I met Tom through a website for the whole sugar daddy thing. His posting mentioned his income range, mid-six-figures, the pay he offered along with the parameters. I jumped at the chance because his posting specified no additional expectations. Some guys write that there may be “additional duties associated with the role.” I didn’t sign up to be a high-priced escort.
But there I was a year later, sitting on a sailboat on the Mediterranean, having sex with this rich guy.
Tom had rented it for our summer tour of Europe and the rental included a captain and personal chef. He said his company agreed to it because “when you add up the cost of train rides and hotel rooms, the type he is used to staying in, this was around the same price. Close enough”.
I couldn’t complain. I was sunbathing on a deckchair on the starboard side and enjoying the sound of the boat cutting through the calm waves. The sun warmed my skin but the breeze kept me cool.
Tom poured me a glass of white wine and brought it over. He wore all white when we were on the boat. Usually shorts, loose, cottony, white button-up short sleeve shirt, left mostly unbuttoned, and a straw fedora.
“What are you reading,” he asked.
“Oh just a silly romance book. My phone doesn’t work out here. I found this in a bookstore the day we left France.”
“What’s it about?”
“A woman who falls for her roommate’s brother.”
“Ah, a nice-girl romance. Not a bodice-ripper, or so I’ve heard them called.”
“The roommate’s brother is an internet-famous amateur porn star.”
“Ah, the plot thickens.”
“According to the narrator’s encounter walking in on him in the shower, it’s not the only thing that thickens. He’s famous for his huge cock and his oral skills on women.”
“Touché,” he said. “Any good?”
“Like I said, silly. But I like silly sometimes.”
“Yes. Life has a way of being too serious sometimes. Scary even. And as you age, it only gets worse.”
“Well, that’s a downer. Can I go back to my happy book now?”
“No.”
“Why not?”
“Are you talking back to me?”
“No, I’m simply asking why I can’t just relax and not get all morbid with you.”
“To the bedroom, now,” he muttered under his breath. The captain wouldn’t be able to hear but Tom makes sure we are not eavesdropped upon.
“Is that an order?”
“Yes. Remember why you’re here in the first place. Only at my request.”
“Fine.”
“Just because of that attitude, take off your bikini top while you walk across deck to our room.”
“Seriously? Jean will see me.”
“That’s part of your punishment. It’ll teach you to listen to what I tell you.”
“I’m sorry. I will.”
“I know you will, so let’s go. Take it off.”
I did as he said and while I’m sure Jean had seen countless topless women on the beaches here, and even on his boat, I was never one of them. Mark was the only guy who had ever seen me naked, until Tom.
Mark… Before I left on this trip, we met for coffee and he told me he slept on it and wasn’t comfortable with my new arrangement with Tom. He didn’t want to introduce me to his parents as the one with the job where she “whores herself out”. I told him I didn’t want to be with anyone who was such a jerk and that was that. It was fine. I flew to Europe and he’s back in Des Moines with his family for the summer.
I lifted the top over my head, my 1xbet yeni giriş breasts bouncing as they were freed from restraint. Tom held out his hand to take them from me.
“Bottoms too.”
“You’ve got to be kidding?”
“Tone. Watch it.”
I looked around and I caught Jean watching us. I didn’t want to make this any worse so I stood up and slid them past my hips and dropped them to my feet.
Three nights ago, Tom caught me checking out a guy before we left port and he led me to the room where he pulled my skirt up and my panties down and spanked me for a good five minutes. I won’t say I didn’t like it because I kind of did but my cheeks were sore all night. I don’t think I’m ready for another one of those punishments.
“Ok, walk.”
I looked at the steps down to our little suite and figured it was twenty paces. I steeled myself to put one foot in front of the other and walk there with all the dignity I had. This dignity meant focusing my gaze on the goal and ignoring my periphery vision but I swear I saw Jean give a thumbs up to Tom as I ducked down the stairs. His conquest. His kept woman.
At the bottom of the stairs, he used the bikini top to tie my wrists behind my back. He pushed me onto the bed. I fell on pillows, my knees supporting my butt which stuck in the air. Tom unzipped his shorts and pulled out his cock. He wasn’t fully hard yet and I could feel him bend as he pushed into me. He grew harder within a few seconds.
So a newer fun fact about me, I realized very recently that I love to be used for a man’s pleasure. When he started to tie me up and fuck my brains out, I really get off on that. Who knew I was such a deviant? Some may wonder why I was ok with all the unprotected sex, well, I am on the pill and I also asked him to start pulling out, just to be extra safe. He’s reasonable when it comes to that stuff.
I burrowed my head into the pillows to muffle my screams as he held my bound wrists with one hand and braced himself against the ceiling with the other. The boat was swaying from the water but it felt like all of the force of those waves was coming from his cock.
I felt every inch of him filling me and leaving me, over and over. It made my pussy beg for more, making me wetter by the second, just in time for him to thrust again. Harder and harder.
He reached down and grabbed my shoulders, pulling me up so my back touched his chest. He hooked one arm over my breasts, the soft flesh of them spilling from under his arm. With the other he reached down to touch my clit as he whispered something in my ear.
“- a girl who needs to be fucked.”
“Uh-huh,” I said, mostly to agree with whatever was in his head right then.
“I bet you won’t want any skinny dick guys after I’m done with you.”
“I don’t want any now.”
“You just want a big cock to stretch you out?”
“Yes, the bigger the better.”
I started rocking my hips against his curling myself so his cock hit the right spot. It also gave me a little control about my own orgasm. Just a little. It wasn’t a guarantee I could come this way.
His thrusts came in slower but stronger waves as he kept his hand between my closed thighs. I started to shake from the pressure inside and the stimulation outside. I tried to push him back with my hips. I couldn’t take anymore. It felt so good I wanted to beg for it to stop.
“Come for 1xbet giriş me,” he said. “Come for me now. Come on my cock.”
I listened to his deep voice and allowed my body to give in. I thought about his body behind mine and how he held me tight.
In this relationship, he took away my choices. He gave me whatever I wanted. And all I had to do in return, was to do whatever he wanted.
“I’m going to come for you,” I said. “Don’t come yet. Wait. A few… more…seconds… yes! Yes!”
“Fuck,” he yelled as he slipped out of my pussy. His cock was trapped between my legs as his come shot out all over the bed.
He untied me and I turned around to gauge his mood. He smiled and went to the bathroom. The shower came on.
“Tomorrow, we should be near Italy,” he said.
“Ok.”
“When we get there, I need you to play a role for me.”
“Isn’t that what I’m here for?”
The water stopped. He came out in a towel wrapped around his waist.
“It’s complicated. It’s not the normal dinner party where you hang on my arm and then we go to the balcony and I hike up your dress and we fuck. This is more intricate.”
“Like a puzzle?”
“More like a labyrinth. We don’t know where it will end up or what we will see as we try to get to where we intend to go.”
“Now, I’m confused.”
“If I had to guess, I think you’ll get all dolled up and have to flirt with some old men. Try to get them to see that I’m a normal guy with a hot wife who they may have a shot with, but then bring their attention back to how they should do business with me.”
“I don’t want to fuck old guys.”
“I’m not old to you, thanks for that.”
“You’re not. You’re vigorous for a not-quite old guy.”
“Thanks rescinded. You won’t have to fuck anyone. You just need to play that part. I’ll work the marionette strings to get the desired results.”
“If you think I can handle it.”
“I know you can.”
The next morning, we landed and docked and I had cell service again. I checked my bank account and sure enough my account was another eighteen grand higher.
Tom took me to the fashion district and swiped his card for a half dozen outfits. I couldn’t believe he was paying all of this money for clothing that cost more than my rent for a year. No one back home would have anything like the white dress I bought in Italy or the sexy lingerie from France. That afternoon, we went to a bistro on the waterfront.
All of these things were a dream to me. I was just a simple girl from a quiet suburb near DC. I was going to marry a nice guy who was adequate in bed and brought home a modest salary and grow old, never realizing the bigger dreams that I had.
Now, I was living them.
“Put on this red dress, these red bra and panties, and these heels,” he said as he handed them to me.
“This stuff is really sexy.”
“I know. That’s the point.”
I put it all on while he watched. While I undressed, he jerked off into the panties I had been wearing. I just let that happen. It didn’t phase me.
When everything was on and I had braided and pinned my hair in the mirror, I stood before him and lifted my arms at my sides.
“Good enough?”
He squinted at me and seemed to be thinking quite hard. Too hard considering the question was basically, “do I look good?”
He lifted my dress and pulled my panties off. They wrapped around one 1xbet güvenilirmi of my heels and that almost made me tip over.
“Perfect,” he said.
“I don’t need panties tonight?”
“You need to feel like you don’t need panties tonight. Get it?”
“Actually, I kinda do.”
He threw on a fresh shirt and knitted a tie in what I consider record time for anyone… ever, and we were off.
“I will warn you now. The thing tonight is different. It’s like a sex club for rich people. They share each other’s spouses. So slip on this ring.”
He slid a freaking ridiculously expensive looking ring on my finger and made a joke about our elopement before looking at me. It felt like he was evaluating my thoughts. Could he read my mind?
“So we are going to split up?”
“No, no. We don’t have to. But that kind of thing happens here. We have to play the part. These people are weird. They have everything and yet they have these parties where they have to try to seduce each other.”
“So men going after wives?”
“Some of the wives drag their husbands here. I don’t know if rich guys satisfy their wives. I can’t see too many of them going down on a woman. Probably creeps them out.”
“Have you been here before?”
“I’ve been to all these places before. They send us once every few years. A single guy isn’t the most trustworthy person I guess. They prefer someone who will screw their wife or someone’s wife who they can screw. That’s why I knew I needed a partner for my next trip.”
I was still confused by what he wanted from me but I figured I was safe in his hands. And I figured right. He kept an eye on me. He was very protective of me, using that to sway some of the men to discuss some shady things in a quiet hallway. They kept looking at me while I held a glass of champagne and watched another couple having sex through a cracked door. The woman was on top and boy, was she riding that poor fellow. Or maybe he liked it. But I heard later that she broke his dick from her enthusiastic cowgirling. Who knew that was possible?
Anyway, not wearing underwear did make me feel more sexual. I kept thinking about who I would consider sleeping with. I guess Tom was right.
“See that guy over there,” Tom asked when he walked over to me.
“Yeah, the guy with the handlebar mustache and the monocle?”
“That guy isn’t here. That’s from a movie.”
“Oh ok, the young Latin guy?”
“Yes. His father just died and left him an empire of service stations in Spain.”
“Gas stations?”
“A lot of them. We want to handle his financial transactions. Card readers, statements, all that.”
“Cool.”
“He wants too. But he is playing hardball. He said the only catch is that he wants you meet him upstairs.”
“Oh…”
“This is a huge deal. I’ll double the week’s pay. Use a condom if you have to.”
“I mean, he’s hot. That’s not a problem.”
“Ok, then let’s go. He invited us to a room upstairs.”
I followed behind; holding onto Tom’s hand as he led me through a crowd near the stairs. Eyes were on me as we went up. I grabbed another glass of champagne from a waiter and handed him the empty one.
We walked into a room with one king bed and four other women.
“Hello everyone, for those who don’t know me, my name is Marco. Tonight, I’m trying to make a difficult decision. Now that you’re all here, I’ll ask the women to bid their husbands good night.”
“You’ll be alright,” Tom said. “Remember our deal. Here’s a condom.”
The door closed.
“I will give business to the family of the woman who pleases me most.”
“Great…,” I thought.