Anyone else lose there virginity to a strapon?

[slaveboi]

I moved out at 18 and got a job working fast food. The assistant manager was my age and was in a relationship with a guy that was older and thinking he might be gay. The manager and I became good friends and spent a ton of time together.  She was very flirty and very sexual. One night we were all watching a movie and she was teasing us. She dared me to suck her boyfriends cock so there i am on my knees loving it. We all stayed friends but he got into a serious relationship with a guy. She pretty much moved into my place but we never did anything sexual.  One day a few weeks before my bday we went to the toy store and she bought a pretty large dildo. I just thought she was missing her bf and didn't think much about it. A few weeks later on my birthday sh makes me dinner and a cake. We have a bottle of southern comfort and strat watching porn. At this point I'm a total virgin and really horny. Eventually we are watching some gay bdsm porn and I'm about to bust out of my pants. She leads me into the bedroom and ties my hands and blindfolds me. I'm thinking she wants to have sex and I'm so horny I was ready to do it. Next thing I know she pushes me down on the bed and I feel something one my hole. She tells me she knows what I really want and just relax.  A lot of lube and shoving later she was fucking my ass. It hurt like hell but she came 2 times.

[TomOnHisKnees]

33 minutes ago, slaveboi said:

I moved out at 18 and got a job working fast food. The assistant manager was my age and was in a relationship with a guy that was older and thinking he might be gay. The manager and I became good friends and spent a ton of time together.  She was very flirty and very sexual. One night we were all watching a movie and she was teasing us. She dared me to suck her boyfriends cock so there i am on my knees loving it. We all stayed friends but he got into a serious relationship with a guy. She pretty much moved into my place but we never did anything sexual.  One day a few weeks before my bday we went to the toy store and she bought a pretty large dildo. I just thought she was missing her bf and didn't think much about it. A few weeks later on my birthday sh makes me dinner and a cake. We have a bottle of southern comfort and strat watching porn. At this point I'm a total virgin and really horny. Eventually we are watching some gay bdsm porn and I'm about to bust out of my pants. She leads me into the bedroom and ties my hands and blindfolds me. I'm thinking she wants to have sex and I'm so horny I was ready to do it. Next thing I know she pushes me down on the bed and I feel something one my hole. She tells me she knows what I really want and just relax.  A lot of lube and shoving later she was fucking my ass. It hurt like hell but she came 2 times.

My first time was with a real cock but my wife has pegged me quite a few times.

[Heir2012]

I might sound dumb, but is that losing your virginity? I guess someone else is doing it, so that makes sense, but I just never thought of it that way. Hmmmm. Interesting thing to think about. 

[Sfmike64]

Of course. Define sex broadly and you'll have more of it. Define cheating narrowly and you'll get cheated on less often (this is way more of a problem with straight people thinking flirting is 'cheating').

[TaKinGDeePanal]

On 6/18/2024 at 11:21 PM, slaveboi said:

I moved out at 18 and got a job working fast food. The assistant manager was my age and was in a relationship with a guy that was older and thinking he might be gay. The manager and I became good friends and spent a ton of time together.  She was very flirty and very sexual. One night we were all watching a movie and she was teasing us. She dared me to suck her boyfriends cock so there i am on my knees loving it. We all stayed friends but he got into a serious relationship with a guy. She pretty much moved into my place but we never did anything sexual.  One day a few weeks before my bday we went to the toy store and she bought a pretty large dildo. I just thought she was missing her bf and didn't think much about it. A few weeks later on my birthday sh makes me dinner and a cake. We have a bottle of southern comfort and strat watching porn. At this point I'm a total virgin and really horny. Eventually we are watching some gay bdsm porn and I'm about to bust out of my pants. She leads me into the bedroom and ties my hands and blindfolds me. I'm thinking she wants to have sex and I'm so horny I was ready to do it. Next thing I know she pushes me down on the bed and I feel something one my hole. She tells me she knows what I really want and just relax.  A lot of lube and shoving later she was fucking my ass. It hurt like hell but she came 2 times.

My anal virginity? Yes. Dominatrix. Virginity itself? That ship had sailed when I was 19. Did you get to fuck her at all, BTW?