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Sissy Son

The day had been a long, hard one at the office and I simply couldn’t wait to relax and enjoy some dinner with my son. I wanted to surprise James with some extra time as I’d begun to realize just how disconnected we had become, the divorce not helping matters. Certainly my ex-wife had told me what a horrible father I’d been when she left with our daughter to shack up with some guy in New Jersey. But James had remained with me as he was graduating and didn’t want to have to readjust to a new school for a few months.

So, I had taken to doing what I could by shoving 18 years of poor fathering into a few weeks we had alone together. But he’d been resistant hiding away in his room and playing on the computer all the time. I loved him with all my heart but he worried me the way he was going and I was determined to break him out of it.

I had stopped off at our favorite pizza place after leaving work early and parked in the driveway instead of opening the garage and pulling in so I could slip around back. With pizza box in hand, the house was quiet as I slipped into the side door that led into the kitchen. It was strange as school was on break and James should have been home by now. “He’s probably playing on that damn computer,” I muttered to myself, setting the pizza on the counter.

Slipping off my dress shoes, I left them by the foot of the stairs like I always did, a habit of being yelled at too many times for tracking dirt on the rugs. My socked feet padded up the tight, wooden stairs and into the main hallway that ran from the master bedroom down past the bathroom and the c***dren’s rooms. I heard the light music playing as I moved down the hallway, some female singer I didn’t recognize, and a strange voice over the lyrics. It was high pitched but with a hint of a croaky baritone underneath.

Reaching for the doorknob, I threw open my son’s door and nearly stumbled over my feet at the sight. A young woman was standing there dancing to the music in a dress I recognized as one my daughter had use to wear. Shapely long legs were clad in black nylons and ran into strappy high heels that hit at my weakness for a good pair of legs. Short, wavy brown hair ran into her eyes as they turned to me, shocked recognition showing in those whiskey colored eyes. And then it hit me, the attractive woman I was staring at, and whose legs had provoked a response, was my son.

I stopped in mid apology thinking I had at first walked in on a girlfriend of my son. He bent over as his knees came together and his hands tried to cover his body as if he’d been discovered naked. Despite bending over, I’d already seen the erection poking at the front of his dress even as he tried to hide it. My son was dressed up like a woman and aroused by it. For a moment, it felt like my world was crashing down and I staggered to his bed and sat down as he moved away towards the wall, our eyes still looking at one another.

“You… you ok, dad,” the voice of my son asked from the lovely female figure.

“How long,” I asked, my eyes looking up and down him. I patted the spot next to me for him to sit as I tried to pull my rational brain to the forefront. From the way he looked, there was no way this was his first time dressing up.

“For a while,” he said, moving to sit next to me. He sat down and crossed his legs like a woman, putting those lovely stocking clad curves on display for me. “I’ve been dressing up just a little for years now but only seriously like this for about two.”

Two years. An irrational part of me began to get angry that he felt he had to hide this from me, shutting me out of much of his life. And a part of me was angry because I’d raised someone who wanted to dress up like a girl. I began to think about all the bad things I’d seen online and wondered if he was going down to glory holes and sucking men off, being a little tramp. Still, he was my son and I tried to keep calm. “Is this because of me… not being around all the time?”

“Jesus, dad,” he spat, rolling his eyes. “Not everything is about you. It just feels… I don’t know… right.”

Suddenly, I was standing up and moved in front of my son, towering over him. Well, ‘her’ really wasn’t it. My hand reached down and fingers wrapped around the back of her neck, forcing her to look up at me, a snarl showing on my face. I could see a hint of fear in her face and something else, something I knew was as wrong as she did. Her skin felt good under my fingers, warm, and it had been a long time since I’d been with anyone. “Don’t talk to your father like that, missy,” I said, my voice low and rumbling.

We looked at each other for a moment as she licked her red lips which provoked a response in my, a bulge growing in my trousers. “So, do you just like dressing as a woman or are you one?”

“I… I don’t know,” she stammered, her voice rising in octaves.

“Well,” I said, taking a deep breath. I needed relief and she needed to know, and then needed to be trained if it was what she wanted. “We should find out. If you are, that will make you the woman of the house with a great deal of responsibilities.” I swallowed hard as I watched her looking at the outline of my cock in my pants, pressing against the fabric with growing need. “Take it out.”

Her hands moved up as fingers began to work open my belt and unzip my pants, pulling them down my legs. As she did, her head brushed across the front of my boxers and my hidden erection causing me to gasp. It had been a long time. A smile was on her lips as she slipped her fingers into the waistband of the underwear and slowly pulled them down for the reveal, her gaze intense on the prize.

My cock sprang out and nearly slapped my stomach it was so hard. Once free, it hung at a gentle slope as if begging to be slid down her throat. The bulbous head was red with a little tinge of purple near the rim of the helmet so great was my need. A glistening smudge on the tip showed how excited I’d grown seeing her fully dressed up, a fact that seemed to please my sweet son to no end as she stared at it. It bobbed with each pulse as I looked down on her, eyes lingering on her lovely legs.

Her fingers reached out tentatively and brushed along the shaft but a hint of hesitancy showed in her body. The grip I held on her neck grew tighter as I drew her forward until her lips touched the tip of my raging hard on. “You know what you truly are,” I said, my voice husky with desire. “You are daddy’s little slut, don’t try to pretend now. You got daddy all hard now you need to take care of it. Get to work baby.”

Looking up at me, her fingers slid around my shaft near the base until she was gripping me though her fingers didn’t touch. As she did. Her lips parted and her tongue snaked out and tentatively lapped at the large head. She swirled it around the helmet and played her tongue over the slit at the tip, making a murmuring sound as she got the first taste of my juices. Then, her lips parted and slid down over the rip of my helmet sealing my cock in my darling girl’s mouth.

I moaned as I felt her mouth wrapping around my shaft and began to slide up and down slowly, her tongue bathing the bottom. As she did, her one hand began to move up and down my shaft while her other hand cupped my balls, fingers playing with them and gently massaging them. It provoked another moan as none of the women I’d been with in the past had ever done that and I found it to be extremely provoking. My body swayed as I stood there and watched my son, dressed up like a woman, sucking on my cock like an eager new girl, the shaft glistening with her saliva.

“Oh,” I called out, “you are such a good girl, Jamie. I knew when I saw you this was what we both needed.” My fingers caressed the back of her head as my hips began to move, thrusting more of my cock into her mouth. Suddenly, I felt the head of my cock nudging at the back of her mouth, figuring that was in and not ready to teach my little girl deepthroating tonight. But then, I felt her swallow and suddenly her lips were going lower as I slid into her throat. As her lips pressed around the base of my cock, I realized my sweet cock sucker had been practicing.

I groaned loudly as I felt her tongue brushing over my balls with my cock wedged into her throat before she pulled back. Her lovely eyes looked up at me with a new gleam in them as trails of saliva clung from her lips to my cock, the head still on her tongue. We’d both found something tonight I realized as she began to move up and down my shaft while I thrust deep into her, moving in rhythm together. She pressed her tongue up as she moved over my sensitive glans and I knew I wouldn’t be able to hold back for long. The bad relationship with her mother and the divorce had kept my sex life at a minimum.

“Oh, baby,” I moaned, feeling my cock swelling. My sac drew up in her hands as she looked up at me, pulling back so only the head was in her lips, her tongue bathing it, as her hand slid up and down furiously, as if begging for my load. A cried out as I felt the first jets burst out from the tip strongly, flooding my darling’s mouth. I saw her flinch on the first few shots but quickly began to swallow as I filled her mouth to overflowing, little trails of translucent white dripping out the sides of her mouth and over her chin. I continued to pulse more and more into her as her hand kept moving languidly up and down the shaft, milking me as her tongue lapped at the tip to get every drop.

She smiled up at me with cum still on her chin and a little residue on her tongue and lips, her eyes bright and happy. “Thank you, Daddy,” she said, almost giddily.

I looked down at my beautiful sissy son looking so sexy in his s****r’s dress and nylons, ripe and ready. My cock was already hardening as I held my Jamie and began to slap my erection against her cheek and lips. Little streams of cum and saliva clung to her skin and trailed to the tip of my dick. I had just orgasmed unlike I ever had in a long time thanks to my new beautiful girl and it sent my mind racing with ideas. “Stand up,” I suddenly said, pulling her to her feet.

Once she was up, it was easy to see my little darling was as excited as I was with her cock pushing out against her panties and dress. I reached out and touched the bulge and she moaned deep in her throat like some wanton whore. My eyes narrowed as I realized how close she was but I knew I had to take care with her unless she became a selfish bitch like her mother.

“Take your dress off,” I said, moving to sit on the bed.

She nodded her head and rose to take a few steps away from where I sat, pirouetted around to smile at me. Then, she unbuttoned the dress enough to be able to slip it off of her, careful of the wig on top of her head. She stood there before me clad only in a pair of matching black panties and bra with lovely black nylons held up by a garter belt. Her panties were rudely distended and the head of her little cock peaked out from beneath her panties.

I leaned stood and reached out and took her hand in mine before heading out of the room. I held her tight as I lead her down the hallway and into the master bedroom, leading her over to my bedside. Sitting down, I opened a drawer and pulled out a few old laces as my other hand grabbed my son’s hip and pulled her close. Slipping my fingers under the waistband of the panties, I pulled them down releasing her straining erection, drawing the strip of lace cloth down to her knees.

“From now on, there will be no secrets in this house,” I said determinedly, looking up at her. “You will be Jamie the minute you come into this house. You will be my little sissy slut, doing anything and everything to please your daddy. And you will be rewarded when I say it is ok and not a moment before. You can start letting your hair grow as well as I want to be able to grab onto those lovely locks. Do we understand?”

She nodded but there was a mixture of confusion, joy and worry in her eyes. It was obvious she wanted this but wasn’t sure she was ready for all of this, it was a lot even if it was all she ever wanted. Plus, that he was her father probably was a worry going forward. But, determination showed in her features as well knowing she’d do anything to get to be Jamie more and more instead of James.

Reaching out, his fingers roughly wrapped around his son’s balls and stretched them down away from his body. Coiling the laces around his sac near the base of his hard on, he quickly tied off his testicles to make it painful, if not impossible, to draw up and allow him release. To help the control along, he tied a lace around the base of his cock so his little erection swelled even bigger and the head turned red. Giving it a pat on the head, he reached back into the draw and pulled out a small tube of lube as he rose to his feet.

“I think you are ready to become a true girl, son,” I said, reaching out to stroke a finger down his jaw. I loved him so much but this brought it to a whole new level, knowing he would be mine like no other ever had him. He’d be my little girl, my sweet slut, and do everything to please me, pleasing himself in the process. “Pull your panties off fully and get on your hands and knees.”

I watched the trepidation on his face at the thought of getting a real cock up his ass, obviously he’d never taken one from the look. But he wanted it, I could see that too. He wanted to be fully my little sissy and take me deep inside of him. He slowly walked over to the bed and crawled onto it, thoughtful enough to keep her heels on as he got onto her hands and knees in the center of the bed. Her sweet, plump ass looked so good sticking up in the air, my cock jumped as I moved towards him.

Carefully squirting a bit of lube in between the cheeks of his ass, I rubbed it around the tight ring and massaged it into it. I decided to forgo with using my fingers to loosen him up, I had a feeling he’d probably used some toys in that area from the look of it. Instead, I knelt behind Jamie and placed the head of my cock between her plump cheeks, squirting more lube onto my head and shaft.

With a gentle, steady pressure, I fought against the tight muscles of her anus as I watched my sweet sissy son try to relax but too nervous. I leaned into him and the resistance suddenly gave and my head sunk into him, the tight muscles closing around the rim of my helmet. She moaned softly as I groaned quietly, enjoying the first slick warmth of the inside of my darling son. I held myself inside of her with my cock sticking out so rudely from between her cheeks as I added a little more lube around the shaft.

Then, placing my hands on either hip, I began to gently rock myself in and out of my baby with breathy grunts of pleasure. She moaned and groaned in a mixture of pleasure and pain as her fingers clenched at the sheets. My fingers dug into her fleshy ass to pull her back as I thrust up into her, setting a timing that helped to push me faster into her. I wanted to feel myself so deep inside my darling sissy and fill her with my cock, knowing she would be wrapped around there as much as I wanted.

Looking down, it was vivacious how her ass stretched around my thick cock, a lewd show only for me. “That’s it, my sissy,” I croaked. “Take all of daddy’s cock deep inside of you. You are daddy’s slut, aren’t you?”

“Yes,” came the strained reply. Her body moved and writhed on the bed with each thrust into her virgin ass, taken for the first time by a real man. Her wet, red lips were parted in a constant gasp, cum still flecking them from the earlier blowjob. Every inch of her body was on fire and strained with need as all thought fled from her head leaving only the need, the desire. She needed her daddy to take her fully, to be his and please him as a woman should, like her mom never could.

And then, my crotch ground into the tender flesh of her ass as his balls rested against hers, buried completing inside of his sissy son. My fingers pressed into her ass before giving them a squeeze. “Good girl,” I murmured. “You took all of daddy’s cock proving what a good slut you are.”

I didn’t let her rest too long as I lay inside of her, my hips soon moving again. The tight warmth of my slutty girl urged me on and held me so snug I wasn’t sure how long I could hold on despite my earlier release. We set up a steady rhythm with me pressing forward deep into Jamie and her pressing back against me. I would pull out about half way before slamming quickly back into her but occasionally, I would pull almost all the way out until only my head was inside of her and then slam back home hard. The wet slapping of our groins and sacs together soon filled the room along with wanton moans of my sissy son and my own grunts.

Looking over to the side, I watched myself fucking my son dressed up like a girl in the mirror on the wall. I watched how my cock slid out slick with lube from between his spread cheeks before both of us slammed back in as if we couldn’t be parted. I watched how his head twisted and, lips parted, turned with a constant moan, his brow furrowed with the pain and pleasure. His girlish body rippled with pleasure as he threw himself back, his cock flopping below him, looking like the perfect slut. It was hard to imagine the boy beneath as he looked so damn feminine being fucked in only a garter belt and bra and heels.

Soon, the tight, massaging grip of my sweet sissy grew too much as we pounded against one another, her cheeks growing red with each slap of our bodies. Her pale skin was so lovely and smooth against me as I bent over her, our slick bodies pressing against one another like lovers as I pounded without care or concern into her. I reached my arms around her hand held her tight as my mouth kissed and bit at her neck and shoulders, panting into her ear.

I felt my balls draw up as the tightness of the grip on my cock grew tighter as it expanded inside readying to fill her up. And then I cried out as my body pounded against hers, wiggling against her as if trying to milk every last drop into her. My cock pulsed inside of her as I felt it splatter deep into her bowels and coat the passage around my cock, letting me slid even faster in and out of her. I felt like I could keep coming and coming with the pleasure my darling son’s ass gave me, filling it up until I was sure it was going to explode out.

Laying against her for a moment, I finally rose up so I could look at the sight of my satisfied cock still in her ass, knowing it was full of my seed. Then, I slowly let it slip out with a wet splotch, a thin trail of cum and lube clinging to my cock and her anus. A few moments after I pulled out, I watched some of my cum began to leak from her abused hole, my little sissy slut still kneeling there, panting with pleasure. “Clean up,” I said, giving her a small swat on the ass. “I don’t want cum on my sheets.”

Updated: October 21, 2016 — 1:08 pm

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