High Society Sissy

I guess I can say I was one of the lucky ones. Fresh out of an ivy league school with a degree we were met with two different tales.

"Sorry, you're over qualified," they said.

Or we would hear, "We're looking for someone with more experience."

An alum that I had befriend however was able to land me a waiter position in a posh New York country club that catered to the financial elite. The hours were horrible but obviously the tips were fantastic. Not that I could complain about the hours though. I was always the shy and introverted type. You wouldn't find me at the club or bar on a Friday or Saturday night anyway, so why was I complaining?

Another side effect of my personality was my inability to get any where with the female gender. Probably the only one to make it through college, the era of partying, and still remain a virgin. I would always tell myself I was straight too, but would sometimes catch myself staring at the odd male. I would quickly dismiss such actions, but the inkling was clearly there.

Most of the members of the club fit the stereotypical banker arch type. Rich older white men in suits, polo shirts, or the latest atrocious golf fashion. Most of them clearly did nothing for me, however, he was clearly different. An African American gentlemen who looked like he was in his 30's, but was probably older than he looked. Clean shaven, athletic physique, I definitely caught myself looking a few times. I soon found out things would be mutual. Whenever I came out to serve or bust a table, I would catch his gaze through my peripheral vision. Usually it just was subtle glance here and there. Soon, however, they turned into longer glances; appreciative glances.

Unable to look in his direction, finding myself flustered. Why did it bother me so? I was being harassed, wasn't I? That's what I would tell myself at least. Wondering how much longer I can go in day after day, I soon got my answer. My presence was requested at his table, and not as a waiter, but as I guest. And it was made clear I would be looking for another job if I didn't join him.

Walking to the secluded corner table he was at, a giant pit forming in my stomach and growing as I got ever closer. As I took my seat, he was already pouring two glasses of champagne. Three hundred dollars a glass, more than I would make in a night...

"Thank you for joining me," he said as I finished positioning myself comfortably in the chair while reaching for a glass. Lord knows I was going to need something for my nerves. I immediately took a sip without even responding to his thanks. I quickly looked up feeling as though I was being rude, but for some reason it brought a smile to his face. I was content to leave it at that.

"You are very pretty." he said, causing me to slightly choke on the champagne I was still in the process of swallowing.

Clearing my throat I found myself staring down at the table in front of me, feeling my cheeks starting to blush as I meekly replied, "thank you."

"Most men wouldn't take that as a compliment," he retorted with a grin.

My eyes kept darting back and forth from his face to the table in an attempt to read his face while simultaneously trying to hide my embarrassment. He was right though, most men wouldn't take that statement as a compliment. Of course, considering I couldn't grow a beard, had no chest hair, and was only 5' 5", who was I to argue?

"It's okay," I replied as one hand nervously played with my napkin while my other brought the rest of my champagne to my lips.

Refilling our glasses his next question was the one I was dreading "Are you attracted to men?"

My face was probably beet red by now. I could feel the heat in my cheeks as I searched in my head how to answer this question.

"I don't know." was all I could come up with.

Immediately pouncing on my response with, "You don't know?", a sense of surprise in his voice, I immediately took this as a cue to finish my second glass. There was an awkward silence as both of us were clearly waiting for the other to say something else. He began to stand up, saying, "I think it's time to wrap things up here."

As he began to walk by me while I was still seated, thinking I was in the clear, he turned slightly, holding his hand out, "Will you be joining me?"

Looking down at his hand, all I had to do was politely say, "No thank you," and it would all be over. However, I found myself placing my hand in his, standing up as his hand pulled up at mine. The whole time my inner monologue is telling myself "No, you don't have to go with him. You don't want to go with him." But do I? In the end I followed him out to his car, still hand in hand, myself walking slightly behind him.

Nothing was said as the limousine drove us to our destination. He simply sat across from me, once again devouring me with his gaze. It was then that I realized that he never asked my name, or gave me his. I didn't dare break the silence. The silence was maintained as we entered his mansion and made our way to the second floor bedroom. He put his hand up as if for me to stop in the middle of the room. As he continued on to a secondary room he said over his shoulder "Remove your clothing please"

I removed my shirt, shoes, and pants now finding myself only in my socks and boxers as my ears scanned for any indication of where he was or what he was doing. He returned from the other room, completely naked and holding a duffel bag. Besides noticing his chiseled physique; six pack abs and nicely cut arms and legs, I also noticed his flaccid cock, and that it was already quite large.

Upon seeing me, he furrowed his brow and made a circular motion with his hand as if to say, "You didn't finish yet!" Now completely naked I notice he's already sitting in a large cushioned chair with large arm rests. With a finger wiggle I'm summoned to stand directly before him. As I reach his seated position, his hands are down low holding open wide a pair of white panties. A quick wiggle of the panties tells me he expects me to step into them. While he slowly slides the panties up my now quivering legs I think to myself "Why am I doing all this? Can I not resist his commands?"

With the panties now secure around my waist he quickly runs a finger from both hands around the inside of the elastic waist bang to make sure they are snug and in place. The panties are a bikini cut with a scalloped lace design and a little bit of frilly lace along the waist and leg bands. His hand lightly slapping on one of the arm rests beckons me to sit down on it.

His hands are now holding a rolled up bit of white material. Starting at my toes, his hands slowly and tightly roll it up my leg, and as he reaches the top of my thigh I realize they are sheer stockings with a thick scalloped lace band at the top. A band of silicone inside the stocking keeps them securely at the top of my thigh. The process is repeated for my other leg. The last thing remaining in the bag is several pair of black high heels. They are pumps with a strap that goes over the top of the foot and a four inch heel. Once he finds a pair that fits they are buckled securely onto my feet.

Directing me to stand in front of him with his hands, all I can do is nervously look down as my brain is over loaded with how fast I've arrived in this position. "This is what I truly meant when I said you look pretty," he said.

I look up and give him another one of my meek thank yous.

"Thank you, Sir," his lips emphasizing sir.

"Thank you, Sir," I correctly responded.

He runs one of his hands down my chest while asking "Do you shave or are you naturally hairless?"

"Naturally hairless, Sir."

His hand makes it down to my panties and I find a finger rubbing my penis through the lace material. "Have you ever fucked a woman before?"

"No, I am a virgin, Sir."

Leaning forward, resting an elbow on each knee, he begins to rub his fingers on the insides of my lace covered thighs. As he teases my thighs he looks up at me and states quite sharply "So you've never fucked a woman, you don't know if you're attracted to men, and yet you're excited about being dressed in lingerie before another man..."

I close my eyes in shame as once again my face is on fire from the blushing and embarrassment combined with my arousal overwhelm me. I hear him as he leans back in the chair heavily. He asks, "Do you know what a sissy is?"

"A wimp, Sir?"

"Ah, yes, but no!" he replies with a bit of excitement. "A sissy can be many things. For instance, in the world of fetish a sissy is usually some form of effeminate male. Would you agree that you are some what effeminate?"

"Yes, Sir," I replied.

"So if you admit you are effeminate, then that would also make you a sissy, yes?"

I'm not sure if he was right. I'm not sure if he was serious or playing some kind of game. However, a part of me was curious to see where this would go. "Yes, Sir," I conceded.

"Yes, Sir, what?" he quickly retorted.

"Yes, Sir, I am a sissy," I said as I looked up to see his reaction to my admission. His grin could be described as that of a cat who has a mouse right where he wants it.

Still leaning back in the chair he quips, "Since sissy has been so amendable to my logic, and dressed so pretty for me, I shall allow sissy the honor of worshiping me."

Upon completion of his statement he slowly opened his legs. This movement caused me to refocus on the cock between his legs that I had briefly forgotten. By now it was fully erect and probably stood at 8 inches long. I knew he wanted me to suck his cock, but if only it was to be that easy. I slowly knelt down between his legs, the fear and anticipation of what was to come made everything seem like it was in slow motion. I grabbed the base of his cock and slowly began suck it into my mouth. I was a little worried at how easily this was all transpiring, but suddenly--

"No!" he exclaims as he pulls the cock from my lips. "No no no, I said worship my cock, not suck it!"

I just knelt there with a confused look on my face. Sighing, he says "Alright, Place both hands on your thighs." Placing both hands on my thighs he continues, "Starting at the tip of my cock head, begin placing soft tender kisses, working your way all over the entire head."

"Good, good," he encouraged as I lightly kissed his increasingly swollen and throbbing cock head. "Look directly into my eyes as you worship my cock," he said, "So I can read the passion, lust, and submission in them."

Normally I have issues making long term eye contact with people. In this case however, at his command, my eyes were now locked onto his. No matter how I turned or bobbed my head to kiss his twitching cock, my eyes remained focused on his. A large smile on his face told me I was doing a good job both with worshiping his cock and gazing into him.

"Now begin to flicker your tongue over my head, and place deeper, more passionate kisses," He instructed. I found myself instinctively cooing each time I licked his cock, and the deeper kisses made a nice loud smacking noise. Each time I pulled away from his cock I could see and feel little strands of saliva bridging from my lips to his cock.

As I continued to unleash this new torrent of passion onto his member I felt his foot tap the insides of my knees. My legs reflexively responded and spread further apart. His foot then began to rub the now quite apparent bulge in my panties. Pulling his cock back while tapping the bulge he inquires, "What is this?"

"My penis, Sir," is all I can think to say.

"Sissies do not have penises my dear, they have clits," he instructs. "So once again, what is this?"

"My clit, Sir."

"I know that sissy, but what is it doing?!" he said with sarcasm thick in his voice.

Having to be quicker on the uptake least he get angry with me I demurely reply, "Its throbbing and leaking, Sir."

"That is correct, sissy, but why is it throbbing and leaking?" he replies, still not content with the answers.

What is he trying to get from me by asking all these questions and admit all these things? Or is this part of what gets him off? I must admit though, while embarrassing to admit these things to him, the shame is also met with more arousal. "It's leaking and throbbing because I'm horny, Sir."

"That's correct, sissy, because you're horny. Now, open your mouth and hold out your tongue," he commands. Holding his cock, now glistening with my saliva, he begins to lightly tap it up and down on my tongue. He continues "And sissy is horny because it likes worshiping cock, likes dressing up, and likes being a sissy, correct?"

I manage to get a yes sir out in between the taps of his cock on my tongue. With that, he stands up walks over to the bed. He sits down on edge and pats his hand down next to me to signal he wants me to join him. I was still kneeling and hesitated as I looked at him with worried eyes and my hands entangled in a nervous mess. Does he want to have sex? Does he want to fuck me so soon? Sucking cock is one thing but I've never had anything in my ass before.

"If sissy wants to leave," he begins to say, "The door is over there," his hand now pointing at the door. "However, if sissy wants to stay, sissy needs to obey my commands without hesitation."

I stand up and zigzag my way over to the bed. Between the pit in my stomach weighing me down and my uneasy feet in the unfamiliar heels I about fell over. He now has a pillow near him and instructs me to lay on it. "Lay on the pillow so that it is directly under your crouch," he orders.

"I have been patient with sissy up until this point, but now there has been too much hesitation," he bellows in a stern tone. "Therefore, sissy must be punished. Sissy will present its ass and will not pull away from any blows, understand?"

"Yes, Sir," was all I could reply. He was going to spank me for real, and all I could do was lay there and wait for him to do it.

*Whack!* came the first blow on one cheek. His hand large enough to cover the whole thing. It stung, hurt a little, but I could tell he pulled the first one.

*Whack!* on the other cheek. This one harder than the first. This continued for five blows on each cheek, each one getting progressively harder. I cried out on the last two and tears began to well in my eyes. As I now lay there still taking in what happened and recovering, he began to massage my sore but now sensitive cheeks through the lace panties.

"Sissy did good in receiving its punishment," he beamed.

"Thank you, Sir," I was quick to reply.

He pulls the pillow out from under me, and pulls at the tops of my thighs as if he wants me up on my knees. I start to get up on my knees but he now places a hand on the top of my back and pushes back down, so that I'm sticking my ass up in the air while keeping my face and chest against the bed. He spreads my knees apart as far as they can go in this position so that my ass is sticking straight out and is completely exposed. I feel him begin to peel my panties back and then down so they are now half way down my thighs. I feel cool air on my asshole as this extreme kneeling position while bent forward naturally pulls my cheeks apart.

I feel a finger begin to trace the spot at the base of my scrotum all the way to my asshole, while his other hand begins to methodically grope and pinch in the insides of my thighs. His expert hands continue this assault of stimulation on my sensitive areas until I can feel another generous flow of pre cum flow from my clit. His finger massaging my ass retreats briefly but quickly returns, wet with what I can only assume is his saliva. The finger begins to test the tightness of my asshole. Once satisfied that it has been aptly stimulated and lubed, he whispers to me "Just relax your muscles," and I feel his finger slowly and gently push inside me.

His other hand has now assumed a position under my clit while his finger continues to work itself in and out of my ass. As he continues he says "You may start to feel a tingling sensation, almost like you need to pee, just let it go."

This continues for maybe half an hour as I continually feel little spurts and dribbles. Its almost as if I have an itch on the inside of me, and he is scratching it in just the right place. He beckons for me to arise and when I do I'm greeted with his hand containing a puddle of my juices.

"Dessert?" he asks as he holds it up to my chin. I dare not disappoint him again. Although, at this point I'm so sexually charged my inhibitions are all but gone. As I begin to lick and suck at my juices all I can think of is how dirty and naughty this is, yet I can't resist it. I haven't been able to resist any of it. As I finish he is now standing at the edge of the bed and stroking his cock with his other hand.

"There's still one more, might as well keep your mouth open," as his other hand now joins in on stroking his engorged member.

I position my open mouth at the tip of his cock and once again lock eyes with his as he gets closer and closer to climax. Judging from the contortions of his face and I can he is close just like that the spurts hit the roof of my mouth with force I wasn't prepared for. He quickly fills me before I can start to swallow, and I can help but notice how much thicker and hotter his juice is than mine. Once finished swallowing down the last of his seed, I cleaned the remnants from his cock, gave his cock head one more loving kiss, and said, "Thank you, Sir."