tagTranssexuals & CrossdressersSissy for an Older Man Ch. 01

Sissy for an Older Man Ch. 01


Let me start at the beginning, when I was younger, and much randier. I had just turned nineteen and had finished my first year of college. I had elected to stay on and pursue a few extra credits over the summer. That was not all that I planned to pursue. College had afforded me plenty of opportunity for sexual experimentation, and I had every intention of carrying on in my wicked ways.

I had always been rather a pretty boy with somewhat feminine mannerisms. Never much of an athlete, the other boys tolerated me, but considered me a bit of a sissy. This was alright with me as I preferred spending time with the girls anyway.

When I first discovered sex, it was with girls and I loved it. They seemed to enjoy it as well. However, once in college, I was not long in discovering that men, gay men, found me attractive, and that these men could provide me with a quick and easy (and often very dirty) outlet for my sexual urges. I began to hang around in a park where I knew that they cruised. Men would try to pick me up, often within minutes of my arrival. I began having sex with these men with increasing frequency, usually in the bushes, washrooms, and their cars. I loved going down on a man's cock in his car, sometimes while he drove around town. They were so cute trying to control the vehicle while they came in my mouth.

As it turned out, it was my somewhat feminine nature, for which other boys had excluded me, that they found so attractive. Of course I began to play on this, exaggerating my feminine ways to get their attentions. I began to dress in a more femme manner, wearing short shorts which emphasized my long legs and shirts of silky materials opened wide at the collar, and often tied at the waist. I started wearing women's underwear. I kept my body shaved smooth, removing what little body hair that I had started to develop. I began to wear jewelry.... rings, bracelets and necklaces. I really got into being more femme, and would wear perfumes and if I was feeling particularly daring, a trace of lip gloss or eye shadow. I even began to paint my nails with an opaque polish. I began to exaggerate my already feminine mannerisms. My walk took on a distinct wiggle, and I usually had one hand strategically placed on my hip. I began to smoke long cigarettes, always being sure to hold them between the tips of my long, slender fingers, my wrist held limply in the air as I had seen my female friends do.

Needless to say, I had no trouble attracting men, particularly those who wanted a little faggot to go to work between their legs; and, believe me, I started to love going to work between their legs! My craving for cock was growing. I had little interest in girls. I started cruising for men more often. I would take on almost all comers (pun intended). I did wonderful, young studs and I did dirty old men. I did femme guys like myself and I did macho, masculine men. It was all great! It was in this way that I met the man I consider to be my first real "boyfriend".

I had arrived at the park feeling particularly horny this summer evening. I had dressed in extra short denim cutoffs and a black silk shirt. I wore a gold chain on my neck and a matching bracelet on my wrist. before getting out of my car, I checked my face in the mirror, fixed my longish blond hair, and decided to add an extra coat of lip gloss. I was ready. Look out boys!

Getting out of the car, I stopped and lit one of my Virginia Slims 120's and started across the parking lot. I hadn't gotten 20 feet when a rather expensive automobile pulled out and started to slow when it got nearer to me. It pulled alongside me and the window came down. Inside was an older, though not unattractive, man who looked to be in his mid-fifties. His hair was thinning and grey, his skin fair and his eyes a soft blue. He held a thin cigar and asked if I had a light.

"Sure." I reached in my pocket for my lighter. I could see that he was checking me out, his eyes taking in my legs and working their way up again, pausing only briefly at my crotch. Licking my lips, I flicked the lighter, offering him the flame. He lit his cigar, and blew the smoke out. He looked at me, smiled and asked if I wanted to go for a ride. Of course, I responded in the affirmative; it was obvious what he was looking for, and I planned to give it to him.

"Get in." he said. I walked to the other side of the car and opened the passenger door. I slid into the car and closed the door. Once inside I crossed my legs to give him a better look and looked over at him. He was looking back at me and we exchanged pleasantries. He told me his name ws Ronald and we chatted about the weather.

While we were talking, he finished his cigar and, after stubbing it out, placed his hand on my leg, looked over at me for a reaction, and smiled. Smiling back, I uncrossed my legs, placed my hand on the inside of his thigh, and began to rub, slowly working my hand up toward his crotch. He moaned audibly. Removing his hand from my thigh, he undid his trousers and pulled out a very nice sized, thick cock with the loveliest mushroom head I had ever seen. As I licked my lips, he asked "Is this what you're looking for tonight, baby?".

I replied "Mmmmm definitely...."

Reaching over, he grasped the back of my head and pulled my face toward his cock. My hand gripped the base of his shaft as my pink tongue flicked over the head of his manhood. I parted my pretty, painted lips and opened my mouth, placing it onto his cock, feeling it's thickness as it entered. The taste of precum was salty and warm and I savoured it. He moaned louder as I worked my magic on his lovely cock. My head bobbing up and down, his thick tool sliding deeper and deeper into my mouth, my lips tight around the shaft. Each time my head pulled up, I circled the mushroom shaped tip with my tongue. I licked the length of his shaft, all the way to the base. Only then did his moaning cease as he spoke.

"Lick my balls, bitch," It came more as an order than a request, and I complied.

He had seemed like a nice gentleman up to this point, but with those four words, he showed a domineering side, which I had not picked up on. It was clear that he liked to be in charge. His hand moved to the back of my head and he held my hair firmly in his fist, guiding me to where he wanted me.

"That's it.... you like it rough, don't you, you nasty little cocksucker? Want to be my bitch, don't you baby?"

I was a little unsure where this was going, but I knew I was getting turned on by this man calling me his bitch and I replied, "Mmmmm... make me your bitch baby..."

"Such a good little cocksucker..." he said as he pushed my face deep onto his cock, forcing it into my mouth like a weapon. I was now hornier than I had ever been, my denim cutoffs stained with precum.

He kept calling me names. I was loving it and he knew it by how enthusiastically I sucked his cock. He continued calling me names: bitch, slut, cocksucker, faggot. The more he verbally abused me, the harder I sucked his cock.

I knew long before he came that I wanted his cum in my mouth, I wanted to swallow this man's seed. When it was finally time and I felt his cock twitching and swelling in my mouth I was in heat. I not only wanted but needed his cum. "Oooooh Yeahhh.... take it you you little fag," he near screamed as he shot a huge wad of cum into my mouth. Thirstily, I swallowed every drop, licking the remnants from his cock head greedily

Afterwards he Pulled up his trousers as I tried to compose myself, wiping off my face and chin. I had been so engrossed in my cocksucking that I hadn't realized that we were parked back in the parking lot. Nervously, I fumbled for a cigarette. As I pulled one out and placed it to my lips, he reached over and lit it for me. He pulled out a cigar and lit it. Leaning over, he blew smoke in my face, kissed me full on the lips and shoved his tongue into my mouth. Although I almost never kissed the men I picked up, I found myself eagerly wrapping my tongue around his. He then pulled away and took a deep drag on his cigar.

"Did you enjoy that?" he asked.

I answered as honestly as I could. "More than anything," I said.

"Good, I want to see you again. Give me your phone number." Again, this was more a command than a request.

I had a policy never to give my number to the men I met. In this case I just had to see him again, and I quickly took the pen and paper he offered, scrawling my name and number on it.

Taking the pen and paper back, he said, "Good, I want you available when I call. I'm going make you a proper bitch next time."

It was dark when I walked back to my car, and I was already anxiously awaiting my next encounter with this sexy man, and wondering just where this was going.

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by Anonymous

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by Anonymous08/12/17

Oh, my, YES!

You just lived every sissy's fantasy. Nothing better than being able to dress fem and serve a dom older man then get nothing in return. That's our purpose in life. So rarely do these real men give usmore...

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