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Training Oprah Category: Roleplay Stories
I have been a personal trainer to the stars for a little while now. I've always been in great shape and I know a lot of people in Hollywood, so I started my own fitness business. I have quite a list of clients already and I'm gaining more all the time. My newest client is the Queen of Talk Shows herself, Oprah Winfrey. I've always had a crush on her, those thick, full lips and of course those gorgeous, huge breasts always drive me wild. I was "turned on" to her by her best friend, Gayle King, who is another of my clients. We have been working together for a couple of weeks and have become very close. I've worked on her body, in more ways than one. I should mention, I'm very much a ladies man and I've fucked all of my female clients. Gayle is quite talented in the fucking department. She and I have become good friends as well. I really enjoy my job.
I arrived at Oprah's house for our private workout. Gayle answered the door and greeted me, smiling. She told me Oprah was in the exercise room down the hall. We kissed goodbye, as she had to leave, but she hugged me and said "have fun sexy man." She smirked and kissed my cheek as she left.
I walked down the hall to Oprah's exercise room and when I got there, I smiled. Oprah was already stretching, and looking so amazingly sexy doing it. She was wearing a grey sports bra that barely contained her huge, perfect, ebony tits and very tight, blue spandex pants. She had on white and black tennis shoes, a grey headband and grey wristbands.
"Hello Oprah, it's a pleasure to meet you ma'am. I'm Dick. I'm here to work on that body of yours." We laughed at my introduction.
"It's a pleasure to meet you Dick, and please, no need to call me ma'am. I've heard a lot about you, especially from Gayle. She really likes you and she swears by you. I'm sure you will work my body really well." We laughed again, at the work her body stuff. I was wondering how much Gayle had told her about me.
"I really like Gayle as well. She's very nice and very easy to work with. She's one of my favorite clients. I'm very excited to work with you Oprah, I've had a big crush on you for a long time."
"That's very sweet Dick, a handsome guy like you, having a big crush on little old me, is really flattering." She walked over to me, hugged me and kissed me on the cheek. She smiled and touched my arm, holding it for several seconds, before starting to stretch again.
I got ready and went over to Oprah to make sure she stretched correctly. She was touching her toes and when she bent over, I could tell she was wearing a black thong. I was behind her, making sure she slightly bent her knees when she bent down. I had my hands on her thick hips, slowly moving them down the sides of her legs, as I carefully watched her form. I got her to stand up straight and raise her arms over her head. I held them in place and got her to spread her legs, then I slowly bent her backwards towards me. My face was touching hers. I could smell her perfume, she smelled very good. She has good taste in perfume, as well as everything she puts on. I straightened her back up and took her arms, as I slowly pulled her outstretched arms back towards me.
This position made her huge breasts push forward. I couldn't help but stare. Oprah has truly spectacular breasts, all natural wonders, and I took in the view. I slowly moved my hands across her arms, telling her that posture, while stretching, is very important. "I can feel my muscles stretching Dick. Your hands are very talented." Oprah made me smile, and I kept softly moving my hands back and forth across her arms, my crotch softly brushing against her thick ass. I could swear she wiggled her ass slightly on my crotch, but I kept going with our workout.
I got her to bend over again as I slowly pulled her arms back. My crotch was now fully rubbing against her thick ass. I was half hard in my pants, and the fact that I wasn't wearing underwear made the contact between us more noticeable. I tried to ignore her great ass rubbing on my cock and I continued stretching Oprah. I moved her around in different directions and made subtle contact with her body as she stretched.
I was now holding Oprah's feet down, as she was doing crunches and this was even worse for my jerking cock. Every time Oprah came up, I could see her beautiful cleavage and it was mesmerizing me and my 10 inch cock. She would even pause so I could get a good look, or at least I felt she did. I couldn't determine if she was really teasing me or not. She came up the last time and paused for sure, my cock was focused on the sight. It twitched and started to get rock hard in my thin sweat pants. Oprah noticed this time I know, as she looked right at it and smiled. She looked at her cleavage and back at me, winking at me.
I rubbed my hard cock on her shoes slightly, it was throbbing for her. She didn't say anything and she adjusted her sports bra, so I could watch her huge tits jiggle in it. She asked if I could rub her back a little since it had become sore. I moved behind her and started softly rubbing up and down it. I knew she was teasing me now, as she pushed out her chest and I rubbed her back all over. I got to her sides and worked my fingers down deep to get rid of the kinks. "You know Dick, Gayle told me about the "workouts" you two have. She told me that you always loosen her up and make her body feel so good from head to toe." Oprah was smiling and talking in a very sexy voice. "You said you have had a big crush on me, so do you ever fantasize about me and my body?"
I assured her I did very often. She took my hands from her sides and placed them on her huge ebony tits. She squeezed my hands on her tits and said, "well, you have me in your hands now, so here's your chance."
I immediately fondled those amazing, huge tits. I squeezed them hard and shook them, softly then harder. Oprah has such big, soft tits, they felt amazing, as I played with them. She moaned and squirmed, pulling them out of the top of her sports bra and let the bra support them as they hung out. I licked Oprah's neck slowly as I pulled her large, puffy nipples as far as they would go and shook them hard.
"Mmmmmmmmm baby, that feels so good. Play with Oprah's big tits baby. I love it." Oprah said as she moaned from my relentless breast play. I squeezed them and slapped them, pulling those big nipples and shaking them harder. I was in heaven, groping her spectacular breasts.
I kissed her deeply, tasting those dark, full lips. I licked her tongue, as I kissed her. I continued my tit groping as well. Rubbing the tips of her thick, erect nipples with my thumbs. I sucked her tongue, kissing her deep, basking in the taste and feel of her luscious, thick lips. She wasn't wearing any makeup and it didn't matter. She was gorgeous to me and she turned me on so very much, driving my lust for her through the roof. Oprah was my woman at that moment, as I made out with her, and the thought of it was making my cock so insanely hard.
"Dick, I love your hands all over me. I love your lips on mine. Please let me have that big cock, I need it so very bad baby." Oprah asked and Oprah received. I pulled my raging, hard cock out of my pants and pulled them off quickly.
I stood up next to Oprah's head and turned her face to mine. I slid my huge cock in her mouth and watched as she gobbled it up. She sucked the thick head and worked her tongue all over it. She sucked inch by inch, licking as she went, all the way down my 10 inches of white cock. She squeezed my balls softly and rubbed them as she sucked me, all the way up and down. All 10 thick inches entering her mouth and throat as she went. "Suck that big, white cock baby. It feels so fucking good. Have you ever had a white cock in that mouth before baby?" I asked.
"Yes, I used to let an intern tit fuck me during filming of my talk show, and I would suck his smaller cock, as it popped out of my big tits. It wasn't nearly as big as yours though Dick." Oprah told me, as she played with my balls and kissed my rock hard cock all over, with those perfect lips.
She sucked my cock again. She deep throated me so easily. I moved around in front of her and took my cock out of her mouth. She kissed the head slowly and it looked so fucking sexy. I slapped her huge tits with my huge cock, smacking her thick nipples, then the rest of her tits with my cock. I pulled her sweatbands off of her wrists, and put them on her huge tits, like a tit ring for each one. I put my hard cock between her tits and she wrapped them around my cock. I fucked those amazing tits, pulling and shaking her big nipples as I did.
I looked right at her as I fucked her tits, squeezing them as I fucked them. She sucked my cock head as it popped out of her tit tunnel, licking it too and smiling a big smile as she did. I pushed up into her mouth, letting her suck it again. She sucked it fast, her mouth working overtime on my big cock. "Cum in my mouth Dick, I need your protein shake baby." I drilled her mouth fast, as I squeezed those perfect tits. They are G cups, I saw her sports bra. I fucked her tits and mouth harder, thrusting all the way in her sucking mouth as she played with my big balls, coaxing my protein shake up and out of them.
"Here it fucking cums baby!" I declared as I shot jolt after thick jolt of my creamy, protein shake deep into her sucking mouth. She rubbed those big tits all over my cock as I came. It felt so damn good, I just kept cumming. I filled her mouth three times and she hungrily swallowed every last drop. She sucked me clean and slid her finger up my ass to tickle my prostate. It caused me to have an urge, as I pulled out of her mouth and started pissing all over her face and tits. Oprah was shocked initially, but she quickly put my cock in her mouth, and swallowed my piss right down her thirsty throat. I pissed a gallon down her throat. She turned me on so fucking much. I just tit fucked my dream woman, and now I'm pissing down her throat. I smiled so fucking big, as I watched the action.
I pulled out of her mouth and quickly went down to her neatly trimmed, full pussy. I sucked her large, throbbing clit hard, softly biting it. I sucked it as hard as possible, and let it pop back into place, as I released it from my sucking mouth. I twisted my tongue all the way up her dark pussy, and licked her out fast as I tongue fucked her pussy. I thrust my tongue in and out of her full pussy quickly, licking her out even quicker. My tongue darting all over her pussy walls, tasting every inch, dragging my tongue across her walls.
Oprah was squirming and moaning like crazy as I ate her out. "Dick, I'm gonna CUMMMMMMMMM!!". She yelled, as she squirted all over my tongue. I licked it all up and took my still hard cock and shoved it all the way up her very wet pussy. I put her thick legs on my shoulders, squeezed her huge, wet tits and pummeled her super wet pussy. My cock thrusting so fast up her wet pussy, as I looked right at her. My hardcore lust for her, driving me wild. I fucked her faster and harder all the way up her pussy. Every inch pounding that pussy good. "YESSSSSSSSSSSSS, FUCK MEEEEEEEEEEEEEEE!!" Oprah screamed out in sexual euphoria. She squirted again, all over my cock this time. I pulled out and watched the rest of her juices shoot out of her thick pussy. I smacked her clit and shoved back up her pussy.
I fucked her as hard and fast as I could, as she screamed out her approval. I reached down and started fingering her tight ass. I wanted it, so I got it ready. I fingered her ass fast, three fingers in and out of that tight hole. I pulled out of her pussy and stood up, telling Oprah to "fucking spit on my cock bitch, I wanna pound that black ass." She did, a big wad on my cock. I told her to open her mouth and she did. I spit in her mouth telling her to swallow it. She happily did.
I flipped her over on her hands and knees. I got behind her ass and SHOVED my aching, hard as steel, cock all the fucking way up her big, thick, tight ass. I smacked her ass hard as I fucked it so fucking fast. "YESSSSSSSSSSSSS BABY, FUCK THAT BIG FUCKING ASS WHITEBOY, TAKE MY BLACK ASS MOTHERFUCKER!! YESSSSSSSSSSSSS!! Oprah screamed at me, smiling lustfully, as she looked back at me.
I grabbed her ponytail and railed her ass so damn hard. I smacked it hard, as I fucked her now, less tight ass, at a supersonic speed. My huge white cock destroyed that thick, black ass in the most pleasurable way possible. Her huge, hanging tits flopped furiously as I pummeled her ass. I slapped them hard and squeezed them as I fucked her ass faster. I finally exploded my cum up her ass. Thick ropes of creamy nut filling her ass as she screamed in pleasure. I smacked her thick ass again as I felt the urge to pee again. I said fuck it to myself and I pissed in her ass. It caught Oprah by surprise, but she liked it. "Fill my ass with your piss Dick, FUCKING PISS ALL IN IT BABY!!" She yelled.
My piss joined my thick cum and cock in her ass, overflowing her ass. As I pulled my very happy cock out of her ass, my cum and piss poured out. I stood up and pulled her face to my cock. I slowly fucked her face, letting her taste the flavor of all of it. She sucked my cock eagerly, looking up at me with those beautiful black eyes. I reached down and slapped and squeezed the tits of my dreams, as she sucked me.
I wanted to cum again so I grabbed her ponytail and fucked her mouth hard and fast. Her tongue was licking the underside of my cock as I pounded her mouth. She moaned and let her saliva fall out of her mouth as she sucked me. I slapped her sexy face softly and pummeled her gorgeous mouth. I felt the urge to cum, so I pulled out and told her to jack me off into her mouth. She opened her mouth wide, stuck out her long tongue, and jacked my cock fast with both hands. I came in her open mouth. She licked it up as it came out, and let it slide off of her tongue onto her huge tits. She sucked all of my cum out of my cock, smiling at me as she did. She sucked my cock clean and then picked her tits up to her mouth. She looked at me, with a devilish grin, and licked all of the cum and piss off of her tits. She let it hang off of her tongue before she slurped it up into her hungry mouth. She licked those huge tits clean, smacking her lips in approval of the taste.
We showered and fucked in the shower. We ate and then fucked again. We never did finish our workout, but we got around to it the next day. We have been fucking everyday since then. Oprah loves having me, and my cock, around and we, love being there for her. She is such a fun workout and fuck partner. Her and those tits of my dreams.
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