[FM] My last night as a sugar baby, ever

This is exhilarating! I want to keep this up a little longer. Like I said on my last post, I worked as an escort and a sugar baby all through my late teens and twenties. A few years ago I got out of the biz, if you want to call it that, and now I make a living mostly from my investments. This is the story of my last night as a sugar baby.

Some people asked me to describe myself last time, so I will. I’m thirty six years old now and for a long time I struggled with not being so young anymore. But even though I weigh more than I did when I was a twentysomething, I still work hard to keep in shape. I’m curvier now than I was then, but thanks to the gym I make it work for me. My hair is long and chestnut brown, the same color as my eyes. My eyelashes are my best feature while I have clothes on. When I was a teenager I struggled to stay as skinny and small as the other girls, so I appreciated when bigger butts and tits came into vogue. After so many years dressing to impress I usually wear athleisure clothes unless I’m going out with friends or on dates.

Now, the man in this story is named Robert, or Rob, as he demanded I refer to him. I think it made him feel younger. He wasn’t my longest lasting sugar daddy, in the bedroom or in my social life, but he was my final one. We met when I was twenty nine, and I got out of that lifestyle entirely when I was thirty three. At twenty nine I already knew I was aging out. Plenty of men liked my looks, but the people that pay love fresh meat the best. By thirty I had stopped escorting entirely and I only had one sugar daddy for the next three years, Robert. He was in his mid to late sixties. I’m not sure exactly how old because I didn’t ask and he would have been angry if I had. The benefit of being with an older man happy to be with an “older” (euch) woman was that he knew what he wanted and he was very generous. He wasn’t one of those men who wanted companionship first, he just got off on having a supple woman do whatever the fuck he wanted in bed and in life. I transformed my wardrobe thanks to Robert’s generosity and made some stable investments to boot. Most of my money now still comes from the investing help I got after 2008 from a banker, but Robert made it much easier to get out of the game.

I told him that I was done in the summer of 2019. He pushed me to delay it in return for a grand Greek vacation and some special shopping sprees. The vacation wasn’t very restful for me, you might guess. He got his fill of me every day until his dick was too sore to go again. But the end of summer came and so came the day I set for our last encounter: August 31st. Early on Robert had tried to push it back even further, but I was done. I had just turned thirty-three a few weeks earlier and I wanted the rest of the year for myself. That was wise, as it turned out, given what happened in 2020!

Showmanship is first of all for any good whore so I knew I wanted to leave him with a good impression for our final date. My priciest lingerie; my most elegant dress. I took him to his favorite restaurant. I hesitate to give more detail than that in case someone guesses where I am! For once I paid the bill, although in a roundabout way, it was his money. Then we were going back to the apartment he rented just for his personal play. Like many men in this lifestyle, he had a wife and kids, though we had done it at his house a few times when they were on vacation. It was a nice apartment, I was jealous of it. Small, of course. He wasn’t living in it full time. Out of the way so he wasn’t paying exorbitant rent prices. But cozy. I like a place where the light is low at nighttime.

There was a stripper pole in the living room. It ruined the vibe, I thought, but it made it obvious what the place was for. And so I performed for him. For a short time I had been a stripper right out of high school, and plenty of men liked to watch things like that, so I had kept my skills sharp. Not anymore, though. But in my extravagant underwear I gave him the show of a lifetime. I’d like to thing I put Elizabeth Berkley to shame, but I don’t think I was that emphatic.

“Show me that ass,” he said. I leaned against the pole with my hands wrapped around it, pointing my rear in his direction. My heels were still on. I wouldn’t be much of a pole dancer if I had taken them off, would I? So on four-inch heels I waited for him to discover his surprise. It was new, the plug. He had never seen it before. Even for my trained butt it had been a challenge but that was the sort of thing Robert liked.

“Amazing,” he said.

“Thank you Daddy.”

He flicked it and I groaned. It actually fucking hurt, but I tried to make it sound sexy. Since I was still facing the wall I heard rather than saw his belt hit the floor, along with his pants. No wasting time, I suppose. It was his last chance at this pussy. I tightened my grip on the pole as he fucked his way into me. He kept his thumb on the plug while he rode my cunt. I tried to call him Daddy every time he bottomed out in me. He liked that. He wanted to use my body, but it was important that he knew I was with him in mind, too. He came inside me like that, for the first round, and then sat right back in his chair like we were sitting down for a chat. His living room didn’t have a proper place for me, so I went off to the bathroom to clean up. His Viagra was there, so I brought it with me when I came back, pushing it into his mouth on my fingertip.

“Thank you baby,” he said, grabbing me and pulling me into his lap to kiss me. Some men don’t like to kiss at all. Others are obsessed with it, especially since some escorts don’t allow it. Robert was somewhere in the middle but he was making the most of his time. Between kisses he told me how much he was going to miss my tits, me, and my pussy, in that order. He was getting hard again and I started stroking him.

“Do you want me to do that thing…?” I suggested. We had only done it a few times. Back then it was still almost cutting edge, the sort of thing you only see in porn. He didn’t answer me, just shimmied down the chair as I stood up, so his ass was jutting out off the side.

I always hate when I see girls that eat ass with only their mouth and leave the man to jerk himself off. It’s lazy and not as fun, in my opinion. You might guess that I’m not one of those. With one hand I lifted his balls from his taint and pushed my face as deep in his ass as I could. I started to stroke him off as I lapped his ass.

“You amaze me every time,” he said.

“Thank you Daddy.” With my tongue on his ass I could only hope he understood what I meant.

Like I said, we had only done it like this a few times before. It was still a novelty for him. He didn’t last long. Robert wasn’t too prideful to cum on his own stomach, but he took pride in holding my hair and dragging my face across it to make sure I licked it all up.

He wasn’t one for companionship, but he liked to make the most of his opportunities. That last night he fucked me twice more in our bed, with the help of those Viagra in his bathroom. I woke up alone the next morning. There was an envelope waiting for me with a going away present and the keys. His note said I could use the apartment how I liked for the next week.

I’ve had good men in my life and bad ones, and Robert is one I look back on fondly.

Source: reddit.com/r/gonewildstories/comments/xa1hh2/fm_my_last_night_as_a_sugar_baby_ever

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