Dressing Up with Filly

It was another early Saturday morning at the sports complex and after spending some time in the pool I was lingering longer than necessary, as usual, in the changing room, engaged in my favorite pastime, looking at the mature men there and secretly admiring their lovely bodies, especially their daddy cocks. Since I was an older teenager I had become obsessed with men and their hairy, mature bodies, which fueled all my masturbation on a daily basis.

Sadly, for me, as I reached my late teens, it seemed that all natural male development and growth had passed me by. All my classmates grew tall, strong, hairy and masculine, whereas I remained small, soft, puny and underdeveloped. I was glad to finish high school and the unending ribbing about my lack of development which had made my school life a misery, especially in the changing room. I was a soft target for the bullies and a figure of ridicule for the girls. They even nicknamed me TC, not Top Cat, but Tiny Cock. My life was one of constant humiliation and I was so ashamed of my weak, soft, body.

I did like swimming and took to visiting the pools at the Sports Centers in town where I soon discovered my preference for the bodies of mature men. Moreover, I soon got to know the best times to be there, early in the mornings, and best of all, these older guys hung around undressed, just chatting to one another, totally at ease with their nakedness. Often their conversations were raunchy and vulgar as they spoke about fucking women or some sexy girl who worked in reception or who worked in some bar they frequented. I sat there in awe and spied on their big hairy cocks so I could fantasize about them later.

Sometimes they talked openly about whores they had been with and the great blow jobs they had received. They even talked about how they had fucked Mrs Jones, a librarian with really big tits, who worked in Central Library in Main street. Several of them had been with her. I knew this woman, she was very sexy and womanly, but she was also a married lady. In my innocence I was quite shocked but also fascinated. They said she was so sexy, wore vintage lingerie, gave great head and really knew how to please a man. I longed to hear the details of what she did for them and at night, alone in my single bed, I pictured her with them and wanked myself silly. I became so jealous of her and then, of course, I gradually wanted to be her, or to be like her, so that these men would want to fuck me. I started to imagine myself as her.

I kept all these thoughts and fantasies to myself and assumed that the men did not even notice my presence or how long I sat there looking and listening. Around the same time, I started sneaking into my sisters' rooms and going through their underwear drawers. I was fascinated by the sensuous thrill I felt when I touched their soft, silky panties, their beautiful, nylon stockings, their suspender belts and garters, their sheer night attire, their bras, their slips and half-slips. To me these items of lingerie represented a treasure trove of hidden delights that women would wear to please and pleasure real men and of course, I could not resist the temptation of rubbing this delicate finery against my rampant, little cock. I had to try them on. The urge to do so was as strong as my need to look at the naked bodies of the mature daddies at the pool. My evolving sexual persona associated pleasure with older men and the sensuous feel of delicate lingerie. It never crossed my mind that there was anything Gay about my fantasies. For me, my delight in men's cocks and female lingerie was just something that heightened my sexual pleasure.

Naturally, I never wanted anyone else to know about this effeminate side to my nature. I recognized that I would never be a stud. I recognized that I was not an Alpha male nor never would I be. I knew I was inadequate as a man. One look around the changing room on any given day bore witness to these facts of life. Worse still, I did not last long when I excited myself and when I had my precipitous orgasm, the cum only dribbled out of my little uncut cock. None of life's harsh realities about my body and its inadequacies, its failings, made me happy but somehow, my secret fantasies compensated for my lack of manliness and gave me pleasure and relief. I also lived in dread of being caught out.

I knew my fantasies were bizarre and every visit to the changing rooms only caused me to sink further and further into my twisted surreal world. When I thought about Mrs Jones with one of these men it was not just the guys with the biggest dongs or the best bodies. Sometimes I pictured her with insignificant little men with ordinary cocks. Sometimes I imagined her with fat men or thin men, big men or small men and to my horror, I even had her fuck the loud, brash, know it all types, whom I detested in real life. To my shame, I wanked myself off imagining I was the woman with all these men, kissing, licking, sucking and fucking them, regardless of their cock size, age or physique. As I fell deeper and deeper into my obsessions I was slowly losing my grip on reality. Night and day my mind was plagued with thoughts of daddy cocks and lingerie and my imagination ran wild with endless scenarios.

On account of my strictly religious upbringing, every masturbation session ended with me feeling guilty and ashamed of myself. Ofttimes, I detested myself and my weakness of mind, as well as my soft, hairless immature and underdeveloped body. I went through periods of self-loathing and disgust and there was no one to talk to about my filthy thoughts and love of lingerie. Then Phil entered my life and changed everything for the better.

This particular Saturday I continued to look at men's cocks surreptitiously, with envy and desire, in the firm knowledge that I would never be like them. I couldn't help but look at daddy cocks imagining my hand reaching out towards one. Lost in my reverie, I failed to notice a man standing close to me wearing his towel wrapped around his thick waist. He spoke to me.

"Did you enjoy your swim, sonny,"? he asked me in a rich deep voice.

I looked up at him and just nodded affirmatively. I had observed him in the pool and the changing room often before and secretly admired his manhood. He unwrapped his towel to continue drying himself and in a split second my keen eyes took his whole body in. He was probably late forties maybe early fifties, jet black hair with wisps of grey at the sides, twinkling brown eyes, over six feet tall, broad shoulders, strong arms, thick around the waist and very masculine, long muscular legs. As he continued drying himself I saw his cock and his balls. He was less than two feet away and I could not stop staring at it.

I had never been this close to another man's cock. It was about four or five inches long, rather thick and veiny, and his circumcised crown was a thing of beauty, proud, fat and pronounced. Behind it, hanging low and with a smattering of black hair, was a set of golf ball size, testicles. Above this apparition of manhood was a forest of black hair that thinned out to a treasure trail below his tummy button. His pecs had some hair and his nipples were quite prominent. There was hair on his forearms and his legs were really hairy. I found it difficult to breathe. I already knew that in my mind again, he would be making love to Mrs Jones or me that night.

He was everything I was not as a man. He put his towel around his neck, stuck out his hand and introduced himself.

"I'm Phil, by the way. What's your name, sonny?"

"D... Don," I stuttered. God I loved the sound of his voice.

"Well, Don," he continued, "I could sure do with a coffee. What about you? Do you fancy some?"

His friendly invitation took me by surprise. I thought I was invisible to these men. I mumbled my reply.

"Sure."

"Well, get dressed sonny, and we can get to it," he commanded.

I noticed him watching me as I dressed myself. I was so self-conscious about my body that I turned my back to him to put on my boxers. I felt the palm of his hand slap my bare bottom and I turned around in shock to look at him.

"So cute," he said and smiled at me.

I dressed quickly and we were soon walking out of the Sports Complex. The coffee shop was packed so he suggested we have coffee in his house. It was all so natural and matter of fact with him that I just agreed to tag along, despite my nervousness. I did find him very attractive and he had often been in my sexual fantasies.

After a ten-minute drive, during which he did all the talking, mainly about the importance of swimming and fitness, we pulled in to a driveway in a posh suburb. We went inside and he switched on the coffee pot, which he had prepared before going to the pool he said.

When the coffee was ready, he poured some rum in to his and asked me if I would like a spot of rum in mine. I said yes although I had never had rum in my life before. It sure tasted good. I sat down on the sofa and he sat beside me. The coffee with rum helped me relax and Phil's voice was soothing. I was feeling very comfortable.

He said he had noticed me at the pool a lot recently and wondered why I was always alone. I told him I didn't really have any friends and I preferred to be alone. He suggested that he and I could become friends if I fancied that. I told him I thought that would be good. He asked me about girlfriends and I told him I did not have one at the moment. He said he had been married once but his job, he was a salesman, involved a lot of travel and things did not work out.

"What do you sell? I asked innocently and his answer bowled me over.

"Ladies underwear. Lingerie. You know, panties, bras, corsets, nylons, suspenders, the whole kit and caboodle."

My eyes opened wide in astonishment and before I could stop myself, I blurted out that I would love a job like that. My face turned crimson and I did not know where to look. Phil just laughed and said everyone reacts like that when he tells them what he does for a living. While saying so he placed his hand on my forearm and did not remove it.

"Yes," he said. "It is a dream job for me. I love lingerie. I have always been fascinated by it. As a teenager I used to rifle my sister's drawers just to touch the soft silky fabric of their undergarments. All teenage boys do this. I am sure you have too, Don, haven't you? Hell, I expect you have even tried things on, I know I did. I was so obsessed with lingerie that I found myself a job in it and now I have a successful career out of my pet obsession. So Don, do you?"

"Do I what?"

"Do you like lingerie, too? I suspect you do. I suspect you have tried on lots of frilly, girly stuff. Well, have you?

He poured some more rum into my coffee and thankfully, continued speaking...

"I still wear lingerie you know and I 'll tell you why. I love how it feels against my skin. I love how it makes my cock really, really hard. When I cum in panties I shoot so much more cream and it spurts out in big jets, jets of jism, why sometimes I even gobble it up 'cos it tastes so good."

My eyes were still wide open in surprise and I was intrigued by what he was telling me. I was still embarrassed by the conversation but inwardly, I was delighted. Phil wanted to be my friend and he had just admitted to a lifelong obsession with lingerie. I wanted to tell him all about myself, how I too, loved lingerie.

"So, baby doll, have you ever tried on girl's stuff, you know, little soft panties, stockings and a suspender belt? You have, haven't you? I can tell from the look on your face. You're dying to tell me."

For some reason I told him the truth.

"Yes," I whispered and my face reddened. I told him some of the things I did.

"It's great. Have you wanked off into panties?" he asked me.

"Yes," I admitted, feeling breathless, yet excited. "Every time I get the chance."

"Don't be embarrassed. It is perfectly normal. All guys secretly love wearing panties or touching their cocks with silky panties. It makes them hard and it feels so good. There is nothing like putting your hand up a skirt and touching a woman's panties, touching her wet pussy through her panties. Feel her getting hot and sticky and then sliding them down over her ass and down her thighs. Even better is to do the same to another guy. Best feeling in the world, right, baby doll, a hard cock inside soft panties? You know what I am talking about, right?"

His hand moved to my leg and he caressed my thigh gently, then squeezed it, before touching my arm again. I swallowed. I was bewildered but excited. I was not quite sure what was happening. Is he really saying these things? Phil seemed to regard what I thought as my, "unnatural behaviour," as something perfectly normal.

"Would you like to see some samples of what I sell? Of course you would. Help yourself to more rum and coffee. I'll be back in a moment."

He excused himself and left the room. Five minutes later he returned empty handed. I was disappointed but my disappointment was not to last long. He told me he loves to wear suspenders, stockings and panties and he still does it. He even sleeps in a negligee.

"Would you like to see what I love most to wear?" Phil asked me.

"Yes, please," I replied.

With the rum in the coffee and being at ease with this tall man I thought he was just going to show me samples he would take from a bag. I was getting excited at the prospect of the delicious garments he was going to show me, when to my surprise, my new friend stood up, removed his shoes, undid his belt, unzipped his pants and let them fall to the floor, revealing a pair of sheer vanity fair, black nylon panties, with a black, six gartered, suspender belt and black, sheer nylon, stockings.

I gasped for breath. I could not take my eyes off his engorged cock. My pants were tenting awkwardly. He must have noticed the shocked look on my face. I think my mouth was hanging open and it felt dry. I was speechless. He kicked off his trousers and proceeded to walk up and down in front of me. He was even wiggling his hips in an exaggerated fashion. Oh my God, I thought, this is exactly what I do when I wear my sister's panties, only he was a natural. He was bewitching me.

"Come with me," he said, reaching his hand towards me. "I have something for you to wear and we both know you will love it. Don't be shy."

Taking my hand, he pulled me up to my feet. His hand was big, warm and firm and dwarfed mine. I was enraptured by his apparel. I wanted this... so much.

"Touch my panties, baby doll," he said. "Feel how very soft they are."

As if in a trance, I offered no resistance when he took my hand and rubbed it tenderly, up and down his swollen, manhood. The softness of the panties was irresistible and the hardness of his cock even more so. I was mesmerized.

"You want this, don't you Don? We both know you want this as much as I do. Tell me you want this."

I tried to say yes but my throat was dry. I could not speak. My breath came in short gasps. My cock was aching with pleasure. His fingertips danced on my erection. I moaned loudly. I wanted this more than anything else in the world. I gave in to him, willingly, longingly. This was what I had been fantasizing about alone in my bedroom.

"This way," he said. "Let's get you dressed in something pretty, honey." He was speaking softly now. He took me by the hand again and said. "Follow me. You know you want to. Don't be afraid. We will have fun, you and I."

I was so excited and so nervous I followed his lead down the hall and in to his bedroom. The touch of his hand was warm, manly and strong. It comforted me.

"Shall I undress you Don? You do want me to, don't you?" he said reaching for my belt.

He unbuckled my belt, pulled down the zip and my cock jumped at his touch.

"You are hard now, aren't you? I like that. Look at what is on the bed for you to wear. I hope you like them. I bet you will be even harder still when you get them on," he said, as he undid the clasp and dropped my pants down over my cock and on down past my thighs.

"I love your slim legs. You have such lovely, slim legs," he said smiling. "So white, so hairless. You are smooth and soft, just like a girl. I love that about you."

His fingertips softly touched against my inner thighs and I thought I was going to come. My cock was crying out to be released from my shorts. Leaning down he pulled sharply and they were off. He told me to step out of them and to kick off my shoes and I did so.

"I can't wait to see your little cock in those lovely, white, nylon panties. Take off your shirt and we will put them on you, pet."

My state of excitement and arousal increased as he helped me unbutton my shirt which I dropped to the floor. He placed his hand behind my right knee and pulled my leg up so he could remove my sock. I had to hold on to him so as not to fall. As he set my leg down his big hand slid up the back of my thigh and I delighted in his touch. He did the same with my left leg. For the first time in my life I was naked in another man's bedroom with my cock at full mast. He sat on the bed and told me to get him the panties. As I reached across the bed for the panties I felt his hand cup my right buttock and a moan escaped his lips and mine. I heard him say "Oh fuck!"

I handed him the panties as he sat on the bed with his legs opened. He pointed to the space between his open legs. Trembling with excitement, I stood between his nylon covered thighs and placed my hands on his shoulders to assist with my dressing up. I lifted my left leg up and he put my foot through the opening of the panties. I did the same with my right leg. He was bent over and the hair on his head was kissing my cock. Slowly he drew the panties up my legs and as he did so, his warm, wet, tongue slid up the length of my cock. I cried out pleasure. This was a dream come true.

"What's the matter pet?" he said softly. "Has no one ever licked your little cock before?"

As he was speaking he finished pulling the white nylon panties up and slowly adjusted them. The attention of his hands on my bum and my cock teased me mercilessly. The urge to cum was overwhelming me now.

"Is my little friend aroused? Does he like the lovely, little, white panties. Virgin white for my virgin boy. Now look at that. You are such a bold boy. Look at the stain that is growing on the front of your pretty panties. Did your little cock do that? Are you leaking pre cum? You love this, don't you? Well, don't you?"

His teasing was driving me crazy with desire. I finally found my voice.

"Oh God, I'm going to cum! I am going to cum!"

He pulled the panties out at the waistline and forcing them down to the tops of my thighs, he cupped my bum cheeks in his hands and sucked all of me into his mouth, just as my first spurt of cum dribbled out. I cried out in ecstasy and continued dribbling in to his mouth. I almost fell over from the exertion. When I was finished he pulled me down on to his lap and brought his lips to mine. This was my first male kiss.

I willingly opened my mouth for his probing tongue and cum flowed from his mouth in to mine. We swirled it around back and forth, our tongues delighting in the taste, before he swallowed it. Oh sweet rapture! My arms wrapped themselves around his neck and he held me tightly in his arms. It had all happened so quickly and felt so intense. I was like a little boy sitting on his daddy's knee. His still, engorged cock was pressing itself against me. I felt my own cock come back to life.

He finally broke off the kiss and took my face in his hands as I held on to him. Threads of cum and saliva were like bridges joining our lips, cementing us together. I stuck my tongue out to lick my lips.

"Oh Don, your face is quite soft and smooth!" Seeing my face redden from embarrassment, he reassured me immediately. "I love it. It's so soft. It's wonderful."