It wasn't until I was 16 years old that I had what I would call a real sexual experience. I started dating a girl, Carolyn, who was 15 like me, and eventually we were both virgins and lost our virginity to one another when we were 18. But in between, whenever we could find the time and place (tough when neither of our parents went out of town often), we played around and learned a lot about sex with one another. We were both very naive and "good kids". Both actually quite shy and definitely reserved to, like you describe yourself. We got decent grades and didn't get in trouble. I met Carolyn in a class when we got partnered for a project. Lucky for me, we hit it off and it was comfortable and easy to talk with her. So it was obvious pretty quick that we liked each other. I honestly don't remember our first kiss but I do remember the first time I saw her naked, which, if you know anything about guys, is a big deal, especially the first time. For a few months we just kissed and touched each other with clothes on. Pretty tame and unadventurous, but we were both very happy and probably afraid to go further too fast.
One particular night began with us sitting on the couch in her parents' living room, chatting as we often did. And since her parents forbade us to be in her bedroom, the living room was the best option since it was the furthest from where her parents usually were, and with hardwood floors, we knew we could hear someone approaching. As usual at that point in our sort-of-sexual life, we knew we would be making out on the couch and who knows maybe a little more. Recently she'd allowed me to caress her under her shirt, which was mind-blowing for me, to touch her small, tender breasts and so soft little nipples. I couldn't wait to do it again, thought about it every day especially when we had that one class together.
So this one night we were talking as we often did, watching TV, waiting for her parents to go to bed so we could kiss and touch each other. At this point we'd never actually been naked with one another or anyone else. This was unchartered territory. I was caressing her legs as we sat on the couch, and she eventually lay down on her stomach. I recall very well that she was wearing a jeans skirt that reached her knees and a white t-shirt. She was thin though a bit curvy and had pale supple skin. Really lovely and irresistable. My caresses went from ankles to thighs, slowly made their way up to her upper thighs. As I inched upwards, I was testing to see if at some point she would become uncomfortable. I was being gentle, just enjoying touching her. She was very relaxed the whole time. Eventually, to my total shock and amazement my fingertips reached the bottom hem of her underwear, so I slowly began caressing her bottom over her panties, again waiting for any negative reaction. None, she seemed relaxed. Her head lay sideways on her crossed arms. After some time, her skirt still fully covering her, I slipped my fingertips into the waistband and I'm sure I was holding my breath that she wouldn't freak out, so I slowly slowly pulled them down. My hands emerged from her skirt, pulling her panties down off her hidden cheeks. Suffice to say, my heart was just about beating out of my chest.
Basically, after eyeing this young lady since the beginning of high school, watching her from a far, here I was straddling the back of her legs, my hands about to attempt to go up under her skirt and begin to caress her bare ass, that lovely ass that I was just dying to get my eyes on. Basically, I was in heaven, and greedy. Slowly I pulled her underwear down below the hem of her skirt and to her knees, and then slipped my hands back up under her skirt. I began touching her bare ass, running my hands gently all over her cheeks. Wow, I thought I had never felt something so soft and tender. Unbelievable, I recall just gently caressing her skin, occasionally squeezing those little round cheeks. But I just had to have a look. If she's let me come this far, I was thinking to myself. I'd only seen a woman's bare bottom in magazines up to that point, the internet was still a few years away then, and I thought, "I'm about to see one for real". For a 15 year old, this was a big moment. I pulled my hands out from under her skirt and began to raise her skirt up to her waist. And there it was, her lovely, white, pale, round, small bottom there just inches from my eyes. I must say, looking back now at this very vivid memory, she had a truly beautiful behind. I can still picture it as I sit here recounting it. Such pale skin, with tiny freckles here and there, so smooth. I think I could feel my blood pumping through my body at that point. And it felt hot.
At that point, having pulled down her panties, I think I just stared at her bare white bottom and caressed it for I don't know how long. Delightful, exciting, heart-pounding, words don't describe whatever that feeling was. At one point, I was not sure what to do, so I began to explore a little more since she never flinched or hesitated at all up to this point. That gave me so much confidence and pleasure. That dark crease between her cheeks was just there in front of me, just asking to be opened, explored, inspected. Incredible that she might actually allow me to do this, so see such a private, forbidden part of her 15 year old body. And even though I knew my biology facts and knew that, well, 'everybody poops' as they say, it really was sort of beyond me that this adorable young girl could even have an asshole. Yet I so wanted to see it, craved to look at it. I didn't know why and still don't, but at this point bent over her backside with my hands on her cheeks I was about to do something I'd long desired to do.
I was sooo excited with what was right in front of my eyes, and with what was hidden from them, but just inches away. With each hand on a cheek and my thumbs resting just along her shadowed crease, I took a deep breath and slowly and gently pulled her bottom open. And all of a sudden there I was looking at my girlfriend's most intimate area, her little anus completely exposed to my stunned eyes. I also very distinctly remember also seeing her very pink and slightly hairy vagina partially opened up just barely visible between her thighs, just an inch away. WOW. What a sight this was.
For I don't know how long I just stared, just looked in sort of awe and excitement and with a feeling of complete naughtiness. I didn't say anything, nor did she. I wanted to say something like "Your bottom is gorgeous", "Are you OK with me doing this?", but I couldn't get any words out. Though she was well past those early years of puberty and had pubic hair, her anus was hairless as far as I could see. It was so small and just barely wrinkled, though actually quite relaxed, not tightly squeezed shut, a very pale pink, and totally absolutely clean. For me, I was simply looking at a totally private, tender part of my girlfriend's beautiful body, and because she was calmly allowing me to, it was all the more powerful.
I began to gently kiss her ass again as I held it apart. Incredibly soft and smooth skin. And then bit more then on the inner skin of her cheeks. Then, eventually, I don't remember why I suddenly had the strong urge to kiss her right there on that small opening. And so I did. Brought my face close in as I spread open just a bit more, took a long look again at her sweet little hole and placed my lips upon it, giving her a kiss. And another. And many more. She lay unmoving, just breathing a bit heavier now. My kisses became a bit more intimate as I began then to lick her anus, feeling the texture with my tongue, moving around and around and gently touching the tip just into the deep soft middle her tiny anus. Not pushing in, just touching. And she never moved or pulled away, just that deep heavy breathing.
I have no idea how long this all went on. I didn't ever stop. I was literally in a trance. At some point, she calmly, quietly reached down and pulled up her panties and we arranged our clothes and I went home to my parents' house to bed. I still wonder if I kissed her goodnight after that. I have no memory of any conversation as she walked me to the front door. I do remember driving home in my car in a complete daze, not believing what had just happened. Then lying in bed replaying the whole scene again and again and again.
Somehow we never talked about it. It happened many many times again over the course of the time we dated, so clearly it was something she was ok with and perhaps even liked very much. But I never asked. It was just too sensitive or taboo or unmentionable a topic. She was too proper to discuss her own asshole, I suppose. Actually, the only time any talk of it came up was when once I started to caress her anus with my finger and began to push the tip inside her hole and she resisted, asking me not to because she was as she said "very small there". "I'm very small there" was exactly what she said, in a gentle voice, I do remember. I didn't want to hurt her so that was that.
Carolyn never once touched my between my cheeks, never even got close. I never asked her to. Never had the nerve. Even when she massaged my back a few times, she seemed to treat is just as a massage. I would have loved to have introduced a "play doctor" scenario, I just didn't have the presence of mind. Everything else about our sex life was great and she was as eager as I was.
What I realized much later, after I'd had some partners who truly did enjoy anal play and were deeply needy when it came to their own, and my, anus, is that Carolyn was simply not like me when it came to sex. Carolyn enjoyed it and was curious and was happy that we were "boyfriend and girlfriend" and were "in love" and that our sex life was part of or an expression of our love. To be brutally honest, I'm not sure how much in love I was, except for in love with having sex with her, though we were friends and got along well all the time. But she wasn't really into sex like me, and she certainly didn't want to go any deeper, literally, when it came to either of our bottoms.
So between that visit to the pediatrician, in another blog post, and this experience with Carolyn, my attitude about anal sex and anal play was basically very, very intense and very, very positive from a young age. But it wasn't something I shared with Carolyn. Most of the feelings remained inside of me and my head. For me, I could not deny how physically and emotionally powerful the sensations were, the intensity of being exposed in such a manner and in exploring someone else so very intimately, of trusting and being trusted with something so naughty, even nasty, and taboo. Except for me, the reality was that it was only nasty in my mind. Carolyn was such a proper and extremely clean person in every way, that these initial explorations of her bottom were anything but dirty or offensive. They were very positive and, so although I was embarrassed, ashamed even, of my desires and reluctant to open up to anyone yet, I was increasingly curious about it, wondering if it would ever happen again. "Could there be another woman somewhere who would allow me to explore her in such a way???" and "Might there actually be a woman somewhere who feels the same way I do???" and "Will I get to play doctor with someone some day? Will I get to be the patient too?"
Another blog post answers that.