Much thanks to Sweeten Dirty for this week’s TMI Tuesday questions.

Flesh and Fantasy

Jack’s Answers

1.) What was your biggest fantasy once you discovered sexy things?
Without a doubt, my biggest fantasy has always having two (or more) women at once. It’s something of which I became aware relatively early in my sexual development, and which I always found appealing. As I have stated elsewhere on this blog, just about everything I’ve done over the course of my life, every decision I’ve made, I’ve done so with the thought of making this fantasy a reality at the forefront of my mind. “Studying a particular discipline? Choosing an apartment? Picking out a tie? Yes, every one of these decisions and countless others were made with the thought of pleasing two woman at once, and of course being pleased by them as well.” You can read more about the unlikely source of this fantasy at this link.

2.) Did you get to do said fantasy, and if so would you do it again?
I did achieve said fantasy, though I’m almost sorry to say that it didn’t happen until I was well into my thirties. I would definitely do it again, and in fact I have. Many times.

3.) Was it as good as imagined?
The first time it was better than imagined, and that’s saying a hell of a lot because it was a fantasy I’d been entertaining for more than twenty years. But our third was a very close friend, one I’d known for years and to whom I’d long been attracted. She was completely respectful of Jill’s boundaries – because I have none – and said and did everything exactly right to ensure my wife’s comfort. I don’t think I even fucked her that first time, and that was okay. In the wake of this experience, nothing really changed within our friendship; though playing together seemingly brought the three of us closer, it didn’t get weird, and even though it’s been awhile since we’ve had a threesome with her, we love hanging out in groups and knowing we’ve got this secret about which no one else knows.

4.) Describe said fantasy.
Let’s see. Me and two other women. Doesn’t matter who. Clothes being taken off. Huge empty bed suddenly taken up by the two women, whom I pleasure with hands and mouth for as long as they can stand it (or alternately one woman lies on the bed while the other woman and myself pleasure her, and then they switch). Eventually I get on the bed and they pleasure me. At some point penetrative sex occurs; ideally at one point one of the women would straddle my face while the other rides me. As it’s a fantasy I entertained for many years, there were variations as I learned more about the ins and outs (so to speak) of sex. Additionally, the location changed occasionally. As a child, I thought you had to have sex in a bed. Still, the fundamentals – making out, manual and oral sex, penetrative sex, etc. – were pretty consistent.

5.) What is your biggest fantasy now?
Honestly, probably just to meet and have sex with a bunch of our fellow bloggers and the friends we’ve made on Twitter. Like, one per month, say. That would be nice.

Bonus: Something you would NEVER do.
This is a hard question to answer, as never is pretty limiting, isn’t it? There are things I’ve done that I thought I’d never do but eventually did, including a threesome with another man. When I was younger and more insecure, that squicked me because I didn’t like the idea of sharing my partner in that fashion, nor was I necessarily comfortable being in a sexual situation in which another man was involved. The thought of the other guy being better than me, having a bigger cock than I have, or perhaps threatening my relationship, was difficult to accept. But as I’ve grown older and more secure in myself I realized it was something I could handle, and handle it I have. Though we aren’t regular practitioners of BDSM, there are certain aspects that we enjoy, and yet I can’t see myself ever trying breath play. For myself, and certainly for Jill, that’s a hard limit right now. And currently I’m not into the idea of having sex with another man; it doesn’t do anything for me, nor does it excite my wife. And I’ve given the matter some thought! I’m not just dismissing it reflexively as some men are wont to do. Still, I can’t say never to these things because who the fuck knows how I’ll feel in a year? I am relatively confident, however, that I’ll never be interested in coprophila, nor any sexual activity that involves minors or others unable or unwilling to give consent. I’m pretty sure that will never happen.

Jill’s Answers

1.) What was your biggest fantasy once you discovered sexy things?
Do I have to pick just one? Because in my formative years the two fantasies that turned me on the most were having sex in public, and having sex with two guys at once. Though I really do enjoy having sex with women, it’s more of a recent desire. Public sex somehow seemed more normal given my values and upbringing. I felt like if I was caught having sex in a public place it might embarrass my parents, but at least I was only having sex with one guy. Plus, it really satisfied my exhibitionist nature. However, the thought of having sex with two guys at once was much more taboo, and that made it so much hotter.

2.) Did you get to do said fantasy, and if so would you do it again?
Yes to both! I would definitely do either one again, though regarding public sex I am a bit more mindful of the thought of being caught and what it might do to my career. Still, yes. I totally would.

3.) Was it as good as imagined?
The first time I had sex in public, it was so exhilarating! A fuck buddy and I had gone out for a late-night walk and ended up at a local park. We went up on the play structure where we made out. We slowly sank down to the floor, and he hiked up my skirt, spread my legs, and began to finger my pussy which was by now soaking wet. He brought me right to the edge, then slowed down and slid my saturated panties off. Then he went down on me, and his lips and amazingly skilled tongue drove me to climax more than a few times in rapid succession. I moaned his name, my juices dripping down my thighs and my ass. He pulled me up to my feet and I helped him take out his cock. I would have liked to have sucked it, but at that point all either of us wanted was to fuck. He pushed me up against the railing and I put my leg up, and he fucked me hard. I stared out at the night, enjoying his strong hands on my hips, and the feel of being so full, but part of me really wanted a crowd to gather at the edge of the park, or even right below the play structure. It was really late, so I knew it wasn’t going to happen, but the thought turned me on. Eventually he lay me back down and got on top of me. I clasped my legs around his waist and put my hands on his shoulders, urging him deeper. It didn’t take him long to come. So hot! As for the threesome, it was very good, and every bit as exciting as I hoped. It just didn’t go on for as long as I would have liked.

4.) Describe said fantasy.
My sex-in-public fantasy involved me having sex in any public or semi-public place. It might have been in a storefront window, on a park bench, or the middle of class. In other words, it wasn’t behind closed doors or otherwise completely private. Usually I was having sex in full view of onlookers or at least passersby. At the very least, there had to be the possibility of being observed. But any observers were always excited by the sight. I wasn’t, and still am not, turned on by the thought of offending anyone. Ideally as the crowd watched they got turned on enough to masturbate, or have sex with a partner. As for my threesome fantasy, I just liked the thought of having two men to make out with. Two mouths and four hands all over my body. And while I was really into the idea of receiving so much pleasure, I knew that having sex with two men would really allow me to explore my submissive side. I liked the thought of getting on my knees and sucking both cocks, either one at a time or both at once, and I really loved imagining one man fucking me doggy style while the other grabbed my hair and fucked my mouth.

5.) What is your biggest fantasy now?
As with my first answer, I can’t exactly narrow it down to one. I have a few male friends who I’d really like to have sex with. I describe three of them in this post, though there are more than just three. I enjoy fantasizing about these men because, like Jack, I really like variety, and it is unlikely that any of these guys’ wives would give them permission to sleep with me. However, there are a couple single guys among my fantasy pool. As for another fantasy, the last few years I find myself more and more turned on by the thought of double penetration. Before that, it was a pretty much nonexistent aspect of my threesome fantasies, in part because it somehow seemed too dirty – they only do that in porn films, right? – and later because of a bad experience with anal sex. I find it so hot to imagine both men filling me at the same time, their cocks alternating pistons moving in and out, one in my pussy and one in my ass. Although I can’t imagine being able to pull this off logistically, the thought of all three of us coming at the same time has me so turned on right now that I need to change my panties.

Bonus: Something you would NEVER do.
Cheat.

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