How bad was your first time? (Mini-TR included)

[toohigh]

So my first time was like 2.5 yrs ago, and god was it awful. This thread doesn't make me feel too bad about it, but it still was a horrifying experience for me.

I had met this chick like 2 or 3 weeks before I closed the deal. I was at a strip club with the guys I was working with at a radio station. Our show had just got canceled, so we decided to hit up a strip club to take out our frustration.

The strippers were alright, but this one cocktail waitress was smoking. We chatted up for a bit, and I guess the fact that I was out of a job and drunk made me fearless, as I got her number and was spitting game to her like I was an expert PUA. Truth be told I still have ZERO game, but whatev.

So anyway, a couple of nights later, another DJ from the radio station I was working at wanted to set up a get-together on my dad's boat. Turns out he knew the cocktail waitress that I had met the other night (don't really remember if this was some strange coincidence or what, but looking back, the ho prollay just got around), and brought her along with some other peeps. When we recognized each other, the attraction level skyrocketed, and we were hooking up pretty much all night. Started off in the parents' bedroom of the boat, then continued in my car while we all went to some other strip club that night. No sex yet, but some serious making out/groping/dry-humping was going on. This was enough for me at the time, too, b/c I hadn't even hooked up with a chick before to the extent I was with this one. I was still totally clueless.

Things continued in a similar fashion, with a little bit of tension between us because she was 26 and I was 21 (didn't bother me but she kept bringing it up that we couldn't be serious b/c of this), until the day she took my virginity. We went out to some club to celebrate my birthday which was a few days passed. We all got trashed and had a pretty sweet time from what I remember. Then we head back to the boat at like 3am. Here was where the first problem happened on my sex-quest. Cocktail waitress had this step-brother, who was basically the world's biggest mooch. Totally dependent on her, and would basically tag along with her everywhere. Well this night was no different, so while I'm getting things going with cocktail waitress back in the bedroom on the boat, this guy barges in at least twice, complaining that he wanted to borrow my car so he could go home and pass out. F that, I'm not letting some random, drunk [censored] drive my car over 30 minutes. Cocktail waitress and I try to ignore him, and she keeps complaining about what a pain in the ass he is, probably cuz he was the only person not getting any out of everyone we were with that night. Just totally awkward all around.

The next problem occurred for me during the act. Like many others in this thread, I just couldn't really get my mojo going, and was all but limp for 90% of the entire experience. This was caused by my complete amateur status when it comes to sexytime, severe performance anxiety, combined with being pretty drunk and really stoned, and still steaming from her step-bro barging in every 5 minutes. My mind at this point is racing in a million different directions, part of me completely stoked that I'm finally sexing, and with a hot, hot, hot chick, and the rest of me just completely confused and frustrated. When I finally got it going, I was doing her missionary, and the [censored] bitch says "I want you to come inside of me, be a daddy!" over and over (she already had 2 kids, lol). Ughhh, this really ruined the mood for me, but I was determined to at least get off somewhere on her body, just not inside.

We try every position, [censored] I couldn't even get it in doggy style cuz it was too limp. It was just a complete disaster. Half the time I had a condom on, which really shrinked my package, and it slipped off like twice, so we were both like "F it" and I just rawdogged it the rest of the way. We even took a break, and I called the captain of the boat at like 8am to take us all for a ride. During the ride, we went back down to the bedroom to try again, and she was riding me while the boat was getting bumpy cuz of all the waves, and she was enjoying it thoroughly, but I still couldn't finish. ARGGH, so annoying.

Eventually I guess we just gave up, I remember her saying something like "you must not want me" and me just laying face down in the bed with my head buried in a pillow cuz I was so ashamed.

And to make the whole experience even more [censored], I got a [censored] staph infection (that's what the dermatologist called it) from the dirty ho on my groin area. Thank god it wasn't teh herp, but it still hurt like hell and was just gross and took like a month to go away. Talk about running bad at sex...

This experience left me with absolutely zero confidence with women, and still haunts me til this day. Thankfully, the one positive I did learn from this was not to blow crazy amounts of money on chicks (I spent like 2-3k with this girl between me buying her stuff, going to see her where she worked and blowing mad money there, and taking her out to clubs and dinners). Now I am stuck with a mentality of being as cheap as possible when it comes to women, where I feel like it's not my lack of confidence that has been hurting my game, but the fact that I simply would rather save my money than spend it on a chick.

[Fast Food Knight]

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TR from the person who rated their first time a 10, plz.

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He was 5 years older. It was good.

[makelovenotwar]

My first time was at 18 and the only beat I can remember other than paying for the whole thing is that I can't even remember her name or guesstimate the age of the woman.

But lets start at the beginning. Could have sexed a couple of girls at high school but the girls that wanted to hook up with me where always in my own league ( meaning, 4-6, on a 10 max scale ). Naturally, at the time I was much more attracted by the smoking hot 9-10s at my school which unexplicably never had any interest in me.

So no action during high school. Then it occured to me that it would be useful to gather some sexual experience prior to starting uni in order to avoid all the first time problems so many of you have described. Looked around on the internet and found a number of an oriental massage parlour nearby. Called a cab and went there, fully expecting to be robbed and sliced up for the international kidney trade of the chinese mafia. lol, no such thing. Was given a choice between two girls. One youngish with no breasts and very bad teeth and one older woman who fronted some b-cup titties. well the choice was easy and I went for the older broad. With asian women I can never tell and she could have been anything from 25-45 years old. Went to the room, forked over the monies and off we went. She wanted to start off with some massage and powder my back with some awful "talc powder". screw that lets get on with the real business. So she started blowing me and after a couple of minutes my tool started functioning and off we went into mish position. I think I gave it a good 10-15 thrusts before finishing.

All I could think of was " so this is what you've been waiting for all those years". Kinda unspectecular. I even laughed and joked about it with the asian girl. One thing I gotta say though, in terms of "safe sex" you couldnt have a better time than with an escort. after all they have all the experience in the world =)

[CletusVanDamme]

Freshman year of college, we head to a bar for a massive keg party. It was a rather large bar, and to this day, I've never seen a bar this crowded.
After a few hours of $.25 draft beer and dancing with a few girls from my hometown, I decide I need to take a seat. Buddy and I sit at the bar, next to 2 girls he knew. Turns out they lived in our dorm.
One looked pretty good, probably a 7, the other, eh, not so much. She was maybe a 4, but I was convinced she was a lesbian, so, for a lesbian, I'd give her a 6.
Lesbian is buying us drinks at the bar, and then starts hitting on me (so much for being a lesbo), but I'm hitting on her friend.
We all get drunk, catch the trolley back to the dorms. Faux-lesbo gets into her bed and passes out. Her friend and I get into her bed and start making out.
I guess we were being loud, because faux-lesbo wakes up and asks "what's going on?" Now, I'm thinking about making my first time a threesome, so I tell her to come over and find out.
I guess that didn't appeal to her, because she leaned over a puked in her trashcan. She probably had the heaves for another 30 minutes or so.
I tell her friend that I need the radio on or something, so she offers to put in a CD, since she can't pick up a radio station in her dorm room. Unfortunately, my choices are "Phantom of the Opera" and "The Little Mermaid". I pick the Disney soundtrack.
Girl was on the rag, and this really freaked me out. We didn't use a condom, and it took me maybe 10 minutes to finish.
IMMEDIATELY after I'm done, I roll off of her, get dressed and tell her I'm sleeping in my room. She looks kind of hurt, but the idea of her menstruating on my junk is giving me too much anxiety.
I get back to my room, take a long shower, and never see the girl again.

[cardcore]

My first time was at a party of a very good friend of mine.

We all got drunk and stoned, had a grillparty and then this girl (I dont even know her name anymore) made out with my friend. Unfortunately I don't know the whole story anymore but somehow me, my friend, the girl and another girl ended up in his room and Girl 1 starts taking off her clothes, I'm superhorny and ask Girl 2 to stay, but she leaves with the words "no way I'm doing that but have fun".

So there we are... 1 Girl, 2 Boys - bad situation.
We are fingering here, she gives us head (with too much teeth as far as I remember) and then my friend says to me that I can go first because it's my first time. I'm still thankful for this [img]/images/graemlins/smile.gif[/img]

I [censored] her in every position I've learned from the big porn-compilation on my pc for about 40 Minutes... alcohol helps... My friend masturbated to Monster Trucks on Television lol.

early in the morning we basically kicked her out of the house and went back to sleep. The next weeks we worried about AIDS because we didn't use a condom and obv she's a whore.

I rate it 7/10.

[Boris]

cardcore takes the lead.

[traz]

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cardcore's story creeps me out

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[AE6]

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But lets start at the beginning. Could have sexed a couple of girls at high school but the girls that wanted to hook up with me where always in my own league ( meaning, 4-6, on a 10 max scale ). Naturally, at the time I was much more attracted by the smoking hot 9-10s at my school which unexplicably never had any interest in me.


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lol women are things, amirite?

[scott1]

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cardcore takes the lead.

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I was hoping for a twist ending, like "We've been married for 12 years now".

[SoloAJ]

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My friend masturbated to Monster Trucks on Television lol.

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cardcore,

You might consider new friends. What a weird weird story that is.

FFK,

Your story has potential to creep me out depending on how old you were. I mean, you weren't like 14 right?