Intern to the Star

I was looking for a job in my particular field when my cousin who works in the movie industry said she could get me work as a production assistant on a movie for a couple of months. Well that would give me something to add to my resume and kill a couple of months so I went.

I met one of the producers and he was surprised to have a 40 year old guy want the job because usually it was inexperienced kids fresh out of college. But he said he was grateful because he had a particular assignment that suited me. I discovered I would be the production assistant for one of the stars of the film Oprah Winfrey.

It seems the younger set so wanted to impress Oprah in hopes they might get to work for her they didn't pay attention to the rest of the job. But since I wasn't aspiring to climb the entertainment ladder I wouldn't have the same issues. Truth of the matter is I never really watched her show, I've seen her act and I know she's a media giant but not a big fan.

So the first day I was introduced to Oprah and after telling her about myself and telling her I thought I understood the task at hand she told me she thought I'd do fine. For the next few days I made sure of her schedule, got her the revised script pages for the day, let her know when she was needed on set and drove her around the set in golf cart. Oh to be in pictures.

The second week we were on location and staying in a hotel, I was assigned a car so after getting the days schedule from the production staff, driving Oprah from the hotel to the location shoot started my day. After driving her back to the hotel I usually didn't have any responsibilities with her.

On the third day driving back to the hotel Oprah asked if I was busy that evening, I mentioned that some of the crew was meeting at the pool and that was about all I had planned. She asked if I could stop by her suite on my way to the pool. I didn't see that as any problem.

I got there about 7:30 and Oprah invited me in and offered me a drink, which I declined as I figured to wait until after swimming. She was wearing sweat pants and an oversized t-shirt and I had on swim trunks and a Hawaiian shirt. That's when she hits me with the oddest question I could have imagined, "Do you wrestle Jimmy?"

After a few seconds to process that one I said, "Not since high school gym class I don't think."

That didn't phase Oprah who said, "Well that's OK you look like you can handle yourself. Why don't you move that loveseat, chair and table to give us some room."

I know this wasn't in the job description but here's Oprah ready to go to the mats with me. A younger man might have simply fled the room but I actually thought, this could be an adventure. So I moved the furniture and turned to see Oprah had removed her sweats and shirt and was wearing a lycra bodysuit that clung to and accentuated every curve and roll of her wide thick body.

As I removed my shirt it dawned on me that this is actually happening. I'm 40 years old 6 feet tall and 190 pounds and I'm looking at Oprah who is about 20 years older, about 5-6 tall and I'm guessing like 240 pounds because I sure as shit ain't going to be asking her. She's wearing knee pads and is putting on a headband to contain her massive afro.

She then laid out the rules, best of 3 falls, shoulders down 3 count pin or submission, nothing dirty, no punching, just a friendly competitive match. Well as crazy as the situation seemed I wasn't fleeing the room so it was game on.

We circled slowly, I was trying to formulate a plan of attack against a heavier, wider opponent who I had no idea of her skill level at this. Whatever plan I had I reached out as did Oprah and I made a quick move to avoid her and was able to get behind her trapping her left arm in a half nelson and getting my right arm around her waist.

Well we were going at it and at least I was doing something. Oprah countered by thrusting her big butt back at me and bending forward. I took her lead with her bent facing the floor I eased forward ending up off the floor on her back. Oprah has some damn thick legs and was able to hold on a few seconds before staggering a bit and slowly dropping to her knees on the floor.

I seized the opportunity to slip my right arm under hers and lock her down in a full nelson as Oprah was face down flat on the floor as I layed on top of her. With her arms locked up Oprah could only struggle but was unable to counter me in any way. And we did that for a couple of minutes as I didn't think she would submit quite yet while I pondered my next move.

Due to the lycra suit Oprah had on and her struggling under me the next move came in the form of my sweaty body slipping off of her. I slid onto my hip, maintaining the full nelson and Oprah sort of rolled with me ending up likewise on her side between my legs. With one leg under my opponent I wasted no time swinging my other leg over and scissored Oprah's waist locking my ankles in front of her stomach.

Oprah let out a groan, not from any great pain my double hold inflicted but she knew she was in an inescapable position. Rather than quickly ask if she wanted to submit I decided to just hold where I was for and let her see what she did. After a minute or so Oprah began to churn her legs and try to push us around the floor to no avail then after another minute or so I quietly said, "Do you want to concede the fall?"

Oprah sighed and relied, "Yes dammit, you win this one."

I then opened my legs and as Oprah rolled out from between them I let her arms slide free. "Damn you must have been pretty good back in gym class, you took my fat ass to school that time. But I'll come back strong"

We took about a five minute water and air break before starting the second fall. I figured to take a different approach at the start and apparently so did Oprah. She rushed me head down going for my legs but my reflexes kicked in and I managed to side step her move and she crashed onto the loveseat.

As Oprah got to her feet I made my move before she could get oriented. I pushed her shoulders down causing her to tumble to the carpet and I jumped on her back. I managed to get her left arm behind her back in a hammerlock and we paused for a few moments to assess our situations.

Oprah made the move I was hoping for, she started to roll to escape but I was able to rise up slightly to let her and slide off of her back. I was also able to keep her left arm behind her back trapping it under our combined weight, which is considerable. Then pivoting on her slick wrestling outfit I moved across her shoulders, grabbed her right wrist to stretch her arm out for the pin.

I counted slowly thousand 1, thousand 2, thousand 3 and asked Oprah, "Pinned?"

She drew a deep breath and replied, "Fuck yeah, pinned."

I very quickly released my opponent and slid off of her then helped her free her left arm. "You're not injured are you?" I asked.

"Only my competitive pride" Oprah responded. "You whipped my big butt twice and rather quickly, you're a good man Jimmy."

I grabbed the water bottles and went to refill them. What I noticed most of all, besides that I was sweating a lot, was that my cock was plenty hard. I never really gave Oprah much thought before I met her, then I was basically working for her but I guess the close physical contact, that thick soft body, her big fat tits, well padded ass, a boner was the natural reaction.

Handing Oprah her water bottle I sat down on the loveseat and started drinking. Oprah sat down and drank some water then crawled over in front of me and said, "Well Jimmy I neglected to mention the rule about the winner getting a prize."

Then Oprah, on her knees in front of me, peeled her lycra bodysuit down to her waist exposing her massively fat jugs with very wide and erect nipples. She then reached forward to take the waistband of my shorts, pulled them partially down to free my stiff dick and said, "I could feel this was ready but damn you've got something here."

With that Oprah leaned down and took the head of my 8 inch cock in her mouth. My mind went blank for a minute but my dick was into the fine blowjob I was getting from Oprah Winfrey. I regained my senses and looked down to see that big afro bobbing up and down as this mega star swallowed the top six inches of my cock with no doubt she could take it all down her throat.

Figuring it might cause some kind of problem I resisted the urge to grab that fro with both hands and face fuck this woman because she was really going to town sucking my cock. Once Oprah finally deep throated my dick she slowly pulled back and let it slip from between her lips. Then looking up at me with a wide smile said, "I don't want to put you on the spot Jimmy but since you won 2 straight I'm going to give you the option, do you want me to just finish this or would you rather pause here and we can get to the bed so you can fuck me?"

Goddamn I thought, this could be my last day at this job but what the fuck might as well go out with a flourish. I took Oprah by the elbow and had her climb up and sit on my lap and said, "I'm all for pausing and getting to bed."

I took both of her fat jugs in my hands and buried my face in the mass of titflesh. Oprah, put her hands behind my head and said, "I am so glad that was your choice Jimmy now you just rev up that motorboat because I just adore a man who loves the big titties."

After I feasted on those fat knockers for a few minutes I raised my reddened face and said, "Shall we adjourn to the bedroom?"

As she was getting to her feet Oprah said, "Oh let's, if you're as good with that big dick as you are with that mouth I'll get fucked like I'm needing it."

I stood up and we scurried to the bedroom. I easily dropped my shorts and gave Oprah a hand slipping out of her bodysuit, which was no easy task. With no set plan I eased Oprah down on the bed on her back and laid next to her and we hugged and kissed for a few minutes.

Well I'm here I thought to myself so I crawled between Oprah's thick thighs to go down on her. That's when I got the next surprise of the night. I found myself staring at Oprah's neatly trimmed snatch, her pussy hair neatly trimmed into an 'O' just above the slit. I was too stunned to even laugh as I thought, she must pay somebody quite a tidy sum to keep that bush maintained.

But when I realized where I was I dove right in tongue first. I gave it a first class effort, darting my tongue in, kissing and rubbing my 7 o'clock shadow against the insides of her thighs and licking the all around her 'O'.

I was apparently getting the job done because Oprah went from gently opening and closing her cushy soft thighs against the sides of my head to pinching them closed and gently rolling her hips from side to side. Oprah kept that up at a slow steady pace while with my head pretty well set between those thick thighs so I just kept lapping away at her snatch.

Finally I guess she was sufficiently heated up because Oprah spread her legs wide and I took the opportunity to give my ears a break and looked up at her flushed face. She continued to rub her fat jugs with both hands and said, "Jimmy if that big cock is hard grab a condom and climb on, I need to get seriously fucked."

Well I didn't need to be told twice, I got a condom in place and slid right between Oprah's big legs. Holding my cock in my right hand I slipped the head into her pussy.

I took my time slowly pushing my cock in a little and pulling back. Oprah had her eyes closed and was squeezing her fat jugs when she softly said the obvious, "Oh yeah Jimmy you're doing it just remember you've got plenty cushion to be pushin' on."

At that point I slowly eased my cock all the way into Oprah's pussy and just paused to look at her. Oprah got a wicked smile on her face and bracing her feet pushed her hips up at me. I responded by pushing back down onto her and again she pushed her big fat butt off the bed and it was on. With my cock mostly staying all the way in her pussy Oprah would hump her thick body up off the bed and I would push her ass back down into the mattress.

After an extended back and forth I could tell that Oprah's legs were tiring that's when she stayed down and said, "OK Jimmy you were up to that action, now pound that big dick in my pussy, you earned it and I need it."

I was proud of myself whatever it was I did to pass the test and just started pumping my cock into Oprah's pussy as she massaged her fat tits and got off. I could quickly hear my sweaty body slapping against Oprah's equally sweaty body as I drove my cock to the balls into her snatch. To enough Oprah's big butt provided plenty of cushion for me to pound down on and she was getting off on getting fuck good and hard.

When Oprah pinched her soft wide thighs against my sides it was awesome but proved too much for me to be able to hold back for very long so when Oprah held between her legs and rolled her wide hips I paused before shooting my load.

From all the wrestling and breathtaking sex we were both spent and I pulled out and layed on to of Oprah resting my head on her fat tits. I rubbed her sides a Oprah seemed every bit as satisfied as I was. Then I slid up and we hugged and kissed until it just seemed like enough and Oprah said, "You are a delight Jimmy. What time to we have to get on the road tomorrow?"

She was always all about business but it took me a few seconds to register and remember and I said "6:00 on the set, leave here at 5:30."

"Well then you better get to your room and get some sleep, don't want to be late." Replied Oprah.

So I gathered myself up and getting back to my room managed to get right to sleep and ready for the next day. The next morning nothing was said about the previous night but 2 days later Oprah requested that I come to her suite and again we wrestled, I won 2 of 3 and the winner again fucked the vanquished as a reward. And that's how it went the remaining 5 weeks of shooting, 2-3 evenings after we finished on the set, wrestling and fucking Oprah Winfrey.

When we wrapped the producer handed me a box that he said was a gift from Oprah. It contained a rather expensive carbon fiber briefcase and $20,000 in cash in a brown envelope with a note, "Just a tip for a job well done by a novice assistant who learned a lot in high school."

Of course it was pocket change to Oprah Winfrey but I'm still buying groceries with it. I never was sure if it was for my assistant duties, my wrestling victories or my sexual abilities. I only added a few of those to my resume but did chalk everything up to experience.