Lost my virginity to an escort. Unexpected results Ensued. What happened your first time?

So, I’m a 20 year old guy. Was a virgin this morning. I had decided a while ago that I was sick of the V-card and wanted to get rid of it. I also didn’t want to be extremely awkward and have no idea what I was doing when I actually have sex with someone I’m in a relationship with. And so, my search for the perfect escort began.

I found a really good company that had really good local women, and at fairly high standards and charges. Looked good to me. Booked an hour with a girl at her apartment and went on my merry way. I have to say that at this point while I was waiting at her door that I was really really fucking nervous.

So, she opens the door and she looks pretty much exactly how she looked in her pictures (thank God for that) which means that she was extremely fucking hot. She took me into her bedroom and I said that it was my first time so I’d like her to lead.

“Oh first time using an escort?”

“Uhh… no. First time, first time”

“Oh! You’re a virgin?”


So she took the lead, we took our clothes off and laid down by each other and started off with some kissing while she was stroking me to “get me hard”. Kissing was pretty meh and I wasn’t excited as I thought I would be. I thought that was fine and I’ll probably get into it once things got hot and heavy.

Next up, she put a condom on me and started sucking me off. I guess it felt good, but again, my feelings were basically… “meh”. I just laid there and she kept sucking and sucking and well, I could tell that nothing was going to happen, so I just asked her to jump on.

She swapped the condom and slipped my penis inside her. That was it, this was the moment I was waiting for, this was going to feel AMAZING.


Again, I guess it felt good, but again, was extremely meh. I started thrusting back, but ended up getting bored and just laid there. She swapped to reverse-cowgirl position, and it felt better, but it was still really boring.

I asked if I could be on top, and started doing her missionary style. I guess that was a bit better, but not by much. At this point, I just wanted to bust my nut and get out of there. This was not at all how I expected, I thought I was going to be so psyched that I would bust within a few seconds. So, I got her to turn around and started doing her from behind and just thrust as fast as I could. I was worried I wasn’t going to cum for a second and considered faking it, but sure enough, a few more minutes and I was feeling like I was about to cum. Went for it for a bit more, and.. well. LIFTOFF.

Then I just laid there for a bit, we had a bit of a chat, I asked her what time it was and turned out I had 25 more minutes (I’ve booked an hour) so I could have rested and had another round if I wanted to, but in all honesty, the best way I could describe the encounter was “assisted masturbation”

Before I went, I was expecting to either leave in a moral crisis (for losing it to an escort) or to be hooked on it. I had no idea that I would leave feeling, well, nothing. To be honest, I still consider myself a virgin. That was not sex, that was not what sex was supposed to be.

So, by the end of it, I have mixed feelings. On the one hand, I’m glad I went as I now realize what little sex means if it’s not with someone you’re really into. I’m not naive, I knew there would be no emotional connection, but I thought there would be a sort of physical intimacy. I mean I was having sex with a woman for crying out loud, there had to be SOMETHING. I also now realize how little the “V-card” matters. It really really doesn’t. At least not as far as sex goes. I’m now redefining the meaning of the word “virgin” to myself. Now, losing your virginity doesn’t mean having sex, it means being in a proper relationship with a girl you really care about.

The only downside honestly is that I feel like I wasted a bit of money. Then again, thinking about it, no matter how meh the experience was, if I didn’t have it, I would probably still be stressing over the idea of sex.

So.. in the end, no regrets. Certainly no moral crisis because I felt like that meant nothing, so there’s nothing to panic over. But yeah, that’s my story, and I’m sure as fuck not telling it to anyone I know, but I wanted to put it out there.

What happened your first time?  Good, Bad, and War stories welcome.

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