Scott's Adventures

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Scott recalls the first time he crossed the line at work.
3.6k words
4.41
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2

Part 1 of the 2 part series

Updated 10/29/2022
Created 04/20/2007
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My name is Scott and I was a relatively late bloomer when it came to having much success with girls. Although I was part of the popular crowd in high school, I was a bit on the shy side with the opposite sex. As a result I spent most of my high school being the only virgin amongst my circle of friends.

It wasn't until my senior year at a pre-graduation party that I even came close to getting any pussy. It was common knowledge that I was still a virgin and at the party one of the, shall I say looser girls gave me what I called a sympathy blowjob. That didn't bother me because when someone is sucking your dick you're really not too concerned about why.

I probably could have convinced her to give me a sympathy fuck but she passed out not long after blowing me. I know what some of you are thinking and yes the thought did cross my mind to take advantage of her, but I'm not that kind of guy. Besides, I wanted my first time to be with an active participant who knew what she was doing.

I finally did lose my virginity in my freshman year of college and it was better than anything I had ever imagined. I had jacked-off hundreds of times but after that first taste of pussy I nearly lost my fucking mind. I instantly realized that masturbating was like eating a fast food burger and good pussy was like dining on filet mignon. They both satisfy a need but there is really no comparison between the two.

I'm convinced that my grades during the first two years of college suffered because I spent so much time trying to get laid and completely neglected my classes. At the time I had pussy on the brain night and day and I was devoted to getting as much pussy as I possibly could. Hot or not, Black, White, Hispanic, Asian, from size 2 to size 20 and everything in between, it didn't matter. I fucked anyone and everyone willing to give up the pussy. Fortunately for me I was able to get a lot of practice because a lot of college girls like to fuck as much as I do.

I discovered there were three key ingredients to get a girl to sleep with you: confidence, decent looks, and show them attention. After I fucked my first college girl the shy Scott from high school no longer existed. She was incredibly hot and fucking her was the greatest ego boost of my life. Confidence has not been from the moment she let me cum on her face and every since then I've lived by the rule that if I could get her then I can get any girl.

As for looks I'm not the hottest guy in the world but I can hold my own. I've played sports all my life and have stayed in shape by working out several times a week. I'm 6-foot tall roughly 200lbs with a fairly flat stomach which is the key to at least looking like you're in shape.

The most important thing guys need to do to get laid is to show the ladies some attention. Doesn't have to be complicated, it's the simple things that matter. Complimenting them on something other than their tits and ass, having an intelligent conversation with them (even better if you can be funny or witty while doing it), and most of all paying attention to what they are saying by being a great listener.

Combine these three things together and most guys will get more than their share of pussy. Hell, any two of the three will probably get you laid more than you're use to. But I've always wanted to take it to another level. Getting a girl to fuck me is only step one. The key to getting a lot of pussy is getting the girl to want to fuck you again and again.

The only way to do that is to be an unselfish lover. You have to take your time and do whatever it takes to make sure your girl cums. Whether it's tons of foreplay, eating her pussy, or whatever. Just remember you're going to get yours, you just make sure she gets hers and trust me, she'll be more than willing to come back for another piece of your dick. Women love good dick as much as guys love good pussy and good dick is harder to find. So once she has it, she'll not want to let it go.

By my junior year I had been with about twenty different, all multiple times, but not one was a serious girlfriend. That finally changed and I owe a lot to her because she was a lifesaver when it came to helping me graduate. My last two years of college I didn't fuck anyone but her and by eliminating the constant pursuit of new pussy I was able to focus on my classes. Fortunately I was also able to fine tune my skills as a lover because we fucked a helluva lot those last two years of college.

After graduating we broke up amicably. She found a job back home and I continued my education by going to law school. My love of pussy had to take a back seat during my first year of law school. Anyone who's been can tell you that the first year of law school is pure hell and it literally consumes all of your time.

As luck would have it, I sort of just stumbled upon having a fuck buddy/study partner relationship with one of my fellow students. She wasn't the best looking girl I'd ever been with but we got along very well and she was a great fuck. Neither one of us was in a real relationship and really didn't want one so we figured why not. Throughout law school, it actually worked out great. We haven't fucked since the night we celebrated passing the bar, but to this day she's still one of my best friends.

My first job as an attorney was with a company that owned a chain of convenience stores. I was the Deputy General Counsel for the corporate office. A great title but a shit job. I worked a boatload of fucking hours for relatively little pay. Somehow I managed to stay there nearly 2 years before moving on and while most of that time felt like a jail sentence, the best part of those 2 years can be summed up in one word ... Lisa!

She was 21 and already a single mother of two little kids with different baby daddies who in her own words were both trifling. She had the prettiest golden brown complexion but I wouldn't necessarily call her pretty. She had more of that cute girl next door look to her, but she could still light up a room with her smile. Most days she wore her hair in a ponytail that extended just below her shoulders. Her breasts were virtually non-existent but she had an ass that more than made up for her shortcoming in tits. Round, firm and definitely a site to behold in every outfit she wore. She was 5'5" and weighed no more than 120 lbs. Overall, a very nice package.

When we first met I was strictly professional and didn't pay much attention to her. I was assigned to interview her as part of an investigation of her store where a large amount of money was mysteriously missing. Lisa was the assistant store manager who reported the discrepancy but was scared shitless we would implicate her in taking the money. It turned out that the store manager was embezzling the money and Lisa was completely exonerated.

After the scandal we rewarded Lisa by promoting her to store manager. She was the youngest manager in the company and one of the few black managers, so I kind of took her under my wing and did whatever I could to ensure she succeeded. At the time I was 26, one of the few black executives, and by far the youngest and least uptight person in the corporate office. Therefore I jumped at any opportunity to get out of the office and visit staff in the field.

Lisa's store was very convenient to the corporate office so I quickly became a regular visitor to her store. Although we were pretty much from different worlds we formed a bond and our once strictly professional relationship had definitely turned a lot less formal.

I had been around more than enough women to know when a girl was into me and after a couple of months, Lisa was definitely into me. I knew that if I wanted it wouldn't take much effort for me to fuck her. But I was new to the corporate world and determined not to ruin my career by crossing the line with her. Plus I was actually enjoying our platonic friendship and at the time I was getting my fair share of pussy elsewhere; so I thought it would be easy to resist the temptation of putting a move on Lisa.

One day that would all change when a routine phone call to her store set things in motion that would forever change our relationship. I called her to have her bring some paperwork to the corporate office and as soon as we got on the phone I could tell that something was bothering her. She was reluctant to talk about it but being the concerned gentleman that I am I asked her stop by my office when she got to the corporate office.

When she got to my office, I pressed the issued of what was on her mind. She hesitated at first but then admitted she was having problems with her baby's daddy. I closed my door for privacy and then she completely spilled her guts. The more I listened the more I understood that the guy was a total dick who rarely paid child support, couldn't hold a steady job, and generally treated her like shit.

"Lisa, why do you keep going back to this guy who doesn't sound like he's good for anything?" I asked her with a bit to much of a judgmental tone.

"Well he used to be good for one thing." She responded. "But even that's been bad lately."

"What's that?" I asked without really thinking.

She hesitated for a second before saying, "you know... sex. He use to fuck me like he was the shit, but the last few times he's done his deed and left me high and dry."

"Damn! Talk about adding insult to injury." I said.

"What do you mean?" She said as she looked at me curiously.

Now it was my turn to hesitate. I knew we were crossing the line and treading on dangerous waters. Do I now take the high road and backtrack or do I be myself and treat her like a real friend. I decided on the latter ... "Well, I was just thinking that if he's going to be such a dick, the least he can do is fuck you right."

She momentarily looked genuinely shocked at my bluntness but then smiled and responded, "I know I was thinking the same thing. That no good fucker." She laughed. "That use to be the one thing I could count on from him."

"He's taking you for granted in every way, Lisa. You need to kick his ass to the curb and demand he pay you regular child support. Then find a guy that will appreciate you and treat you the way you deserve."

"I know what I should do, but that's easier said then done. And nice guys aren't exactly beating down the door to be with someone who works in a convenience store and already has two kids."

"Don't give me that shit Lisa. I can help you get a court order for child support and there are plenty of guys that would be lucky to get with you."

"You'd do that for me?" She asked.

"Just say the word. I meant it when I told you I was here to help you any way I could."

"And you really think a nice guy would want to be with me?" She asked skeptically.

"Are you kiddin' me? You know what your problem is? You focus way too much on the negative. Just think of all you have going for you."

"Like what?" She again asked skeptically.

"Well, first of all you're not just a convenience store worker. You're the youngest store manager of a pretty large chain of convenience stores. You're honest ... funny... smart... and very easy to get along with. And not to mention, very good looking."

Hearing so many compliments got to her and brought tears to her eyes. "You're the only guy that makes me feel good about myself." She managed to say as a tear fell down her face.

"You have a lot to offer and don't you ever let a guy or anyone else take that away from you." I reassured her.

I then made the mistake of moving beside her to my office couch and giving her a hug. As soon as we touched you could feel the electricity between us. We looked at each other with longing eyes and as if we were moving in slow motion our lips came together. Within seconds we were engaged in a passionate kiss that seemed to last an eternity.

Startled by a knock on my door. We broke off our kiss and tried to regain our senses. I opened the door and it was my admin assistant asking me if there was anything else I need before she left for the day.

When I turned my attention back to Lisa, I tried to diffuse the situation and take accountability for my actions. "Oh my god Lisa I am so sorry. I don't know what came over me."

"Why the fuck are you apologizing. You didn't do anything I didn't want." She replied.

"That's not the point. We can't do this. I feel like I'm taking advantage of you."

"You can't take advantage of a willing participant. I'm a big girl. I know what I'm doing. I know what I want and I want you! And after the way you just kissed me, I know you want me too." She said.

"You got me there. I'd have to be an idiot not to, but I'm executive of this company and technically your boss."

"Fuck that Scott! Right now you ain't nothing but a man with a hard dick." She said with growing confidence. "And I'm just a girl with a wet pussy who wants to get fucked right here, right now."

At that point all resistance completely evaporated and the only thing on my mind was fucking the shit out of her.

The suddenness of my move in to kiss her shocked both of us but within seconds our tongues were deep inside the others mouth. I pulled her on top of me and her hands busily fumbled with my pants trying to free my hard dick. She soon found her prize and began stroking me up and down as my hands were squeezing and caressing her ass while we continued kissing.

I frantically took her shirt off, expertly removed her bra and started kissing my way down her neck and body. Although her tits weren't that big, she had the longest nipples I'd ever seen and based on her reaction from the moment my tongue made first contact, they were incredibly sensitive.

I alternated between licking, kissing, sucking and biting each nipple and could tell she was in fucking heaven. She was moaning ever so quietly, closed her eyes, tilted her head backwards and completely lost focus of everything, including stroking my dick. I didn't mind because I was so caught up in what I was doing to her and loving her reaction. At that moment I was determined to fuck her like she'd never been fucked before.

I could have worked on her tits forever and she seemed like she could probably cum just from my playing with her nipples but I was on a mission and the ultimate destination was her hot pussy. I went back to kissing her lips as she stood up to undo her pants and wiggle out of her pants and underwear. As soon as she was naked I wasted no time in sticking one and then two fingers in her wet pussy and gently massaged her clit with my thumb. In just a couple of minutes she had her well deserved orgasm that she had been craving for so long.

As she was coming down from her orgasmic high, I took the opportunity to completely free my throbbing dick and dropped my own pants. Getting her first clear view of me in all my glory I could tell she was impressed by the seven inches of manhood starring directly at her.

"Turn around and bend over the couch." I ordered.

Without a word, she did as instructed, turned her head around to look at me as she spread her ass checks and opened up her pussy inviting me in. Her pussy was literally dripping wet and I remember saying to myself, "god damn that's fucking hot."

I grabbed her ass to massage each cheek as I lined up my dick to her hole. As tempting as it was to go in full force and fuck her silly, I decided to prolong the anticipation with a little verbal and physical teasing.

I put the head of my dick inside her and held it there for a several seconds. Her pussy was tight but incredibly wet and her lips easily engulfed my head. I held her ass at bay with my hands as she tried to force me further in by backing up on my dick. After about a minute or two of our little tug of war I started fucking her with mini thrusts just using my head to go in and out her.

"Oh god, Scott that feels good but please give me all the dick. I can't wait any longer. I need to get fucked hard." She pleaded.

"I don't know Lisa. That pussy is so tight I don't know if you can handle the full dick." I teased.

"C'mon Scott! I can handle it. Give me that dick. Please, please give it to me." She begged.

"Ok since you insist." I relented. I removed my hands from her ass and her backward motion caused her pussy to engulf all seven inches.

We quickly developed a steady rhythm of fucking. I grabbed her hips and gradually increased the pace of each thrust. The slapping of our bodies colliding got louder and louder as I began pounding her sweet little pussy.

"Is this what you've been waiting for?" I asked as I continued the onslaught.

"Oh yes that's it. Fuck me Scott! Fuck me." She panted.

Hearing those words have always been an incredible turn on for me and this time was no exception. I decided to take our fucking to a new level. I placed one hand on her shoulder for leverage and support, pulled her ponytail with my other hand, and fucked her like I was drilling for oil.

"Oh god, oh shit! Oh god, oh shit! Oh god, oh shit" she repeated as our fucking went on and on.

My breathing and heartbeat had increased to the point that I would not have been able to speak even if I wanted. All you heard from me were inaudible grunts with each rapid thrust deep inside her fabulous pussy.

I knew the moment of truth was nearing and I prayed that I would be able to keep it up just long enough to give her another orgasm. Luckily my hard work was rewarded when she let out one incredibly long "ohhhhhhhh shiiiitttttttttt!" as her body trembled and her pussy convulsed. She experienced what was without a doubt one helluva powerful orgasm.

With her pussy having spasms on my dick I knew that my time had come as well. Fucking her with all the passion and energy I could muster, I finally reached the pentacle of sexual bliss as my dick exploded deep inside her. The intensity of my own orgasm caused me to go weak in the knees and collapse on top of her as we both fell onto the couch.

Exhausted, sweaty, and completely satisfied, it was several minutes before either of us spoke.

"Do you think anyone heard us?" She asked, breaking the silence.

"I don't think so. It shouldn't be anyone else here. But I don't give a fuck if they did, because that shit was worth it." I confessed.

"I'll take that as a compliment." She said with a smile on her face. "I can't believe we just did that. It's not how I envisioned it but I have to admit, it was even better than I had imagined."

"I aim to please girl, but that was just the tip of the iceberg." I said with a touch of cockiness. "Next time it'll be even better."

"So there's going to be a next time?" She responded with an eager tone.

"Without a doubt! Besides, once you cross the line makes no sense in going backwards." I reasoned.

"I can't imagine it getting much better. But I am damn sure willing to find out."

Epilogue:

I hope you enjoyed the story. Lisa and I hooked up many more times over the next year and a half so I have many more stories I could tell. To this day I still love sex as much as I did 20 years ago when I had my first taste of pussy. Please vote and let me know if you want to hear any more about my adventures over the past 20 years.

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AnonymousAnonymousalmost 17 years ago
You did it again!!

Hi Womenlover

Just read the fic and totally loved it..Definitely had an effect on me!

Can't wait to read some more of your stories.

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