This was one of the most difficult-to-answer Formspring questions we’ve yet been asked.  We have many personal acquaintances with whom we would be okay having sex under the right circumstances.  It was difficult narrowing our lists down to just three, though for the sake of adding value to her answer, Jill named three men and three women.  Rather than assigning the following individuals fake names, or identifying them by initial, we have decided to identify them by a number and a brief description.

Jack’s Answers

1.  Female, age thirty-four.  This is “M”, our former third.  I’ve known her for twenty years or so, and she’s always been a good friend.  And while I technically have had sex with her (oral counts!), I’d love to have vaginal intercourse with her.  (Or anal – I’m not picky.)  The fact that she’s in a relationship and it’s going well seems to indicate that I won’t get my wish anytime soon.  On the other hand, she told me soon after her relationship began that her boyfriend told her he was open to the idea of an MFM threesome.  While I would be down for this, it hasn’t come up again in the last several months.

2.  Female, age thirty-six.  Another friend I’ve known for around twenty years.  This person is the wife of Jill’s #3.  How we’ve never had sex in all of our years of friendship is a mystery to me; I’ll blame it in part on the fact that she was usually in a relationship when I was single, and vice versa.  We came close one night, though my interest in sustaining the bad relationship I was in at the time – a relationship that ended not long after, much to my frustration – meant that we both parted company unsatisfied.  Since then, we’ve had same-room sex together, we’ve webcammed, and we’ve had phone sex.  I should’ve just fucked her that night.  

3.  Female, age thirty-one.  The sister of one of my ex-girlfriends, and the wife of Jill’s #2.  I’ve been attracted to this person for a long time, even when I was dating her sister more than a decade ago.  She’s beautiful, fun, and fairly open about her sex life, though as Jill mentioned in this week’s Wanton Wednesday, she made it at least until her late twenties without ever using sex toys of any kind.  (Not that this makes her less attractive.)  She is the sort of person with whom we can watch porn in a relaxed, though fairly sexually-charged, atmosphere, or trade erotic stories.

Jill’s Answers

1.  Male, age forty.  Husband of my college roommate, who is my person #4.  I’ve been attracted to him since we met in college.  He’s a nice guy, he’s a lot of fun to have around, and he’s sexy.  When my roommate and I would talk about our relationships, she had much more exciting stories than I ever did.  To hear her tell it, he was always pretty adventurous in bed, and while I’ve not yet had the pleasure, the four of us once had same-room sex in a hotel.  Although the lights were off, it sure sounded great.

2.  Male, age thirty.  Husband of Jack’s #3.  I’ve known him almost as long as I’ve known Jack.  He’s a reliable friend, handsome, and very comfortable talking about sex.  In fact, we’ve had many instant messenger conversations that wasted very little time in small talk before moving to more sexual topics.  He’s flirtatious, though not nearly as overt about it as Jack.  He’s also seen me masturbate, and by all accounts he enjoyed it. 

3.  Male, age forty-four.  Husband of Jack’s #2.  A sometime commenter on this very blog, he has expressed attraction to me, and hinted that he wanted to watch us have sex, and possibly have a threesome with us.  While he was separated from his wife a few years ago, he got to watch, but made no attempt or request to join in.  It was actually kind of disappointing, though Jack and I are both certain that he was just trying hard to be respectful. 

4.  Female, age forty.  My college roommate and the wife of my #1.  Another former commenter, this person is in many ways the ideal of free-spirited sexuality that I aspire to.  She is physically beautiful and open-minded, and her sexual adventurousness helped to bring me out of my shell when I was younger.  Without her, I would never have masturbated with a piece of fresh produce.

5.  Female, age forty.  My best friend since high school, and someone I consider family as much as any of my siblings.  We are very close, but despite the fact that we have seen each other naked, I am sure she’s the person on my list least likely to be interested in sex with me.  She is much more sexually conservative than any of the other five, the person least likely to discuss sexual matters (although we have on occasion), and although I hate to admit it, the person most likely to judge Jack and I for some of our sexual wants and needs.  Still, I think she’s sexy, and I’d do her in a heartbeat if she was interested.

6.  Female, age forty.  My oldest friend.  We’ve known each other since age five.  Like my #5, I consider her a sister, as our closeness transcends mere friendship.  The best way that I can describe her is as the middle ground between #4’s bohemian nonconformity and #5’s conservatism.  She is someone I’ve always been able to party with, or tell secrets to without fear of judgment.  In the past, I’ve referred to this person as “P”.  You can read more about our friendship here.

If you want to ask us anything, drop us a line on Formspring, or use the handy Formspring widget on the right-hand side of our blog.  We like sexy questions!