Sinnndy Does Vegas Ch. 3

With that, 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, and 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. He 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."

Smack, I hit him pretty hard. "One, thank You Mistress, may I have another?" He said obediently. "Very good slave," I happily replied. The second spank hit his other cheek just as hard. "Two, thank You Mistress, may I have another?" And so it went on, until he counted 20. I stopped because I thought he had had enough, his ass was pretty red, and my hand was getting sore. I forcefully pushed him off my lap, and onto the ground. "I'm not done with you yet slut," I sneered. I had this guy figured out, he wanted to be humiliated, and I was really enjoying exploring this new side of mine. I took him by the ear, and led him into the bathroom. "Off with your clothes slut," I commanded. Off they went. He was naked now, sporting a cute 5" erection, he was even clean shaven in his pubic area. "Into the tub," I commanded. He was really into what he knew was going to happen next. I lifted my dress up, and squatted just inches above his face, letting a stream of urine fall into his open mouth. He gleefully swallowed all my pee. It felt so good, standing there as I relieved myself, knowing that this man under me would allow me to do whatever I said. For the first time in my life, I was the one in complete power, and it felt really good.

"Clean me slut," I barked out. He happily started lapping at my pussy, his tongue licking all over me, savoring the combinations coming from my pussy. He ate pussy like the woman he wanted to be. Licking my clit up and down, fingers sliding into my wet pussy. Within a minute, I climaxed heavily, as he licked and swallowed the juices flowing from my pussy.

"You have done well slave. You will be rewarded," I informed him. I helped him out of the tub, and led him by his cock into to bedroom, and onto the bed. I noticed a 10" strap-on located on his nightstand. I have had lots of experience with strap-ons, mostly with Mia, my girlfriend, and a couple of times Billy let me fuck him. This was not a cheap toy, and with a dildo this big, I knew I was going to do some damage to his ass, but I'm sure he would be ready for it.

I stepped into the strap, and tightened the belt. I put some KY on my finger, and slid it into his asshole, probing him gently, sliding it in and out. I put another finger in, slid them in and out. He was ready for the real thing, so I lubed up my plastic cock, and popped the head into his open and ready ass. I left it there for a little while, and he whined, "ohhhh, please fuck me Mistress, give it to me, fuck my ass good, please."

I grabbed his hips, and buried my cock all the way inside if his ass. He let out a loud "ohhhhhhh." I kept my hands on his hips, and started to fuck him hard. I was fucking him like I liked to be fucked, hard and deep. I slapped his ass hard, "Ohhhhh yessssss," he moaned, so I slapped him again and again, and he met my every deep thrust by pushing his ass back into me. I pulled my cock out of him, and crawled onto my back. "Mount me slut," I commanded him. He placed my cock at his anal opening, and slid all the way down, grinding his ass into me. "Ride me slut," I said, and he bounced up and down on my hard plastic cock, taking the whole 10" deep into his rectum every time he went down.

I started stroking his erect cock, with a firm grip, tickling his balls with my other hand. He was really riding me, bouncing up and down, his ass slamming into my body, my cock deep inside his, while I stroked his cock, and played with his balls. "Mistress, I am so close, may I cum? He begged. "You will not cum until I tell you to, you are here to serve me, you are mine" I barked back. He continued to ride me, I could see the pain of trying to hold off his orgasm, he was trying so hard to please his Mistress. I said, "you may cum now slut," and as the words left my mouth, he started spewing his cream all over my breasts, for a little guy, he shot a lot of cum. I said, "clean me slave," and he proceeded to lick his cum off my breasts, sucking my nipples and licking my breasts. It was quite a scene; he even still had his wig on.

We sat on the bed, and talked for a little while. His name was Sidney; he was an accountant from Columbus, here for a convention. He was 42, not a bad looking man, but he also had make-up on. He was married with three kids. He told me his wife would never understand his need to be treated like a slut, so when Billy approached him, and told him about me, he got really excited. This was the first time he ever tried this, he had never cheated on his wife in the 20 years they were married, but he just had to do this at least once. He told me that he liked to masturbate with a dildo in his ass, that while not gay, he loved the feeling, and wondered what it would be like to feel a cock, even a plastic one fucking his ass. He thanked me for fulfilling his fantasy, and asked is there was anything he could do for me.

I was flattered; I asked him if his wife let him fuck her in the ass. He chuckled, and told me that they tried it when they first started dating, but when he stuck the head of his cock in her ass, she tensed up, screamed, and told him to take it out. What a bitch I thought to myself, his cock wasn't big or thick either, it couldn't have hurt that much. I put my head on his pillow, and led his cock into my mouth. "Fuck my face Sidney, please," it was my turn to beg. Sidney slid his cock into my mouth, it was strange to have a cock in my mouth, and not be gagging. He got hard fast, and started sliding in and out of my mouth, pumping his hips into me. I pushed him back, and said, "now fuck my ass stud, give it to me." A big smile was on his face. He spread my legs and placed them on his shoulders, and slid his cock into my ass. It felt nice not having a monster tool splitting me in half for a change. He started pumping me as hard as he could. His eyes were closed. He had such a determined look on his face. I wrapped my arms around his neck, and my legs clamped tightly onto his back, bringing him close to me, as he pounded into my ass. He was a good fuck, and he was enjoying it so much, as was I.

He was so excited, that he didn't last too long, I felt cock and body spasm, filling my ass with his cum. He collapsed on top of me, his cock still in my ass. He stayed there for a couple of minutes, and we started kissing, and I lightly clawed at his back and his ass.

I told him that I had to go. I went into the bathroom to tidy up, got myself together, and as I came out, heard the knock on the door. I gave Sydney a peck on the lips, he thanked me, and I wished him good luck, and went out the door, into Billy's arms. "So, are you up for one more client?" He asked. I was tired and sore, but I figured, well, its just one more, and I think I have helped some people out tonight. "Sure, what's next?" I asked. There's a young guy here, his brother is 21, and is a virgin. He saw you in the casino, and couldn't stop talking about you. His brother figured that for a birthday present, that he would hire you, and then maybe join in after it. I told him to take his time, and that he would be charge hourly, and only up to two hours because how late it will be. Sure you're up for it? He again asked. "Well, haven't popped a cherry in a long time, why not," I replied. So into the elevator shuffle I went.

I knocked on the door, it was answered by an attractive young guy, about 24, 5-10, thin, short brown hair, he told me his name was Brett. His brother, the birthday boy, was Tommy. He looked like his brother, but was about twenty pounds over weight, all of it, in his gut. "What is she doing here?" Tommy asked in surprise. "She's your birthday present from me and the guys," Brett responded. I looked around the room, what did he mean, "the guys?" I wondered. "What do you mean by birthday present? Tommy asked incredulously. "She's yours to do as you please. You told me how hot she is. She will be your first fuck. Enjoy little brother," Brett announced with pride. "Are you serious? You're not fucking with me, please tell me you're not," Tommy said. "Hey, you better quit wasting time with stupid questions, the clock is ticking, when you are done with her, I want to test her out too," said Brett. I called Billy to let him know I arrived.

I walked over to Tommy, and thrust my tongue into his mouth. He kissed back, but obviously wasn't sure of himself. I would have to initiate everything with this one. "Happy birthday stud. You can do everything to me, that you have ever wanted to try, and been waiting to try for years." I quickly stepped out of my dress, did a turn, showing off my body. I helped Tommy off with his shirt, his pants and undies. He did not have the kind of body I look for in a man, but at least he wasn't grossly obese,and seemed like a really decent guy. His cock was standing straight up; it was about 6" long, a nice average sized cock. I lightly grabbed it, he almost jumped out of his skin, and I was the first person other than him, to touch his cock. I licked the head of his cock, and asked him, "does that feel good Tommy? Do you want me to continue?"

"Yes, please do, it feels soooo good." I started teasing his peehole, stroking his shaft, he was squirming now, his eyes shut tight, with a big smile on his face. I then started sucking his cock, stroking him with a firm grip, deep throating him, and raising off of him, and then all the way back down. Being his first blowjob and being so excited, he started grunting, and came into my throat quickly. He had the biggest smile on his face, and his brother gave him a thumbs up.

I had Tommy lay on the bed on his back. I started stroking his cock again, while my tongue did its magic on his balls. Licking them and then sucking on them. Tommy was squirming under me, moaning "ohhh, that feels so good. I can't believe this is happening, ohhhh god." He was now hard again, and I was pretty wet, it's not every day that I get to break in a virgin. I placed my pussy over his cock, and slowly impaled myself onto his cock, stopping when I reached bottom, grinding my ass into him. I took his hands, and led them to breasts. I started moving up and down on him, taking him all the way down, staying for a second, and slowly going back up. He was groping my breasts and pinching my nipples. I started to buck up and down hard, my ass cheeks slamming into his thighs. I rode that way until I got tired, it was late, and my pussy and ass were now really sore.

There was no way he was going to cum in this position. A lot of guys have trouble cumming when they are on their backs. They need to be able to move their hips to cum. I got off of him, and got on my back. He got on top of me, and I steered his cock into my pussy. He was very awkward, he would pump a couple of times, and then his cock would slip out. I felt bad for him, so I locked my legs around his waste, and said, "relax Tommy, my pussy feels good, doesn't it? Just enjoy your first time; don't worry about pleasing me, or being embarrassed. You are giving me a great fucking, your cock is soooo big." (So, lied). By locking my legs around him, it brought him closer to me, and his cock didn't fall out again. He started to relax and enjoy himself, and he started to fuck me good and hard, finding a nice rhythm.

I saw that look on his face that told me that he would not last much longer. "Cum for me stud, fill me up with your cum, please Tommy, I need your cum soooo bad. So I stuck my finger in my mouth, licked it, and slid it into his asshole. His eyes opened wide, and he then grunted, and started filling my pussy with his cum. He had a big smile on his face, and I gave him a big kiss. Good job, I told him.

I heard a couple of guys saying "atta boy Tommy,"

"way to give it to the bitch"; "you are now a man Tommy." I looked up. The door connecting two rooms was open, and there were about ten young guys inside, giving each other high fives, and sucking down beer. I know Billy likes to surprise me, but he knew I was tired and sore, he wouldn't do this to me, would he? To test the situation I said to Brett, "hey, no one said anything about a group of guys."

"Change of plans. We have so much time left to kill, hope you are up for it" Brett said nonchalantly. I was a little nervous now. I love a gangbang as much as the next slut does, but I really wasn't up for this. These guys were strangers, and Brett lied to Billy.

I got up to go for the phone, and Brett pushed me down on the bed. "We paid for two hours of your pussy, and pussy is what we are all going to get." I tried to get up again, and Brett grabbed my arm, and put it behind my back, raising it up high. "Owwwww, you are hurting me," I said. "Don't fight it, and you won't get hurt," Brett replied. He threw me face first on the bed, pulled his pants down, and stuck his cock in my pussy. He grabbed my hips and started fucking me violently. I tried to get away, but he was too strong. A cock was placed in my face, I opened my mouth, and the cock went deep into my throat.

Brett was pulling the back of my hair, and the guy who was fucking my face, held my head with his hands, and slid his cock in and out of my mouth. Tommy said to his brother, "hey Brett, this isn't right, this isn't how I want to remember my first time."

"Shut the fuck up, you got yours, the rest of us are going to get a piece of this slut too" While I wasn't into the way I was tricked into this, part of me was enjoying it.