Kitty's Conversion to Kit Kat Ch. 05

My name is Katelyn but I usually go by Kitty. I'm in my late 30s now but when I was 18 and in my first year of college, I earned myself another nick name, Kit Kat. This is the 5th chapter of my memoirs from that time. Luckily, I recorded the details of the events in a diary which I use to keep when I was younger. I had to add some prose and dialogue of course to make the stories more readable.

I wanted to start this chapter by giving more background information on myself. I 'm white of course with dark brown hair which I keep at shoulder length. I am 5'6" and I use to weigh about 130 lbs. Growing up in a small Canadian city, I didn't have much contact with black people. I didn't lead a sheltered life but in terms of fashion and culture, we were a bit behind. I certainly wasn't behind in terms of sexual experience though. My first boyfriend introduced me to oral sex because I didn't want to lose my virginity at the time since I was only 15. Needless to say I loved having my pussy eaten. In fact that was the only way I had orgasms other than masturbation. At first, I learned to give oral sex to reciprocate but I quickly grew to love sucking cock too. The boys would beg and plead for it and would squirm in ecstasy while I sucked their cocks. Having that kind of power over them was intoxicating. My first boyfriend would always warn me when he was going to cum and he taught me to keep stroking his cock right through his orgasm. Seeing his cum spurt out of his penis and feeling the warm fluid run down my hand gave me such a thrill. I eventually gave up my virginity to my first boyfriend to celebrate my sweet sixteenth birthday. It was disappointing to say the least. I was nervous and he didn't last very long. In total, I had three boyfriends during high school of different durations. The sex did get better and the fucking was fun, but I found I enjoyed the oral sex the most. It was also much easier to cover up if we were interrupted by my parents. I grew to love sucking cock so much that I let my last boyfriend convince me to start letting him cum in my mouth before spitting it out. In addition to my three boyfriends, there were almost a dozen other boys who I hooked up with at parties for oral sex when I wasn't going steady.

My best features were my tits and my long legs. I admit I am no beauty but I made up for it by dressing in tight clothes and short skirts. Wearing hosiery was preferred over bare legs when I was growing up during the 80's. The high school I attended also had a dress code which required girls to wear pantyhose or tights with the school uniform. I grew up wearing pantyhose almost every school day. There are many women who hate pantyhose, but for me, wearing pantyhose or tights feels normal. It is also very practical during the cold Canadian fall and winters. I also developed an intense pet peeve about panty lines as a result of some vicious teasing during high school. Thongs were not around back then and going without underwear, or 'commando', did not seem like an appropriate option. Wearing pantyhose with a built in cotton gusset seemed like the perfect solution for me. I grew so accustomed to wearing pantyhose, I usually wear them with jeans and pants too. About the only time I wear panties is on very hot summer days.

I broke up with my third and last boyfriend after graduation because I was moving to Toronto to attend college. We both knew our relationship wasn't that serious to keep up a long distance romance. So when I started my freshman year, I had clean slate to work with. I hooked up with a few boys for oral sex during frosh week parties but didn't fuck anyone until Mark in chapter one. That was the beginning of a new me but I didn't realize it at the time.

Sunday morning, I awoke feeling a little sore but thoroughly satisfied. I showered, dressed and went for a late breakfast. It was laundry day and I decided to get it out of the way early. As I separated my delicates, I discovered how big a tear Mark made in my new pantyhose from last night. They were quite expensive and I was hoping I could somehow salvage them but they were ruined after only one wear. I loaded up the machine with the regular load before hand washing my hose and lingerie. Back in my room, I was laying out my delicates to air dry when the phone rang.

"Hello?" I answered.

"Hi Kitty, I wanted to apologize for last night." Even though he didn't say who it was, I recognized Brian's voice.

I replied angrily, "You mean for standing me up."

"I kept calling you all afternoon but nobody answered." Brian tried to explain. I remembered that I went out shopping during that time.

"You should have kept trying. I was shopping for an outfit to impress you." I continued tersely. I wanted him to know what he missed.

"I tried again when I got home around ten but you must have gone by then." Brian then continued, "I hope you and Maggie still had a good time."

"Maggie couldn't make it either but at least she left a note." I continued my bitter tone, "I only went to the party to see you."

"I'm really sorry Kitty, I would have gone if I could." Brian sounded genuinely sincere.

"Well, what else was so important then?" I asked.

"Didn't Mark tell you?" Brian asked in return.

"Tell me what?"

Brian replied "I broke my leg in the game. I was stuck in the hospital for hours."

A huge wave of guilt crashed over my superiority bringing me down several pegs. I was too flustered to respond.

After a long pause, Brian spoke "Kitty? Are you still there?"

It was now my turn to be humble "I'm sorry Brian, are you okay? I mean how's your leg?"

"The doctor put a cast on. He said I'll need it for about six weeks."

"Does it hurt?" I asked before realizing what a stupid question it was.

"Yeah, especially when I try to move around."

I felt so guilty, I wanted to make up for treating Brian so harshly. "Why don't I drop by and bring you some lunch then?"

"No, it's okay, I can make it to the cafeteria on my crutches." Brian protested.

"It's no bother, I'll be there around one." I persisted.

Brian relented, "Well, okay. It'll be nice to see you again."

Realizing that I had to start to get ready, I finished our conversation "See ya soon, bye."

I already showered but I had to do up my face and hair. After finishing my makeup, I removed my t-shirt and sweatpants. I slipped on a black bra and pantyhose. Over that I wore a tight purple sweater and black stretch pants. I pulled on a pair of ankle boots and grabbed my purse before heading out.

Picking up a pair of Subway sandwiches, I made my way over to Brian's dorm. Even though I've never been there, it was easy enough to find. Brian's roommate answered the door and let me in. We briefly introduced ourselves before he excused himself, picking up a big duffle bag on his way out. Brian was sitting in his bed with his casted leg elevated on some pillows.

"Hi Brian, I hope he's not leaving because of me."

"Nah, he goes home every Sunday for dinner," and then Brian added "I think his mother still does his laundry."

Brian was dressed in a white t-shirt and baggy black shorts. The t-shirt wasn't especially tight but because of Brian's massive muscles, the shoulders and arms were still stretched taut. Despite his dark brown skin, I could still see some of the bruising on the exposed skin between his cast and his shorts.

I slipped off my boots and dropped my purse on the floor next to them. The room was a bit messy but not too bad compared to some of the dorm rooms I've seen. Sitting on the chair next to Brian's bed, I handed him his drink and sandwich. We talked about the game and his injury while we started eating. The conversation continued on to school as we finished our food. Over the next hour, we talked about a variety of different topics eventually leading to music. Brian suggested I pick out some music to play.

Moving to the other side of the small room, I bent over to look at Brian's music collection. Not recognizing many of the artists, I had trouble picking something to play. Since my back was to Brian, I turned my head to ask him a question. Before saying anything though, I noticed that Brian was staring at my ass. Feeling impish, I resumed looking through the cassettes without asking my question. I took my time making sure he got a good show.

While I was choosing some music, Brian slid over on the bed. After I turned around, he asked "Why don't you sit here next to me?"

I sat sideways on the bed facing him with one leg tucked under myself. Brian leaned forward reaching with one hand to cradle my face. With the slightest of tugs, I felt myself drawn to him. I closed my eyes as I leaned forward, our lips meeting in a soft kiss. Brian's hand moved from my face caressing my skin down my neck to end up resting on my shoulder. We kissed for a few minutes before Brian's hand started moving again, sliding down to cup a breast. He started squeezing my breast gently using his thumb to rub my hardening nipple through my bra and sweater. Stating to get excited, I slipped my tongue into Brian's mouth to twirl around his. Brian responded by massaging my breast firmly and intensifying the pressure of our kiss.

With my passion building, I noticed that my pussy was starting to get wet. Wanting to know if Brian was equally excited, I reached between his legs. Feeling his hard cock straining against his shorts further fuelled my flame. I started rubbing his cock through his clothes as we continued our deep kiss. Brian obviously liked that as he thrust his tongue deeply into my mouth. I began sucking on his tongue as if it were his cock. After a prolonged spell, Brian finally broke our kiss.

"Damn, I wish my leg wasn't broken. I want to fuck you so bad." Brian said in a throaty voice.

Hearing him say those words made me recognize how much I wanted to fuck him too.

Pulling my sweater off over my head I replied "I want you too. I'll have to stay on top."

Brian didn't need any more encouragement as he whipped off his t-shirt as I undid my bra.

"Beautiful." was all Brian said when I slid my bra off and threw it onto the chair next to the bed.

Brian leaned down and took a nipple into his mouth as his strong arms pulled me a little closer to him. My eyes closed as I rolled my head as I enjoyed the incredible sensations. I felt his tongue flickering around my nipple as his thick lips sucked on my tit. As Brian moved from one breast to the other and back again, my fingers traced the outline of his gorgeous muscles on his back gliding on the smooth dark brown skin.

Releasing his grip on me, Brian moved back up to give me a short kiss before whispering "I have some condoms in my desk drawer."

Getting up off the bed, I quickly walked over to the desk to find a condom. On the way back I saw Brian pulling down his shorts and briefs. His beautiful black cock sprung free and was fully erect. He managed to slip his clothes off his good leg easily enough but struggled with the broken leg because of the cast on it. I took hold of his shorts and briefs and carefully worked them over his cast and off his leg. Discarding them onto the floor, I then helped Brian reposition himself on the bed and removed the pillows from under his broken leg so that he was lying completely flat.

As I moved back towards the head of the bed, I trailed my hand up along the inside of Brian's good leg. Reaching his groin, I gently caressed his cock and balls as I admired how erotic the dark brown skin contrasted with my ivory white fingers. Next I grasped his cock by the shaft and began a slow stroking motion. Some clear liquid seeped out of his urethra which must have been his precum. I bent over the bed and drooled some saliva onto his cock to help lubricate it as my hand continued slowly stroking the shaft. Using both hands now, I worked the saliva and precum mixture all over his cock and balls. I had already decided that I wanted to suck Brian's cock a little before we fucked so I was getting it ready. Wanting to see if I could take all of his cock into my mouth, I knew that I had to get it very wet and slippery. Now Brian has a big cock but mostly in terms of thickness. He wasn't much longer than an average sized penis but it was very thick.

I bent further down and started sliding my tongue up and down the entire length of the beautiful black cock in my hands. Turning my head a bit, I looked up to see Brian's reaction. He was propped up on his elbows and looking at me with a look of pure lust. Slipping the head of his cock into my mouth, I used my tongue to swirl around the head while I created some gentle suction. Slowly I took more of his cock into my mouth as I increased the intensity of the suction.

Brian reached over and started rubbing my ass through my clothes. Feeling him pulling at my ass, I repositioned my body so that I was kneeling at the edge of the bed by his chest. I managed to do the entire manoeuvre without letting his cock slip out of my mouth. Brian's hands moved from my ass and started rubbing directly over my pussy. The thin material of my stretch pants and pantyhose didn't give me any insulation from Brian's hand. I'm sure he could feel every fold of my vagina and how wet I was. My pussy's response from his hand caused ripples throughout my body.

I started forcing Brian's cock deeply into my mouth, trying to take his entire length. With my concentration focused on controlling my breathing and suppressing my gag reflex, I didn't notice that Brian must have pulled down my pants and pantyhose until I felt him inserting a finger into my pussy. I pushed my ass back onto his finger inviting him to do more. He slipped a second finger into my pussy and started to finger fuck me. That made it nearly impossible for me to fully concentrate on deep throating his thick black cock. I changed my goal and decided to just enjoy sucking Brian's cock as he continued to finger my pussy. Bobbing my head faster and faster, I couldn't keep the suction going which made my saliva to run down along the shaft and onto Brian's balls.

I felt Brian withdraw his fingers from my pussy as he said "You're gonna make me cum soon if you keep that up."

Part of me wanted to keep sucking Brian's cock and get the thrill of seeing and feeling him cum. The other part still wanted to feel his big black cock inside my pussy. Since Brian and I haven't fucked yet, my pussy won the debate and I released his cock from my mouth. Standing up, I quickly slid my pants and pantyhose down the remaining part of my legs before kicking them off my feet. Then I picked up the condom I got earlier from the chair and sat back down on the edge of the bed. Undoing the wrapper, I pulled the condom out from the packaging. Brian held his cock upright for me as I slid the condom onto his cock. It was a bit tricky since his cock was still glistening from my saliva and quit slippery.

Getting up onto the bed, I moved to straddle Brian's torso while on my knees. Looking down I reached for his cock with one hand as my other hand steadied myself on his chest. Directing his cock towards my pussy, I slowly lowered myself onto his cock. I watched intently as the lighter brown skin of the circumcised head spread apart my pink pussy lips before disappearing inside of me. As more of his cock entered my pussy, I felt myself being stretched by the thickness of his cock. I closed my eyes to concentrate on the delicious sensations of feeling so full. I continued lowering myself until our groins met and his cock was completely inside me. With my eyes still closed, I paused for a minute to let my pussy adjust to his size. I felt Brian grab both of my breasts and start squeezing them firmly.

Having just fucked Mark last night, it didn't take me long to adapt to Brian's size. I started moving myself up and down on his cock, rolling my hips slowly. Even though I know Brian's cock isn't as big as Mark's, it sure felt just as big. The same wonderful intense pressure was sending waves of pleasure throughout my body with each stroke.

Brian started squeezing my tits roughly as I picked up speed and rocked my hips quickly. My excitement was building quickly and I reached down with one hand to play with my clit to speed it along. That was all it took for my orgasm to burst over me shattering my senses. By now I was bouncing on Brian's cock causing the bed to squeak. Suddenly, Brian wrapped his arms around me and pulled me into him in a tight bear hug, his cock still deep inside my pussy. Since my body was still quivering with aftershocks, I didn't struggle and just lay on top of Brian enjoying the afterglow of my orgasm.

Opening my eyes, I saw that Brian was grimacing. "What's wrong?" I asked.

"The movement was hurting my leg." he answered releasing his bear hug.

I then realized that my bouncing must have been too vigorous for the new fracture. "Oh Brian, I'm sorry. I got carried away."

"That's okay, but I think that we should stop." Brian said sounding disappointed.

"Let me make up for it." I said as I slid off his still hard cock. Not waiting for an answer, I quickly turned around and grabbed his cock. Ripping off the condom, I took his cock back into my mouth.

Wanting to make sure Brian enjoyed himself, I spent the next 30 minutes making love to his black cock with my mouth. Slowly at first with a lot of tongue work. Several minutes attempting to deep throat his cock followed. I came ever so close but the thickness of his cock made it impossible. Picking up speed next as my head bobbed on his cock while my hand fondled his balls. Brian would start to gyrate his hips when he got close to cumming which only made me slow down again. After a couple of minutes of sucking his cock slowly, I would pick up the pace again. Then when I sensed that he was close, I backed off. I managed to bring him to the brink without cumming 4 times. My mouth was starting to get very tired and my jaw was starting to ache so on the fifth time, I didn't let up.

Brian managed to rasp out a warning, "Kitty, I'm cumming!"

This time I was fully aware that Brian's cock was about to erupt. I had already decided that I wanted to feel his cock throbbing in my mouth, his cum spurting against my tongue. The only surprise was the volume of his cum. I must have felt at least half a dozen large spurts shoot into my mouth. I had to swallow several times to keep it from leaking out. I continued sucking his cock right through his orgasm until I felt his cock completely stop throbbing.

Brian pulled me up to lie next to him. We kissed and cuddled for awhile before cleaning up. I separated my pantyhose from my pants before straightening them out and slipping them back on. After pulling on my stretch pants, I put on my bra and sweater. We spent the rest of the afternoon watching a football game on TV together.