The story of how I lost [M]y virginity to an escort when I was 25.

It was 2017. I was depressed (well, more depressed than I’d ever been); the mysteries of stochastic calculus were eluding me to the extent that I would later fail a class, and I was stuck watching Bitcoin ride to unforeseen heights while having been liquidated a few weeks prior.

It was a cold winter weekend in Toronto when I decided it’d be a good time to lose my v-card. Like many holders of that not-rare card, I was generally pretty affable and social. I had lots of friends, a decent part-time job, and was pretty educated… yet, I never felt comfortable with actually getting intimate. My sex life was generally restricted to online daliances on Reddit, where some lovely lady and I would exchange passionate drivel while exposing our respective special-parts to one another. I never felt really crushed or depressed by the idea of being a virgin, but it did stick out to me that there was an expanse leading towards adulthood that I’d yet to cross (spoiler: it didn’t change anything).

I went on a local site for browsing escorts and found one who I found attractive. She had a nice big booty and seemed very classy. I tried my best to avoid the tell-tale signs of human trafficking (such as someone who refuses to admit “black gentlemen”, which I sadly heard is a sign that a woman has a pimp, or giving the impression that she has a representative that speaks on her behalf). It was clear when I was texting her that I was actually texting her, and the flier she gave was something that she probably made herself (perhaps in like Adobe Illustrator or something). I booked a half-hour appointment with her for 1:00 AM and was on my way, driving across the city to a hotel that felt like it was in the middle of nowhere.

I tried my best to look inconspicuous entering the hallway, my jacket zipped all the way up and my hood on. In retrospect, I definitely looked like a dweeb. I knocked on her door and was greeted by the sight of an exceedingly beautiful woman (she was more beautiful than I’d ever seen) wearing lingerie. She looked to be about 23 and had wavy brown hair. Her hips flowed like the sinuous curves of some Renaissance statue that Tuberculosis-afflicted Romans found Venusly-arousing. She let me in, I took off my jacket, and she directed me to the shower. It all felt very surreal; the shower itself was pretty unremarkable looking, and there was some cheap bodywash (which I used) and some mouthwash (which I didn’t use), and the looming anxiety that, in a few minutes, I’d be having sex for the very first time.

I got out, dressed only in a towel and sat next to her on one of the beds (there were two in the hotel room: one of them was for sex and the other one was the one she slept on. She put her laptop on it and was playing some Drake or something). I told her I was a virgin and she was actually excited; she told me she’d never taken someone’s virginity before and that it was a first for her. She told me we’d start off by kissing and that I could touch her if I want. She said she had some beer and wine and stuff, but I decided to pass (I had a license that was a small degree above a learner’s and for which it was prohibited to have any alcohol. Kind of an odd time to reflect on legalities, eh?).

She told me I was adorable before pressing her lips to mine. I put my hand on her hip and she guided it to her breast. She rubbed my cock over my towel and took it off. She told me it was a good size before putting her mouth on it. I mentioned that I was a bit worried about busting in her mouth and she told me to just let her know if I do (presumably so she could grab one of the many tissues on the nightstand between the two beds).

It felt amazing. I loved the feeling of her tongue dancing over me while her lips compressed around me. Her hand pumped up and down my shaft while she bobbed her head on it. It was actually really hot watching her spit on my dick. Alas, such a good thing could not proceed for too long lest I lose my juices, so to speak.

After that, I laid her on her back and tried my own hand at oral sex. Now, let’s take some time for sexual education: in my deep and thorough research on the subject of eating an escorts pussy, I learned that it was generally pretty safe; the vagina is very clean (definitely a lot cleaner than a dick) and you can’t really catch anything from eating it if it looks nice. And hers looked nice. Very nice. So nice that I enjoyed the time I spent with my mouth on it. I don’t think I did a great job since she wasn’t like moaning like nuts… perhaps it was more for my benefit than hers. In any case, eventually we moved onto the more penetrative part of the night.

I put the condom on and thought about what position would be best, before eventually deciding on doggy style. It felt weird entering her… since I knew this *should* be an iconic moment… probably with someone I was in the stages of mutual-puppy-love, with the whole affair being awkward, punctuated by awkward bumbling. Instead, I was greeted with the presenting posture of a professional, with the awkward bumbling being restricted to whether I could put a finger in her ass (sadly, for anally-infatuated me, I couldn’t). I grabbed her hips and pressed myself into her, savouring every moment of being inside her. It felt amazing to see my hips crash into the ass-cheeks of someone I would be too shy to talk to, let alone make a move on. I moved my hands along her hips, and she grabbed one and put it on her breast.

I asked her if I could smack her ass and she said yes, which I did enthusiastically. I asked her if I could pull her hair which she also replied in the affirmative to, and which I also did enthusiastically. Eventually I bent over her body a bit and hugged her tight while fucking her, my chest pressed against her back and my mouth next to her ear. I felt like a gargoyle or something. I’m not sure why I did that, but it was the most intimate I felt the whole night. Eventually she asked me if I wanted to switch positiions… I suppose she realized that, at the pace I was going, I’d be fucking her for way longer than the 30 minutes we agreed upon.

In any case, we eventually decided upon her riding me. She lowered herself onto me with her hands placed adjacent to my head with her legs straddling me. She looked exceedingly beautiful while she was riding me; her hair flowed over her shoulders and I could sense how poised she was. Eventually, she leaned back and put her hands on my knees and rode me while her hips gyrated. It didn’t take too long until I admitted I had to cum and filled up the condom. She let herself off and gave me a babywipe to use. She told me I could take a shower if I wanted, and which I did want to. She did reflect that I actually went a bit over time, but it didn’t matter.

I felt a bit self-congratulatory in the shower; I was proud of myself for taking a plunge and doing something that I felt really intimitidated by. I didn’t feel like I did something seedy or desperate, in part because of how professional she was. Looking back, I felt very at ease, relaxed, and assured. We chatted a bit before I left. She told me about how some guys she sees have huge dicks and leave her sore (r/MassiveCock, I thought you were better than that?). She mentioned that she was a model and a dancer, which makes sense since she seemed extremely fit and healthy. Anyway, a few minutes later I got my coat on and bid her adieu. I wish I could say I met her again, but alas I didn’t. I did try to message her a few years later but she left me on read. I hope she’s doing okay. I could tell that she was a pretty strong-willed and independently minded person, so I’m sure she’s doing just great.

And with that I end my story. It was long-winded. I think maybe three paragraphs out of a couple dozen were about sex, so sorry to you, my fellow literary minds addled by carnal passions. My sex life did eventually reach some degree of normalcy; I had a friend-with-benefits with whom I could be more emotionally intimate with (though with fwb situations, there’s a line with how much intimacy ought to be felt.), which was good at the time for my self-esteem.

Source: reddit.com/r/gonewildstories/comments/st6lc9/the_story_of_how_i_lost_my_virginity_to_an_escort