We broke up, and the next year, I got married to a man I’d known for 3 months. During our brief courtship, we never talked about anal sex, he never suggested it, and I never brought it up. After the wedding, I presented him with my gift. I told him that I loved him and wanted to give him something special, that no one else had ever had, to celebrate our bond. He was decidedly less excited about this than I thought he’d be. Have you ever given someone a present that you really put some effort into, only to watch them open it, feign excitement, then set it aside to forget about later? That was how he reacted to my virginal offering. About a year into the marriage, I brought it up again. He somewhat acquiesced, unenthusiastically inserting just the tip, and sighing as though he was bored with the whole thing. It hurt both my body and my feelings, so we stopped there and I never brought it up again.
As I’ve mentioned in previous writing, I didn’t behave very respectfully once I’d given up on a happy marriage. So one night, during the final months of it, I tried to make a friend-of-a-friend “go Greek” with me, only he didn’t want to either. The repeated rejection made my “special gift” seem like a curse that I became obsessed with getting rid of ASAP. Once I was single again, I hooked up with a random audience member after a show. The details were perfect, it was as random as could be. He lived many states away from me, we hadn’t exchanged last names, if things went poorly or embarrassingly, I’d never have to see this guy again. He even had a small penis, which I thought was the universe’s way of giving me the go-ahead. So I made the offer, and WAS REJECTED AGAIN. He said he wasn’t into it, but then tried to appease my desires by jamming in a finger, complete with untrimmed nails. He scratched up a very sensitive area, and I decided to give up on my quest. I shelved it, regretting that I’d forced the issue to the point of injury, and resigning myself to the dramatic idea that this form of lovemaking just wasn’t in the cards for me this lifetime.
Recently though, I’ve been seeing someone who I really like, and more importantly, I really trust. The subject of anal sex has come up, at his initiation, and I don’t want to get prematurely excited, but it feels like this could be the one. I felt secure talking about it with him, he listened and laughed with me, not at me, as I told him about my trials and tribulations. I think that because I was willing to let go of the mission to lose it, willing to let go of the meaning I attached to it, I may have found a person with whom I can comfortably explore this avenue. Fingers (with well-trimmed nails) crossed, anyway…