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How I tuned office newbie into my sissy (Part 1)

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)
*this is when he finally knew I wasn’t messing around*
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. **no video of this but I did have photos which were since deleted as I didn’t need to f***e him to be my sissy!** 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..


Updated: October 21, 2016 — 1:30 pm

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