(This is a [MF] couple’s account, and I’m the guy.)
I lost my virginity just after my twenty-second birthday, much later than I would have liked. By that age, I had been thinking, dreaming, and craving sex for six years. Having few opportunities where I was, I sought refuge in reading about it; *if I couldn’t have it in real life*, I reasoned,* I can live it in fantas*y. I was living vicariously through second-hand experiences shared on [r/sex](https://www.reddit.com/r/sex), erotica, and pornography. I look back on those years as a maelstrom of frustration all blended together.
When six years is a quarter of your lifetime so far, it seems to drag on *forever*.
At age 21 ½, I was able to change my living situation, so I did. I flew for 24 hours, leaving my previous life behind. I arrived knowing nothing about the local culture, with the confidence of a man who has nothing other than confidence. I had my first date within the 7 days, my first kiss within 44 days, and about 224 days after touching down, I lost my virginity.
I’ll spare you the description of what we did, but it was clear from our interaction that she was inexperienced as well. Throughout our flirting and hooking up, I had been my bold and forward self. The onus fell on me to ask her out, to initiate cuddling, to escalate to kissing, and to escalate *from* kissing. I was new, unsure, and unsteady. She was attracted to my confidence. My confidence was a trick of smoke and mirrors. There was no substance of experience, only sleight. Under this pressure, I lied about my prior experience. I hid my inexperience with the boldness of my actions, and I lied by omission.
When the day finally came around, I went down on her to her vocal satisfaction. We rolled a condom on to me together, I slid into her incredible, tight, wet, silky, velvety, gorgeously warm wetness. Somehow, despite feeling all these sensations, I didn’t actually feel any pleasure from them.
Seconds later, I went limp.
I played it off (more of that confidence!) as not having been intimate in a while, and lied *”you’re really pretty and that makes me a little nervous”*. We played for a while more, I toweled her off, tucked her in to bed, and left. I remember leaving her place with a feeling o*f sho*ck*, elati*on, an*d reli*ef. I was enjoying the thrill of just having don*e th*at, but I was even more relieved that I was not missing out on this fundamental part of the human experience, and I was relieved that the massive pressure I was putting on myself had finally been lifted. I remember thinking about my seventeen year old self, and how he would be relieved to know that he would someday get to experience sex in all its messy glory.
The next afternoon, I went back (*”I think I left my keys, can I come pick them up?”*), and this time I didn’t go completely limp. I still remember how her eyes widened when she felt me entering her.
We had sex almost weekly for the next eight months. It took me about a quarter of that before sex began to feel good.
***
I came from a place with an overwhelming emphasis on work ethic and academic achievement. There were few opportunities to interact with women in a romantic context. Further adding to my frustration is the fact that I look very different (the random lottery of birth: race and medical) from most people where I live.
In that context, I was frustrated with a barely-tamable libido and an overwhelming sense of powerlessness in the face of my desires. When I had the chance to have sex with someone who found me attractive, I leapt at it. I now realize that I was only somewhat attracted to her at the time, even though she was physically attractive.
She was a perfectly lovely young woman, and my performance was in no way her fault. I take solace in that, when we stopped seeing each other, she told me of her positive feelings about our time together.
***
It has been some time since that happened, and I have been fortunate to find a partner who I love deeply and with whom I have fantastic chemistry. We have learned and grown together, as people and as sexual creatures. She is good, giving, and game; and we have explored and learned about our sexuality together. With her I feel love, trust, and acceptance. With her I can be vulnerable and open.
I told her about my past and this formative experience, and then I asked her if we could explore this again in role-play. We had this on the back-burner for a few months, until we had a relaxed evening together earlier this week. (After a long spanking session with a Hitachi.)
We started with a small drink, and then sat together with some tea. In that moment, I was able to be unsure and hesitant, responding to her invitation for tea and letting her take the lead in everything. We giggled a lot at the start, and got more and more into our roles as time passed.
It was an amazing experience. Where I had hidden my feelings, I instead felt safe enough to be afraid in front of her. Where I had to guess and improvise, she taught me exactly what to do. Where I was relieved to experience something, I instead felt physical pleasure. I came inside her and instead of pulling out, we just snuggled and kissed and enjoyed the post-coital glow.
Sex with someone you love is transcendental. When you can share every ounce of your vulnerability and receive reassurance and validation of yourself in such an intimate manner, it turns fun bedroom gymnastics into and intimate sharing of self.
Source: reddit.com/r/gonewildstories/comments/8o58fu/losing_my_virginity_and_again_in_roleplay
Nice, it wasnt easy. Memories will last forever.