I’m a 33 year old man who was the victim of more than 20 years of physical, emotional and non-penetrative sexual abuse; as you might imagine this has impacted my sexuality in pretty negative ways. But thanks to more than a decade of therapy, I believe that I have put the most of the worst behind me and I would like to lose my virginity. I respect prostitutes a great deal, but there’s a part of me that doesn’t want that as my first experience. I could go out and get a girlfriend (I’m actually quite comfortable with women), or I could attempt to have a one-night stand, though I don’t know the first thing about doing that. I could go back into more therapy, but at this point I’m leaning towards doing the deed itself being the best form of that. I would appreciate any assistance you might possibly render with your wisdom and experience in this field.
There’s nothing wrong with taking the slow, socially-approved route of getting a girlfriend and losing your virginity to her, provided you
A) aren’t in a rush;
B) are reasonably sure you won’t have any extreme reactions if she accidentally does something that triggers a traumatic memory; and
C) don’t really care about the quality of the sexual performance itself.
If, however, you feel a sense of urgency about this, like you “need” to lose your virginity right away, it’s probably much better to get a professional. With a pro you can control the time and pacing; it will happen when YOU are ready, not when an amateur decides she’s ready. And while navigating the dance of consent and the give-and-take of a romantic relationship is probably something you should learn at some point in the future, learning it right now, at a time when you aren’t yet sure you’re completely over your trauma yet, might be more than you can handle. Furthermore, I’m a little uncomfortable with the way you say, “go out and get a girlfriend”, like “go and get takeout food”. It makes it sound like you plan to use her to lose your virginity, and then…what? What if you have a traumatic reaction, as I touched on above? What if you get really needily-attached to her, or have a bad experience and reject her? While those are things an adult woman should be able to handle, it’s just not ethical to dump your garbage in someone else’s yard without her permission, and frankly, most amateurs really have no idea what they’re doing when it comes to dealing with any sexuality more complicated than the typical vanilla “love” or lust-based interaction (which is why their STI rates are so damned high). To me it’s a lot more honest, ethical and sensible for you to pay a seasoned professional (choose one who has a long internet history and a reputation for patience) for a multi-hour session, take her to dinner, get to feel comfortable and tell her about your issues so she can be ready. Once you’ve got that troublesome first time out of the way, you can decide how you want to proceed in the future. But given that most amateurs are barely even competent to give an untraumatized person a decent first time, I think your reticence runs counter to your best interests. At one time it was quite normal for young men to have their first experiences with a whore; the modern preoccupation with amateur initiations is based in foolish romanticism, not good sense and a sober analysis of what would provide the best results.