Sexploits Ch. 07: Abigail Pt. 02

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Abby gets my hopes up one more time.
3.7k words
4.72
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Part 7 of the 11 part series

Updated 06/08/2023
Created 12/14/2016
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dpingjessie
dpingjessie
1,152 Followers

The following is an account of an unexpected turn of events in this documentation of some noteworthy sexual experiences. While there are certainly at least a couple episodes that would have been worth adding, it was in my interest to cut right to the new development. Sadly, this account will be as short-lived as said development, as I wasn't even able to put my fingers to the keyboard before my hopes were dashed yet again by one particular female who has held a soft spot in my heart for the better part of the past seven years.

Abby, the girl I speak of, was a co-worker of mine several years back who, I found out, had a crush on me but also had a boyfriend. We remained in loose contact over the next couple years, including when she dumped that boyfriend and went out with me for one glorious night that culminated in passionate intercourse. While I had thought I had finally found the girl of my dreams, it turned out she had already been going on a couple dates with another guy, whom she more or less committed to in the coming weeks, thus leaving me out in the cold. It was only a part in a small string of women who let me down, but Abby really left a sting.

We reconnected a couple years later again when I had the opportunity to hire Abby into my department at work. She led me to believe she was single again, and our work relationship, over time, developed the same friendly and sexual chemistry it had previously posessed. We ended up having sex a couple more times, including one particularly hot and risky session in my own office.

That time ended like the first, only much more painful. Not only did I find out again that Abby was committed to someone else, I found it out through an engagement announcement! You can imagine the agony and humiliation that news caused me. It was the last nail in the coffin when it came to my faith in a normal, meaningful relationship with a girl. It was around that time that I gave into the sort of escapades I have documented to this point.

Over the course of the next two years, constant rumors surrounded the couple. They did get married, but it seemed like there was always some kind of tumult linked to them. It would be far outside my bounds to even hint at what some of those issues were alleged to be, but it was very clear that Abby had every right to doubt the longevity of that commitment.

There were even a couple times where Abby began to confide in me some of her discomforts, to put it in euphemistic terms, and refused to go home that day. On more than one occasion, I invited her to stay at my place for the night, my full intention being to sleep on the couch while she took the bed. More often than not, it went down just like that, but on two separate occasions, my flesh won out, and Abby and I had very enjoyable sex, adding up now to five times that I experienced the joy of a physical relationship with the cute young woman.

I did draw the line, though, after that last time. I wasn't going to violate my conscience and fuck a married woman like that again, no matter how poorly her husband treated her and probably deserved it. Abby received the message loud and clear, and though I didn't mean to have her back off, she stopped confiding in me at that point.

Everything changed in May, though. I had long since written off any future with Abby. She didn't even work in my department anymore after she took a different position with more pay, so I was no longer her boss. I hardly saw her at all for several months until I happened to bump into her last month, which is when she asked me if I wanted to grab a coffee after work. I didn't see the harm in a cup of coffee, so I agreed to it.

It was over that coffee that Abby told me she had separated from her husband and the divorce was in process. I knew the split-up was in her best interest, regardless of my attraction to her. I asked her where she was staying, and she said with her father for now. I offered my place if she ever needed it, and she thanked me but didn't take me up on it just yet.

Over the next couple weeks, Abby and I talked more and more, just like we did the last two times our relationship took a turn toward romance. At last, she said she was going to bring a few bags to my place, if my offer still stood. Of course it did! I told her she could settle in after work, and then we could go out to dinner. She smiled bigger than I had seen her do in a long time and accepted my offer.

My excitement was barely containable the rest of that day. It was about more than just the chance of reconnecting with Abby and finally having a chance to maybe settle down with her. It was about my life's coming together. Obviously, I had had my share of fun over the past few years, and speaking to my sex life specifically, I had enjoyed some wild and unbelievable expriences that I counted myself fortunate to have. But I knew the pattern of group sex and casual encounters was not a sustainable pattern and not something that would satisfy me long-term. With Abby, I saw a chance to move on to something more real and lasting.

I helped Abby settle her stuff in that night. As always, I offered to sleep on the couch, but she insisted we could share the queen-sized bed. I didn't argue. Then I told her to feel free to shower and then get dressed up, because we were going to grab a nice dinner.

She took my suggestion very seriously. When she finally stepped out of the bathroom, she looked absolutely stunning. The young, goofy girl I had met seven years ago was all grown up now! The first thing I noticed was her hair, which had been in a ponytail before but now hung straight down, framing her face. It wasn't her natural color, which was light brown, but instead a slightly dirty blonde with brilliant bright streaks through it. It contrasted nicely with her big green eyes, which had always melted my heart no matter how much she played with it. Her mastery with makeup only accentuated those beautiful eyes and lips while all but covering up her freckles on her pale flesh.

Equally attractive was her outfit, starting with open-toe white and black high heels that I guessed were about three inches tall and brought her total height to maybe 5'6" or 5'7." Her matching white and black skirt came a couple inches short of her knees, revealing her slender legs and hugging her hips and ass in the sexiest way possible. For her top, she had a tight black blouse, low cut to show off the beginning of her cleavage. Her breasts looked so much larger and fuller now than they did at 18 years old when she first met me, and her shirt and bra pushed her boobs up and together just right to make her all the more desirable. She topped the whole thing off with a bracelet around her right ankle and a necklace that were a matching silver.

It took all the self-control I had to not ravish Abby right then and there. However, tonight was about romance, not lust. Either way, it was hard to not stare at her. The girl who had always been so pretty never looked better than she did this night. It truly seemed like everything was coming together for real this time. I was more than ready to let go of all the debauchery I had enjoyed the past few years to latch onto my beautiful, sweet friend.

Dinner was perfect. We chatted, we laughed and we ate. She confided more and more in me, and I did the same with her. The whole time, I was stunned by her beauty and wondered how I had gotten so lucky to spend this night with her after all these frustrating years. Patience really appeared to be paying off.

I took her back home after dessert, and it was no secret to either one of us what was coming next. As Abby freshened up in the bathroom, I set the mood in the bedroom with a few candles. She was pretty impressed when she finally entered the room, looking as stunning as ever in the warm, dim candlelight.

As Abby stood by the door, I wasted no time, walking up to her and holding her in a tight embrace as I kissed her. I had thought I would never touch those wonderful lips again. As she held me and kissed me back, we shuffled over to the bed, pulling at each other's clothes but not yet successful in removing any of it.

As we made out, I pushed Abby gently onto her back, kissing her lips and tongue as my hands moved down to her skirt. It took a second to locate the zipper, but once I did, I loosened the garment and began to pull it down, all the while never taking my mouth off Abby's. Meanwhile, her hands rubbed up and down my back before moving to my chest to begin unbuttoning my dress shirt.

At last, I pulled away from the kiss so I could get that blasted skirt off, and Abby took the opportunity to remove my shirt. With both of those articles tossed aside, Abby immediately took her shirt off and then just as quickly removed her bra, relasing those lovely boobs. Trying to keep up, I slipped my shoes and pants off, along with my underwear, revealing to Abby just how excited I was to spend this night with her.

Abby grinned from ear to ear at the sight of my erection. She then kicked off her shoes and removed her necklace. I asked her to leave the bracelet around her ankle because I thought it was sexy, so she obliged. Honestly, I would have liked her to keep the high heels and maybe the necklace on too, but I wanted her to be comfortable. As corny as this may sound, tonight, unlike most of my episodes, was about making love and not just carnal passion, though that element certainly has its place even in romantic intercourse, as it would tonight.

Abby and I made ourselves comfortable on the bed. She lay on her back as I held myself over her, smiling at her as I first gazed into her bright eyes and then traced down to her breasts. I then lowered my head and put my hand on her left boob, squeezing it hard, while proceeding to lick and suck the other one.

Abby cooed and squirmed as I played with her tits, moving back and forth between them so as to give both of them equal attention. After a minute or so, I moved my mouth downward, kissing down her stomach before arriving at her shaven pussy and the goal of tonight's endeavor.

By that point, I wanted badly to shove my cock inside that wonderful hole, but the only thing I wanted more was to maximize Abby's enjoyment. With that desire in mind, I spread her twat and stuck my finger inside, slowly working it all the way in to find just how wet she was. Abby cried out and squirmed some more against the mattress, telling me how good it felt and how badly she wanted me to fuck her.

I persisted, sliding my finger in and out of Abby's delightful pussy, lowering my head and licking her clit as I fucked her manually. Abby put her hands on my head and bucked her knees up, moaning even louder as I now alternated between licking and fingering her womanhood. I continued the oral sex until Abby literally begged me to fuck her.

As soon as I pulled my finger out, Abby quickly switched to her hands and knees, asking me to do her from behind. I wasn't going to be picky when it came to making it with my long-time crush, so I saddled up right behind her as she looked over her shoulder at me, he shoulder-length blonde hair hanging down in her face as she waited for me to enter her. We were both ready for this perfect night to finalize with this last blissful activity.

As soon as I pressed the tip of my cock inside Abby, I put both hands on her hips and slid all the way inside her, groaning with pleasure as I filled her tight, wet insides. Abby moaned as well, holding herself up by her rigid arms as she continued to look over her shoulder at me. Once my balls touched Abby's clit, I went right to work at fucking her.

Slowly at first, I slid back and forth in and out of Abby, gently making love to her as my mind swirled with love, lust and other emotions. Even though we had had sex, if my memory serves me right, five times before over the past several years, this time felt like the first. It felt like the culmination of all the frustration and pain I had received at the hand of Abby and, really, any woman, which was now being released. While our previous exploits had been more or less carnal and casual, this one had an intimate connection we had never before achieved.

Caught up in the moment, I pumped harder and faster into my dear friend, forcing her sexy body slightly forward each time I slammed into it. Abby was either grinning and laughing or closing her eyes and moaning as she took my steady thrusts into her at the other end. As I gripped her flesh tighter, she held onto the sheets beneath her as if for dear life as I nailed her from behind over and over and over again for several more minutes.

Just as I felt my balls begin to well up, I quickly readjusted, slowing down to keep this wonderful experience alive for a little longer, especially since Abby had yet to achieve an orgasm. I asked Abby to get on top, and she responded that she was happy to do so. I was reluctant to pull out of that perfect pussy, but the thought of Abby's riding me in just a moment was all the motivation I needed to follow through.

I got to my back, and Abby climbed on top of me, squatting over me and planting her feet on either side of my hips while she leaned slightly forward and reached down for my cock, which was coated in her juices. She steadied my member beneath her before lowering her beautiful body down and impaling it on my rock-hard penis. Moaning in unison with Abby, I wrapped my hands around either of her ankles, the cool metal of the bracelet on her right ankle pressing against my hand, and stayed still as Abby slid slowly down my shaft until she was sitting on my balls.

Now pushing her hair out of her eyes, Abby smiled at me and began to rock her body up and down, gently riding me at first, careful to take my whole dick inside her each time she came down on me. For the next few minutes, Abby's hair and boobs rocked up and down as her body rode me steadily harder and faster. Meanwhile, my hands went between grasping Abby's ankles and squeezing her boobs as she fucked me more and more intensely until she was huffing and panting as a result of her exceptional effort in lovemaking.

We both moaned as Abby continued to bounce on me. Every time our eyes met, we would share a smile, and Abby would giggle with amusement or affection. By now she was working up a bit of a sweat, as perspiration was forming on her shoulders and between her tits as they bounced up and down with her body

It wasn't long at all until I began to feel my balls ready to burst again, but I still wasn't ready to be finished. Instead, I quickly pulled Abby down on top of me, holding her still and rolling her onto her back. In the process, my cock slipped out of her, but it wouldn't be long until I was back where I belonged.

As I moved her, Abby sighed loudly, complaining of how frustrated she was that she kept getting close to an orgasm but couldn't pull the trigger. I promised her I would get her there as I quickly pushed my cock back inside her and then lay down on top of her, going balls-deep into the lovely 24 year old woman beneath me. As I joined myself to her one more time, Abby cried out, saying how she loved the feeling of my stiff cock's penetrating her. Once the words were out of her mouth, I wrapped my arms around her back and kissed her just as I began to thrust in and out of her cunt.

Abby enclosed me in her limbs as well, holding me tightly in place with her arms and legs around me as I pumped in and out of her. Now it was time for the carnal passion that would punctuate tonight's lovemaking. As we made out and held each other tightly, I railed Abby hard and fast, thrusting deep into her twat over and over again, making my balls slap against her taint as I fucked her with unbridled lust.

Our sweat began to mingle together, and the scent of sex filled the room, along with the sound of passionate moans and the creaking mattress. At long last, Abby came. Hard. Her soaking pussy tightened like a vice around my plunging cock as her ankles practically crushed my waist and her nails sank deep into my back, almost cutting my flesh. I never before heard a girl moan, or scream, actually, in one-on-one intercourse like Abby did as she enjoyed her orgasm that came after a buildup that had begun no later than lunch time today. I continued to nail her hard through her orgasm until I was ready to go myself, just as her climax subsided.

Abby insisted I cum inside her, but hearing that request from a girl with a history of some questionable choices, I thought it better to pull out and cum on her instead. Without a word, I did just that, freeing myself from Abby's cage of limbs and pulling out of that awesome cunt to get to my knees and jerk off until cum was launching out of my dick and splattering all over the pretty girl's chest and stomach. I, too, had a pretty incredible orgasm to finalize this amazing day, as evidenced by the numerous spurts of semen that now covered Abby's boobs.

Abby smiled like a fool the whole time as what seemed like endless spurts of cum shot from my cock and coated my dear friend. By the time I was done, I was completely spent. I sat down on the bed, catching my breath as Abby, cum steaming on and between her boobs, caught hers as well, both of us unable to contain our happiness following a perfect night.

With what little energy I had left, I grabbed a cloth to clean Abby up with and then lay down next to her in the bed, where she remained on her back. The sweat on both of us was cooling us off, so I pulled the blanket up over us and held Abby close to me and prepared to fall asleep. We shared on more kiss before I let Abby drift off, all the while as my mind ran with excitement at what seemed to be the next chapter of my life, one for which I had waited a long, long time.

The rest of that weekend was incredible. We had sex three more times over the course of two days, and each session came complete with the emotion and connection, along with a touch of carnality, that had been displayed Friday night. With work looming Monday morning, we capped the weekend off with the final session Sunday night, which finished with Abby's asking for a facial. Nothing made me happier than blasting off on that beautiful face. Seeing my cum streaming down her cheeks and around her gorgeous lips was the perfect way to bring the best weekend of my life to a close.

Monday was a new day, and suddenly it wasn't long until the past weekend felt like it actually had been only a dream. I don't know what changed during work that day, but when Abby came over that evening, it was just to grab her bags and tell me she decided it was better for her to stay with her dad. She hugged me, but that was as far as I was getting that night with the girl I had banged four times the previous weekend.

In the coming days, the best I could get out of Abby was that she just wanted to be alone for a while. I got it: she had been hurt by boys a lot, just like my experience with girls, and she wanted time to recover for now. However, I was still as devastated as ever, especially since she let me so close to her before changing her mind. Instead of finally falling in love with the girl of my dreams, I was trying to resist bitter thoughts of how I couldn't let Abby keep getting away with breaking my heart, which she had done three times now. She truly was a sweet girl, in my mind, but something had to give.

Of course, as always, I was sure this wasn't the end between Abby and me. There would surely be another opportunity. Whether it would be an opportunity to give her one more chance or to make her finally pay will just have to wait to be decided.

dpingjessie
dpingjessie
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AnonymousAnonymousalmost 7 years ago
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Nice point lol. I do feel like Abby is the girl the main character always really liked when it came down to it though and Jessie was more infatuation. Also, to be fair, most guys feel that way about more than one girl throughout life. Seem like some time passed between the two. I thought this was a good story and I liked how it showed a little more depth to the main character

Xzy89c1Xzy89c1almost 7 years ago
I thought jessie was girlf of your dreams

Or did she lose that status when she gang banged a sports team?

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