My 3 previous blog posts recount my early sexual awakening as a young pubescent boy, a particular sexual experiences with an older work colleague, and a post by an anonymous female author. This post is about Andrea, a woman I met in college.
After high school I ended up going to a small college in the Pacific Northwest. I'd broken up with my high school girlfriend before leaving. She was the only person who I'd had sex with up to that point and the only woman whose bottom I'd seen and touched and explored. During the first couple years in college there were plenty of parties, and I had the occasional hookup, but I didn't have a serious girlfriend until my graduation year. Before I met her, there was another woman, Andrea, and we had an off and on thing for a while. Basically, we were really into one another, but I being a guy would get bored of her company and lose interest sometimes, and she for whatever reason never complained or protested or maybe she felt the same about me. It was on and off again intimacy, but the intimate times were for me really intense.
Andrea and I didn't hook up immediately. Actually, we were classmates and used to be in a study group together. I found her to be really, really cute from day one. Anyway she had big, easy smile, blue eyes, dirty blond hair, thin with a round little butt or so I imagined, and also very smart and funny without trying to be, though very reserved in public. Her strict, successful parents had sent her to a private Catholic girls high school so she definitely had that "proper" attitude about her. She was very studious and a good student, she was shy and easily embarrassed, and although she dressed fashionable she didn't reveal much, no tight jeans or short skirts. But between that smile and that little bottom that I could only picture bare in my mind, I was in lust. And of course, she had the dreaded boyfriend.
But the boyfriend went to school in another state. Sometimes, if she and I studied at her dorm room together, I had to listen to them talk on the phone. It killed me. I remember one night listening to her talk to him, but not sounding particularly loving like boyfriends and girlfriends should, and when I glanced over at her, I started staring at her legs, she was wearing shorts, and it was just painful. When she hung up, she had a look on her face like something was wrong. I asked and she said things weren't going well with them and that they "should probably break up." And what did I do? Being both immature and uncontrollably into her, I took her hand, pulled her down to the couch next to me and not sure where I got the courage to do this after so many months just being in the horrible friend zone, kissed her. And to my total surprise and relief she responded very, very passionately. It was so wonderful. I had been imagining kissing her for a long time but never really thought it might even happen. This was probably several months after I'd first met her.
That night, we were a bit tentative, both obviously excited but also nervous. Her roommates were gone for the night, so we had the place to ourselves. She turned the lights down low, which I wasn't too happy about because I really wanted to see this gorgeous body that I'd been undressing in my mind for so long. But I didn't say anything. We spend a lot of time kissing and caressing one another. And although we were completely naked eventually, we didn't do that much, no oral sex for example. But at one point she said, "Shall I get a condom?" and I said "Yes". She got up to go to her closet and turned on the other light to see what she was doing. As she stood there, facing away from me, I saw just what I'd been imaging all those months, her bare backside from head to toe. She had just a bit of a tan, as her little bottom was slightly paler than the rest of her skin. And that bottom was so so lovely, small and round and white with a few freckles visible. I wondered if I would ever get to explore it one day.
When we actually had intercourse that night, it was like sometimes intercourse can be especially when you're young and inexperienced, not particularly amazing and too quick, which I thought was my fault. The whole time she sort of just laid there, didn't say anything or moan, and let me take the lead. I think she was very nervous. And because I was also nervous and too excited and not incredibly experienced, I wasn't sure what I should and shouldn't do or say. In the end, we fell asleep talking about how we'd both been immediately interested in one another since the first day we'd met in class and how we both were too shy to say anything. So although the sex itself wasn't crazy or wild that first night, it was wonderful to finally be intimate with one another after so long just fantasizing about one another.
The next time we got together, Andrea was much more open and extroverted and verbal. We were coming home from dinner and it being the weekend and me having thought of nothing else except her since that first night, I said, "Do you want to hang out for a while longer tonight?" And she said with a huge smile and big eyes, "My roommate went home again this weekend. Do you want to come over?" So Of course I said yes.
Andrea seemed much more at ease on this second night, talkative, and I remember that she made more noises, breathing, groans, grunts, saying "yes" alot and so on, indicating that she definitely was excited. I was still trying to get a feel for how aggressive I should be or how adventurous she might want to be. At one point we were naked and kneeling on the bed kissing and caressing and she smiled at me, looking me straight in the eyes, and then bent her head low and took me in her mouth. Clearly she had had a lot of practice giving her boyfriend oral sex. Her closet doors were sliding mirrors, which gave me this amazing view of the both of us. As she sucked me in that position, I could only see in the mirror her back and ass and feet, and what a glorious view. I was dying to explore her little bottom and wondering a little bit how different it might be compared to my high school girlfriend. Another blog post is about my h.s. girlfriend, the woman who I lost my virginity to when we were 15, 16 years old and whose bottom I got to know very intimately over a couple years.
I awoke to her hands on my suddenly hard penis and once I was awake, Andrea took me again in her mouth. Heavenly. As I was caressing her body, I eventually lay her on her back and kissed her head to toe, spending lots of time on her breasts and between her legs. A petite girl, she had small breasts, very white with some of those same freckles I'd noticed on her bottom. She also had tiny hairs around her nipples that I could feel in my mouth. Her nipples were small and dark pink and hard at attention. She endlessly enjoyed my sucking and nibbling on them. I spent even more time between her legs. In the time I'd spend with my high school girlfriend, I'd come to love giving oral sex. And so to both our pleasure, I spend a long time down there with Andrea, who had just a small amount of pubic hair there. This was before most women had begun removing it and going near-bald. After some time, from her sounds and writhing, it seemed she was in a very very happy place.
Gently turning her over onto her stomach, I finally got a good long look at her ass in the strong morning light. I got a look again at those lovely little freckles on her backside, some on her back and a few on her alabaster white bottom. I stroked and caressed her from neck to feet, all the time keeping her pert, cute bottom in my sights. It's hard to remember how long I just stared at it, but I'm sure it was quite a while. So beautiful. After so many hours wondering, here it was, bare before my eyes. Andrea seemed very happy and relaxed by now, and I began to focus my attention on that beautiful rear, starting to realize to my great excitement that I was about to explore the very private area of this woman who I'd fantasized about for so long. As my hands gently rubbed her soft skin, I straddled her legs and bent closer, bringing my hands together with my fingertips along the crease of her ass. My heart pounding, my immediate thought was "What's her reaction going to be when she feel that this very private area is suddenly being exposed?" Will she pull away? Yell? Think I'm crazy or sick? I slowly spread her cheeks apart for a peek inside. She didn't move or pull away or say a word. I held the little white globes of her bottom open and I looked. Andrea's anus was very small. A very pale pink with hardly a wrinkle around it, and if there was any hair there, it was not visible to my eyes. It was simply a tiny soft hole. She didn't have any of her cute freckles between her cheeks, just very white skin, slightly pinkish in the crease. And very, very clean.
As I explored and examined her, Andrea didn't say a word. I looked up to see her arms were crossed and her head lay upon them looking to the side. I realized then that she was facing toward the closet mirrors and was watching me, with a slight smile on her face and her eyes half closed. Bringing my attention back to her bottom, I followed my desire to kiss her right there, on that cute little opening. I bent in and gently placed my lips upon her puckered asshole. Andrea made a barely perceptible "mmm", like a little hum. I kissed on and all around her bottom hole, all over her cheeks, from the top of her crease down to her pussy. Which, I noticed was moist. I ran the tip of my tongue around the edge of her anus, eliciting more soft hums from her. After some time, I had to ask her, "Do you like when I do this?" And Andrea whispered back, "Yes."
After much more kissing and licking, sometimes daring to push the tip of my tongue a little bit into her asshole, she turned back over onto her back. Perhaps that was enough for her. Maybe she was self-conscious. Caressing and kissing her stomach and breasts, I asked, "Was that OK? Did that feel good?" As I looked at her face, I could see that she was both excited and embarrassed, her face pink either with passion or embarrassment, maybe both. She had a huge smile on her face, a smile that she was trying to contain a bit but couldn't, and whispered, "Mmm-hmm" She couldn't look me in the face. At that point, I boldly asked her if she would be willing to kiss me in that same place too. She said, "I don't know. I don't think I could do that." I didn't press the point. She seemed shy and perhaps a bit pushed beyond where she expected things to go already, but I had to ask.
We stayed in bed most of that morning, as her roommates were all gone again for the weekend. We just kept on touching and exploring and sucking and fucking, as 20 year olds like to do. At one point, Andrea was again on her stomach and I was caressing her lovely bottom again, and I held her cheeks apart with one hand and gently ran a finger around her anus. Wetting my finger with her own juices, I brought my finger back to the little opening and slowly pushed the tip in just a half inch. This sensation shocked her a bit, and she said, "No, wait, don't." I asked "Does it hurt?". And she said, hesitatingly, "Um, no, well, a little. I don't think you should." With my fingertip still there and feeling her tight around it, I said, "My finger isn't too big, I mean, not bigger than what it's used to, is it?" which I think, not surprisingly, embarrassed her again a little bit, this reference to her bodily functions. Remember, Andrea always did have a very proper, kind of conservative personality. Her parents were, in my opinion, a bit cold and unfriendly and very "respectable" in a socially acceptable way, also very rich and well-dressed at all times, and I think there was a lot that Andrea struggled with in terms of always having to be a good girl and a proper young woman. Anyway although we'd been very very intimate on that night and morning, something about discussing me putting my finger in her anus made her uncomfortable and embarrassed, even though there was something about having her bottom played with that she really enjoyed. Anyway, she was obviously not wanting anything in there, so I didn't continue.
Andrea and I saw each other off and on over the next couple years. She never put any pressure on me to date regularly or get serious. We'd run into each other on campus occasionally and go out to dinner. Some of those dinners, depending on our roommate situation, would lead to very very fun nights, where I never failed to find my face between the cheeks of her bottom, slowly rimming her, which she never seemed to get tired of. Whenever I'd look at her and say, "Turn over" with a smile, she'd smile as her face turned quickly pink and then roll over. Sometimes in the afternoon after class we would go back to my bedroom before my roommate returned, so those would be rather quick sessions. That usually meant that clothes never completely came off and no intercourse, just oral. But first I would always get on my knees and ask Andrea to turn around and pull down her pants slowly, once that cute white butt was exposed, I'd tell her to bend over, and then I'd pull her cheeks apart with my thumbs and spend a minute or so gently tonguing her little hole, before moving on to her pussy. She always came very quietly, but her whole body would shake. Amazing. I distinctly remember one afternoon in my bedroom and what she said. After I asked her to turn around and drop her pants, she hesitatingly said, "Um, I'm kind of messy down there right now." Obviously I didn't push it, and I really didn't know if she meant she was on her period or perhaps hadn't wiped too well that day, but I knew better than to ask because she was already quite embarrassed just saying that.
We never had anal intercourse. I never again tried to put a finger in her bottom. I never pressed her to return the favor to kiss or lick me there. She never touched or even saw my anus and never asked to. I assume she didn't want to. Or maybe was too embarrassed to bring it up. She never initiated any conversation about sex. As I said, Andrea had grown up very conservative in a household, despite this being liberal Oregon, a family that wasn't very open, certainly not about sex. So on the one hand although she enjoyed sex, was eager and excited each time we began to kiss and take our clothes off, and even initiated these evenings those times when she would ask me out for dinner, still she was never really comfortable discussing it or able to tell me her inner desires. Certainly she could never explain why a quiet, shy, studious young girl would enjoy having someone spread her bottom apart to kiss and lick her asshole, though she always seemed happy to turn over or bend over and slip her panties down each time.
I only saw Andrea once after college. We were still living in the same area and had dinner, during which she told me she was engaged. So that dinner ended on a completely friendly note. Being a horny male, I've often wondered if she really meant for that night to be one-last-night opportunity to be together in an intimate way. But obviously not, cause she didn't propose it or even hint at it. I didn't dare bring it up, simply because despite my total carnal desire for her, I had to respect her new relationship and impending marriage. She looked very, very hot that last time I saw her. Since then, I've only seen her on Facebook. She's older of course as we all are, but still adorable. There's two photos I return to on Facebook, one is her with her tennis foursome, her in her cute tennis skirt and those incredible legs, and the other is of her husband and I just wonder how often that face of his gets between her bottom cheeks. If ever. Maybe he's not into it, which would definitely be a shame.