Jiffylube851 Posted April 17, 2006 Report Share Posted April 17, 2006 OK sorry this is long but I am kind of down right now. I am 26 and I am a virgin. Well I was, until a few hours ago. I went and saw an escort, I thought it would build my confidence with women. Now that I've kind of come out of my social shell and am meeting girls, I wanted to be more physically confident so I know what I'm doing when I first have sex with a girlfriend. The escort was great, very pretty, friendly, 'built me up', didn't comment on the size of my penis, etc. Classy and great all around. However, I couldn't cum...in fact both in her mouth and vagina I felt basically nothing on my penis (was wearing a condom). She and I went at it for literally 45 min and it didn't even feel good for me. It wasn't impotence, I was rock hard the whole time. My worries are these, 1) Do you think all those years of masturbation damaged my ability to respond to anything but a hand (I was able to cum when she gave me a hand job)? 2) My penis is average length (5.5") but very thin (4" around), do you think part of why I felt nothing was because it was so thin that there was too little friction from the mouth or vagina? I'm really worried here that I won't ever have a normal sex life I mean I guess this is better than the alternative, cumming the minute I put it in...but it wasn't a lot of fun Can you help??? Quote Link to comment Share on other sites More sharing options...
afterglow Posted April 17, 2006 Report Share Posted April 17, 2006 You were probably nervous. It was your first time, and you have insecurities. And when you're nervous, it's hard to relax enough to orgasm. Not to mention that you have no emotional connection to this woman. Many people have a hard time enjoying sex with a stranger. I'm sure there's nothing physically wrong with you. Sounds totally psychological and normal. Quote Link to comment Share on other sites More sharing options...
tallguypns Posted April 17, 2006 Report Share Posted April 17, 2006 I agree with afterglow. And I would like to add that you might contribute to the insecurities by even questioning yourself in this manner. I think far too often we put WAY too much pressure on ourselves and set expectations that are far too high when it comes to sex. There are some people out there that arent capable of having a loving monogamous relationship, but only can go from one night stand to one night stand. Other people get nervous in the bedroom with people they're not very familiar with. Try to ease your own mind. The goodies obviously work if you stay hard and can orgasm. Quote Link to comment Share on other sites More sharing options...
Chosen Posted April 17, 2006 Report Share Posted April 17, 2006 Hello Jiffy and glad you got to be with a female even if she was an escort. I'm a bit curious, how you found a legit escort service and how much was it. 45 minutes? Not bad for a below 5 inch penis. Was it solely intercourse or was four-play provided as well? I hope I feel something sweet and yummy when ever I have the first chance to score. I guess, I would go the escort route first and get her opinion on my performance as well as, have her instruct me on how to properly please a female both orally and thru inter-course. The hand can be wicked at times Jiffy, but the gentlemen that are still virgins must learn to part ways and give the vagina a chance. Quote Link to comment Share on other sites More sharing options...
Ulcaster Posted April 17, 2006 Report Share Posted April 17, 2006 Wow, you got more sack then me. Cheers I've thought about the escort a few times. Obviously, I never went through with it. Hope next time goes better. I see you posted this at T's also. Quote Link to comment Share on other sites More sharing options...
shanenone Posted October 11, 2006 Report Share Posted October 11, 2006 first time for me was a disaster, kept slipping out, but find the right woman and be patient with yourself. it will all fall into place an dyou will be happy... both of you Quote Link to comment Share on other sites More sharing options...
Guest Posted October 20, 2020 Report Share Posted October 20, 2020 On 4/17/2006 at 1:56 AM, Jiffylube851 said: However, I couldn't cum...in fact both in her mouth and vagina I felt basically nothing on my penis (was wearing a condom). She and I went at it for literally 45 min and it didn't even feel good for me. It wasn't impotence, I was rock hard the whole time. Between the condom and "no hand" I can well understand. I've had similar experiences, but lost my hard-on way before 45 minutes. I hate condom sex. Sure glad it wasn't necessary back in "my day." Quote Link to comment Share on other sites More sharing options...
Guest Posted January 15, 2021 Report Share Posted January 15, 2021 On 4/17/2006 at 1:56 AM, Jiffylube851 said: OK sorry this is long but I am kind of down right now. I am 26 and I am a virgin. Well I was, until a few hours ago. I went and saw an escort, I thought it would build my confidence with women. I got over my virginity the same way only slightly younger. Long ago so, condoms weren't a problem. I was so nervous I had trouble staying hard for more than a few moments and, at first, would often cum when still soft or getting soft. She got me comfortable over a few weeks and soon I felt comfortable fucking in various positions, cumming in her mouth and even in her ass. No doubt she was faking orgasms, but, at least I was staying hard for a reasonable time and pleasing myself, feeling like "I was fucking." I should have stopped then, but got too involved with her personally. Quote Link to comment Share on other sites More sharing options...
Guest Posted March 21, 2021 Report Share Posted March 21, 2021 On 4/17/2006 at 4:42 AM, Chosen said: I guess, I would go the escort route first and get her opinion on my performance as well as, have her instruct me on how to properly please a female both orally and thru inter-course. I asked the prostitute finally about my performance and asked her to instruct me how to improve. I broached that she was probably faking orgasms because that's what I had read prostitutes do. I was a bit stunned at how relieved and eager she was to have the conversation. She said she hated faking it. Blaming her profession, she said my penis was too small to satisfy her and she needed oral if I wanted to make her orgasm. Not exactly what I wanted to hear, but I gave no indication of that and I accepted her training in oral. Soon our sex was dominant female face sitting during which I would eventually masturbate to completion. She didn't want to deny me an orgasm exactly, but she wanted it delayed until she was fully satisfied. She didn't deny me penetrative sex, but didn't encourage it either. Soon I didn't ask for penetration often because if was clearly just a resented duty for her. I started to realize I was over-staying that situation. Quote Link to comment Share on other sites More sharing options...
SloStroker Posted March 21, 2021 Report Share Posted March 21, 2021 5 hours ago, wayless said: Soon I didn't ask for penetration often because if was clearly just a resented duty for her. I started to realize I was over-staying that situation. That's how it is with my wife. She will pity fuck me every once in awhile, but she told me my dick was too small and it was "too much work for no reward" Quote Link to comment Share on other sites More sharing options...
Nillywilly Posted March 21, 2021 Report Share Posted March 21, 2021 2 hours ago, SloStroker said: That's how it is with my wife. She will pity fuck me every once in awhile, but she told me my dick was too small and it was "too much work for no reward" Have you ever thought about putting on an extender or a strap-on? I mean, if she wants a “reward”, why not give it to her? Quote Link to comment Share on other sites More sharing options...
JasonBeam Posted March 22, 2021 Report Share Posted March 22, 2021 Why don't you start a new thread, no point in piggybacking on a 14 year old post ... Quote Link to comment Share on other sites More sharing options...
SloStroker Posted March 22, 2021 Report Share Posted March 22, 2021 13 hours ago, Nillywilly said: Have you ever thought about putting on an extender or a strap-on? I mean, if she wants a “reward”, why not give it to her? Yes, I have tried wearing an extender. She said it didn't feel like the real thing. Quote Link to comment Share on other sites More sharing options...
sgdgolf Posted March 22, 2021 Report Share Posted March 22, 2021 My penis also does very little for my wife, but we manage to get her satisfied with extenders, vibrators and oral. It was not easy having that conversation in the beginning, but it is better than both parties frustrated after sex. She agrees it is not quite like the real thing, but it works and gets her an orgasm most of the time. However, she is also allowed to get the real thing elsewhere too and does that from time to time.. Foursquared 1 Quote Link to comment Share on other sites More sharing options...
Guest Posted March 22, 2021 Report Share Posted March 22, 2021 (edited) 14 hours ago, JasonBeam said: Why don't you start a new thread, no point in piggybacking on a 14 year old post ... I'd like to think our discussions are timeless! Edited March 22, 2021 by Guest Quote Link to comment Share on other sites More sharing options...
SloStroker Posted March 23, 2021 Report Share Posted March 23, 2021 22 hours ago, Sven D. said: However, she is also allowed to get the real thing elsewhere too and does that from time to time.. That is so hot! I have begged my wife to fuck other men. Does your wife tell you about her encounters? Ever get to watch? Quote Link to comment Share on other sites More sharing options...
sgdgolf Posted March 23, 2021 Report Share Posted March 23, 2021 Just now, SloStroker said: That is so hot! I have begged my wife to fuck other men. Does your wife tell you about her encounters? Ever get to watch? Well, we started swinging about 10 years ago, so that is how this all started. She usually tells me when she is seeing someone else and occasionally I also get to watch, but this is not for everyone and requires a lot of trust and communication. Quote Link to comment Share on other sites More sharing options...
Guest Posted March 23, 2021 Report Share Posted March 23, 2021 1 hour ago, SloStroker said: That is so hot! I have begged my wife to fuck other men. Does your wife tell you about her encounters? Ever get to watch? I doubt the "so inclined" women I've known would respond to begging. They would want it to be an idea that they imposed. Maybe she really isn't "so inclined." Quote Link to comment Share on other sites More sharing options...
Nillywilly Posted March 23, 2021 Report Share Posted March 23, 2021 @Sven D. You, sir, have iron stones and I salute you! You have to have reserves of self-esteem to be able to watch your wife get off with another man and not feel humiliated. Quote Link to comment Share on other sites More sharing options...
Guest Posted March 23, 2021 Report Share Posted March 23, 2021 20 minutes ago, Nillywilly said: @Sven D. You, sir, have iron stones and I salute you! You have to have reserves of self-esteem to be able to watch your wife get off with another man and not feel humiliated. I wonder? Did he say he felt no humiliation? Maybe he will comment. Quote Link to comment Share on other sites More sharing options...
sgdgolf Posted March 23, 2021 Report Share Posted March 23, 2021 (edited) Just now, wayless said: I wonder? Did he say he felt no humiliation? Maybe he will comment. Well, its a bit of both. It is immensely arousing to see your wife having sex from the third person perspective. She has definitely become my favorite porn star, so to speak. I am extremely happy for her that she gets to enjoy sex so much and do what is forbidden for most. Sex is just one aspect of a relationship, albeit an important one. I would feel worse if she had to sneak behind my back and cheat, just so she can experience this, because as many toys as we use, it does not quite replace the real thing. However, there is also an element of humiliation, because another guy is fucking your wife in front of you and she is enjoying it. So again, I would say not everyone is cut out for it and I would be lying if I said it does not play tricks on your mind. However, lots of trust and communication, a set of rules that do not get broken and a sense of adventure, because we are putting to life some of our fantasies. We have been handling it this way for the last 10 years or so and it works for us. However, we also know plenty of couples in the swinger community who have broken up in the meantime for various reasons. Oh and in case anyone is wondering, no, I do not get to have sex with other women. We tried that in the beginning, but I am just a bit too small endowed to be in high demand in the swinger scene. There are lots of younger, well endowed single guys that the wives would rather try. We tried that with a few couples in the beginning and while my wife would not have a problem with it, the other women were not exactly excited, which led to a lot of one-time meetups. Again, everyone will have a different opinion about this, but this is our relationship and it works for us. Edited March 23, 2021 by Sven D. Nillywilly, Foursquared and 6INCHES66 3 Quote Link to comment Share on other sites More sharing options...
Guest Posted March 23, 2021 Report Share Posted March 23, 2021 (edited) The prostitute I've been mentioning induced me to watch her and her well endowed "fuck buddy" have sex. I felt humble seeing him perform so much better with her than I had, but since she wasn't a girl friend or a wife those feelings weren't all that acute. It was a little acute maybe when she gave so much adoration to his cock as well as orgasming repeatedly from penetration. It was more exciting than porn, but I thought live sex would be. I was naïve about sex back then and didn't realize she was enjoying the thought of "cuckolding" me until later. Edited March 23, 2021 by Guest Quote Link to comment Share on other sites More sharing options...
Nillywilly Posted March 23, 2021 Report Share Posted March 23, 2021 @Sven D. Thank you for your frank and informative post. I think you do have iron stones to follow such a path. You are 52, you look to be youthful and in good shape, do you mind telling us your wife’s age? I would imagine she must be attractive. Are most of her partners younger men? Quote Link to comment Share on other sites More sharing options...
sgdgolf Posted March 23, 2021 Report Share Posted March 23, 2021 Well, we both work out every day. Me vertically at the gym, she mostly horizontal She is 49 and we met in college. I will try to attach a pic to this message. I think she is very attractive and fit. cko01us, Foursquared, 6INCHES66 and 3 others 2 1 3 Quote Link to comment Share on other sites More sharing options...
6INCHES66 Posted March 23, 2021 Report Share Posted March 23, 2021 (edited) You are correct she is most definitely attractive and has a very nice body. You are a lucky man. No offence intended but my penis started to rise to the occasion admiring her pic. Edited March 23, 2021 by 6INCHES66 Nillywilly and Restoredude 1 1 Quote Link to comment Share on other sites More sharing options...
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