Sweet Deal - Cover

Sweet Deal

by CreepyUnclePete - by AuthorWench

Copyright© 2025 by CreepyUnclePete - by AuthorWench

Drama Sex Story: College girl renegotiates deal with her "Sugar Daddy."

Caution: This Drama Sex Story contains strong sexual content, including Ma/Fa   Mult   Coercion   Consensual   Romantic   Fiction   Rags To Riches   School   Sharing   Group Sex   Polygamy/Polyamory   Anal Sex   Oral Sex   Prostitution   Illustrated   .

I’m Carrie Connor, a twenty-year-old Chemistry major. I was only a month past eighteen when my parents passed away in a plane crash. Out of desperation, I put an add on a “Seeking Sugardaddy” site. I was lucky and glad I had some ‘chemistry’ with the much older gentleman I found. Reggie provided everything I needed and nearly everything I wanted. He paid all my expenses, let me use one of his cars, took me on a trip to Japan, gave me gifts on every holiday, and paid for my apartment a few blocks from campus. He paid my medical insurance and even setup a retirement account for me. Most evenings he invited me to dinner at a nice restaurant and activities at one of many places I liked, dance clubs, mini golf, amusement parks, museums, and others.

He was never rude and kept our relationship private. When he talked with anyone who knew me, he said he was a friend of my uncle. They actually became friends, and I was thankful he saved me any embarrassment. He was generous, kind, and somewhat attractive. I didn’t mind so much that he was 54 when we met, nearly triple my age. He was charming and witty, and we had a lot of great conversations.

At least once a week, we had a long date then went back to his mansion. Sometimes we swam in his pool nude then made love. Other nights, we drank champagne in the hot tub and had sex under the night sky. I also loved the times we got massages followed by lovemaking in his huge bed. We had oral or quickies two or three times a week as well.

However, the few negatives were big ones. Because of my schoolwork I was busy often, writing papers, doing research, or studying for exams. He didn’t seem to understand that I only had two nights a week available for dates, other than Saturdays when I could usually spend a whole day with him. He kept inviting me out nearly every night, and I felt bad when I had to turn him down.

I was happy that he liked to kiss, make out, and cuddle a lot. When we had sex, he usually let me choose the position. I was glad he had self-control and could last a long time. He was a thoughtful and generous lover, and I had nearly as many orgasms as he did.

He never caused me pain on purpose, but he kept encouraging me to try anal sex with him. He’d squeeze my buttocks a lot when we made out, put a finger in my rectum as he ate my pussy, and kept asking me to let him in my ass. After allowing him to play with my anus using sex toys and lube five or six times, I finally let him put his big dick in my butt on his birthday. My gift the day after was a pair of ruby and diamond earrings. The bit of price tag left on the box started with 7 and a comma. My reward had cost him over seven thousand dollars.

He made sure to get us very slippery and started slow. The first half dozen times hurt, but only briefly at the start. It felt very strange and I didn’t like it. He encouraged me to rub myself while he did it, and the nice feelings from my vulva partly distracted me from the discomfort. Thankfully, he only asked me for anal once a week. I mused that knowing him, he probably set a weekly meeting on his calendar for butt sex. I didn’t exactly hate it but would have been happy to stop. I kept letting him because I knew it made him feel great and he was mostly good to me.

The last negative was monogamy. He insisted that I only be with him. There were several guys in my classes I liked, and two in particular I had the hots for. I was a little ashamed about it, but there was a girl I had a crush on, too. I consoled myself that most relationships would be the same. Most guys would insist on being the only one, and I wanted Reggie to myself too.

The only exception to our monogamy started when his son Andrew visited. Andy was getting divorced and talked with his father a long time. Reggie told him he could stay in a guest room a few weeks until he got an apartment. The next night the three of us had some champagne in the hot tub to celebrate Andy’s new freedom. After several glasses of champagne, Reggie teased that I was just the thing to cheer Andy up. I thought Andy was good looking, but I barely knew him. After a lot of teasing and prodding, I kissed Andy a while and let him play with my boobs.

The next night I got even more intoxicated and gave him a blowjob. I still would have liked Andy if I were single, but there was no way I’d give oral to somebody I knew less than a week if I was sober. I wouldn’t have done it with his dad watching or followed him to his bed either.

When I had a clear head the next day, I was very upset. Reggie had given me to Andy as a gift, like a toy, an object. I was angry, shouting and venting my feelings. When I emptied my adrenaline supply, I cried. He held me a long time until I got angry again and stormed out. The next day he bought me flowers and a necklace to make it up to me, and after a long talk I forgave him.

The next time it happened, he bought me a gold bracelet with rubies and diamonds. The third time I blamed it on alcohol, but I was mostly sober. I gave in because Andy was attractive and nice too, and I needed Reggie’s help badly.

Before long, most of our Saturday dates included me having a quickie with Andy. Other than blowjobs by the pool, I never had sex with them where the other could see, but I became ‘theirs’ instead of ‘Reggie’s’. Andy never moved out, staying in a room at the far end of the hall from his father.

When I woke in Reggie’s bed one Sunday morning, I was alone. He left me a note: - “Carrie, we’ve had a lot of ups and downs over the past two years, but I’d like to think our arrangement is mostly good. I understand that you need time to study for your final exams, so Andrew and I will be out of town a few weeks. We’ll return two days after exams are over. We’ll talk about our relationships and future then. Focus on your studies for now, and good luck. With great kindness and many warm regards, Reggie” -

After everything we’d been through and all I’d done for him, he couldn’t say it! He couldn’t use the word! I was ready to tell either or both I loved them, because I mostly did.


I aced all my exams then took a day to relax. I went to a spa and had my hair and nails done, then got a massage. I had lunch at a nice bistro on the way back to my apartment. I realized I’d only been there half a dozen times in the past month. Reggie’s mansion was becoming ‘home’. Without Reggie I wouldn’t even have an apartment or a car. I’d need to share a dorm room and walk everywhere, assuming I could find a way to pay for everything else.

I thought about our upcoming conversation. I was partly happy but wanted some major changes. I made a list, so I wouldn’t forget anything. I didn’t want to do anal again. I thought that if Reggie loved me, I shouldn’t have to.

I liked Andy and thought he was sexy, but he wasn’t very romantic and didn’t last long in bed. We’d kiss a little, enjoy five or ten minutes of fucking, then do something else for a few hours until he thought it was quickie time again. He always got a climax, sometimes three a night, but other than the rare times he licked me I didn’t. I wanted a lot more romance and foreplay with him.

I didn’t want Reggie and Andy passing me back and forth like a toy anymore, either. I wanted respect! I’d be happy to sleep with either of them a few times a week if I got to choose who and when.

 
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