I left prison a virgin after 28 years. Now I am struggling to have sex

Pamela Stephenson Connolly
Illustration: Guardian Design/Getty

I was released from prison last year at the age of 46 after serving 28 years. I was a virgin when I went to prison and I am still a virgin. My whole adult life I have masturbated – sometimes once a week, sometimes seven times a week. I’ve seen plenty of pornography (magazines and movies) and used these things at times when I masturbated. I have never had a problem getting an erection when I masturbate.

Since my release, I have met two women. When it was time for sex with the first, I could not get an erection. She tried using her hand and she tried oral sex. Neither worked; it actually felt weird, I guess because only my hand had ever touched my penis. That relationship ended. The second woman I have been seeing for months. She knows of my time in prison and that I am a virgin. When she told me I could go all the way with her, I couldn’t get it up. She was understanding and said it will happen in time, but that did not console me. I am convinced that almost 35 years of masturbating has ruined me.

I love her and we will try again one day. When we do and I fail again, I will have to let her go so she can find a man who can satisfy her in that way. I have waited my whole life to lose my virginity. Maybe I need Viagra or some other drug. I had figured that the only problem I would have would be achieving orgasm. I am depressed and scared at the same time. I don’t know what to do.

I am sorry that you have become so anxious about your ability to achieve and maintain an erection. But there is no need to be so concerned. It is very unlikely that masturbation has had a detrimental effect on your erectile ability. In fact, it was a good way to sustain your sexual functioning over so many years in prison. The ability to be sexual with a partner is something everyone has to learn; as your recent partner suggested, it will just take a little time. Bridging between sex alone and sex with someone else will require you to relax and let go of your goals to “perform” or even to achieve erection. Instead, try to focus simply on giving and receiving pleasure. You will also need the ability to listen to your partner’s needs and an ability to share your needs with her. And there is nothing wrong with seeking pharmacological help with erectile functioning – at least at first. Most importantly, I understand why pornography may have been the main source of your sex education, but what you learned is not necessarily correct or helpful, because everyone is different. Be patient with yourself. You are about to enter a new phase in the natural process of sexual development that everyone undergoes throughout their life.

•Pamela Stephenson Connolly is a US-based psychotherapist who specialises in treating sexual disorders.

• If you would like advice from Pamela on sexual matters, send us a brief description of your concerns to private.lives@theguardian.com (please don’t send attachments). Submissions are subject to our terms and conditions: see gu.com/letters-terms

•Comments on this piece are premoderated to ensure discussion remains on topics raised by the writer. Please be aware there may be a short delay in comments appearing on the site.

Pamela Stephenson Connolly is a US-based psychotherapist who specialises in treating sexual disorders