11 years ago, I was working at a small grocer next to a sandwich place. I went into the sandwich place one day and the usual girl at the register asked me out for drinks out of the blue. I was so nervous because this was the first time I was gonna go on a date. We went out for drinks and I had too much too fast and we ended up at her place. We sat on her couch for a bit until she asked me if I wanted to go to bed since I had had a lot of drinks. We get into her bed and I sober up immediately, and start shaking with fear. This girl was experienced and had a bunch of tattoos and I had never even held hands before. Anyway, I couldn’t get hard no matter how hard I tried and she just kept looking at me like I was so pathetic. She ended up going to bed with her back to me and masturbating. I could tell she was very angry. In the morning she didn’t say anything but asked if I wanted to hang out again. This happened a few more times but we’d always just go to bed. I never even touched her. I started paying her bills because for some reason I thought I now had a girlfriend. After 2 weeks of this, I found out from her roommates that she got back with her ex. I still kept paying her bills while she had sex with her ex boyfriend in her bedroom while I was hanging out in the living room. Eventually she totally starting ignoring me so I stopped contacting her.

A few months later, I started a new job and was struck by this one girl that worked there. She was a redhead and really hot, I knew I had no chance. We went to a work night out and that night we both had a lot of drinks and I went home with her. The whole night I kept mentioning my “ex-girlfriend” and how she “cheated” on me and stuff like that so she’d think I wasn’t a loser and had a girlfriend in the past. We ended up in her bedroom again and, once again, I was so nervous that I couldn’t get an erection. She put her hand on my chest and noticed that my heart was beating hard and asked if I was ok. I said I was just had too many drinks and we went to bed. The next morning, we woke up and she told me that she realized I was a virgin because I was so nervous. I admitted that I was and she kinda laughed. Anyway…the same thing happened where we would hang out and that was it.

I had the bright idea to text the first girl to get drinks with my new “girlfriend” We were all at the bar and my second “ex” asked my first “ex” about how it was like dating me. The first “ex” just laughed so hard and said we never really dated nor kissed or anything. I ended up just leaving because they started to laugh at me so hard. I think she told at least a few people at work because they def started acting different around me after that.

Those are my only two opportunities I’ve had in my life to lose my virginity and I failed miserably both times. I constantly goon to both of their instas, like almost everyday. I recently ran into the second ex with her new boyfriend and she gave me a hug (one of the few I’ve ever gotten) I was blushing so hard before the hug but as it started, I noticed I spurted in my pants. I thought it was pee, but no, I went to the bathroom and it was a dribble of cum.