As soon as I got home after dropping T off I got set to work, booked a semi-local hotel, set my alarm and got an early night. Woke up at 7am with the hardest morning glory I’ve had in a long time. Was tempted to have a wank but thought I’d save my cum for my sissy. Sent T a picture of my cock and he replied "Can’t wait Sir, I’m so excited but nervous". I didn’t reply. So I went out early to buy some supplies, went to the local adultstore to buy an enema kit, lube, lace thong and small butt plug. Sent him another pic of the contents of my bag to another similar reply from him..
Anyway, checked into the hotel at 3pm, sent him the details and told him to come straight to room 32, T arrived an hour later. 3 gentle knocks on the door, he’s here.
T looked cute, he wore a baggy jumper and skin tight black jeans with a pair of converse.
T "Hey, sorry I took so long, bus was late.."
I said nothing, gestured him to come in and as he walked past I closed the door and pushed him against the wall. Gave him a deep kiss and told him "from now you call me daddy". Whilst having my tongue in his mouth I grabbed his arse and lifted him so his legs were around my waist. Carried him straight to the bathroom and set him down.
Me (pointing to the enema kit) "do you know what this is for?"
T "Erm no"
Me (slapped him across his face at half strength) "No, what?"
T (he looked shook, wide eyed and on the verge of tears) "Er sorry, no daddy"
Me "Are you going to cry?"
T "no daddy"
I told him to undress, he did sheepishly then stood there with his hands covering his dick.
Me "put your hands on your side"
T "okay daddy" (he revealed the perfect sissy clit, shrivelled up and no bigger than an inch)
I led him into the shower, handed him a razor and shaving foam
Me "I don’t want to see a single hair on you from your eyebrows down, this is an enema kit, fill it up with water, put it up your arse, squeeze and push the water out, repeat until the water you push out is crystal clear. Understood?"
T "yes daddy"
Me "use the moisturiser there after you’re done and put this thong on"
T "okay daddy"
I left him to it, went onto the bed and sat back, watching some TV and having a drink. I was on the phone looking out the window when I felt a tap on my shoulder, turned around to see my sissy looking good enough to eat, all smooth and shining in the light wearing a tiny pink thong and a small vest. I put the phone down right away to admire my sissy.
T "how do I look daddy?" (stood there one foot over the other with his hands over his clit)
Me "how do you feel?"
T "amazing, just like a girl daddy"
Me "good. Turn around"
T (turned around to reveal his cute smooth sissy arse)
Me (I put my hand on the back of his neck and ushered him down to bend over. Tiny thong running over his tight arse hole. I ran my tongue up and licked it through the thong to a loud moan coming from T and a hole pulsing on my tongue, ready to be stretched)
T "that felt so good daddy"
Pulled him up and had my left hand around his neck whilst my right ran down his smooth soft body until it reached his clit. Kissed his neck from the side and cupped his already hard but tiny clit. Groped it through the thong until the tip popped out through the side. Couldn’t have been more than 4 inches. Ran my fingers down and under the thong and teased his hole. T was breathing heavily, biting his lip and gently moaning. Slipped my middle finger in and starting to slowly go deep, the more he moaned the more I pushed in, the tight moist hole had my cock hard and digging it’s way out of my boxers. I put my left arm around his chest and lifted him up, still fingering his hole and carried him to the tall mirror so he could see himself.
Me "look at what you are now. A worthless sissy. I own you" (slipped a second finger in and started to fuck him more and more vigorously) "look into your eyes as I finger you, this is what you were born to be. You are nothing but a mouth and an arsehole for my cock. You’re my faggot. Let me hear you say it"
T (moaning quite loud now) "yes daddy, I’m yours, always. I’m your faggot. Anything for you daddy"
Me (I pulled out my 2 fingers and put them straight in his mouth and like a good sissy he sucked like a hungry slut. I then yanked them out and sucked the juices myself before giving him a deep kiss)
I don’t know about you guys but I love the taste of a young sissy’s arse
He had his arms around my neck kissing me back, I pushed him onto the bed and pounced. Threw him to the top of the bed, pulled the thongs off and pushed his legs back behind his head. Was time to eat that tiny tight hole. Kissing it, licking it, sucking it and then tongue fucking it. The moans coming from T were a beautiful sound. I noticed his pre cum running down his thigh and so I sucked that up and his juices, leant up and spit it all in his mouth and kissed my sissy some more. I finally undressed too and my cock sprang up raging hard pointing straight to his face. I gestured to him and he didn’t need a second invite to come suck my cock like the good sissy he is becoming. On his knees sucking my cock whilst my hands reach round and spank his arse. I leant over to the bedside table and got the small butt plug I bought earlier that day. His eyes lit up as I directed it in his mouth, sucked it instantly. I got the lube and used a small amount on it then told him to keep sucking my cock. The moan coming out of T whilst I was pushing in that tiny plug was the loudest I had ever heard him. But before I pushed the whole thing in I stopped as I wanted my cock to stretch him and not a toy..
So I put him on his back, legs on my shoulder and applied a small amount of lube on my cock. My tip teasing his hole, his eyes looking up at me with wonder, I readied my cock on his hole and whilst he thought I was leaning in to kiss him I stroked my cock in. "omg omg, oh fuck" that’s all he was saying, I leant in and held him, the feeling of taking a sissy’s virginity is wonderful, to make them realise they were born to be fucked. Giving them real pleasure, whilst pleasing myself too of course. His tight hole gripping my cock as it slithers in and out, my strokes getting more fast, more deep.. I put his hand on his clit and we both wanked it together. My cock pounding his tight hole and his clit on the verge of cumming. As soon as I heard "omg I’m gonna cum" I took his hand off and flipped him over and fucked him doggystyle.. Pulled my phone out and captured a video **video of this will be uploaded**.. I’d love to say I lasted an hour but after a few minutes I had cum deep in his arse as every first time should end for a sissy.. I sucked out my cum from his arse and spat it in his mouth to swallow. He did. It was then I noticed he had already cum, without my permission, I knew I would have to punish him for this but I let it slide till another day (details of punishment in part 3)
We then chilled, drank and I fucked him again soon after. When I was done, I told him to leave. I had no interest in him after I was done using him. He took the thong with him but I kept the plug for now.
*************
That was the day my sissy became mine. This was only the beginning though. I’ll look at the feedback before writing part 3 at a later date, it will be about how I played with him in the office and trained him. This may not be the most well written or graphic but it is completely true unlike many on here. Excuse any spelling mistakes, if any, I’ve had a long weekend.
Video will be uploaded shortly, I will put the password in the comments section when it is uploaded