Reminds me a suppository story a former girlfriend told me once. She and I dated for several months some years ago, she was very reluctant to discuss sex, although she was very happy to remove her clothes and engage in sex with me. I decided not to press the issue about talking about our desires, experiences, etc becuase she seemed uncomfortable with it.
One afternoon we were sitting around discussing various memories of childhood and she tells me a story about remembering a time her mother gave her a suppository. I admit I was surprised. She emphasized how it's a memory she could never get out of her head, how she remembers being sick and then told to bend over, her mother baring her bottom and opening her cheeks to insert the suppository, the feeling of her mother's finger inside her and how strange it felt. She was pretty detailed but didn't discuss it beyond that or in any sort of sexual way.
Looking back I think this was her way of wanting to discuss her own anal desires, because I recall this conversation occured just a day or so after we first crossed that line in bed. I remember pretty vividly that I was kneeling as she lay on the bed on her back with her legs spread, as I kissed and caressed and licked her pussy, something we both liked alot. Without saying anything, she rolled over onto her stomach, keeping her legs still slightly apart. Up to this point in the relationship we engaged often in oral sex and vaginal intercourse but hadn't focused at all on each other's backside. In hindsight we both knew we were very anal erotic and were embarrassed and hesitant to open up about it. Anyway so suddenly she's laying facedown, naked, her beautiful little round bottom right there in front of me, cheeks just barely apart. Wow, what a visual memory! Without saying anything I began to caress and kiss her back, bottom, legs, eventually focusing on just her ass. She began breathing more obviously, louder, as I focused nearer to the crack. She seemed very relaxed and more and more stimulated, so I placed my hands on her cheeks and gently opened them. Looking at her anus I wanted to kiss it but just breathed on it first, seeing if she would have any negative reaction to that. She just kept exhaling deeply, so I began kissing her tiny opening, and slowly licking around it and across it. A few times I stiffened my tongue and pushed inwards, just the tip of it entering her anus as I felt her push back slightly toward me. Admittedly it was all just heavenly. This seemed to go on a long time but I really am not sure how much time passed. I remember very quiet MMMM sounds from her, and louder breathing in and out.
Later that evening while we were fucking she said something, which didn't happen alot, so I remember it. She said 'You touched me in a new place today.' I said 'I liked it.' And that was all she said. So it was the next day or maybe the day after that she brought up the memory about getting a suppository from her mom.
That thought was in my mind for awhile. Soon after, one night I was again enjoying fingering and eating her pussy, and I put the tip of my finger against her anal opening. As I kept licking and kissing I pushed in slightly and VERY slowly into her bottom. Once the tip was in it felt as it her anus was gripping and pulling my finger, slowly pulling it further into her. By the time she orgasmed, my finger was all the way inside her ass as far as it could go, and I was moving it back and forth, about halfway out then pushing it all the way in. What I recall most aside from her explosive orgasm is how her anal canal gripped my entire finger, how warm it was inside, how good it felt to be fucking her ass with my finger.
Sad part is that the sex was one of the only times we both were happy being with each other. Other problems got worse between us and we broke not long after these new sexual escapades began. Never got to properly PLAY DOCTOR with her, though I was getting the idea that it was just around the corner.
Anyway seeing this thread just sparked that memory so thanks!