What do you do when your ex-boyfriend pay you for sex?

Yes, folks, this happened. And not just any ex, it was the chef: one of my most tumultuous relationships to date. The man I was with the last time I tried to kill myself. Also the only man I’ve ever continued to screw (off and on) for over ten years. I hooked up with him maybe a year ago. Actually, it may have been two. Time flies and runs sort of parallel when it comes to Cash. He hits me up for sex a couple times a year, but I’ve been saying yes to him less and less. I love Cash, I always will—he’s like family to me—but it’s just not the same magic we once had. It’s old hat. Let’s also not forget that this is the man who refused to compliment me, and the man I rarely had orgasms with. As I’ve said before, I’d rather jack off than have mediocre sex, and it’s not like I don’t have sex. The times I’ve said yes in the past were mostly due to me wanting to get fucked by a big dick that wasn’t a client. And there’s always been a mutual attraction. In fact, Cash held the record—until recently—for one of my all-time favorite dongs. He had the title for a long time. However, over the past few years, I’ve been craving spark rather than just the ol’ in and out—authentic passion. And now that The Crush is in the picture (with his beer can cock), I haven’t wanted to fuck anyone else without money being involved. So, there we are, with me being a strange limbo state: unable to get laid by unable to get laid by the man I want, and getting hit up by ex’s for sex.

Cash text me on Easter for a quickie. It wasn’t super appealing. He wasn’t even pretending to want to get a drink or hang out like we used to. And I’m not saying there’s anything wrong with a straight-up booty call, but if all I’m getting is a good penis out of it, well, I have dildos that I can come on. So, why? And why would I shave and go through it for free? I think it was around this time last year that him and I were in the same predicament and I proposed the idea of him giving me money. He was extremely turned off that I had said that. While I didn’t blame him (he’d been getting the cow for free for a over a decade), I also didn’t see the harm in it. To me it was a win win. Just throw down a little dough and I’ll never say no to you again, bro. Obviously I’d give him a family discount. But he didn’t see it that way, so I let it go. I never returned his text on Easter. I was considering it, but knew that if I was hemming and hawing that much, I already had my answer.

Then, he text me on a Sunday morning a couple weeks later: “Get together today? $”

I responded, “Hi Babe, was that $ a typo? If not, that sounds like good kinky fun to me.”

“What time?” he said.

“Is that a yes to my question?” I asked.

“Let’s do it.”

I hate when men do that. Why couldn’t he just answer me? He knows I’m not a vice cop. Why make me dance through hoops? So tiring. I put my phone away and went back to the business of searching for items at the flea market. Then an hour later, he writes, “How about one-ish?” No answer on the money. Infuriating. I decided to make him wait—hoping he’d get the picture and answer the fucking question. That’s one of the really great aspects of our long, sordid history—I don’t owe Cash a thing.

I met my best friend Hattie for brunch. She’s been around for the entire Cash saga, so I gave her and her husband the lowdown. She composed a text for me (she loves doing that when I’m at a loss for words). I approved of what she wrote—although it was a little more business minded than my interactions with Cash, it addressed the money issue in a nice way. I hit send. He responded, “Yes, and yes, but I’m not rich.” I laughed at that. I didn’t need to discuss the nitty gritty, I just needed to know he was coming with paper. I told him cool and asked if 4 p.m. worked. He said it did. I went back to the business of brunch. Holy shit, I was going to fuck my ex for money! I was thankful that I’d be buzzed for the deed as this was going to be a first for me.

I got home an hour or so later and started tidying the house up. It’s been a disaster lately. Between the photo shoots, no one coming over, and me not giving a shit, stuff has been less organized than usual.

I put a load of laundry in, but I didn’t have time to wash my bedding, so I threw my comforter cover in the dryer with dryer sheets. I know he wouldn’t complain if my bed smelled like me, but that’s just the kind of girl I am. I could probably put a 10x10 piece of fake grass on my bed and I bet he wouldn’t say anything. I jumped in the shower. I didn’t wash my hair though, fuck that, I was leaving the following morning at the crack of dawn for a work trip; Cash would have to deal with day old hair. I did have one slightly amusing dilemma once I got out of the shower: what do you wear for a man who is about to pay you for sex, but who has also seen your stomach get pumped? I considered lingerie for about two point two seconds, but knew it would be way too obvious. Too working girl. On the flipside, I didn’t think I should wear my cut off sweatpants. Even though—as I’ve said time and time again—I don’t think he’d give a fuck. Yet it never seems to stop my inner dialog, or me trying for the perfect thing.

I settled on a pair of cotton mini shorts I used to wear at the strip club (I think they’re made for teenagers), and a flimsy open back tank top with the British flag. Easy access. I put minimal makeup on; just enough to say, “I care”, but not so much to scream, “you’re a trick”. I poured a whiskey neat and a pickle juice back. Which probably wasn’t the smartest decision for breathy reasons, but it’s what I was craving. I was a lightening bolt of nerves. The whole thing was so odd: on his way was a man I used to fuck a minimum of twice a day, but never under these pretenses. I didn’t want to get drunk, I was seeing The Texan for what was sure to be a liver-damaging trip.

I waited. He knocked. We hugged. I could tell he was a little nervous too. I joked with Hattie about whether I should ask for the money upfront or not. “Should I tell him to put it on the table? This is so weird.” He didn’t bring it up, so I did either. I trusted he would give me the dough. Three very clear texts, how could he not? Cash is a lot of things, but a blithering idiot isn’t one of them.

We sat on the couch and caught up. “How’s life?” he asked.

“Good. Same ‘ol shit. Slaving away on the writing. Traveling a lot. You know. You?”

He told me about the new company he’s working for, and the new restaurant he just opened. He said things were going well, including things with his girlfriend and daughter. I’m used to hearing about his life. They started hooking up as we were painfully dragging things out, trying to break the habit, oh so many moons ago. He’s much more mellow now, and they seem to be in it for the long haul, but like most long-term couples, their sex life has dwindled...enter the pussy slinging ex!

I have been against cheating for most of my life, and yet I’ve slept with Cash off and on all these years. I know she’d probably lose her shit if she ever found out, and I know this is going to sound like the biggest justification of all time; but he was mine first and for some reason I’ve never felt guilty. Him and I have always been drawn to each other. And although it’s been less for me these past couple years, he’ll still always have that thing for me. We’ll always be connected on some level. I could tell there’d be no major boozing or drugging for this get-together (as we have in years past), although he did lament to having a shot of whiskey with me. We did a shot, including a pickle back, and he asked if we should get naked. “Let’s do it”, I said.

I had music playing in the living room, but forgot to put some on in the bedroom. It was too quiet back there, but I could tell time was of the essence for him, so I let it be. Oh! I forgot, when I was cleaning and getting the place “fuck ready”, I contemplated on whether I should spray my bed with the sweet-scented pheromone spray (especially made for sheets) that I do for the rare client that comes to my house. I decided against it. Again, it felt too overt. This man knows me. He knows my smell. He likes my smell.

We took our clothes off. His cock was already at full-throttle. That will never cease to amaze me: that men can be so excited just at the prospect of sex (without foreplay). I straddled him for a tick on the couch and he grabbed my tits—he’s one of the few men in my life who’s a boob man—but it was hardly what I would call hot and heavy foreplay. It’s always such a trip to get naked with Cash. I was so much thinner when we were together. That body is long gone. Hell, I was even in better shape when I saw him last, a mere two years ago. He has a little extra dad weight himself, but considering he was anorexic before, his extra weight is a good addition. I’m not trying to beat myself up. I’m simply stating facts. I liked my thirty-eight-year old body more than my forty-five one. He never seems to care. He’s seen the progression.

He sat back slightly on my bed, lying on his elbows. I dropped to my knees and put his cock in my mouth. It was even bigger than I remembered if that’s possible. The last few times I’d seen Cash, we’d been drinking—both separately and then together—whereas this time we were pretty sober. His cock was in full glory. No wonder why I put up with all of our bullshit for all those years. I was cockmatized. Even still, a beautiful dick doesn’t replace chemistry. He moaned. I surprised myself by taking more of it down my throat than I thought I would in that position. Something about his dick, I’ve always managed to deep throat him, including that time in the front seat of my GTI.

“Remember that blowjob in your car on Rampart?” he asked.

I smiled because we had been thinking about the same thing. “I’ll never forget it.”

“You said it was the best head you’re ever given.”

“Pretty much” I said without conviction.

I don’t know about “best” but it was amazing, and mostly it was astonishing because of the position: he was in the passenger seat; I was squished on my knees on the floor in front of him. This position goes against all my advice on the cock-to-throat positioning, and yet I was balls-deep with ease. Like ease. I could have read a book aloud while going down on him at the same time. Shit was magical. Okay, that’s an exaggeration, and makes it sound like he has a pencil dick, and we know he doesn’t. Point is, he came down my throat while I was muffling most of his cock.

He pushed himself fully on my bed with his head on my pillows. I took my panties off and straddled him. We kissed. I kicked myself for not doing the oh-so-sly saliva on pussy trick while I took my panties off. I pushed my opening softly against his rock-solid erection, and to my amazement, it slid past my lips after just two small back and forth movements. I wasn’t remotely turned on, but I’m also not getting any real action these days, so I was also sort of looking forward to this.

“God damn, I love your pussy” he said with abandon and conviction. I wonder if it’s because I haven’t had children? He lifted the thin tank top over my head, and my tits were instantly in his giant hands. I figured I’d rock him for a few and then we’d roll over, but within four damn minutes he asked if he could come.

“Of course, babe” I said. I lifted off him and he came on my pussy and our body parts. No, we don’t use condoms. I asked him if he’s been with anyone else (besides his girlfriend) on our way to the bedroom and he said that I’m the only one he’s slept with outside of his relationship in years.

You’d think he’d have some questions for me, but he didn’t—men rarely do. Lucky for them I’m pretty paranoid about STD’s and get tested regularly, as well as being safe. I had recently gotten a clean bill of health, so I felt he’d be okay. Well, as best I can...there are no guarantees.

He was a bit humbled by the speed in which he came. I reassured him it was fine, but, truthfully, I was a little bummed. I mean, shit, I figured I was at least going to get dick-downed for twenty minutes! But obviously I’d prefer him coming quickly than not being able to at all—although that’s never been an issue for him. He got dressed and reached into his pocket. I knew what the gesture meant. He sort of fumbled his words; something about not wanting to pull out too much at the ATM, so he’d owe me. I wasn’t thrilled with this. I know he could have figured it out if he really wanted to. “OK” I said, “just put it on the dresser, I’m not going to count it now. Thanks, honey.”

I went to the bathroom. I had already peed and washed up, but I wanted to give him a little cordial space between the sex and the money. We never did discuss the actual amount. He had asked for the family discount via text, but that was it. I had a floating number in my head of what he’d give me. We’d see.

He broke the silence when he stepped into the living room dressed and ready to go, “That wasn’t so bad, was it?” he said.

I laughed, “Of course not. That’s not the issue. It’s the time and shaving...” I trailed off. There’s not a fabulously smooth way to explain to your ex why he needs to pay for the pleasure. I flipped the script, “You’re a super busy man, you know how precious time is—this is a win win.”

He smiled and grumbled. I don’t think I sold that one. We hugged at the door. I told him to text when he wanted to see me and that we wouldn’t need to discuss the financial part again, now that it’s known. He left. I went to the bedroom to count the crumpled pile. It wasn’t as much as I had hoped for. I’ll make sure to tell him to space out his ATM withdrawals before seeing me next time. Either way, this isn’t a horrible development. Let’s see how he handles it...and if he’ll want to do it again.

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