Sinnndy Does Vegas

Sid got off of me and I went to my purse to get some KY. It wasn’t really for me, but for Sid, so that penetration would be easier for him. I kissed Sid’s cock, and then placed a generous amount of KY on it. I them put some on his finger, and told him to place it in my tush. I got on my tummy, with a pillow under me, my ass in the air, spreading my cheeks, and Sid placed his finger on my anus. The KY felt cold as his finger entered my asshole. He pushed all the way in, drawing a soft moan from my lips. He slid his finger in and out, it felt great. I said to him, “fuck my ass Sid, fill me up with your big cock, you won’t hurt me. Do what you want to me; I’m your whore. I like it rough baby, you can spank my ass, and pull my hair if you like, I love it.”

Sid placed the head of his cock at my anal opening, and popped the head inside. He was very tentative. “Sid honey”, I said. Fuck me baby, I promise you won’t hurt me, you will be pleasing me as well as yourself”. He was still nervous about putting his cock all the way into my ass, so I helped him out by moving my ass back into him, his cock going balls deep into my rectum. A surprised moan coming from his lips, “Soooo tight”, Sid said. “Yes lover, now treat me like the whore I am, do things to me that you would never have done to Bessie, I’m yours”, I cooed. With that, Sid started fucking my ass, sliding in and out at a nice steady pace, amazed at the new exciting feeling he was experiencing. He lightly spanked my ass. “C’mon stud boy, you can hit me harder than that” I said to him. The next spank was a little harder. “C’mon baby, I’m not your grandchild that you are punishing, give it to me hard, I’m a baaaaad girl, I deserve punishment, spank me, pull my hair, fuck my ass”, I commanded. The next spank was better, “harder please”, swat. “Please, harder” swat, “plllleasssse, harder, I need it soooo baaaaad” I screamed. The next spank hit the mark. “That’s it grampa, spank your little girl, she’s been soooo bad”, I moaned. He was now pumping my ass harder that he had ever fucked his wife, and the spanks to my ass kept coming, swat, swat, swat. “Ohhhhh yessssss grampa, fuck your little girl, spank me, hurt me, fuuuuuuckkkkk me please. Ohhhhh, it hurts soooo gooood” I wailed, and it really did. I brought out emotions in Sid that he never knew existed. He was enjoying the best fuck in his life, if he died right there, it would have been the perfect way to go.

I was rubbing my pussy and clit, fucking my pussy with my fingers, and then working on my clit as Sid pounded my ass. I was nearing my climax; this was as hot for me as it was for him. Sid started moaning,” ohhhhhh dear god, I’m cumming”. With that, he grabbed a handful of my hair with one hand, and hard too, while continuing his hard spanking on my reddening ass. I could feel his cum shooting deep into my asshole as I started cumming myself, screaming, “Ohhhhh yessss Sid, I’m cumming too, you made me cummmm sooo hard, thank you lover, yessssss”. Sid finally stopped filling my ass with his cream, he collapsed on top me, both of us breathing hard, completely satisfied. Sid rolled off of me; his cock popping put of my ass, onto his back. I place my tongue into his open, waiting mouth, and we kissed like teenagers on our first date. I then kissed my way down his body, sucking his nipples, nibbling my way down the hairy trail to his soft cock. I licked the mixed juices of both of our cum, and my ass off of his cock. I love the mixture of tastes, it was yummy.

I started licking his head, sucking on it, licking up and down on all sides of his surprisingly hardening shaft. He was completely erect again, and I started to devour his cock. I knew we didn’t have a lot of time, so I started bobbing my head up and down on his cock, sucking and licking his shaft, stroking his shaft with one hand, tickling his balls with my other hand. He placed his hand on top of my head, forcing my mouth all the way on his cock, swallowing him whole, and then my mouth went back up and down on his cock at a rapid pace, my hand gripping his cock firmly. His breathing was rapid again, “ohhh myyy god sinnndy, I’m cumming again” he wailed. He pushed my head all the way down on his cock, and started filling my throat with his tasty cum. He tasted so good as I sucked him dry, swallowing it all. I moved up and gave him a passionate loving kiss. I told him that he was one of the best fucks I had ever had, and I wasn’t lying. I felt good about myself, helping this lonely kind man performing what had to be a big fantasy of his, anally fucking a hot young babe like myself.

I would have done it for free, and told him it was no charge, but he wouldn’t hear of it. He told me he was quite well to do, that he sold his business a couple of years ago, and was retired and more than comfortable. He gave me the agreed upon $100, and tipped me a $50. He said that he wasn’t trying to judge me, but that I was a sweet young lady, and that I should try to find a different line of work. I confessed to him, that I was not a hooker, and that my boyfriend was fulfilling a fantasy of mine. He said he was glad to hear that, and that I had a very special talent. He asked if he could see me again before I left, and I promised him that it would be my pleasure, but that the next time, there would be no exchange of money, and that I loved having sex with him.

There was a knock on the door, it had to be Billy. I gave Sid a kiss on the lips, and promised him that I would call him later for our next rendezvous. Billy was at the door, and asked me how it went. I gave him a big kiss, and jumped into his arms, wrapping my arms around his neck, and my legs around his waist. He said, ”hey baby, not now, you have other clients to get to”. So I released my grip on him, and he gave me the next room number to go to.

At the Bellagio, there are different elevators, which take you to separate groups of floors. I was on the 12th floor at the time. So I had to take an elevator all the way down, and then board a new elevator taking me to the 5th floor. I walked up to the room, and knocked on the door. A man answered the door, he was a big Texan, cowboy hat and all. He was a nice looking man, about 6-4, a lean proportionate body, with a hard lean face, in his early 50’s. The kind of man you would see on the TV soap Dallas. He owned a huge ranch in some small town in Texas, Rio or Rancho something. He was married, and his wife was in the room with him. She was younger than he was, about 40 years old, with long curly red head, very beautiful. She reminded me of Raquel Welch, very curvaceous, with big round breasts, I think they were paid for, but it didn’t matter to me. She also had a big round sexy looking ass. He was wearing a suit, with one of those string like southwestern ties, and snake skin boots. She was wearing a black teddy, her breasts flowing out of the top of it. She was sexy looking and I was wet with anticipation

I asked to use the phone to call Billy, and told him that I arrived, and hung up. I was wondering what the two of them hand in mind for me. It didn’t take long to find out, Sy spoke up. “My wife and I have a fantasy, she has wanted to try making love to another woman, and its always been a fantasy of mine to watch her, and maybe join in”, he said in a deep Texan accent. “You are both of ours type of woman, pretty, young and petite. Your boss told us that you are very experienced in having sex with both men and women, but you look so young, how is that possible?” He asked. “So, I briefly told him that I had been sexually active since I was 14, that I am 18 now, and lived with my female lover. Sy was more than satisfied with my explanation.

I took my dress off, turning around so the two of them could check out my hot young body. Sy took a seat in a chair and I walked over to Shelley. She was a lot taller than I was, I’m only 5-3, and she was about 5-9. I ran my hand gently on her cheek, and then ran my fingers through her hair. She lowered her face to mine and our lips met in a gentle kiss, our mouths opening as I snaked my tongue into her waiting mouth. It was a romantic, sexy kiss, and our tongues moving slowly in each other’s mouths, mine controlling hers. She was physically bigger than I was, and I like to be submissive in bed, but I started taking charge.

I took her by the hand, led her to the bed, helping her off with the teddy, her breasts popping out, man they big and firm. I took a nipple into my mouth, sucking and licking it, nipping it lightly with my mouth, while caressing her other breast with my other hand. They were so big and firm, I was jealous. I could have sucked and licked them all night, but I knew there was a time limit, so I pushed her gently onto the bed sideways, it was a king sized bed, so we had no problem laying this way on the bed. I figure that if Sy wanted to join in, he could just walk to whatever side of the bed he wanted to. She was a lovely looking woman who took great care of her body. You would never think she was 40, she was sooo hot. I started by kissing and licking her inner thigh, my tongue licking every nook and cranny. I could smell the excitement I was causing by the aroma from her pussy. I licked my way over to her knees, licking around them, and licking the back of them. I licked my way down to her thighs; planting loving kisses and licks all over. I started rubbing her feet, getting her ready for what was next, testing to see if she was ticklish there, which she didn’t seem to be.

I glanced back at Sy, he was still sitting there in his suit, but he had his cock in his hand, and he was stroking it. From the quick look I gave him, it looked like a pretty long cock, but I wasn’t really sure. I was now licking the top of her feet, kissing them, caressing the soles with my hands, licking around her ankles, and over towards her toes. Her toenails were painted; she had lovely ladylike feet. That’s not true with some men and women. Some people don’t take care of their feet, they have foot odor and long unkempt nails, but Shelley obviously enjoyed pedicures, she had great feet. I started licking her toes, darting my tongue between them, licking around her toenails. I then drew a deep moan from her, when I slid her big toe into my mouth, and started sucking it and licking it like it was a small cock. She started moving her legs around as I fought to keep her toe in my mouth. She bent down, and gently pulled my hair, leading me towards her wet dripping pussy. She had a full bush, but it was neatly trimmed. I usually start out slowly, but this time I just buried my tongue in her snatch, licking wildly all over, avoiding contact with her clitoris. I reached under her with both hands, and firmly grasped her ass, it felt so fine in my hands, and it was full like her breasts. She was pushing on my head now, as I licked and sucked on her pussy lips.

I removed one hand from her ass, and slid two fingers easily into her waiting pussy. I started fucking her with my fingers as I sucked on her pussy. She pushed harder on my head, moaning in her southwestern accent, “yessss, ohhh yessss darlin, lick my pussy”. I then lightly touched her clit with the tip of my tongue, and she shuddered and jumped. I then started licking around her clit, barely touching it; her hand went back on my head, pushing me closer to her. I decided that it was time for my attack, and I went to work on her, my tongue making direct contact firmly with her clit, licking it up and down. She now had both hands on my head, and her legs were moving all around the bed. She was moving her head back and forth, screaming, ”yessss, ohhhh yessss”. I was really pressing hard on her clit with my tongue, my fingers sliding in and out of her pussy. She was really screaming now, and I removed my fingers from her pussy, and slid one right into her asshole. She was silent for a second, then screamed, “ohhhhhhh godddd, I’m cumming, I’m cumming, Ohhhhh”. Her hands were really pushing hard on my head, as I lapped her tasty juices flowing from her pussy. “Ohhhhh my godddd, ohhhh godddd, thank you”, she moaned. She relaxed the grip on my head, and I moved up on her body, and gave her a deep kiss, letting her taste herself on my tongue. “Mmmmmmm”, she said, and placed her tongue back into my mouth.

I laid my head on her breasts, and she stroked my hair. She told me that Sy had tried to get her off by eating her pussy, but that she just couldn’t have an orgasm that way, and that was the first time she had one from oral sex, which brought a big smile on my face. She then told me she wanted to taste me. So I got up, placed my legs over her head and lowered my bare pussy to her face. She started licking my pussy lips; she had paid attention to the way I had pleased her. I looked at Sy; he was now completely naked. He had a nice body for a man who probably did not work out. He also had a nice long 9” cock staring me in the face. I took it into my hand, and led it to my mouth.

Shelley was really enjoying her first taste of pussy, and she was doing a great job, sucking my pussy, and fucking it with two fingers, completely ignoring my clit like I had done to her. Sy’s was sliding half his cock in and out of my mouth; I clamped my lips around his rod making it a nice tight fit for him. I had one hand on his balls and two fingers from my other hand probing Shelley’s wet box. I removed my hand from his balls, and pulled his cock out of my mouth, I told Sy, “Don’t be so gentle with me, I can take your cock deep into my throat, remember, I’m your whore for an hour, use me as you would like to”.

With that, I opened my mouth again, and Sy slid the length deep in my relaxed open throat, balls deep, a loud sigh escaping from his mouth. He then started fucking my face, with his hands behind my head, pumping into me like my mouth was a pussy. He didn’t last too long, grunted, and deposited a creamy load into my mouth, I licked him clean, and continued to lick and suck on his cock.

Shelley was now paying attention to my clit, flicking it teasingly with just the tip of her tongue. Sy removed his cock from my mouth, but I continued stroking it gently, and he quickly got hard again. Shelley was really a fast learner, she was really working on my clit now, licking it side to side, and I was grinding my pussy into her face. Sy had walked around to the other side of the bed, to watch his hot sexy wife lick the pussy of the young hooker they had hired. I lowered my face to her pussy, and started licking her all over, sucking on her pussy, licking and sucking her clit. I felt a tongue licking my asshole, and I started moaning loudly, pushing my ass back into Sy’s face. What a feeling, two tongues licking me in my most private of private areas. I then felt Sy’s tongue move away, but didn’t have to wait too long, as I felt the head of the cock work its way into my asshole with a pop, "ohhhhhhhhh”, I moaned. Sy didn’t waste much time, sliding his long tool deep into my bowels, leaving it buried deep inside of me. With a tongue working my clit, a long dick deep in my ass, I thought to myself that I should be paying them. I knew it was Shelley’s first taste of pussy, but I later found out that Shelley was petrified to try anal sex, and Billy had told Sy that it was my favorite position.

Sy started pumping into my ass now, I could feel his big balls smacking into me, as his wife hungrily licked my pussy and clit, driving me closer to climax. I felt one of Sy’s big hands smacking my ass hard, which did it for me, “I screamed ohhhh yessss, harder please”, and started to cum, as Sy spanked my ass, and then started to fill my ass with his warm load. Shelley was lapping at my juices, savoring the new flavor she was tasting. It was one hot sex session. Sy pulled his cock from my ass, and Shelley grabbed it, shoving it into her mouth, tasting his cum and my ass, sucking on it like it was a piece of hard candy, savoring more new flavors, and loving it.

I cleaned up a little; I had a couple of minutes left in the hour. Sy handed me the agreed upon money, I didn’t even look at it. I didn’t care how much or little it was, I just placed it in my purse. I asked Shelley if she wanted to try something new and exciting, that I would talk her through it. She asked me what I wanted her to try. I told her to her on her tummy, with her ass in the air, she had a beautiful ass. I wished that I had more time to give her the reaming she deserved, but I was low on time. With one hand, I started stroking Sy’s cock, and I then started licking her asshole, and just buried my tongue deep inside. Moving it around, savoring the musky smell of her beautiful round ass. I continued to stroke Sy’s cock, and pulled my tongue out, her ass was lubed with my saliva, but I reached into my purse for the KY, put some on my finger. I told her to relax, to concentrate on opening her sphincter, that she would feel a little pain, but that it would subside. “Relax now baby, just relax”, I whispered into her ear. The tip of my finger slid easily into her ass, and a slightly painful “ohhhh”, escaped from her lips. “Relax Shelley, open up for me, I promise you will love this, and your sex life will change for the better, for both of you.

I was now knuckle deep, she was still tensing up, but also started to relax, and I slipped another finger inside, and started to swirl them around. I then started to slowly move my fingers in and out of her ass, and she started to push back with her ass. I placed some KY on Sy’s now hard cock, he was really excited. I took the head of his cock, and placed it at her anal passageway. Slow and easy I told him, let her get used to it first. He slowly pushed the head of his cock in, and it went in with a pop. “Ohhhhhhh, that hurts, but it hurts good”, Shelley moaned. Sy now started to ease his cock in deeper, and like a pro, Shelley pushed her ass back into him, and his cock was all the way in. He started to pump slowly now, and Shelley was telling him, “yessss honey, fuck my ass, give it to me, ohhhhhhh yes, I love it”. There was a knock on the door, I kissed Shelley and Sy goodbye, and they both thanked me for opening their eyes to new things.

I opened and closed the door, with big grin on my face. “Having fun, huh?” Billy asked. “Yea, this has been great so far, what’s next”, I replied. “This next one is kind of kinky, but he is harmless, I checked him out pretty good. I will walk you up to the door, and stay there for a while”, Billy told me. “Hmmm”, I wondered aloud.

We got to the door, and I knocked on it. A woman about my height answered, she was wearing a dress, and had a lot of makeup on, she was also wearing a wig. I thought to myself, this is weird, Billy said HE was harmless. Then in hit me, this woman was a man in drag. He was completely shaved, no hair on his face, arms and legs. He was a not bad looking woman, he sure had me fooled. He even spoke in a high woman’s voice. He told me his name was Sandy, and that he wanted me to do some nasty things to him. He told me he was a bad girl, and that he/she should be punished. This was new territory for me, I am submissive in bed, and while I sometimes take control, I never think of myself as a dominant, I thought to myself, this should be interesting.

“So, you little slut, you have been bad have you? Well, I will show you what happens to bad little sluts like yourself, come here slut”, I commanded. “Yes”, he said meekly. “Yes what”, I said sternly. “Yes Mistress”, he said. “That’s better you little whore”, I said. I sat on the bed, and Sandy came over to me. I grabbed the back of his head firmly, and forcefully pushed him down, so his tummy was on my lap. I lifted his dress, lowered his panties, and said to him, “this is what happens to bad little sluts. I want you to count for me, if you lose count, I will start over again, and hit you harder, do you understand?” I commanded. “Yes Mistress, please don’t hurt me too badly”, he whined. “Silence”, I shouted, “your ass is mine, I will decide how hard I will hit you, and you will thank me after counting each swat”.