[Serious] Guys who lost your virginity to a prostitute, how did that experience and your sex life go afterwards?

LONG READ AHEAD I lost my virginity to a $60 hooker off backpage when I was 17. One of my favourite things to do at the time was to look at prostitutes on various websites and jerk off to the fantasy of meeting one, well, one day it stopped being a fantasy. I saw an ad for a lady named "jenna": 28 years old, DDD tits, big booty, $60/hh and, conveniently enough, only 15 minutes down the street from my house. I said to myself "fuck it, I'm tired of being a virgin, I'm going to take the plunge". Being relatively clueless about the whole procedure and wanting to protect my identity, I texted her using textplus, (an android app that gives you a fake local number to text from)

Me “hey when can I meet up with you” Jenna “any time after 6 is good” Me “cool, I was just wondering, do you see virgins?” Jenna “oh no sorry hun, I don’t” Me “why not??” Jenna “it’s weird, and you shouldn’t lose your virginity like that” Me “ok… have a good one”

FUCK, time to get a new fake number. I didn’t particularly enjoy having a $60 hooker taking the moral high ground over me, but, I didn’t enjoy being a virgin even more. So I waited an hour or so then texted her using a different number, set up the date and headed over. She told me to wait at a coffee shop that was close to her apartment while she was “getting ready”. My heart and mind where absolutely racing, was I going to get robbed?, stabbed?, refused service?, “who gives a shit, I’m in too deep now”. Then I get the text “I’m in the Condo across the street, buzz apartment number 6” so I leave the coffee shop and head on over. Now I’m standing in the buildings waiting area, I buzz the apartment number and clink the door opens, I hang a left and walk to the end of the hallway and right at the very end I see a busty chick , maybe late 30’s or so, wearing a pink see-through babydoll and a g-string thong. At this point I’m sweating like a motherfucker, my heart is pounding, I think to myself “this chick’s fatter than the ads, but I can dig it”.

We walk in to the bedroom and she asks me how old I am. Me “I’m 19” Jenna “really, cos there was this guy earlier who said he was a virgin, you sure you’re not him?” Me “umm no, I’m not a virgin”

She asks me for the money, I hand it over and she starts to leave the room.

Me “where are you going????” Jenna “relax, I’m just going to put the cash somewhere safe” Me “oh, alright” Jenna “ok, strip down, and lay on the bed, I’ll be right back”

So I strip down and lay on the bed, I’m already rock hard from all the excitement, she comes back in the room and says “you’ve got a pretty big dick for a 19 year old” and I respond with a rather naïve “ whoah, really??, thanks!”. It’s at this point she opens a dresser drawer, grabs a bottle of lube, cups her hand, pours some lube into it, and, in a rather unladylike fashion, shoves a bunch up her pussy. I found that quite repulsive but I had already gone too far and still wanted to fuck her. She grabs a condom out of a big box of them and proceeds to lay down next to me, gives my dick a 5 second handjob and then applies the condom. Now she’s blowing me with the condom on, kinda laying down next to me, not on her knees so I put my hand on her head to aid with the rhythm. She takes her lips off my dick and says “don’t touch my hair”, “oh, sorry!” I respond and she continues with the blowjob. After maybe like 2 minutes she flips on her back and spreads her legs, pussy laid bare, this is what I had been waiting for. I get on my knees and shuffle closer to her, rub my dick around her lips a bit and then, the magic moment, stick my dick in her. Remember how I was a virgin but lied and said I wasn’t?, yeah, she knew, right at that moment, she fucking knew. I ask her if I can suck her tits “sure”, she won’t make eye contact with me. I’m laying on top of her stiffly, pumping awkwardly and I go to deep, “OW, you’re going to break my vagina!” I apologise and we switch positions. I flip her over and start fucking her doggy-style, which is much more comfortable for the both of us. As I’m slowly pounding away she pipes up from way in the front “you like big asses” which I respond to with “yeah, I do” then she says “well, you came to the right place I guess…..”. I cum, clean up, put my clothes on and we sit down next to each other on the bed. Now that the fog has been lifted from my horny teenage brain I ask her “hey you don’t have any std’s do you” she looks taken aback and says “nope!”, I’m relieved (lol). She then gives me a cigarette and sends me on my merry way. As I’m walking home looking at the cars drive by me on the street I feel as if everyone knows I just fucked a cheap hooker, and I feel kinda dirty actually. Was it worth it?, was it fuck, I should have spent at least triple the amount to get a half decent hooker who would’ve given me a better time.

Everybody’s first time is awkward, you should share it with someone you care about, someone you can look back on that moment with and laugh. Thanks for letting me share my story with you guys.

/r/AskReddit Thread