The Baller Pt. 01

This story starts out as a true story, but with many cases fantasy is more fun than reality and that is where it will go. If you want to know where reality ends and fantasy starts, please ask.

I was doing what I usually do in the evenings while traveling. I was online, playing with myself and fantasizing. Traveling for work can be very boring. It was Thursday and I was consulting for an aerospace company. I had gone straight from work to eat, and I was in my suite at the Residence Inn. I had been drinking, masturbating, and edging for several hours and I had wandered my way from pictures to movies and I had now set up a local chatroom "SeekingDomMale". I had been fantasizing about meeting someone and had done it a few times in other cities while traveling. I was aroused enough and tipsy enough to go through with it. Most chats started and ended quickly. I am sure the guy on the other end either chickened out or came from masturbating and logged off. One did not though.

I had brought myself to the edge of orgasm multiple times when SirCharles started chatting with me. He was not really a conversationalist, and I don't think he was really experienced in BDSM or kink. He just knew what he wanted. He wanted to fuck a man. I really wanted sex with a dominant man, and I made it clear that my only objective was to submit and please him. I did not need any reciprocation. I did not need to cum. I was honest about this. My fantasy was to be used and fucked by a dominant man and to not cum. I was fantasizing about him coming over fucking me and then leaving me horny and frustrated.

It was a short chat. I offered to do anything he wanted as long as it was safe. He could come to my hotel room and use me any way he wanted. I probably sounded desperate, and I was. I wanted anyone to come over. I was a little surprised when he said yes and asked me for my hotel room number. I gave it to him and said he would be over in 15 min.

Now I was really nervous. If you have met a strange man on the internet, you know how nerve-wracking it can be. Is it safe? Will he be attractive? I had not seen a picture, and this was the days before video chat. I was nervous and I quickly drank two more beers to calm my nerves and wait. After about 10 minutes I was looking out the window at the entrance to the hotel. It was after 10pm so there were not that many people coming in. I only saw one and he was a big black guy dressed casually and about my age. He sauntered up to the door which was two floors below and about 30 yards away. He had to be over 250 lbs. and over 6 ft tall. I was a little scared. I am 5'10 and 175lbs.

It was too late to back out. He knew the room number and I had left the door cracked open. When he knocked, I opened the door, said hello and invited him in. He was calm and walked in. He seemed to be nice enough and was not really threatening, but he was imposing. He was several inches taller than me and much heavier. He was not fat but not trim either. I noticed a gold medallion that was one of the mascots and names of one of the two big state Universities. I suspected and would find out later that he had been a lineman in a division 1 school.

There was not a lot of small talk. I stood in front of him and said, "What can I do for you sir?"

"You can start by sucking my cock."

I didn't hesitate. I started unbuttoning his pants and reached inside and pulled his cock out. It was huge. I started stroking it and it was getting hard quickly. I had a condom on the counter beside me and opened it and was struggling to get it on, because of the size. I wanted this cock in my mouth. With the condom on I knelt in front of him and wrapped my hand around his cock and put it in my mouth and started sucking. The first thing I noticed was his smell. I did not have a lot of experience with gay sex, and this was new to me. It was powerful and musty. The next thing I noticed was And there was no way I was going to deep throat him. I had been practicing deep-throating dildos and I really wanted to try it in real life. This cock would barely fit in my mouth and there was no way it was going down my throat. I tried but quickly realized it was impossible.

I was a little worried now, because I wanted to please him but my hand stroking his shaft and my mouth which was barely getting past the head of his cock was probably not going to be enough to please him and I really wanted to please him.

He confirmed my suspicions a few seconds later when he grabbed my head and pulled it off his cock and said, "take off your clothes and get down on your hands and knees."

This was daunting. I had put buttplugs and objects in my ass that were huge, but I had only had anal sex once and with an older man who was much much smaller. I quickly took off my clothes and he undressed. I had cleaned myself out as best I could earlier without an enema kit, and I had put some lubricant in my ass. I knelt down in the den on the carpet. He knelt down behind me and put his cock against my hole and pushed in. I always love the first penetration, and this was wonderful. It was not the biggest object I had inserted into my ass, but it was longer and wider than any dildo I had fucked myself with. Once in he put his huge rough hands on my hips and started pushing in. I loved every inch as he went all the way in. I was happy that I could take him and was hoping that this could please him.

He started slow but sped up and was fucking me harder. It felt so wonderful, and my dick was dripping precum. My knees were also getting raw on the carpet. He was pushing so hard that I would slip forward a little each time he thrust. His knees may have been feeling it too because he stopped and told me to get up on the bed. It had only been a minute or so, but I quickly jumped up on the bed. I started to get on all fours, but he told me to turn over. I rolled onto my back, and he grabbed my ankles and pulled them back towards him at the edge of the bed. He was standing holding my ankles and I grabbed his cock and pushed it against my hole pulling him back inside me. He let go of my ankles and I put them up on his shoulders. He leaned forward pushed into me hard. I was looking up at this beautiful huge man. I was running my hands over his powerful arms and chest looking down at his belly. He would pull out of me slowly until just the head was in and then he would push back in quickly and hard. It was heaven and I moaned almost yelling with each thrust.

My own cock looked tiny bouncing on my belly. It was almost limp and looked small because my legs were up over shoulders. Each thrust felt wonderful, and I could feel an orgasm building even though I was limp, and nothing was touching my cock. I didn't know what to do. I couldn't stop it. I really had planned on letting him fuck me and come without getting my own orgasm. What was worse was that we had only been on the bed a few moments. We had been fucking less than 4 minutes and I knew he was nowhere close to orgasm. I was about to premature ejaculate without anyone touching my cock. I was mortified and sorry

When I reached the point of no return. I moaned, "Please let me cum."

I was surprised when he said, "OK'

I was expecting him to stop and tell me no, but he was not real experienced at BDSM, and I guess the normal reaction is to say yes when someone asks to cum. He was still fucking me in that slow out and hard thrust in and there was nothing I could do. I was straining not to cum, but I did. Yelling out and clenching every muscle in my body I had an orgasm that was very different from my normal but oh so wonderful. It came from deep in prostate and flowed through my body

SirCharles stopped fucking me, looked down at my cock as it oozed cum out all over my belly and said, "Wow, you came without even touching it."

That was my thought exactly. How had that happened? I didn't know but I had loved it. Charles pulled out of me finished. I quickly sat up and grabbed him before he could move away from the bed.

"Please don't stop," I pleaded. "I haven't pleased you. I am sorry I came. I only wanted to please you and make you cum. I am sorry I came first. Please forgive me. Please come back. Keep fucking me. I really really want to please you."

I was babbling. I was desperate, embarrassed and sorry. I was pulling him back towards me and pleading with him to keep fucking me.

He stopped pulling away and looked down at me. "You really want to keep fucking even though you already came?"

"Yes please. I really do. I really want to please you. Fuck me more and tell me what to do to please you."

He stepped back between my legs and pushed his cock head back inside of me. I was focused on him and wanted to do anything I could to please him. My hands were all over him caressing him and reaching down to cup his balls and kept fucking me. I was panicked that he was not going to cum and I was babbling trying to find out what he liked, what he wanted.

"Please fuck me and cum inside me. Please let me please you. What do you want me to do?"

He was not the great conversationalist, and he was not giving me any feedback. He wasn't slowing down either and each hard thrust in and slow pull out felt great. I did not know what to do to make him feel better and cum. I decided to lead the conversation and give him a chance with easy answers.

"Do you like having a submissive slave that will let you fuck them any time you want?"

This got a response. He grunted, "Yes" as he pushed hard inside me.

"Would you like me to be on call to make you cum any time you ask?"

"Yes."

I was figuring out that open ended questions were not working, and my mind was scrambling to formulate better questions. He was sweating now because he had been fucking me in earnest and breathing harder. I did not think he was close to orgasm though.

"Would it turn you on to tie me up and fuck me next time?"

"Yes."

"Would you like to spank me and hear me yelp"

"Yes."

I had my hands on his balls and I could feel them tightening. He was tiring but thrusting harder. "Do you like Leather, lace, Lingerie, tickling?" I hoped not tickling but I was babbling anything I could to find what turned him on.

"Lingerie."

That was unexpected but I loved it. I had cross-dressed often and from an early age.

"Roll over please and let me get on top of you." I begged.

He climbed up on the bed and lay down on his back. I climbed on top of his sweaty body, reached back and put his cock back inside me and lay on top of him. His cock was long enough that it would stay inside my ass even as I kissed his neck and continued whispering in his hear

"Would you like me to wear lingerie for you next time? I will be waiting kneeling in the middle of the room when you walk in, or I will serve you beers and kneel in front of you while wearing lingerie?"

I was looking for the response and this was getting one. "Would you like me to dress completely as a woman for you?" I whispered in his ear.

"Yea, I'd like that."

"Do you want me to dress slutty or girl next door? Do you want me to be your hooker or your suburban housewife?"

This was having the desired effect. My little fantasies were doing what my inexperienced sex life could not. He was getting more turned on. I was also getting close to an orgasm again. The effect of bouncing on his cock while my cock was rubbing on his belly was really turning me on.

He smiled as he said, "I want a little suburban housewife that craves my big black cock."

"Does your suburban housewife wear dresses or pants?'

I was licking his earlobe as he said, "Dresses, no pants."

"Does she have long hair or short hair?"

"Long"

"Does she have long nails or short nails?" I was really hoping he said long because I have a huge fetish for long nails

"Long." I was happy to hear him say.

I had reached orgasm again with my semihard cock rubbing between us on his belly. I begged him again, "please can I cum.

"Before he could answer I did, exploding and clenching every muscle in my body especially my sphincter. This must have felt good to him because he started thrusting upward. I did not stop fucking him as my orgasm came and went. I was determined to make him cum. He was getting closer, and he was thrusting up into me as I thrust down. I sat up on top of him so I could get more of his cock inside me and redoubled my efforts. I also kept talking dirty to him.

I was telling him a story of his suburban housewife mistress who was going to meet him next time and fuck him.

It did the trick. My dirty talking had him aroused and he was fucking me hard as he finally came slamming into me. I was squeezing and milking his cock as he finished and then I stopped and lay down on top of him. He was done though. He pushed me off him and I disappointedly rolled off. I went into the bathroom and got a washcloth and met him as he was standing up. I cleaned up the mess on his belly and took the condom off him and washed his cock. He just watched me. I took the used condoms and the washcloth to the bathroom and came back with a fresh washcloth and cleaned him up some more. When I went back to the bathroom he started getting dressed. I came back out naked and watched him finish dressing.

As he stood up to leave I started babbling again, "Thank you so much, I really loved that and I am so sorry I came, well, uh, came twice. I really did not mean to. I really just wanted to make you cum."

He was uncomfortable and ready to leave.

"I really do want to see you again. I would dress as your suburban housewife. I will be your total slave. Long nails, cute dresses, high heels, long hair! You name it and I will wear it and act any way you want."

He didn't know what to say. He was a typical post orgasm male. He was done and muttering an awkward goodbye. I did not have any way to contact him, and I really wanted to see him again. An orgasm with only anal sex had been amazing and I wanted more. It was obvious that he wasn't an openly gay person, and this was supposed to be a one-night stand. I quickly grabbed a pen and paper and wrote my email address on it. I told him I would be back in 3 weeks for a week, and I would be willing to do anything he wanted. He took the slip of paper and left without committing to anything. I was hoping that I would hear from him again, but I was scared that I would never see him again.

I went to the shower to clean up before bed. The dirty washcloth was on the sink with the condom full of his cum on top of it. I picked it up to throw it away but then changed my mind. I wanted it. I wanted to drink it down, but I paused because I had no idea if that was safe. I didn't know Sir Charles and I didn't know if he was disease free. I climbed into the tub and did something that was safer but not completely safe. I knelt down, looked up and emptied the cum all over my face. It ran down my face and only my chest down to my crotch. I started masturbating furiously. My cock was rock hard for the first time since Charles started fucking me. I wiped my hands in the cum and used it to lubricate my cock and I relived the fucking I had just received, and I came yelling for the third time that night.