The Birth of a Sissy

By my sophomore year of college I had performed well enough in the class room that I had earned a few scholarships. This meant that my folks were saving money while I was getting my learn on. It also meant that my dad had promised me that if I rode it out for one more year in the dorms that by my junior year I could move off campus. The thought of finally having a place to call my own and be free to wear almost full time was all the motivation I needed. As I settled into my hectic schedule of class, work and an active weekend social life I started to feel at ease. I had learned a lot in my freshman year and become quite efficient with my daily hustle. I had begun to pick up some more time at work, trying to save up as much money as I could for my eventual move off campus.

In the process of working more I had ingratiated myself to the owners of the coffee shop. They were a wonderfully generous and happily married couple with long standing family roots in the Charlotte area. Mike and Kim had become my Charlotte parents. They had two daughters and a son, all under the age of 10. They had extended me the kindness of joining them for Easter dinner when I couldn't get back home because of finals. Mike was a handsome man in his late thirties, slightly taller than me at 6'3" and 240lbs on a linebackers frame. Kim was smoking hot though. She was about 5'7" slender frame and incredibly fit. She had been a cheerleader in college at NCState and even after three kids she was in great shape. She was oft seen swinging in for a latte before she headed off to the gym, sports bra struggling to hold her d cup breasts and a tight pair of yoga pants accentuating her sculpted ass. She was everything I wish I was when I dressed.

As fall began to settle in, in NC, Mike and Kim decided to take there happy little family out to there cottage in Hatteras for one last week away before it got to cold. So on Thursday as I was cleaning up after close Mike approached me and asked me for a favor. He and Kim would be grateful if I could house sit for them while they were away. I couldn't think of anything I could have wanted more than to help them out and blurted out a yes before Mike had even finished asking. I was going to get a week away from the dorms, a whole week where I could walk around in my panties, a whole week where I didn't have to hear my new dorm mate Alex snore all night. It was going to be my "dress rehearsal" for when I had my own place and it was going to be perfect.

Mike and the fam set off for the coast on Saturday morning and I was there to see them off. I had accepted the first offer for companionship at the bars the night before so I could get home early and get a good night sleep. I wanted to be bright eyed and bushy tailed for Mike and Kim when they left me with there home for the week. Have no fear I was here to take care of it all. Mike had even given me the key to the drop box at the bank so I could drop the weekend deposit. This was what being a responsible adult felt like and I loved it. Shortly after they set off on their happy family adventure I backed my car into the garage. I busied myself familiarizing myself with their home, how their remotes worked, which rooms had windows that the neighbors could see in. Around noon I ran out and got some lunch, I had on a pair of hot pink spandex boy shorts on under my shorts. When I returned to the house and parked in the garage I unloaded a sizable portion of my trunk panty collection into the spare bedroom. I took quite a bit of time putting on different panties and parading around the house. I watched a little Sports Center on the couch in a pair green bikini cut panties and some black thigh highs. It was heavenly.

For dinner I ordered a pizza and answered the door when it arrived dressed as Katie in a cute floral pattern summer dress. I am pretty sure I had fooled the teenage boy dropping the pizza off. After a couple of slices I walked upstairs to the my bedroom and slid out of my get up. As I pondered what to wear next a thought crept into my head. I don't know what made me act on my deviant thought but I did. I walked down the hall to Mike and Kim's master suite and flipped on the lights. I proceeded to open the drawers in the dressers until I found Kim's panty drawer. Inside was a menagerie of the nicest panties I had ever seen. This woman had every pair that Victoria Secret had ever made. Colors, cuts and fabrics I had always imagined owning myself some day. I reached in and pulled a pair of light pink, bikini briefs with lace at the top and a cute little keyhole with a ribbon in the back. I slid into them and immediately fell in love. They were soft and sensual, this is what it felt like to be a woman as confident as Kim. With no trouble at all I found a bra that matched the panties and slipped it on. Heading to the closet I could feel a bounce in my step. Inside the walk-in closet was myriad of beautiful dresses, skirts and blouses. It was a complete sensory overload for me.

I tried on five or six outfits before settling on an amazing, tight little spaghetti strapped red micro dress. Looking at myself in the full length mirror I looked so pretty, I could only imagine that Kim looked drop dead gorgeous in this number. I walked back to the dresser and began to search for some nylons to wear. I found some sexy black thigh highs and a super lacy garter belt. I could only imagine the line of business men that would be lined up to fuck me silly in this outfit. I bounded out of the bedroom and downstairs to the living room. I snapped a couple of selfies with my phone and spread out on the couch. I settled on a show on the tv and laid back to relax. The temptation to head out on the town was so unbelievable. I had on a pretty face and my blond shoulder length wig. I would have been the most popular girl at the bars, but I could not risk anything happening to Kim's things. So I just laid there as the show droned on and admiring the way my boner looked in the tight red fabric. I must have been more tired than I thought because at some point I dosed of. I never heard the door from the garage into the house open and close. I most certainly didn't hear Mike walk into the living room, well that is until it was too late.

"And who the fuck are you supposed to be?!?" Came the startling voice from the doorway between the kitchen and living room.

I froze in utter terror. "Umm... Ummm... Oh my god I am so..." Sorry? Busted? Fucked? I couldn't even finish the sentence because of all the thoughts flooding through my head.

"Why in the hell are you wearing women's clothing? Are those my wife's clothes? Oh my god are those my wife's panties?" He was still standing in the doorway as he took in the scene that lay before him.

"Well... I just... What are you doing home?" I stammered and then began to panic that if he was home the rest of the family was home too. Oh god how would he explain this to his kids. I was totally fired for sure, but that was probably the least of my worries. I began to sit up. To make any attempt to exit this horrible situation any way possible.

"Oh no you don't. You stay right where you are at. You have any answers for why I walked into my house and found you all sissied up?"

I was on my elbows and able to look at Mike from my angle on the couch. For as mad as I thought he sounded he was standing in the doorway cool as a cucumber with a smirk on his face. His calm at that time eased some of my trepidations and I slid myself into a seated position on the couch. I truly couldn't help but notice that his khaki shorts seemed to be poorly disguising a semi erect cock. I took a risk and finally answered him without stumbling over my words.

"Don't pretend like you didn't want to come home to something like this some day! Why exactly are you back so early? Where are Kim and the kids?" Now I was starting to demand answers from him.

"Well little Lisa forgot her favorite stuffed elephant and there will be no consoling her if she does not have him for her vacation. The family is still at the cottage and I was tasked with valiantly saving my vacation. I am dad of the year after all. You still haven't told me exactly what is going on here though. So why don't you catch me up on what I just walked in on." He said as he took a few steps into the living room and sat in the arm chair near the fireplace. I sat and faced him.

"Well if you must know, this is the real me. I am most comfortable in women's clothing and I go by Katie when I am. I do not apologize for my desire to wear women's clothing, but I will apologize for wearing Kim's things. If it's all the same to you though I will go upstairs and change. I completely understand if you would like me to pack my stuff and leave. All I ask is that you not tell Kim about this and you let me quit the shop instead of firing me." I proclaimed as I began to stand up from the couch.

"You can keep that dress if you want, Kim hasn't worn it in years!" He said to me as I faced the doorway to the hall. It gave me quite a pause because he sounded sincerely saddened by his statement. I turned back to face him.

"Don't get me wrong I am sure that my wife could still fit it and look spectacular while doing so, but at this point in our lives, with three kids; there is never any time for her to get that dressed up. Hell there is no her and I time for any kind of dress up. With the kids I am pretty sure that my wife is terrified that sex with me will only lead to more mouths to feed and munchkins to chase." He said with defeat in his voice. "Not that I blame her, hell between all the activities and the shop there is barely time to sleep as it is. By the looks of the panties you have on, I now know that she didn't bring anything sexy for our vacation either."

Even though he had spilled his heart out to me about his marital discord I knew that he and Kim were still very much in love. I could see it in the way they touched and the way they talked to each other. They were just in a later chapter of the story of them, the chapters without mind bending sex.

"Well if I'm gonna keep it you have to at least tell me it looks good on me!" I said in an attempt to lighten the current heavy mood in the room. He looked up at me as I struck a sexy pose and did a slow turn in front of him.

"You know what it does look good on you, the garter and stockings are a nice touch too!" He said with a grin on his face. Again he began to sport some wood. I decided I was going to make a Hail Mary attempt at cheering him up. I strode seductively towards him and placed my hand directly on his ever growing erection and leaned into within inches of his ear.

"What kind of things would a big strong man like you want a little sissy like me to do for him?" I whispered into his ear. I felt as his cock pressed back against my hand as more blood flooded into it. "Keep in mind there is no fear of getting me knocked up big daddy."

He rose from his chair and took me by the hand into the kitchen. Once in the kitchen he leaned my over the sink and ran his hand up the back of my leg until he reached my panty clad ass. He ran his hands over every inch of my ass as I bent over the sink. He raised the dress to my waist and proceeded to free his cock from his shorts. He slid his cock up and down the crease of my pantied ass. He began to moan and within a few moments he withdrew and blew a load on the tile floor. I was slightly disappointed that he had gotten his nut that quickly, but I can't say I didn't expect it. I turned to face him with as much compassion as I could muster for our current situation.

"Well sissy slut that shits not going to clean itself up now is it?" He said with an authoritative tone. Get a towel, get down there and clean that floor." With that command I did as I was told. I knelt on the floor and arched my back while I began to clean the floor as I was told. Mike walked from the kitchen into the garage while I cleaned the floor. He returned with a shoe box seconds later and from it he produced a 7 inch dildo. I must have looked puzzled when he pulled the dildo out of a shoe box from the garage.

"Kim doesn't think I know that she keeps this out there." With that he walked over to the refrigerator and suction cupped it to the fridge. "Now if you are done cleaning my floors bitch, why don't you go saddle up to that bad boy?!" I did as I was told. Mike walked over and slid the panties to the side. He then dripped some dish soap on my ass hole and lined me up with the dildo. He eased me back against it until the tip slid inside of me. The ease at which I accepted the rubber cock prompted him to exclaim "my you are a little slut aren't you?!?!"

"I am working on it big daddy." I said as I looked up at him. I was met with his resurrected cock. He quickly slid his swollen rod into my mouth and with the thrust of his hips pushed his cock down my throat and pushed me back down the dildo. As he pulled back from my eager mouth he also pulled the back I my head towards him sliding me off of the dildo. Just before the tip slid from my rear he thrust into me again slamming me back onto the dildo. I caught onto what he had planned for me and was quick to synchronize with his movements. He was thoroughly enjoying our little DP and began to moan loudly. With one large thrust the latex balls on the dildo slapped mine and his balls rested on my chin when I felt them spasm. Mike exploded down my throat. Stream after stream of salty deliciousness. I tried my best to breath through my nose as Mikes eight inches remained firmly thrust into my mouth. After a few weak spasms the pulled his cock from my mouth. I remained with my rubber friend buried balls deep against the refrigerator.

"Looks like you won't have to clean up after that one, your dirty little mouth took care of that." He said as he stepped back and looked at me. "Now stay right there for a few minutes while you think of the dirty little slut things you have done!" Mike walked from the kitchen and I heard him sit down on the couch. I remained where I was told to be and wondered what kind of shit Mike used to do with Kim or did she never do any of this and he was finally getting it out of his system. Either way I was having an amazing time being his sissy little wife substitute.

"Katie get your ass in here you have some explaining to do." As I slid from the dildo I was saddened as usual from the sudden empty feeling. I walked into the living room to find Mike, legs spread apart, fully erect again. "well how do you explain why I am sitting here with a throbbing erection and no one doing anything about it? Get your ass over here and sit on this cock." I obliged and walked over to him. I turned around and began to back up to where he was sitting. He slid the panties aside like before and placed the tip at my already spread asshole, put his hands on my hips and pulled me backwards onto him. I had, had fun with the dildo but it is no substitute for the warm pulsating feel of a real cock. I let out a moan of joy as I slid onto his cock. Mike used his muscular arms to spin me 180 on his cock until I faced him.

I proceeded to ride him cowgirl for several minutes enjoying his fuck faces. Mike slid the front of the panties over freeing my cock from its confines. My cock bounced up and down. As he began to build to climax I lifted off of his cock and placed our cocks together. Using my precum to lubricate between us I used both hands to hold us together and rub us to a mutual orgasm. We both erupted at the same time all over Mikes stomach. As we both went limp I stood up from our spot on the couch.

"Look at the mess you've made this time slut. Get yourself upstairs to the shower you have some cleaning to do." We both walked up to the shower and Mike slid the dress from me. As I reached to remove the panties and bra "nope not yet into the shower with all of it" Mike said as he guided me in. The water of the shower was warm and soothing and I did as I was told as I soaped Mike down. The wet fabric of the bra and panties sticking to me had excited me to no end. As I began to soap Mikes cock and balls he pushed me to my knees. Without warning Mike began to release a warm golden stream onto my face. All the times I had done that for others and here I was receiving my very own golden shower. When he had finished Mike rinsed himself off and I thanked him for everything.

"Hey get cleaned up and make sure my house looks immaculate when we return next week." He said as he stepped out and grabbed a towel.

"So I get to stay? Do I still work for you?" I called after him as he walked into the bedroom.

"Well this house isn't going to sit itself and why would I want to lose such a precious little slut." He joked as he put new clothes on.

By the time I had showered and put on some fun little sleep panties Mike had left for his trip back to Hatteras. On the counter in the kitchen was the little red dress with a note: "she won't even know it's gone and I think you may look better in it anyways. Thanks for the good time you silly little sissy! Love, Big Daddy" I worked for Mike and Kim for all four years that I was in college. Mike slowly smuggled me a better portion of Kim's panties, always with the stipulation that I let him "visit" them. For a brief time Mike and I would close the shop together on Sunday nights and I would give him private little shows. When Kim got pregnant with their fourth child I became Mikes surrogate fuck toy. To this day whenever I go back to Charlotte Mike and I find at least a couple hours together. He will forever be my Big Daddy!!