Part One: The Cheryl Chronicles
Getting my haircut was always viewed as more of a waste of time than anything else, and this time was no exception; despite the vast time it took, a new haircut still made me look and feel like a dork.
So, to say the least, I was generally not bristling with confidence.
I left the place after tipping the girl two dollars for my emasculation: It was highway robbery.
I decided that since all of my hip friends were all already gone doing whatever it was that they were doing, that I would use this time wisely and spend some quality time with my very best friend in the whole wide world: me. I would rejoice in my singularity by going to the video store and renting a movie, naturally something violent, with lots of action, and oh yes,with a lot of splattering fake movie blood in it.
The video store was right next door, so I could just easily walk my freshly bowl-cut head over to it.
The very first thing I noticed when I opened the door to the video store was Cheryl, a girl I had gone to school with, who was working behind the counter wearing a ridiculous company uniform. I had not seen her since High School; and at the precise time I noticed her, she recognized me as well. We immediately smiled at each other and I walked over to the counter to talk to her.
Cheryl had the sweetest smile, and hidden under her uniform,as stupid and unflattering as it was, was a pair of breasts heaving to get out from underneath; they stretched at the buttons as to offer little windows at her tightly stretched lacy white bra, and if not for a couple twirls of thread they would have been fully exposed to me.
I stood there, trying not to be rude, but I could not believe that I was the only one who could see this treasure. I looked around the rest of the video store and everyone was more interested in the current releases than in Cheryl. Good, I thought to myself.
But despite her good looks, her long blonde hair, thick lips, and big breasts, it was her green eyes that sparkled with a knowing warmth that at first intimidated me somewhat. She made me feel a little uneasy how she seldom looked away from me. At first I thought it was my dumb bowl hair cut, believe me I thought everybody was looking at it.
"You know I had the biggest crush on you in school," she laughed.
"Really?" I told her that I never knew, and that I wished I had.
She recommended (and ultimately talked me into) some racy videos that she said were her favorites, and that I use her employee discount to save a couple of bucks on the rental. She even escorted me to the proper sections in which those movies resided.
Back at the cash register I thanked her for her kindness,and told her how good it was to see her again. I clumsily asked her if she wanted to go out with me, and wondered if I could get her phone number. I was surprised when she asked me for mine instead. I happily gave her the number to my phone, and she said she would call me that night.
With heart pounding heavy in my chest and a stirring deep inside me, I left the video store to go home.
I had only been home two hours or less when the phone rang. It was Cheryl. She wanted to know if I would meet her, and one of her girl friends, at the sports bar by the softball fields. I quickly agreed and said I would be right down.
The sports bar was only ten minutes away, but I got there in seven. I walked in to see her waving at me from a table about mid way through the crowded bar. Sitting at the table with her was her friend Pam, of whom I had never seen before. A pitcher of beer was already on the table and an empty glass that had my name all over it. Gone was that intimidating feeling that struck me earlier. Gone also was her ugly uniform, replaced by a nice white silk blouse and tight blue jeans.
But from the moment I sat down, the girls started to annoy me. They kept whispering to each other and laughing. With every little giggle they would shoot a glance at me that made me increasingly paranoid.
It was the haircut after all, I thought to myself. They are just making fun of me.
I could take it no longer. "What's so fucking funny?" I finally said rather sharply.
Suddenly they realized what they had been doing, or more precise, they realized that what they had been doing was annoying the hell out of me.
"Should I tell him?" Cheryl's friend asked.
"Tell him what?" I demanded. Cheryl smiled and encouraged her friend to go ahead.
Pam leaned closer to me, and in a whisper said, "I know something you don't".
I looked at her a little perturbed.
"We were laughing, because you are about to get a blow job in the parking lot."
One eyebrow lifted. "I am?"
"Cheryl," Pam whispered, "wants to suck your dick."
I looked at Cheryl who was giving me a look like she was hungry and I was a Porterhouse steak.
"Is that what you want?" I asked her.
Cheryl smiled the cutest smile I think I had ever seen and nodded her head.
I downed the beer in my glass in one gulp. Both girls laughed out loud. Cheryl stood up and accepted my hand. We left Pam sitting in the booth.
"Ta Ta," Pam waved. "See you in a minute."
I smiled and jokingly gave Pam the finger.
We walked out of the sports bar arm in arm, and went to my car. It was cold outside, but for Cheryl and I things were about to heat up.
Once in the car, we embraced and began kissing. I opened her shirt and finally got my hands on those breasts without any real effort at all. She groaned as I rolled her nipples with my thumb.
I was growing larger against my jeans until my pants felt uncomfortable and confining. I throbbed and groaned to be released from them.
Cheryl's hand dropped down my chest and came to rest in my lap. She felt my leg and the length of my hardness in between. Still lower she dropped her hand and felt the warm softness of my balls through my jeans. I thought I was going to go insane. I wanted to fuck her right then and there, but she was on a mission and the girl would not be denied her prize.
With great alacrity she undid the button on my pants with one hand, all the while her tongue probing mine. Our kisses became more urgent. Slowly she unzipped me. Then suddenly the confinement was over, and I felt the cold rush of fresh air as I came swinging out of my pants fully exposed, with only her warm hand working and stimulating me.
We stopped kissing and looked deep into each other's eyes,her hand still going up and down my entire length. She paused and locked her gaze into my eyes. Then, she looked down. She wanted to see it. She wanted to watch her hand working me.
"Look at this big beautiful dick," she breathlessly declared.
The next couple of minutes were a blur to me. Her head dropped down into my lap, and as she did I could smell the freshness of her long hair. Her lips hugged around me, wet and warm she took me deep into her mouth.
It did not take me long until I began to feel a distant wave building up deep inside. The rush began growing until at last it took control over me.
I told her I was about to cum. She only began to shake me faster and suck me more deeply. I could tell that she wanted it as much as I did.
The powerful rush overwhelmed me, I tightly gripped the back of her hair instinctively forcing myself still even deeper inside her, while the release jettisoned into her mouth in electric spasms. I thought it would never end, and I did not want it to.
Finally I relaxed back in jerking flexes totally spent.
Cheryl looked up at me, with mouth still fixed open, to display the remnants of the silky prize in which she sought. Her tongue greedily searching for more on her lips. She purred a soft sound of satisfaction.
"mmmmm," she purred. "That's good."
She then took the time to lick me entirely clean, so as not to leave any mess whatsoever.
Cheryl went back down one more time. This time with a slower motion as she looked up at me. I watched my dick sliding in her mouth, as her green eyes pierced me to my very soul.
After that, we got ourselves together and headed back into the bar, where her friend still sat with a sly grin.
In the months that followed Cheryl and I saw a lot of each other, but damn my sudden chivalrous attitude! Something got into me where, and for some reason that escapes me now, I consciously decided not to allow that incident outside the sports bar to happen again. I guess in some way I wanted to make something of an honest woman out of her.
So to that end, we took up the art of dry-humping. We would grind ourselves together through our clothes. We did manage to get some measure of pleasure from it. However, it was very frustrating. It was agony. It was all self-induced mind you. I did it to myself. Cheryl would have been completely happy to make love to me, but like I stated above, the idea was wholly mine.
As frustrating as it was though, our dry-humping was accomplishing a purpose: we were building up an enormous amount of sexual tension that would have made us kill for each other.
After two weeks of this one thing was certain: we needed to fuck, and we needed it badly. It had become a most immediate need.
We planned a special night two weeks in advance of the actual event. We were both looking forward to it. By the time the date was upon us, we were loose, both of us begging to be put out of our misery.
The night began in a flurry of kisses and flying garments. We stripped down to nothing in record time. We had had quite enough of those hindering clothes.
It was my goal to have Cheryl in every position, well, at least the big three.
Cheryl hit the bed on her back, pulling me with her right on top. We began making love, we were in time together. All of the dry humping committed our own rhythm to muscle memory.
Cheryl's legs wrapped around the lower part of my back, her hands moving between my shoulder blades. I touched her lips and she put my finger in her mouth, sucking it. I hardly knew that our bodies had been slapping together.
I arched my back and braced myself up with my arms. Together, we both looked down and watched my dick entering her. We moved in tune, perfectly harmonizing in each other's pleasure.
The feeling became too much, and I did not want it to end,so I gingerly exited out of her.
"Get on top," I told her. She obeyed without question, knowing the pleasure that awaited her.
I lay on my back, partly propped up on the head board of the bed. My legs were slightly spread and I was stiffly sticking straight up.
Cheryl could not resist a couple of good strong tugs with her mouth upon my penis. The suction broke with a smacking sound that sent my dick rebounding into my stomach.
Cheryl got to her knees and began to mount me, one hand clutching me with a firm grip. She slowly lowered herself onto me. The resistance entering her was fantastically smooth and warm. Cheryl arched, put her head back, parted her lips, and let out a moan that only comes from depths of satisfaction.
I touched her breasts and covered her nipples with my mouth.
She grabbed the back of my head, and started to move, grinding me with an urgent purpose. I lay back and lifted my hips to meet each pulsating movement. Cheryl reached behind her and cupped my scrotum in her hand, feeling herself rising and lowering on me.
I was about to cum,and had to fight against it. I clenched my teeth, grabbing her shoulders.
"Stop," I said, and Cheryl breathlessly complied with some disappointment. I slowly and gently lifted her up and backed out of her. She was so wet and close to orgasm, and so was I, but I had one more position left and I was determined to make sure that we got there.
"I want to fuck you from behind," I told her. She maneuvered herself around me as I slid out from underneath. Cheryl grabbed a pillow and wrapped her arms around it, ass angled high in the air. I went to my knees behind her and held myself with my own hand and prepared to go back inside her.
Her round ass was perfect. I could see the parting of her lips and the gathering fleshy mound of her clit. I could not help myself. I had to taste her.
My mouth came to rest on her pussy. My tongue licked down to envelop her luscious clit, then back up again. Over and over Cheryl leaned back to grind against my face. I could hear her moaning into the pillow as her body starting to shutter. I knew she was close to orgasm. I flicked at her clit with my tongue several more times, before giving it one long last lick from bottom to top. Then I backed away.
I spread her cheeks open with my hands, and watched the head of my penis disappear into her pussy in one powerful smooth stroke.
Cheryl groaned in delight. "Yeah fuck me," she pleaded.
I started to work it deep inside her. Back and forth I began to get into my final rhythm that would take me to climax. But Cheryl had other ideas.
I fell out of her. It happens, I thought to myself. So I guided myself back in, and started to build momentum once again.
I fell out again. Now this was really starting to piss me off. At first I could not figure out why I kept falling out.
Then I realized that it was because Cheryl kept dropping her ass down. This was odd. Was she getting tired, or lazy, on me?
So I decided that she needed a wake-up call. I grabbed myself with one hand, held her cheeks open with the other, and sought to put some firm pressure on her anus. That ought to solve the problem, I thought, and get that ass up where it belongs.
I touched my penis to her anus and applied some firm but gentle pressure. To my utter amazement, Cheryl pushed backwards at that precise moment and I slid right through. Cheryl let out a long satisfying moan that can only be produced in moments of total pleasure. She had crossed the threshold of where pain, pleasure and all things in the Universe are blended into one.
At first I thought there must be some mistake. I could not be where I thought I was. I could not be doing what I thought I was doing. I was having some kind of out-of-body experience. It felt good, but different. It was warmer, tighter, than before, better than I could have imagined. I had to be sure. I reached down between her legs and began playing with her pussy, now empty. I could freely slide two fingers into her. And suddenly, because of the initial shock, I no longer felt that I was on the brink of orgasm. Instead I felt renewed.
I had never fucked a girl in the ass before. I always considered it too taboo. But now that I was doing it, and saw how Cheryl was enjoying it, I was aghast with wonder. This was not my idea, it was hers. This was what she wanted. I was dumbfounded.
I went with it. I started to move normally. I started to fuck her; I started to fuck her in the ass. With each thrust she backed into me to get more. I began to fuck her faster. I was dimly aware that my balls began to slap her wet pussy. It was driving both of us crazy.
Cheryl grasped the pillow and moaned with her eyes closed, mouth wide open, as I fucked her. She orgasmed, and then orgasmed again, and again. I could not stop fucking her. She could not stop cumming. Faster and harder I pushed, my senses delirious.
I was filling up with cum, rushing, but I hardly took notice. I began to tighten, and I knew that there was no stopping it this time.
I orgasmed hot cum into her anus for several minutes it seemed. I kept pumping, but eventually my penis became loose inside her, as my swelling came down.
I think I fell. I do not remember. I just remember laying there afterward totally exhausted and satisfied, Cheryl in my arms, her head resting on my bare chest. Both of us breathless, trying desperately to get enough air, our bodies glistening with sweat.
Cheryl looked at me, and I at her. We said volumes, but not with any words, no verbal communication, none was necessary.
Instead, we just began to laugh, softly at first, but then growing,until we both were nearly bursting at the seams. I think we were laughing because we were off to a great beginning.
"By the way," she said. "I know the name of a good barber."