The Massage Night

This story is about one my earliest and most unusual sexual encounters. I've changed the names, and some of the details—but hey, this is a story. It may not be exactly how it happened, but it's how it should have happened, and it probably conveys the feeling of the experience better than a more literal rendition.

My name is Steve. I was a young graduate student in a northern university town, living in a housing co-op with about 30 other people not far from campus. Many of the other residents were undergraduate students, though there were a fair number of working class people as well. It was a pretty liberal setting, with shared food and cleaning responsibilities, monthly meetings where all residents shared in house governance. Several members were openly homosexual, which may have been more significant in the late 80's than it would be today. The house was also "clothing optional," and had co-ed shower facilities and a sauna. Which takes us to our story....

Kay and Helen, two undergrads in the house, had been good friends ever since I had arrived in the summer. Kay, a dark-haired Japanese girl, had a fairly bold and flirty manner about her, while Helen, a short-haired blonde, was a little more shy, though she had often caught my eye. I was even more shy though, and didn't make any serious attempt to date within the house, or outside of it for that matter.

I think nothing more would have happened except that later in the Fall, Kay met someone outside the house—John—that she wanted to invite over for some playful exploration. I don't know exactly how it all started, but I'm guessing she felt more comfortable doing a group activity that may or may not turn sexual rather than just be with him by herself, and so asked Helen to join, and asked her to invite another male to round things out with. However it was decided, the girls came to my room early in the evening and asked if I wanted to join them with John for some time in the sauna and some massaging later. We had done a group massage with several other people in the house the previous month, strictly non-sexual, so this wasn't completely unusual, though this time it was just the four of us.

When John arrived at the door, the four of us went to the sauna, and quickly undressed. John was just slightly taller than me, and struck me as more confident and outgoing. Both girls were significantly shorter than us, and quite thin, especially Helen, and both had relatively small breasts. John and Kay immediately seemed like a natural fit. It's harder to say if Helen and I were, and we surely would never have hit it off it we hadn't been encouraged by the other pair, but we were definitely more comfortable with each others' hesitancies than with a more bold and aggressive partner.

In the sauna we made light conversation, sharing our thoughts about school, our living quarters, and people we knew. A few shoulder rubs were given, but there was no intimate touching, and we simply grew comfortable in the presence of all these naked strangers. The girls and I hadn't seen each other entirely nude before except perhaps briefly going in or out of a shower, but we were all nonchalant about it. We were there quite a while before deciding to step outside into the brisk air. John and Kay immediately took a run around the house, which was not so risky as you might think as we were at the end of a cul-de-sac, but still Helen and I demurred both from shyness and the cold, and stood naked on the porch until they returned. We then carried our clothes up to Helen's room for some massage.

Kay took charge of preparing our massage setting, and soon she had laid out a number of towels on a futon and the bed, and a bowl of hot water keeping warm a container of peanut oil. The men first began to massage the girls; I joined Kay on the bed while John treated Helen on the futon. I was definitely too cautious in my ministrations, I didn't know what was expected or what would be tolerated, so I stayed away from any sensitive areas and didn't get very sensual in my massage. At one point Kay even turned over on her back and her legs opened wider as if inviting me to leave no body area untouched, but I politely and doubtless very timorously stuck to her legs. Believe me, if I had the sexual experience and confidence than that I have now, the evening would have gone much differently! But I'm trying to convey what it was really like, and back then I know wasn't thrown out as a milksop only because the other participants weren't all that far ahead of me. John I'm sure was willing to do more, but Helen may not have been so inviting and he kept his ministrations to non-intimate areas, though I think he may have pushed and fondled those a little more vigorously and sensually than I did, enjoying the contact with Helen's lithe body.

But Kay and John did start upping the talk at a certain point, relating past sexual experiences and desires. Homosexuality was brought up, and while everyone was quite straight, Kay made the intriguing comment that she totally identified with gay men, because for her, sexuality was about "getting poked," and she fully appreciated men enjoy passive anal sex. She added that one good thing about anal sex was avoiding any risk of pregnancy. Without explicitly saying that she had done and enjoyed this act, the hint was pretty direct. John in turn related a party he had been at where a woman offered to service several men one at a time in a private room, and that the others later accused him of having anal sex with her, though he too never explicitly said if he had had done it on that occasion or any other. This again raised the level of permission, as we talked about possibilities of acts without explicitly raising the idea of actually engaging in them. I don't actually know what Helen's sexual experience was, but I would guess it was not much more than mine, which amount to a few short and conventional encounters with one woman in college just a couple of years back.

Neither Helen nor I contributed much to this talk, except to express general approval of alternative sexualities, and disappointment that anyone would tease someone for a choice of sexual activity, whether real or imputed. But I'll admit I was inwardly surprised by Kay's blunt talk, as too many years of feminist and PC-influenced classes made me think that it was wrong to see women's sexuality as shaped by men. To openly admit that penetration in whatever form was the name of her game seemed counter to what I had come to expect about women's sexual desires, and to what I thought was expected about how I was to treat women's sexuality. Yet I was excited by this frank admission, as much by its unexpectedness as by its particular subject; I got the sense that sexuality was more complex and startling than I had hitherto imagined.

At a certain point we did take turns, and the girls massaged us. But they too kept to pretty standard areas during this time. I'm sure we were all wondering though, were we going to turn to sex, and if so of what kind? Would we have an orgy, or just pair off separately? All the elements were there—hot oil, soft mattresses, naked bodies. But nothing explicit was said or proposed for a while.

Eventually we switched partners and assembled on the futon. This was a little small for all four of us, but slightly more convenient as we all access the peanut oil without moving. Kay and Helen lay face down on while John and I resumed rubbing their backs. We sat on the side at first, but Kay quickly suggested that we could apply more force if we sat on top of our partners. This predictably led to some leg bumping between John and I. Physical contact with another naked man was not exactly what I had in mind in this increasingly intimate moment, though again this is one of those things I look back upon in laughter. It wasn't that I was homophobic, but I was simply unused to the complexities of sexuality, and had after all had very little contact with women even at that point. Today this seems ridiculously trivial, but back then it was a major step to accept John's hairy leg rubbing against mine, without making myself even more uncomfortable by trying to pull it away, which really wasn't possible because there was so little room between the two girls. In any case, my inner reluctance over this strange contact with another man was quickly overcome by the prospect of resting my thighs upon Helen's soft white buttocks, and seeing John adopt the same position. Our still-flaccid penises stuck out slightly across our respective partners' lower backs, and we soon took in the great enjoyment of the broader contact between our bodies and those of the girls.

At some point Kay and Helen started holding hands, and turned their heads to look at each other. I'm not saying they were gazing into each others' eyes, in fact I think they both, Helen in particular, made a point of often looking away, sometimes back towards us or at a wall, but there were also many moments when they did look at each other and talk softly, which perhaps was more to communicate a sense of comfort and unity through their tone than through what was said. While John and I could easily hear what they said, it was also clear when they were just talking to each other and not to us, which made me feel like a less than relevant bystander. There was no hint of a sexual attraction between them, yet it made me reflect upon differences in sexual expectations. Of course, they had been friends for months, so it was no shock that they were more comfortable with each other's bodies than John and I, who had just met. Yet I also perceived this as an indication of how homophobia, or fear of being mistaken about one's sexual identity, was much more of an issue between men than with women. Kay and Helen could easily take each other's hands in an intimate situation like this to express comfort and solidarity more than John and I possibly could have, and this made me feel a little bit alone and isolated. Which in turn struck me as strange because here I was, sitting on a naked 19-year old and rubbing her lower back, at her implicit invitation; how could I feel isolated in the midst of such physical proximity and intimacy? Yet obviously some of us were more intimate than others within this lovers' square, and physical and emotional connection were two different things. I knew this in principle, but it was startling to experience it so vividly. I had a lot to learn.

From here on I largely took John's lead. Some sidelong glances and a few neutral words between us were actually quite comforting in helping me both relax about our proximity, treating it as nothing unusual, and to be more daring in my massage. I tried not to imitate him mechanically, but our parallel positions permitted me to model his movements, and especially his confidence in them, more strongly. As he started to massage Kay's upper buttocks, she moaned with pleasure, and I soon did the same to Helen, who also enjoyed attention to this less-frequently touched area. John and I slid back slightly to expose and then rub the girls' butts more fully. You have to imagine how delightful this felt, as we were all pretty well covered in peanut oil by then, so as our thighs slid down the backs of the girls' legs, and our penises picked up more oil along the way as they dragged along the outer cracks of butt cheeks and thighs, we were enjoying the sensations and sights at least as much as the girls were enjoying our touches.

At some point John and Kay went further; she verbally commended the touches she liked best, and he took the invitation to explore further, which led him to reach his hands across her entire butt cheek, inside with his thumbs and index finger as well as the outside with the rest of his hand. He moved more slowly and gently as he began to rub her anus, which she said felt very good. A few words between the girls on the experience gave me the impression that Helen was open to the same treatment, at least to follow Kay's lead, and so for the first time in my life I glided my fingers across a woman's asshole. Her legs were tightly closed, but with her cheeks slightly spread I could see a few curls of pubic hair and the lowest edge of her vulva underneath; of course I had seen her from the front earlier that evening, but not so close, so this too was a new intimacy.

"God that feels good" said Kay, as she started pulling her legs upwards, and as John lifted his own to one side she rearranged herself in a doggie-style crouch, butt sticking far back at John, who stood directly behind her on his knees. He poured a few more drops of peanut oil on his fingers and resumed rubbing her asshole. She commented to Helen on how the position aided in access to the source of good feelings, which elicited only the neutral comment, "yeah?" but then in a moment Helen did the same so I too was faced with her exposed butt, and wider access for my eyes and fingers to both her asshole and soft pussy.

Believe me when I tell you that neither John nor I had erections up to that point, at least not full ones; our bodies were still responding to this as a massage session. But this soon changed as Kay expressed delight at greater pressure from John's fingers, which given the oil soon turned into actual penetration, at which she squealed and demanded more. On hearing this, Helen looked back at what John was doing, briefly at me, then back at Kay, and asked what it was like. Kay said it was really good as long as there was enough oil and the initial penetration was slow. There was a little pause before Helen said "OK," and that plus a very, very slight movement of her hips backwards indicated that she was speaking to me as much as to Kay, and so, with John looking on approvingly and reassuringly as I added a few more drops of oil to my fingers, I began to slide a thumb into Helen's anus. Wow, that was amazing! I was surprised to be touching a woman so intimately, when in the morning I could never have dreamed that something like this would happen. "Mmm, nice" Helen said, assuring me she enjoyed it. I actually wasn't very stimulated by it, but her expression of approval made me glad to try it.

Kay and Helen's arms had been outstretched between them, but now they bent them at the elbow so that their clenched hands were just above their shoulders, which I took to be a greater sign of solidarity. My interpretation was that Kay was giving Helen reassurance about the physical part of the sexuality, which was newer to her than to Kay, but that Kay also acquired greater confidence through sharing the experience with her best friend. She was more experienced, but still young and far from jaded, so together they were stronger and more able to take new steps than either would alone.

Kay now moaned "deeper—deeper!" while Helen expressed softer and more hesitant approvals; I once asked her if it felt ok or was moving too fast, and she said it was, though I felt a tiny bit of uncertainty in her voice, as if it wasn't quite perfect. Or perhaps she was just as overtaken by the newness of it as I was, and didn't know what to expect. Perhaps, too, she was trying to show to Kay that she wasn't afraid of exploring this aspect of sexuality, and trying to bond with her by trying to experience the same pleasure. I'll never know if she enjoyed it as much or came to enjoy it later the way Kay did, as we never spoke of it later.

Before long I noticed that John's cock was hard and pointed straight at Kay's backside, and he began touching it to spread the oil around more evenly. Soon my own body seemed to take notice that the context had changed from non-sexual fun to actual penetrative possibilities, and I followed his lead. The hot oil on my dick felt really good, it was already hot and held in my own heat better, and the smoothness of the lubrication was perfect, so I was standing out hard in seconds. At some point Kay said "I need more," and John needed no further encouragement to withdraw his thumb and begin sliding his long rod into her anus. "Yes!" she cried, "that is soooo good!" Helen watched her friend enjoy this for a minute or so, then turned her head back to look at me for a few seconds. While she neither spoke nor gestured, I took this as permission to enter her the same way.

John looked at me and, presumably recognizing that this was my first time, and Helen's as well, advised me to "go slowly and take it easy, it'll go right in." As between the girls, there was definitely some bit of mutual reassurance between us; I needed encouragement for my first time, and John probably benefitted by being not the only one to engage in this public and potentially embarrassing act in front of strangers. So I too removed my thumb and slowly pushed the head of my cock into Helen's anus. I had only had sex a few times before, and was amazed at how much tighter it was than a vagina, in fact I was startled at how easily the oil helped me slide in given how small the opening looked and felt.

Once I was in several inches, I was even surprised at how little her asshole even looked like an asshole anymore, there was just smooth skin around my penis, not the tiny brown speck I had been pushing my thumb at earlier. It was as if a hole had simply been cut into her skin somewhere and I was slipping into it. But the tightness was strong, and the heat of her muscles was overpowering. I gripped her hips, feeling the fullness of her curves, and started thrusting deeper into her bottom, as I watched John do the same.

Helen and Kay now looked at each other more steadily, rather than back at us. John and I started thrusting in unison, and for a while it felt like we had scored something wild: two young co-eds were laying in front of us, passively exposing their bodies for us, assholes stretched open for our hard cocks to enter. It was like we had gone straight to the most intimate, exciting, and unlikely form of sex, skipping all the usual in-betweens of fondling, vaginal intercourse, or even kissing. We had somehow inside the most intimate parts of these girls' bodies. I soon confirmed that anal sex lived up to all I had heard about it, as the heat and tightness gave me far more intense pleasure than intercourse had even done. We were in like Flynn, and were living and fucking to the hilt.

The fact that we were doing it in unison, in parallel, made it at least twice as exciting. For some reason I have always found images—admittedly, more often in porn than reality—of parallel sexual actions to be tremendously exciting. Perhaps this is because it emphasizes the act over the couple, as if the plan to perform that specific activity dominated the choice of partners. It's like, if you see a couple engage in oral sex, you just think, OK, that's what they want to be doing right now, it's because it's because they chose each other and this just happens to be what they're doing right now. But if you see a row of two or three men with a woman kneeling in front of each, it's like: this is a blowjob room, you walk in and you can expect a blowjob. Likewise, this was the anal sex room: you walk in here, and you can expect some ass fucking with whoever's available. Who you get is less important that the fact that you'll get your rocks off.

While the idea (however real or imaginary) of getting automatic penetrative action was tremendously exciting for a while, at some point this feeling was replaced by the odd thought that I was being used. Not in a wholly bad way, and not in a way I am convinced was real. But it started to feel as if I and John were both there to service the girls in this new sexual experience, and in particular I was there to help Helen bond with her friend. Feelings of camaraderie with John left me suddenly as I saw how he was enjoying himself with gusto, and I was trying to enjoy the experience as if I had chosen it, while realizing I really hadn't. I had just followed the lead of others—John, Kay, and then Helen, doing what they needed to complete a pattern, but not because it felt right for me.