Sissies don't Disappoint Daddy Pt. 04

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The Sissy Chronicles: Nicholas becomes Nikki.
3.4k words
4.7
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Part 4 of the 4 part series

Updated 08/01/2024
Created 07/30/2024
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This is a true story, as told to me by Nikki, one of my distant Sissy fans, and written in my own style. After she proofread it, I asked her if she liked the title, her reply was, "It is a perfect title. It is so true! Every sissy must strive to be the perfect fucktoy for Daddy. They exist only to please, and if they have any will of their own it should be laser focused on Daddy's needs."

I couldn't agree with her more...

-----------------------------

So,... where were we?... In the last part of my story, I told you about how my first Daddy took my sissy virginity. I'd been a sissy, and knew it, from the first moment I felt his eyes on me as I swam in his pool, a few blocks from the house where I grew up. I knew it from the thrill I felt when I saw the towel that covered him tent up from the pressure of his hard cock underneath.

I'd known it before, really, because of how different I was from my male friends. I'd known it when my little four inch clitty would get hard as a rock as I watched porn and imagined myself as the woman, all dressed in lingerie and heels, sexy and feminine, sucking those beautiful hard cocks and getting fucked in ten different positions.

I'd known it but not admitted it to myself until my parent's friend and neighbor Alex opened me up -- in more ways than one! -- and taught me the joys of being a woman inside a body mistakenly born as male.

After I sissygasmed for real the first time, squirting my gooey sissy mess all over the both of us and the bed, and Daddy emptied his big balls deep inside my pussy as he pounded my ass, he rolled off my slender little body, tired and spent.

I got up and went to the bathroom.

I looked in the mirror at myself and wondered if everyone else could see that I was a real sissy now. Of course my mascara was running from the tears, and I'd left most of my fuchsia lipstick on Daddy's big mancock. But did it show in my eyes, my smile, the way that I walked?

I had to get cleaned up and get home soon. I took the makeup off and found my panties. His seed was still leaking out of my pussy but I cleaned everything as best I could and kissed Daddy goodbye. He wanted me back soon, very soon!

I was going to make sure that happened. Sissies don't disappoint Daddy.

When I got home I tried to sneak in the back door but ran right into my mother. I was like a deer in the headlights. I knew she was going to realize I was a new Sissy that had just lost her virginity in some hot kinky trans sex with her much older neighbor, but miraculously she didn't seem to notice. She just asked me if I had a good time at Alex's pool.

I nodded and she told me what a good man he was for letting me come over anytime and play. I told her he was the best! I went upstairs to my room. I have to admit that Daddy had pounded my hole so hard walking up the stairs felt a little awkward but I don't think she noticed.

I got in the shower and washed the cum off and laid down in bed. I couldn't stop thinking of my Daddy; all the new feelings he had introduced me to, and the incredible sensations of the sex we'd just had. I thought of the gurl I was now. I was a sissy in love and I started to finger my hole wishing it was Daddy opening me again.

My clit strained and despite what seemed the quart of sissy cum I'd just spurted out only an hour ago I had to have release again. I stroked my little clitty and fingered my pussy and I came again, thinking of Daddy fucking me over and over. I drifted off to sleep a contented sissy.

In the days and weeks that followed, Alex and I tried to get together as much as possible. I was constantly horny for him. I wanted so badly to please him and I wanted the pleasure doing that would bring me as well. I constantly thought of his beautiful man cock, his kisses, his masculine body, and his love.

He often had to work late and I was in college now so we only had maybe a couple of times a week to satisfy each other's needs. On the days I could go to his house I made sure I was super clean and smooth.

He'd greet me at the door with a big hug, picking me up and carrying me inside, kissing me the entire time. Setting me down he'd smack my ass and tell me to hurry up and go get changed. I'd whimper and call him a brute and then sashay my cute little butt for him knowing his eyes were glued to it. I went to the bedroom and stripped out of my Nicholas clothes and put on whatever outfit he'd gotten for Nikki that day.

He bought me luxurious lingerie, heels, tiny little skirts that barely covered half my ass, tops, collars, expensive wigs, and toys. I carried my makeup hidden in my backpack. He liked me to look like a freshly fucked trollop before he fucked me, and he'd tell me I looked even sexier afterwards.

It was always such a relief to shed my boy clothes. Like wearing an uncomfortable suit, it felt so sexy to be finally free of it. Then I would prance back into the living room and pose and strut around for him. I loved watching the shape of his big cock grow under his shorts as he touched it while watching me!

Finally I'd sit on his lap as we smoked a bowl, and he'd explore my body with his hands and kiss my mouth, my neck, and my nipples.

It was like being in heaven. My body was on fire as he played with it any way he liked. My clit would get so hard, even without being touched, and when he played with it I felt like I would cum right then and there but I knew that was not allowed. Daddy's needs come first and a good sissy gets her pleasure by fulfilling them.

As he kissed me and I moaned back into his mouth I'd squirm until I could get into a position where I was able to reach and stroke his cock with my little hand. It was always hard when my hand got there and I thrilled as I traced its outlines through his shorts and teased it with my fingers the way I knew he liked it.

Soon I would slide off his lap and sink between his legs and look up at him with wide eyes while I licked my lips. "Please, Daddy, may I?" I'd ask.

"May you what, baby?" he'd tease me. "What do you want?" He loved it when I begged him for his cock and I swear I would beg him until the end of time if that's what it took for me to have it.

I'd gaze up into his eyes as if hypnotized, saying "Your big thick man cock, Daddy. I'm hungry! Please may I suck your cock, Daddy? Please!?"

He'd tease me again. "Have you been a good girl, Sweetheart?"

"No, Daddy," I'd reply. "I've been very naughty. I've been thinking about your big hard cock and how much I want to suck it and how much I want you to fuck me with it!"

"Have you cum since the last time I saw you, baby?" he'd always ask me, and I would reply, "No, Daddy, I'm not allowed to!" with a pout.

Of course sometimes I had. I just couldn't help it, and it always amazed me how much cum my little sissy clit and balls could produce; what a mess I could make. Luckily I was young, though, and could replenish my supply readily and he never could tell the difference.

Then our little game would continue. "I'm sorry, honey, what was it you wanted? Please remind me."

"Your cock, Daddy," I'd answer. "I want to suck your big, beautiful cock. Please, Daddy, may I suck your cock? I need it Daddy!"

And he'd finally relent. "Yes, baby, you may suck Daddy's cock. Pull my shorts down. He'd lift up on the couch and I'd pull his shorts down his strong, long legs, and off, and nestle between them as he opened up to give me access to my heart's desire.

I would kiss and lick my way up the inside of his thighs, finally arriving at his balls, where I stayed for while just lapping at the heavy sack. Finally I would grasp his cock and begin kissing and licking my way up and down the shaft, listening to him tell me what a good little sissy slut I was and how good it felt. I would tease him that way until he'd tell me, "Suck it now, baby! Suck Daddy's cock."

I'd guide it between my lips and lower them down the length of his hard cock and back up again. It always felt so good to have it in my mouth; thick and warm - soft, yet so very hard. I'd savor the taste and feel of his cock in my mouth and moan like a slut as I tasted his precum and tongue lashed his cockhead and that oh so sensitive area on the underside of the shaft he liked so much.

Soon Daddy's needs would overwhelm him and he'd start to face fuck me. I loved that part the most. It meant that I was pleasing him so much he couldn't control himself! If we had enough time he'd pick me up and take me to the bedroom. Literally, throwing me on the bed.

If we didn't, he'd cum in my mouth and god, I loved that! I loved the way it tasted and filled my mouth until it dripped out, or he'd start cumming in my mouth so I could taste it and then he'd push my head off his cock and cum on my face. Either way I'd end up getting as much as I could into my mouth and then swallow it, gazing up at him with a big smile on my face to show how happy his sissy was to please him.

Then he'd lie on his back on the bed with his cock softening and tell me straddle him and stroke my clit. Sometimes he'd tease my balls while I pleasured myself with what I knew was a look of rapture on my face. Sometimes he'd stroke it for me and sometimes he'd grab my ass and move me up to his face and he'd take me in his mouth and use his lips and tongue on my little clit.

No matter what he did, it would never take me long to sissygasm. I was always so excited and aroused that only a minute or two was all I needed to bring me over the edge. I would have to tell him when I was about to cum because he liked to watch as I spurted my sissy juice all over his chest. He'd push me back if he needed to so I'd splash his chest with my gooey mess, and then he'd make me lick it up and swallow it.

If we had the time, he'd throw me on the bed, and I knew to immediately 'assume the position'. The 'position', of course, was me on all fours with my ass facing him, wagging it slowly from side to side as I looked over my shoulder, smiling at him. I always felt so submissive and so vulnerable like that, offering myself like the cock slut I was, inviting him to violate me like a bitch in heat.

I shouldn't say 'like' a bitch in heat. I WAS a bitch in heat. I was a gurly gurl and I rarely found myself doing anything without thinking in the back of my mind about that big, beautiful, hard cock of his. I couldn't rid myself of how powerful it was, how beautifully shaped and straight and rigid it was, with its long shaft and sculpted velvet cap.

I would be in class, or at the dinner table, or walking down a sidewalk, and there it would be in my mind, so hard and soft and warm and delicious. In truth, I loved it in my mouth because I then had power over him while at the same time I submitted to his masculine lust. His whole body would react to the suction of my lips and every motion of my tongue, while at the same time my hands would roam his body, tease his balls, grasp his ass cheeks and squeeze.

I felt so much like a girl when I was on my knees between his legs, sucking his cock and hearing him moan and whisper about what a good gurl I was and how much he loved what I was doing. As much as I wanted him to fuck me with that cock of his, I cherished every moment of his cock in my mouth and would love to feel him cum between my lips or all over my face, his delicious Daddy seed my reward for loving him as I did.

Whether it was in my mouth or in my boy-pussy, I loved to feel it grow to its hardest hardness just before he came, and to feel it pulse and shoot his hot cum, spurt after spurt, as he emptied his balls into my mouth, or deep inside me, or anywhere he wanted on my face or my body.

Sitting at a desk or a table, walking in a store or getting into a car, or stretched out on a grassy lawn, when I thought of his cock my little clitty would stiffen and ache for him, and sometimes I wondered if anyone would notice it. If they did, I imagined, I would tell them what I was and I would blush and blurt out the truth about Alex's cock and what a little sissy slut I was and how I constantly longed to be the victim of his desires.

In his semi-dark bedroom, after he threw me on the bed and I got on all fours for him, all smiles and giggles with my smooth little balls dangling and my tiny four inch clitty so hard and quivering between my legs, he would get behind me and smack my butt, asking if I had been a good girl or a naughty slut.

Of course I'd been a naughty slut! "I've been a very naughty gurl, Daddy," I'd tell him. "I just can't stop thinking about cock, Daddy. I can't help it!"

"Whose cock, baby?" he'd ask, and if I was feeling playful I'd tell him I'd been thinking about some cute boy I'd seen and what he had dangling between his legs, and how much I'd wanted to get on my knees and suck it and make him cum in my mouth.

Daddy would laugh, telling me I was a liar. "I know you, baby," he'd reply. "I've spoiled you for little boy cock. You only want man cock. No little schoolboy is going to give you what you crave, what you are addicted to!" And then he'd spank me!

He'd yank my panties down and spank my ass, and then he would caress it. His big strong hand would wander all over my ass and then a spank! Then more caressing and suddenly another slap! I would shudder and moan at every slap and then moan some more as he held me down with one hand and stroked my firm little cheeks or tease my little balls or, god!, the intense feeling as he'd tease my clitty between spanks.

Even better was when he'd lube his finger and tease my little hole between spanks. He would circle the tight ring of muscle and then would come a spank. He'd circle more, and then another spank. Then he'd circle and start to push in and spank me again, and finally he'd push his finger in, and finger fuck me while he spanked me.

I would moan and buck and push back against his finger as it plunged in and out, or as he wiggled it inside me, and I'd gasp at every slap, wiggling my ass, wanting more.

Sometimes he would spank me very hard, other times he was gentle. I liked the hard spankings the most because the feel of my butt turning red made my sissy clit all the more sensitive and my little hole would relax, getting ready for his big Daddy cock to pierce me. Either way, I was in a place called Sissy Heaven!

Then he would mount me. I'd feel him getting into position and lubing his cock and my pussy, and then I'd feel the heat of his cockhead as it brushed up against my tight hole.

Then he'd grab my hips and push in.

It still hurt a little when he first pushed the head of his thick cock inside my boycunt, but now I was expecting it and knew that once it was in me it would feel so wonderful! I knew to relax and push back into his thrust, making that part so much easier for him.

His strong powerful strokes, deep-dicking my tight hole, had my little clit leaking all over his sheets. He was fucking me for real now, and I fucking loved it! I moaned and I bucked and writhed and leaked. Every time his hard cock hit my prostate, a jolt of electricity went through my body. Jolt after jolt would course from my sex to my brain and even my toes would curl as the pleasure spasmed through my entire body.

"Fuck me, Daddy!" I'd moan. "Fuck me harder, Daddy, fuck me faster," but he'd control the rhythm and the speed and the power of his thrusts, sometime pulling all the way out so he could ram his cock in again, sometimes moving slowly so I could seem to feel every contour of his cock as it moved in and out of my ass.

As I moaned he would ask if I was still interested in some boy's cock. "No daddy!" I'd yell. "Your cock is the only one I want!" and I'd beg him to fuck me more.

I'd shake and squirm, yell and moan as he turned my guts into Jello with his power fucking. Eventually that unbelievable feeling would well up inside me, taking me over the edge. I existed only on a sexual level as his cock fucked all reason and rationality out of me.

Then I would explode in the most mind blowing, toe curling, eyes to the back of my head, howling orgasm. Nothing on earth could compare to that feeling! My orgasm was so strong it would pull the cum out of Daddy's well stocked heavy balls and he would shoot wave after wave of man seed deep inside me.

Then I would collapse. He would chuckle and tell me what a good girl I was as he lay on top of me, his cock softening. Then we would curl up together in the afterglow and he'd kiss me like a lover. We'd lay there like that until I came back to the world and I would have to go.

I can't tell you how many times Alex gave me everything I wanted and needed from a real man, and how much he taught me about pleasing men and being a sissy. Since those days I've sucked a lot of cock and been fucked many, many times, but he spoiled me for the love of an older man who could be my Daddy, and own me, and use me for his selfish pleasure while I got everything I needed for myself.

I'll never be as pretty a young girl as I was then, but I'm a beautiful woman now, constantly in search of the sexual gratification I need so badly, but always hoping and wishing for a Daddy whose hard cock I can worship and whose love I can earn and return.

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5 Comments
AnonymousAnonymous7 months ago

What a glorious adventure. To worship cock and be constantly rewarded with it down your throat and

in your boy pussy. I stroke myself wishing I was Nicholas/Nikki.

pokeyridepokeyride7 months ago

This is an amazing story that I would love to happen to me. I'm not a young man any longer, but I want to experience the passion this story displayed !!!!

petergoodepetergoode8 months agoAuthor

Dear Readers - I do so love to think of the arousal you hopefully experience while reading my stories. Please do comment, favorite, and follow me. I appreciate it! I love hearing from you directly via my author page, and of course if any of you ever get to Boston, I want you to let me know. Perhaps we can enjoy each other and make a new story;-)

Peter Goode

KatiwantsKatiwants8 months ago

So very beautiful with lots of love and deep passion and pleasure!!!

AnonymousAnonymous8 months ago

A truly beautiful story. The entire series is a masterpiece of eroticism and passion. Definitely five stars.

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