Losing Virginity To A Stranger

Jian

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Hi there. This is my first post on here (long-time lurker) and I've see different stories about how people have lost their virginities to people they didn't know so I was curious for those who have lost it to someone random, how was it? Did you regret it?
 

dtarlock

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As long as it is someone gentle, patient, and understanding that you may not know what you're doing (and if it's your anal virginity, he doesn't have a big cock), you should be fine?
 

Brodie888

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I don't regret it but I would have had more peace of mind if it was with someone who I could talk to after and give me honest yet thoughtful feed back.

Lots of guys at beats or on apps are there because they just want to blow and go. You want to avoid these as they probably won't take the time you need for your first time.

I would suggest finding someone who is interested in regular sex with you as your first.
 
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Hi there. This is my first post on here (long-time lurker) and I've see different stories about how people have lost their virginities to people they didn't know so I was curious for those who have lost it to someone random, how was it? Did you regret it?
I lost mine to a random guy and it’s was good. Was it earth shattering? No, was it terrible? No. It’s was fine. It happened. I learnt a lot and I never saw him again. Don’t put too much on your first time. It will rarely live up to expectations.
 
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Jake4fun3

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Was in video booth at a local book store. Had my shorts off and
my hard cock out and noticed someone watching me for two
or three minutes. We had small talk for couple minutes before
he used some lube I had and he fingered my ass for a minute
or two and then pushed his cock inside my ass for the first time.
He didn't last long and he came all over my stomach. He then
left and haven't seen him since. Don't regret it at all. It was
brief but the sex was really hot.
 

biguywholovesfrot

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It's better with someone you like or love but the with a stranger you don't have the weird after it's over talking either way you gotta bite the bullet once it's done you can pretend to be a virgin again I pretended it was my 1st time with a guy every time still do occasionally.. especially if it's straight bar we meet in ..the I've not done this before is a big turn on for some
 

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It's better with someone you like or love but the with a stranger you don't have the weird after it's over talking either way you gotta bite the bullet once it's done you can pretend to be a virgin again I pretended it was my 1st time with a guy every time still do occasionally.. especially if it's straight bar we meet in ..the I've not done this before is a big turn on for some
I certainly would drool if I thought you were doing this for the first time with me. ;)
 

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For me it was on my 18th birthday, I went for a trip to Toronto and was searching for a exotic massage. I came across a guy claiming he was a gay 18 year old Chinese masseuse so I went to his place as it was just up the road from where I was. He had me lay naked on my back while he got undressed. He gave a good rub to my upper body and then to my legs and feet and then asked me to turn over while it was difficult laying on my hard cock I did and then he reached under and pulled it between my legs. While rubbing my back and legs he kept hitting my cock making it stay hard. He put some more oil on my ass and started fingering it. I guess he could tell I was enjoying his fingers in me by the moaning I was making then he started sliding his naked body on mine and next thing I knew his cock was inside my ass and he fucked me real good. After he finished fucking me he got me to flip back over and he sucked the cum out of my dick which only took a few seconds once it was in his warm mouth. I have been hooked on getting fucked ever since.
 

steveh9

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For me it was on my 18th birthday, I went for a trip to Toronto and was searching for a exotic massage. I came across a guy claiming he was a gay 18 year old Chinese masseuse so I went to his place as it was just up the road from where I was. He had me lay naked on my back while he got undressed. He gave a good rub to my upper body and then to my legs and feet and then asked me to turn over while it was difficult laying on my hard cock I did and then he reached under and pulled it between my legs. While rubbing my back and legs he kept hitting my cock making it stay hard. He put some more oil on my ass and started fingering it. I guess he could tell I was enjoying his fingers in me by the moaning I was making then he started sliding his naked body on mine and next thing I knew his cock was inside my ass and he fucked me real good. After he finished fucking me he got me to flip back over and he sucked the cum out of my dick which only took a few seconds once it was in his warm mouth. I have been hooked on getting fucked ever since.

I love when they climb up on the table and do you from behind like that
 
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herbho

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Mine was with strangers at a gay bathhouse. Of course, it was all about the sex. I like watching others having sex, so I went and ended up getting sucked and sucking by the first guy and fucked by the second. No regrets. I have also taken the virginity of two friends - the first, the day after his 18th birthday ( it was his special birthday present), and the other after knowing him for three years. Both were kissing, sucking sessions, which ended up with me on all fours, being taken from behind. I enjoyed those more, because they involved emotion, but for mine, the pure animal was fine.
 

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I started really, really young. I can’t change what happened and haven’t spent a lot of time playing what if. In a perfect world we’d be emotionally and physically and mentally mature and prepared for the event. Mostly life happens and we aren’t.
 

tbeezy88

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Lost my virginity to a couple. They were older (one upper 30’s and the other almost 50) they took turns fucking me and I enjoyed it. Visited them more times afterwards too.
 

manunlisted

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My first time was with a random older guy I met in the park. I didn’t regret not knowing him. I was curious and wanted to experience my first time with a guy. I didn’t know anyone who was gay, so it was ok. Actually it was more than ok - it was amazing! What I did regret later on was being almost raped by a different random guy. Now I would advise my 23 yr old self to wait to find someone you know, trust and like.
 
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phoebusrex

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Mine was with a guy I didn't know at the time. I was 18, logged onto grindr and found an older guy who had a thing for taking the virginity of young guys. I don't regret it at all, it was some of the best sex I've ever had.
 
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deleted2993841

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My first anal experience was with someone from tinder. We ended up dating for a few weeks but he was the jealous type and didn’t trust me. He was older and we lived 100 miles apart, and I was naive. I have zero regrets. He went slowly and once I spoke up about my wants the sex was incredible.

my first oral receiving was on Craigslist. I was nervous and the compatibility wasn’t there. Didn’t finish. Couple years later met someone on a4a did the car thing, he was amazing but we got interrupted.

my first giving oral was on a4a met him in his driveway late at night. He wasn’t thick so I could take him deep. Lessons learned about swallowing too much air during. I thought I was allergic but it was gas. Lol
 
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waka101akaw

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My first time doing anal was with a guy on Grindr. He was a lower batch in college, six inches shorter than me and discreet. I was inexperienced and stupid. I'd only done oral, and at that time, never hooked up with guys I actually found attractive.

This guy was attractive, not conventionally, but he was pretty much my type. Things happened fast and before I knew it, he was picking me up on campus and bringing me to his place.

We did it, I bottomed, I didn't clean beforehand and ended up getting shit on his thing. He was cool about it, we washed up and continued to do it. It felt good. But, then...

I accidentally said "I love this" and I think he thought I said "I love you" and well we still finished, but I could tell I messed up. He was a kind guy, so he still drove me back to campus. We even kissed before I got out of his car.

One day, we passed by each other in the halls. Being completely dumb, and completely attracted to the guy, I called out to him (WHILE HE WAS WITH HIS FRIENDS) and told him to call me. I didn't know that discreet gay hook ups had unspoken rules to never talk about it out in the open. We never spoke again.