Dad's House

Single Parent Dating
& Parenting Teens


Sexy Arrangement

sexy black bootsAs a single man who is in-between relationships, I make it a point to spend time with women, make sure there’s at least some feminine energy in my life. I have single mom friends who I grab coffee or go to dinner with, neighborhood moms who I chat with about school. I flirt (or think about it) with bus girls and coffee house workers (okay, not that often, but it’s good to flirt with a stranger every day!)

One thing can’t be filled so easily – physical intimacy. (That would be sex, in layman’s terms.)

While I’ve indulged in rebound sex and one-night-stands, I’m not a huge fan. I much prefer having a steady partner – if not a girlfriend, then a lover, friend with benefits, booty call partner. A sexy arrangement, agreement, desire to be together on a semi-regular basis.

And so it was with this intention that I met a woman online. We were both in situations where having a lover made more sense than dating.

For me as a single dad with half-time custody, dating is complicated. I won’t bring just anyone around my kids. And with soccer and lacrosse games, I’m with them more than half time. I have had girlfriends, so I know being a single parent doesn’t make dating impossible, just a little trickier.

The woman I met was in her early 30s, working full time, going to grad school at night for an MBA. She has no time for a boyfriend. But… she craves the sort of intimacy or passion that can only come from sex.

Or so I thought.

We chatted for an hour over drinks before I suggested we head back to my place. (When you’re auditioning a new lover, you don’t wait for third-date sex. First-hour sex is more like it.) This woman was hawt, if I may say so myself. Black knee-high boots, a mid-thigh skirt, sexy top. She was dressed to kill.

On the drive there, she asked what sort of arrangement I had in mind.

Hell, I didn’t know. Meet up twice a week? Once if our schedules don’t mesh? More if we could? For a sexy arrangement, more is certainly better than less.

I gave her the quick tour of my house, then we headed to my bedroom. I helped her off with her coat. I was thinking about lighting some candles when she got all awkward on me.

“Can we discuss terms first?” she asked.

Terms? WTF! Was this part of some graduate-level MBA course I never took?

She explained. “My last lover was an attorney. He helped pay my rent.”

Oops. That kind of sexy arrangement. Why hadn’t she explained that before? Maybe over drinks, on the phone, in email…

“I’m not looking for that,” I said.

“It doesn’t have to be my full rent,” she said. “But I’m a woman – I need something from you if you’re going to have sex with me.”

I won’t go into more details. Suffice to say, I helped her back into her coat and we parted immediately. On good terms – it was a simple misunderstanding by both of us. Though she might have mentioned her sexy arrangement idea up front.

While it’s rare for me to meet a woman who puts a price on her sexual companionship (like, it happened once with a girlfriend who figured, if I’m sleeping with her, I should basically give her my credit card so she can buy herself whatever she wanted. To which I said, um…. no) – I know it does happen. This particular MBA-studying woman insisted sexy arrangements were the norm for her in Silicon Valley.

I guess the next time I look for a sexy lover, I’ll be sure to say the only arrangement she should expect is one with flowers.

If even that.

If you liked this sexy arrangement post, you might also enjoy:

  |   Subscribe  |  © 2008-09 David Mott, DadsHouseBlog.com. All rights reserved.

January 8th, 2009 Posted in hookups | Tags: , , , | 49 comments

49 Responses to “Sexy Arrangement”

  1. Whoa! I didn’t see that coming! :D

    lisaq´s last blog post..Top 10 Dating Resolutions for 2009

  2. You should have offered to get her a new pencil case, what do you reckon you’d have ‘got’ for that?

    Personally I admire you, and others, for being able to strike up this kind of relationship, well not this exact kind, but physical relations without complications/hurt.

    SingleParentDad´s last blog post..Tried And Trusted

  3. Wow, never had that one happen! Although, admittedly, my current gf is pretty expensive…

    This is pretty basic prostitution. Not my bag, but I guess if you’re an unattractive guy and loaded this might be the way to go.

    Lance´s last blog post..Snowboarding, Sickness, and a Breakdown at the Grocery Store

  4. Holy shit! My jaw actually dropped.

    I have one girlfriend who is sort of like this, she think’s the man’s job is to buy you stuff. Now she is married and her husband gets hell if he doesn’t buy her nice enough things. Very odd to me but then again she is from another country originally.

    This girl should be on Ashley Madison or one of those sites where its clear you are asking for a sugar daddy arrangement. I can’t even believe she would expect that without pretty much stating it up front. Then again, I live in the midwest.

  5. Um…wow.

    I think that is outrageous. Isn’t the “friend with benefits” idea that both basically benefit from the same intimacy…NO strings attached?

    Or maybe that’s just playing into my current state of naiveté…

    Be well, Dads.

    mama llama´s last blog post..mistaken signals

  6. Wow, does she fool herself into thinking she’s not a prostitute? I’m not going to pontificate on the morality of prostitution, but this kind of denial really pisses me off. She probably doesn’t even think she’s selling her body. And that’s messed up. I can’t stand that kind of attitude… course, I’m dating a man who won’t let me pick up the tab on anything. I finally had to tell him I’m going to take him out for his birthday and I’m going to pay for the evening. But I don’t expect him to buy me stuff, take me on vacations, or otherwise purchase my affection.

    I’m poor but happy. I can live with myself.

    Solomother´s last blog post..Ann Coulter is no friend to single mothers

  7. What’s the saying, “there’s no such thing as a free lunch”?

    Yep, she should have mentioned the “fee” for her “services” upfront, unless you were being presumptuous to think that NSA sex comes at no cost. It always “costs” something, even if it’s just your time or emotional well-being … or, eventually, “drama.”

    When I was searching for a FWB shortly after my divorce, I still wouldn’t bed him on the first date. If there’s a connection there (hey, just because he’s not going to be a bf doesn’t mean he shouldn’t be studly!), then I didn’t have to worry about what date — first, second, third — we’d have sex. I knew it’s going to happen.

    Unless it clearly is a one-night stand, I’d be leery of a situation like yours and Miss Boots, for exactly the reason it didn’t work out. The hook-up mindset brought on by the Internet has resulted in many more, um, prostitutes (and willing johns) for lack of a better word.

    And, crap — I have a pair of boots just like the ones in the picture!

    Kat Wilder´s last blog post..He’ll be sorry he dumped me!

  8. Holy Crap! I can’t imagine what I would say if that happened to me! (with a guy) I’m sure that’s not nearly as common though. Just goes to show you really never know what you’re getting when you go online to find “dates”.

    MindyMom´s last blog post..Baggage or Blessing?

  9. Oh my!

    Gosh, I would think the arrangement of intimacy and sex would be “payment” enough. I would certainly work for me.

    Heh. I like the pencil case comment.

    T´s last blog post.."Click"= Risk-worthy?

  10. *Blink*

    Holy Hooker Batman! WTF. I can’t believe you didn’t throw her coat and her ass out the door!

    QTMama´s last blog post..Hmmm … Interesting

  11. Yikes! I’m not easily shocked, but this is all sorts of crazy weird. Maybe she’s an undercover cop? Nah. Interesting story and another reason why online dating sites are not for me. This is almost enough to put me off the flirt a day program, too, but I’m having too much fun practicing flirting without expectations or any follow up.

  12. What if you slept with her and welched on the payment? would she take you to court for breech of agreement?

  13. Oh second thought, perhaps you could have just asked how much her rent is and for a tangible sample of her work before making a decision one way or the other. Then you could have politely said, “no, thanks,” after sampling her qualifications?

    Just kidding! LOL!

  14. I dunno – in your shoes I would have suggested that an audition be in order before I agreed to any terms…

  15. Now… maybe that is an arrangement I should consider… a sugar daddy… of sorts…

    Exception´s last blog post..On Being Alone

  16. I’ve heard from friends about a few men in Silicon Valley/San Francisco who have a “kept” woman. I always thought that was weird. This woman was the first who ever suggested the sexy arrangement notion to me.

    She and I had an interesting chat after – she really wanted to know if there are women who would enter a FWB and not ask for money, and what did they get out of it? She really didn’t know the answer. I know there are female readers here who don’t like casual relations, but I think most can agree that the physical/emotional intimacy is one thing they get!

    Rob and Krn – I totally considered that approach. “Sample the goods”, then say no thanks!

    SoloMother – at one point she actually made a point to say she’s not a prostitute, and she even showed me her grad school student ID as “proof”. Whatever!!

    Krn – about the undercover cop thing. She had a fancy cell phone out of her purse and on the dresser, and it’s possible she was recording the negotiation part of the conversation. If she was doing that, then either she’s a cop or she wanted “proof” of a sexy arrangement agreement.

    What happened to a good old fashioned romp?!

  17. I know a “kept woman”; she was a cousin-in-law who has been in this way for over 20 years with the same man. He pays her apartment, she is in excellent shape, and she doesn’t have to work at all so as to be at his complete disposition. And yes, he is married with a family.

    It happens. But in that case it was a formal arrangement that has been maintained. Oh…and they live in California, too. Maybe it’s a CA thing?! ;)

    Be well.

    mama llama´s last blog post..mistaken signals

  18. Well, she IS going to business school…she’s an entrepreneur!

    Honey´s last blog post..Snowboarding, Sickness, and a Breakdown at the Grocery Store

  19. Wow, my jaw dropped too.

    First – for you having the guts to follow through on a “I just want sex” solicitation over the internet… that sounds so fraught with risk – you took her on a tour of your house? I’d be worried that she was scoping the joint to tip her thug friends off for an easy target. You are very trusting. (But maybe that’s how you do these things – I have no experience with this – soliciting for sex, that is!)

    And secondly, for her, for being a prostitute… and NOT KNOWING IT? How does that happen? That poor girl missed something when her parents were handing out morals. Oh well, you can never know what goes on in a person’s head unless you’ve walked a mile in their shoes…

    Here’s hoping your search finds you a normal woman to keep you warm at night.

  20. Being in your neck of the woods, Dear Dad’s House, I’ve heard of these uh, certain arrangements more than I care to remember… We’ve all heard of those Russian Bride events during which older, wealthy gentlemen show up to meet eye candy and take her home. It happens!!

    single mom seeking´s last blog post..Ann Coulter. “It’s your fault, single moms”

  21. ROFLMAO. I would have had to ask, “Do you mean pay for sex? Like if you were a hooker?” Sorry you can put your own damn coat on. Here’s a $1 thanks for nothing.

    Mike´s last blog post..Must Love Dogs 2

  22. OH MY GOSH!!!!! I can’t believe this. Too funny!!!! Definitely not what I expected!!!

    Attainingme´s last blog post..The Return of the Dance

  23. I agree with Kat that NSA is a myth. There is always a cost when giving part of yourself away or taking from others. And Dad, may I suggest that if you want a FWB that you might spend a little time becoming a *friend* first? In my experience FWBs have always evolved over time: after a LTR ends, or reconnecting with an old flame. What else are you after except services rendered if you jump right into bed before you even know her? Might as well be honest about your intentions and pay upfront.

  24. dadshouse- You write in a comment above:

    “She had a fancy cell phone out of her purse and on the dresser, and it’s possible she was recording the negotiation part of the conversation. If she was doing that then either she’s a cop…”

    There’s a part of me that would be pissed if this were not the case.

    If she were a “working woman,” what in the hell is she doing with her cell phone in YOUR bedroom on YOUR time??

    Wendy´s last blog post..Hollywood, here we come (until the drug addict showed up)

  25. Juliette – great advice!! Don’t forget the F in FWB. I’ve been in two long term FWB relationships. One was with an ex-girlfriend. One was with a woman where we went at it on the first date, had so much fun, we kept up the benefits without pursuing a friendship. At the time, that sort of sexy arrangement was good for both of us, but it didn’t last more than a few months. (She actually still texts me on occasion… but we haven’t met in a loooong time.)

    Wendy – I agree! Bad form if she’s taking calls. I didn’t get the impression she’s a “working girl”. I think she really did want an arrangement, though I’d be naive to think I was the only man she’s targeting. She could very well have other sexy arrangements going on right now.

    Mike – your approach is so simple and direct, it’s really funny.

    SingleMom in NE – we emailed, chatted, video chatted (g-rated), talked on the phone ahead of time. So there was some comfort level between us. Why she didn’t bring up “arrangement” until so late in the game is a mystery to me. Unless she wanted to written/recorded record. Who knows. Maybe she just expects every man she sleeps with will support her financially.

    Honey – who knows, maybe this was an undercover class project for her! Haha

    Mama Llama – that’s amazing. 20 years! Wow.

  26. There IS a name for a woman who wants to make a “sexy arrangement”. It’s WHORE. Sorry, but it’s sex for money and it’s prostitution any way you look at it.

    Twenty Four At Heart´s last blog post..Calling All Couch Potatoes

  27. I had to come back and read comments.

    What is scary is that “she didn’t know what you would get out of it” if it wasn’t some form of payment. WOW. Sad to think what appears to be an intelligent woman in her early 30s would not understand the value of an intimate relationship other than monetarily.

    I think you made a mistake here – You were not looking for a FWB. This was no “friend”. You met her solely for the purpose of establishing an intimate relationship (and of course, we can all argue the meaning of “intimate” but I’m being polite). What you want is a FB (F* Buddy).

    If you want a FWB, meet a woman, get to know them, become friends first. Or start fooling around with an existing friend. I have no issue regardless but I think you have to be clear with yourself.

    And college girls with sugar daddies are nothing new, I’m just shocked you ended up with someone looking for that arrangement. She sounds all kinds of shady but undercover cop? I’m pretty sure there is nothing prosecutable with getting a man to buy things for you.

  28. If she wasn’t a cop, what would be the purpose in recording the “agreement”? So you do her and agree to pay her rent, decide you’re done with the agreement 3 months later and she takes you to court? For what? Not paying her? Wouldn’t that be admitting she was a hooker?

    On another note, when I have done the FWB thing, both times the guys wanted it to get more romantic and eventually the FWB relationship ended because they didn’t get that. I think it’s hard to find someone who can stay on the same page when you’re getting physically intimate. For me, both times were after rough break-ups (otherwise known as transitional men)and although I wanted the physical intimacy I didn’t want more than that. Is it just me or is it easier for men to find a FWB than women?

    MindyMom´s last blog post..Baggage or Blessing?

  29. The scary part is that it’s likely something that has worked for her in the past several times or she wouldn’t have the gaul to ask for rent money. Not that quickly, anyway. Did she want a cash advance?

    Gennaro´s last blog post..Painted Monasteries Of Romania

  30. TwentyFour – absolutely! Funny that this woman didn’t see herself that way.

    MeThinks – you are right, I was looking for FB, not FWB.

    Mindy – I have found it’s very hard to do the FWB thing. I mean, if you’re friends, you’re friends, and if you suggest the FWB, it might backfire and end the friendship. Why risk it? FB’s are a little easier to find, but without the friendship, the relationship is beyond tenuous. Whatever the sexy arrangement, both parties need to be clear.

    Gennaro – great question! We didn’t get that far. But even if she’d allowed it, I really didn’t want to get involved with her at that point. (Though she was hawt… haha)

  31. Woah! Didn’t see that coming.

    justrun´s last blog post..And then the part where I give things away

  32. She doesn’t know what women would “get out of it” – a FWB arrangement – if not money?

    Hasn’t this woman ever had an orgasm?

  33. What? Didn’t you say you gave her a tour of the house? What more could she want?

    Jim Everson´s last blog post..The Big Questions

  34. I am in “wow” state just like everyone else – so nothing much to add there.

    But – I gotta say this – and please understand – I say this with absolutely no disrespect to you. But when I read this – I kinda thought “Damn you are really selling yourself short.” If you are the type of guy who can recognize that there is such a thing as feminine energy – you gotta do better than hooking up with a chick like this. Maybe look in a different pool – I don’t know. I’m not sure what I am trying to say – and I’m not saying it well. But anyway – not sure what it was – but this story really made me sad. Shocked first – but then sad.

    Amy´s last blog post..Journal 116: December 2008 Pros and Cons

  35. Amy – no offense taken. I totally understand what you’re saying. Believe me, I have turned every stone in looking for a long term partner. Online dating, meeting through friends, joining groups, doing activities, flirting with strangers. I keep looking. But I can’t survive as a monk – I need occasional contact. People throughout the ages have taken on lovers, and I don’t feel I am selling myself short in wanting one. I just won’t pay for a sexy arrangement. (At least not directly – others have noted indirect costs.)

    If I had proceeded with this woman, I’d be selling myself short. You’re right, she was plucked from the wrong pool. But I happen to think taking on a lover is fine. (Maybe I should hold out for third-date sex…)

  36. Oh, just chatted with MBA woman. She said that women who engage in casual sex are sluts who don’t cherish their body. (I won’t agree or disagree – everyone has their own opinion on that)

    But I did respond: whores who sell themselves for sex aren’t cherishing their bodies!

    I ran my tantra angle by her – that being present to the moment, being aware of rising sexual energy, and riding that energy from the root chakra to the crown – that is cherishing your body and its essence.

    She said no, that working hard for money is how you cherish your existence.

    And that sort of sums things up! So much for a sexy arrangement.

    Can you guess, we didn’t hook up?

  37. Obviously, she belongs on Wall Street. Who else can screw you out of your money so deceptively?

    I think the term ‘personal finance’ just took on a whole new meaning!

    Solo-Dad´s last blog post..A Solo-Dad’s Spiritual Journey: The Quest for Meaning in Life

  38. It’s so funny, but in reading your last comment Dad’s, both of you are talking about energy. Money is energy and sexual release is energy. She just is clearly more into one kind of energy!

    Anyway. I think it was bad form for her to wait until she got to your house. Maybe she thought you’d be so worked up that you’d say yes to anything. Seems to me that a good businesswoman would have discussed the terms up front, so as not to waste her time, and time is money, dontcha know?

    Leah´s last blog post..Crazy random dating story…

  39. FOR REAL!! OH LOL!!!!!

    Have you ever!!!! I actually have no words! “it doesnt have to be full rent” – oh goodness me Dave – this is CLASSIC!!!!!

    Laura´s last blog post..Interview with ME

  40. Leah – great insight! Money and sex are both forms of energy. You’re right, she wasn’t a good business person. But as a salesperson? Maybe she was doing ok. After all – a car salesman doesn’t tell you up front “this is really going to cost you!”. No, a car salesman gets you to sit down, be comfortable, really want it, then they sell you and upsell you. I mean, this woman dressed the part in her black boots and hot outfit. She absolutely tempted me. (Ah, temptation..)

    So, if she really wanted to close the sale on this sexy arrangement, she should have let things progress a little longer… haha!

    Solo-dad – ‘personal finance’, funny!

  41. OMG, I totally caught on when you started describing her outfit! LOL.

    I have to say, though, as I was reading the intro, I started to think, hey! Maybe that’s what I need – some single dad who has his kids half the time. Then I wouldn’t have to worry about the time suck I normally have with single guys. Thanks for the idea!

    But, um, yeah. I don’t think I’ll charge…

    Holly Hoffman´s last blog post..News Flash: Sex is a Distraction

  42. David-

    I found your blog via the listing over at Andy Bailey’s CommentLuv site and needless to say I like what I see, hopefully this comment will be the first of many.

    What she’s proposing is essentially prostitution, not that it really matters though, because dating itself often mirrors prostitution…the guy is supposed to pay for food, entertainment, parking, etc. What does that buy him besides something to do? Companionship / a good time (but you can have that for 50% off with a friend) so essentially what you’re paying the difference for is the sex.

    Our society seems to have informed women of this fact, and since this one wouldn’t be wined and dined, she figured she could just collect monetary compensation while investing less time…it’s a good business move, but clearly not what you were looking for.

    Just out of curiosity, did you meet her on a dating site or was it a craigslist type thing?

    Listen To Me Bitch´s last blog post..Foto Friday #1

  43. Hi Listen to me Bitch – thanks for checking out my blog! Love your insights so far. I agree that men should pay on dates, even if the woman works and is independent. That’s just my style (though I think it’s ingrained fairly deeply) I found this particular woman on craigslist. Nowhere in any of our communication was paying for a sexy arrangement mentioned. We were exploring an ongoing relationship as respectful lovers.

  44. Dadshouse

    If I found out that a guy I was dating had picked up total strangers from craigslist for just sex…he would be history.
    There is a huge ‘ewww’ factor there.

  45. Ditz – I totally get the “ewww” factor. I am not a fan of one-night stands. Do you have the “ewww” factor toward friends with benefits? Or toward a lover?

    As a single parent, physical intimacy is hard to find. I’d rather date and have a girlfriend, but short of that, I’d rather have a sexy arrangement with a lover than be a monk. This woman and I met with the intention of exploring an ongoing physical relationship.

  46. When I was in my 20’s (and single) I didn’t. But even then, I had a hard time staying detached. Maybe I just need a few more years by myself…

  47. Ditz – when I had a girlfriend, we had tons of sex. I miss that! I think any single adult, whether a parent or not, can go through “dry spells”. Women tend to weather those spells with more patience than men. But even if craigslist didn’t exist, there are married people on match.com and yahoo personals seeking sexy arrangements and affairs. There are people on myspace looking for casual hookups. There are singles bars and hotel bars in cities all over the US (and world!) where singles are trying to hook up. I’m not saying it’s the best idea, but it sure happens a lot.

    How did that Journey song go?

    A singer in a smokey room
    Smell of wine and cheap perfume
    For a smile they can share the night
    It goes on and on and on and on…

    Don’t Stop Believin’ video

  48. Love that you posted a Journey vid! Too bad I can’t listen to/watch the videos you post when my kid’s sleeping next to me. You’re not the only one not getting any these days. ;)

  49. oh my goodness. sex for rent. We know “what that makes her!” Yikes.

    movin down the road´s last blog post..Comfort Food Today

Leave a Reply

CommentLuv Enabled