So a part time gig I've had on and off the last few years has been driving escorts and/or strippers to work. When its been busy its been good for a few extra bucks a week which comes in handy and an added benefit is that they usually have some hot stripper/escort friends who want to party.
Anyhow in the last 6-8 months I've only been driving for this one very attractive 21-year old WOC stripper with a sick body and we've gotten quite close. Even though she can be difficult sometimes and is immature we have a connection. We had sex once when we went to AC back in the summer and since then have fooled around several times (she jerked me off or blew me in the car a few times) but its only when she's really drunk and now its been several months since we've done anything substantially sexually. If I had my own place it would be different but I haven't been able to afford another AC trip with her since the summer. There's definitely an attraction btwn us but she is the type that even though she's a little slut she has all these boundries in her head about why she doesn't want to have sex with me anymore--- she feels weird about doing it with her driver, she feels weird because I'm not divorced yet, she feels weird because she is paying me to drive her, she feels weird because we are good friends, etc...... I know all this because she's told me.
Well to cut to the chase there is a cute brazillian stripper she works with and her boyfriend who we've become friends with and have gone out a few times after they get done working at their SC in Jersey. We go back to their place and play, basically get drunk start feeling/touching each other and have a good time but it hasn't turned into full-blown sex. Yet.
The other night we hung out again at their place and it got pretty steamy with the gals giving us practically nude lapdances, a lot of touching, feeling each other up, etc. The couple starts almost having sex right in front of us and tells us they are swingers. The only reason it didn't go further was because we ran out of alcohol and our gals got sober quickly. Like I said "my" gal only seems to want to fool around with me when she is very drunk. When she is not drunk she can be a killjoy. Whatever. I'm not crushed by that I just want to bang her again.
So my "dilemma" is basically two-fold:
1) I'm kind of an old-school kind of guy believe it or not and feel kind of weird about having sex with another couple right next to us on the couch or bed. Being naked in front of them, stuff like that. Plus I'm a little self-concious in case his cock is bigger than mine to be honest.
2) I know our stripper's boyfriend wants to bang "my" gal and he wants me to bang his gal. They are swingers after all. But I have only banged "my" gal once and that was only for a minute or two anallly. She said it hurt. Like I said she has a lot of issues in her head lol. But we have done everything else except fuck. Even though his gal is hot I think I'd feel better about him fucking "my" gal if I'd have fucked her a bunch more times. I'm probably just self conscious about my gal liking him more in the sack I guess.
I guess what I'm looking for is comments from people who have a lot of experience with group sex and how to handle it if you're not really an exhibitionist at heart. I obviously have feelings for my stripper friend and even though it would never work out between us I just think it might be weird for me to see her having sex with another guy in front of me even though I'd be doing the other hot stripper. As I said I'm kind of old-fashioned. Plus I get the feeling that this is the only kind of way that I'd get her to have sex with me short of taking her away on an expensive weekend somewhere. I'd love anyone's thoughts/suggestions/advice on how to handle this situation.
Anyhow in the last 6-8 months I've only been driving for this one very attractive 21-year old WOC stripper with a sick body and we've gotten quite close. Even though she can be difficult sometimes and is immature we have a connection. We had sex once when we went to AC back in the summer and since then have fooled around several times (she jerked me off or blew me in the car a few times) but its only when she's really drunk and now its been several months since we've done anything substantially sexually. If I had my own place it would be different but I haven't been able to afford another AC trip with her since the summer. There's definitely an attraction btwn us but she is the type that even though she's a little slut she has all these boundries in her head about why she doesn't want to have sex with me anymore--- she feels weird about doing it with her driver, she feels weird because I'm not divorced yet, she feels weird because she is paying me to drive her, she feels weird because we are good friends, etc...... I know all this because she's told me.
Well to cut to the chase there is a cute brazillian stripper she works with and her boyfriend who we've become friends with and have gone out a few times after they get done working at their SC in Jersey. We go back to their place and play, basically get drunk start feeling/touching each other and have a good time but it hasn't turned into full-blown sex. Yet.
The other night we hung out again at their place and it got pretty steamy with the gals giving us practically nude lapdances, a lot of touching, feeling each other up, etc. The couple starts almost having sex right in front of us and tells us they are swingers. The only reason it didn't go further was because we ran out of alcohol and our gals got sober quickly. Like I said "my" gal only seems to want to fool around with me when she is very drunk. When she is not drunk she can be a killjoy. Whatever. I'm not crushed by that I just want to bang her again.
So my "dilemma" is basically two-fold:
1) I'm kind of an old-school kind of guy believe it or not and feel kind of weird about having sex with another couple right next to us on the couch or bed. Being naked in front of them, stuff like that. Plus I'm a little self-concious in case his cock is bigger than mine to be honest.
2) I know our stripper's boyfriend wants to bang "my" gal and he wants me to bang his gal. They are swingers after all. But I have only banged "my" gal once and that was only for a minute or two anallly. She said it hurt. Like I said she has a lot of issues in her head lol. But we have done everything else except fuck. Even though his gal is hot I think I'd feel better about him fucking "my" gal if I'd have fucked her a bunch more times. I'm probably just self conscious about my gal liking him more in the sack I guess.
I guess what I'm looking for is comments from people who have a lot of experience with group sex and how to handle it if you're not really an exhibitionist at heart. I obviously have feelings for my stripper friend and even though it would never work out between us I just think it might be weird for me to see her having sex with another guy in front of me even though I'd be doing the other hot stripper. As I said I'm kind of old-fashioned. Plus I get the feeling that this is the only kind of way that I'd get her to have sex with me short of taking her away on an expensive weekend somewhere. I'd love anyone's thoughts/suggestions/advice on how to handle this situation.
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