The Birth of a Sissy Pt. 02

Upon my return from Orlando I was tasked with making a decision of where I would go to school in the fall. At first I was intrigued by the possibility that I could go the University of Central Florida, but quickly remembered that I had never stepped foot on the campus while in Florida. So it was a decision between the schools in little old North Carolina, at least the ones that I had the grades to get into (sorry Duke). Within a few months I had settled on UNC-Charlotte home of the fighting 49ers. The excitement that I would be a small fish in a large pond had its appeal. If I had learned anything from my trip to Orlando it was that in a big city no one cares what you do with you.

As a condition of moving to such a big city, I had promised my parents that I would stay in the dorms on campus. It was a bit of a let down because I was looking forward to having a place of my own to live like I wanted, but it would also save me from unexpected check ups from my mom. So I moved in with my new roommate Tim, a nice enough guy, a bit too much into the LARP scene for me. I guess we both liked to play dress up though. I settled in and started my life as a run of the mill college freshman, who kept a full wardrobe of women's clothing in the trunk of his car and a literal tackle box full of make up.

I worked at a campus coffee shop in the afternoons following class. It wasn't much but on pay day I would drive 20 minutes to a mall away from campus and buy something new and pretty to wear. On Friday nights I would drive downtown to the business district and slip into my newest purchase, doll myself up and slide on some short heels (I was getting the hang of heels finally). I would slip up to the bar and order a tonic water with lime. It gave the appearance that I was drinking by myself and within a short time someone would send me another. I would smile and nod my thank you to the gentleman. Then I would wait for his liquid courage to send him my way.

It was very rare that the first gentleman to approach was looking for my brand of companionship, but eventually the word would spread that the "hottie" at the end of the bar was more than meets the eye. A lot of the time I was invited to a parked car in the garage. Though I had become skilled at giving head, it was not what I really wanted for my nights out. Don't get me wrong if the gentleman was a particularly endowed friend I would gladly take them up on the offer. I would hold out for something more adventurous to come my way on most nights. Some nights took longer than others but every night ended with what I was looking for.

I had learned more of what it meant to be a sissy. I had begun to enjoy the dominant role that my suitors took. Telling me how and where to do their bidding. I was blossoming into the person I had been hiding away for so many years. The fun things that traveling business men want to do, but apparently can never ask of their wives astonished me. I had peed on more people than I care to count. I was also becoming quite the power bottom, learning how to position myself for maximum penetration and performance. I also had a couple of local gentleman that liked to buy me lingerie to wear while they fucked me. I'm pretty sure that one of the gentlemen would take the lingerie home for his wife afterwards.

All in all things were going great for me. School was school, the job was a job and my weekends were my vacation from the constrictions that society wanted to place on me. By the time spring semester rolled around I had a 4.0 and was cruising towards a bachelors in economics. Then I encountered Dr Thomas, Advanced Statistics professor and overall unhappy human. This guy was mid 50's, about 5'6", and probably 20 lbs heavier than he should be. The best I could figure was that he was tenured, had a miserable home life and was hell bent on failing half of his classes. He never graded on a curve as he made glaringly clear on the first test that he gave us three class's into the semester. To the best I could surmise he probably had a little dick that no one had touched until he had his PHD and the first girl who did he married.

I was in such a foul mood when I stepped into the bar on the Friday night that first weekend in February. I had put on a super sexy and flirty pair of matching plum colored thong & bralette. I had on a really cute gray dress that went to mid calf and a pair of nude knee highs. Topped off by my auburn colored wig I was stunning, if I do say so myself. I had hoped that getting so prettied up would alleviate my funk but it didn't. While I sat at the bar with my tonic water I just stared into the glass. My mood must have permeated the space around me and I had not received a drink in the hour I sat staring into the bottom of my glass. I was oblivious as he pulled up a seat next to me.

"I know I've seen you in here before, but I feel like I have seen you somewhere else too?" His familiar voice snapped me out of my trance.

I glanced from the corner of my eye to confirm my suspicion and sure as I live and breath, just inches from my left shoulder sat Dr Thomas. Oh god what fresh hell was he here to unleash on my last bastion of goodness. Wait did he say he had seen me here before? It was very plausible that I had paid him little to no attention this entire time.

"Yeah I have seen you at a couple of other bars in the area, but I can't quite place where. Do you go to the university?" He said as he leaned in to get a better look.

I still hadn't turned to face him. He had seen me at other bars too. Had he sent me drinks in the past? Did he hear the rumblings of the other frequents that I was more fun than some were looking for? Did this guy not know the meaning of personal space? He smelled of the cologne Chrome and was no longer wearing the trademark ugly blazer with the pretentious patches on the elbows.

"Oh shit you are one of my students!!" He said loudly. Whelp now all the eyes in the bar were on us.

"Yeah maybe" I replied in a loud whisper "and maybe we shouldn't broadcast that for the world."

"Wait aren't you one of my male students?" He said in a hushed tone that I was thankful for.

At this point I turned and looked him dead in the eyes. His eyes widened into a surprised look. I had never bothered to notice that he had hazel eyes to go with his salt and pepper hair.

"Isn't your name..." I cut him off quickly "it's Katie if you want to continue any conversation in this bar."

"Well Katie, I um, I've heard some things about you from some other people around here."

"And that has what to do with you?" I retorted, hoping maybe he would catch the hint that I was not in the mood to talk to him.

"I was just hoping I could buy you a drink and maybe chat you up a bit, but knowing you are a student I should probably walk away huh?" He said as he hailed the bartender. "Whatever 'she's' drinking is on me for the night." He then turned and walked back to a table by himself.

Within seconds of him walking away I began to become enveloped in "southern guilt," I had been raised a southern gentleman. Polite and courteous, don't show your ass in public. Katie should probably in turn be a southern lady and at least thank the gentleman for the gesture of kindness. So I picked up my fresh glass of tonic water and walked over to his table. "Is this seat spoken for?" I asked as I reached the table.

"No, by all means sit." He said as he lowered his cell phone to the table.

"Sorry for being so rude, it's just I've been a little stressed, I have this professor that's a real ball buster!" I said with a huge grin, hoping he would take the joke and the little pun.

"You don't say? I have to drink because of all the subpar students I deal with on a daily basis" he chided back.

"Sounds like a real Hatfield/McCoy situation we have ourselves in then." I shot back at him. This time he smiled and for the first time I saw him as a real person, not just a disgruntled prick hellbent on making my life miserable.

"I'm Matthew by the way. And you are...?"

"Katie, like before at the bar." I said as I extended my hand.

"So what brings you to this bar?" He asked.

"Better question is what brings you to a bar in the business district?" I quipped back at him.

"Well I didn't always teach. I used to work for one of the financial institutions around here. Then my wife got sick of me traveling all the time. Probably because it made me happy. So when a position opened up at the university I took it." Holy shit I had this guy pegged all along.

"I used to meet up at these bars with all of my buddies to keep up on the ins and outs of the business world, but little by little they have all met their retirement goals and stopped coming out with me. Tenure is nice but I can't retire yet." He said as he trailed off. "I guess I just come out now because my wife lets me have one night a week to myself."

Just like that I felt sorry for the bastard. I was right about him, but all of a sudden I felt bad for being right about him. In a gesture of sympathy I put my hand on his knee. He just looked so pitiful that as a human being I wanted him to know that he was not alone. That simple touch must have been all he needed to feel in touch with humanity. He leaned across the table and kissed me. I pulled back in surprise.

"I um, I um... I am sorry I just thought that we had a moment there." He stammered as he turned flushed.

"Well I guess we kind of did, I just didn't think it was that kind of moment." I said as I too began to blush. "You do know who I am right?" I asked as he looked at me with remorse for what he had done.

"Yeah, I do. I have also heard a bit about your reputation around here as well. That's why I got the nerve up to come talk to you earlier. I am just so desperate for some carnal human contact. I was just hoping that maybe you could help me out. Knowing that you are one of my students I shouldn't have let it get to this point, but I am so lonely. Tonight I was supposed to meet a couple of the guys I used to work with, but hey bailed on me for the second week in a row." His tone was so morose.

Here I was, i had been talking to him for over an hour and my previous demeanor had chased away other possible suitors. Was it worth the risk to just take this poor bastard out to his car and blow his tiny little prick? Who knows maybe if I did it well he would lighten up on me in class. Worse case scenario I alerted his department chair of our tryst and he would get reassigned or something. It was probably worth the risk. So I placed my hand on his knee once more and ran it up his thigh as I leaned over and kissed him. As I approached his mid thigh, mid kiss I felt something pulse beneath my hand. Holy shit I was wrong about a tiny prick. I ran my hand a little further up and was running my hand on his semi rigid cock. That was just the beginning of one of my best nights.

"Hey so you wanna get outta here and maybe head to your car?" I asked with some excitement in my voice.

"Um, actually I have somewhere close by that we can get more comfortable in. My buddy is out of town and I cat sit for him at his condo. It's just another excuse I use to get out of the house." He said with a pleasant smile on his face.

We walked a few blocks south and entered a large condo building. As we entered the elevator Matthew took an opportunity to pat me on the ass. On the 16 floor elevator ride he held my hands and kissed my neck gently. As we debarked from the elevator he took me by the arm and we strolled arm in arm down the hall to 16E. He opened the door and gave me a gentle guide inside with a firm hand on my ass. I have to say that by now I was getting into this whole little game we were playing. He flipped the lights and the place was amazing. There was a beautiful floor to ceiling window that looked out toward the east side of the city. As I looked out on the city I caught a glimpse of Matthew in the reflection of the window. This little eager beaver was already taking his clothes off. Obviously he was intent on getting his rocks off. I was convinced that he had probably not busted a nut with someone else in a very long time. I turned around to face him and as I did he had put a tight grip on the back of my neck and had turned my face back to the window. I took the hint and faced back to the window. He lifted my dress above my stomach exposing me below the waist all while keeping a tight grip on the back of my neck with his left hand. He bent me slightly forward and with his right hand gave me a swift and authoritative smack on the ass. The instant sting made me moan.

He released my neck and grabbed my waist, this time his spank was a solid one that hurt in a pleasurable way. Without saying a word he pulled my panties to my ankles and commanded me to step out of them and remove my heels. I did as I was told. Matthew then picked up the panties and pulled my right hand behind my back, tied my wrist and yanked my left hand back. He secured my wrists behind my back with my thong. He pushed me against the glass, mashing my now erect cock against the cool glass. With the bottom of my cock on cold glass and the top of my cock against my warm belly I couldn't help but moan in pleasure. This must have pleased him because the next slap on my ass was his erect penis across my warm right cheek. With his right hand on my bound wrists and his left hand back on my neck he spun me and marched me to the couch. He plopped me down and pushed me into a recline with my head off the edge.

I watched in amazement as his eight inch cock passed over my face. He was at least two inches thick with some of the most impressive veins I had ever seen on a cock.

"Open your mouth slut." He commanded as he lowered his balls into my mouth. "Time to clean daddy's balls with that sissy mouth of yours."

I reveled in the saltiness of his sack as I used my tongue to juggle his balls in my mouth. I felt the base of his cock as it spasmed on my chin and with in seconds I felt as he blew a hot load on my chest. He let an animalistic grunt escape as shot after shot exploded from him. I applied a gentle suction to his sack causing his balls to rub against each other in my mouth. While he exploded it took everything in my power to keep his balls in my mouth as they jumped all over the place releasing loads onto me. I felt as his penis began to go limp and hang to the contour of my neck. The spasm of his cock and balls stopped and I released my suction. He stood and removed them from my mouth. A cell phone rang and he left me laying there as his hot load ran down my chest towards my stomach. I could hear him speaking on the phone but could not hear the conversation. I assumed that the tone of his voice he was not talking to his wife.

"Well that was a pleasant surprise!" He said as he returned to the room.

"What kind of pleasant surprise might that be!" I asked.

"Well that would be of no concern to a cum covered sissy at this time." He retorted. "Now it's time to get daddy hard again my little fuck toy!" He wiped his load from my chest with a towel from the kitchen. He then stood over me lowering his limp cock to my forehead and placing his balls across my eyes, lowered his asshole towards my mouth. "Time for your tongue to explore daddy's asshole slut!" With that command I began to lick his asshole. Making circles with my tongue and pushing pressure on his sweet pucker. He groaned his approval and within two minutes he was erect again. He lifted from my face and pulled me by my shoulders to a seated position, then to standing, he reached down and pulled me towards the bedroom by my hard on.

Once in the bedroom he removed my panty handcuffs and shoved me onto the bed. "Face up slut!" He commanded and I obliged. He removed my stockings and used them to secure me to the bed frame. He then retrieved a tie from the closet to my left. He blindfolded me and stuffed the cum covered towel into my mouth. He then proceeded to wrap my thong around my balls and shaft creating a cock ring. Blinded, muted and restrained I laid there for several seconds while he busied himself around the room. I then felt the cool oil as it slid down my balls into my asshole. I felt him jerk my legs into the air and then my knees back up to my chest. With no "hey how you doing" Matthew began to maneuver his massive snake into my ass. Don't get me wrong I have accommodated a few cocks recently, but his was a specimen to behold. I pushed back in an attempt to help ease him inside me. Slowly but surely he had entered me, I felt every vein as it stretched my hole to its fullest. After about five slow withdrawals and thrusts my fully stretched sissy pussy had become acclimated to his girth. Matthew began to pick up his pace into a steady pounding. Through my salty gag I began to moan my pleasure as he took out his sexual frustrations on my ass.

With Matthew getting into me with such zeal, I had begun to be lulled by his steady rhythm. I was a bit surprised that the gag was pulled from my mouth. "Oh daddy, this ass is all yours, please fuck it harder!" I expressed. With his cock still in my ass I was surprised to smell the musk of a cock near my nose. What was I missing? Then without warning the tip of a cock pressed against my lips. I opened my mouth with the intent on asking what was happening, but as I opened my mouth it was filled with a swollen member. I was so confused, there was definitely still a cock in my ass and now one certainly in my mouth. Within seconds the cock in my mouth began to withdraw and then slammed to the back of my throat. Natural instinct caused me to gag.

"Yeah Danny fuck that sissy's throat!" Was what I heard Matthew say as he grabbed my hips and drove himself so deep and hard into my ass.

There was obviously someone else in the room with us and his presence in my mouth had filled Matthew with renewed exuberance. This new cock began to thrust and withdraw from my mouth in a different rhythm than the one in my ass. The startling reaction to this new penis in the party began to wear off and I began to do my best to accommodate my new flesh gag. After a few minutes of having both holes filled, my two daddy's began to synchronize their strokes. It was glorious!! I had failed to notice how hard my own cock had gotten with all of the pressure on my prostate. Within a few seconds of that realization, I began to erupt onto my stomach. Apparently this pleased Matthew and he in turn unleashed a torrent of cum into my thoroughly fucked ass. I have to tell you that the release into my ass sent me to the moon and I released the deepest moan I had ever before and probably since. With that the mystery man in my mouth blew a wonderful protein shake into the back of my throat. Without a word otherwise both men withdrew from me, leaving me empty. I laid there tied and blindfolded for some time, with a hot load on my stomach and cum dribbling from my ass. I had been treated like a complete sissy fuck toy and I loved it.

I could hear both of them talking and laughing together in the other room, but again could not make out the conversation. This had to be the person that Matthew had spoken with on the phone. A few minutes later I felt the knots loosen from my wrists and the tie was removed from my eyes. It took a seconds to focus and there stood Matthew with a huge smile on his face, his hazel eyes glowing, he appeared to have gotten younger since the time I had last seen his face. He was still naked and even limp his cock was impressive.

"Danny says you can use the shower to clean up. Get dressed and get out of here kiddo!" He said with a wink.

I did just that. Cleaned and redressed I headed for the door still wondering who Danny was and where he had gone following our little threesome. From what I could gather this was his place and he had come home from business early. Whatever the case may be it was a blast. As I reached the front door Matthew grabbed my ass cheek and pulled me in for a deep kiss. He opened the door and without another word pushed me into the hallway. As the door closed behind me I let out a sigh. It had been one of the best experiences of my life.