Boss and his Girly Boy

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I waited with bated breath as he went to close the door. Then I heard the click of the lock as it was slid over and he came back to me. I was still clutching my eyes tightly when I felt a soft nudge of his hard organ against my thighs. As I was closed to the outside world, I didn't knew when he stripped but I was sure he was already naked when I felt the hairy body scratching mine.

He took his time leisurely to kiss me neck before he started stripping. Soon, I was lying down wearing only my brassiere and panties. They were so sensitive and he kept planting butterfly kisses all over my body.

"You are so inviting," he said after which I couldn't feel his presence anywhere. When I opened my eyes trying to find him, he stood a few feet away still naked posing a raging hardon. He was shagging it to make it bigger and ready for penetration.

"Oh my god. Is he really going to put that thing inside me?" I felt a sudden rush of tension fill my blood vessels and my body displayed goosebumps as I continued to stare at his cock. Slowly, he walked towards me as his cock moved to and fro between his thighs. The next minute he was all over me and finally when I felt myself so wet with his saliva, I was nude. He cupped my small tits and held them forcefully in his hand.

"Ahhh..." moaned out of pain and pleasure. I couldn't say whether I liked it or abhorred it. But, the domination and humiliation with a string of pain did arouse me. It was hot when he bent lower to take it inside his mouth and started to suck my nipples. The erect nipples just loved his tongue rolling over it and he occasionally nibbled at them. I caressed his hair encouraging him to go further and he didn't let go of my tits for a long while.

"Ouch...hmmm" I moaned again when he took a bite off them. After when he finally felt it's time, he let go of them and spread my legs wider. Even after deciding to make his next move, I felt his body language wanted more of me. More of my breasts...the soft, tender flesh, the erect nipples and their feminine fragrance. I sensed his eagerness when he removed my bra and greedily looked at my budding breast.

Even before he came to kiss me, he was all over my tits caressing the flesh and now finally he wants to go all the way. Atleast now, he wanted to explore the other good assets of mine and provide ourselves some relief. The fear of impending pain was there in my heart, like a strong lump in the throat. But, I managed to free myself and carry on with my lover.

"Spread your legs, wider," he commanded me to which I obliged willingly and immediately. He didn't have to tell me twice that he's going to go for my ass without wasting more time on the preliminaries.

"Aaa...hhh" I felt a sharp tingling sensation when he pressed his hand on to my puckered ass. He couldn't slide it in as it was very dry. So, he smeared copious amount of fluid and tried his hands again. This time slowly but steadily it started going in. I felt so uneasy at first when a foreign hand invaded my most private place which is not meant to get fucked. The ass hole was designed for something else but then it didn't matter as for a boy who loves to become a girl, it is the last and best resort. Surrendering the flesh was the only way to take up a man inside so that he won't feel the difference of fucking a boy or a girl.

I tried hard to fight of the uneasy feeling and it did fade off shortly after he was done with the job. My boss spread my legs wider and continued fucking me with his two thick fingers. I had tried using a dildo but being fucked by someone else who also had a strong cock aroused me further.

He then took it out as I felt emptiness fill my now wet hole. I wanted him to go inside again and soon his cock tip was at my entrance.

"That feels like an iron rod. What the hell? It's so thick and fucking big. How will I ever get fucked getting it inside?" questions ran through my mind annoying me but it was not long before he started his journey. He started to push more of his cock and my ass was filled with excruciating pain. I couldn't stop him or the enveloping pain that made me cry at the instant. My tears filled with drops wet the bed. His hands had a tight grip on my thighs so that I may not clutch them together again when he's busy humping me.

"Please go slow...I can't take it," I begged him. He moved down and kissed my lips hard for once but didn't stop his motion. He just picked up speed later on and continued the sodomy.

"Ugghh...Ughhh," I continued to buck up and down as my body was plundered. He was going non-stop without respite and despite the cold atmosphere, I was sweating profusely. My erect nipples were topped with drops of sweat and my shallow tummy had sweat beads rolling on them which ended in my open legs for my lover.

He grunted hard and every time his grunt meant he was trying to go in deeper and harder. I held his shoulders for support and sensing the look in my eyes filled with passion, he came low and kissed me hard. I was lost in the kiss letting him suck and taste my lower lip then moving on to my upper.

The situation was so tense and in his furious copulation his belly managed to arouse my cock as hard as possible. It was constantly rubbed on and came to a state of utmost arousal. I know soon my cock would spurt its juices and I tried to wait patiently for my man to join my orgasm. But, unfortunately the rubbing was too good to bear and I ended up in a frantic moan.

"Ohhh...hmmm...aahhh," my voices were quite clear and I hoped deep in my heart that it shouldn't be loud enough for people outside to hear it. All the people in my neighborhood knew I stayed here and when I opened the door I saw some standing outside who saw him coming inside. Compared to him, I was a petite guy and even if someone comes to hear my moans they would assume it was me who is getting fucked for sure.

"I really don't want them to know or imagine how I might look when I am spread and getting humped by a man when I go out to office tomorrow," I nearly made a prayer at this moment before I was pulled back to my real life when my orgasm swept through my body.

'Oh god...oh..." I kept panting trying to catch my breath but it was impossible with my boss humping me so hard still. He soon reached the peak and grunted before I felt his warm cum fill my now not so virgin hole.

He slumped back onto my back crushing my body under his weight and soon rolled over to sleep. I was smiling to myself thinking that I got what I want and I knew how my life would go from here.

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4 Comments
AnonymousAnonymousover 6 years ago
English class would serve you well

I don’t know which is worse. This story or the total destruction of the English language by another anonymous commenter. The story itself is a good one but you definitely need an editor.

AnonymousAnonymousabout 8 years ago
good one

yes my boss he was a older man and I thought just for a joke I would buy some panties and wear them to work one day well It toke me three week to get them I was a store and I found the lady clothes I was looking at panties when I saw my boss in the store with his wife I just hope he did not see me in the were the panties are I just grab a few panties some were thong I then went to pay for them when I heard him say I hope you wear them one Monday morning I told him a lie that all I wear sir I been in panties for awhile good then I see you Monday come in the office when you get to work well Monday came and I was in his office he came in and lock the door he said good morning well man or should I call you sissy I old him want ever you want sir well let see how thing go for now are you wearing your panties I said yes sir then show me them sissy I said here now sir yes now I pull my pants off and now only standing in panties I had on a black lace thong panties what a lovey ass you have I think this will work out fine he walk over behind me put his hand on my ass yes I think I can use ass like this I ask him what he mean well since you like to be in girly panties I think you will be my girly bitch just then he ripe my panties off and pull his panties off I felt his cock go in my ass hole you have one tight pussy ass girl well after that I become his office bitch and then it happen his wife walk in and said dear is your girly bitch ready to with me he said yes dear and have fun I see you two at home well that afternoon I was change into a girl I had my nails done ear ring pit in and I had fake breasts glue on till my grow out then I was to get my hair done and make up when we got home the boss was there he look at me what a lovey girl if I did knot know he was a man dear I think she pass yes dear and she ask to be call sissy girl then she told me go and give your master some loving I knew what to do right in front of his wife I toke his cock out and suck him off now that my girl and now I been there bitch

AnonymousAnonymousover 8 years ago
Sexy

:)

It is hard to resist the temptation.

AnonymousAnonymousover 8 years ago
interesting story

This was a bit different from other CD sissy stories but it really did turn me on. I too have been having sexual fantasies about my boss and he too has a big cock that I drool over. Maybe I should let him read this story and he'll get the hint that I want him to feed me his cock and fuck my man-pussy deep and hard. Wish me luck.

Please tell more stories like this one.

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