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I’m a 21-year-old woman, and I’ve been going out with my boyfriend for four years. He wants me to masturbate for him, but I don’t feel comfortable doing it. I love my boyfriend and plan on marrying him, but I cannot find a way to do this. I would like to do it. I just can’t bring myself to let him watch.

Wishing And Needing To Satisfy

So don’t let him watch, WANTS – at least not at first.

Here’s what you need to do: Get your ass into a nice, cozy sex-toy shop – or visit one online if you’re too shy (,,,, – and buy yourself a pair of nice, cozy blindfolds. Then go to a big, intimidating hardware store and buy a big, intimidating roll of duct tape. Then go to a bright, shiny Apple store and buy yourself a bright, shiny iPod. Then have your boyfriend sit in a chair next to the bed, put one of the blindfolds over his eyes, slap a piece of duct tape over his mouth and put a pair of headphones – not earbuds, headphones – over his ears. Then get in bed, put the second blindfold on yourself, forget he’s in the room and masturbate.

No need to be self-conscious: You can’t see him; he can’t see you – or hear what you’re doing or speak to you. All he can do is sit there and enjoy the mental images.

Once you’re used to masturbating with your sensory-deprived boyfriend in the room, try it without wearing a blindfold yourself. Once you’re comfortable with that, do away with the headphones and let him listen. Once you’re comfortable with him listening, stop taping his mouth shut and let him mumble sweet somethings. Then ditch his blindfold and let him watch.

And, no, I’m not kidding – this will work, WANTS, trust me.

I’m a 21-year-old college student. I’m a gay man, and I have a thing for cross-dressers. That isn’t unheard of, I know, but my thing for cross-dressers comes with a twist. Most admirers like cross-dressers who look like girls. I don’t. I like it when a cross-dresser is a macho, moderately hairy, athletic jock, who just happens to be wearing women’s clothing. When I see some tall lacrosse player with gorgeous hairy legs, I think, “God, he’d look so damn good in a skirt.” So it’s not the pretty, passable cross-dressers that do it for me. It’s the all-American jock next door. Put a body like that in a sexy teddy, and I’m so gone.

How do I deal with this desire? It seems like most cross-dressers are either straight or they’ve got a feminine body. How can I find the macho man in dresses of my dreams?

Loves Jocks In Frocks

I wouldn’t say you’re into cross-dressers, LJIF, but sexual transgression. It’s not any guy in women’s clothing that turns you on, but masculine, built, hairy guys in women’s clothing. So what turns your crank isn’t the fact of the cross-dressing, per se, but the dissonance, the tension and the contrast created by the cross-dressing.

But that’s neither here nor there: How can you find the macho man of your dreams? The overwhelming majority of male cross-dressers are straight, as you know, and most of the gay cross-dressers out there are interested in passing. This leaves you with two options: a long, frustrating search for the mythical big, burly, gay jock that gets off on women’s clothing, or finding a big, burly, gay jock who loves you so much that he’s willing to dress up for you.

I was chatting with a guy who was looking to give away his money. That’s all he was asking for – giving it away, with nothing in return. He said it is a compulsion of his, and mentioned being sexually abused as a child. He wanted nothing in return, and part of the deal was that I’m not allowed to keep it, save it or give it back to him. He’s a poor 24-year-old student, definitely needs the cash, and I definitely don’t. I asked him to give it away to a therapist – he agreed it was a good idea, but declined.

I had him send me $10 by PayPal to make sure he’s not bluffing. He wasn’t and he’s willing to send much more. I feel that my little game has gone too far, but what to do?

Save Your Money

It’s his money, SYM, and he can give it away if he likes. And if you don’t take it, he’ll find someone with less scruples who will. So take some, just a bit, and only now and then. And keep him talking – you can be the therapist he refuses to see.

And bear in mind that a “cash slave” kink is as valid as any other kink – provided he, like all other kinksters, maintains some sense of balance and doesn’t destroy his life (or bankrupt himself) in pursuit of his particular thrill. If he can indulge this kink without being self-destructive, then he may not need a therapist. And, as always, there are worse things he could be into. He’s not asking you to castrate him, or shit in his mouth, or sit through one of Fred Thompson’s town-hall meetings.

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