How I Tuned Office Newbie Into My Sissy (Part 1) free porn video

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The new boy started a few months ago, let's call him T, college drop out, 18, naive and innocent. As the closest employee to T's age my boss set me to look after him and show him around for the first week. From the moment I saw T I knew he was a sissy. 5'6, light caramel complexion and a perfume too feminine for someone wearing a shirt & tie combo. So I did what my boss told me to do, took him out for lunch for the first couple of days, got to know him fairly quickly and reached a comfortable level of friendship.. That's when I decided to test T, I was adamant then he was 1- in the closet, 2- virgin. I started talking about my sex life, trying to make him uncomfortable and thinking about me in a different light. Showing him girls I've been with and videos of me fucking..
....
Me "So, how many girls have you shagged? Must be a few, you're pretty cute"
T (going slightly red in the face) "a few yeah, you know how it is.." I could tell he was lying.
Me "Have you done anything freaky? Do you have any kinks?"
T (visibly uncomfortable) "No, what's that?.. You?"
Me "Keep this to yourself, I did fuck a crossdresser once but I honestly didn't know till he had my dick in his mouth and pulled his out and started walking! (laugh)"
T (still uncomfortable but looked intrigued) "Omg what did you do? Are you gay? Or bisexual? So how was it, would you do it again?"
Me "Yeah definitely, but I'd prefer a petite one next time so I could dominate and make it a regular thing, that was just a one off"
I left it at that, could feel his eyes following me as I put my rubbish in the bin and walked back to the office.. That's when I knew it was on, I'm going to turn this boy into a sissy.

Couple of weeks had past, I was making comments here and there about T's tight pants, feminine voice, walk, smell.. Putting my arm on his shoulder when talking and running my hand down his back before walking away etc. Then came that Friday where it went from comments to teasing to confirmed. T was making tea and coffee in the break room, so I went in and told him to make me a cup too..
....
Me "Put 2 sugars in mine"
T "Okay sir (laughs)"
Me (walked up behind him as he was stirring) "actually make that 2 and a half" (I then moved directly behind him, my body inches from his, took the spoon out of his hand from behind, put half a spoon of sugar into my cup and stirred slowly.. He was frozen solid, not moving, quietly breathing..)
T "I c-could do that"
Me (Didn't reply, kept stirring and edged closer until he could feel my semi on his lower back.. Tapped the spoon on my cup, put my left hand on his left hip, leaned my head into his neck and sniffed) "You smell nice today T" (took my cup and walked back to my desk)

....
End of that work day is when I made my move. It was raining and I noticed T walking to the bus stop, drove up beside him and told him to get in, I'd drop him off home. We talked about our weekend plans, neither of us had anything special planned. Asked him what he's doing tonight "nothing". I kept eyeing his thighs as I was driving, he knew what I wanted. I told him I was going to make a stop to smoke, I drove us to an empty factory carpark for a "cigarette", he didn't partake. I used the excuse of the smoke to say "You've got real nice lips, are you a good kisser?" I leaned in and he did too, we kissed and it turned into a snog. I pulled my seat back and reclined a little so he could straddle me as we kissed. My hands all over his arse, under his shirt, groping, grabbing and spanking as we suck tongues.. I told him to go back on his seat and pulled my cock out for him to suck, it was his first time but he was surprisingly good, sucked the tip and wanked the shaft, made himself gag etc. He kept trying to stroke his dick through his trousers but after the 3rd time I put my hand around his neck and told him "you cum when I let you".. T - "yes sir.."
After the blowjob we talked, he unwinded and told me all about himself, told him to meet me tomorrow (Saturday) as I'll be booking a hotel for us so I can take his virginity..

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Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

3 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

2 years ago
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Sissy Slumber Party

Sissy Slumber Party I was on my way to the slumber party and I was so excited that my panties were getting wet. As I felt the moisture between my legs I blushed and giggled. My high heels clicked on the sidewalk as I went and my full skirts and petticoats swooshed around my baby smooth nyloned legs. I wiggled down the street and my long curly hair and bangle earrings swung from side to side as I walked. Some men in a passing car whistled at me and I just smiled. But my panties...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

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