Blackmailed Secretary   added 3 years ago
  By: gray6lover009  Age: 59  Country: United States

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Views: 964
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Categories: Anal Sex
Tags: first-time erection
Location: A hotel room
Roleplay: Boss/Secretary
Fulfillment: Share it only
Nature: Agressive

I was on my way to my corporate office in Chicago. The plane ride makes me listless and

being cooped up in an area that confined always makes me horny. There's nothing

else to think about! So I arrive at the office, my office manager Lynn walks towards me

dressed in a very tight sexy, somewhat office appropriate outfit. I observed that Lynn was

very wet and ready to be taken to bed. I could see her stockings clinging to her thighs trying to stay warm, the garter getting stuck in the creases of her lower body. Other parts of her body told me she was very cold.

Lynn and I had known each other for 5 years. She lived for a short time

in my apartment when I was in between girlfriends. I used fondle and caress her breasts, or rub her body when I was lonely or just aroused. I was 25 at the time. I never crossed a line, for that

reason we remained friends. I liked to be assertive and controlling, enjoying shoveing my cock

down her throat shouting vulgarities at her like "take it all down your throat

slut", makes me aroused.

I can be a very, very bad boy, I remember cuddling up to her body at night playing innocent.

I tried my best to pretend I wasn't aroused by her short little outfits that she wore to bed. She pretended not to notice. Anyway, we were just friends and I had called her to accept

what I called an executive position in my corporate office. I had become a powerfully rich man, pioneering a new kind of software for the internet. My office was in an ominous looking building.

I got in the elevator and could feel eyes on me wondering why the CEO was there. Lynn meet me as I existed the elevator. Her body shivered under the cold and embarrassment, when I saw how rock hard her nipples were protruding in her white blouse. Fuck, I felt real a horny now. We went to her office. I opened the office door for her. I looked up and down her slender body as I closed the door. I had a lustful smile and lust in my eyes as she turned to face me.

So, you have proven your self in running this office Lynn. I walked over to the window exposing a very well tailored expensive suit. "How is your husband?" Lynn replied he is fine. Lynn walked to the desk making sure to sway her hips in a sexy teasing manner. Does your husband know about the nude photos? Lynn's face turned white. How did he know about them. You probably did not realize that we know alot of the same people Lynn. Your husband works for one of my business partner's. I hear your body is beautiful and very responsive to fucking. Let me call him as I picked up the phone. Lynn stopped me, she looked at me begging me not too.

We were undressing each other with our eyes. This evening you will come to my hotel suite at 7pm. Lynn, you will wear something a little more revealing then what you are now, although I am enjoying the free show. I motioned to the light white blouse that was mostly transparent where you could visibly see her tits hanging out of her bra. Show me the color of your panties. Lynn hesitantly walked over to the desk. She slowly slid the tight skirt over her thighs revealing her stockings stuck tight to her moist thighs, the hot little garter belt and her lacy pink panties. I grabbed her hips and pulled her forward.

I had been horny on the plane and couldn't wait to get to my hotel room to masturbate. The scenario here in her office wasn't helping. Lynn was embarassed that I had caught her wet. Her scent wafted through the office. I slid her panties down and probed her lips. She jumped back slightly feeling her face flush. I looked at her devilishly. Sign the papers out on the desk and be at my suite at 7pm. Wear no stockings, something obscenely short and a thong. Lynn got dressed and started for the door. As she reached the door, I clicked on a tv in the office of a tape of her posing nude and begging to be fucked.

The evening was freezing cold. Lynn ran from the cab in her short skirt with no stockings on as she had been ordered to wear. She clung to her coat feeling her breasts bouncing in the low cut silky material of her blouse. Lynn was angry that I was making her do this, but aroused at feeling she didn't have a choice. She scrambled into the elevator almost tripping in her high heels. Lynn would do anything to please me, to keep it all a secret. Lynn exited the elevator, she gasped when she felt a hand on her ass cheek. She turned abruptly to see me lustily looking at her. Lynn glared clenching her teeth while trying to brush my hand away, but it was already traveling up her thigh.

As Lynn and I entered the suite, I growled as I glared at her coat. Closing the door, strip. Strip? Please,uh don't make me. Lynn slowly pulled the coat off her shoulders. She pulled down the zipper of a very form fitting dress revealing her curvy figure. Her long black hair brushed her cheeks as she pulled down the tight, dark green tweed dress that was obscenely short. She stood with her hands on her small waist daring me to order her again. Her nipples were feeling the effects of losing the dress. Take it all off, she obeyed. She slid the straps of her tight black bra off her shoulders one at a time. Her tits had been bulging out of the small cups were happy to be released bouncing forward freely when she unclasped the back.

She slid her fingers down her stomach to the string of her black transparent thong and pulled it slowly down her thighs. She stood naked before me shivering slightly. She started to remove her heels but I told her to keep them on because I liked it. Relax, I always knew you had gorgeous tits but you're really well proportioned woman. Turn around let me see that beautiful firm ass. Lynn dutifully did as I asked. Come here, she walked slowly over to me swaying her hips. Bend over the arm of the sofa. Lynn bent over the sofa arm, I reached out and grabbed a handful of her hair yanking her head back. She cried out with the sudden surge of pain. I probed her small tight asshole a bit with my finger.

She jumped feeling me touch her in between her cheeks. I slid my finger down to her lips where I chuckled. She was soaking wet. I started to slowly push my finger into her dripping pussy and rubbed her ass with my other hand. She wriggled a little as I continued to push my finger in and out of her. She felt nauseous, even though her body was responding sexually. She stared forward expressionless feeling her body involuntarily push back on my hand dripping with her juices. I took the juices from her pussy and rubbed them in between her cheeks. I was intent on wetting her anus and watching her writhe in anticipation.

Lynn was shuddering in disgust. If you didn't like it than why are you so wet? I seductively, implyed I was going to fuck her ass. Lynn noticed how aroused I was. Get on your knees, I undid my belt dropping my pants, freeing my 14 inch and 3 inch wide hard rock cock. Lynn had tears in her eyes.

Now suck my cock. As I held her my cock was poking her tits. I wrapped my hand around my cock and with my other hand I grabbed her by the hair. Open your mouth baby, and put your pretty little lips around my cock. Lynn opened her mouth letting me slide my cock down into her throat. She moaned softly as I guided my cock in and out. She tried to stroke the head with her tongue and flick the head. It proved very difficult as I was so far down her throat.

Lynn looked up at me to see if she was pleasing me. She wanted to look at me while sucking my cock but I roughly held her head, forcing her back down on my cock. I groaned plunging deeper into her throat. I pulled out of her mouth, my pre-cum and her saliva all over my cock. Lynn realized she still had her mouth open begging for more slightly drooling at the sight of the stream of fluid from her mouth to my throbbing cock. Lynn continued to do the job she was hired to

do. She tightened her grasp on me, sucking in her cheeks to create a tremendous

pressure around my cock. My reaction was the one she desired and she felt me

grow larger as I pushed deeper and deeper into the taught muscles of her throat.

She let the head of my cock rest on her tongue, stroking my shaft while working up a

rhythm I railed her mouth. She coughed pulling suddenly off of me. I

reached out grabbing her hair and plunged back into the warm wetness knowing she

was choking on my length. I smiled lovingly how she struggled to look up into my

eyes and take the pain of being suffocated by my cock. She glared up at me as I

mocked her subservient position. She stood and stretched the

length of her body over the arm of the sofa, She felt me position my body behind her.

I leaned over and told her to relax and enjoy the afternoon with me. She wanted to pull away but I held her hips in place roughly with my controlling hands. I moved one hand to caress the skin

of her back, my long soft hair, and down her back to her ass. She stood in such a venerable position with her ass hanging nude in the air waiting to be fucked. She looked back to

see me rubbing my cock up and down her pussy lips. Her breathing started to

grow heavy as I started to feel her wetness with the head of my cock. She was secretly craving cock. I pulled my hard cock away and inserted two fingers into her dripping pussy.

As I inserted my fingers her cum squirted out onto her thighs as I teased her mercilessly. I used my other hand to reach in between her ass cheeks. Um, Um at the feel of her tight asshole. Her breathing grew rapid as I continued to finger her faster and inserted my thumb into her ass. Her muscles tightened around my finger. Feeling her muscles tightening around my finger, I pushed harder and faster. She moaned Uha! Uha! Ohhha! Uhha! She threw her head back towards me.

She pushed back on my fingers helping her to orgasm, she reached back to rub her own asshole.

I was breathing hard, my body beginning to shake as I was about to cum. I quickly thrusted my cock deep into her wet pussy. Ohhhhhhh! Ohhhhhhhh wow! FUCK ME! OH YES! she screamed. I reached down pulling at her tits. Ya, baby those are beautiful tits. I wrapped my hand around her hair twice, tightly grasping, hair wrapped around my knuckles. She didn't argue. She begged me over and over to ram my long hard cock into her. I suddenly drove my 14 inch long hard cock all the way into her. She squeezed tightening her muscles around my cock trying to make me cum early, I didn't cum. Thrusting fast like a pile driver deep into her, my cock and balls slapping aganist her and the wetness of her pussy swallowing my rock hard cock. Each thrust buried my long wide cock deep into her jucies.

I groaned loud as I erupted in her, my cum flowing like molten lava filling her. My breathing was heavy as I collapsed aganist her. I pulled out of her pussy, repositioning myself between her spread legs. I pressed my naked body aganist Lynn, she felt my big hard cock push between her cheeks of her ass, resting on her anus. OMG! it felt like it was over 10 inches long and it must be over 3 inches in diameter. Lynn began to sweat in fear of her first anal fuck. I wrapped my arms around her and my hands squeezed her breasts and pinched her nipples. "OOOWW, that hurts. "That's nothing, wait until my cock forces its way into your asshole."

Lynn felt me push up from my body and fist my cock and place it on her anus. "Your ass fucking is about to begin" and I began to push the bulbous head into her anus. My cock was dry so all it did was try to push her anus into her body. I spit down on my cock to lubricate it and again pushed into her anus. It felt like a baseball bat was driving up her ass as I continued to push and pull back and push again, each time gaining an inch at a time. "OOOOOWWW, its too big, don't stick it into my ass," she wailed. I pushed harder and Lynn's anus gave up to the assualt and opened to the head of my cock.

"AAAAAAAAHHH, OWWWWWWW, it is hurting me, take it out, don't push it in," she yelled. "You only got the head, wait until you get all 14 inches fucked up your ass. I pushed another inch in, then out. The next thrust gained two inches, then back out. Lynn's asshole was bleeding from the assualt, lubricating my cock for me to continue. "Here comes all of it" and I pushed with all of my might into her asshole. Fourteen inches of hard cock forcing her asshole to open to accept the fucking of her tight virgin ass. I pulled my cock out to the head and then began the painful journey back up her ass.

Her ass tightly gripped my cock. I began fucking her ass hard and fast, riding her. My cock drove deeper into each time, cramping her as it was forced to accept my hard cock. I let out a loud groan with one final driving thrust into her ass, she screamed. I collapsed aganist her pressing her onto the arm of the sofa. Our bodies dripping wet in sweat and we were gasping for breath. I pulled out of Lynn looking at her bent over naked with cum dripping from her swollen red anus. "You were a great fuck, Lynn. Well, see you again on my next visit." I said. "Go get dressed." Lynn picked up her clothes going into the bathroom sobbing with tears running down her face.




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