tagTransgender & CrossdressersNeighbors Sissy Son

Neighbors Sissy Son

bynewfield1981©

About two months ago a woman and her son moved into the vacant apartment next to mine. I noticed right away how effeminate the son was, even though he was dressed like any other 18yr old boy, he couldn't have weighed more than 115lbs and his facial features were soft and delicate! Having a thing for femboys (twinks) I set my sights on this one!

Since I work from home I know most of my neighbors schedules and the boys mother would head out around 8am and not return until 7 or 8pm! It being summer the boy would have the place to himself all day!

I decided to test the waters one morning after seeing the mom leave. I didn't have an exact plan except to introduce myself and see where it goes from there.

I was a little surprised when a young lady opened the door! Could it be the woman had a daughter as well as a son? Then it hit me this was the sissy son in drag! I must say he/ she was very cute! She had on a very short cocktail dress as in if it was any shorter I would be able to see her cock and her tail.

Her lips had a light amount of lipstick and a good amount of lip gloss, which had the intended effect of making me want to stuff her mouth full of cock meat.

I guess she saw the recognition in my eyes and began to panic. I took full advantage of the situation. 'Does your mother know you dress like this when she's at work?' I asked as I walked in like I owned the place. I figured now was the best time to assert my dominance while he/she was off balance.

'No, please don't tell her mister.'

'Daddy! It's Daddy when we're alone! And Sir every other time!'

'You want me to call you Daddy? Why would I do that? I think you shou...'

SMACK right across her face and I grabbed her by the throat. 'If you don't learn to obey your new daddy then I'm just going to have

to expose you to your mother and anyone else I can think of!' I think this got her attention because her look went from defiance to defeat in seconds.

'Yes si...Daddy!'

Very good this was working out better than I hoped! I mean what was the kid gonna do? It wasn't like he/she had much of a choice. With this I closed the door walked over to the couch, sat down and called my new slut over.

'Get the fuck over here slut!'

This must have played right into some of the sissy's fantasy's because "she" came right over and assumed the position, hands behind the back and head bowed! I knew it, a natural submissive!

'Have you ever sucked cock before?' I asked.

'Yes Daddy, I have a friend like me and we practice on each other.'

'Well now you'll practice on me. On your knees slut, show me what you've learned so far'!

I was already hard watching her delicate hands fumble with my zipper. When she finally got my fat cock out I was amazed at how much bigger It looked in her little hands. She started stroking me and I could see how mesmerized she was watching my foreskin slide back and forth over my angry cock head.

'What are you waiting for? Start sucking and make it sloppy, I expect sloppy head from my sluts!'

Just before the sissy swallowed my throbbing cock meat I heard her mumble, 'Fuck yea!'

She starts off slowly but then her lust for Daddycock makes her more aggressive. I feel the back of her throat with the swollen head of my cock and think there's no way she going to go further. I've got about six inches of my cock in her mouth so I was impressed!

For someone this young she must get alot of practice.

'Does your friend have a cock as long and as thick as mine?' She took her time coming off my cock like she was afraid she'd never get it back. When she finally released my wet cock, she did so with an audible pop!

'No daddy, your cock is twice as long and three times as thick!" She said as she stroked my slippery cock. 'But I have a dildo thats the same size just not as thick.' She said with obvious admiration as she couldn't take her eyes off my cock meat. 'So it seems you like it when my thick cock is knocking at your throat's door.'

'Yesssssss.' she said in an almost dream like state, never taking her eyes off the glistening meat pole inches in front of her face patiently waiting for permission to put it back.

'Go ahead put it back in that sexy mouth of yours only this time try and swallow the whole thing'.

'Yes daddy, thank you.' was all she said before sucking me back into her mouth. And with a new found purpose she forced another inch into her mouth. And then it happened, I felt the thick head of my cock pop into her throat and she froze.

Holding there afraid to take more but even more afraid to pull it back out. I offered my assistance in the form of two hands on the back of her head slowly applying pressure. It didn't take long before I felt her nose in my pubic hair. I held her there for a moment simply because it felt great to have my whole thick nine inch cock in this young boys tight throat!

When I did let go I was surprised to see she stayed down a little bit longer before finally coming up for air! She didn't stay up for very long before diving back onto my pulsing cock. This time taking all nine inches at once. She milked my cock with her throat muscles and I knew I wasn't far from cumming. So I leaned back and let her have it.

I was lifting my ass up off the couch in time to her downward motion. I wasn't going to last much longer so I grabbed her hair with both hands and held her down as I felt my orgasm rising up my shaft. I saw stars when I finally came and I came alot 4,5,6...7 long ropes of cum down her throat but I wanted to mark her as my pet, my fuck toy, my cum slut so I pulled out of that warm tight throat to finish on her face.

Two long thick ropes of cum hit her in the forehead and cheek. Breathing heavy with my cum running down her face she couldn't have looked more beautiful.

With her fingers she scooped up the cum into her mouth and asked 'Did i do good daddy?'

'Yes my slut you made Daddy very proud of you, but don't think your training is over, it's just begun! Tomorrow we begin your anal training. I'm going to turn that tight little ass of yours into a proper boy pussy!'

After that first day forcing my thick 9 inch cock down her throat and painting her face with my hot sticky cum, I left her with instructions to get that asspussy ready for me to use. Everyday she would text me selfies of her with either butt plugs of various size or various dildos.

Her favorite was an inflatable 10 inch rubber cock that starts out at 2 inches thick and expands to 3 and a half in. She even mounted a dildo on the wall with a click counter to count off every full insertion.

I really get off on owning this fucktoy and make no mistakes about it I owned this slut! Establishing myself as her dominant Daddy figure wasn't hard to do, the little cum slut has been gagging for it since "he" decided to choose cock over pussy and became "she"! And thats the key, my cock makes "him" feel more like a "her" than all the slutty dresses, thongs, stockings or high heels combined!

I was looking through the peep hole waiting for my neighbor to head to work so I could go over and use her son, then the their door opened and the mom walked out wearing a tight grey pencil skirt and silky white blouse that did little to hide the lacy white bra underneath! Nice, I think I'm going to have to work my magic on the lonely single mom next, right now it's one slut at a time but how convenient would it be having the both of them under the same roof.

I waited another ten minutes to make sure the mom didn't double back and went next door to see my little fucktoy.

Not long after I knocked the door swung open and my pet was standing there in what can only be described as a Little princess pink babydoll complete with unicorns and stars. My god she was even holding a teddy bear in her arms!

'Come in Daddy, I've missed you so much' she squealed like a pre-teen girl. My cock responded immediately. She doesn't realize the dark forces she's playing with, so I shut the door behind me grabbed her by the throat and kissed her hard. With my tongue exploring her sweet mouth my free hand went to the back of the panties and slipped inside to find that juicy little asspussy I was going to gap today.

When my fingers found her hole two of them worked their way to the first knuckle earning a sweet moan from my little slut.

'Mmmmnnngg, yes Daddy fuck me with your long fingers nnnggghhh.'

But I needed more so I grabbed her by the hair and dragged her to the end of the hall where the bedrooms were.

From behind her but close enough for her to feel me grind my cock on the ass that I just had my fingers buried in I asked which room was her mothers. Pointing at the door on the left she pleaded with me to take her to her room. But I wanted to establish that upsetting me was worse the upsetting her mother plus I knew one day I'd be fucking them both, together in this very room.

Still pressed up against her sweet ass I said 'We fuck where I say we fuck' and with this I pushed her through the door and onto the neatly made bed.

'On all fours and face me' I ordered. Once in position her face was inches from my hard thick cock just behind the zipper. Without any suggesting on my part she began rubbing her face on my bulge, giving it little kisses and then back to rubbing her face there like a... kitten!

'I think I'll call you Kitten from now on. I mean I'll still call you slut, fucktoy, sissy, and many other names but Kitten will be your main name!'

She stopped just long enough to say "I love it Daddy! I'll be your slut kitten".

When she went back to rubbing up against my cock again I asked 'Does my Kitten want to suck Daddies big fat cock in her mommies bed?' I added the last part to reinforced the taboo factor. She needed to learn sex with me wasn't going to be vanilla. I was here to push buttons.

'Yes Daddy I love your fat juicy Daddycock so much. I think about it all day in school it gets me so hot that when the bell rings I run to the restroom to play with the plug in my boypussy imagining it's you inside me. And my little clitty squirts cummies all over' she said as I watched her left hand go down between her legs to play with her stiff little four inch cocklet.

I undo my belt and pants then tell her to take out my cock and get started. By now I'm fully hard from all the face rubbing, so when she pulls out my cock I'm leaking pre-cum like a faucet. Seeing this she moved in mouth open but I grab her by her hair and stop her saying 'Beg for it slut'.

'Oh Daddy please let me suck your big fat daddycock, I need it sooo bad. The way you force it down my throat and hold it there till I think I'm going to pass out. Nnnggghh it feels so good.'

At this I take my cockmeat and slap her in the face a few times pre-cum splashing all over her.

'Yes Daddy punish me, I've been a bad kittenslut.' By now she was yanking the butt plug in and of her analpussy 'Sucking big fat cock right here on my mommies bed nnnggghh I'm such a bad kittenslut nnnggghh oh Daddy please let me suck it.'

I lower my cock lining it up with her lips and run it across applying cock juice like lipstick. Still holding her by her hair I now feed her the first 5 inches of cockmeat. With the tip of my pole I feel the entrance to her throat and pause. I bring my left hand up to join my right hand at the back of her head, not to force her to take more but to keep her from backing off my pulsing cock.

Thats when I start little short strokes while she sucks like her life depended on it. After about 5 minutes of this my pet begins her assault on the base of my cock knowing the only way to get there is by swallowing the whole 9 inches of my fat cock! Feeling that tight wet warmth around my entire cock almost made me cum too soon. So I pulled out and said 'Turn around and plant your face on the bed, I want that asscunt now.'

This presents me with a view of that sweet little ass with her little balls peeking out the gusset. I grab the panties and with one swift pull I yank them from her body. Her squeal only fuels my desire to ravage her even more. Placing one palm on each cheek I spread her open and admire that asspussy up close.

Looking at her it's hard to tell she's been training it for the last two weeks. It looks so tight! I give it a lick from those tiny balls to her sexy little hole then plunge my tongue in as far as it will go earning me another squeal. After a minute or two of this I decided it was time I claimed my prize.

I grab my meaty cock at the base and tease her tight little boycunt with the swollen angry head half covered in foreskin.

'Nnnggghh yes Daddy give it to me nnnggghh I need it! Fuck me and make me a real girl. Nnnggghh fuck me and make me your whore! Fuck me and make me cum all over your big fat Daddycock! Nnnggghh.'

I was about 6 inch deep when I felt convolutions in her meat tunnel.

'Nnnggghh! Oh Daddy I'm cumming! Nnnggghh you're making me cum with your big fat cock in my tight little boycunt! Nnnggghh It feels so good! Harder please Daddy I need it, fuck me harder! Nnnggghh!'

I was now fucking her like my life depended on it. I was bottoming out with every thrust. My huge balls were smacking her much smaller ones!

'Ooohh gawd! I'm cumming again! You're making me squirt cummies all over mommies bed nnnggghh!'

I couldn't hold back any longer so I buried my shaft all the way in and let loose!

'Oh you fucking slut I'm cumming! Take it in your tight little boypussy you fucking whore!' I came so much it was squirting out her ass even though I was still inside.

'Oh Daddy' she said between gasps for breathe 'You bred me like a real girl!'

While she was saying this I was busy scooping up the anal creampie, I then reached around and fed it to her. When there was no more cum left to feed her she licked my fingers and my cock clean like a good girl!

'Did I do good Daddy?'

'Yes my Kitten you're a true cockslut for Daddy! Soon I'll be sharing you with a few of daddies friends!'

'Do they have big Daddy cocks like you?'

'I think so, some even bigger!'

'Bigger? I guess we'll have to keep practicing.'

'Every fuck day'

Thanks for reading I appreciate all feedback as I am a new writer and hope to get better.

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bynewfield1981© 13 comments/ 157244 views/ 203 favorites

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by Anonymous

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by Anonymous12/02/18

Great story!

This story was very well written, especially from the eyes of the sub. She sounds just like I want to be treated. Took the words right out of my mouth

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