Years ago I worked at a restaurant. I was a cook so naturally I had my run at most the waitresses that came through. This one new waitress was particularly hot and I had my sights set on her.
We chatted here and there throughout the days we worked together. I was a bit more flirty than she was. She was in college and I never went so I just assumed she thought I was a bum. That being said I basically said ‘fuck it’ I’m just going to flirt with her until I get a hint or cue or told to back off. To my surprise I received the opposite.
We made plans to hang out at her place while her parents and brother were gone. I show up and she invites me in. Its always nice to see someone you thought was sexy in a waitress uniform in their actual clothes. They just glow more and are so much more attractive. She brings me up stairs to her bedroom to “hang out”.
I am not one to waste too much time. I leaned in and started kissing her. She wasn’t the best but, she wasn’t the worst. I just figured she was nervous a little. That’s fine. I said we can take it slow if she wants and she just told me to keep going. So I lay her down and start to strip her. Kissing her body, licking her everywhere. I ate her pussy for a solid 10 minutes or so. She whimpered and moaned a little but, not overly enthusiastic. Meh ok, some women are like that, that’s fine.
I lay down and let her go down on me. It was not good. I don’t like to speak ill of peoples sexual skills because that’s just rude but. I figured, hot college girl, she must have had some hookups. She’s blowing me like she has never done this before. huh… Anyway.
I pull a condom out and strap it on. I spit on my fingers and get the head wet then rub the rest across her pussy. She is soaking wet already which was nice to see because up until now it didn’t really seem like she was really enjoying herself. I asked her if she was ok and she said yes. Told me to do it. So, i did it.
Now because I was in my head about ‘is this girl into this? Do i suck in bed suddenly? wtf is happening’ combined with wearing a condom, my body was in rush to cum. So I slipped in it, mm nice and tight, and started off slow. I let her feel every inch before I started going harder and faster. I am mentally keeping up with imaginary college guys who I assumed went to pound town on her already.
So I’m slugging away at her pussy. Rubbing her clit, touching her body, pulling out any and all tricks I got. She just looks like she is holding her breathe and concentrating. I back off and go easier. Same face, and not a lot of breathing. So I close my eyes and imagine whatever I got to to cum as quick as I can. I am feelin like a fuckin failure.
I roll over, pull the condom off and tie the end. I throw my clothes back on as she does the same. Just then we hear the front door open. Her brother. Older brother. He yells up asking whos car is in front of the house. She hides me in the closet in a panic. She goes down and says not anyone for her, nobody else is home. She comes back up and says to follow her quietly.
So as we get to the door and I am running out to get to my car, he sees me. I get in and start driving just as he comes out with a bat, chasing my car down the street. Fuck me that was close.
A couple days later we are texting and I apologize for not being very good and that I’m sure she’s had much better. She responded with “I have something to tell you……. I was a virgin.” WHAAAAAT. I felt AWFUL. Here I am smashing this girl like she owes me money and she was a virgin! I apologized profusely and said I wish I had known! She was afraid I wouldn’t hook up with her if I knew but I still would have I just would have went about the whole situation much much more gentle. *sigh* But, she said she was ok, it wasnt terrible, and apologized for her brother. She quit a couple weeks later.
Source: reddit.com/r/gonewildstories/comments/ed0c8q/mf_i_didnt_know_she_was_a_virgin_oops
That is such….a Big Yikes™