I Was The Gift

One of my sugar daddies, who has been and on and off sugar daddy for the last two years recently called me with an enticing offer. How will I feel being a 'gift' to one of his key clients for a weekend in the Bahamas?

As much as the arrangement between me and the sugar daddy is mutually beneficial, looks and hygiene are still important to me. I get to select my sugar daddies and here I did not know who the client was with whom I was being expected to spend a weekend.

After the obligatory background check to make sure the guy was good looking, not a killer or rapist, and has a global corporate job and visible in the community, I agreed to the plan. The client was given my pictures and my sugar daddy obviously must have briefed him to the 'skills' I bring. Because, two weeks before the trip, my clothing request and some clothes were delivered to me for the trip. Clearly, the client (let's call him Bob) knew what I like or don't like. The request read:

1. Pack my sundress for the flight. No bra or panties. Sandals. (btw I never wear a bra in real life)

2. Two pairs of skimpy thong bikinis for the pool and beach time delivered.

3. A small red tight dress, backless, barely past my ass cheeks for Friday night dinner and club, stripper thigh-high boots, bright yellow thong, delivered.

4. Three sets of lingerie that also included a crotchless panty, delivered.

5. Request to pack tank top and tiny shorts for day time wear

6. My favorite night club dress from my wardrobe with heels packed

7. Toys that I enjoy the most

Clearly I knew before leaving what kind of weekend Bob had in mind, and I liked it.

I flew down Friday and Ubered my way to the resort. Bob was already waiting for me in the lobby. Bob was in his early 50s, 5'10", 175-pound fit guy. Slightly balding but looking good for his age. Married obviously. He greeted me with a big hug and a kiss on my cheek. I giggled and whispered that he can kiss me if he wants. And he did! Big kiss, some tongue, but just nice. He smelled so good.

We got into the elevator and Bob grabbed my ass as we stood, feeling the firm round young ass. He was happy to realize that there was no panty under the sundress. I dropped my hands to my side and rubbed his crotch that was surely getting hard. Clearly he did not want to waste any time getting down and dirty, and that was fine by me as it had been a whole week since I had been fucked and was craving sex.

We reached his room that overlooked the pool and the beach. No sooner had I dropped my purse and bag, Bob grabbed me from behind, one hand on my perky boobs and the other under my dress touching my pussy. He was kissing my neck and massaging my tits and rubbing my clit. Mmmm...it felt so good as he touched me. I tried reaching behind me to feel his cock that was trying to push hard into my ass. He liked that I was reaching back for his married cock as he started talking dirty into my ears wanting me to pull his cock out.

Somehow behind my back, I managed to unbuckle him and unbutton his pants. He did the rest and soon had his cock free. Still holding me that way, he hiked my dress and entered my somewhat wet pussy in one thrust. He felt good in me. He started fucking me fast and furious and told me how much he missed young pussy, how his wife pussy is not fun, and how he has been dreaming all day to have me arrive so he could spend the next two days fucking me. I pushed my ass back to take his thrusting and soon he was cumming deep in me. He must have been horny and turned on as he barely lasted a minute in me. He flopped down on the sofa with his cock semi-hard and still dripping cum. I turned around, got on my knees between his leg and cleaned him up. He loved my tongue on his freshly cum cock, as he was all tingly. He enjoyed that a lot I could make out.

The next couple of hours we stayed in the room as he wanted to see me naked and play with me. I changed into one of the lingerie he brought me. While he lay beside me on the bed, I pulled out my favorite vibrator and put on a show for him. He sucked my nipples and touched me and kissed me as I played with myself, leafing myself to an orgasm. I whispered to him, I like being eaten after an orgasm too as my pussy and especially my clit is very sensitive. He jumped between my legs and did an average job eating me. But it was good enough to enjoy while I lay there moaning and eyes closed.

It was late in the afternoon and he wanted to fuck me before we went out at dinner. So I sucked him long enough to get him hard. He then made me jump on top of him to ride his cock. His hands on my tits as I ground on his cock. I love to put on a show and I rode him seductively, as my hair fell all over my face. I love to be loud in bed too and he liked that a lot. He would grab my ass and pull me down deeper on his cock. Dirty talks, lots of moaning, name-calling, and he soon he was ready to cum again. With my hands on his bare chest, he exploded a second time in me. After he was done spasming every drop in me, we both collapsed and rested.

The evening dress was what he had shipped to me. It was very sexy, slutty, and revealing all at the same time. I knew he needed a young arm candy for dinner and club. The stripper boots made me look like a stripper. Once I was ready, Bob asked me to sit on the sofa with my legs open so he could admire my sexy body, staring at the yellow bright thong and get hard. He walked over to me all dressed (he was in a jacket, shirt, and slacks) and asked me to give him a blow job in the stripper outfit. I pulled out his cock and with my red lipstick started to give him a BJ. My lipstick was all over his shaft and he loved it. I must have sucked him for 10 minutes but he was not close to cumming. Mostly because he had just come twice and could not. I was getting tired so I said why don't we go eat, drink and dance and by the time night comes, he will be ready.

He agreed and we left for dinner at the resort. His hands were all over me during our walk to dinner and at the dinner table. All guys with their girls at the resort were staring at me and jealous of Bob as they all knew I was a sugar baby. Their wives/girlfriends were clearly not happy though. I didn't care. Bob was a good conversationalist and he kept the wine flowing and his fingers busy.

I was ready to go to a club. But it was early. So we decided to go to the bar on the beach. It was dark and the bar was dimply lit, exactly what Bob wanted. We sat the bar that was crawling with single or married men without their partners. They all had the knowing smile on their faces watching us. Bob was feeling proud that he managed to get a hot girl for himself while they all were there hoping to hook up with someone and get lucky. We ordered drinks and sat at the bar drinking. Bob's hands were on my thighs and riding the hem of my short dress. You can see all my legs and every once in a while as I shifted in my barstool, people could clearly see the yellow thongs. I enjoyed flashing all the horny men and Bob did not seem to mind. A few guys were bold enough to stop by and chat with us and hint if they could join the fun. Bob was clear, this night was his alone. Personally, I would not have minded if he invited another guy, but I also understood he wanted this night to be all his.

We were surely getting a buzz and Bob was convinced he was ready for another orgasm. So we agreed to go back to the room and fuck before we went to the club. As we got up and started to leave, I whispered in Bob's ears and wondered if he has ever fucked a girl in a bathroom? He had not, and was very excited about the idea. We could have used the bathroom by the bar, but all eyes were on me and we knew if we did that, many phone cameras will be ready for recording our ordeal. So we pretended to leave and walked our way through the lobby towards the conference area. Late in the evening, the conference area is normally desolate.

We were right. We found a women's bathroom and pushed in. Once in the stall, I sat down while Bob stood in front of me. I pulled down his slack and had his cock out in my mouth sucking. Stroking his cock, playing with his balls, I sucked him till he has really hard. I stood up, turned around facing the wall and opened my legs. Bob pushed my thong to the side and entered my wet pussy. This time his thrusting had new intensity. I took every inch of his cock in me. There was no one in the bathroom and had someone come, we would have also heard. So I decided to be loud and told Bob how much I am enjoying him fucking me and I want him to fuck me harder and experience his first bathroom fuck fantasy. That was all he needed. Enjoying watching me in stripper boots bent over, with my dress hiked and panty to the side, Bob was soon cumming in me again. Clearly, he was not into long fucking. He came quickly and easily. Did leave me a bit frustrated that I did not cum, but this was about my sugar daddy and not me.

Once we put ourselves back together, we walked out, grabbed a drink at the lobby bar and went upstairs to relax. During that time we discussed the rules for the club and for subsequent nights. The dos and the dont's. What fantasies he wanted to be fulfilled etc. Bob wanted to also know if he invited another guy would I be open to it? I told him I would love that (simply cause Bob was not a long laster in bed and I needed more). He wanted to know if I could help him pick a girl and bring her to the room. I told him I would be happy to indulge him for that too if he could convince the girl. I also agreed to do my part and help if the girl was willing. Once the rules were known, we drank a bit more in the room until it was time to leave.

In the cab, Bob had his hands under my skimpy dress and touched my pussy sometimes through my panties, sometimes pushing it to the side. The cab driver was fully aware of the shenanigans in the back seat. Once at the club, we made our way to the bar, grabbed drinks, and made our way to a place where we could dance. The place was packed with tourists and locals. Bob was not a great dancer but he made it up with his zeal to grind against my ass. LOL. Everyone was having fun and there was just enough of the crowd that was single. One local guy, all of 6'4", maybe 220 pounds black chiseled guy started to dance next to me. We had already agreed to the plan. So when Bob walked to get another round of drinks for us, I started to dance with this guy, named Derek. Soon Derek was grinding in me. This tall guy had to squat low enough to get his cock at my ass level given the small petite girl I am. I noticed Bob watching us and he took his time to make his way back.

Once he came back, he pulled me to himself and kissed me. As he handed me the drink, he made me turn my back towards Derek and reached down and lifted my dress to show Derek my tight perky ass and thong. He winked at him. I wasn't sure if that was an invitation or not, but soon Derek and Bob had me between them as a sandwich grinding on me. I love it. White and black guy both salivating over my body. I wondered if Derek will be invited back to our room.

The drinks were flowing, Derek and Bob were getting bolder as the night progressed and many times either of them has had their hands on my pussy and ass. Derek was bold enough that once while dancing against me, while he was behind me, he pushed a finger into my ass for a few seconds. It did catch me by surprise as I thought all he wanted to do was grope. Not that I minded, but it was bold nevertheless.

I was so horny with the attention of these men. We had been drinking and dancing for two hours. Bob was surely quite drunk and I knew he would not be hard enough for sex. But it was his party and his rules. Soon Bob was ready to go back. But no Derek. Just him and I caught a cab and were back in the room. Once in the room, Bob grabbed some electrolytes to drink, hydrate, and sober up. But he was not that drunk to know what was going on.

He walked me to the balcony, still dressed in the naughty clothes, him with his hydration water, and pulled his cock out on the balcony and asked me to suck him in the open. It was quite dark so no one could really see or take a pic. But one could also clearly make out what was happening in the moonlight that basked the balcony. I squatted between his legs, but Bob asked me to stand up and just bend from my waist, with my ass towards the beach and then suck him. I was happy to oblige. I could feel the cool ocean breeze up my ass as I sucked Bob. He got hard easily even though I assumed he would not. His hands were in my hair soon and he started to face fuck me. He absolutely loved the control he had. Part of our role as a sugar baby is to make our daddies feel in control.

I wondered if he would cum that way. He knew I swallowed based on our chat early today. He picked his tempo and I was sure that his intentions were to cum in my mouth. So I started to stroke him and play with his balls. And that helped. Soon Bob was exploding globs of cum in my mouth and moaning loudly and calling me names. He loved that he finally got to cum in a girl's mouth who swallowed as his wife has always refused to let him cum, the few times she gave him head.

After pulling his pants up we walked back to the room, got naked and fell in bed drunk and asleep. The first evening was wonderful and we had a full day tomorrow to look forward to and discover new levels of debauchery for him.