On My Knees in Vegas Ch. 04

James and I took the elevator from the 47th floor to the main conference floor at the sumptuous Dvara hotel in Las Vegas. My daddy brought me to Vegas yesterday for a naughty business trip to a convention. We made love several times already starting with a covert blowjob I gave him in a bathroom stall at our airport. Since then James enjoyed numerous cums in or on my body.

So while James' cute little wife Susan is at home I am satisfying her husband in every possible way. I am James' horny little crossdressing cocksucker. I love pleasuring him and he loves fucking me which gives me a great deal of satisfaction.

On this trip I was posing as James' nephew. In public I would dress like a typical grungy 18 year old. But when we were alone I would transform into a slim young woman with shoulder length blond hair and a big curvy bust. I wear a range of lingerie including babydolls, night gowns, slips, basques and of course, panties and bras. I have big silicone fake titties to fill out my bras and James seems to love squeezing them which makes me feel so feminine. Although not as feminine as I feel when his beautiful cock is pushing its way into my mouth or love-hole.

The elevator seemed to stop at every floor and filled up with people, mostly men, until it couldn't take any more. Still it kept stopping until we reached the conference level.

The elevator doors opened to a huge ball room with a long breakfast food bar on one side and dozens of big round tables. We went straight to the food bar and helped ourselves to scrambled eggs, flapjacks and other goodies. I was accustomed to eating heartily as I had been on the high school swim team for years and did a lot of training. I didn't have an ounce of fat on my body and my slim looks plus the fact that I was only 5" 8" tall were great assets for me when assuming my femme persona Diana.

Some of my other assets were my ever-more-experienced lips, my ability to take a cock down my throat and my well used tight little bumhole. My eagerness to suck and fuck was the cherry on top.

James owned a small chain of grocery stores back home and comes to this Independent Grocers of America convention every year. This is one of the places where he connects with suppliers which sometimes leads to new contracts.

James was concerned that I might get bored hanging around. And he encouraged me to set out to explore Las Vegas on my own. But for now I preferred to stay with him and see what the convention was all about.

And it was kind of fun seeing all the men milling around and wondering how many of them were frustrated with their sex life with their wives and needed a public service blowjob.

There were kiosks along the wall opposite the food bar where pretty 'booth babes' were setting up posters and pamphlets. I loved watching pretty women. I learned a lot about how to dress and act sexy from them. And I loved and envied their breasts. I loved feeling women's breasts although I had only enjoyed the experience a few times. My disappointment with dates with girls my own age led to my discovery of dressing up for men. It was just so easy to get men to fuck me and once I started pleasuring men there was no going back.

We took our tray to a table in the middle of the ballroom where James knew some of the people already seated.

After a round of handshaking James introduced me as his nephew Dana. "Good to meet you Dana," said Bill. "Is James grooming you for the grocery business?"

The choice of the word 'grooming' struck me. In fact James was grooming me, but not for the grocery business.

"No, not at all," I replied. "I'm just tagging along to see Las Vegas. It's my first time here."

"Well welcome to Vegas, Dana. I hope you don't get into any trouble!"

"Oh no, I'm very well behaved!"

The other guys were done their breakfasts and were sipping on coffee but we had to hurry as we were a bit late. The opening session would start in 15 minutes in the ballroom next door. Of course we were late because I had given James a lovely good-morning blowjob before we came down. I was still savoring the taste of his cum as I hadn't brushed my teeth yet.

After breakfast we went to the adjoining ballroom for the opening session. The convention kicked off with a long speech about shrinking margins in the grocery business and the plight of farmers. I wasn't in the mood to listen to it so I whispered to James that I was going to take a walk around Las Vegas.

I got up and worked my way to the aisle to leave. I decided to stop in the men's room on the way out. The huge bathroom was empty. I was absent-mindedly having a pee when someone appeared at the urinal beside me. That was weird as there were 20 empty urinals and this guy had to choose the one beside me.

"Hi again, Dana."

I looked over and it was Bill.

"Hi Bill. Didn't find the speech too interesting?" I asked.

"Not really. I've heard it all before. I come to this trade show every year so it becomes repetitive."

Bill paused to start peeing. It sounded like a firehose. 'He must have a big cock,' I thought.

"How about you?" Bill asked.

"I was actually going to go for a walk," I replied.

At that moment Bill put his hand on my bottom and massaged it. He was taking the liberty of feeling me up. I didn't know what to say so I didn't say anything. I just stood there.

Bill interpreted my inaction as consent. He continued to feel me. Then he slipped his hand into the back of my pants and felt my bum through my silky panties. I shook my dick and zipped my fly.

"Are you really James' nephew?" Bill asked while fingering my crack. "Or are you something more? I figure you're a gay sissy. Why else would you let me feel you up? And why are you wearing girl's panties?"

With that I pulled his hand out of my pants and stepped away from the urinal. "It's none of your business whether I'm gay or not," I said defensively.

Bill turned toward me. "It's ok if you're gay. But if you like sucking cock I could sure use a blowjob."

My jaw dropped. I couldn't believe this guy was so being so blunt.

"Hey," Bill continued. "Instead of going for a walk you could come up to my room and we'll get to know each other real good."

I hesitated. I had to admit I was intrigued. Bill was fairly good looking. He was in his mid 50s and had a stocky build. I could see big muscular arms through his shirt sleeves. And from what I could tell he had a big cock.

I was beginning to succumb to Bill's crude come-on. After all that's what sissies do - pleasure men who are in need of relief. I am very vulnerable to direct demands for sex.

Bill reached out and took my hand. "Please, come play with me. I know you'll enjoy my cock." Then he gave his cock a shake and turned toward me so I could see it. Although it was limp, it was big! I felt weak in the knees.

Bill tucked his cock in his pants then led me to the bathroom exit. In a moment we were standing in an elevator waiting for the doors to close. We were the only people in the elevator. As soon as the doors closed Bill swung me around to face him. He put his arms around me and started kissing me passionately. I melted into his big strong arms and kissed him back. His hands were all over me and one slipped into my panties and was probing my crack. A finger found my love-hole and massaged it.

I broke the kiss for a moment, "if we go to my room I can dress up pretty for you."

"I like the sound of that!"

I pressed the button for floor 47 and resumed French kissing Bill. I hoped we would be alone in the elevator until my floor.

The elevator bell 'dinged' and the doors opened. I took Bill's hand out of my pants and led him to my room.

"Wow," Bill said as I opened the door. "You have the luxury suite!"

"Yeah, pretty nice. You make yourself at home while I slip into something more comfortable."

Bill sat on the couch while I went to the bathroom and shut the door. My suitcase was open on the bathroom counter displaying all of the lingerie I brought.

I wanted to get dressed quickly but decided it was worth a couple of minutes to put on a garter belt and stockings. I love feeling a man's hands on my stockings sliding up my leg reaching the bare skin at the top. And I love the feeling of straddling a man's big strong legs with my stockings. I can't describe how it makes me feel so feminine and aroused. My cock was rock solid just thinking about it.

The garter belt was satin with lots of lace trim. But it was black so I took off my pink panties and selected a pretty pair of sheer fullback black panties. Of course my stiff little pickle was sticking out and tenting the panties. Oh well, I am a horny sissy with a new man waiting for me on the other side of the door.

I took off the camisole that I had hidden under my boy shirt and put on a black lacy bra. I held the cups open and inserted my big heavy breast forms. I held my tits up in the mirror and gave them a little squeeze. I thought they looked pretty good!

Finally I put on a semi-transparent black babydoll with puffy sleeves and a puffy bust gathered under the boobs. The babydoll came down to mid-thigh and was trimmed with a wide band of lace. My tits pushed out the front of the babydoll so it hung out in front of me. It sort of didn't fit well but the effect was to make my fake tits look huge. Most men seemed to love the look.

I finished getting ready to be fucked by quickly putting on some dark purple eye shadow and bright crimson lipstick that I call 'cocksucker red'. I puckered my lips in the mirror. I was ready to enjoy a juicy new cock!

I opened the bathroom door. Bill was sitting on the couch with his erect cock in his hand. His hard-on was huge! He was gently stroking it.

"Hi there big guy," I said as I walked toward the bed exaggerating the swaying my hips. I pushed aside the rumpled blankets of the unmade bed where James had fucked me only yesterday. I lay on my side propped up on an elbow looking at Bill.

"Shit you look better than I expected!" he said. I smiled at this back-handed compliment.

"I'm glad you think so Bill. I see your cock is happy with my looks too!"

Bill stood up and kicked off his trousers. He looked funny naked from the waist down as he was still wearing a white shirt and tie. His big cock was sticking out like a billy club. I couldn't wait to wrap my lips around it.

Bill walked over to the bed and stood in front of me, his big beautiful penis only inches from my face. I could smell his musky crotch aroma. I nearly fainted with erotic overload.

I turned my body slightly toward him and leaned forward until the tip of his cock touched my lips. He was circumcised. His cockhead was the size of a big plum and was purple like one. I used my tongue to lick up a big drop of precum.

He pushed his hips gently toward me while reaching behind my head to take control. My lips parted automatically and his cock started to enter my mouth hole. But I had to reposition a bit in order to open my mouth wide enough to take his cockhead fully into my mouth. It was big. But there was room for me to swirl my tongue around it and that's how I started Bill's blowjob.

Bill was assertive. He quickly started fucking my mouth and pulling my head toward him with both hands. I could hardly get any more of his cock in my mouth beyond the head.

Soon I had to reposition and Bill guided me to lay on my back with my head over the edge of the bed. This is when Bill really got his mojo going. He fucked my mouth hard eventually getting more of his dick into my mouth but making me gag uncontrollably. My noisy gagging and spluttering seemed to turn him on. Bill fucked my face hard as I hung onto the back of his legs.

Just when I was beginning to wonder how long I would have to endure the ordeal, Bill put all of his weight on me with his hands on my tits, and started driving his cock as hard as he could into my mouth. He bucked and grunted a huge load of cum into my throat as I gagged and gasped for breath and thrashed my legs.

I admit it was a relief when Bill was done. And although the mouth-fucking I just received was uncomfortable for me I was overcome with a wave of satisfaction knowing I just relieved a very horny man who obviously hadn't cum in a long time. Poor guy. I was so happy to be his stress relief cocksucker.

As Bill pulled his softening cock out of my mouth I realized that my stiffy was still poking up in my panties. I had to cum in the worst way but proper sissy etiquette prevented me from touching myself. It was my man's prerogative to allow me to cum if he wants me to. And it's impolite for a sissy to ask her man for relief. In fact that's a good way to get a spanking. Often a man just waves me on to jack myself off, but Bill paid no attention to my hard-on.

Bill sat on the bed beside me. "That blowjob really got me off. You're quite the cocksucker. Your 'uncle' is lucky to have you around this weekend. Must be fun for both of you."

I sat up on the bed. I reached for the kleenex to wipe saliva and semen off my face. Spit and cum were all over the front of my babydoll. I could see in the mirror that my lipstick was a mess. But I was proud to look like a proper slut who just got the living daylights fucked out of her.

"I'm glad you enjoyed it Bill," I replied. "It was a privilege to take such a big cock. I constantly want to improve my skills and experience."

"Well you've got good cocksucking skills, that's for sure! I wonder how you are fucking."

"Oh my, I'd have to get good and stretched before taking your monster cock! But I'd love to try!"

"Good because I'm not in a hurry." Bill leaned over to kiss my sore cummy mouth. Our tongues mingled while Bill stroked my cock through my panties.

"I bet you're read for a cum too," Bill said with his hand curled around my little boner.

"Oh yes, I'd love to cum Bill!"

"Well let's kill two birds with one stone. I need a bit of a break but you can climb on top of me and frot our cocks until I'm hard again. Hopefully you'll cum that way."

I put my arms around Bill and spoke into his ear, "I'd love to rub our cocks together. It's one of my favorite naughty things!"

Then I hiked up my babydoll and slid my stocking-covered legs over Bill and positioned my stiffy on the big heap of soft warm man flesh that was Bill's cock and balls.

I reached for the lube (there were at least three little squirt bottles of lube in the room). I dribbled a generous amount on my cock and pushed it into his cock. The warmth of Bill's dick felt wonderful as I started massaging our cocks together. I knew I wouldn't last long.

I sat on Bill's thighs and looked into his eyes. I couldn't stop smiling. I was so glad I brought Bill to our room and I knew James wouldn't mind. In fact that old pervert would want to know every detail of my encounter with Bill and make me do the same acts in the same way with him.

Bill's cock started to respond to my hand action. He was getting harder and I was getting closer to cumming. As Bill's cock got bigger I got more turned on. I upped my handjob tempo. Our cocks were kissing between my slippery hands. Sliding my hands up and down felt so good.

Suddenly, that overwhelming wave of pleasure washed over me. I closed my eyes and let my load shoot out where it may. I felt cum mingle with the lube on my hands. When I stopped panting and opened my eyes I saw Bill rub a drop of cum off his chest and wipe it on the sheet.

"Looks like you had a good one," Bill said. I realized my hands were still wrapped around Bill's cock and it was fully erect now. I wondered how I was going to accommodate this big cock in my tight little boi-pussy.

"And looks like you're ready for another round!" I replied.

I swung my legs off and snuggled up beside Bill. My cock was finally soft. I kept one hand on Bill's erection and stroked it gently.

"I'd love you to fuck me," I whispered in his ear.

"I'd like that too. Can you take a cock as big as mine?"

"Only if I'm stretched first with a dildo." Luckily I had brought a sizable dildo on the trip. It's wasn't as big as Bill's cock but close enough to help me take him without unbearable pain.

I opened the drawer of the bedside table. "Here's the dildo. Would you like to do the honors?"

I rolled away from Bill onto my side exposing my bum to him. He lifted up the hem of my babydoll and pulled my panties down a little. I lifted my hips so he could pull the panties down to my thighs.

Bill felt my bum with both of his hands. One finger always dancing around my love-hole. Bill poured some lube on his hand and smeared it in my crack. Then he started to work it into my bumhole with his fingers. It felt very nice having a man play with my rosebud. I relaxed.

Then Bill lubed up the dildo and pushed the head against my entrance. He alternated pressure and release to slowly make my bumhole open. I could feel the head of the dildo get a little bit further in on every stroke.

I rolled onto my tummy to give Bill better access to my bum. I enjoyed feeling my big fake titties squashed between my chest and the bed. I'd be rolling on my tits soon if Bill fucked me in this position.

Bill continued to work the dildo into my bumhole. I'd used it many times so I knew it wouldn't be too difficult to insert. It was starting to feel good! I moved my hips in response to Bill's thrusts.

Bill pulled the dildo away and pressed the tip to my lips. I stuck out my tongue and licked it.

"You really are a slut," Bill said.

He dribbled more lube on my hole and worked it in with his fingers. I moaned with pleasure.

"You're already enjoying it and I'm not even fucking you yet!"

"I can't wait for you to take me Bill," I replied. "But keep going with the dildo."

Bill slid the dildo along my crack to pick up some of the lube. "Ooo that feels good!" I cooed. Then he pressed the tip of the dildo on my bum hole again but this time he pressed harder and I could feel my o-ring begin to yield. The dildo was entering my bumhole and that familiar fullness felt wonderful.

"Bill, you're doing such a good job preparing me. I can't wait for your cock inside me!"

"We're getting there," he replied as he kept pushing the dildo further into me.

Finally the head of the dildo was fully inside and then Bill pressed it home until the silicone balls were touching my cheeks.

"There you go you little slut!"

"Oh, Bill it feels so good! Please keep fucking me, please!"

Bill slowly pulled the dildo almost out of me and then pushed it all the way in. He kept it up for a while as I lay on my squashed titties and moaned with pleasure. The silicone cock felt so good but I was starting to look forward to Bill taking me with his huge manly cock.

After a few minutes Bill withdrew the dildo and set it aside. He grabbed the lube and knelt right in front of me with his cock practically in my face. "Perhaps you can lube me Dana," he said handing me the lube bottle.

"I'm 'Diana' when I'm dressed up, just so you know."

"Oh, sorry Diana. Makes sense That's a pretty name. It suits you!"

I got up on one elbow and took Bill's magnificent cock in my hand. With the other hand I squirted a generous amount of lube on his shaft. Then I started spreading the lube all over his huge cock with my hands.

"Mmmmmm, that feels good Diana! Keep going!"

I wondered if he wanted me to give him a hand job instead of fucking me so I just kept going with my sensuous cock massage.

"Okay, now back on your tummy. I want to fuck you."

Dutifully I returned to my tummy position with my ass cheeks exposed for Bill's pleasure. I slipped my little cock forward under my tummy. My panties were still pulled down around my thighs. I could see us in the mirror. Me in stockings with my babydoll pulled up and my panties pulled down. Bill with his shirt still on and a big erection swinging around.

Bill climbed on top of me and pressed his cockhead on my pucker. Even though I was loosened up it was going to be hard to get his huge cock inside me. But it was my duty to pleasure him so I was going to do whatever it took to accommodate his manly penis.

He pressed harder and squeezed the base of his cock. The head was hard alright. I felt my hole begin to yield.

I tried to think of other things to distract me as the discomfort increased with every push.

"I'll squirt a little lube right on your hole," Bill said pausing.

I felt a few drops of cold lube on my bottom and Bill started pushing his cockhead against my love-hole again. This time it started to yield to his enormous cock. I grabbed the sheets in my hands preparing for a lot of pain, but that didn't happened.

Instead Bill's cock managed to force itself into me, stretching my hole to the max, but it didn't hurt at all. "How does it feel sweetheart?" Bill asked considerately.

"It's fine love, go ahead and enjoy me. Fuck me as hard as you like!"

Bill repositioned himself so he was mostly on his knees behind me. Then he took off his tie and shirt and tossed them on the bed beside me. The thought of a man taking off his clothes to enjoy my body really turned me on.

Bill leaned forward and pushed his cock into me again. It felt wonderful! I couldn't believe I was being fucked by such a well endowed man and enjoying it so much.

Then I had a flash of worry that James might be jealous if he knew how much I was enjoying getting laid by his buddy Bill. I hoped James would just be proud of me.

Bill was going to town on my ass. He was fucking me fast and deep. His big warm balls pressed against my bum on every thrust. Being on my tummy I couldn't do much to contribute to his pleasure. I just did my best to push my bum toward him to meet his thrusts. I tried to rub my stocking covered legs against his which I think turned him on.

Bill was starting to run out of breath and was sweating all over me. Suddenly he stopped fucking me and rested on me.

"Wow what a great fuck!" he said between breaths. After a few more breaths he said, "I want you on your back now" and he rolled off of me.

I was thrilled because missionary is my favorite position. I'm not sure why but I think it's because that's how I imagine most wives getting fucked by their husbands. It's the 'wife' position not the 'missionary'. Dutifully I turned over onto my back. I spread my legs and raised my bum to give easier access to my love-hole.

Bill sat up and shoved a pillow under the small of my back to raise my bum a little more. "That's better," he said.

Then he crawled between my legs and rested on his knees looking at me. His gaze scanned my body then stopped at my eyes. "You look absolutely beautiful Diana. I can't believe I'm fucking such a pretty girl."

"It's so sweet of you to say that Bill. I'm so glad you find me attractive. I hope it helps you have another great cum!"

"You bet it will," Bill said as he positioned his cock at my entrance and leaned forward to kiss me. I put my arms around his neck and gave him a passionate wet kiss. I kept kissing him as I felt his enormous cock slide into me again.

"I'm not going to last long," Bill said as he started to pump me with his cock. "But I'm going to try."

On my back I could respond much more to Bill's movement. I met his thrusts by arching my back and pushing against the bed with my hands. Then when he slowed down I would throw my arms around his back and let him gently fuck me. My tits squashed under his hairy chest.

We did this cycle of pleasure for a long time until Bill suddenly leaned forward to kiss me - "I'm gonna cum Diana!"

Bill closed his eyes and seemed to hold his breath. His cock was motionless inside me for a moment. Then with an almighty thrust he started bucking his cock as I tried to hang on to him and not be thrashed to pieces.

Bill's orgasm was much more intense than the first one he had in my mouth. I guess his cock loves my love-hole.

With one last thrust Bill collapsed on top of me panting. I could hardly breathe but I lay there with him for as long as I could so he could enjoy the afterglow of his climax.

Bill's body was pressed against my big fake titties and I could see the fabric of my bra and babydoll stretched tight. I truly felt I was in a woman's role having just been fucked by the exhausted man on top of me.

But I had to wriggle out from under him. I was was suffocating! Bill got the message and rolled off. We lay in each others arms kissing gently. "I think that was the best fuck I've ever had," Bill whispered in my ear. "Thank you."

"And thank you for being so considerate. I loved every minute of making love with you. And your cock is so big!"

It was getting to be mid morning. Bill got up and looked around for his clothes. "I better get back to the convention," he said. "I've actually got work to do."

"I think I'll hang back and have a shower and get back into my boy clothes."

Bill bent down to kiss me again. "You look beautiful even in your boy clothes. Now that I know your secret I'll get a hard-on every time I see you!"

"Well I hope you don't have to walk around the convention with a huge boner! That could be embarrassing. But if you need relief I'll give you a blowjob right away - don't worry!"

I walked Bill to the door. I was disheveled with my lipstick and hair a mess and my babydoll stuck to my body with Bill's sweat. I could feel his cum running down my legs and onto my stockings.

He held me and kissed me at the door. "I hope to see you again this weekend, sexy!"

"I'd love that, as long as it's ok with James."

"Oh, James will be fine with it. I can't wait to tell him what we did this morning! I hope you don't get a spanking!"

I lingered at the door after Bill left. I wondered what other adventures awaited me in Vegas. Today was certainly off to a good start!