Struggling with Her Baggage
I'm a young heterosexual male, and I've recently fallen in love with a fantastic slightly older woman. When we first got together, we were always "on," but with a sense of humor. It was great harmless, innocent sex. We're past the honeymoon phase, and I am starting to worry. She knows most of the issues you are about to read.
I am feeling intimidated by her sexual experience and paranoid that I am not living up to expectations. She didn't have much of a sex life until two or three years ago, when she got out there and really started to explore. She's implied that she's pretty much down with anything, and I'm beginning to realize that I am too (with certain limits). In the last eight years, I've had average sex in a variety of relationships with fairly prudish partners. She's very verbal, not afraid to talk dirty, and quite open. I am beginning to adapt and act the same.
My current lover has a lot of baggage about one particular ex. They had a casual relationship, but she says "the sex was awesome." He was fairly crass and callous, so they broke up, but even after that, if he came around, she was available. When she finally gave him an ultimatum, he broke her heart and insulted her weight, income, lifestyle, etc. She still struggles with self-esteem and fears of rejection.
Being a jealous character, I find this gnawing at me, that he was there for her "sexual awakening," and I was not. I'm assuming there was probably a lot I don't know (and don't want to know) about their sex life. But I know I have some big shoes to fill, despite the fact that we feel deep love for each other.
Am I being irrational? She says I'm great in bed with the basic stuff we're doing, which I'm not bored with. But does she want the casual, experimental dynamic she had with her ex already? She wants me to start poking around her ass the way he was, which I'm beginning to warm up to. Just not when my brain interprets it as her wanting me to be more like him. I feel she's already outpaced me and wants the sort of things I've grown up interpreting as signs of sexual dissatisfaction and a means for reinvigorating a failing sex-life.
Oooooookay, dude. It's all about her baggage. Yeah, right. You could sing all the verses of the Rolling Stones song "Beast of Burden," huh?
This is a common relationship problem. The man asks the woman, "How was your sex life before we met?" I sometimes think women should never answer this question honestly. "I never knew what hot sex was before you did me, honey," seems to be the only reply that won't cause a problem. I'm making a joke out of this, but I honestly don't mean to make fun of you, Heavily Burdened Reader. Just about 100% of us have got a possessive streak a mile wide. Even the most civilized among us is marking a woman when we have sex with her, saying to anyone else within view, "This one is mine. Mine, mine, mine. Go get your own and leave mine alone."
We grow up without a lot of information about how other guys do it. We don't get to see adult sexual behavior unless we watch porn. And porn does not give us an accurate or helpful model for our own lovemaking. Those hard cocks are way, way above average size, and I have yet to see a female porn star have a believable orgasm. Amateur porn can be more accurate, but to be honest, when I am watching sexually explicit material, I don't want to see average people—I want the pretty, idealized bodies the sex industry keeps bringing us.
But you didn't write to me to hear an exposition on porn. The point I am trying to make is that we feel competitive with other guys and insecure about our own performance. I've had men write to me claiming to be premature ejaculators, and then I later discover they are able to last way longer than the under-ten-minute average. Their partners were having trouble orgasming, but that didn't mean they were coming too fast. So when we hear a lover describe a past encounter in glowing terms, we immediately get riled up and anxious.
Until the 1960s, the solution for the fragile male ego was to require the woman to be a virgin. If she'd never had anybody else, she wouldn't have a basis for comparison. But this couldn't continue if women were going to have full sexual agency and we were going to grow up and be reasonable people. Jealousy is understandable, but the solution is to learn how to soothe and reassure yourself. Fantasizing about how good the other guy must have been, resenting her for being a slut, or getting suspicious about her wanting other people are not helpful. The truth is that having a lover who's got some experience, initiative, her own ideas, etc. is a lot more fun than a passive partner who leaves us to do all of the work. You can't have it both ways, though. If you want to enjoy her openness, you have to stop being an asshole about how she got that way. The only way to calm down is to believe in yourself. Believe that she really could be happy with you, satisfied by you, and focused on only you.
Your values are tripping you up. For some reason, you got the idea that exploring certain sexual techniques means your relationship is in trouble, and you're desperately trying to save it by getting kinky. Unless you can revise that attitude, your relationship is doomed. I'm very serious about that, now. Do you want to keep this woman around? If so, you have to grow and change.
First of all, the term "kinky" is always relative. In some cultures, everybody has anal sex because it's an effective form of birth control. In others, it's a bad, wrong thing only sick, dirty people do. (And in many cultures, people will say the latter while doing the former.) It sounds like you aren't really comfortable with fucking her in the ass, but her exemplary jerk of a boyfriend did it, so you feel that if you don't, you won't measure up. Stop putting so much pressure on yourself. Ask her how important it is to her for the two of you to do anal sex. It may turn out that she can take it or leave it. If it seems disgusting or weird to you, you won't be able to get it up anyway, so don't put yourself in that kind of a double bind.
Toys are always an option. If you don't want your cock to go there, maybe a little butt plug or a vibrator will make her happy. Put a condom on the thing so it'll stay clean, dab on some lube, and let her dictate how fast or slow it goes in. It's easy to hurt the anus; you need to be more careful with this orifice than with the vagina. The rectum angles back toward the small of her back, so be careful to let the toy follow that angle. Otherwise, you'll hurt her, and she won't want to do this again.
If you do want to try anal sex, do it because you think her bottom is really cute, and you'd like to have her at your mercy that way. Do it because you want to hear her make that noise when you enter her. Put on a latex glove, lube up your fingers, and explore her butt. This keeps everything clean and makes your fingers more slippery. Let her tell you when she is open enough to take your cock. Tell her what you need her to do to get your cock hard. Be sure to use a condom.
The most common fear about anal sex is that you'll be covered with shit. But poop is actually stored a few inches away from the anal opening. If she's had a bowel movement that day, you may not find any at all. (This is one reason to go in there with a gloved finger first.) People who make anal sex a regular practice may opt to take a small enema beforehand. A cup or so of liquid is usually plenty to clean out the lower part of the colon. Use plain water, not a harsh chemical enema. Drugstores sell a variety of equipment for this hygienic routine.
Next time you feel a twinge of jealousy, ask yourself, "What am I feeling insecure about? Why would she want me more than him?" Learn how to give yourself an effective, grounding pep talk. If it upsets you too much to hear about this other guy, ask her to declare a moratorium on the memoirs. And keep his faults uppermost in your mind. She's not with him. That's your best weapon against the green-eyed monster.