Daddy's Sissyboy

by Rainsky

7 Jan 2019 10424 readers Score 8.9 (49 votes) PDF Mobi ePub Txt


LENNY'S PoV/

My dad had acted a little strange the last few day's and I had started to wonder why. At first I gave it no thought, thinking it might be something about work but this long. There had to be something else. The thing that made me think the most was when he told me he had taken a month of work. He had never taken a day of in his life so this was really odd. Not that I minded him being home but the fact that I had started to feel the urge again could be dangerous with him in the house. It had been a week since the last time and a whole week he had been acting strange.

It was a Monday, I sat at the kitchen table this morning as always looking through the paper hoping to find a job. No luck this time either. It rang on the door. There as I opened it the postman stood with a package, I signed for it seeing it was for me. I have not order anything. I went up to my room sat down on my bed and looked at the box closely not seeing a return address. I found it strange, still deciding to open it. 

I gasped seeing what was in it, I lifted it in the strings. It was a really sexy and expansive underwear set. Under it a vibrating buttplug. That was not all for I found a note. Reading it I gasped again. 

I saw you and if you don't want anybody to know wear this and use the buttplug, it is remotely activated and I will use it after midnight tonight. 

I was scared yet the sight of the underwear and vibrator made my cock twitch. This sent me over the edge knowing even if my father was home I had to use this and I had to release. Night could not come fast enough. Midnight came. I took a peak so as to see that my dad had fallen asleep, he had and I was about to burst. I ran back to my room closed the door. I stripped of my clothing, to slip on the expensive, luxurious red underwear. My cock was already hard as hell, throbbing and oozing out precum. I took my bottle of lube and the buttplug. Went to my bed and placed myself on all fours. 

I started with touching my hard cock just rubbing my hand against it, moaning already and feeling so horny I let my head fall into the bed I needed both hands. I continued rubbing my cock with one hand the other one had started to touch my ass, I teased my hole outside the lingerie. After a minute I slipped the bottom half down, almost pulling them down to my knees. I took the lube and let some squirt out down my cheeks down to my hole, hitting the mark I shoved a finger inside me letting out a huge moan. 

Ahhhhh! Dad!

I slowly let a second finger inside me and moaned again. I felt my cock twitch letting out more precum, I moved the fingers in and out, the repeating it faster and faster. I was ready. I took more lube to my hole then I grabbed the buttplug. I slowly let its rounded tip enter me, going in I felt it getting bigger and bigger. A last push and I moaned for its biggest part hit my spot perfect, I did not even have to move it. Just as I was about to do it, it started to vibrate. Just a little. 

Oh yes daddy! Escaped my lips. 

I grabbed the sheets in a fist feeling the sensation. I Loved it, feeling my spot being stimulated. I was about to touch my cock as it turned up in vibrating power. I turned around laying on my back, grabbing the pillow and biting my lip. I moaned so loudly, hoping that my father did not wake up. I knew he was a sound sleeper but still. I was worried yet the thought of him hearing or seeing me turned me on so much. 

OOOO! Father! 

The vibrating speed and intensity got higher and I felt my cock twitch to its movement. My cock had sprung out from the underwear, red and thick it leaked precum. I felt like I was being milked. The vibrating speed got turned up again. I almost crumbled up into fetal position as I moaned feeling the tension build up. I felt myself shake. My cock Twitched again and as I moaned 

FUCK ME DADDY !

I came so hard, not touching my cock at all. It flew so high and some hit my face. I laid there feeling the vibrator still on but only a second after it got turned off. I laid there panting, catching my breath. 

BEN'S PoV/

I had tried to act normal but I knew he had noticed I had been acting a bit strange. He sat there reading the paper as he did every Monday morning. I found it a turn on, well I did now. Fantasizing all the time about him. Seeing him in a fifths dress like a housewife making dinner. I felt my cock twitch. I took a deep breath. I went up to take a shower, hearing the door bell ringing. I saw Lenny going to get it and continued walking up the stairs. 

In the shower I started to touch myself knowing that I would burst without even touching it if I did not. I felt like a teenager again. I had been jerking off two to three times a day since I had seen him. I was so fucking horny for him. The shame just made me hornier. I wanted my son so bad. I touched my cock, letting my fist in a tight movement rub on its head. I milked it. Moaning yet never his name trying to be careful so not to get caught. I Switched from milking the head to moving along the whole shaft of my almost nine inch cock. It was hard and thick. Precum running out I felt it burst and could not help a huge grunt leave my lips. 

I went about my day as usual, Cleaning but also relaxing. I had taken a month of work having almost a six month in vacation time to take out. I needed this time for all the thoughts in my head made me crazy. I had to let them take its course so they stopped, but at other times I thought I needed to feel my cock inside him for it to stop. Other times I dreamed about us living happily ever after. Just so many thoughts. 

Night came and I went to bed. Hard like all night before. The clock had just struck midnight when I heard my door open, I did not turn around knowing it was Lenny and I did not want him to see my raging hardon. He closed the door. I got up the bed feeling the urge to see what he was up to. I stood outside his door now touching the bulge in my boxers. I really needed to see him. I heard his moaning and thought it to be a good cover to open his door just a little. There I saw him, which made me smile. He had gotten it. He got my gift today so the postman was the one who had rung the door this morning. He looked so hot in the lingerie I had bought him. He looked hot always but seeing him so slutty. Being a sissy craving my cock made me so hard. I pulled down my boxers seeing him starting to finger his ass. Hearing him saying dad I started to rub my engorged stick. It already leaked. I took the precum rubbing all over using it as lube. I saw him enter an other finger. I loved to see him play with his little tight hole. 

He stopped to grab the buttplug I had given him, I ran to my room to get my phone already had I installed the app to turn the vibrating function on. He let it enter him and he moaned louder. I turned on the vibrator once it was in just as he was about to touch his cock. He did not he moaned and I started to jerk my cock again. Hearing him utter daddy and dad even father made me drip. That was hardest during the day for hearing him all day saying dad drove me nuts. I turned up the speed of the vibrator and saw him fall onto his back. I pumped my cock into my hand now letting myself saying his name. 

Oh Lenny my sissy son. 

I pumped my fist wishing it was his ass. I increased the speed on my movement and the speed of the buttplug vibrations. I knew he would soon cum, I wanted to cum with him I only wished it was in him. I saw him laying there not touching his cock, it oozed out so much precum. His cock throbbed so bad. I heard him moan a last time so loud and I did the same almost screaming. 

OOOO LENNY!

I shoot my load hard it flew over tree meters across the hall almost hitting the wall. I loved seeing him. I turned of the buttplug seeing him laying there catching his breath I knew I needed to clean up and go back to bed.  

The morning came and I knew after last night I had to have him. I needed to fill his inside. I wanted him so bad. Something else had started to come over me, was this really just lust or could this be love. Romantic love. I need a plan I need to get this to happen soon so I can truly know what I feel, is it just lust or... 

To be continued.

by Rainsky

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