Lesley and Kerry Ch. 01

It never entered my mind when I met Kerry that both our names were homophones for the masculine and feminine gender. My name is Lesley. I was named after my maternal grandfather, Leslie Jackson. Kerry and I were in college. My roommate was dating his best friend. We had met on occasion but were not dating or even out with the same groups of people. He was nice and intelligent. I was more into the college scene. I gravitated to the activities, whether school related events or outside occasions. I had a large group of girlfriends and did not have a steady boyfriend. Not to say that I didn't date. I did. A lot. I just couldn't see limiting myself to one guy. Most of my girlfriends did however have mostly monogamous relationship with their boyfriends. I say mostly because you never know what happens when the cat is away, so to speak. I didn't like the pretense. I had sex with a number of guys. When a guy got too serious, we had the talk. It was to remain casual friends or maybe friends with benefits. If the guy wanted more, I told him to find another girl to give him more. I was not going to be limited to a monogamous relationship. It came with a downside, of course. I might miss out on a little but if I needed a date for a function, I could make a few calls and be set up quite expeditiously.

After meeting Kerry a few times on happenstance with my roommate and her boyfriend, I began to recognize him on campus. Eventually we greeted each other by name. I had no idea at the time that we would become a couple. Two years later, still on the smile and greet, I had the occasion to run into him at a coffee shop off campus. We did the usual, hi and goodbye. For some reason, I lingered outside the shop until he came back out. We struck up our first conversation. I realized then how intelligent and genuinely nice he seemed. We talked about our majors, our plans, the weather and such. I asked him if he was seeing anyone in particular. He wasn't. He asked the same about me. I told him the truth about not wanting to limit myself to just one guy. I wanted to meet all kinds of people and enjoy the college experience.

He asked if I would like to have dinner with him one evening. I wasn't particularly attracted to him but I usually didn't shoot a guy down when he approached me, so I accepted. It turned out to be a very casual date. We ate burgers and fries at a local hangout. I had a good time. It was nice to be with a guy and not feeling like you had to have sex with him. We talked about our hometowns and growing up. He seemed interested in me as a person rather than a piece of meat. When he took me back to my apartment, I gave him a hug and a quick peck on the cheek. I also, for some reason, told him that I would love to go out with him again. He seemed surprised but we exchanged numbers and said goodbye.

Having surprised myself already by indicating an interest, I called him two weeks later. I was surprised that he did not call me. I wasn't insulted exactly but I usually didn't call a guy. He said that he had been busy with homework and his part-time job. He seemed happy that I had reached out to him. He didn't make any further invitations as I was hoping. I finally humbled myself and asked him if he would be my date to one of our sorority dinners. It was not terribly formal and some girls didn't even bring dates. He agreed to go with me. This was our second date. It went well and we went for coffee together afterwards. When he dropped me back off at my apartment, he didn't make any move to kiss me, so again, I had to kiss him on the cheek while I hugged him. He did at least hug me back.

Kerry is a nice-looking guy. A little short at 5'-7". I am 5'-8". This would usually preclude me dating him. I had never gone out with anyone shorter than me. Maybe that is why he seemed a little reluctant to initiate any physical contact. It could not be that I am unattractive. I am not fat or even heavy set. I weigh a comfortable 125# and have the curves in the right places. I am proud of my 34 D breasts. Hell, I look great in bikini. With light brown hair and a nice complexion, I didn't have to pursue any guys. I guess in a way this added to the intrigue of why Kerry was not more interested in me physically. It took several more dates for him to warm up. We eventually made out some and I still wondered why he never made sexual advances toward me. I was putting a lot more time into the relationship than I ever would have thought. One night while making out, I lay back on my bed and held out my arms to him. I was wearing shorts and a tee shirt because I had been studying before he came over. I didn't have a bra on and my nipples were very hard. Also, I have very pink areolas. They are over two inches in diameter. I had been told by a number of guys that my boobs were perfect. I was glad they liked them. I am also very sensual about my boobs being fondled, especially my nipples.

I took Kerry's hand and move it under my shirt letting him feel my large warm breasts. He explored my curves for a while. I removed my shorts and panties along with my shirt. I helped him unbutton his shirt and unzip his jeans. He was wearing white boxer shorts. He wriggled out of the shorts and his cock sprang forward. It was the most beautiful cock I had ever seen. It was not large. It was not particularly thick. He was not quite even six inches long. It was just beautiful. That is the only way I could describe it. He was not circumcised but the pink head was sticking out about halfway past his foreskin. Maybe the most amazing thing about his cock was the color contrast between the pink head and the almost alabaster hue of his shaft. The next most noticeable was his scrotum. It was very small. It was drawn tight. His balls were slightly on the smaller side and his sack held them tightly. He was a very light pink color. Altogether, the pink head, pink ball sack and the near white shaft were a color combination that I had never seen. Most guys had hairy balls and pubic hair. Kerry's was blonde matching his head. Just a little lighter even. It was scarce as some fair skinned people are. I could not take my eyes away. I sat on the bed and held him between my legs. This cock was made for sucking. I licked the head and slowly took him into my mouth. I was savoring the experience like a classic delicacy.

As I continued to take him deeper, I could sense his flow of precum and the further tightness of his ball sack. I took him to my gag reflex. That was as far as he reached. I could easily take a longer cock into my throat and some of my well-endowed boyfriends could shoot cum directly down my esophagus. Kerry was not that big. My tongue circled that clear indention of his cock head. I wanted to eat it like a popsicle. My lips were planted firmly on his pubic bone and taught scrotum. He didn't last long. He began spewing cum deep into my mouth. I had to pull back a little each time to allow his cum to pool in my cavity so I wouldn't choke on the flow. I sucked until he had no more cum. Holding all his cum in my mouth, I looked up into his eyes and opened my mouth, giving him a clear view of his cum. I swallowed and then wiped some off my chin with my fingers. He started deflating rather quickly. I allowed him to lay on the bed. I guided is hand to my dripping pussy and he inserted his middle finger. My clitoris was very hard. I was ready to cum. As he probed my pussy, I had to direct his finger directly to my love button. I held his hand in the right position and I fucked his finger until my orgasm overtook me. I squeezed his hand with my thighs. I held his finger inside me until I began coming down from my short but satisfying orgasm.

We lay for a while in each other's arms. Afterward when Kerry started to put his clothes back on, I noticed that his cock had drawn up really small. He was decent size when erect. I was curious about why he became so small but passed it off to the fact that once I was fucked well by a big stud, I didn't notice how small his cock deflated afterward. I decided to pay careful attention the next time I had a better endowed lover. I had plenty to choose from. It came to mind that I ended up dating the guys with bigger cocks more than once. Thinking back, I was reluctant to admit that the smaller guys didn't make me cum. I hardly ever went out with a little dicked guy a second time. For some reason, college guys don't seem to want to eat pussy. They certainly expect blow jobs from the girls. That pissed me off when I thought about it. I was determined to have Kerry reciprocate the next time I sucked him off. Hell, there I was, about to break my mold. Already thinking about dating Kerry even though he was not hung. It was just that his cock was so pretty I couldn't stop thinking about it.

The next week, I broke my mold again. I called a friend with benefits, Jeffery. He was a six-foot-tall stud with 8" of thick cock. I loved how he made me cum. It was unusual for me to call a guy, so he was impressed that I wanted to get together. I asked him over the following night. When he arrived, we ate a light snack and then adjourned to the bedroom where he fucked my brains out. I didn't suck him beforehand. We just got to the fucking. He made me cum twice before he blasted me with a huge load of semen. I made sure that we cuddled for a long time afterward. I talked to him about just stuff. He seemed to appreciate it and maybe even thought we were headed to a relationship. He had no idea that all I wanted was to see his cock in the flaccid state to compare it to Kerry.

I made it a point to get up to signal it was time for him to leave. His cock was deflated but still appeared quite long. The swollen thickness was down a little but his scrotum was soft and quite relaxed. His huge balls were prominent when he got up to put his clothes back on. This was totally different from Kerry's shrinking equipment. It made me appreciate Kerry's dick even more that it could do its business and shrink back easily. I started having some thoughts about where this would lead us. Again, it was so incongruous of me to be thinking about a relationship with a guy not super hung. The more I tried to talk myself out of pursuing Kerry, the more intrigued I became. He was truly a nice guy. He had that going for him. Could I get used to the smaller cock, no matter how gorgeous it was?

Some of the guys I had slept with had very big cocks. They were not what I would call pretty. In fact, some of the better ones looked all hairy and well,... angry. There was nothing angry about how they satisfied my pussy but it was the feel of them inside me, not the look, that kept me interested. While I didn't get attached to any one guy, I seemed to have a sixth sense in picking out guys who were well-endowed. I was disappointed a few times and I ended up fucking those guys anyway. Kerry was different. He did not come on to me or any other girls that I knew of. I would have never picked him out of a group anticipating that he had a big cock. He seemed like someone so naïve yet genuine. When I saw his cock, I was transformed into a girl who not only wanted sex but wanted a close relationship. Up until that point I had never considered a cock pretty. They were big, small, average, thick or whatever but never 'pretty'.

When he finally got the picture that I was interested in him, he was more forthcoming. The first time we had actual sex, I sucked his cock before we fucked. I was on a path and I wanted to keep him interested. I barely had an orgasm. It was still very sweet. I had to work on his libido and get him started on oral sex for me. Gradually, he got the picture that I wanted oral sex before we fucked. I guided him to the most satisfying type of oral sex for me. I liked for my lover to lick me up and down my wet slit to get me good and ready for intercourse. For my orgasms, it had to be a sincere devotion to my clitoris. I have a rather large clit when I am aroused. Most guys couldn't miss it when they went down on me. A few, I had to spend more time in the instructional phase. Generally, if a guy didn't pick up on my vocal appreciation of his tongue on my clit, he wouldn't turn out to be a good lover anyway. On a few occasions, I had told the guy directly to suck my clit like I sucked his cock. The guys who would not eat me out were goners in my book. Of course, the guys with really big cocks got a pass up to a point. Some of the Neanderthals who thought eating pussy was beneath them were never to get in my pussy. Ever again.

With some careful grooming, Kerry learned the act very well. I liked taking a neophyte from start to finish. I could train him in the exact way I wanted my pussy licked and sucked. Kerry was always asking me afterwards if I enjoyed it. I would critique him honestly. If I found some fault with his technique, I just told him. The next time it would be much better. Then I began to talk more directly and vulgar to him while he ate my pussy.

"Suck my clit like you would a cock, Kerry."

"Stick your tongue up to my womb, Kerry".

"Fuck me with your mouth, Kerry".

After one or two fantastic orgasms, I would let him fuck my sloppy pussy. He even admitted that he loved how slippery I was after we had oral sex first. As he became more adept at bringing me off with his mouth and tongue, I decreased the regularity of his blow jobs. He was going to fuck me and cum in my pussy anyway, so I decided to give him blow jobs only when he really gave me intense orgasms. He was very unselfish in that way. I gradually began thinking of him as more submissive. His personality was not necessarily that way, just sexually, he was more submissive. I decided I had uncovered a diamond in the rough. Sometimes, though, I just loved sucking his pretty cock for myself. It was large enough that I would sometimes have small orgasms but it really didn't matter to me as long as he maintained his fervent desire to bring me off orally.

After a few months, our full relationship was growing and I had to answer some questions to erstwhile boyfriends why I was hanging with Kerry so much. I told them the truth: that he was a really nice guy and treated me special. That didn't set well with some of the guys that I had fucked more than once. I had to let them know that I was not some kind of property that they claimed by sticking their cocks deep inside my pussy. I didn't put them on the road, so to speak, but some thought they needed to be more in charge of a sexual relationship. I carefully explained to them that sexually speaking it was both parties who got pleasure out of the act. They were to be more considerate of my needs during sex especially oral sex. I could not be exclusive with Kerry. I needed a big thick cock up my cunt every so often. I didn't discuss this with him even as our relationship grew stronger. He didn't ask, either.

I started thinking of a way to strengthen my relationship with Kerry while still having more well-endowed lovers on the side. I decided that eventually I would have to find a way to reconcile the two. I was prepared to sever the relationship with Kerry if I had to. Surely there was a way to develop his submissive tendencies until he accepted the other half of my sex life. I read articles and concluded that I needed a cuckold relationship with Kerry. He was such a nice guy that I had no intention of humiliating him. I would rather him find someone else than to hurt him. If he had any natural inclinations, I made a plan to discover them. Otherwise, I would have to just tell him that I had some needs that he could not possibly meet. In a way I wanted to forget my need for more aggressive sex but I knew that I could not keep that promise to either Kerry or myself.

As Kerry and I began seeing more and more of each other, I watched for signs of jealousy. Occasionally he would call me and I would have to make up a plausible excuse to not see him. I didn't know for sure that my explanations were making sense but he seemed not to be put off when I did this. I just couldn't give up those big cocks. It didn't matter how old or young the guy was. Black, brown or white, I didn't care. All that mattered was that they were reasonably well endowed. I began not caring whether the guy was good at oral sex. I was getting the best oral sex from Kerry. There was no reason for him not to be good at eating pussy. After all, I had trained him. In addition, my other lovers were no longer getting blow jobs from me. The only deviations in my side sex was maybe some favorite positions. Many guys only knew missionary. I liked doggy with the guys who were not huge. The huge ones could fuck me any way they wanted.

One early evening, I had been with one of my well-endowed lovers. After sex, I made an excuse to go back to my apartment to study. Kerry called almost exactly when I got home. He wanted to drop by with a pizza. I had just been royally fucked but I wanted to see him. I was going to take a quick shower before he got there. I cleaned up my room and straightened the living room first. I didn't realize that he already had the pizza. He rang the doorbell before I had a chance to shower. I told him that I needed a shower but he said the pizza would be cold by the time I got out. I decided to chance it. He kissed me deeply and I returned the kiss likewise. We ate pizza and had a beer. After the pizza, he became more amorous. I had to lie to him and tell him I was on my period but would suck his dick. I didn't mind sucking his dick as I was always loved how gorgeous he was. He came in my mouth. I held it all in and showed his cum to him. Then I swallowed. I told him that I needed to get started on a paper. He was ready to leave when I kissed him firmly on the mouth. I don't think he forgot that he had just cum in my mouth. He didn't hesitate to kiss me back, so I slipped my tongue into his mouth. He didn't appear to be repulsed. I gave him another quick peck at the door and told him that I would be all his the next week.

After he left, I thought that I might have discovered a side of him that was at least a little submissive. There was no doubt that he tasted his cum. It might have had a little pizza overtaste but it was still slippery like cum. There was no mistaking that. I thought of a few ways to exploit this tendency.

Now that Kerry had tasted cum, it would be no mistaking if I had another guy's cum on my breath. I decided to take a chance. I mentioned to him that I was still working on my paper but I would like him to come by later in the evening. Maybe bring a pizza like he had done before. When he got there, I kissed him deeply. I hadn't been working on a paper at all. I had been fucked by a tall, black basketball player. It was one of my favorite big cocks. Not nearly as pretty as Kerry, but big. Like 10" big. And thick. He filled my cunt like no one else had. I had fucked him plenty of times. He got all the white pussy he wanted, being a star athlete. However, I didn't have to do much more than meet him on campus for him to invite himself over to fuck me. That evening, after I had orgasmed twice, I had him pull out and shoot off in my mouth. It was much more than a mouthful. He had enough cum to impregnate half the student body. I loved it when he deposited his cum in my pussy but that night, I just wanted his cum in my mouth. I even swirled it all around before I swallowed it. I wanted Kerry to taste it before we got down to eating pizza.

So, when I kissed Kerry, I stuck my tongue into his mouth as far as I could. I encouraged him to explore my mouth with his tongue also. I wondered if he would say anything. I was held in suspense as we continued to kiss. I licked his lips as we slacked off to just pecks and hugs. He didn't comment. I kept waiting for him to say something. He didn't. I got some beer and we ate pizza until we were full. Then I took off my clothes and had him do the same. I lay on my bed and spread my legs. My pussy was still juicy from the big black stud just having fucked me but he hadn't cum inside. Kerry licked me tenderly up and down my slit. I was ever so hot feeling his gentle approach to my pussy. He kissed my vaginal lips and licked more but just as gently. He would pause and kiss my pussy like he did my mouth. Not too firm but very affectionately. It was nice that the took his time. I enjoyed this with him. The big cocked studs could fuck me as quickly as they wanted. I didn't care. But with Kerry, I savored his patience and the build up to the ultimate climax when he turned his attention to my clit.