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Sexually inexperienced male in desperate search of answers and ideas!

Tagged as: Big Questions, Friends, Sex, Trust issues<< Previous question   Next question >>
Question - (2 July 2010) 6 Answers - (Newest, 3 July 2010)
A male United States age , *inchCelibate writes:

I am extremely inexperienced at having sex. It has been a long time since I have and that was very few. I am very small down there anyway and that doesn't help my self esteem. The few times that I have found myself in a situation for an opportunity with a female I just don't do anything. It's like I am scared or something.

Anyway, I have a female friend that I talk to a lot but we are just friends as she is married and has been for about 15 years. She is very pretty, funny, lots of fun to be around and she is very experienced sexually. We talk a lot and we both know just about everything about each other. She trusts me and I trust her. She knows I never get any and how many times I have and who it was and I know she has done it many times and loves doing it now a lot but only with her husband.

She ask me if I would do some work for her on a couple of her rental houses that she owns and I told her sure, no problem. She said to ballpark a price and she would have some cash on hand for me. I told her that instead of getting all money that I would rather have just a little money and the rest in her guidance and expertise.

She asked in what? I said in what you know well and I know nothing about. She said have you still not got you no pussy yet? I said no and she said how do you want me to help you and I said first I would like for you to watch and then grade me on a simulated performance test I will do for you and then tell me what I need to work on as a homework assignment to practice and then grade me again on another performance to see where I stand. She said don't tell me you bought a love doll. I said I had to do something and she laughed and said so instead of paying you money you would rather me watch you have sex with a love doll. I said you got it Babe.

She said are you sure about this because it might cost you more than you make on those two jobs for me to

evaluate that for you. Plus you would end up working over there for free and then still have to pay me money to watch how you make love. I told her that was fine, just whatever it takes to locate the problem and solve it.

So those are the plans as of now and some may think it's crazy and if they do then so be it. I have always been one to listen to advice but never been one to worry about what someone says or thinks about the way I do some things. Advice I accept, sarcasm I either ignore or return.

My main goal here is finding options, ideas, and opinions on the current plan in place or ideas for possible future plans for a solution.

View related questions: money, self esteem

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A male reader, anonymous, writes (3 July 2010):

Consider this, there are many men in the world who have a 3incher. Of course, for some women, this will be a let down, but so what!? For other women, this will be fine, as this length is enough to hit their gspot.

Build up your self-confidence, accept who you are. There is nothing wrong with you. Be communicative, and upfront. Try an adult dating site, and be honest about your measurements and your experience. What do you have to lose?

This all might seem like the opposite of what you have done of might consider doing, but think of it as taking all of your insecurities and putting them infront of you.

Get it out of the way so you can get on with what matters - having a fulfilling relationship (which includes a sexual relationship).

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A male reader, 3inchCelibate United States +, writes (3 July 2010):

3inchCelibate is verified as being by the original poster of the question

3inchCelibate agony auntThanks for your response and advice. I appreciate it. Let me go ahead and clarify something here concerning my friend that I asked for help being married. As I stated earlier, we are very close friends and that is all. I know she wouldn't cheat and her husband knows she wouldn't and most importantly she knows she wouldn't. We all three get along great.

She is the only one that I would ever ask to do this for me simply because our close knit relationship as friends will allow it. She can tell you what I am thinking and I can tell you what she is thinking before either of us even say it. I can text her and she will text back saying this thing hasn't went off all day and quick as I picked it up to text you I get one from you. That happens a lot.

For us, this deal would be no different than riding to the store together. It won't bother her when it's done, it won't bother me when it's done and it won't bother him. His response to it will be to the tune of a chuckle and the words, "Ha, only him to come up with something like that" with a kicker of "but that sounds just like him though". "They definitely broke the mold when they made him". Her response would be "I just wish I could tell someone just to watch their expression but they wouldn't believe me and think we are both crazy".

That's the jewel of our friendship and I wouldn't have it any other way and neither would she.

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A male reader, 3inchCelibate United States +, writes (3 July 2010):

3inchCelibate is verified as being by the original poster of the question

3inchCelibate agony auntThanks for the responses so far. I don't anticipate any problems for either of us from her help. We are very close friends and she is totally a one man woman. Her husband knows this and he understands our friendship is a close one but nothing more.

The talking to the females is a major part of the problem and we will address that issue as well during this upcoming simulated session. It might be considered by some as putting the cart before the horse by planning to perform the simulation first but I wanted to go ahead and get that evaluated along with the assignments for it in place.

To the female that mentioned about me being comfortable with it, actually I am simply because we understand each other so well. Sure, we will have some fun with the whole thing and both get a laugh out of it and that will be good too, for both of us. We have both seen the other do some crazy things and that's one reason this didn't surprise her none. She knew that I was the only one crazy enough to mention it and I knew she would be the only one that wouldn't bat an eye about it when I did.

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A reader, anonymous, writes (3 July 2010):

The first thing I would say is stop talking to a married woman about sex and/or performing in front of her. This situation is not appropriate if she plans on staying married.

That being said. My fiance' is also very small down there however he is the BEST lover I have ever had bar none. My ex-before him had a huge penis and he wasn't nearly as good a lover. Here's my advice. When you are with a woman....think about EVERY SINGLE touch. Really appreciate every inch of her body. If she has a tiny waist...concentrate your touch there...if she has a lovely long neck...concentrate your kisses and touch there. Take your time. Learn to eat pussy REALLLYY well (this is key if your penis isn't the main thing you feel good about). Use your hands and mouth slowly, sensually and consciously and you will be allll good. A big dick is not all it's cracked up to be. I promise. Good luck, you'll be fine.

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A female reader, anonymous, writes (2 July 2010):

Whatever you feel comfortable with!

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A male reader, anonymous, writes (2 July 2010):

Wow...that's tops them all. Well, I will say...you are a crafty bugger. That is the most amizingly discreet, but effective way I've ever heard to get a woman to "help out". But if you think it will work, and she's willing, I say go for it. But, the problem here seems to be your lack of confidence and ability to talk to women...not how well you may or may not fuck a doll. You have a rapport with this woman (who's married, so not sure how that works out) and having her continue to help you may truly help you, get one or both of you into trouble, result in nothing at all, or frustrate you more. It's an unusual circumstance, and you need to be prepared for whatever comes (no pun intended). Good luck tho.

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