Miami Escort Visiting a Wealthy Cuckold

I am Caroline, 21 year old, brunette, tallish, originally from Wisconsin. I came to Miami to attend a community college. Actually, I just needed a reason to be here and this was good enough for my parents. They are middle class and saved all their life to send me here and they do more than enough. But being here makes you dream, you just want to figure out how to get in the glamorous lifestyle. My weekend is devoted to a rich guy whom I know for a while. Our dates are very peculiar but somehow he makes me feel very comfortable

Day One

8 a.m. I’m no “girl gone wild”. I wake up early, I clean my room, I study, and I get ready for work. At 8am, my alarm always goes off, and I always slide out of bed sheets.

9 a.m. The shower is really hot, and I love it. I wash up and shave my pits, my legs, my privates.

11:30 a.m. I clock in at work, and say hello to my boss. Mon-Thurs, my life is that of a totally normal 21-year-old student. I’m a business major so I study a lot, and work little. On the weekends, this all changes.

4:30 p.m. Shift is over, so I head back home, and throw on a bikini and rush to the beach. My roommate joins me and we suntan and discuss our current crushes and fashion trends. Like I said, I am so totally… normal.

6 p.m. It’s Friday, so I start packing up my weekend bag. Sunday night I’ll return home, so I pack a toothbrush, my razor, and plenty of sexy clothes.

8:30 p.m. I arrive at my client’s house, a little over an hour away. I’ll call him V from now on. We met online when I was a cam girl, and ever since, he’s paid well if I do what he wants.

8:45 p.m. He kisses my cheek and I go inside, listening to him talk about his week, his job, his excitement for the weekend plans he has set up for us. He encourages me to update my online ad and I comply. Few minutes later, first calls start coming in. They sound disappointed that we can meet tomorrow and not now but it is what it is.

10 p.m. In his pool, we go for a quick swim, and I know he admires my nude body. Yet, V almost never touches me himself. Apart from his relatively weird ways of having fun with a girl, he is very confident and successful. A few years ago he sold his own start up and invested most in the currently booming stocks. He is really smart with his money. I guess at some point he tried everything and now only gets excited by unorthodox stuff. Again, not complaining at the slightest.

Day Two

10 a.m. We both slept in.

10:30 a.m. I get up and order breakfast with a food delivery app from iHop and wait outside for the driver.

12 p.m. V wakes up and we eat together. I ask about what we’re doing this weekend and he shares some of the dirty messages he’s exchanged with other men during the week about me.

3 p.m. I shower and get dressed in appropriate clothing. I’ll be seeing 4 clients today, and V plans to watch me get fucked each time. He knows that not all clients would be OK with him watching so he wants to keep it as natural and genuine for them as possible. He will be staying in his room and watching us on the security camera. It’s gonna be an exhausting day, and I feel anything but normal when I stay at his house.

5 p.m. The first client arrives. I’m in a strappy red bikini, dripping wet from the pool, and he fingers me before fucking me on the enclosed porch. It’s pretty brief, and over before I could of ever hoped for.

6 p.m. The next client arrives, and I suck him off in the living room. A security camera watches us and I know V will save the video. Privacy laws, what are these?

6:30 p.m. I ride the man on the couch until he grabs my hips and eases me to the floor, and goes hard for about 3 minutes before he cums hard. We say goodbye.

6:45 p.m. Rinsing off in the pool, naked, V and I decide to take a break from clients and we dress for dinner. Again, we order in.

9 p.m. Time to resume.

9:05 p.m. The next client arrives and this time, we fuck slow and sensual in the bedroom. There is no security camera here so V locks himself in the adjacent room and hopes to hear something. I’m growing tired. Sometimes… I hate the weekends.

9:50 p.m. This dude took seriously almost the whole hour. Jeez. My poor vagina. He finally leaves, and I let V look at my pussy closely. It’s red, and sore, and he says how badly he wants to eat it… but again, he doesn’t. And I wish he would. One thing V is good at is his tongue. Its ridiculously frustrating to get fucked so many times and not cum a single time.

11 p.m. Almost done. Waiting for the last client to show up and, he is running late, of course. We wait outside, sipping wine, and I end up a little tipsy before he arrives.

11:15 p.m. An older gentleman. He smiles, introduces himself, and comes in. Fucking older guys is almost never plain vanilla. They either cum very fast or don’t come at all. This one was no different. Horny beyond belief, he didn’t even ask for a blowjob. I put him a condom and he told me he wants doggy. A few short moments later, he was done.

12:15 a.m. Time to go home. V got a cab to pick me up and take me home. I am not sure if he even cum during the day. Knowing that he is a person of the extremes, he either cum many many times or not once.

12:45 a.m. Ready to go to bed when a guy I used to fuck as a fwb messaged me. “Wanna stop by for a quickie”’he said. I switched my phone off and fell asleep almost immediately.

3/51 rating
  1. acc4por_n October 26, 2019

    Amazing story but no pictures

  2. KILLERRabsKEN December 1, 2019

    The abscense of detail about what the visitors paid to the “not a pimp…?” Rich guy who it sounds like is definitely a pimp. Booming stocks huh any specific sectors or just the booming ones? This startup that was purchased is sketch too. How much were you paid? Plus he picked you up of a cam site…smh.. you were ready to be a prostitute but wanted to rationalize it as a sugar thing..

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