Dear Susan

Recently I have been seeing a girl who is 6-7 years older than me. This is quite different but potentially very important for me. We have been out on a couple of dates and had some amazing times so far. I even stayed over at her house on our second date, but that was more from necessity from a night on the town (we only just kind of kissed, cuddled and slept). We have not been overly physical yet on our first couple of dates. We are very in tune intellectually/emotionally so this is no one night stand sexual encounter type thing. It is wonderful to be with her. On this particular night we went out and then came back to her place, talked for awhile, then moved to the bedroom. We were back in her room kissing and talking romantic and such. As typical, I fooled around and then went into protector/cuddle mode instead of horny male exploration mode. My libido/testosterone was definitely not rolling. The problem is I think I'm just kind of a sissy when it comes to taking the next step. Let me explain my circumstance:

I always get to the point with a girl, that I can lead them up to a certain point where, you know our shirts are off and they are gaining my trust and getting hot, etc. etc. and then I just sort of stop. I somehow have this ingrained feeling in my head that I shouldn't go below the belt or any further.

In the instances that I have, I really didn't know what I was doing and grew a bit uncomfortable feeling around down there and stopped. On the flip-side when a girl has a hold of me below the belt strange things happen. With one girl I told her that I kissed her friend that night, so she would stop giving me a handjob. Once I even prematurely ejaculated before with an older woman who wanted intercourse very badly (I had been heavy drinking, but nonetheless) and I stopped sex right before penetration w/ someone else b/c I morally decided that the girl was a tramp and I didn’t want her to be my first sexual experience, so I lost my erection (again, heavy drinking). I’m glad I didn’t have sex with her. I think.

Normally, when a girl starts grabbing my crotch I become uncomfortable for a variety of reasons: I talk myself out of arousal, I become somehow worried about my size or erection, what will she think, where is this going, etc. It becomes unbearably stressful and I want out of the situation. I simply cannot enjoy new things past my comfortable established limit, yet. The episodes don't end necessarily bad or awkward (well sometimes they do, but using alcohol as an excuse has been my easiest out so far), just incomplete experiences for both parties. Soon after, I become disinterested with the girl and we break up. WHAT THE HELL IS WRONG WITH ME?

I know I am overthinking everything. I think about not performing, taking advantage of the girl, being found out as a virgin, my reputation, underperforming, premature ejaculation, morality, pregnancy, blahh, blahh etc. etc. etc. Maybe it had to do with growing up in a Puritanical type of house with two sisters and sexually repressive parents and no brothers. I have been hit with “No SEX Before Marriage” quite often. I attribute my peculiarities with women, my penis, my libido, and other things with my upbringing. I even went to a conservative college where sex was a bit taboo. Girls were lumped into promiscuous (curiously, mostly virgins in this crowd) and what I call the ‘you can kiss me but don’t touch me’ (a.k.a - the crowd who isn’t messing around). I had some fun, but WHO KNOWS where all of my trials are originating? More info……

Some particulars.....I'm 23, very healthy, attractive, have a nice penis (maybe a bit small to just look at normally, but it grows to quite a nice length/girth), and I am becoming progressively more liberal minded towards sex. The problem is from frequency of girls I have been with there is an assumed (in all reality - quite false) lengthy sexual history. I find this humorous and let it endure, but this is not the case. Girls and friends just think I dump girls b/c I’m not interested or they won’t go further type scenarios. I proclaim a somewhat truthful lack of interest in the girls, which fittingly explains the end of relationships.

The truth I guess at this point is that I am afraid of sex, the vagina, and my own penis. Masturbation is fine for me and I get very turned on viewing pornography with just women and between a woman and a man. I am highly stimulated by the thought of a woman giving me oral sex. I would love to be great at sex but maybe I am too private, selfish, self-consumed to really pursue further experience? I just grew up thinking that having sex with a woman or doing sexually things between a man and a woman was dirty or taboo. As you can tell from my writing, I am clearly conflicted. I have a good sense of humor but cannot take criticism very well. I’m working on that. Maybe I should consider my predicament comical, stop being so serious, and make a few mistakes on my way to sexual enlightenment.

Help Me Please Alice! I was with my new older girl a couple of days ago and we got to the point where she said as it got late (clothes on mind you): "Are we going to do more." I turned it up a notch, got her hot, and then I of course made my early exit. Damn me for not being able to get over myself or take the next step. I’m am literally afraid that a finger would go in the wrong place, I would ejaculate on touch, just basically that I might make a blunder that would haunt me for life. I'm an affable guy, but I think I am taking everything far too seriously in the sex/foreplay category. She has lived with a guy previously so, although she is quiet, I would have to assume she is experienced in sex and romance. We haven’t spoken about sex, but we are at that critical moment where I know she thinks I’m building the anticipation, which I think is generally happening. I am going to see her Saturday at a party she is throwing and would like to make some headway. Do I get her to lead the way for me? I would love for her to teach me a few things. She is a med school student and quite older than me, so anatomically speaking she knows a thing or two. I’m becoming gradually more open to the idea of experimenting with sex. I just have to gain someone's trust and buck my suppression of my sexuality. That's all for now. Any advice would be appreciated. Thanks.

Desperate For Some Serious Meaningful Action

OK, this may seem like a really weird suggestion - but stick with me. You need to put either an ad online, in the newspaper, or hire a prostitute.

If you go with the ad.......

Looking for a one-night stand to teach me the ways of the world. I am a virgin and I need to be with a women who will take charge, be gentle, and teach me everything I need to know.

Part of your problem is your fear of failure. You make a really good connection to a women - and then the risk of failure is too great. You need to be with a woman who you are going to have sex with - forget about whether she is your type, she is pretty , is your age, is someone you want to have a conversation with--the idea is sex. Sex for the sake of sex. Get it over the first time so you can stop being so worried about it.

THen I am bet you will be far more relaxed about sex and this current woman who sounds terrifc will be a great woman to have your first meaningful sex with.

Susan

As I was reading through your post Richard, on how you are able to be with a girl but you're unable to go all the way and have sex with her, it really made me realize how similar your and my situation are. I too am a bit afraid of having sex and like you, I am a 23 year old male virgin. I understand exactly what you're going through.

Some might say guys like us are somewhat pathetic or possibly gay, but I don't think we are. With all the STD's out there you just never know who is infected and who is clean. It's probably for the best that you chose not to have sex with the tramp girl, since she has probably been with many guys.

You also mentioned that you like to overthink situations. I like to over-analyze situations too, but doing this can drive yourself crazy. Sometimes, it is best just to relax and not overthink to the point of insanity. Another striking similarity between us is that you also have two sisters and no brothers (like me) and your parents probably never talked about sex until you get married.

I also view sex on a whole as quite taboo and dirty in a way. But unlike me, you're in a decent relationship with an older med-student who you can experiment with. I don't agree with Susan's advise of taking out a classified add just for the purpose of meeting a hooker and having sex with her. I mean, it will be your first time and it should be special.

The next time you and your girlfriend get together talk with her and explain to her that you are inexperienced in sex and she could lead you through it, as she probably has more experience. Hope that helps.

Clay could be right - and what he expressed was my first thought. But I have been in the shoes of your currently female friend more than once. This could be my own experience and not apply to her, but I found that after the teaching sex lesson was over - it forever changed the way we related to each other and we could no longer be in a peer relationship. I was the teacher - he was the student.

So if you want this woman to be your teacher and not your lover - than ask her to be your teacher. But if you really like this woman and think you might have a future with each other- I think you take some big risks.

I've never been with a man I was less experienced and knowledgeable than - but the successful sexual relationships have ALWAYS been with men who are extremely self-assured, even cocky on the verge of obnoxiousness - you don't sound like that nor does she.

Susan

Hello. Okay, great advice thus far. While hiring a prostitute or placing an ad in the papers is out of the question, I did find that very humorous. Cheers.

Let me ask a few more things. Give me some good ways in general to get the lines of conversation open between Sharon and I in regards to fooling around/experimenting/potentially having sex. I know I have the potential to be a great lover but will inevitably need to be coached some along the way. I do however make progress quickly. Sharon is a bit quiet like I said before, but brilliant and knowledgeable, so alot of the conversation is up to me. We have a great time and I am by no means clingy or needy, so I know she views me as this funny/cocky/wild-card kinda guy.

This being prefaced, I don't yet know what she is comfortable with sexually, or what she is happy speaking about. I just don't yet know. Give me some steps to try out with her to get things going where we can speak frankly on the topic. How do you speak about 'putting your hand there, doing this faster, etc.' in a funny, conversationally pleasurable type of way. Even something liking fingering her, how do I do this in a way that will maximize pleasure for her. I'm really unskilled with things below the belt like I said before in my post. I'd like to say something like "what do you like," "show me" or something like that. Since I don't care to posture, I'd like the conversation lines to be as open as possible.

I'll leave it at that for the moment. I'm going to see her later tonight and would like to make some progress. And, if this relationship falls through, so be it. I'm a great guy too, you know, just a bit naive. I'm confident in pretty much everything except for what I'm writing about. I see it as, "at least at this point I'm willing to admit my shortcomings and am trying to finish off my basic sexual learning curve." I would like to make Sharon happy though, so give me some more specific advice/things to try out/ways to phrase sexual advances/ease tensions/etc. This means a great deal to me.

You guys are a great Resource!

Richard

Have you checked out my quiz? http://www.sexsupport.org/sexqa.html

Maybe using the quiz- actually filling it out together will give you some place to start from. Since you are both older a lot of the questions will seem a bit silly - but they are all question people need to discuss before they have sex.

There are some wonderful educational sex videos available that are not pornography that are produced by the Sinclair Intimacy Institute. I purchased some when I was trying to be a better lover. I had been in a monogamous long-term marriage, but neither of us had much experience and I had also grown up in a household where it had been "No sex before marriage" and sex was not discussed. Some things may come naturally, but you can enhance the experience with a little knowledge. I have even seen these videos for rent in my local video store, as well as advertised online and in catalogs. I also think talking to your partner is very important. It doesn't have to be as a student/teacher relationship, but if you can't talk about sex openly and honestly with your potential partner, you probably shouldn't be having sex with each other.

I hope this helps.

Excellent advice Susie!  I've never actually seen a Sinclair video but they look very interesting and are porfessionally done.

Susan