Jack’s Answers

1. You have been invited to a lingerie party at the Playboy Mansion.

Do you accept? What do you wear?
Yes, I would accept.  Despite the fact that the Playboy Mansion isn’t really my scene, I can’t imagine not going, just for the sake being able to say I did.  I would wear a Tom Ford silk robe, and whatever I chose to wear underneath wouldn’t stay on for very long.

2.
(for women) You have been invited to a private dinner at Godfather’s Pizza by Herman Cain.


(for men) The wife of a Fortune 500 CEO, reputed to have had extramarital relationships, invites you to a private dinner when the husband is out of town.

Do you accept? Why or why not?
Sure.  First I would do a little research and ensure that her husband isn’t suspected in the murders of any strapping young men with whom his wife has been romantically linked.  Hopefully the wife is hot, and looking to fulfill a sugar momma role for a thirty-five year old sexual dynamo.  At the very least I have to assume the food will be good.

3. Charlie Sheen (for women) or Your favorite female porn star (for men) is making a movie in the city where you live. You happen to meet him/her, and he/she suggests you stop by his/her hotel for a drink?


Do you go?
I don’t see my favorite porn star making a movie in the city where I live, because I don’t live in the San Fernando Valley.  However, for the sake of argument I’ll pretend that some well-known porn studio is filming Golden Gate Gangbang on location and I happen upon the set, somehow make it past security and chat her up.  If I’ve make it this far she’s bound to invite me to her hotel.  I accept, and needless to say sex occurs because why wouldn’t it?  I have to assume that any porn star who invites me to her hotel room – certainly not just the hotel bar – is interested in auditioning me.

4. Your boss (of the opposite sex) who has been very flirty with you insists that when you’ve finished a project by working late or on a weekend you bring it by his/her house immediately?


Do you go? Yes or no.
Do you go alone or take a friend along?
I can think of a few incidents in my twenties when an attractive and flirty female boss did in fact ask me to stop by her house to deliver a file, or do something else that is today unnecessary thanks to the internet.  There was nothing untoward about her request back then, because without the sort of remote workstations that people who work from home use today, it was the only way to do business after hours.  And although every time I walked up the walkway to her front door I wished that she’d greet me wearing just a smile, it never happened.  This was ostensibly because she was married and had several children, most of whom were home.  But I frequently imagined that my dilligence was rewarded with an enthusiastic blowjob and a round of doggystyle some night when she was home alone.  Given reason to believe that my boss was attempting to seduce me, I would certainly go.  I’d probably go alone, as a performance evaluation seems to be the sort of thing that should be carried out privately.

5. You’re working on a political campaign. Late one evening, you get a call from the campaign manager saying the candidate (of the opposite sex) would like to see you right away in his/her hotel room.


Do you go? Yes or no.
Do you tell someone you are going there or keep it a secret?
What do you wear?
Yes, I would go.  I would have to presume that the meeting is job-related, although if the candidate was hot I would hope that there was a sexual aspect to her interest in me.  I probably would keep the meeting private, as Herman Cain will tell you that a sexual scandal can quickly sink political aspirations, and I would hate for my reckless tweeting to land both myself and the candidate in the unemployment line.  As for what I would wear, probably nothing too flashy.  I imagine that I’d wear a business suit or something else appropriate for what I assume is a meeting between employer and employee.  Fortunately, I look damn good in a suit.

Bonus: What’s the best invitation you’ve received? Why is it memorable?
I’ve been thinking about this question all day, and I’m having trouble coming up with something.  I’d love to tell you about the time that I was invited backstage after a U2 concert, but that never happened.  I’d love to tell you about all the dates I was invited on in which dinner and a movie turned into fingering under a street lamp and then thirty-six hours of sex at either her place or mine, but generally speaking when I was single I did the inviting and not the other way around.  So instead I will just make something up, with the understanding that I am trying to entertain rather than intentionally mislead.  When I was in my late twenties I was invited to participate in a high-stakes fifteen-hour Chemin de Fer tournament at the Monte Carlo Casino in Monaco.  Not only did I end up winning the tournament, but I also managed to thwart a band of international weapons smugglers, making my escape in a souped-up Italian sports car with a comely cocktail waitress in the passenger seat just as the casino exploded.

EDIT:  After this entry was posted, Jill brought it to my attention that after our third date, she invited me inside for a weekend of the best sex I’d ever had.  That counts, but my previous answer is more entertaining.

Jill’s Answers

1. You have been invited to a lingerie party at the Playboy Mansion.

Do you accept? What do you wear?
Yes, I would definitely go.  I would wear a sexy negligee, and beneath it a matching thong and garter belt with thigh-high stockings and fuck-me heels.

2.
(for women) You have been invited to a private dinner at Godfather’s Pizza by Herman Cain.


(for men) The wife of a Fortune 500 CEO, reputed to have had extramarital relationships, invites you to a private dinner when the husband is out of town.

Do you accept? Why or why not?
No, I wouldn’t accept.  This is partially because I do not agree with his political views, and partially because I love pizza, I have a standard for pizzerias, and Godfather’s couldn’t meet that standard if it was standing on an extension ladder.

3. Charlie Sheen (for women) or Your favorite female porn star (for men) is making a movie in the city where you live. You happen to meet him/her, and he/she suggests you stop by his/her hotel for a drink?


Do you go?
I do think he’s kind of cute, so I’m leaning towards going.  However, he seems to be insane and dangerous, and that has me leaning toward not going.  Can I go with the porn star instead?  I can think of a few porn stars I would like to meet, male and female, and I think I would enjoy that experience a lot more than I would enjoy a night spent hiding in a closet.

4. Your boss (of the opposite sex) who has been very flirty with you insists that when you’ve finished a project by working late or on a weekend you bring it by his/her house immediately?


Do you go? Yes or no.
Do you go alone or take a friend along?
Yes, I would go.  It’s my boss, after all, and I presume that if I don’t go, I might face disciplinary action.  (Then again, disciplinary action sounds kinda hot.)  I would probably go alone, unless I had a hot co-worker who was into threesomes.

5. You’re working on a political campaign. Late one evening, you get a call from the campaign manager saying the candidate (of the opposite sex) would like to see you right away in his/her hotel room.


Do you go? Yes or no.
Do you tell someone you are going there or keep it a secret?
What do you wear?
I think I would go, for the same reason that I gave in #4.  The candidate has requested my presence, and technically he is my boss so I would have to.  I assume that I have no reason to be suspicious of his motives in asking for me.  I would probably tell Jack that I was going, and not to expect me for dinner or, or possibly not even breakfast if the candidate was hot.  I would wear the panties, garter belt, stockings and heels that I said I would wear to the Playboy Mansion, as well as a sexy bra, but rather than the negligee I’d wear some sort of smart business attire.

Bonus: What’s the best invitation you’ve received? Why is it memorable?
One evening in August about five and a half years ago, Jack invited me to dinner.  When we left the restaurant, I was wearing a huge diamond on my finger.

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