a 21-year-old female, 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.
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 (babeland.com,
good vibrations.com, comeasyouare.com, grand opening.com,
familychristian.com)—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
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
And, no, I’m not kidding—this will work, WANTS, trust me.
This is a “reader submission” I found on cosmo politan.com’s
freezing day last winter, a pipe burst in my bathroom. My
local plumbing service sent a really hot guy named Jason to
come fix it. After he left, I couldn’t stop thinking about
him, so the next day, I called the same company to complain
about a clogged drain in my kitchen and requested Jason. When
he showed up, he discovered that the drain really was clogged
. . . with my sexiest thong. I started kissing him while he
was still half under the sink, and we wound up having sex
right on my tiled kitchen floor.”
I have always had a feeling that some of those stories are
fictional. What do you think of this one?
Reader’s Understandable Doubts
know for a fact that this story is 100 percent true, CRUD,
because I submitted it myself. That was my kitchen, my plumber,
and, yes, my thong. Not my sexiest though—I mean, come on.
That plumber was cute, but not ruin-your-sexiest-thong cute.
Oh, and my kitchen floor isn’t tiled, it’s covered with wrestling
mats because, hey, there’s nothing naughtier or more arousing—nothing
kinkier—than doing it right there on the kitchen floor. At
least that’s what I’ve been reading in Cosmo for 30
I’m a 21-year-old college student. I’m a gay male, and
I have a thing for crossdressers. That isn’t unheard of, I
know, but my thing for crossdressers comes with a twist. Most
admirers like crossdressers who look like girls. I don’t.
I like it when a crossdresser 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 crossdressers 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 crossdressers
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
wouldn’t say you’re into crossdressers, 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 crossdressing, per
se, but the dissonance, the tension, and the contrast created
by the crossdressing.
But that’s neither here nor there: How can you find the macho
man of your dreams? The overwhelming majority of male crossdressers
are straight, as you know, and most of the gay crossdressers
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?
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, SYM—you can be the therapist he refuses
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
After reading the letter from the girl who was “shocked and
amazed” that people have a swim-cap fetish, I recall that
it was quite common in certain bondage publications of the
’70s and ’80s. It’s nothing new.
MY personal fetish involves the polar opposite. I enjoy wearing
thong sandals (I dislike the term “flip-flops”) and I like
my dates to wear them. (BTW, I’m a straight guy, late 40s.)
Sometimes I get a good reaction, but most times, women are
resistant. They’d rather wear pumps or wedge heels instead
of something comfortable. Could you explain why women would
rather wear footwear that will kill their feet and give them
bunions instead of cushy thong sandals?
Sandal Lover In Los Angeles
for a brief period in my life when I wore them myself, TSLILA,
I’ve never understood the appeal of high heels.
a new Savage Love podcast every Tuesday at www.thestranger.com/savage.