First of all I would like to preface my question with an enormous thanks to you and Carlin for all the passion, knowledge and dedication you put into your work. To have a resource of this immeasurable quality is invaluable to me and I hope that your message will continue to spread!
I am writing because I value your opinion most of all and am unsure of how to proceed. Forgive me for all the details but I want to be comprehensive.
I am a 22-year-old female. I have been self-sexual since the first onset of puberty at 10 or 11 years old.
However, I have never been penetrated in partner sex as I am always too tense/tight or perhaps dry/not aroused enough to attempt penetration without extreme pain. I believe my problem is physical because I can penetrate myself with one or two fingers (depending on arousal) and I have never had any problem with tampons. I don't believe my problem is emotional/psychological because I have a very liberal attitude towards sex and do not have a history of abuse or sexual repression, indeed I have always been aware of my mother as a sexual being (although initially perturbed since my parents were separated and the thought of her having sex for pleasure was initially very confusing) and at home she was often naked.
I have never been in a relationship and I have only felt compelled to engage in partner sex on a few occasions: always in the circumstances of a spontaneous one-night-stand or fling. I like intimate situations which come about spontaneously, for example when I meet someone while travelling, and I think I have some negative thoughts I need to overcome regarding dating and relationships being contrived and therefore less desirable.
Elements that I think are contributing to my problem: I haven't had many sexual experiences so I lack confidence, I have never had sex with the same partner twice, I am shy to communicate with a partner, partners have been inexperienced, and I have felt frustrated by having to stop, explain and compromise when I attempt penetration.
I hope that if I can find a partner to practise with regularly, I can learn how to overcome the problem of penetration with communication and experimentation (for example I get really turned on by the thought of biting and spanking and never bring it up).
I know it sounds like penetration is my end-goal here, but truly it is because I appreciate oral and manual sex and I want to try something more.
With that in mind, after joining a couple of online dating apps I went on a date with a 33 year old man who (besides being very interesting and we had good chemistry) is very sexually experienced. Late in the conversation I explained some of my situation to him, about never having been penetrated and fundamentally wanting to be slutty but my body not letting me. Even on this date I tried to become more comfortable talking openly about sex - I asked him what he thinks makes Good Sex. As you can imagine, it was easy to establish that he was a willing candidate!
But now... honestly, I am worried again that my shyness and embarrassment will get in the way of what I want. And I am worried about being taken advantage of. I have the overwhelming feeling that I am at a crossroads. If I don't follow through and try to make progress on this, I could be in the same position forever, but fear is getting in my way. I think I am answering my own question here, but I'm looking for words of encouragement and practical advice on how to proceed.
Thank you - for everything,
Dear G, With your healthy background of masturbation the only thing stopping you is......What? Now that you have an older BF who is naturally willing to accommodate your request....go for it. Some questions first. Do you have adequate birth control? Do you have additional lubrication? Can you create a secure space for sex?"
The note of warning: the "first time" usually sucks. So don't be disappointed and instead find a boy you'd like to have an ongoing affair with. Good partnersex takes time and communication. Nothing wrong with having sex with the same guy for a while. You're doing great.