Boss Turns Into Cuckold   added 4 years ago
  By: sissyyvonne  Age: 62  Country: United States

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Categories: Oral Sex, Masturbation, Group Sex / Threesome, S-M / Domination / submissive
Tags: Cuckold becomes Boss sissy
Location: An office
Roleplay: Boss/Secretary
Fulfillment: Act on it
Nature: I will tell you later

It all began on a busy hectic day at the office. We were shipping some technical manuals we’ve been working on for the past few months. As the boss, I was right in there, meeting the deadlines with my very efficient crew. i was moving a few boxes with the hand truck and backed into the hanging fire extinguisher. It crashed onto my foot and i was in very severe pain. i hopped on one foot to my chair. Before i knew it my assistant removed my shoe and started to remove my sock. I knew I was in trouble but I was willing to forgo the embarrassment I was soon to face.

Liza pulled my sock down my leg and over my ankle. But, as soon as she touched my leg I knew… she would know. I was wearing women’s hose. She was very casual and said “my, my, what do we have here?”  By the time she had my sock off she saw my toe nails were pained a very bright red. Liza smiled. She said I would have to take the hose off and I quickly knew I’d have to remove my pants to do so. Liza locked the office door and said she loved men that tried to become feminine. She went on to say that from now on i would become her sissy cuckold. I didn’t even know what a cuckold was

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Liza pulled off my belt with such speed that the snapped and made that unmistakable snapping sound. She removed my pants and knew instantly that I wasn’t just wearing pantyhose. I was wearing a pair of black thigh highs attached to 8 garters of my red satin brocade under the breast corset. My c-cup breasts peeked over the top like an old western brothel saloon girl. i was also wearing a red thong that tucked my cock well..

Liza demanded that I remove my tie, shirt and tee shirt. When I did she let out a wolf whistle and I was very embarrassed. I never meant for anyone else to know. It was my secret. My c-cup breasts were pushed up and together providing nice feminine cleavage. Liza couldn’t keep her hands off my breasts and my ever hardening nipples. She pinched them a little then a lot then a lot more. She was more skilled then the pinching I could give myself. She went to her purse and produced a pair of chrome nipple clamps. I’ve only seen them and only imagined the pain they would produce.

She sucked and bit my right nipple then put the clamp on it. I was not prepared for the immediate pain. By the time she repeated the process for my left nipple. The pain in my toe had gone away. The clamps dangled over the top of the corset obscenely.  She flicked them a couple of times and i felt on fire. Liza had me sit and she tied my legs and arms to the chair. Liza asked if “i had any high heels” I replied they were in the bottom drawer. Liza found my pair of 6 inch red sling backs in my bottom file cabinet drawer.  After she put them on she asked if I had any lipstick. But as she did, she noticed my make-up bag also. You would have thought she struck Gold. She found my bright red fuck me plumping lipstick that I wear while I commute back and forth to work. With skill and expertise my lips were instantly red and were feeling tingly.

It was then that things got weird. She summoned John the office intern. He was about 6’5” and was built like a bull. Liza and John hugged and kissed like they had done that before. I could see their tongues dancing and igniting the spark of passionate love. She locked the door again and said to John “I have a surprise for you.” She glanced in my direction. This bull of a man saw me in my feminine glory. It took no urging to get John’s clothes off and soon he was in front of me. I have seen naked men before but I was not expecting to see such a huge throbbing cock in front of my face.

Liza told me to kiss the head. I did and my lipstick left lips marks. She told me to lick the head and she guided it into my lips. It was so big and wide and seemed to get bigger by the second. Once I had the head in my mouth Liza told me to suck. Suck the head, slide my mouth up and down his cock. She held my head so I couldn’t move backwards. I was forced to lean into that glorious piece of man flesh. I sucked and sucked moving up and down on that cock feeling it pulse and grow. John started to tense up and I sensed he was close to cumming, in my mouth. Oh how I wanted that. Oh how I wanted to taste him and savor the flavor of his manly honey cum.

Liza stopped him and she laid back on the desk. “Cum in me” she cried. In a flash he mounted  her and quickly his huge cock was imbedded in her.  She screamed and bucked thrusting her hips up to increase the depth of each stroke. She told me to lick his massive balls and suck gently on each. Like a choir they came together and screamed and carried on that i thought the desk was going to break. His huge and balls must have contained lots of cum. I was jealous. In the past all of my masturbation sessions ended with my cumming and I thought this time would be the same. Needless to say, I was wrong.

Liza and John untied me and laid my on the floor. She quickly straddled me grabbed the back of my head and pulled my face into her cunt. Her cunt was dripping with tablespoons of white cum, White honey. She told me she wasn’t going to let me go until I had sucked and licked and swallowed every single drop of  John’ cum load. She kept yelling for me to eat that big cream pie and savor the flavor. She told me to hold the cum in my mouth and let every taste bud experience the taste and texture of his cum mixed with her sweet pussy nectar.  What a sensuous smell, what a wonderful flavor. She bucked and moved so I knew she was cumming again. Finally she released my head and told me not to move but to lay there and swallow whatever crossed my lips.

Very soon my mouth was filled with hot liquid I swallowed as much as I could. The taste was very pungent. I then realized she had peed in my mouth. She said I should be prepared to do the same thing in the future whenever she had to pee.  I thought we were now done and it would be normal again.
 
Liza had a different idea. She placed John’s flaccid cock in my mouth and she told me to inhale the aroma. Savor  the taste, to enjoy a real man. All of the sudden, he started to release his golden nectar as well…




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