The other day, I described a recent shopping trip to pick up a new dong for my strap-on harness. Usually when we talk about sex it's playful, and I have never gotten the impression that I've made him uncomfortable. But after this comment about my strap-on, he seemed visibly distressed, so I went back to work and let it drop.
Yesterday, I apologized for making him uncomfortable. To make a long and strange conversation short, he told me he was dating an older man into anal intercourse, but my 17-year-old friend was having trouble getting his butt to cooperate. He was embarrassed to say so at the time, but when I mentioned my toys he was wondering if maybe I would be willing to ... break him in. I recommended he get the old man to help him, but he says that he would feel less pressure to perform if it were me. He says he needs to get over the initial fear of penetration and then he'll be good to go.
Now, I think he's more with-it than most 17-year-old baby fags. And to be honest, although boy butt doesn't turn me on all that much, I can imagine a situation like this being quite festive. But he is, after all, technically illegal. Is there something more I should be considering before embarking on this venture? Is this a lesson he's better off learning in another situation, or is this the kind of opportunity that only a bonehead would question and not pursue immediately?
Hey, DD: No doubt the advice I'm about to give will bring accusations of aiding and abetting baby rape from those unable to distinguish between a 17-day-old baby and a 17-year-old baby fag, but as I see it ... if not now, when? If not you, who?
Before you strap one on, strap this boy down long enough to have a thorough discussion about why he's so anxious to get his butt in gear. Is this what he wants, or is the old man pressuring him into doing things he isn't comfortable with and may not be ready for? Frankly, I'm less concerned with what he'll suffer at your hands than what he may be suffering at the hands of that creepy old fag.
Maybe you can drag this conversation out long enough that by the time you get around to giving him the no-pressure, low-stakes drilling he wants so badly, he'll have passed his 18th birthday. That way, neither of us will go to jail.
Hey, Faggot: I am an Ivy League graduate, but some of my friends are in the smut business. In hanging with this crowd, I've been able to live out some of my fantasies. Sexual exhibitionism turns me on, but my fantasies have all been realized behind closed doors. When it comes to smut, I don't just want to be a viewer, I want to be a star. I like the idea that when I'm old and saggy, I'll be able to watch a video of myself and say, "I sure could shag like a star."
I've been offered many parts, by my lovers and my friends, in the "industry." I know my friends and relatives outside of the industry would support me in my sexual explorations, but there are some groups of people I worry would not approve: future board members whom I might work with, future stockholders investing in my future company, future voters I might ask to put me in office.
Should this be one of those fantasies that I don't ever fulfill, or would it be possible to do just one movie, and hope it gets lost among all the other ones?
Hey, SF: Dirty pictures, like soiled dresses, have a way of surfacing at the worst possible moments: Vanessa Williams' dirty pics being a famous example. Arguably, though, those pics helped Vanessa more than they hurt her; she had to return her crown, but we still know her name. (Can you name any other past Miss Americas? How about the current Miss A?) More recently, former MTV VJ Simon Rex was discovered to have made a handful of pornos prior to becoming a music television star. (Simon's solo jerk-off tapes are still for rent at better video stores.)
Having starred in a porn video before you got old and saggy might not hurt you with board members, stockholders, or MTV execs, but if you have political aspirations, you shouldn't show your face in no porn tape. That don't mean you can't live your dream: If you're as well-connected as you claim, beg your industry friends to feature you as the masked man in a theme video, a la the Lone Ranger. Or maybe Gimp in Pulp Fiction is more to your Ivy League taste?
Hey, Faggot: I'm a straight girl, and I recently had a run-in with an ex-fling. He came to town to see me and brought his best friend along. After an evening of drinks, the three of us ended up in bed. I've always thought that having two guys at once would be an incredible experience -- and it was. My concern, however, is that during the many shiftings of positions, etc., my ex wrapped his mouth around his best friend's cock. My concern is that these two guys have unresolved feelings for each other. They grew up together, and were on a swim team. Do you think seeing each other in Speedos at swim practice and showering naked together had an effect on them? Any comments?
Group Sex Girl
Hey, GSG: The fact that your ex-fling is willing to wrap his mouth around his best friend's cock -- and his best friend is happy to have his cock so wrapped -- is a good indication that, whatever their feelings for each other, those feelings are pretty thoroughly resolved. It doesn't necessarily follow that because your ex is willing to give a tiny bit of head during a three-way that he's a raging closet case. Maybe your ex and his best friend used to mess around as kids, and see no reason to avoid bumping dicks during a three-way now that they're grown-ups.
I get a lot of letters from women complaining about men they've had three-ways with; often the boys are so paranoid about touching each other that the three-way was more about their homophobic attempts to avoid touching each other than it was about three folks getting off together. There are a lot of straight women out there comfortable enough in their own sexuality that they can appreciate other women's bodies without having a panic attack. As straight boys evolve, socially and sexually, there're gonna be more straight boys around who are capable of doing the same with other guys.