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Emma Enjoys The Stories Of A Sissy

Emma Enjoys The Stories Of A Sissy

by emmaslut18
11 min read
4.37 (16800 views)
adultfiction

Hi Guys! Most of you know me as Emma, the high school study nerd turned high school slut, maybe the town's number one slut. With help from my new big strong older black 'Daddy' I managed to get my life turned back around and get my law degree at a top university. I've since been working for a very good legal firm and with he the help of my stunning body and my desire for kinky, submissive sex I've managed to work my way up the corporate ladder and at age 29 I'm very close to being given a junior partnership. I wanted to tell you about a young man who works at my firm, in a different department and not on the legal side. His name is Liam Harper, he's 24 years old and he has a junior position in IT.

I recently bumped into Liam at a party, a bit of a naughty party as everybody had come dressed in a very sexy way. Of course to hark back to all the fun I'd enjoyed in my last year at school I was dressed as a very naughty, very sexy school girl in the absolutely shortest skirt ever and a little see through blouse that tied around my full 34C breasts. White hold-up to disguise the fact I've been one of the most fucked sluts in the history slutdom. The kind of party that I adore. At the part I first met his hot girlfriend, the very pretty Cassie Bennet. Cassie, 5'4", an athletic young woman, aged just 19, had a physique that reflected her dedication to fitness. Her slender, toned frame, showcased strength and agility, cultivated through regular gym sessions and a passion for staying active. She had long, lean legs that exuded power and symmetry, shaped from a mix of weight training and cardio. Her firm rounded "bubble" glutes complemented her fit silhouette, the result of countless squats, lunges, and leg exercises. I can tell you 'I would'.

Liam was quite different, at 5'8", this young man had a striking presence with a combination of delicate features and a lean, toned frame. His shaggy blonde hair fell in soft waves, framing his face and enhancing his effortlessly stylish, carefree look. Bright blue eyes, vivid and expressive, gave him a youthful allure, drawing people in with their depth and a touch of intrigue. His skin was clear, with a natural, sun-kissed glow that suggested he spent time outdoors, adding to his laid-back, approachable vibe. But he looked very young for his 24 years and was often asked for ID.

The interesting thing when I saw the young couple was that they were both dressed almost identically. They both looked super sexy in their matching white micro miniskirts so that the moons of their lovely round ass cheeks were visible below. Their skirts were even short than mine, the sluts. Their little pink thongs were visible above the skirts, and they had on small white very tight crop tops, see through enough that you could see they were both wearing little pink bras. They were both wearing light make up with matching pink lipstick. There was one difference in their attire, Liam had a pink dog collar and lead that was held in Cassie's hand, and he would follow her like a good puppy. And to my amusement I could also see Liam's little package bulging at the front of the skintight skirt. Bulging might be the wrong word as it was evident by the size of the bulge, he was not endowed with much to impress us girls.

It wasn't until much later in the party that I managed to get to talk to Liam. Cassie was behind him making out with a very attractive older man, probably in his early forties, still with Liam's lead in her hand demonstrating to all at the party, how her poor boyfriend was a submissive cuckold. She was distracted enough for me to have a short chat to the poor boy and we agreed that he would come to my office on Monday morning and tell me his exciting story. I gave his small round ass a squeeze and left him to the evening of whatever fun the couple were going to get up to.

Liam arrived in my office at 11 on Monday morning. As a senior lawyer within my firm, I have a very private office and on occasions I lock the door, so did so today. He explained to me that he had always been into CFNM, for those of you not too familiar with this term, it is when a male is naked in front of fully clothed or semi clothed females. He had known fairly on that he was submissive and his younger sister, by two years, had taken advantage of this fairly on to humiliate him in front of her friends. He also told me that his recent girlfriend, who liked to cuckold him, as I had seen on Saturday night, at the party had even started to sissify him.

Being that we were in very different parts of the company, any form of romantic or sexual involvement between us would not be considered an infringement of company rules, as I have no influence on his position within the company. He had told his manager he had come to my office to sort out an IT situation with my office server.

I told Liam: "Since you are a submissive into CFNM, in that case for the rest of our meeting you should be naked." Knowing that I was going to meet Liam this morning I had deliberately dressed in a very smart, tight shirt and jacket suit. The skirt was dark grey and a very tight pencil skirt that showed off my full round bottom beautifully. I had a very tight white blouse that showed off my large firm breasts and, although Liam would never get to see, underneath I had some very sexy lingerie that included a tiny pair of black Brazilian panties, and black hold-ups.

Although I was not attracted to this small young man, my pussy tingled nicely as he undressed obediently in front of me. It certainly triggered my dominant side, and I couldn't hold back my giggle when he dropped his trousers to reveal a tiny pair of pink bikini panties.

"Liam, you have to give me a twirl and show me how cute your butt looks in those."

Liam had no problem with this as being humiliated like this had become a basic part of his life. I could see clearly that having been made to strip naked in front of me had made his small slender dick very hard as it jutted, pushing out the little panties. He started to turn for me and, he had a very nice firm, quite round little bum, with most of the firm round cheeks on show below the cut of the little panties.

Liam had learned over the years to turn slowly to give his audience a good view and it gave me time to take in his lean toned physique. Not really my taste in men, I like a big muscular man, usually at least six feet. Liam was slim with not too much muscle definition but toned enough to look athletic, but more like a distance runner than a sprinter. I also noticed no body air. As he looked so cute in them, I was in too minds whether to leave him standing there in his little pink panties, but I decided I did want to see him naked and show how small his little dick was.

I told him: "Drop your little pink panties, Liam."

And he did, sliding them down his slender, hair free almost feminine legs, then stepped out of them and placed them on his folded clothes on the chair. Now he stood bollock naked in front of me and I could see his hard erect little dick. I say little, it was probably around 4 to 4 and half inches long but quite slender. So small, but not a micro dick, and probably not a lot smaller than the average dick. But for a true size queen like me not a dick I would have any sexual interest in. I think this helped to excite him as I clearly saw a thick drop of precum bubble out of the little eye of the small red head of his slender dick.

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"So, Liam, tell me one of your stories about being a sissy cuckold. Have you ever sucked another man's cock?"

Liam: "Ms Stevens, I am not gay, I am not attracted to men at all, I love women and how beautiful their bodies are, how beautiful a woman is. You, Ms. Stevens, I think you are a truly beautiful woman and being made to stand here in front of you, naked, is totally arousing as you can probably tell," his eyes dropped to signify his now drooling little dick. "However, as a true submissive there is probably nothing, I find that shows more, how submissive I can be than to be kneeling in front of a big strong muscular man, in my little pink panties and have to suck his cock."

Yes, as a true submissive myself, although as this shows I can also switch, I agree being on my knees, preferably naked or as with Liam in a sexy pair of little panties, in front of a big thick cock, especially a big black one, would get my little pussy dripping. He and I were not so dissimilar. Just the fact that he was a beta sissy male. I wanted to test how obedient he was.

"Sissy, go to the sink and pour me a glass of water. He turned and I watched that cute, almost girlie little round bum undulate as he walked across to the sink, took a glass and filled it with water. He then carried it over and I watched his hard little dick sway slightly back and forth. Not the way a true alpha cock would sway, it just wasn't big or long enough. But it did have a nice little cute swing to it as he walked.

"Sissy, do you like pretty fully clothed women watch you stroke your little dick and watch as you squirt your cummies."

Liam: "Yes of course Ms. Stevens, that's one of my favourite things."

"Do you clean up afterwards?"

Liam: "If I'm told to Ms. Stevens."

"And, have you ever had a real man's cock up that slutty little girlie arse of yours?"

Liam, looking down at the floor with some shame: "Yes, Ms. Stevens."

"I think you have more than one story to tell."

I stood up and walked around him. I could see the very red head of his below average dick throbbing with the excitement of being circled by a stunningly attractive fully dressed young woman. I ran my hand down his back till my small finger stroked gently over what was a surprisingly round bubble butt. I would say his small ass even looked a little girlie.

"You're shaved and waxed all over?"

Liam: "Yes, Ms. Stevens."

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"Show me."

Liam turned to give a quizzical look, not sure what I meant.

"I want to see if your ass crack is fully waxed. Bend over and reach back spread your cute little bum cheeks for me."

Liam did exactly as he was told, yes, he was completely submissive and, yes, he was totally hair free.

"You shave and wax yourself or does the delightfully mean Cassie help?"

Liam: "Sometimes Casie will help me but I she also sends me most week to a beautician and the girls there shave and wax me."

"So, at the beauticians you strip as naked as you are now, and the girls shave and wax you?"

Liam, looking down at the floor in some embarrassment again, "Yes, Ms Stevens."

I wrapped my hand around his little throbbing knob, "And when you're being shaved and waxed by the girls you get as hard as you are with me?"

Liam: "I get very hard, but being in front of you today, I am especially aroused, as you are so beautiful."

I let go of his little dick and walked back round behind my desk. My pussy was throbbing at the pleasure of teasing this beta young man and I wanted to hear more.

So, tell me the first time your lovely girlfriend dressed you as a sissy.

Liam: "The first time I didn't even realise I was being dressed as sissy. I thought it was just fancy dress, until I got to the party and realised, I was the only guy there dressed as a girl. I should tell you, Ms. Stevens, if you will allow," he paused, I nodded, "Cassie very quickly realised I was submissive, and she had cuckolded me within the first six week of our relationship. My older brother had come to stay over for the weekend and without giving too many details I ended up in the spare room listening to them fuck the first night of his visit. Then as a true cuckold submissive I would wait on them all weekend and on the Sunday while we sat watching tv, I got to see my beautiful Cassie having sex with my brother.

In the next chapter Liam tells his story.

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