My Boss Stephanie Mcmahon

THIS IS A FANTASY...IT IS NOT REAL

I was looking over my to do list in my seat on one of the private jet. It was headed back to Stamford. My boss Stephanie McMahon, I'm her PA, and I had left Detroit after Smackdown Live. She was busy on the phone talking to her husband HHH, who was on his way to the Performance Center in Orlando to check on Ronda Rousey's progress.

I enjoy my job since I grew up a wrestling fan and it's allowed me to be around the business. I have met a lot of cool people and I've seen the world as well. It's cool seeing a show in front of a big crowd and feeling the energy in the building. As a fan of wrestling it's a special feeling for me, just imagining walking down the ramp and the crowd chanting your name. Standing in the ring as the crowd goes crazy, it would be such a cool experience.

I was horny as hell, since my job doesn't allow me a lot of free time and hanging around all the hot women wrestlers, as well as other employees, tends to induce erections.

I rubbed my now half hard cock through my pants. I saw Stephanie was off the phone and walking towards me so I stopped rubbing myself.

"Dick, sometimes I wonder if I made the right decision going into the family business. It's so time consuming and the stress is killing me. It's hard being the Billion Dollar Princess." She laughed, referring to her heel character on TV.

"Well Steph, get a massage or something. You are the Billion Dollar Princess, so I'm sure you could afford a really good one. You might could even get a very happy ending." I smiled as I said it.

We do flirt back and forth, innocently. She and I get along really well and we are friends as well as boss and employee. She's also hot as hell so it's cool getting to flirt with her.

She sat down beside me and turned away from me, pointing to her shoulders. "Get to work Dick, and maybe we both can have a very happy ending." She said jokingly. Steph likes to play with me verbally, always teasing me, because she knows I think she's hot. She loves to lean over as she talks to me to show me her ample cleavage, and lick her lips when she talks. She's a very talented cock tease but she never goes too far with it. She enjoys turning me on but stops short of instigating any extra marital activities.

I started rubbing her shoulders. She moaned and slowly moved her head from side to side so I continued rubbing. She smelled great, she always does. She spends a lot of money on her appearance, always dressing well and wearing the best make up as well as having her hair styled at the best salons. She also wears sweet smelling perfumes. She is gorgeous and she knows it. She loves to flaunt it, in a sophisticated way, but sometimes she will just put on a very small bikini at the pool and flaunt it in a more direct way.

I continued rubbing her shoulders as she told me to keep going. "Very good Dick, your hands may get a raise...and maybe you will as well." She laughed and looked back at me smiling, holding her long brown hair up off her shoulders.

"Well Steph, my hands do work overtime, between all the stuff I write down for you and all of the time I spend thinking about how gorgeous you are, they stay very busy." I laughed, teasing back at her.

"Oh really? They work really hard thinking about me? I bet you think about me really HARD." She said smirking at me. If she only knew how Hard I thought about her, I told myself smiling back at her.

She thanked me for the neck rub as she sat back in her seat. She told me what was on the schedule for tomorrow. I wrote down everything, looking at her and my mini notebook as needed. She stretched her arms as she talked to me. She was wearing a white button down blouse, she had taken off her jacket. I could see her cleavage thanks to her having unbuttoned it to the tops of her beautiful DD cup breasts. It was a distraction but I was used to it, having been around the gorgeous Stephanie for awhile now.

Stephanie's job title for WWE is Chief Brand Officer. She basically goes around promoting WWE and putting together promotional campaigns for different causes. The whole on air role of her running the company is just a storyline. She's not involved with the wrestling side of the company anymore, except for some ideas for the Women's Division from time to time.

I enjoy hanging out with her, not only because of the flirting but also she is a friend and she always asks if I wanna talk or if I need anything. She's a great boss.

She kept talking about what we needed to do tomorrow at the office while she closed her eyes. I wrote everything down, but she soon nodded off. I put my notebook down and sat back in my seat to relax as well. I looked over at her and she was lightly touching her beautiful breasts through her blouse. I didn't wanna stare too hard, knowing she was asleep so she was dreaming, she probably didn't want me to see it.

I am a very horny guy that thinks she's super hot so I did look of course, watching her play with those magnificent breasts. I even rubbed my cock for a minute, then my friend of hers side showed up and I stopped rubbing and looking.

She woke up and looked at her hand still on her breasts and looked slightly ashamed of herself for touching them in front of me while she slept. "Sorry about that Dick." She said half smiling at me.

"No problem Steph, no problem at all." I smiled back at her.

Stephanie got up and went to the bathroom to freshen up before we landed. The stewardess Lori came over to me and asked if I was OK. I told her I was and looked at her. She was beautiful, about 6 feet tall with long legs and beautiful DD cup breasts like Stephanie. She has long blonde hair that cascaded down her back. She was the most beautiful stewardess I have ever seen. She smiled at me as she noticed my bulge in my pants that Stephanie caused and didn't notice.

I looked at it and her and said "sorry, just excited to be home." We both laughed. She leaned over to my face and asked if I needed any help with that. I wanted to say hell yes but I saw Stephanie coming back from the bathroom, so I just told her no thanks. She could sense my disappointment so she told me" maybe later." I told her sure, as she walked back to her post making sure everything was in order before we landed.

Stephanie smiled at Lori as she walked by and sat down beside me again. She put her hand on my leg not looking at me or my half hard erection in my pants. "I wanna learn how to be able to work hard and relax a lot more at the same time Dick, could you please teach me?"

"Yes ma'am, I will try my best." I smiled at her when I said it but I started to think, was she thinking what I was thinking? Is my idea of "relax a lot more" the same as hers? I didn't wanna push too far and piss her off or get fired, but I was also very intrigued by her request.

She pulled her hand off of my legand we buckled up as the pilot said we were gone a land.

When we landed and got ready to exit the private jet, Stephanie looked at me and said as she smirked "I guess you were only thinking about me HALF as HARD as usual." She laughed as she exited the plane. I smiled realizing she did actually notice my half erection earlier.

We got in the limo and headed home. I live in Stamford but she and her family live in Greenwich. She told the driver to go to her house and looked at me to say "you can spend the rest of the late night at my place and we can drive to work from there." I told her that was fine and we made our way back to her beautiful home in Greenwich.

We arrived at her place around 3:30 am. She talked to the nanny who said her kids were in bed and everything was OK. The live in nanny went to bed and Steph showed me to my room. I tossed my suitcase down and fell on the bed dead tired. I took my clothes off, tossing them on the floor and crawled under the covers nude to get a couple of hours sleep.

About 15 minutes later I was half asleep when my door opened. I looked over and saw Stephanie come in. She sat down on my bed and said "I'm sorry to wake you Dick, I just wanted to let you know that I was sorry for asking you to help me relax. I know we are friends and I'm married so I didn't want you to feel awkward about anything. I cherish our friendship, you're a great guy. I also appreciate you not trying something with me when I was asleep and touching myself. I know you like me that way and it's flattering. You are very handsome it's one of the reasons I hired you." She smiled. She can be very sweet when she wants to be, she's so easy to have a crush on. Beauty, a sweet side and those incredible breasts, she's amazing.

She was wearing just a towel that she was holding around her. She leaned over and kissed my cheek, holding her face on mine. She got up and started to leave my room. She stopped and turned around looking at me. She all of a sudden opened her towel and showed me the goods. She was completely nude. I looked her over up and down, side to side in awe of her body. She is truly one of the most gorgeous women ever.

She put her towel back around her and said "make sure you think of me extra HARD tonight Dick."

She laughed and left my room. I started rubbing my now fully hard cock as I smiled thinking about her.

I must've slept hard because I woke up and Stephanie was in my room again, fully dressed this time, sitting on the bed beside me looking at me. She smiled when I woke up "good morning sleepy head." She said. She was amazing it was 7 am and she looked incredible. She wore a tight, black pantsuit, her long brown hair flowing down several inches below her shoulders. I told her good morning and rubbed my eyes. I looked down and saw my rock hard, fully erect cock tenting the covers. She saw it too. She grabbed it and said "glad you thought about me REALLY HARD last night." She squeezed and jerked it once before releasing it. She told me to get dressed so we could head out to the office.

I got up, showered and got dressed and met Stephanie downstairs in the driveway. I skipped breakfast, as I was running late. We headed out to Stamford.

On the way to WWE headquarters, in the back of the limo, Stephanie handed me a breakfast burrito she had made herself. She felt sorry for me skipping breakfast and told me to eat it. "You're gonna need your energy today Dick, it's gonna be a very busy day for you." She said putting her hand on my leg. I was used to busy days and long hours, but her hand on my leg was making me look forward to this particular busy day.

She rubbed my leg, not looking at me. Her hand crept slightly higher as I ate her rather tasty burrito. She then turned to me, her face inches from mine and moved her hand directly onto my soft cock. She rubbed it and whispered in my ear, in a very sexy voice, "I need you to work extra HARD for me today Dick. Can you handle that Dick?" My now very HARD cock should've given her my answer, but I went ahead and answered "yes ma'am, I definitely can."

She grabbed my cock and jerked it through my pants slowly. I had finished the burrito thankfully, so I could just enjoy her handjob uninterrupted. She softly kissed my cheek as she slowly jerked my cock. It felt so fucking good. Her hand slowly working my hard cock up and down. She licked my neck slowly and I thought I would bust a nut right then, but I didn't. I was in heaven, getting a great handjob from my boss, who just so happened to be one of the sexiest women ever on this planet.

She jerked me a little faster, nibbling my ear. My eyes were closed, enjoying every last damn second of this. She whispered in my ear in her sexiest voice "I'm not wearing a bra Dick...or panties." That was it, my cock was so damn hard it felt like it was harder than steel. She jerked me faster and rubbed her big tits on my arm though her blouse. She could sense I was gonna cum so she jerked faster, I moaned so she jerked faster. I moaned really loud. She jerked my cock faster and...stopped. She held it still, her hand over the head, squeezing it, so I couldn't cum. When she was satisfied I wasn't gonna cum, she let it go. "Time to get to work." She said as we arrived at WWE headquarters. She kissed my cheek and softly patted my well teased but still hard cock and we went in to get to work.

The day progressed as usual, a lot of phone calls and several meetings. Stephanie was very business like, so I was a little disappointed. I started to think she was just teasing me in the limo on the way to work and the HARD day she talked about, was just work.

At around 3 pm she called for me to come in her office quickly. I ran next door and opened her door. She was bent over her desk looking though some papers. I took in the sight for a few seconds, that beautiful ass in those tight pants. My cock was half hard and I touched it before she turned her head to me.

"Dick, where in the hell is the contract I asked you about after the meeting?" I can't find it and it's stressing me out."

I went over to her and helped her find it. She thanked me and looked it over. She sat on the edge of her desk with her legs crossed and put the contract down.

"Thanks again for finding it. My stress level has been at an all time high today. This job gets to me sometimes, so I'm glad you're here with me sexy man." She looked at me smiling that sexy smile of hers. She saw my half hard cock and smirked. "Only been thinking about me HALF HARD again I see." She got up and walked slowly to her door and closed it, locking it. She sat back down on her desk and told me to sit in the chair facing her. I sat down and looked at her. She was in all her sexually seductive glory right now. She crossed her legs and smiled a devilish smile at me.

My cock was now rock hard and tenting my pants. She reached her high heeled foot over and slowly rubbed my cock with it. Slowly up and down she rubbed, looking right at me not saying a word. I stretched out my legs, getting comfortable and enjoyed the footjob. She took her jacket off while she continued rubbing my throbbing cock through my pants. She slowly unbuttoned two buttons on her blouse. She slightly opened her blouse, showing me the insides of those magnificent DD cup breasts.

"Take out your big cock Dick. I wanna see it now!" She ordered and I obeyed. I unzipped my pants, my throbbing cock springing out in excitement.

"Very nice, my sexy helper." She smiled, as she licked her lips in approval of my cock.

She rubbed it some more with her foot, her eyes locked onto mine. She then opened her blouse all the way, without taking it off. She rubbed her nipples as she continued her footjob on my cock.

I looked at those big rounded tits with their hard, thick, brown nipples and quarter sized, brown areola, breathing hard, admiring them. She smiled, knowing how much I liked them. She slowly rubbed each erect nipple, lightly pinching them, smiling seductively at me. She then cupped her big tits in her hands, shaking them, squeezing them.

My cock was so hard from her footjob, I wiggled it at her without using my hands. She laughed and got up from her desk, standing right in front of me. She looked at me as I jacked my cock slowly. She smiled and knelt in front of me. She locked her beautiful brown eyes onto me and bent her head over. She stuck out her long tongue and slowly licked up the underside of my cock, her brown eyes glued to mine. I breathed hard, basking in the feeling. She looked so amazingly sexy licking my throbbing cock. I took a mental picture of the sight.

She licked under the sensitive head and slowly lapped up the precum oozing out of the slit. She stuck her smooth tongue into the slit and wiggled it around. I groaned, loving the feeling. She laughed and smiled, knowing how much she was pleasing me. She started sucking the head, her eyes never leaving mine, concentrating on just the throbbing head at the moment. She sucked it harder, inducing another happy groan from me. She then sucked slowly down the base. She took in inch after inch, slowing making her way all the way down. She stuck her very soft hand inside her pants and started playing with her pussy. She undid her pants to let me watch her fingering her wet pussy as she sucked my rock hard cock.

I put my hand on her head, pushing her further, but she didn't need the help. She took in my whole cock, looking up at me with her cherry red lips on my crotch. I shave down there, so there were no nasty public hairs to get in the way. I took another mental snapshot and blew her a kiss.

She grabbed my big balls and softly rubbed them as she sucked all the way up and all the way down on my rock hard cock. She lightly grazed the head of my cock with her teeth and sucked it really hard, shaking her head and playing with my balls. She deep throated me fast. She took every hard inch in every time, her head speeding up and down my cock.

My cock twitched and I held her head on it wanting to cum in that beautiful, soft, inviting mouth. Once again she didn't need the help as she gleefully smiled at me and sucked my pulsing cock faster awaiting my cream. She sucked it faster and jacked it as well. After a minute of that, I looked right at her and came hard into her waiting mouth, unleashing a torrent of thick creamy nut into it. She sucked hard and swallowed as I kept cumming in her hungry mouth. When I finally stopped, she moaned in approval of the taste and sucked me dry, swallowing every single drop of my thick cum.

I picked her up and sat her on the edge of her desk, leaning her back. I kissed her, tasting those cherry red full lips. We both hurriedly removed our clothes, tossing them aside, as I knelt on the floor. I rubbed her long well toned soft legs. I leaned in as I slowly licked up and down her slit, my eyes glued to hers as she played with her big tits and looked at me smiling. I kissed her slit softly, rubbing her clit and softly smacking it. I twisted my tongue slowly up and down her labia, watching her the whole time.

She grabbed my hair and clenched it in her hand as I twisted my tongue into her wet pussy. I licked every inch of her inner folds that I could reach with my tongue. My tongue darted in every direction, licking fast as I twisted it in and out of her pussy. I softly smacked her clit, rubbing it between smacks. I reached up and squeezed her big tits, rubbing her nipples as I worked on her pussy.

Stephanie moaned uncontrollably as I ate her out, shaking my head by my hair. I pinched her eraser sized clit, holding it for several seconds before I pulled it and rubbed it with my thumb. I continued to tongue fuck her, licking her upper pussy wall slowly like a vacuum as I brought my tongue out. I quickly licked her clit, keenly watching her writhe in pleasure as I began to suck it. I pulled it hard with my mouth sucking it hard, then letting it pop back in place licking it slowly, looking directly into her eyes. I paused with my tongue outstretched on her throbbing clit and smiled at her.

She was pulling her nipples and shaking them as I worked her pussy to the brink. She squeezed her amazing, huge tits hard, watching me eat her out.

"I'm gonna cum Dick. Lick it all up baby." She moaned loud, breathing heavily and sticking out her tongue, as she came on mine. I shoved it back in her leaking pussy to catch her juices. I licked it as they flowed onto my tongue, swallowing it as it did. I licked her clean, then I moved up and kissed her, letting her taste herself. I kissed her deeply, licking her tongue, fucking it as I kissed her.

I pinched her thick nipples, twisting them as I kissed her, groping her perfect tits.

I put her legs on my shoulders and rubbed my aching cock slowly on her soft, light brown labia. I blew her a kiss as I did and she licked her tongue out at me. I rubbed on her labia and clit. I smacked both with my still hard cock, then positioned it at the entrance to her pussy.