Hard to Get

I met Heather while I was studying law at a large university. I always gazed at the adorable undergraduates walking around campus. Although I was almost 30 years old, I remained shy and rather inexperienced, and I rarely spoke to these girls. Yet their beauty brought tears to my eyes.

Then, one day in a popular coffeehouse, I was sitting alone and reading when Heather asked if she could sit at my table, since there were no free ones left. I vividly remember my first glance at her face: She had the “Brooke look.” I mean, she reminded me of Brooke Shields as a teenager. She looked gorgeous, very young and innocent, but friendly. She had big green eyes, black hair, and small, even teeth. Honest to God, I later found out that she had been a part-time model.

Under the circumstances, I stammered out a, “Sure....” She sat, and we started to talk.

She had a captivating habit of looking straight into my eyes as she chatted. I found out that she had just started at the honors college a month ago. I began to discover, much to my delight, that she seemed to feast off of my opinions, and I freely advised her about classes, extracurriculars, you name it. I managed to stay nonchalant when she talked happily about her boyfriend. Of course she has a boyfriend, I thought: she’s beautiful and smart.

Nevertheless, I flirted as much as I could, and as we got to know each other better, she admitted that her boyfriend went to another school, and that they had agreed “to see other people.” I offered to walk her back to her dorm. She let me, and then at the entrance, smiled and declared, “Can I call you sometime?” Impossible, I mused. She’ll never call.

But, within a week, I heard her soft voice on my answering machine. Next, we had a wonderful, casual date. God knows why, she seemed impressed with me. She even seemed truly excited to ride in my sports car. (I had resigned myself to the fact that guys expressed a hell of a lot more interest in it than women did; I definitely hadn’t bought it to lure models!)

I liked her, too, but what primarily impressed me was her face and her compact, delicious body. I craved her. When she gave me one paltry goodnight kiss, I grinned continually for days.

On casual date #3, she wore tight black jeans and a little sweater that accentuated her flat stomach by ending right above her navel. I finally got her back to my room. Fortunately, she was a little nervous, too, breathing quickly although still looking right at me, and that gave me confidence. We started to kiss on my couch. At first, she just tentatively poked her tongue into my mouth. Already, I was thinking, I wonder if she’s still a virgin? She was definitely holding back a little. Nevertheless, as if she had planned everything and wanted to stay in command, she asked if I wanted to give her a “massage.” (!) She pulled off her sweater and quickly rolled onto her stomach.

I couldn’t believe my luck at getting this pretty 18-year-old in the sack. But, I had a couple of problems since I had never screwed such a slim, small-breasted girl before. There was no clasp on the back of her bra, so I just caressed the thin band of her Calvin Klein sports bra along with her shoulders and back. Then, I figured that I’d reach my hands slightly into the back of her jeans. I could see the outline of her bikini underpants through them, and I wanted to stroke her just down to that line. But, her jeans were so damn tight, I couldn’t do it. My hand got stuck, and I had to take it out!

I was so horny now, I flipped her over and, without much pretense at massage, started to touch her cute little breasts through her sports bra, marveling at how the Calvin Klein insignia circled her taut pale skin. But, I didn’t really know if I could easily yank the bra over her head. So, I just lifted it over her tits. Heather immediately sat up and climbed onto my knee. I leaned forward and kissed her nipple, then softly sucked on it. As it got hard, she let out a little sigh and started to rock back and forth on my leg. I started to suck for all I was worth, and she got more and more aroused and ground her crotch into my knee. I held her by the hips and she enjoyed the friction and sucking. As always, though, she wanted to orchestrate things, whispering, “Keep going, just like this...” So, I did as she humped away, eyes now closed. Soon, she let out a few gasps, moaned, and whispered, “Andrew, I’m cumming!” She shuddered as she came in her jeans. After a few moments, she smiled and, remarkably, said that she “thought that it was time to go.” (She had to study or something!)

I realized that she was an incredible cocktease, but what could I do? I was already her slave, and I let her dress and go without a word of surprise or reproof. At least I’d gotten to second base.

I became frenzied to arrange another date, and this time I vowed to go farther. On the next date, though, I had still more delicious stuff to learn. We were back in my room, on my bed and slightly drunk. This time, I pulled off Heather’s shirt to find a green satin bra with a front clasp. I had never tackled one of these front-openers before! But, after one deep breath, I moved my slightly trembling hands to her chest and unsnapped her bra on my first attempt. I concentrated on her delight, as before. Again, she perched on my knee. I watched as she gyrated, gasped, announced her orgasm, and came.

Now was my chance. I wasn’t going to let her leap off the bed. My hands were already at her waist, and I undid the top button of her tight “CK” blue jeans while rolling her onto her back. Much to my chagrin, they were button-fly. I had never owned a pair of button-fly jeans, nor stripped them off any girl, so I didn’t realize that you could just pull down and unbutton all the buttons at once. Instead, I fumbled at the first damn brass rivet.

After what seemed like eternity, I managed to guide it through the buttonhole. As I forged ahead to the next metal button, my fingers were brushing against the waistband of Heather’s bikini, which matched her bra. Heather thought I was going so slowly in order to tease her, and she was starting to squirm with lust. She urgently whispered, “Hurry up!” She was eager for more sex and, like a sap, I immediately accommodated her. I didn’t take the opportunity to sweetly torture her a little. Instead, I plunged my hand down between her denim and her briefs.

I really had to push a little to get my hand down to her vagina. Her panties were already very wet from her first orgasm, and I just rubbed up against them with the little room my hand had in the confined space of her constricting clothing. I now had managed to get my hand trapped down both the back and now the front of her pants! Still, it worked out great for Heather. The pleasure made her bounce around, but my trapped hand was securely in place and never lost contact with her panty-covered clitoris. She was thrashing and moaning with excitement. Soon, she was murmuring delightfully: “Aagh! Oh, it feels really good! I’m starting to cum again!” Then, she was convulsing again, and my fingers felt her bikini suddenly get even more juicy.

Now, as she relaxed and caught her breath, I had ample time to undo the rest of her fly and pull her tight jeans down her legs. It was then that she smiled shyly at me and said that she wasn’t ready to go all the way, and that we should leave on our underpants. So, I obeyed again, and I went down on the beautiful freshman, vigorously licking then nibbling at her satin panties. Occasionally, I would push the panties in and out of her slit. Then, I’d lick her clit again. She shoved her crotch at my face and pounded her little fists against the bed. Groaning out the single word, “Orgasm!,” Heather treated herself to a third climax.

I so wanted to fuck her now, but she explained that she was still a virgin ( — was she really a virgin? She appeared at the same time to be kind of innocent and yet selfish and slutty), and that she even prevented her boyfriend (I’d forgotten about that jackass!) from getting too carried away by making sure they always left some clothes on. She confided, though, that his “thing” was so long that it sometimes poked its way over the top of his shorts. Well, that didn’t make me feel so great, especially since, so far, she had only indifferently rubbed my dick. As you will imagine, I wanted to prove myself and take control (for a change).

She seemed a little tired, but I kissed and stroked her some more to get her heated up again. It worked, and as I caressed her vagina, this time I worked a finger into her. She seemed a little startled at first, but then her face got contorted with ecstasy. I guessed that this wasn’t a first for her, no matter how innocent she acted. Still, she was hungry for experience, and could hardly stand the joy of fucking my finger. More juices poured out of her, and this time, she whispered: “Hurry! I’m almost there! Please, Andrew, make me cum one more time!” She was shivering and tense, at the brink of climax.

At that moment, I abruptly stopped, to show her up some more. I quickly got on top of her light body, helped her wrap her legs around me, and started to hump. Heather went wild with lust. We mashed our underpants together. I concentrated on keeping my cock pushed against her most sensitive spots. I felt her wetness seep onto my briefs and even onto my penis underneath. As I began to ejaculate, I reached down and made sure that my cockhead was free. It felt much better that way, and I creamed all over her little flat stomach and satin underpants. I had an amazing orgasm – after waiting so long! – while my young bedmate demoniacally pushed against me, setting off her own. Because I’d kept her waiting, too, this orgasm, her fourth of the night, was her most intense. Heather cried out and rolled her head from side to side as she came once again in her panties.

The pretty freshman was all tuckered out from sex and fell asleep next to me. I was elated. Although I probably realized that I could never keep a girl like that for long, I couldn’t hide my shock when I called her the next week to arrange a date: She was cold, and gave me some excuse about an appointment that evening with her teaching assistant. Good luck to him, the bastard!