big deal - all three of us piled in and, while it was a bit crowded, between the soap suds and the jets there wasn’t much to see and we just cleaned up, got out, got into our underwear, and went to watch TV. However, once I got used to that, she started come in to the bathroom while we were in the bath - ostensibly to help us wash our hair properly.

I can still remember the feeling of her massaging the shampoo in my scalp - it was kind of nice to be touched like that, honestly. I remember I had a hard-on under the suds but wasn’t too concerned about it. In fact I started to get kind of obliquely sexually excited by these baths on a regular basis, and look forward to them.

It was a liberating feeling to be completely naked and in close proximity to my friend and his brother, also naked, and not to be at all concerned about being seen that way by their mom; such a complete difference from our home, where we always pretended nakedness didn’t exist. But I have no doubt in my mind now that their mom enjoyed seeing all of us naked. She was just too eager to be in there with us while we were in the bath, and even encouraged us to move around in such a way that our nakedness would be more visible or that we’d “accidentally” touch.

To be fair, nothing seriously “naughty” ever happened in the bath, but there’d be a lot of slippery contact, whether accidental or on purpose (the tub was big, but not so big that all three of us could move around in it and never touch) and, naturally, we all got erections frequently, even in front of their mom. These weren’t usually commented on - erections when you’re all naked seem less of a joke than mere boners in your tighty-whities - but of course we were all looking at each other with undisguised interest.

Once it was just myself and my friend’s younger brother (I forget why my friend wasn’t in the bath) and we ended up getting hard and feeling each other’s genitals for a while. (Their mom wasn’t in the bathroom at the time.) My friend himself seemed less inclined to do this kind of thing - I remember I tried to touch him on a later occasion and he demurred - but after that incident I was always a bit interested in his brother’s body and used to fantasize about it, even though I was more interested in girls in general.

Anyway, baths, as I said, were a regular feature of staying over, and something I, honestly, came to look forward to. It was certainly more fun than showering alone at home. But then one night, a little later, for some reason, I was in fact taking a shower alone over there - I don’t remember why - and my friend’s mom came in and insisted on “making sure that I washed properly.” (I don’t think I ever failed to wash properly, but she was always intimating stuff like that.)

I remember I felt both a little ashamed (having her come in when I was in the shower alone felt a lot different from having her come in when all three of us were in the tub together) and also excited. I quickly got hard in spite of myself, and I remember I was trying to hide it behind my washcloth - a little pointlessly as obviously she had seen all of us with erections innumerable times, but this felt different somehow.

She simply took the washcloth out of my hand (I didn’t bother trying to hide myself at that point), soaped it up, and began to scrub me, starting with my chest. Honestly, I felt more embarrassment at being washed, as if I were a baby, than anything else. Up to now she had only ever shampooed my hair. But I yielded and obediently lifted my arms so she could scrub my pits when she prompted me to.

Then - she started on my butt crack. I kind of froze there; this was way beyond what I was prepared for. When she, inevitably, brought the washcloth around and started on my crotch, carefully working around my erection but liberally soaping up my pubes and, ultimately, reaching under my balls as well, I just let it happen, wordlessly, embarrassed in the extreme but also excited.

I don’t know what I thought would happen, but she didn’t actually touch my penis; she moved on to scrubbing my thighs and legs. I felt obliquely disappointed; at this point I wanted her to touch me more. As she was doing my legs she was kneeling down on the bathmat and I was looking directly down at her boobs (as usual, she was wearing just a bra and panties) and — oddly, for the first time — thinking of her in a sexual way.

It sounds paradoxical - you’d think as a horny teen seeing her half-naked all the time my imagination would already have been going wild — but seeing her in skimpy underwear was so ordinary by now that it didn’t even register. It’d been more the situations — running around in underwear ourselves, being naked in the bath, having her wash my hair, etc. — that had been exciting to me, not her body concretely, if that makes any sense. Now, as I stood there, rock hard, and she scrubbed my calves, I was trying to make out her nipples under the bra and imagining what she’d look like naked.

She eventually left me alone to rinse off. After I dried myself, I ordinarily would have simply pulled on my underwear and gone out, but this time for whatever reason my clothes were right there where I’d left them, not in the laundry and - not quite sure why I was doing it - I decided to put on only my shirt and nothing else. The shirt was pretty long and hung completely over my privates, but I was otherwise naked under there.

My erection had subsided for the time being but I still felt aroused and excited. I went out and sat on the couch, opposite to the one my friend and his mom were on. (My friend’s brother wasn’t there - I think he was at a sleepover.) I sat in such a way that, I was fairly confident, both of them would be able to see up my shirt a bit.

Neither made any comment - my friend was sitting there, in his underwear, with his mom cuddling on him. Honestly he looked a little fed up, like he didn’t want her touching him so closely. Eventually she started fake-bothering him, trying to get a smile out of him, and it soon progressed to the kind of roughhousing that she often initiated: tickling, play-wrestling, and so on.

He was giggling in spite of himself. But all of a sudden I couldn’t believe my eyes - or my ears. She had pulled down his underwear - on purpose or by accident, it wasn’t immediately clear, but then she said something I almost assumed I had misheard: “Oh, you have such a cute penis!”

There was no way she could have said that to her son, could she have? I could rationalize everything else that had happened in this weird household, even having my private parts washed in the shower, but this was just - wrong, wasn’t it? But yet, there they were. My friend’s underwear was half-pulled down, and as far as I could see he was, if not fully erect, at least stiffening. And his mom was holding him semi-pinned and definitely looking.

I felt a kind of ringing in my ears. I was hard myself, anticipating - I didn’t know what, but something was obviously going on. However, nothing further really happened. After a while, she let up a little, and my friend casually pulled up his underwear, leaving me to wonder if I’d totally misunderstood what happened. I felt a kind of obscure disappointment; almost wondering why she hadn’t commented on my penis.

And actually, as I reflected on it later, maybe it wasn’t that strange - I mean, it was strange, sure, but this was a women who would regularly tease her sons about getting boners in their underwear. Was it that weird that she would pull down my friend’s underwear while play-wrestling, then say he had a cute penis? Well, yes, it was weird, no question, but ... well, if any of this had happened the first time I slept over, I probably would have run home screaming, but I’d gotten used to a lot of weirdness over the years I’d been going over there. I kind of filed it away, and in fact nothing else like that happened for a while, but then...

As background - my friend’s bedroom had two beds at right angles to each other - when I slept over, I always slept in one, with the head ends together so we could talk. Over the years we’d often had “interesting” conversations, talked about sex and girls and the like. I had tried to persuade him to masturbate with me, or engage in other kinds of sex play, but while he never reacted particularly negatively, he hadn’t shown any real interest either. I had jerked off in the room with him, and I’m sure he heard me, but I’d never heard him do the same - perhaps he didn’t, or perhaps he was just quiet about it.

As I said, I was mostly interested in girls, but I did feel some sexual interest in some of my male friends. I was more attracted to my friend’s brother (especially after he’d initiated touching my privates in the bath that time), but these days he was rarely around, and after the “cute penis” incident I kind of became weirdly obsessed with trying to see what was so cute about it. Of course I’d seen it many times, soft and hard, mostly in the bath, but this was a bit different. I remember suggesting that we both sleep naked, but nothing came of that.

Anyway, about a month later, I went over and my friend’s room was going to be repainted - the workers had already come and put plastic over everything. It occurred to me that we wouldn’t be able to sleep in his room. I was assuming we’d just have to sleep in his brother’s room, and I remember being a little excited in anticipation of that - maybe I could get him interested in masturbating together.

It wasn’t to be, though. When it came time to go to bed, as natural as could be, his mom indicated that we’d both be sleeping in her bed. Yes, with her. At this point nothing really surprised me anymore. I wasn’t even all that excited - just mentally prepared for anything to happen, I guess.

We brushed our teeth and I got into the bed first - for some reason I really wanted to be on the side with the door. (No, I wasn’t afraid and expecting to flee - no idea why I was thinking that way.) Despite my equanimity I couldn’t help but be taken aback when my friend’s mom entered the room from the bathroom - stark naked. She’d taken off her bra and panties and, for the first time, I was seeing her completely nude.

She had fairly big breasts and thick pubic hair, pretty much exactly what I’d imagined she’d look like (her underwear had never left that much to the imagination). Casually, as if this were an everyday thing, she just got under the covers next to me, and patted the bed to invite my friend to get in on her other side. She asked me to turn out the lamp, on the table next to me, and I did. And that was that - she seemed to expect us just all to go to sleep, so I did my best. I was aroused, frustrated, and uncertain as to what I should do about it, obviously unable to just pull my underwear down and masturbate as I would have liked to.

I must have dozed off a bit, but in the middle of the night I awoke with an almost tangible jolt. I could hear fast breathing. It was definitely my friend. At first I thought - he must be jerking off. But his mom was turned towards him, and even in the darkness I could make out that her arm was moving. There could be no doubt about it: she was masturbating him.

I had no idea what to make of this observation. Obviously this was far beyond anything I’d ever imagined would actually happen, regardless of all the weirdness that had led up to it. It was exciting to for me to be in bed with a naked woman but even my wildest fantasies would have involved her deciding to have sex with me in the middle of the night and my friend just ... not being in the picture. Not that I would wake up and hear her jerking him off.

But there was no doubt about it - that was what was happening. I could hear my friend letting out little moans. His mom was silent but was clearly doing this intentionally - this wasn’t happening in her sleep or something. I wanted to join in on the “fun” somehow, but as I lay there, frozen, with a raging erection, I was completely unsure of what my role was supposed to be in something like this.

Finally, after what seemed like an eternity, I started to move, surreptitiously, towards her backside. At a certain point our feet made contact and she didn’t even seem to notice. Emboldened, I put my left hand on her waist, trying to pretend as if it were a complete accident, an involuntary movement made in my sleep.