Formspring Friday: Unrealized Desires

Have you ever wanted to try something sexually but haven't? What is it and why?

Jack's Answer

For the most part, I don't have a lot of unrealized sexual wants or needs.  I've done most of the things that appeal to me.  I've had anal sex.  I've given facials.  I've had threesomes.  I've fisted.  I've found lots of G-spots.  I've been deep-throated.  I've done sixty-nine while standing up.  I've made a sex tape or three.  I've indulged my exhibitionist side by having sex in public, and by getting naked on a beach.  I've webcammed with more or less total strangers, as well as with online friends.  I've had phone sex.  I've had one-night stands.  I've had multiple orgasms.  I've joined the Mile-High Club.  I've had sex in a moving car.  Certain sexual practices, such as autofellatio, Tantra, and the positions of the Kama Sutra, don't really appeal to me.  So, sexually-speaking, there isn't anything I can think of that I would like to do but haven't.

I said there wasn't anything.  I didn't say there wasn't anyone.  Over the past ten months or so, we've made many new friends through blogging and Twitter, and I can admit to wanting to have sex with most of them, certainly the women.  I know this answer probably sounds like something of a cop-out - many of my Formspring Friday answers are - but the fact is that meeting up with an online friend, ideally someone with whom we've communicated for awhile and who we've gotten to know, for the purpose of essentially meaningless sex would be most exciting.  That is not to say that we would rule out meeting someone with whom we were more casually acquainted, of course.  But for me, and I believe for Jill as well, it's the familiarity with the other person that makes an encounter so exhilarating.  If I've known a woman for a significant length of time, chances are I've imagined what she looks like naked, and fantasized about what sex with her is like.  So it's tremendously exciting to be able to stop wondering.  

Actually, now that I think of it, one specific sexual practice that I'd probably give a whirl is an MFM threesome, either with Jill and another man, or a couple for whom I am the third.  As far as fantasies go, this is something that is relatively new to me.  The appeal comes largely from Jill's enthusiasm for it, though as I stated I'd pinch-hit for another couple if asked.  I don't really have any boundaries where such a threesome is concerned, though I'm not particularly keen on the idea of interacting sexually with the other man in anything but an incidental fashion.  For all my left-wing socially-progressive idealism, this still squicks me.

Jill's Answer

This was a tough question to answer.  There are several activities that I think I would like to try sexually but haven't yet.  I say "I think" because while I am aroused by the thought of these activities, and while I am relatively sure that are scenarios that I would really enjoy participating in, I can't say for certain how I would react until I am actually in the situation.  Both activities would involve at least one person who is not Jack or I, and while all of our non-monogamous (or "monogamish") sexual activities up to this point have been emotionless and drama-free, I can't say with total certainty that there would be no emotion or insecurity involved were these things to take place.

The first thing I would like to try is a threesome with two men.  It's no secret that this is a major fantasy of mine, and has been for years.  There's something about the thought of two mouths and four hands traveling over my body that drives me wild, to say nothing of having two hard cocks to play with.  In my fantasy I am usually on my hands and knees, with one guy fucking my pussy while the other one fucks my throat.  However, it is increasingly common for this fantasy to feature double penetration.  I'm not sure that I'd ever actually attempt that, but it's really hot to imagine both men moving rhythmically inside me, one in my pussy and one in my asshole, driving me to one orgasm after another.  I acknowledge that the failure of this fantasy to come true is partially because I am worried that the experience would fall short of the fantasy I've created.

Another thing I think I would like to try is a soft swap with another couple.  For those not in the know, soft swap differs from full swap in that the former does not involve vaginal or anal penetration.  Everything else is fair game, from making out to manual stimulation to oral sex.  I'm not necessarily saying that I wouldn't consider full swap, but as we are relatively new to this I imagine we'd start slow.  I've already watched Jack interact with another woman, and while I was directly involved here I would not only not be involved, I would be doing my own thing at the same time.  As we are big fans of simultaneously watching and being watched, I imagine that sucking someone's cock while watching Jack have his cock sucked by someone else would be a great thrill.  This fantasy has yet to come true due to a lack of nearby couples willing to indulge us.  However, I can admit to feelings of jealousy.  I'm not sure why I have them, but I am aware that what turns me on in a fantasy might make me feel differently in real life.

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