Prude girlfriend - a 90s golden memory
This one goes back to over 25 years. In high school (or the equivalent of what we have in my country) I dated a girl for over three years, an eternity in that age. She was a bubbly, outgoing smart and social person, a very pretty brunette. Dating her gave me some kudos among the guys at my school I guess.
Despite her bubbly demeanour she was inexperienced in all things sexual and had severe hangups over her body, which was in fact really beautiful. (The extent to which amazing women agonize over their perceived bodily flaws still baffles me to this day, I would argue most men don´t even notice some of these hangups. But I digress…) It took us well over half a year of dating before things got intimate, and even then our first properly sexual encounter was a shared bubble bath – She even requested I look away as she entered the tub. Well, I took things slowly and respectfully. We then slowly graduated into mutual pleasuring under the covers. The way we did it was so systematic it is almost endearing to think about. When we were lying on a bed together she would slide her hand into my underpants and grab my erection, pull back my foreskin and start a slow masturbation. I, on my part, would slide my middle finger into her slit, covered in dark hair, searching out her clitoris, and start gently rubbing. Our sex was mostly like this, and although I eventually got to see her frontally naked, there wasn´t anything adventurous or too explicit. I´m a visual kind of guy and longed for a good look at her every inch.
Things took a turn when we booked a one-night cruise. Not a glamorous deal, don´t think of a Caribbean affair but rather a booze cruise across a small body of water. If you´re from the Nordics you know exactly what I mean. But we had our own cabin. And something about being out in sea, in our own cabin, without any distractions, made her relax – remember we were 18 and still living at home. Each time we returned to our cabin after some activity on the ship, we would immediately strip each other´s clothes off for some heavy petting. It was after one such wonderful session, both of us completely naked on the bed, that I picked up the courage to ask if she´d like to try a 69 – a daring suggestion given our vanilla sexual routine, and one I was sure she would refuse. She asked, in retrospect extremely innocently, what it meant. I explained the position to her. To my breathtaking amazement she got up from beside me to sit on the bed and then got on all fours next to me, hear head towards my feet. She then calmly swung her other leg over my head, keeping her other one on the other side of my head and slowly arched her back slightly, pushing her butt over my face. This movement caused her buttcheeks to spread wide open revealing a dark crack and her butthole, less than 10 centimeters from my eyes. She spread her legs so wide that also her labia spread open (she had an innie, her slit usually just barely distinguishable from under the hair) revealing the beautiful pink inside.
It was in this position, her ass and labia completely splayed open before my eyes, my prudish girlfriend asked, in a genuinely innocent tone of voice that still echoes in my head: “So, what do I do now?”. Rest assured I instructed her.
This is one of my most erotic memories of my late teenage years, and one that has a place of honour in my wank bank.
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