The Sissy Cuckold

At 49 years of age I was content. I was manager of a small company on a good salary and I was not the sissy cuckold. Comfortable that I was in charge of my life. A bit too confident in my dealing with my staff, maybe to the point of being arrogant…

The way I conducted myself drew the interest of Linda a long-time staff member.
Linda, a 45-year-old woman who carried herself well above her pay rate and showed me her interest whenever she had the opportunity. I was very attracted to her. She was beautiful in that earthy way…let the greys show though, no makeup and I knew she had hairy arm pits and snatch as we were also in a sexual relationship. It just happened at a work conference.

Sex at home had stopped and Linda was special in that she liked to dominate in the bedroom and away from work. The whole office knew and she used our relationship to belittle me. I am sure she told all the women I had a small cock and wasn’t any good with what I had. She would delight at meetings wiggling her little finger towards me. I felt humiliated. At the same time, it stirred submissive desire. I think Linda recognised it as she further explored BDSM activities with me

How I Became The Sissy Cuckold

I had no choice but tolerate her behavior as she had drawn me into Domme/sub relationship. I discovered the joy of submission and joy of sex as never before as she continued to push my boundaries.

She had taken my dignity, but I didn’t care I was consumed by Linda, submission and sex. Complete addiction. She introduced me to many new activities that I thought I would never do. I am not sure if Linda identified me as a submissive before or after our first time.

My time with Linda was mostly spent on all fours with arse in the air, always naked in her presence. She loved to redden my arse with her paddle. Prolonged periods of licking her rather large clit moving up to her eager anus. (Had to use mouth wash if I went back to her clit.)

Forced to clean up her bush after urinating telling me it was good to get use to the taste of her “golden nectar” alarm bells ringing!

I was deeply in love with Linda. A Domme/sub is the most emotionally charge relationship. For BDSM activities trust develops a bond. The sub is so grateful for small kindness which might be by just stopping punishment….allowed on the lounge. Similar to the relationship of hostages and their captures. Unfortunately, it is mostly one-sided love from the submissive.

The Sissy Cuckold – Becoming 24/7

Because of my attachment to Linda, I was spending as much time as I could with her. Of course, my wife became aware of Linda. Luckly not our activities. I had nowhere to go. Linda agreed to take me in but some changes in how our relationship was conducted.

I would be 24/7 submissive in all things and now she had better access to my training she wanted to explore my fem side. She told me it was always something she wanted to try. Sounded fun….I agreed to shaving all my body including armpits.

I was to stop having head hair cuts. My toe nails painted red. Always wear ladies perfume . Sun bake in a bra so when home naked I would have the out line of the bra and white tits. All of which I could hide at work.

She loved the look so much . “A girl doesn’t need a cock” she said. Then told me my cock was to be caged when away from her. And a girl needs a pussy for their enjoyment. I was to start training my pussy. With the help of butt plugs I made my arse/pussy more accommodating.

Linda loved her strap on…I would have to suck it before she fucked me. When my cock was caged and anal milking was my only relief Linda was amused how her new girly slut would push back on the strap on.

The Sissy Cuckold – Transformation

Linda had achieved the transformation of her old boss. She was happy with her creation…a submissive fem boi who could met her desire to Dominate and sexual satisfaction mainly though oral. But the need to be voilated was in the back of her mind.

I knew Linda was always interested in a cuckold relationship. She had created that submissive cockold. Linda also knew of my love for her so a deep emotional attachment to be played with. Plus she could ensure I was desperate for sexual relief by locking my cock away. It wasn’t all about the sex it was also about my humiliation.

Linda arranged the “Bull” though a girl friend in a swingers group. The group were required to have regular heatlh checks. And the girl friend knew which men were well hung and safe to invite into your home.

The Sissy Cuckold – The First Date

The date was set around Linda’s cycle. Two weeks out my cock was caged when I was not supervised. No anal milking.

Linda was excited about me watching her be fucked by a real man she kept telling me. She planned it all in detail. To add to my humiliation I was to answer the door, show the “Bull” where the bathroom was, offer a drink then lead into the bedroom like a good cuckold.

Than I was to perform oral until the “Bull” pulled me away.

The day arrived….as usual I was naked wearing a nice perfume. Linda’s bra tanning idea even made me look more naked….white tits and for the big day added a darker coloured make up to my nipples. My hair had grown longer …shaved up under the hair line. Looking in the mirror it was hard to see a man bar for narrow hips and a caged cock.

The door bell rang. I was nervous…embarressed to be opening to door to a Alpha male. I opened the door and in a trembling voice introduced myself. I was waiting for the distain on his face but was met with something else.

He stepped in the door , he was a big man muscled more from work rather than the gym. He starred at me while he traced the tanned out line of the bra. His hand was rough but moved gently across my tits. Than with his other hand he tapped me on the arse as he asked for the bathroom.

I showed him the door. He moved me aside by gently putting his arm around my waist. As I waited for him I could not help but alter my stance moving my knees together kicking one foot out to the side. He had excited me in ways I never thought possible. But I had not cum in two weeks and my cock was dripping on the floor.

I lead him into Linda’s room. They introduced each other. She was naked under the sheet which she throw back and gestured me to get my tongue between her legs.

She was so wet, her juices had saturated her hairy bush and sheet. My tongue touched her swollen clit, she groaned pushing forward. I moved my mouth down across her opening to drink her juices but she grabbed me by the hair and pressed me back on her clit.

I was on all fours…arse in the air. I felt that rough strong hand caress my butt cheeks…run his finger between , linger across my pussy, take hold of my full balls…rolling them in his hand.

I had never had a man in me but I spread my legs wider pushing my arse sky ward hoping to tempt him. I was wanting cock. The transformation complete.

Linda pushed me aside and gestured to the “Bull” it was his turn. I seen his huge cock already erect, he was covered in hair. What a true man should look like. He slowly and gently entered Linda while she arched her back.

He slowly moved his cock in and out.
“Slap!!!!” Linda hit him across the face. Yelling ” fuck me like you mean it”

The big man was stunted and angry….holding her hips he drove his cock into her. The bed moved with each thrust. A thud as she took all his cock. She stopped looking at me. She was just trying to hang on for the ride…eyes shut,somewhere between pleasure and pain.

He roared as his cock exploded in her…grinding up against her not releasing her until very drop of cum had been transferred.

He finally withdraw his magnificent manhood…dripping a mixture of his cum and her juices.

He dressed and I let him out the door. His passing gesture was a surprise kiss on the cheek. Maybe a promise of things to come.

Linda was calling me back in the room. I am sore down there. It needs kissing better. My cock was still pressing hard against the cage so I was keen to please. My tongue once again touched her clit.

She jumped back it was still too sensitive. I moved my tongue and mouth to cover her hole. I had never tasted another man’s cum…but as I licked and sucked his cum I was thinking of a real Man. I am now the Sissy Cuckold?

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