It went really well.
Had horrible social anxiety, barely ever dated at all, never got anywhere.
Turned 30, decided to just get it over with, researched for a couple months, found an exceptionally hot and talented high-end ($800) escort.
Flew to her city, got a nice hotel suite, had her over, went three amazing rounds (didn’t know I had that in me).
Anxiety gone, had a girlfriend within a month, married a few years later.
Best money I ever spent, seriously.
I much later realized that prostitutes are a very expensive addiction that isn’t very easy to ween yourself off of.
I spent a weekend in Vegas alone. Walking down the strip drunk the last night I saw this smokin hot woman and said, “hey what’s up.” I was surprised when she actually stopped but she was dressed very slutty. She asked where I was going and we negotiated price.
I was pretty worried she was a cop but was drunk enough to think fuck it whatever. We got to my room and talked for awhile. (I talk people’s ears off when I get drunk.) Then we got to it. It was awesome. Even did it on the balcony over looking the strip.
So there we were, on deployment in Thailand. I was 22, and we had a weekend of liberty to go out on the town. We decided to make the 4 hour pilgrimage to Bangkok (We’re on the train to Bangkok!!) So it was well known in my group that I was a virgin, and was truly not looking for anything but some sightseeing and exploring.
Anyhow, that night we ended up at a bar called the Pink Panther. (Go-go dancers and live muy Thai fights. Who could pass that up?). So I was about 6 long islands in, and we each had a dancer on our lap. Everyone was talking and laughing, it was really a good time. Then a couple of my friends got up and said they would be right back. Not unusual for these guys to go off on some goofy adventure so I didn’t think much of it. What they had actually done was go out, find a street drug dispenser, and try to haggle for cheap knockoff Thai street viagara. That is a whole story in itself, but needless to say they were successful. By the time they returned, I was a couple more long islands down. They got back, crushed up the viagara, and mixed it into my drink. Yeah, it tasted like bitter chalk, and yeah I knew something was weird. I said something about my drink being nasty, and my friend told me that he had squeezed a lime into it.
My drunk brain thought that was a perfectly valid answer, so I carried on. It wasn’t much long after this that my dancer got up and walked away. I didn’t think much of it, just figured my time was up. Then Mama-san came over and asked for, like, 30 bucks or something. I figured I was paying for the girl sitting on my lap for the past couple hours, so I happily obliged. Seemed more than reasonable. Anyhow, shortly after that, the girl showed back up in her streets with card that had my hotels address on it and room number (the viagara friends are a couple of sneaky bastards). They already had a cab waiting and gave her the card because they knew I wouldn’t remember the name of the hotel.
So we go back, and I’m still completely confident that i can resist the temptation (she was absolutely gorgeous). We get back to the room and she tells me to take a shower. I guess this was customary, and I needed one anyway so no biggie. I take my shower, get out and lay on the bed and wonder how im going to get out if this as she takes her shower. Anyhow, she comes out wearing nothing but the complimentary hotel bathrobe (all closed up though). She stands at the foot of the bed and asks to see my phone. I’m like, sure why not? It’s merely a camera and music device this point since I don’t have cell service or anything. Well, I’ll be damned if she didn’t put on “Shook Me All Night Long” by AC-DC, and proceed to strip the robe. Checkmate. You win.
Oh, and viagara is miserable. The whole next day, every little thing caught the little guys attention. Not to mention your lower abdominal muscles are sore as hell. I thought I caught a damn std (yes I wore protection. Another check in the box for the thoroughness of my asshole friends) anyhow, no regrets. Didn’t lose it in the back of my car in high school like everyone else. It’s a story and a memory and apparently I’m still a legend of some sorts in my old unit.
18-year old me, just let loose in Amsterdam, walked through the red light-district and thought “Why not?” Well, because it’s not cheap and I get (almost) the same results from my right hand.
Was 25. Wasn’t really bothered about being a virgin but figured if i lost it this late i might as well lose it in an interesting way. So my first time was a threesome with 2 thai prostitutes, of which one anal. The sex itself was what you’d expect for a first time, awkward but good. Was kinda awkward when after the first time i came one of the girls asked me “you papa me mama”, since she had a baby, to which i politely replied “me no papa.
The most awkward part was really picking out the girls. I mean, i went into the brothel and some fat big half thai/half american dude comes walking up to me with a thick American accent “Welcome to our establishment how can we be of help today!?”. He’d line up the girls, like 12 of them, and there was a yellow line in the middle. And he went “now remember, right of the line anal, left of the line no anal!”. So well yeah, i just stood there for a bit not wanting to pick any girl because i didn’t want to disappoint any of the girls by not picking them (which sounds kinda weird, i know that).
I attempted to lose my virginity to a prostitute in a country where it’s legal. The experience was very nice, however I was not successful in PIV sex (which some consider “the virginity”). The lack of success was due to my very sensitive penis head and extreme pain when trying to insert.
The lady I saw was very nice and attractive, I visited her at her home. She ask me to undress. She made some small talk asked where I was from and complimented me on my body which felt genuine and really that’s all that matters. She rubbed me down and we kissed and four play stuff. I tried to insert but the pain caused me to lose my stiffy. So she ended up giving me a blowjob (with condom) and then a hand job to finish off.
Now after, she cleaned my penis up with a wippy and she was very caring. She mentioned that it looked like I didn’t wash properly and gave me tips on how to keep my tip clean. Which was helpful because as a younger man (who was not getting any action) I was not very good at cleaning especially because it was painful for me at the time.
Because I paid for an hour and had only spent maybe 15/20 min with her she gave me a massage. After a few min of this I got another hard on and I asked if we could go again which she obliged for another $20 with another blowjob/hand job. I probably stayed a little more than the original hour I paid for.
We showered then dressed, she hugged me as I left.
Age 28, after chatting to a psychologist for about 2 years they helped me realise it was something I should seriously consider. “Getting with women” was a big mental obstacle for me, I’d never kissed a woman at that point, only held hands with one at age 26.
To paint a quick picture; I’d had a woman on my couch, alone in my house with me, stroking my hand and leaning on me, after I’d cooked dinner for us, and I was too terrified to do anything.
So age 28, after weighing the pros and cons, I decided to go for it. Where I live it’s not uncommon for guys to go to a local whorehouse (we call them brothels, much nicer name…)
I went along during the middle of the day, nervous as hell. But confident in a way, that this would be fun and interesting, at least.
The hostess puts me in a room and 4 ladies come in 1 at a time. I liked 1, she was about mid-20’s, had brown, short hair. wearing nylons, which I found attractive. Also she had tattoos.
The hostess comes back and asks if I’ve decided, I mention the lady I want (above). She comes back in and takes my hand to the room. Basically from there she points me towards a shower in the next room, I shower, and there is this thing where they inspect your junk for diseases under a lamp. Kinda kills a bit of the mood but it’s necessary and makes you feel better about their health.
Anyway I tell her it’s my first time, like, ever. And she says “good for you” etc and is very reassuring.
We start with a massage, I’m on my stomach and 5-10 mins later she puts a condom on me and gives me a blowjob, honestly though I just felt kinda bad for her, like “why would anyone want to put my dick in their mouth?”
From there we did whatever the opposite of Missionary is, I was on bottom and she was over me on her knees. I lasted about 10 minutes which I was happy about.
For the rest of the 20 minutes or so (I’d booked 45 mins, $150USD) we held hands and chatted. Honestly my favourite part was the holding hands and chatting. Sex felt good but the closeness of holding hands lying next to eachother was nicer.
Since then (4 years later) I’ve dated a couple women and although I haven’t had sex with a free-range woman yet, I’ve had oral sex (giving/receiving) with 1 and just started a new fling with a nice lady and it’s looking great.
I was 21 years old visit Las Vegas for the first time (friends 21st birthday). Had an awesome experience met her at a casino bar after winning around 300 USD playing roulette. She walked right up to me and I bought her a drink. Ended up finding out what her line of work was and decided fuck it let’s do this. She even had a small blunt that we smoked on the way. (Which was awesome)
She ended up being the same age (only a couple months apart) very cute light skinned African American girl with pierced nipples. I also found out that you’re not supposed to kiss them (lol I know why would I do that?)
Ended up lasting the 30 minutes that I paid for and I’m pretty sure the room next to us could hear the bed against the wall lol.
Overall I would say definitely the best night of my life and probably runner up to the best vacation I’ve ever had. 10/10 would recommend to anyone feeling a lot of pressure to lose your virginity.
So I was just 18 and wanted to fuck. Got to a prostitution street in my city, choose one with big boobs and blonde hair. She looked gorgeous.
We went inside and I told her it was my first time, and she said just to relax. She thought it was my first time with prostitutes. But when I tried to put the condom on she was like, wait, is this your first time having sex? And I said yeah.
She then asked me if I was sure I wanted to do that, if I won’t have any regrets. She was pretty nice to me so I told her I just want to fuck and experience it, and so we continued.
She laid down and said to put it in, which I did. Her vagina was so smooth it felt like heaven. Because I wanted to last, I masturbated in the morning so I didn’t cum right away. Maybe it took 10 minutes or so?
Anyway, first was missionary, then she said she’ll make me cum and put me down and started cowgirling. Oh man did her thrust felt good. I came pretty quickly.
Somehow I was still hard, and we talked a bit about stuff cuz I paid for an hour. After about 15 mn or so I just wanted to fuck again and she told me she’d blow me. It was heaven. I don’t know how she did it but it felt incredibly good.
I was about to cum when she stopped and said that since it’s my first time, I should experience it all and asked me to fuck her in the ass.
I think I came after 2 minutes or so. Best experience ever!
After that I went back a couple times and always fucked the same girl.
Maybe it was because we fucked many times that I got confident or so, and finally got a girlfriend and that was the last time I fucked that prostitute cuz after that I moved to another city.
No regrets, except I want to go back and fuck her sometimes. Her vagina smelled good too.
While working a summer job at age 16, my boss decided to treat me to a massage for a job well done.
We parked behind the building in a secluded, fenced-in area and I’ll never forget the comical smile and thumbs-up a middle-aged man gave me as he was leaving. At first my presence was met with much resistance by the woman working the front of the house but eventually she relented, grabbed my hand, and led me to a room in the back where I was given a table shower. After the shower she walked me to another room, which reminded me of a doctor’s office, gave me a massage, and my first sexual experience.
The masseuse was very attractive, looked to be in her mid-thirties, which complimented my MILF fetish, and spoke English well. She insisted I rub her shoulders after since I asked her to be on top. We talked for a short time and I remember being asked my age and telling me I was a nice boy and I needed to get a girlfriend instead of paying for it.
In retrospect I have very mixed feelings about this. Since then I’ve developed more of a conscience and part of me is worried that I supported human-trafficking in some way. Then again, I don’t view the experience negatively. I’m not interested in going back but I don’t regret it.