Abigail

In the last six years (and in the past three years in particular), I have enjoyed some incredible sexual experiences with a fair number of amazing women. Of those women, I would say three of them have had a special, inexplicable grip on me: Jessie, Michelle and Abby. My adventures with Jessie are well-documented (though I have, admittedly, left out some of the best ones). I have happily fulfilled just about every reasonable fantasy I have had with her. Michelle, on the other hand, also helped me satisfy several desires, even ones I didn't even realize I have, although my relationship with her turned out be far from the norm.

Then there's Abby. Neither of the situations I previously described are as maddening as the one I have with this young woman. She elicits all the same wild fantasies, has the same obsessive pull on me and even has gotten my hopes up a number of times for ongoing debauchery, and yet, while I've had my share of fun with her, my time with her has always been fleeting and short-lived.

Abby was a tease right from the beginning, but it's not like she did it on purpose. She is actually a very sweet, very cute young lady. I first met her seven years ago, back when she was just shy of 18 years old (so not a girl with whom I was going to consider having a sexual relationship.) However, it wasn't anything sexy that drew me to her first anyway.

I still remember the day I met her: we were working a summer job together while she prepared to finish high school and I college; she wore red gym shorts, a blue tank top and black flip flops; her light brown hair came down loose to her shoulders, swaying as she sat down beside me that first day of orientation. She was objectively cute, too, with her slender frame, bright green eyes and light freckles that were all but covered up by her makeup. All she needed was just a little more time to mature.

There was an undeniable chemistry between Abby and me, but she was still too young and, oh, had a boyfriend, as I came to find out. Despite her relationship status, she was very friendly with me to the point that I thought she liked me, though it really didn't make sense. Regardless, I always enjoyed when we worked together and decided I wanted to stay in touch with her in case circumstances changed in the future.

We did end up keeping contact, occasionally through texting and fairly often through social media. She was 18 before I knew it, at which point I began to initiate more of the communication (usually it was she who started out chats.) Two full years would go by without my seeing her, but I kept an eye on her, figuratively speaking. It all led up to one day when I was working the job at the company for which I am now still currently employed, and I found out that one of my coworkers was a mutual friend of Abby's.

Through this friend, I came to learn that not only did Abby dump her boyfriend recently but that Abby had "a huge crush" on me. To that comment, I smiled and said, "I think she's really cute." This friend insisted that I give Abby a call but to wait until she had spoken with her. I had waited two years, so what was a couple more days?

The next day, this mutual friend informed me that she had told Abby how she had given away her crush and how she had told Abby that I thought she was cute, which had apparently made Abby smile like a fool. The time was finally right. That night, I called Abby and asked her out on a date that coming weekend.

Abby and I went out for a couple weeks before the sexual tension reached a fever pitch. She was now 19 and had already given her virginity away to her former boyfriend but was ready to try sex again. Even though I was a little older, Abby and I had in common that we had slept with just one other person. In fact, I had had sex just once in my life going into this night, mostly by choice but, in retrospect, I realize I kept myself out of a lot of situations that would have led to intercourse. This night with Abby was not going to be one of those times that I missed out.

The only other time I had fucked a girl was an impulsive one-night stand, so this night with Abby was going to be special. At the time, I had roommates, but they agreed to give me the place to myself that night. After another lovely date with Abby, I brought her back to my place where my roommates had done a nice job of making sure the place was clean and didn't smell like three bachelors. I immediately took Abby back to my bedroom, where we made out and let the fire burn a little.

Abby looked as good as I'd ever seen her. Her makeup made her face glow perfectly in the light of my room, and her hair was perfectly straight, a bit of a darker brown than when I first met her and going past her shoulders now. She wore a leopard-print tank top that hugged against her small, handful breast that were just right for her frame. For pants, she had black capris that were the first thing to come off while we made out on my bed, revealing a black thong. With her pants off, Abby ground on top of me, making my cock nice and stiff as it longed for her.

As she kissed me, Abby finally reached into my jeans and grabbed my dick, immediately stroking it to full size. My hands ran down her back and slid into her thong, squeezing her ass cheeks for a moment before sliding back up and pulling her top with them. Abby released my prick for a moment and raised her arms to allow me to take the garment off her, leaving just her matching black underwear to cover her sexy teenage body. Then she went back to stroking my cock, this time pushing my pants away to allow my member to breathe.

Still allowing the young girl to beat me off, I rolled her onto her back, still kissing her passionately but now on top of her. Then I quickly disrobed myself and then directed my attention back to Abby, who smiled up at me, her hand at any given time either stroking my prick or reaching for it if I had accidentally pulled it away from her during the course of my movement. With that soft hand's sliding up and down my shaft, I slid my own hands underneath Abby's back to unlatch her bra and take it off entirely.

Unfortunately, Abby had to let go of my penis to let me take the bra off her, but it was worth it to finally see those lovely boobs. Without hesitation, I first put my hands on them, squeezing them and rubbing my thumbs against her hard nipples. Abby moaned and grabbed my cock again while I fondled her tits, at which point I thought of a better use for both my dick and her breasts.

I shifted up, and, as soon as Abby saw what I was doing, she squeezed her small boobs together and allowed me to slide my cock in between them. She smiled and looked up at me as I began to push my cock up and down between those luscious breast, enjoying my first titjob. At one point, Abby even lowered her head and stuck out her tongue in order to lick the tip of my phallus each time it pushed up between her teenage boobs. When I realized Abby was OK with tasting my cock, I decided to give her all the meat she could want, pulling away from her tits and offering my manhood to her lips.

Holding myself up on the headboard, I lowered my cock at Miss Abby's mouth, which accepted it, as Abby lifted her head up slightly, taking the base of my cock in her hand as she sucked me off. I sighed and moaned as this beautiful girl gave me a blowjob, driving me to the brink of an orgasm. Her wet tongue and pretty lips slid up and down my entire shaft over and over again until I had no choice but to pull away, desperate to not lose my load until I had at least had actual sex with her.

Abby tried her hand at some dirty talk after I pulled my cock out of her mouth, and it worked pretty well, though I was already entirely turned on. I hurried to the other end of her, pulling her thong off quickly as I wanted so badly to make love to her now exposed pussy. The only other woman I had fucked up to this point in my life was a 30-something-year-old who, I had since found out, was somewhat of a whore, so I was not only excited to be finally scoring with a girl like Abby but also to see just how tight that teenage pussy was. First, though, I wanted to return the favor she had given me.

Now completely naked, Abby spread her legs as I knelt in between them. Before going all the way, though, I ate her pussy for a few minutes first. Abby wasn't expecting the oral treatment and was delighted to feel my tongue slide in and around her womanhood, her excitement evidenced by her moans and the thrashing of her legs. Still as hard as an ice pick in a snow storm, I held sweet Abby's legs apart and devoured her cunt the best my inexperienced mouth could. I seemed to be doing just fine on the sexy little teen, who squirmed and moaned with approval throughout.

At last, we were ready to consummate this date. Abby continued to hold her legs wide apart and reached down with one hand to help me push my rock-hard prick into the folds of her young vagina. I leaned forward, pushing the tip of my cock inside the young girl and then forcing inch after inch of it past those pussy lips while we both moaned in unison until my balls touched her taint. Fully sheathed inside my young friend, I was ready to give her the best sex I could.

Now I lay down on top of Abby, her boobs smashed against my chest and her tongue in my mouth as I started to fuck the cute teenager. Instantly, my cock was pumping in and out of that terrifically tight twat, which flowed with juices as it clung to its welcomed intruder. Abby wrapped her arms and legs around me, her ankles crossed over my lower back as they bounced with the steady thrusts I gave her sexy body as I fucked it hard and fast right from the start.

The room heated up quickly, and we were sweating in no time. Once the realization that I was banging my beautiful friend had fully set in, I was able to control my pace better and allow our intercourse to last a little longer. We both moaned into each other's mouths as I pounded Abby hard, my cock going as deep inside that young cunt as I could possibly force it, evidenced by the sound of my balls' slapping against Abby's skin.

Just a few minutes before our climax, we rolled over so that Abby was now on top. I held her in place at first and continued to pump into her pussy while we made out, but after a minute, Abby went upright, planting her feet on either side of my waist as she leaned back and put a hand on each of my knees. Once she was balanced on my cock, she began to slide up and down it, slowly at first, but soon going very quickly. Her hair and boobs bounced before my eyes as her sexy young body shot up and down my engorged phallus, which was getting ready to burst. All I could do was squeeze Abby's ankles and call out her name while she called out mine.

My bed creaked at an ungodly volume beneath us, and I noticed sweat dripping between Abby's breasts while the girl moaned and fucked my dick like a champ, riding and grinding on it with what appeared to be experience beyond her years. I did my best to pump up into her too, working together with her to achieve blissful orgasms for each of us. As I felt my climax nearing, I reached up to hold onto Abby's waist and then sat up, getting Abby on her back again, but this time I remained on my knees while my hands remained on her waist as I plowed her tight pussy.

Just moments before I came, Abby clutched the sheets beneath her and cried out, kicking her legs up as she climaxed right before I did. Her pretty green eyes fluttered shut, and her body went rigid as she moaned loudly while my cock continued to plunge in and out of her convulsing pussy over and over again. When her orgasm began to subside, Abby invited me to cum on her boobs. Naturally, I didn't object.

I exited Abby, who was panting and heaving as she recovered from her orgasm, and beat off, feeling Abby's fresh juices on my shaft. Abby held her boobs together, still breathing heavily as I moaned, growing closer and closer to cumming before my prick finally exploded, showering Abby's tits with shot after shot of jizz until my cumshot tapered off and dripped onto her stomach. I managed to keep my eyes open the whole time so I could watch my seed plaster the pretty girl's chest, and I'm glad I did so. Watching Abby grin from ear to ear while my white cum coated her boobs is an imagine I'll never forget. Once I was satisfied with my work, I rolled over and collapsed next to Abby on the bed, both of us now recovering from one hell of a workout.

Unfortunately, what I thought was just the start of something wonderful turned out to be an anomaly. Abby and I failed to have sex a second time during that short-lived relationship as we saw each other only a couple more times before Abby revealed that she had actually been seeing someone else but hadn't said anything - to either our mutual friend or me - because she really wanted to spend a night with me. While I was thrilled to have succeeded in making it with Abby at least once, I was devastated by the news that it wasn't meant to last.

It would be another two years before I would see Abby again, and it was under pretty special circumstances: I would hire her as an employee at my company. At this point, let me inform you that a more detailed account of this part of the story is already in my post "Showing Abby Who's Boss." However, there are some alterations to that version. The following is presented exactly as it happened:

I called Abby immediately after receiving her resume and set up an interview for the following day. While personally I was excited at the prospect of being Abby's boss, professionally I honestly wasn't sure if Abby was the most qualified candidate for the job. Of course I was going to give it to her, but in my mind she was still the 19-year old with a history of immature relationships, including when she fucked me without telling me she had a boyfriend a couple years ago. The work required in the position for which I was hiring demanded more than entry-level skill.

On the day of the interview, I greeted Abby for the first time in two years. I began to realize right away that I had been harsh to judge her based on my experience with her when she was 19. At 21 years old now, while she still had a lot to learn, she came of as a very capable and competent young woman. She went on to nail the interview from start to finish: arriving early, dressing professionally, presenting an impressive cover letter and resume (for a girl just finishing college) and answering all my questions very well. Of course, the meeting was a little awkward, and I still felt a pained, given our history, but I too had matured since then and was willing to forgive and forget. After I dotted a few i's and crossed a few t's, Abby had the job.

Abby continued to only impress me. She caught onto the job duties quickly and was one of my top performers within a month. She was also just as cute and friendly as I remembered her, only now she was more mature. Without even realizing it, I was spending more time than I needed to with her at work, and we were drawing out email conversations to an extent that was no longer professional. Things between us were going so well both personally and professionally that those fantasies soon returned, although I originally had no intent on carrying out my thoughts.

Eventually, the chemistry and sexual tension between Abby and me reached an all-time high, and we already knew how it had culminated two years prior. Abby was still performing admirably at her job and was more and more often the star of my lustful fantasies. Within a few months of Abby's working for me, I was at a place in my life where I was no longer satisfied with just thinking about my cute employee. I was going to pursue actually fucking her again, thinking this time would be different.

Becoming personally involved with an employee was risky, obviously, no matter who it was. I knew, it wasn't wise to look for anything serious with Abby, at least not right away. Just a fun time and a good story was all I needed, especially considering the pain Abby had caused me in my past. And even though I had fucked Abby once before, the fact that I was her boss made it even hotter this time.

Very little effort was required on my part to get Abby and me to a place in our friendship where we were ready to give sex another try. Within weeks of my pursuing a sexual relationship with her again, were in her apartment one night to do the dirty deed. We had always had enough trouble staying away from each other as it was, so the boss-employee dynamic that was a part of it this time made it totally irresistible.

Abby's apartment was very neat and clean, more so than one would expect, as if she'd prepared for my arrival. The dwelling seemed kind of big for just her, but she insisted she did not have a roommate. Also, there was no way she was affording this place by herself on what I was able to pay her, but I just assumed her parents were covering some bills for her or something. It was the only scenario that made sense, especially since she told me she had just started school again. All the signs were there that history was repeating, but I didn't want to see them.

We were too excited to do anything other than head to the bedroom. We made out a little as we stood in the living room, marking the first time I ever kissed a girl who worked for me. When we entered the bedroom, I was greeted by a sweet smelling scent and a large double bed against the far wall. In this room, too, everything was cleaned and organized. There were a couple candles on the nightstand that Abby lit as soon as we entered so that there was no need to turn leave the light on, so I turned it off. In just a few seconds, the smell of lilac began to join the already sweet aroma in the room.

After some touching, I pushed Abby down on her bed. The mattress felt relatively new, very soft and comfortable. We made out for a couple minutes before I backed off to allow Abby to unbutton her shirt, revealing a pink push-up bra. As Abby worked on her top, I knelt beside her and pulled her pants clean off her body, knocking her shoes off with them. At that point, I started to take my own clothes off, and from there we continued until we were both completely naked.

As soon as the pink bra hit the floor beside the bed, my naked employee pulled the blankets up and slid under, taking her bare boobs away from me as soon as they had been presented, and invited me to join her. I eagerly complied; after all, even as the boss, I was always open to the suggestions of my staff. As soon as I joined her, Abby took my already raging cock in her hand and stroked it vigorously. She smiled as I sighed, the two of us lying on our sides while she jerked me, her soft hand sliding quickly up and down my stiff erection.

After stroking my cock for about half a minute, Abby slid her head under the covers, causing my heart to leap as I prepared for the next level of pleasure. For the next few minutes, she sucked my cock, which she continued to hold at the base. I lifted the covers so I could look in and make eye contact with my favorite employee while her head bobbed up and down, her tongue pressed against my shaft. While she demonstrated her cock-sucking ability, I uttered the words, "Fuck me, Abby."

"Yes, boss," she replied, pulling her head back and jerking my now slick penis. I hadn't even been going for the boss-employee dynamic there, but I'm glad she took it that way.

Emerging from the covers, Abby spread her knees so that they were planted on either side of my hips. My cock was now pressed against her shaven pussy while the blanket rode around Abby's waist. She looked up at me one more time, those green eyes reflecting the candlelight, which also cast a warm glow on her freckled face, though her freckles were, as usual, mostly obscured by her makeup. Then she looked back down at my cock as her light brown hair hung down around her neck and shoulders. Abby grabbed my cock, slightly lifting her body, and slipped my member into her pussy.