Sexually Re-Oriented

Friday, October 06, 2006


My boyfriend and I have been together almost a year. For several months, he talked to me about his greatest sexual fantasy, which was to be able to watch me with another woman. (I know, big cliché, but I really love him.) He eventually talked me into it, which wasn't too hard because the only friend I have who has experimented with gay sex is quite attractive. So we had "Tammy" (not her real name) over for drinks. I had already told her this would be a big favor to me because it would make him so happy. She asked me what I was getting to get out of it, and I giggled and said I wasn't being altruistic; the thought of having a threesome was turning me on.

But I had to be sure that she wasn't going to make any moves on him, because that was my biggest fear about doing this. I didn't want to lose him to somebody else who was more experienced and maybe more beautiful than me. She laughed and said, "Don't worry, honey, your friendship means more to me than that. I want to do this because I want to have sex with you, not because of him." I was blushing so hard, I felt like everybody in the restaurant had to know what we were talking about, and my panties were sticking to my wet little pussy.

Here's something that should have warned me there might be a problem. She asked me how long I had been attracted to her. This really took me aback. I mean, I've always looked at other women (doesn't everybody?) and sort of ranked them according to who was cute and who wasn't so cute. But when I thought about it honestly, I had to tell her I had been fantasizing about kissing her and having her touch me ever since we first met. I'm just used to thinking of sex in terms of men approaching women; I feel stupid now (oh, do I!) for not following up on my curiosity.

Well, we had the date, and it went even better than expected. My boyfriend Geoffrey sat up in an armchair, wearing nothing but a silk bathrobe, and watched while Tammy arranged me on the bed. She was really gentle and sensuous, taking a long time to undress me and always making sure I was comfortable before she moved on to the next thing. By the time she finally went down on me, I was so wet I was amazed. I don't think I've ever lubricated that much before; I just thought I was one of those girls who didn't get very wet. After about ten minutes of gorgeous sensations from her soft mouth, I curled my toes and grabbed the sheets and came so hard and so loud I thought plaster was going to fall off the ceiling.

Then she put her fingers inside me and went down on me again. But this time she was in a position that let me see her pussy and touch it. She had already let me touch her breasts, which was another new and painfully exciting thing for me. By tugging on her legs and pleading, I managed to get her to let me lick her while she was eating and finger-fucking me. I came again. And again. Then we changed positions so I could eat her more comfortably. She was on her back, holding my head, telling me what to do, while Geoffrey looked at my pussy, which was pointed straight at him, and jerked off like a mad man.

Here's the thing: I never came that way before. I liked sex. I especially liked knowing that my partner was having an incredible orgasm inside of me. I love holding men and feeling their hands on me. But I just never felt anything like the way I felt with Tammy.

We finally wore each other out. Geoffrey had gotten himself off about eleven times, so he was really happy, and we all got cleaned up, and kissed Tammy goodbye so she could go home. The next morning, Geoffrey fucked me in every possible position. He used his hands, he used his mouth, and finally I had to tell him that I was getting sore and I had to stop. I could tell he was really upset, but I gave him a big sloppy blowjob and after he came I thought everything was okay between us.

But just before I went to sleep, he said, "You liked having sex with her more than you like having sex with me, don't you?" I pretended to be asleep because I was terrified to answer him. I didn't want to lie and I didn't want to cause a big fight. I don't know how to compare the two experiences. I love the way he smells and I want to have a life with him. But I can't stop thinking about how it felt to have her beautiful breasts in my hands, to be mouth-to-mouth kissing her while our nipples brushed against each another. I've masturbated at least twice a day thinking about it. I'm walking into walls, wet all the time, and so horny I keep asking Geoff to fuck me, but it isn't what I really want and I think we both know that.

Tammy asked me to get together for lunch, and I went without telling Geoffrey. She knew right away that something was the matter and asked me what was going on. I told her that I was really confused and couldn't stop thinking about her. I told her that I had my first real orgasm with her that night. She confessed that it was one of the hottest experiences she'd ever had. Then she said that she's thinking she may be more lesbian than bisexual, and didn't want to do another threesome even though the last one had been just fine. "I don't suppose your boyfriend would let you spend some night alone with me?" she asked.

What do I tell her? What do I tell him? I was just trying to be a nice, sexually open lover who was going the extra mile to titillate my man. I never expected to open this new potential area of experience for myself. I don't want to turn back. How can I, when I now realize that sex can be so much more satisfying for me? I have a rapport with my girlfriends that I realize I've never had with men, no matter how sensitive they are. A relationship with someone who understands you that well, and has that sexual empathy with your body, must be really something.

There's nobody I can talk to about this who would be objective. I don't want to hurt anybody. This was just supposed to be a fun evening. What the hell do I do now?


This Tammy must be really something. I want to have a hot affair with her, and all I did was read your letter. This story ought to be a cautionary tale to every dude who thinks he can manipulate his straight female partner into a threesome with another woman. Once you bring a new sexual experience into your lover's life, there's no telling what the consequences will be. If Geoffrey was a consistent and ethical person, he would tell you, "Honey, after begging you for a ménage a trois, I can't claim to be monogamous. You thought you were doing me a big favor. It's only fair that you got as much out of it as I did. Go have some fun with Tammy. Just let me know when you'll be coming home, if at all, or if I should organize a coming-out party for you."

Unfortunately, few men (or women, to be fair) have the guts or the altruism to apply the same standards to a partner's needs and fantasies that they do to their own. I don't blame you for being nervous about talking to Geoffrey. But the fact is, this relationship has changed. You can't go on the way you were before. You could pretend that nothing has changed, and stay away from lesbian sex, but you'd resent him so much that it would poison the good things you share. You could have a secret affair, telling yourself that what Geoffrey doesn't know won't hurt him, but unless he is incredibly stupid or self-destructive, he will sense that you are no longer his alone, and feel betrayed.

Seems like the only ethical option is to talk to your sweetheart about what you are feeling. I hope he can listen without being too threatened. If he can't, and says mean things to you, you probably needed to know about that aspect of his character before you got more involved with him. He was the one who brought this whole thing up; you haven't done anything wrong. If he can't bear to have an open relationship and stay with you while you pursue your newfound knowledge, that's his responsibility to say, but he has no business insulting or threatening you.

I hope you will bear in mind that the first time anybody has an orgasm, they are bound to idealize the person they had it with. You don't know, right now, what this experience means. Maybe Tammy is exceptionally skilled. She might be the only woman you could ever have as a lover. Perhaps you have discovered a response to other women that runs so deep, you won't want to have men in your life any more. Getting the answers to these questions could take another two dates or a couple of years. Is it fair to ask Geoff to stick around during this process? That's up to him. Is it fair to ask Tammy to put up with you having a male lover? That's up to her. All you can do is be honest about your own feelings and allow them to make their own decisions based on the truth.

As a bisexual, female-to-male transsexual who spent about 30 years trying to make a lesbian identity work, I am in the unusual position of being able to tell you that relationships with men and women (or folks who don't identify with either gender) are all about the same, with the important exception that our society has chosen to stigmatize and punish relationships that are not heterosexual. (That's a pretty big exception, by the way. A lot of women who would identify as lesbian or at least bisexual stay away from that realm of erotic experience just because they don't want to be persecuted for being queer.) People of all genders can be manipulative or honest, decent or mean, good in bed or a terrible time, empathetic or psychically dead. Few people are all bad or all good; who knows if Tammy can offer you the same quality of relationship that Geoffrey apparently has?

In closing, it occurs to me that you might not have to choose between Tammy and Geoffrey. If he is willing to be with you while you explore sex with other women, maybe you need to find a new girlfriend who would like a threesome with both of you. That way, Geoffrey gets to have his fantasy, you get to see what sex with another woman is all about, and nobody needs to pack up their stuff and move to a cheap studio apartment in a bad neighborhood.

Leave a comment

Comments will be approved before showing up.