Cuckold Fantasy

These are my tell-all stories of my real life as a Sugar Baby. No personal details about my clients will ever be shared through these stories.

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I am surprised how many men have the fantasy about being a 'Cuckold'. One of my Sugar Daddies (SD) told me how much he wanted this experience and asked me to help fulfill his fantasy on our next get together. Let's call him Bob.

Now, please understand me; I'll always do whatever it takes to fulfill my SD's fantasy. If he wants another guy in the room, I am all for it. I have played the Bi role a few times for guys who have that fantasy, but hooking up with a girl is not my thing. I'd rather have extra cocks in the room for my pleasure. So I eagerly agreed to fulfill his fantasy for some extra dollars (I would have done it for free if he only knew how much I loved being fucked by multiple guys).

There were many discussions over text to understand what he was looking for. Broadly these were the agreements we made for the evening.

1. I would be in control and the dominant one. He would play a submissive role, and follow my direction.

2. We would fly down to Miami, and he would book a room at a fancy hotel for a night of sex.

3. I would get to pick whoever I wanted to bring to the room. There would be no rules around the kind of guy I would have sex with.

4. There would be no limits on sexual activities.

5. He would not get to participate, just gets to watch.

He understands he is not the best looking or well-endowed guy. While he knows that, he does not want to be laughed at either. BTW, my SD is 57 years old and has a beer belly and only a 5-inch cock. He loves the idea of all-night sex, but comes quickly and falls asleep early (easy money they say in my business). He is an eager pussy eater as he knows the only way to make me cum is spending time between my legs with his tongue and finger.

During these chats, I wanted to know if I could dial up the heat for him in ways that he may not be anticipating. He willingly agreed and gave me full control of the trip.

So for his fantasy night, he flew me down to Miami and booked a spot in one of those expensive resorts on the beach. I had already told him the clothes that he needed to buy and have ready. As I walked into the room, the dress Bob wanted to see me in, was lying on the bed with a few necessary accessories.

Given that I was in control, I decided to start my evening making Bob work on my pussy. We opened a bottle of wine, I stripped down to my sexy G-string and lay down on the bed with my legs spread wide. Bob knew exactly what he had to do, and dived between my legs, pushed my thong to the side and ran his tongue between my lips and on to my waiting clit, eating and fingering me to an orgasm. His tongue felt really good on my clit and his finger sliding into my pussy to play with my G spot aroused me quickly. My eyes were closed as I enjoyed the sensations. I was obviously fantasizing about the evening: meeting a new guy and fucking his brains out. Once Bob successfully gave me rather a good orgasm, he put my thong back on my wet pussy. He wanted the thong to be wet with my juices, so he could smell them later.

I wasn't ready to let Bob fuck me. Still, in just my thong, we drank, and I danced and rubbed against Bob all evening. We ate in the room. When it was time to start getting ready, I walked into the shower and asked Bob to join me. I made it clear he would get to pleasure me in the shower, but not to fuck me. I enjoyed a long hot shower while Bob rubbed my tits and body and even fingered me. I stroked his cock a bit and once even went down on my knees to suck him. However, I stopped well before he could cum. He did protest, but he also knew the rules for the evening. After a long shower, I asked him to leave, so I could get dressed up.

Bob took my cum soaked panties to the bedroom to get dressed. I know he loves to smell them and it excites him a lot. After getting my makeup done, I walked to the bedroom, still naked and slid this really sexy, backless, maroon dress, up over my hot nude body. It had a crisscross pattern in front that just covered my boobs but showed a deep cleavage and my pierced navel. Like all slutty dresses SDs buy me, they are tight on my body and short, to go just past my firm round booty. I never wear a bra, even in my normal life so the tight dress showed my nips very clearly. Bob requested that I not wear panties for the night. I enjoy the freedom of going out with no panties, so I willingly agreed. Bob had the sexy fuck-me boots that he wanted me to wear with this short dress. I got into them, checked myself in the mirror and admired my young sexy body.

My plan for the night was to pick a hot bartender to fuck. Miami is full of hot, young hunks. The challenge is not finding hot guys, but fighting off the many sluts like me who are in Miami looking for fun. So I took Bob to an upscale hotel bar. I knew the bartenders there were typically hot. In the worst-case scenario, there would always be some good-looking, business traveler who wants to get into trouble. The chances of finding someone hot, chiseled, with a big cock was high.

As I suspected the bar was full of guys, a few hot girls, some dates, but definitely 10 guys for each eligible, single girl. Bob and I made our way to the bar and decided to settle there. I could not have been more lucky, as behind the bar stood Alex, an Australian dude. I immediately knew I needed to play my cards right and ride his cock. Bob knew that I was secretly craving this hunk.

We ordered drinks, and I flirted with Alex openly with Bob next to me. Alex quickly realized that I was Bob's paid date. I will not bore you with details, but I made no qualms of letting Alex know that, if he was free, I would love to take him back to our room. I wanted him to know this was Bob's fantasy, that he would be an onlooker only, and if Alex liked the idea, he should come over. Alex was far kinkier than I imagined; he willingly agreed and asked if I wanted his friend to join us?

This was music to my ears: two guys fucking me would be so hot. I asked him about his friend and learned that Derek, his room-mate, was a black guy, 26 years old and a gym instructor who would love to show me a good time. Evidently, the two guys had taken care of a few girls previously.

Around 2 AM Bob and I made our way back to our hotel. We were both buzzed. Once in the room, I asked Bob to strip and sit naked on the sofa. I left my dress and boots on and sat on his lap as I ground my bare pussy on his cock. There was music being played in the room as I gave Bob a seductive lap rub/dance. Bob had his hands on my ass, pulling me closer into him. I reminded him that tonight this pussy was off-limits for him.

After about 15 minutes, the doorbell rang. I opened it to see Alex and his freaking hot roommate Derek standing outside. Alex leaned in and kissed me on my lips. He was tall, so I was on my toes, and he ended up picking me off my feet as he held me kissing. Alex was an excellent kisser and had great fresh breath. Derek followed him in but made no move. The three of us walked into the bedroom and noticed that Bob was clearly excited. He sat there stroking his 5-inch cock thinking about the black and the white guy fucking me for the night.

After opening more drinks for the guys, I made my way to Derek and kissed him. He was a wonderful kisser too. At 6'4" tall, he almost picked me off my feet as he held me in a deep kiss. My short dress rose as he held me up to show the guys my naked ass. While Derek held me, Alex walked over and grabbed my naked and very exposed ass, squeezing the cheeks hard.

"You are a fucking slut who has no panties on," said Alex as he groped me.

Derek dropped me down to my feet and pushed one hand under my dress from the front to feel my pussy. Having both the guys grope me felt so good especially with Bob sat naked watching.

I asked the guys to take me and fuck me hard. They needed no more invitation. They threw me on the bed, almost ripped open the dress, but left my boots on. Derek moved to the top of the bed and shoved his 9-inch black cock in my mouth. Alex, opened my legs, put on a condom and pushed his 8-9 inch cock into my tight young pussy. He was violent and hard, fucking me with so much intensity that it hurt. I had to pull Derek's cock out of my mouth and tell Alex to slow down, but he didn't change the way he was pounding that shaft into my pussy. I knew all he cared was about cumming hard.

Derek, on the other hand, had his hands in my hair, and he tried pushing his entire cock in my mouth. I am good with my gag reflex, so I managed to take all of it.

"Look at her swallow my cock Alex," Derek said, not without a little admiration for my skills.

Alex pulled my hips against him and replied, "Her pussy is really hot and tight Derek."

I was enjoying being used in front of Bob, even though Alex was hurting me a bit. I was convinced Alex was going to cum, but almost on cue as my first orgasm hit, the guys swapped position and Derek was in my wet and very sensitive pussy. Derek was a slow but deep stroke kinda guy. He called me all sorts of names as his black cock fucked my white pussy.

Bob was soaking all this in. He walked up to us and asked if I would suck his cock or stroke it at the very least. He was quickly reminded he could watch but not join in. I don't think he liked my answer, but he surely was enjoying the views, and this was, after all, his fantasy.

Soon the guys decided they needed to DP me. Alex lay down on the bed and asked me to jump on his cock, facing him, sliding his cock deep in my pussy. With my tight ass open for Derek, he slid a condom on, lubed it up, and soon had his cock in me. Wow! that felt so full. I love DP and this was one of those nights. I think I came within minutes. The guys wanted to experience both positions, so they swapped roles and Derek was in my pussy and Alex in my ass. They fucked me to another orgasm.

The guys were ready to cum. Derek wanted to go first, so he threw me down on the bed, opened my legs and jumped on me to fuck me missionary style. We were kissing and fucking. Bob was right next to us watching; he jerked himself till he came all over the bedsheet. Derek hardly noticed - he was too busy and soon his cock was exploding deep in my pussy. I could feel his hot cum fill the condom. He groaned and moaned as he let the last drop out, then pulled his somewhat limp cock out of me and headed to the bathroom.

Alex, who watched his room-mate fuck me, asked me to join him on the sofa. He sat down and I straddled him and guided him into my freshly fucked pussy. He grabbed me by my ass and helped me ride his cock. The fuck me boots looked so good on my naked body as Alex enjoyed fucking me.

I wanted to cum one more time. I told Alex to fuck me doggie style by the hotel window. The exhibitionist risk and doggie position is always guaranteed to make me cum. And I did, for the third time!!

Alex having fucked me in so many positions, was ready to cum. He asked Bob if he could cum all over my face and boobs to mark me as the slut for the night? Bob agreed happily. Soon Alex had me on my knees, sucking and stroking his cock. I know exactly what guys love that makes them cum quick. I had Alex soon exploding his jizz all over my face, my open mouth, and tits. I kept stroking his cock to get every dropout and then sucked him clean.

Both guys were delighted with the evening so far and asked Bob if they could stay longer, recover, and fuck me more for the night. I could see Bob was tempted, but he refused and said their job was done and that my naked, used body was his for the remainder of the night.

While the guys left, I cleaned up the cum from my face and boobs; I thought of asking Bob to do it, but that may have been a step too far. I was headed to the shower when Bob came in and asked me to suck his cock in the bathroom. I did what he asked and once he was hard again, he pulled me into the shower, made me face the wall, opened my legs and entered my pussy bareback. Under the hot shower, Bob fucked me until he came in me. Not too much cum but enough that I could feel it. He pulled out, cleaned up and left for the bedroom. I took my time enjoying the hot shower, thinking about the two hunks who had fucked me so hard, touching myself gently as I stood soaking.

Once I was dry, I walked to the bedroom, dropped my bathrobe and slid under the sheet naked, to cuddle against Bob's naked body. "Did you enjoy tonight?" I asked.

"More than you would know. I want you to invite someone else tomorrow night to fuck you, but this time I will join in." I needed no cajoling and I kissed him and nodded. "Tomorrow, you pick the guy you want to fuck this tight body, baby," I said as I shut my eyes.