Sissies don't Disappoint Daddy Pt. 01

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...

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At the age of eighteen, I was still slender and small in every regard. The genes I was born with simply dictated how my body developed, and I was always smaller than everyone else my age. I had almost no hair on my body and I couldn't be considered strong at all, especially compared to any other male my age. It made me shy.

At the gym there were girls stronger than me! And in the locker room it was obvious to me as the others walked around naked that I was smaller down there as well. I never walked around except with a towel in front of me. It made me even shyer.

I am a Sissy but I didn't know it. The few friends I had talked about girls, and watched porn, and here I was, busy watching anime and thinking how dreamy the guys were. I was so dumb, though, that I really wasn't even aware of what I was thinking.

I just didn't have any interest in girls and I had to hide that from my friends and pretend to be like them. Meanwhile when I watched porn it was the older, strong men and their bodies I was fascinated by. They were just so... well, whatever I was not! Those hard cocks, so much bigger than my little clit? Seeing them made me so excited; a feeling I didn't understand and didn't think about until I got to know Alex.

Girls thought I was cute, and a few showed obvious interest in me. I hid behind my shyness when that happened, but I have to admit that that was just a cover for what was really going on in my mind. Honestly, I looked like a girl with my long hair and an almost completely smooth, feminine body.

We had a neighbor that lived a few houses away and Alex had a pool. He was in his late 30's which to me seemed impossibly old! My parents were friends of his so I had a standing invitation to use his pool whenever I liked. The south is hot! No getting around it, it can be just painfully hot, so I used his pool after school as often as I could that summer.

He was divorced and worked as a teacher, so he had the summer off, and he'd sit by the pool whenever I was there. He told me it was for safety reasons but as I swam and jumped into the pool over and over I began to notice how he was watching me.

Every time I looked at him he had his eyes on me, and to tell you the truth I was kind of flattered to have that kind of attention on me. Then I became more than flattered.

One day I got out of the pool and turned quickly and yes, there he was, staring at me, but the towel was tented up between his legs! Mortified, I jumped quickly back into the pool, but as I swam around avoiding his eyes I couldn't deny that the big stiffy I saw poking up under that towel excited me tremendously.

My own little friend was now at attention in my swim trunks and I wanted so badly to look and see the shape of his cock pushing up against his towel again, but I didn't dare let him see me looking.

Between the attention he paid me and the sight of his hidden erection, the feeling of attraction overwhelmed me. When I got home that night and went to bed I lay there thinking about what he looked like under that towel and I got my own stiffy.

My member was so hard it actually ached and I had to relieve myself! I stroked my little cock furiously, making sure that when it spurted it was into some kleenex and not all over the sheets where my Mom would see the stains. I had masturbated before, of course, but I had never cum as much and as hard as I did that night.

He was a very good looking man, not muscly but solidly built and strong looking. He had a handsome face and a warm smile, with a hairy chest unlike mine. His legs had hair as well, though his back was pretty smooth and the shape of his body was divine, just like in some of the anime I used to watch; broad shoulders and a narrow waist, long legs and big brown eyes with a mop of thick hair that tended to fall over his forehead.

Now there I was, still naively thinking this was all in my mind. I know this sounds stupid, but it took me a solid week to put two plus two together and realize that the reason his cock was hard and standing up under that towel was me!

I loved that possibility and to test it, in my own shy way, I started flirting with him. I began wearing an old bathing suit that was really too small for me. It was stretchy and clung to my little rear end, exposing a bit of my cheeks. When I looked in the mirror with it on, I could see it didn't fully hide the shape of my little package.

When it was wet it would hug me even harder, and I'd get out of the pool and stretch with my arms over my head. I'd touch my body here and there as I adjusted my bathing suit. I'd bend and touch my toes a few times with my back to him. Things like that.

I really had no idea how to flirt (and still don't) but every time I looked his eyes were on me, and whenever I swam from the opposite end of the pool towards him I'd look at him and get a smile in return.

I had no thought of seducing him. That seemed impossible. It just excited me to see him watching me. My tiny little cock got hard as I played around in his pool and stayed that way. I could see his eyes move from my face to my bathing suit as he smiled at me when I got out of the pool or when I floated on my back on a blowup raft.

That made me even harder and I knew he could see that. I vacillated terrifyingly between wanting to run away and hide and wanting him to see the shape of my little cock as it strained against my wet trunks, or see how the material clung to my ass; and of course wanting to see what was under his towel!

I don't know how it happened. I think it must have been totally my subconscious at work, but I showed up one day at his pool and I'd forgotten my swim trunks. When I told him I had to run back home he laughed and told me it was totally ok if I wanted to swim with no trunks on.

I must have blushed red like a beet when he said that because he laughed and put his hand on my shoulder, telling me, "It's ok, Nick, no one can see in here and I don't mind."

When I couldn't do anything but stare at my feet, frozen, he said, "Really! It's ok! I don't care, and why bother going all the way home and back again when it's this hot out?"

I still couldn't move and he turned me by the shoulders and gave me a little push and said, "Go on now, get in the pool!" with a stern voice.

I didn't want him to see what was going on in my pants! God, my little cock was so hard it ached at the thought of being naked in front of him! So I walked to the opposite end of the pool, dropped my towel, and undressed with my back to him. I turned and jumped quickly into the pool and sure enough, he was watching me intently.

Being naked in front of him was both unbelievably embarrassing and thrilling as hell. The butterflies in my stomach battered and bashed into each other. My little erection would not go away and I hoped he couldn't see it as I swam around. But then I wanted him to see it too!

My embarrassment melted into a haze of arousal and I climbed out of the pool and jumped back in a number of times, turning just enough to show him a flash of what was standing up between my legs.

His smile and his gaze seemed even more intense than usual and I could see his towel tenting even higher than I'd seen before. God, I wanted to see what was under that towel and my stiffy would not go away! Eventually it did. I suppose it got tired of standing up rigidly for so long, but I was finally able to get out of the pool and get my clothes back on.

Of course as I did so, I could see his eyes locked on my young, slender body and I took the thrill of that feeling home with me and to bed later that night. I satisfied myself furiously as I pictured him taking that towel off from over his beautiful, masculine body and revealing what was underneath!

Believe it or not, I was so naïve that I considered this all in my mind. I didn't even consider that I'd been flirting obscenely with him. I had no idea how to flirt (and still don't! I get completely flustered when I'm around an attractive older man) and I certainly wasn't thinking I could seduce him.

This was all a high school senior schoolboy -- or in this case, school gurl -- horny fantasy to me, but a friend of mine had recently introduced me to weed and I loved it. One day, Alex told me he saw me smoking near his house and asked if I'd like to go inside after swimming and smoke a bowl with him.

"Sure!" was my immediate reply, so that day when I got out of the pool he told me to come inside and we'd get high together. When I walked into his house, I discovered it was nicely air conditioned and tastefully furnished with brown leather and modern furniture.

He told me to take off my swim trunks and jump in the shower and wash off the chlorine. While I was doing that he popped quickly into the bathroom and said he was leaving me a towel to put on when I got out and then left and shut the door again.

When I got out of the shower I discovered that my trunks were gone and he'd left me a beach towel to wear after I dried myself. I walked back into the living room and found him sitting on the couch with only a towel on himself, packing a bowl. He told me to sit next to him and we began sharing the weed he had.

Whatever was in the bowl was really strong and before very long I was massively stoned. The next thing I knew he was rubbing my shoulders. It felt so wonderful having him touch me, having his big strong body closer than it had ever been. I was in an absolute daze and starting to get aroused.

I don't know exactly how it happened, but somehow he turned me with my back against the back of the couch again and he was kissing me. There was a dreamlike moment when he leaned in and lowered his lips on to mine and I opened my mouth to his tongue and we were kissing like long-time lovers.

He was kind enough to take things slowly with me as time went on, but that first kiss was electric. I was lost in the sensations of his body pressing against mine and his tongue dancing with mine. I didn't know how to kiss but it seemed so natural to just follow his lead and do whatever he did, and my arms circled him and pulled him closer as we made out.

My little cock sprang to attention and I felt like I was on fire between my legs under that towel and I started moaning as I felt his big hands wander over the bare skin of my body. I was in shock but in a good way and I kissed him back passionately and felt so proud and happy that a man wanted me.

When his hand fell over the little bulge under my towel I started to writhe and moan into his mouth. He began stroking me through the thin towel and I reached over, as if my hand had a mind of its own, to grasp his cock through his towel.

It felt so big and hard! I don't know that I can say it was massive but it certainly seemed that way compared to mine, and I later discovered it was a perfect size for my mouth and for fucking me.

I stroked it up and down and then used my fingers to explore its contours. I could feel him clench his leg muscles when I teased up and down the long shaft and when I traced the outlines of his cockhead, and so I alternated that with circling his cock with my fist and stroking up and down.

I couldn't believe how deliriously hot it felt to be stroking a big mancock as I kissed its owner, even though it was still covered. It felt so big and powerful but I didn't know what else to do. He broke the kiss and smiled at me.

"I'm going to teach you everything you need to know about how to please a man, Sweetheart," he said. It was the first time he called me that and I almost melted on the spot! "But for now I just want to do one thing."

He stood me up in front of him and undid the towel. As it puddled on the floor, my little four inch sissy clit popped up and he cupped my ass and pulled me closer. He leaned forward and took it all in his mouth and started to suck me.

Oh, my god! The warmth and the wetness, his tongue and his lips, my straining hardness and the gasps being drawn from my throat; time seeming to stand still. It couldn't have taken more than a minute but that minute was frozen in my mind and I had my first sissygasm! I seemed to erupt between his lips and it was all heat and cum and pleasure and wet and release in his mouth.

I shot my load into his mouth and my knees went weak. I couldn't stand up anymore. He pulled me down next to him on the couch and kissed me again. I could taste my cum on his tongue and I fell back amazed that anything could feel so good.

I wanted more. I wanted to please him like he pleased me but he told me that I needed to get back home and come back over the weekend when we had more time. And so I did!