First And Second

I wasn’t really in the mood to see Lisa that night but I had never turned down an opportunity. For nearly two years, I had been the guy she turned to for dinner, dancing and movies while sleeping with her abusive, long-time boyfriend. Since she had finally left him back in February, I had taken to optimistically carrying a condom in my wallet but, instead, she went through a succession of lovers while continuing to “date” me platonically. I was a 23 year old virgin and the whole situation was driving me crazy.

It was hot and the weather threatened severity. My bones were still sore from the previous night’s workout. I wasn’t used to exercising and an evening of sit-ups nearly did me in so I definitely didn’t feel like dancing. On top of everything else, I had very little cash on hand. Still, I tossed on my new shirt and splashed on some Brut.

She picked me up as she left work since I didn’t drive. We were argumentative in the car as she drove back to her parents’ house to shower and change and it seemed like hours that I had to put up with her bratty little brothers while she was upstairs. The monotony was broken as she walked by at the top of the stairs wearing just a towel and mooned me!

When we finally returned to the car, Lisa wasn’t even sure where she wanted to go that night but we decided on Maximillians, a favorite nightclub about ten miles outside downtown. It was about 9 PM and the rain was now torrential with non-stop thunder and lightning…and it was getting worse. She pressed on but eventually we stopped at a fast food place on the way to get out of the weather. Things cleared a bit and it was after 10 when we finally arrived at Maxi’s.

I felt exhausted already and even Lisa couldn’t seem to get into the atmosphere like she usually did. She had lots of water and a couple mixed drinks. I had two whisky sours and quite a bit of water myself. As usual, the slow dancing was not as romantic as I would like but she made up for it back at our table, becoming playful and affectionate with tiny little nose kisses. She reminded me of our recent strip poker game where I ended up barely covered in red briefs while she remained almost completely dressed. Embarrassed by the recollection of my failed attempt at seduction, I asked her not to bring it up again but she confided that she had “creamed her jeans” dreaming about it just that morning. She said she was hot and pulled her bra off though her top, stuffing it quickly down into her purse. Watching this gave me the nerve to ask her to see if she could turn me on, promising not to pursue it. She licked the inside of my ear a little but then whispered “not here.”

She got sick in the parking lot when we finally left around midnight and the thought of her “turning me on” was completely out of my head. As we sat in the car, though, she reminded me of it and began rubbing my crotch through my pants with an immediate reaction. I jokingly reached for my belt, offering to give her easier access. Unexpectedly, Lisa said “I don’t care” so I undid my belt, unzipped myself and presented my erect cock to the gaze of the very first woman to ever see it.

“Won’t Get Fooled Again” was finishing up on the radio as she started driving. She stroked me slowly as she got on the interstate and pulled my own hand between her legs where the crotch of her jeans felt hot and humid. I hesitantly reached inside her pants but she offered me her zipper instead. Suddenly, after months of fantasizing, my hand was caressing Lisa’s very wet, very hairy pussy. She told me that she stayed wet nearly all the time and soon my fingers were masturbating her, slipping in and out and rubbing her clit as if I’d been doing it all my life. Her head leaned back and her eyes fluttered over quiet moaning. A voyeuristic truck driver hitting his horn reminded her that she was driving on the highway and she said, “Where do you want to go?”

As we hit the exit, we covered up. We talked about various parking lots but instead decided to see if the newspaper office where I worked as overnight janitor was empty. It was after 1 AM by this point and the place was dark. I went into my apartment next door to the office building to get the keys. I mumbled something vaguely logical to my unconscious father, then rushed back outside, praying she hadn’t changed her mind and driven away. She hadn’t.

We entered the office through the back door as I usually did when going to work. Immediately, she excused herself to the bathroom. I tried to go but my erection kept me from doing so. I gave my face and other areas a quick wash and was back outside the men’s room by the time Lisa emerged, her jeans already removed. As she stood there in pink panties well within eyeshot of anyone who might happen to be walking by the glass front doors at this time of morning, I suggested we adjourn to the conference room.

For well over five years I had vacuumed this room and emptied trash cans and ash trays but I never could have dreamed this would be the site where I lost my virginity: on the conference table in a branch office of a “great metropolitan newspaper.” Inside she lay down on the formica topped table, lifting her ass just long enough to slide her underwear off and toss it aside.

She was quiet now, gentle, sexy and romantic. It was the way I had always wanted her but now I couldn’t keep from nervously wisecracking. She tried to sooth me with a kiss that turned long, hard, wet and deep, her mouth greedily sucking on my tongue until it actually hurt. She sat up and I pulled off her top. In the shadows of the room, I could see her cherry-red nipples pointing nearly a quarter-inch out from her big, solid breasts. I fondled and kissed them wildly, sucking gently on each before working my way all too quickly down to her prize. After asking permission, I kissed her lower lips, still soaking and very hot and began eating a woman’s pussy for the first time. I licked and lapped and sucked and swirled, not really knowing what I was doing but her hands holding my head between her legs and her uncharacteristically soft moaning helped assure me that I was on the right track. My short tongue proved a liability for the job but I added my fingers much to her liking. Several times during my explorations, her legs jerked up and she started shaking. The smell was strong but somehow intoxicating and the taste got better as I went deeper but I couldn’t get in too deep.

She asked me to climb on her. We kissed as I did and she grabbed my volatile cock, quietly egging me on as she slid it inside herself. Almost immediately, however, we realized the table was too hard for this and we moved down to the floor, her hand again inserting my no longer untouched manhood right back into her sheath. Her body was so smooth. She began to rock her hips back and forth and I started reciprocating. It was so slow now, gentle and easy. I looked into her eyes and felt the tight squishiness between her thighs as she squeezed me in ways I’d never imagined. I knew I couldn’t hold out. After less than a minute, one of my forward thrusts was accompanied by my first orgasm that didn’t involve my hand. I had tried with no success to hold it but when it came it seemed endless. “Let yourself come, honey,” she cooed as her eyes locked onto mine.

I started to pull out but she wrapped her legs around me to hold me in place, rubbing her clit hard as she continued riding me to what I assumed was her own trembling orgasm. I never had lost my erection and was ready to go again but she asked me to pull out slowly. She shook almost violently as I did so, lying beneath me looking prettier and more contented than I’d ever seen anyone look. I left the slippery tightness of her vagina trailing a sticky mixture of our cum which dripped to the carpet in a messy stain that I’m certain is probably still there to this day.

In a few minutes, Lisa returned to the bathroom to clean up. She stuffed her panties into her purse with her bra and giggled. I got up the nerve to ask for a blow-job but she said she couldn’t after I had come because semen makes her sick. She added that, “This won’t be the last time, though, so don’t worry.” Still in a fantastic mood, she kept saying how glad she was that we had done it and she asked me to call and wake her up at 7 AM so she could get to work on time. I told her I would be glad when and if it happened again but that I wouldn’t just assume that it would. She drove home. All seemed well.

I was no longer a virgin. We had both wanted it and she had been kind and understanding with me. As we lay there still entwined after it was all over she asked my opinion. Words literally failed me. “Practice makes perfect,” she had said. I came home feeling a bit disturbed that there seemed to be no real, big change. I felt the same and in the mirror, I looked the same. I had little trouble getting to sleep and it only vaguely concerned me that we never used my condom. I had no earthly idea if Lisa was on birth control but I did have some idea of how many guys she’d been with. Still, thoughts of pregnancy and disease stayed in the background as I drifted off happily to sleep.

The next morning, I scrubbed my matted pubic hair, agonized over the stain on the carpet next door and recalled her tangy pussy every time I felt the soreness in my tongue. At 7 AM, I called her and the events of the evening were barely mentioned.

The events were barely mentioned over the course of the next two months, in fact. Finally, in mid- July, after a particularly unmemorable night at Maxi’s, she removed her slip in the car and spread her legs, inviting me to reach up under her skirt to rub her pussy. As before, this continued down the section of interstate known as Death Hill, with her reciprocating until traffic got too heavy.

The night after our first get-together at the office, one of the newspaper reporters had shown up at 1:30 AM to work on a hot story. Had he shown up a night earlier, he would have had an even hotter story. Thus it was that this time, we went to my apartment, slipping past my dad and locking ourselves in my room. I turned on LETTERMAN to muffle any noise. She stripped immediately and after a few rather awkward moments while she seemed more interested in my porn comics than in me, I asked again for her to suck my cock. This time, there on my own bed, she went down on me…but only for a second. As I moaned in pleasure, she stopped cold, remembering my hair trigger from before and not wanting me to come already. I felt dejected but she invited me to suck her “titties.” I kissed her deeply and then continued kissing my way down to her breasts, taking huge portions into my mouth. “Harder!” she demanded. After a brief stop at her belly button, my tongue and my fingers found her sopping vagina. I was much less nervous and more controlled this time. I soaked up the delightful aroma and the sweet and sour taste and made every effort to make her climax, even licking her tight asshole briefly. I wanted to please her so badly but I wasn’t sure how.

Then she surprised me by insisting I skip my recently purchased condoms. “I want to feel YOU inside me.” As I positioned myself, she tried to teach me what she wanted. “Tease me with your cock,” she said. I kissed her hard as she rubbed her clit and my dick at the same time. When I finally slipped easily inside, we made noisy, passionate love. I distanced myself from my own sensations to avoid a repeat of what had happened last time but I tried desperately to make her come and, with the aid of her experienced hand, I did. At the onset of her obvious orgasm, I allowed myself back in the moment and fired off another round into her womb. I pulled out and lay next to her, watching and rubbing myself as she worked herself to another sloppy climax right there in my bed. After that, we lay naked watching TV for quite a while.

From that point on, we rarely saw each other again.