The Gift That Continued to Give

These are my true stories told from a sugar baby's perspective.

This story picks up on the second day of my time with Bob. if you want to know what happened on day one, read the story, 'I was the Gift' published on October 29th, 2019.

The morning started as I suspected, Bob, trying to push into me with some morning wood. With my back to him, he grabbed my legs, slid down and tried pushing in. He got his dick in my pussy and started to thrust while grabbing my boobs. He came quick and then rolled off and went to the bathroom to clean up. I asked him to order breakfast for us and soon I was having sumptuous breakfast in bed. Still naked and with cum in my pussy, I enjoyed the hot meal. I asked Bob if he wouldn't mind eating me as part of his breakfast. He was excited, a bit worried about his cum in me, but soon seeing my naked body spread on the bed, he was between my legs.

I closed my eyes and enjoyed him eat me. I softly promoted him what I liked so he could get me to an orgasm. Which he did. I must have pushed him so hard between my legs, that when he came up for air, he was flustered. But what an orgasm that was. After relaxing for an hour, I showered up and got into a sexy bikini. It was a thong bottom and a small top that showed a lot of my boobs. These were the ones Bob had shipped to me. I admired my sexy body in the mirror knowing I will get all the looks at the pool.

Once settled at the pool, Bob ordered beers for himself and I ordered Mimosas. I made sure I asked Bob to put sunscreen on me in front of everyone. Many married men stuck with their wives would continue to glance my way wishing it was their hands on me. Bob obviously was enjoying it. I lay on my back and stomach often to let the world see my young body in that skimpy bikini. Every dip in the pool was followed by a slow exit from the pool and slow walk to my lounger so more people can see me.

The pool waiter, who must be 25 years old was also paying special attention to me. He (Joe) was happy to keep bringing me snacks, water, and drinks so he could come and talk to me and stare at me. Bob also knew what was going on. At some stage, he leaned me and told me that Joe is lusting on me and if I was open to the idea, we should invite him to the room. That was music to my ears. Joe was a handsome young man. Fit, chiseled, and build strong. I wanted a strong man to fuck me hard.

Bob spoke to Joe and it was agreed that during his break (30 minutes), Joe will come over to the room. We both made our way back to the room about an hour earlier. Bob asked I remove my top and just stay in my thong bottom. We made out on the bed, he fingered me while we made out, and made me cum. We continued drinking and soon there was a knock on the door. Bob asked me to go open the door. I walked my sexy ass to the door, and once I realized it was Joe on the other side, I opened the door as I stood topless for him. His jaw hit the ground when he saw my perky 34c boobs staring at me.

I grabbed his hand, pulled him inside and wrapped myself on him kissing him passionately. His hand immediately grabbed my ass, lifted me off the ground, his cock against my crotch as we kissed. Bob shouted from the bed asking us love birds to get into the bedroom. Joe carried me into the bedroom and dropped me on the bed. I had no idea how the guys wanted to do this, but I was so ready to be fucked. Joe looked at Bob and got the approval nod. Next thing I know my legs are open, my bikini bottom is stripped of me and Joe is eating my pussy like an expert. My hands in his hair, I push him deeper in my pussy enjoying his tongue.

Bob rolled up on the bed, pulled out his semi-hard cock and pushed it in my mouth. Here I lay being eaten by a hot dude and an older guy's cock in my mouth. I went to town sucking Bob and Joe did his job with his tongue and finger to make me cum hard. I was moaning so loud. I needed a break too, as my pussy was so sensitive to this hot orgasm. But I barely got a chance to relax when Bob jumped over, asked Joe to move aside, opened my legs and shoved his hard cock in me and started to fuck me. Joe moved over to the top of the bed, stripped naked and his 8-inch cock was in my mouth now. Bob was fucking me furiously and I knew he will cum soon, which he did. But this time he sprayed his cum all over my tits. And then used his hands to rub it in my body.

Joe who was already hard in my mouth knew it was his turn. He grabbed me like a rag doll, turned me around, put on a condom and pushed his cock while having me doggy style. He grabbed me by my waist as he fucked me hard. He smacked my ass hard as he called me names fucking me. His thick long cock filled me so well and I wanted to cum that way. I told him between my moans that I want to cum first. Hearing that, he pulled out, jumped on the bed and lay down and asked me to ride him reverse cowgirl till I came. We changed position and I had his 8-inch cock in my freshly fucked pussy. Bob who was enjoying the view, walked and stood on the bed and asked me to suck his cock while I rode Joe.

I could taste Bob's cum and my cum on his cock. Joe, on the other hand, had me by my waist and was making me ride his cock. All this was so intense, that soon. I was cumming on Joe's cock. Wow, that felt incredible. Bob moved away as he let Joe turn me over again and this time made me stand on the bed edge, bent me over, came behind me and entered my pussy. He started to fuck me hard with all the intentions to cum. I hate condoms but given that Joe was a stranger, it was the safe bet. But I looked back at him with seductive eyes and asked if he wants to fuck my ass.

I could see Bob and Joe's eye both pop out with excitement. Joe pulled out and wanted to enter my ass immediately. I stopped him, walked over to my suitcase and pulled out some KY Jelly. I walked to Joe, pulled the condom off his cock, lubed his cock with jelly, turned over and asked him to fuck me bareback in my ass. Joe could not believe it and soon his big cock had made his way into my tight ass. He grabbed me by my waist as he started to drill me. Hard and fast till he came deep in my ass. Once he had dumped every drop, he pulled out and pushed me face down on the bed. I lay there exhasuted and used.

Joe pulled up his pants, cleaned up and left. Bob looked at my freshly fucked body and said, tonight he wants to fuck my ass. But for now, he wants me to clean up really well and join him back at the pool in my skimpy bikini. I did and as we both enjoyed the sun. Joe who was back at his work continued to admire me knowing just a few hours back he was fucking me. We were leaving the next day and I am sure Joe would have loved to join us after work tonight, but it was Bob's call and what he wanted.

All I could do was enjoy the pool and wait for what the evening held for me. I worked on my tan and these skimpy thongs and top were sure to leave some very sexy tan lines.

Evening, Bob asked me to wear my tiny shorts and top and we ate at the hotel restaurant. He wanted to admire my petite body in those tiny shorts and run his hands all over my sexy things as we ate. I was sure Bob will ask to go back to the bathrooms by the conference room to fuck, but he did not. He was focused on the drinks and dinner. That was fine with me as the afternoon fuck session had me sore.

We came back to the room and had a couple of hours before we were to go back to the lounge upstairs at the hotel This was a seductive bar and lounge, people dressed in their best clothes, local girls sitting at the bar looking for their client, single and married men scouting for fun. Bob wanted me to dress slutty and I was happy to oblige. Night came and I pulled out my sexy black dress. Backless all the way to the top of my hip, deep cleavage in front, almost to my navel, sticky tape to keep them in place to cover my boobs, not long enough by any means and just past the round firm butt. Bob asked I wear no panty. I have sexy fuck me heels. Makeup and jewelry later, I was ready.

Bob admired his young sugar baby. His married cock was hard looking at me. I asked if he wanted a BJ before we went to the lounge? What guys ever say no to an offer like that? Bob sat at the edge of the bed, my on my knees between his leg, his cock in my mouth, his hands pushing the tape to the side so he can grope my tits. I sucked him just the way he loves to. Soon his cock was spurting his cot cum in my mouth and I was happy to swallow and suck him clean. Happy and relaxed, he pulled his pants up, I re-did my makeup and we made our way to the lounge.

In the elevator, Bob put his hands under my dress to grab my naked ass. His fingers flirted with my pussy and ass and he leaned and whispered, 'I want to fuck your ass tonight!' I was happy to let him have that and I also learned during the evening that Bob has never had anal sex. I was happy to be his anal virginity person. At the lounge, the music was sexy, the atmosphere sophisticated, and people dressed to impress. Many eyes checked my scantily clad body. Bob had his arms around my waist, making sure everyone knew I was his property for the night.

We were led to our booth (reserved by Bob for the evening) to settle in. Once the drinks were ordered, Bob sat back and asked me to snuggle against him, my back on his chest. Bob always smelled great and it was nice to kick back and settle in, enjoy drinks and music. Bob played with my hair, ran his hands on my arms, often letting the wander to my breast and open cleavage. He would tell me sexy things about how hot I am, how much he is enjoying fucking me, how he loves my tight pussy, and so on and so forth. I was glad he was happy as my sugar daddy will be pleased his client was well-taken care of.

As the minutes ticked by, Bob wanted to know if we should make it a party in the room or just have me for himself. I reminded him, it was his rules and desire. He thought about it and then whispered in my ears a bold plan. Bob wanted me to grab a stranger at the bar, convince him to go with me to the bathroom, and suck him. No sex. Just BJ. I smiled and reminded him that it is not tough to get a guy to drop his pants for a sexy girl. That was hardly a challenge. We both laughed and agreed the last night should be about Bob's and his needs.

Lots of alcohol later, with a great buzz on, we stumbled our way back to the room. Bob was not shy of grabbing my ass as we walked and I am sure many times his hands which were under the short dress was showing my naked ass to many in the lobby. I have always been a tease and have never mind flashing or letting men get sneak naughty peaks. It gets me wet when guys notice and fantasize about me.

Once in the room, I decided to give Bob the show of his lifetime. Pushed him on the bed, legs hanging over the edge, stripped him naked, and put on some music. I started by giving him a great stripper dance, still dressed in my tiny dress, rubbing my ass against his cock, putting it between my boobs, touching myself as I gyrated. Pushing my hips in his face for him to grab and smack. I danced and rubbed his cock with my body in ways he never has been treated. It was time to strip into my fuck me heels. Bob loved unzipping me as I let the dress drop to the floor. Bob was begging me to sit on his cock. That is too easy. So I continued with the tease by walking around making drinks for us naked in my heels. Drinks in our hand, I went down on my knees between his leg and with cold ice in my mouth, cold tongue started to suck him. The cold and hot made him go wild. He wanted to cum in my mouth badly. But I also knew he was good for one orgasm only and tonight I wanted to have some fun too.

I stood up and pushed him back on the bed. With my drinks still in hand, I straddled his face and asked him to eat me. Bob was an eager eater and went to town eating me. His skills were not the best but I was so horny that riding his face was guaranteed orgasm. One hand in his hair, I rubbed my pussy and Bob ate me till I came. Mmmm. I felt so much better after that orgasm. It was time to let Bob do what he wanted.

Bob asked if I was OK to fuck on the balcony. I got off him, walked to the balcony naked, still in my heels and stood with my ass towards him, bent at my waist as I rested against the railing. Bob was right behind and he pushed his cock in my pussy that was still tingly and sensitive from the great orgasm. His hands-on my tits as he fucked me. He was fucking me hard in the open and even in the dimly lit night, anyone could see the silhouette of two people fucking. I could sense he wanted to cum badly. I reminded him he wanted some anal action. I also wanted his virginity. Bob who was reasonably drunk by now pulled out and tried pushing his cock in my ass. I asked him to grab the KY Jelly. he staggered to the room, came out with the bottle, lathered his cock with it and started to find his way into my ass.

A few adjustments later, his cock was deep in my ass. Bob picked his speed and his hands on my ass, grunting, moaning, and calling me names, his cock explored me deep. A minute of fucking and Bob started to explode his hot jizz deep in my ass. I squeezed my ass cheeks to get every drop in me. Soon Bob was limp and slipped out of my ass. He fell down in the chair on the balcony. I turned around, smiled and asked how his first anal experience was. He loved it and wanted to have some more in the morning before we both flew out.

I nodded, grabbed his hand and we both ended in bed naked. Morning came and Bob woke up with morning wood wanting to fuck my ass. I lay there with my back to him as he lubed and fucked my ass one more time. After emptying his balls in me he got up to shower. I wondered if he wanted one more fuck in the shower but when I walked in, he was still limp and not enough in him to get hard. So be it. I had a great time with him. He was always attentive to me, kind, took care of me and I am sure my sugar daddy will be very pleased to learn his client had the time of his life.

Before leaving we made out one more time, clothes on though. Satiated Bob thanked me and we left for the airport and on our way to our homes.