Need advice, driving myself crazy.
I'm predicting the advice is going to be "cut it off, move on, wasted enough time" but I'm just going to lay it all out and anyone willing to read everything and give me their perspective I will appreciate.
Let's start from the beginning.
I had some people over at my house to have some drinks, an acquaintance of mine brought over his girlfriend. I found her very attractive and we had some conversation but nothing crazy, considering she was there with her boyfriend. However that night she added me on social media.
About a week later she likes an old picture of mine on Instagram and I shoot her message, turns out her relationship is over with her boyfriend. She suggests we should hang out sometime and I invite her over to my place that very night. I pick her up around 8 and within 20 minutes were both completely naked, and as things start getting hot and heavy she stops and tells me she's a virgin. I don't believe her at first, but I have come to believe her. Her ex-boyfriend also said that they never had sex and she said the same thing. She tells me she has something called "Vaginismus" and I believe her. So basically all that happens that night is I go down on her, she gives me a blowjob, and we did try to have sex but obviously it didn't work. (She squirms a lot and her body basically just makes it very difficult)
We end up hanging out about once a week (occasionally twice) for a couple months, and we always just went down on eachother and that was it. She never let me finger her (super personal but she mentioned her dad fingered her when she was like 8 years old, hes dead now though)
So basically at this point we are in an open relationship where we hookup (no sex) and snap occasionally. The Thursday before last we hung out and she suggested she wanted to try and have sex. I went down on her and made sure she was dripping wet, got her on top so shed be more comfortable, through a condom on and had her try to put it in. We got the tip in but it was hard to go any farther and she was shaking a little bit all over. I could tell it wasn't likely to workout this night and I suggested we mark this off as progress and try again next time. She really liked the idea, thanked me for being patient, sucked me off and I took her home.
The next day she snaps me saying she's really excited to try and have sex again. So we hangout the next day, this time I covered the condom in lube hoping it would make things easier. We may have got it a little farther in but nothing significant. I asked if she'd be down to try without a condom and if it works we can throw it back on, and she's receptive to the idea. Doesn't work still though.
So at this point we've actually been hanging out for three months, and honestly I've put in way to much effort. We have plans to hangout this Thursday and I have some ideas on how to possibly make it work this time. This time after we get hot and heavy and I go down on her, I'm gonna suggest that she fingers herself to help loosen it up (I know she has fingered herself at least a few times before). Then I think I'm gonna ask if she'd let me finger her for a minute to also help loosen it up and just get a feel for it because I think it'd make it easier for me to navigate my dick inside her.
But honestly I'm driving myself crazy over this girl and wasting my time, my plan is to break it off with her if it doesn't work this time. I feel like all the time I've invested has got me really tripping over this girl (thinking about her way to much.. need more girls in my life). Ultimately there's not a whole lot of advice you guys can really give me that I haven't been telling myself and obviously a few paragraphs can't give you guys the full feeling for the dynamic. I have no idea how she feels or what she wants, and most of the time it's really easy to tell with a girl. I think I might just be being played, but I would really love to smash this girl. I know if I could then I'd have much more power in the relationship and I'd be able to relax a little bit, but honestly I think I am just wasting my time. I know the sex won't be great (virgin for christ sake) and I don't think I could really trust her in a relationship. The only reason I've stuck around this long is because she is fun to hangout with, and I tell myself that I want to help her open up and be able to enjoy sex. Everyone deserves to be able to enjoy sex. But I think part of me is digging the idea of taking her virginity.
Anyways, the most productive part of this post is probably me just writing everything out. I don't know what anyone could really say to me that would help, but if any of you out there have some insight that you think will be useful, I'm all ears. Should I keep trying if it doesn't work this next time? Perhaps just enjoy her company, get some good blowjobs while I pursue other girls? Or cut it off because if I don't then I'm not gonna be able to "get over her" and that will make it harder for me to meet other girls.
I'm predicting the advice is going to be "cut it off, move on, wasted enough time" but I'm just going to lay it all out and anyone willing to read everything and give me their perspective I will appreciate.
Let's start from the beginning.
I had some people over at my house to have some drinks, an acquaintance of mine brought over his girlfriend. I found her very attractive and we had some conversation but nothing crazy, considering she was there with her boyfriend. However that night she added me on social media.
About a week later she likes an old picture of mine on Instagram and I shoot her message, turns out her relationship is over with her boyfriend. She suggests we should hang out sometime and I invite her over to my place that very night. I pick her up around 8 and within 20 minutes were both completely naked, and as things start getting hot and heavy she stops and tells me she's a virgin. I don't believe her at first, but I have come to believe her. Her ex-boyfriend also said that they never had sex and she said the same thing. She tells me she has something called "Vaginismus" and I believe her. So basically all that happens that night is I go down on her, she gives me a blowjob, and we did try to have sex but obviously it didn't work. (She squirms a lot and her body basically just makes it very difficult)
We end up hanging out about once a week (occasionally twice) for a couple months, and we always just went down on eachother and that was it. She never let me finger her (super personal but she mentioned her dad fingered her when she was like 8 years old, hes dead now though)
So basically at this point we are in an open relationship where we hookup (no sex) and snap occasionally. The Thursday before last we hung out and she suggested she wanted to try and have sex. I went down on her and made sure she was dripping wet, got her on top so shed be more comfortable, through a condom on and had her try to put it in. We got the tip in but it was hard to go any farther and she was shaking a little bit all over. I could tell it wasn't likely to workout this night and I suggested we mark this off as progress and try again next time. She really liked the idea, thanked me for being patient, sucked me off and I took her home.
The next day she snaps me saying she's really excited to try and have sex again. So we hangout the next day, this time I covered the condom in lube hoping it would make things easier. We may have got it a little farther in but nothing significant. I asked if she'd be down to try without a condom and if it works we can throw it back on, and she's receptive to the idea. Doesn't work still though.
So at this point we've actually been hanging out for three months, and honestly I've put in way to much effort. We have plans to hangout this Thursday and I have some ideas on how to possibly make it work this time. This time after we get hot and heavy and I go down on her, I'm gonna suggest that she fingers herself to help loosen it up (I know she has fingered herself at least a few times before). Then I think I'm gonna ask if she'd let me finger her for a minute to also help loosen it up and just get a feel for it because I think it'd make it easier for me to navigate my dick inside her.
But honestly I'm driving myself crazy over this girl and wasting my time, my plan is to break it off with her if it doesn't work this time. I feel like all the time I've invested has got me really tripping over this girl (thinking about her way to much.. need more girls in my life). Ultimately there's not a whole lot of advice you guys can really give me that I haven't been telling myself and obviously a few paragraphs can't give you guys the full feeling for the dynamic. I have no idea how she feels or what she wants, and most of the time it's really easy to tell with a girl. I think I might just be being played, but I would really love to smash this girl. I know if I could then I'd have much more power in the relationship and I'd be able to relax a little bit, but honestly I think I am just wasting my time. I know the sex won't be great (virgin for christ sake) and I don't think I could really trust her in a relationship. The only reason I've stuck around this long is because she is fun to hangout with, and I tell myself that I want to help her open up and be able to enjoy sex. Everyone deserves to be able to enjoy sex. But I think part of me is digging the idea of taking her virginity.
Anyways, the most productive part of this post is probably me just writing everything out. I don't know what anyone could really say to me that would help, but if any of you out there have some insight that you think will be useful, I'm all ears. Should I keep trying if it doesn't work this next time? Perhaps just enjoy her company, get some good blowjobs while I pursue other girls? Or cut it off because if I don't then I'm not gonna be able to "get over her" and that will make it harder for me to meet other girls.
