Mixed signals, or, putting a finger in my butt

What if it hurts and I like it?

My boyfriend and I are straight college students, and he's always wanting to try new things. Recently, he asked to put a finger in my ass while we were having sex. Someone did that to me before, but it felt uncomfortable and it kinda hurt. I told my boyfriend that he could do it once and then I would decide whether to let it continue. So we tried it. It still felt uncomfortable and still kinda hurt. But I never came so hard in my life!

Now the question: If it's uncomfortable, but it made me feel amazing and come really hard, what should I do? Continue with it? Or tell him to find some other way of getting me to that point again?

Presently Obsessing Over Totally Extreme Reaction

You could ask the boyfriend to stick a finger in one of your armpits-or in an eye, a nostril, your toaster-but unless your pit/eye/nostril/toaster is wired the way your butt appears to be, POOTER, no amount of pit/eye/nostril/toaster fingering is gonna jack up your orgasms quite the way that finger in your butt did.

So here's what you're gonna do, POOTER: You're gonna breathe deep, you're gonna take things slow, you're gonna use more lube, and you're gonna spend more time warming up the outside of your butt before anything goes in. (Tell the boyfriend he can finger your butt for 10 minutes after he rims it for 20.) Do it right, POOTER, and pretty soon you won't be able to look at those 10 fingers of his without thinking about the kick-ass, anal-enhanced orgasms you'll be having when you can only see nine.

I am a 27-year-old male, identify as bisexual, and enjoy crossdressing ­— although I have only crossdressed with guys I meet online. I have no real desire to meet guys unless I'm dressed up. And when I do get together with a guy, once I cum, I'm ready to leave. I can't see myself in a relationship.

With females, I can see myself getting married and having kids, etc., and when I have sex with a woman, I'm not in a cum-and-go mentality. But when I'm dating a girl, after about a month, I start to float back to jerking off while chatting — just chatting, not meeting up — with guys who found my online crossdressing profiles. I could try to get a gal to use a strap-on, but that doesn't appeal to me. I like flesh-and-blood cock.

So I guess my question is this: Do I hold out for a gal who is open to me having the odd bisexual encounter or do I learn to use my imagination a bit more during strap-on play? I only fantasize about cock when I'm already horny, and I lose all interest in it once I've cum. I thought in the past that I might be gay, but I figure since I have no desire to date men and can't see myself with a guy long-term, I must be bi. What are your thoughts?

Sorry If This Question Is A Little Scatterbrained

First, SITQIALS, I'm sorry if my response is a little scatterbrained. I'm on vacation and currently in something of an impaired-state holding pattern over the Pacific Ocean. I didn't read all of today's Savage Love mail because the shit that's impairing me is forcing me to take it easy. How easy am I taking it? So easy that I'm not going to change "cum" to "come" in your letter.

Anyway, yeah, it sure sounds like you're into women, SITQIALS, even your fetish screams into dicks. Your crossdressing and role-playing fantasies are all about your bone for women and feminity. You dig women so much, you want to play the role of the woman. But in your fantasy scenarios, SITQIALS, men aren't human beings and sex partners, men aren't people with whom you could potentially have relationships, they're props, the finishing touch that completes your ensemble.

And once you blow your load, once the game is over (once you COME), you're done, you don't need that prop anymore.

So what do you do? Well, I think your fetish makes you pretty damn near incapable of monogamy, and you've already discovered that strap-ons don't meet your particular needs. So, yeah, I think you should hold out for a woman who's into your fetish and turned on by the idea of sharing your ass — when it's wearing panties — with a few good men. It'll mean a longer search for the right woman, which you should be willing to do, because you're worth it.

You might want to Google autogynephilia. Not saying that's where you're at or headed, don't know enough about it to endorse it, but it seemed relevant, food for thought, the more you know, etc.

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