drunkenmonkey in Trinidad is doing 19 things including…

lose my virginity


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drunkenmonkey has written 2 entries about this goal

Yeah, not what I expected.(this post is explicit)

Well, what can I say. Been working as a bartender, girl came into the bar. She ordered a bunch of shots and flirted with me all night. We ended up in a dark corner and I got her number and kissed her. She left. I texted her, ended up at her house at 3am. I told her I was a virgin and it freaked her out just a little bit(she wasn’t sure if I was lying, and if I was lying-what I might be trying to pull). She got over it. Then came the weird part.
I figured my first time would be really quick. So I bought these Trojan condoms that have something that kind of numbs you so you last longer. I tried them out getting myself off and it seemed like I came even quicker. They were all I had though so I took them with me when I went to her place.
Turns out, I couldn’t cum. Well…if she had gone down on me without the condom I think eventually I would have cum. But after about three times making her cum with my cock, and a couple more in between with my mouth/fingers, she was exhausted and I hadn’t cum at all. Still…I think making her cum that many times was actually more important to me than my own orgasm. And for what it was worth I had a damn good time.
Afterwards, she told me she had a boyfriend who lived in her home country. I guess that’s kind of fucked up, to have your first time with someone else’s girlfriend. But oh well, I don’t know the guy, and he’ll hopefully never find out.
In conclusion, I don’t think everyone should go about losing their virginity this way, but for a 33 year old virgin like myself, it just needed to happen one way or another. I was just ready, and i don’t regret it one bit right now. It was a lot of fuckin fun, and if I die tomorrow at least I won’t die a frickin virgin:) Hopefully, I have lots of time to find someone special to “make love” to, and not just have sex. But now I have more confidence and I think it will be easier to put myself out there and find that someone.

it's pretty sad, really

I am going to be thirty this fall! I feel like I’m waking up from sleepwalking for close to a decade. I am a good-looking guy, no model or anything. I sing quite well, been on tours internationally. I’ve watched many a girl melt in front of me while I sang. This is not to brag, but actually quite the opposite. I think it makes me a bigger idiot for never having the balls to ask them out. I don’t know where I got this paralysing fear of rejection from. Anyway, its got to stop, cuz I’m going to go insane from desire.


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