Start of a Beautiful Friendship

I met Jackson at the university. I had taken a few years off from school, and was a bit touchy about being back in classes with people several years younger. Thankfully I look about five years younger that my actual age, and I soon figured out that the guys at school either didn't know or didn't care about my age difference. Of course, having an hourglass figure with perky D-cup breasts probably helped quite a bit, too. I'm still pretty sure my breasts are why Jackson first spoke to me, although he denies it.

I was in the hallway outside my first class, waiting for the preceding class to let out and mine to start. I guess I still looked a bit out of place, because as he came out of the class and started to walk past, he asked if I was looking for a certain professor and offered to help. I thanked him but told him I was waiting for the next class. He chatted me up a bit, but I wasn't really paying attention to his words. He was of average build – athletically lean and decently toned, but not overly muscular – with close cut blond hair, a very angular face, and deep set eyes that seemed to change color from grey to hazel (depending on his mood, I would find out later). Unconventional but handsome, was my assessment as I went into my first class.

It took a few months for us to actually become friends, but after a wild night of drinking and a game of strip-poker, we found some common ground. Some of that common ground included strong sexual curiosity and mutual attraction. He confessed that he had some wildly erotic dreams about me, which I found exciting and arousing. I had never encountered anyone so frank and comfortable with sex. Jackson's easy confidence in all circumstances was extremely attractive. As we started talking about our fantasies more frequently, I knew I wouldn't be able to hold out for long before succumbing to my desire.

One night, after too many margaritas, I ended up at his place with plans just to crash out for the night. In true college guy fashion, he had a futon and a couple of chairs, but no other bed or sofa. He said he never slept much and would probably work on a project at his desk for most of the night, and I was welcome to take over the "bed." But suddenly I started thinking of the sexual talk we had shared, and I was no longer tired. I just didn't know where to start. Although I was comfortable with my sexuality, I had always been kind of shy for my first time with any guy. Jackson was sitting at his desk, half turned away and seemingly uninterested. There was a blanket and a couple of pillows on the futon, so I took off my shoes and started to lie down with my clothes on, unsure what to do.

He glanced over at me with a raised eyebrow, "you're really sleeping in your clothes?" he asked with amusement.

I blushed, but realized this was my opening. "I guess not," I replied, standing up.

I slowly pulled my blouse off over my head, smoothing my auburn hair with one hand as I draped the shirt over a chair with the other. Now I had Jackson's attention. Locking eyes with him, I slowly unbuttoned and unzipped my jeans. I sensually slid my hands down my hips, pushing my jeans down and easily stepping out of them. Aroused, my breasts strained against the sheer creamy lace bra, pink nipples visible through the embroidery. The matching thong emphasized the curves of my hips and ample but shapely bottom. Jackson couldn't take his eyes off me. He licked his lips, and then shook his head slightly, like he had forgotten where he was for a moment.

"Turn around," he told me, as he stood up and started unbuttoning his shirt. His eyes were dark with lust and his gaze ignited a fire somewhere deep inside me.

I started to smile, but bit my bottom lip to keep from grinning at my seduction success. I slowly turned my back to him, my heart racing as I trembled slightly with nervous anticipation. I glanced over my shoulder to see if I should turn back again just as I felt him press against me from behind. He brushed my hair away from my neck and kissed me softly on the shoulder, then slowly kissed and nibbled his way up towards my ear. In the meantime, his hands were firmly squeezing my tits as his erection, eager to be free from his khakis, rested solidly between my butt cheeks.

"I know your fantasies," he whispered in my ear as he slid my bra straps off my shoulders.

He spun me around quickly to face him and pushed me against a nearby wall, pinning my hands above my head with one hand as he grabbing a fistful of my hair with the other. I inhaled sharply both from surprise and arousal. He smirked slightly at seeing my heaving breasts, knowing he was having quite an effect on me. He pulled my hair tighter as he kissed me deeply. One of my hands was free again, and I used the opportunity to undo his pants and explore what he had to offer.

I won't pretend I hadn't snuck a glance or two at his crotch before, but he wore his pants kind of baggy at the time and I really hadn't been able to size him up. I suddenly realized he wore baggy pants to have room for a fantastically large cock! I gasped slightly, feeling the thick bulge through his underwear that just kept going! Noticing my excitement, Jackson smirked and released me from the wall and stepped out of his pants so that I could get a better look.

Eager, but not wanting to rush, I shyly glanced down at his package, still covered by grey boxer briefs. I bit my lip again to avoid grinning and stepped towards him. I unhooked my bra and let it slip to the floor, allowing my breasts to graze his chest as I ran my fingers lightly up each thigh, across his balls, and up the length of his shaft. Then I slowly pulled down his boxers, my tits tracing the length of his torso, sliding down either side of his dick, until I was kneeling before him. From my new view, I could see he was 8 – 10 inches, straight, and wonderfully thick. My warm breath and the slightly cool air made it twitch slightly, releasing a bit of pre-cum that glistened on the tip. I looked up at Jackson, asking permission with my eyes, and he grinned and raised an eyebrow in encouragement.

Using the backs of my fingers, I traced the length of the underside of his cock from the balls to the tip. Then I placed my hands on his thighs for balance and retraced the same path with the tip of my tongue, lightly lapping the pre-cum at the end. I gently grasped the shaft with my hands and pressed my lips to the tip, adding a couple more teasing licks before taking the head in my mouth. Because of his size, I could really only go about halfway down on him with my mouth, so I used my hands to stroke his shaft and massage his balls as I sucked on him.

After a few minutes of this play, I was really ready for a serious fucking. After a few sultry glances up at him, Jackson finally decided it was time, too. He pulled away and offered a hand to help me to my feet. He led me towards the futon and pulled me against him again, kissing me as he squeezed my soft, smooth ass with his warm hands. Then he yanked off my thong and playfully shoved me back onto the bed. He deftly slid on a condom and was on top of me in no time. He glided his shaft along my hot, wet slit a couple of times as a tease, and then positioned himself at the opening.

As he plunged in, I couldn't help but moan with pleasure. I was so wet that he had no trouble sliding in, and he filled me completely. He pinned my wrists down with his forearms and slowly drove the full length of that glorious cock in and out of me a few times, making me moan slightly with each re-entrance. But he couldn't hold back for long, either. Soon he was pumping me at a good pace, and I could feel the heat and tingling starting to build inside.

Wanting to prolong the ride, I rolled us over so I could be on top for a bit. He smiled at my smooth maneuvering and took advantage of my new position by grabbing a breast in each hand as I sat on his pole and slowly slid up and down, squeezing with the walls of my pelvis. I leaned forward a bit and pick up the pace, enjoying the feel of him filling me from each new angle. Of course he was saving my favorite position for last.

In sharing our fantasies, I had confided that I love being taken from behind, especially while having my hair pulled. He pulled out and flipped me over so that I was in position, and grabbed a fistful of my hair. He once again plowed into my pussy, and I nearly came right then. I did shriek with pleasure! He grabbed a tit with the other hand and pumped me hard and fast. I bit my thumb knuckle in an attempt to stifle my cries of ecstasy, but it did little good. My orgasm broke so hard I started to tremble all over as my pussy walls clamped down on his throbbing cock. At this, he lost it too, and moaned slightly as he came, emptying a few loads of cum into the condom. Both spent, we slept through the night, dreaming of future adventures together.