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"SUGAR DADDY" #3 A very expensive massage

I just left arrangement date number three. I swear these men are getting stranger by the second. I guess they’ve always been weird. I’m just noticing it more now because I know I’ll write about it later.

I met date number three at a hotel bar in Newport Beach. Luckily he was only guy in the bar area and was facing the entrance, aiding in the, “is that him?” department. He looked like a wee holder version of his photos—but since I don’t give a rat fuck, it was merely an observation.

I walked up to him. It was 3 p.m. in July, aka, bright as shit. I was wearing a short, black, shiny dress (too much for 3 p.m. on a Thursday), and black patent leather heels. I felt simultaneously over-dressed, hooker-y and old Jew at a funeral. Exactly what every hooker approaching forty-five wants to be feeling as she saunters up to a meet n’ greet. Awesome, let’s do this!

Anyway. First impression went well: He smiled. How sad is it that a simple smile indicates, A) I don’t think he’s going to kill me and B) He might want to fuck me. Crazy times we live in.

We do the, I think it’s you nod, and I take a seat in the tall chair opposite him. I was nervous and sweaty, and feeling every bit of my age. Fucking 3 p.m. It’s the major downside to seeing married men in their hometowns. His demeanor was pleasant, and he told me I was “gorgeous” almost right off the bat, which helped ease my pain. Be nice people! Small gestures go a long, long way. I noticed he was drinking a Diet Coke from a bottle he must have brought in from his car. I had a feeling I knew what this meant—that he was clean and sober. The server came over and I ordered a glass of white wine. Somehow white wine is becoming my hooker meet n’ greet cocktail of choice. Although I’m not sure why, I don’t normally drink white wine. I think it’s because it seems like a socially acceptable daytime spirit. But it makes me feel like one of the reality housewives. I might as well order a fucking tequila sunrise and really show my age. Cue the soft rock! If I’m trying to exude youth, I should start ordering gin and tonics.

He got a double espresso. Sober, no doubt about it. Most people would have a least one drink in this scenario. After the bartender left, I asked, “Do you not drink?”

“No, I’m sober, but please drink. Do you want a martini? Let’s get you a martini.”

I chuckled. I figured martini’s used to be his thing. He probably wanted one, so he pushed it on me instead. Or perhaps the white wine was too wife-like. The bartender came around with my wine and his espresso. The “date” commenced. The difference with this one was that I knew we had a room upstairs, and that he had brought cash in the amount agreed upon. Guessing he wouldn’t want to eat the hotel room cost, I felt confident in this guaranteed hookup; I had learned my lesson from those previous two. He proceeded to tell me about himself while I drank my wine. I liked his energy, even though he didn’t seem entirely comfortable in his skin. But then again, from an outsider’s point of view, I probably didn’t look all that cozy either.

He asked how long he had me. A simple question, but again, something sweet and flattering in the way he put it. I’m telling you, it doesn’t take much. I recalled him mentioning a 5 p.m. family function, so I said a couple hours. But as it was coming out of my mouth, it hit me that the family thing was actually from the first time we spoke of meeting and that I could have said an hour! It’s not easy keeping all these men and schedules straight.

An hour is plenty of time for a first hookup. Hell, even an hour can feel like an eternity for the actual sex. I was contemplating this when he ordered me a second drink, and offered that we go upstairs. I came out of my fog. I needed to finish the first glass of wine quick.

As I did that and the bartender poured my second (comically large) glass of wine, my date was saying something about our suite on the 10th floor. Yadda yadda. We could head to the basement for all I care. Rooms/suites rarely impress me in my hooker world. Not to sound like an ungrateful cunt, but I really couldn’t care less. Here’s what’s important: no bed bugs, be nice, hand over the money without prompting (a little more than what we agreed upon would send me over the moon and give you extra blowjob points), and have a good time! I’d fuck a client in the back of his Jetta as long as those things were taken care of. But I can’t say that to Mr. Mister. So, I smiled, acted impressed, and walked my big glass of mid-life through the lobby while thinking the same thing I always do: Does every person watching us right now know I’m a hooker?

I was in a mumbling mood and his hearing wasn’t great—not a fantastic combo. He kept asking what I had said, and since it was basically nothing important, I wanted to say, “Please tell me there’s a bucked of cyanide at the end of this hallway”. Instead, I said, “Sorry, honey, I was just noting the strange windows at the bottom of the floor.” Not an untrue statement. At any given point in time, I have about a million or eight consecutive thoughts swirling around in that thing above my shoulders.

None of it mattered. I could have said my vagina liked the wine. We both had been around the block and knew the score. The room was paid. I was getting money and he was getting laid.

The room was a one-bedroom suite with double French doors in-between the living room and bedroom. He played an alt-rock Pandora station on his cell phone. He had asked me to wear a garter belt and stockings, but it was really hot out, and I didn’t want to make the long drive in stockings, so I had both items in my purse. I told him this, and that I was going to shimmy into said items. He didn’t seem to care, but I figured, I had bought them for him and if it helped turn him on, why not. Unfortunately the bathroom layout was not ideal. It was long with two entrances, but the area with the sink—just off the bedroom—didn’t have a door. And the toilet was on the other side and only divided by a sliding door. How was I going to sneak in a quick sink wash without him knowing? So annoying. Truthfully, I was weirded out by the whole thing. It’s so much better being able to relax and flirt at a bar in the evening and then go to the room. This was too business-like. I came out so that I could sit on the bed and attach the stirrups (he was on the couch facing me). He complimented my legs, and then said, “Don’t worry about the belt, but leave the thigh highs on.”


I walked over to the couch and gulped some wine, and then I kissed him. I was in a weird position though. Looking back (hindsight is a real cunt), I should have straddled him. Duh, I was a stripper for twenty-three-years, and a man was sitting on a couch. It was a no-brainer…I guess I left mine in the car. Instead, I was sort of sideways on my hands and knees like a jackass. Have I mentioned how much I hate these first-time hookups? It’s an audition, and you know how I feel about those.

What happened next? I think he stood up to pee. When he came back, he undressed—he had a good body for his age, stocky and strong—he stood in front of me. I got on my knees and started sucking his cock. Good. This I can do. I was giving him the business. He was moaning and grabbing my head. I got the feeling he could come—please lord, yes—but of course he didn’t. No man wants to pay good money for a four-minute blowjob. No way he’d allow himself to come that fast. Too bad though—turns out he should have. He ordered me to lie on the couch while he fetched a condom.

“Would you like to go the bed?” I asked.

“No, stay there.”


He came over and I could see that his dick had decidedly gone down from the condom roll, and what I guessed to be lack of blood flow from age. I licked my fingers and wet my pussy lips. He pushed himself in and fucked me with my legs up near my ears. Horrible position for my unflat belly, pretty much the worst. I did my best to suck it in. Also, my tits were trapped in an awkward position under my thighs. I tried to free them a little while also grabbing them in what I hoped was a sensual manor.

The whole thing wasn’t bad per se, but it wasn’t great either. I was doing kegel exercises and praying he’d want to move to the bed, and out of this position ASAP. I was thinking he’d be better off (dick wise) if he were standing behind me, but I could tell he was the type to control the wheel, so I kept it to myself. Plus, he was asking if I was his slave.

After maybe seven minutes, we finally moved to the bed. I began to worry he wouldn’t be able to come. I think I offered to get on my hands and knees, which he declined. He laid on his back with his semi-erection and the sweats started to kick into high gear. The room was too warm, but afraid of seeming pre-menopausal—yes, I’m a freak of nature—I said nothing of it. Due to a combination of nerves, pills, age, room temp and lotion, my skin was clammy.

I went down on him, trying to breath life back into his dong. Ugh, why didn’t he just come in my mouth before? It was sort of doing the trick, but not totally. I could sense we were thinking the same thing. Especially when one of us is dead sober, there was no escaping the brutality of the situation. As I was contemplating blood flow charts and sticky skin, he asked, “Do you give backrubs?”

“I can”, I answered.

“I’m really tight in my neck area. I’m going to take this condom off, if you could rub my shoulders, that’d be great.”

I knew this probably meant the audition was over and that I didn’t get the part of mistress. Oh well. The cash will go to good use. I guess in the scheme of things, it was an easy gig. But I’m looking for an ongoing thing. He went to the bathroom, when he came back, he got on his stomach. I massaged him with nothing on but the stockings, and wished I had a hair tie. I looked at the clock. We were only thirty-minutes into this thing. Shit. Why did I have to say two hours? I cursed myself and continued massaging him. I think he fell asleep at one point and farted a little. Yay my life! I was sort of hoping he’d stay asleep and I could just watch TV for an hour, no one the wiser. I mean, obviously he’d know it wasn’t a dynamic fuck, but perhaps he’d think he got his money’s worth. Why do I fucking care so much about being fair to all of mankind? It’s an annoying trait. It’s interesting how sex with one person can be hot as fuck and super fun, and runny scrambled eggs with another. Anyway, his phone rang and woke him up. Whatever it was, he needed to go. Thank you, Jesus!

I peed and as we got dressed he said, “Well, you didn’t make me come.”

I felt like throwing my garter belt at him. Like, hey motherfucker, I tired. But instead of acting like a lunatic, I said, “We could have tried different positions. It felt like you were close when I first was going down on you.”

“I was.”

“Silly, you should have just let it happen. Do you want me to get on my knees?”

“Nah, I gotta go. This was probably not a match, but I think I know someone that would be good for you. He’s a billionaire. I showed him your pictures, and he said if we didn’t work out to let him know.”

“Sounds wonderful, thank you.”

He hesitated a second and added, “He’s a bit heavier.” Which, in Southern California means he’s twenty pounds overweight.

“That’s not a problem”, I said.

We hugged. He called me a “Nice lady”. I said I was going to leave a minute or two after him. I didn’t feel like doing my hooker walk beside him. I polished my wine. One more hour out of my life: check.

I left and changed into jeans and Chuck’s in my car. Ah, myself again. I drove to Long Beach and proceeded to get crazy drunk with one of my best friend’s and her man. I also had my first encounter at the bar with one of my readers! I was writing while waiting for my girl and a woman walks up and says, “Are you on Instagram?” Instantly, I knew. I also recognized her from her support and comments. We ended up having so much fun.

I never heard from the guy again. I keep meaning to text him about his billionaire buddy, but probably won’t. I also deleted my photos and info from that site. I think the men on there are looking for girlfriends who want free meals and earrings. I want weekly money with someone who can let go and come easy. There’s some chemistry that even I can’t fake.

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