tagAnalThe Associate

The Associate


We were all young associates in a major international law firm. We worked in the Houston office of the huge firm. We were all in our early to middle 20s and single. We worked like dogs and were highly paid. We officially were supposed to bill 40 hours of our time each week to clients. However, it took 50 or 55 hours of work to bill 40 hours a week and 40 hours a week was the bare minimum. You really needed 50 to 60 billable hours a week to advance. It was a stressful life.

I hung out with friends at the firm who were around my age. We all worked like crazy, but had fun after hours drinking and finding entertaining things to do. Most of us would go on casual dates, but the random people we dated did not become part of the group.

Our core group was about 5 guys, one girl and one guy's serious girlfriend. Some part of the group would do something most every night. On weekends, most everyone would join.

The girl in the group was like Elaine on Seinfeld. Everyone liked her, but nobody dated her. She was funny and one of the guys. She could hold her own with the guys, drink heavily and could tell dirty jokes as well as any of the guys.

Her name was Karen Naboob although she would answer to any number of nicknames including our favorite, Nabs. She did not appreciate the nickname, Boobs.

Nabs was 25 years old and was cute. She came from a Lebanese American family and looked the part . She had thick black hair, dark eyes and was only about 5 feet tall. She had nice round breasts on her very short frame, but she did nothing to show them off. She had a beautiful smile and was laughing most of the time.

Karen came from a wealthy family and always dressed very nicely and conservatively. She was a brilliant lawyer from one of the top law schools in the country. We had never seen her on a date, but she did not seem to care. Her family was from Lebanon originally, but they had been in America for generations and she was 100% a Texan.

I had been hanging out with this same group for a couple of years. I was dating some attractive women, but I avoided any type of commitment. I liked to take out my sailboat for cruises most weekends when I wasn't working.

I had a great, 40 foot sailboat, but the problem was that I could not safely sail it alone. I needed at least one person to come with me to help. Consequently, I was always looking for someone to go sailing. All of my buddies liked to go, but most of the time it was a full day commitment and It was hard to line up a partner because we all had to work at least part of each weekend.

Nabs liked to go and she would frequently go with me. We spent a lot of time together sailing in the gulf and drinking beer. We had a lot of fun, but I can honestly say that I did not have one romantic thought about Nabs for years. She was a friend and coworker and nothing else.

She was little, cute and funny, but I was attracted to beautiful, busty, tall women. I was also attracted to bimbos who dressed in sexy clothes. My friends made fun of the low IQ required of any of the girls I took out.

Nabs just never even came up on my radar screen. I also had no thought that she would be even slightly interested in me except as a friend.

One Sunday, Nabs and I took the boat out for a long sail. The weather was perfect and the wind was good, so we sailed for a long time. We also drank a ton of beer while we enjoyed the day.

Nabs was wearing a white t-shirt and some shorts. I have no idea what came over me. Maybe, it was the great day we had just had or maybe it was the beer, but while Nabs was helping me below deck back at the dock, I kissed her.

I gave her a passionate kiss with no warning. As I stuck my tongue in her mouth, I was thinking that she was going to get pissed off and hit me any second now. Instead, she immediately stuck her tongue in my mouth. The kiss was surprisingly hot.

Next, we leaned back into some spare sails that had not yet been stowed and I took another chance by reaching up slowly and squeezing one of her boobs. I was sure she was going to shut this down, but I did it anyway.

To my surprise, she didn't tell me no and did nothing to stop me from fondling her boob. She just kept sticking her tongue in my mouth. I was pleasantly surprised by the hot kiss and the large round boob in my hand.

Nabs broke off the kiss and I was sure this was going to be the end of our little fling. But, instead, she apologetically told me that she left her birth control at home and that I should follow her home.

I managed to say, "Sure, that would be great!"

However, I was thinking, "Holy shit! Nabs wants to fuck! I laid down a bunt with little hope it could work and now the third base coach was waving me in!"

I set a new record in putting up my gear. Neither Karen nor I said another word about the kiss or fucking or me coming to her house until we were getting in our cars. I figured that she would sober up and change her mind, but as we were leaving, she said, "Are you coming to my house?"

I was thanking my lucky stars as I said, "Sure, I will see you there."

During the hour long drive home, I thought that Karen would get cold feet or otherwise come to her senses and that we would have a laugh about her tricking me into thinking we were going to have sex. By the time I arrived at her house, I was completely convinced that no sex would occur. I even doubted that I had heard her right.

As I arrived at Karen's house, she met me at the door. It was just like always, "Hey, Nabs!"

She smiled big and said, "Hi, come in and have a seat. I will be right with you."

I was sitting on the couch by myself for a few minutes convinced that the sex was a dead issue and wondering where Nabs had gone.

About that time, Karen came out of the back of the house wearing a long white nightgown. It was not a sexy or nasty nightgown, but it was a nightgown. I could tell that she was not wearing a bra under the gown. The outline of her round breasts and nipples were visible through the gown. Her nipples were hard.

I thought she would join me on the couch for some more kissing, but instead she grabbed my hand and led my back to her bedroom. The bedroom was dark and Karen did nothing to turn on any of the lights. I thought to myself that she must be shy or probably inexperienced.

When we arrived in her dark bedroom, Karen gently began to remove my clothing starting with my shoes and pants. When I was naked, she quickly slipped out of her gown and lay down on her bed on her back.

Her tits looked nice and round. They bounced as she got situated. She had thick black hair around her pussy.

I started to go down on her to warm her up, but she stopped me very abruptly. She also stopped an effort to put my cock in her face. I was a little surprised that she seemed to have no interest in oral sex. It did not fit with her open, easy attitude about life.

Instead of any kind of foreplay, she spread her legs and pulled me down on top of her. We hadn't even kissed since we arrived at her house. My buddy Nabs just wanted to be fucked.

I got over her in the missionary position when I felt her hand wrap around my hard, thick cock. Her touch was gentle and nice and she directed my hard cock into her pussy. She was soaking wet and my cock quickly slipped inside. My cock is pretty big and thick and I have a hard time entering many women, but her pussy just devoured my cock. Her pussy was both extremely wet and tight.

Words are not going to do justice to describe what I experienced. Nabs enveloped my entire body with hers as I fucked her. Her pussy felt soft and inviting. Her arms and legs seemed to surround me. I felt like she put every bit of effort and concentration possible into giving me pleasure. It was awesome!

I fucked her and fucked her and fucked her. She took my cock with a low groaning, moaning sound. I absolutely loved it! We fucked for a long time and then I exploded into her soft pussy. I again tried to go down on her, but she told me that she had already had an orgasm.

I had never been fucked like that. I am not sure what she did with her body, but it was different from any other girl I had known and the feeling was tremendous.

We did not have any romantic pillow talk afterward. We lay in bed and I felt her big round boobs and gave her shit for hiding them so well every day. She laughed and seemed to enjoy the attention her chest was getting.

Eventually, I went home and wondered what just hit me. I had been dating a tall, sexy fashion model, but sex with little Nabs was twice as much fun as sex with the model.

I woke up the next morning early and was horny for Nabs. I could not think about anything else.

She usually slept late and then worked late at the office. I took a chance and called her early in the morning long before she would normally go to work.

I woke her up and asked if I could come by and see her.

Sounding like she was coming out of a coma, she mumbled, "What time is it?"

"About 6:30," I replied.

"You know I don't get up this early and you are calling me to see if you can come visit?" Nabs asked in a groggy voice.

"Well, yeah. I wanted to see you before work." I said lamely.

Nabs then said without any hint of humor, "What do you want to do when you get here?"

I had not expected that question, so I stumbled around saying something like, "Oh, I was just sort of thinking . . . after yesterday . . . well I was hoping . . . ."

Nabs laughed at my smooth reply and said, "I can't believe how horny you are. Come on over. I will leave the back door open for you."

Nabs met me in her bedroom in a t-shirt that showed off her nice cleavage and her panties. We immediately began to pull off our clothes and fuck in that magical missionary position again.

The morning fuck was as awesome as the night before.

This began a month of frequent, incredible fucking. We never went on a date(or even thought about it). We did not let anyone know we were fucking. It would have been awkward at work and awkward with our friends. We didn't really discuss these things, we just both did them.

Also, there was not one romantic word exchanged between us. It would have embarrassed both of us if we said something loving. So, we just fucked.

I tend to be oblivious about the feelings of women. It is not that I don't care, I just don't always pick up on social cues. My brother used to have to tell me when women wanted to date me. I honestly didn't notice.

Anyway, I did notice a few cool changes in my buddy Karen. She never said no to sex with me. This went even beyond the norm because she would assume that if I kissed her or fondled one of her big round boobs or grabbed her little ass that I wanted to cum inside her right then.

For instance, if I grabbed one of her boobs at work, she would start trying to figure out way to get us immediately to her house to fuck. It happened every time. I felt flattered every time.

The other change was that I started to see cleavage. I had known Karen for several years and I had never seen her show any cleavage whatsoever. Even in evening gowns she did not show any cleavage. I don't think her swim suits showed any of her boobs.

After we started fucking and she figured out that I really liked her nice round tits, every top she wore outside of work showed some cleavage. Some showed a lot of cleavage. Seeing the tops of her round tits and her sexy cleavage made me horny every time. This led to a lot of fondling of her boobs which, as I mentioned, led to immediate fucking.

By the way she never stopped me when I wanted to fondle her boobs. She seemed to like being groped even if we were almost in public or somewhere that we could be seen or caught.

During all of this time, we never had oral sex of any kind. I love to give and receive oral sex. Karen avoided it completely. I became convinced that she had some sort of hang-up about it. However, the fucking was so good, I did not really care.

Nabs refusal to give or receive oral did not seem to fit with her personality or her giving nature as a sex partner. It had me bewildered, but she would not budge. We never really talked about it, but she would just refuse if I tried to start any oral sex either way.

After about a month of fucking my friend, Karen, I asked her to roll over as we got ready to fuck. I loved her version of the missionary position, but I thought a little doggy style might be fun.

At first, she said no. But, I said, "Come on, Nabs. It will be fun."

She finally said okay and rolled over to show me her little ass in the doggy position. She looked so small on her knees with her ass up. My cock was hard as a rock.

I entered her from behind and fucked her hard. I liked the idea of fucking a brilliant lawyer from behind in such a submissive position. It was fun, but was not as exceptional as our normal fucking sessions. She seemed to like it too.

After we were finished, I whispered to her, "Now that wasn't so bad, was it?"

Nabs giggled and said, "No, that was fine. I thought you wanted to do something else and I was afraid you were too big for me."

After a second or two for that to sink in, I said, "Hold it. When you rolled over you were saying it was okay to have anal sex with you?"

She looked amazed that I did not understand that in the first place and replied, "I had not thought of it that way, but yes I was ready for you to take me anally."

She laughed as I desperately asked for a rain check. I was pretty sure that my friend was going to let me fuck her in the ass!

I was so excited about the prospect of butt fucking Karen I was afraid that I would say the wrong thing and she would change her mind about taking my dick in her ass. I ended up stuttering and stammering until she started laughing at me trying so hard to arrange for another time to have anal sex.

I had only had anal sex once and that was with a whore on a sailing trip to South America. I wore two condoms and enjoyed it as sort of a power trip. Anal sex with a conservative, first class lawyer was obviously completely different and much more exciting.

We returned to our routine of slipping off and fucking until one weekend when Karen asked me to help her set up for a party. I had not yet tried anal sex with her even though I now knew she would let me fuck her in the ass. I was looking for a good time to try it on her. Truthfully, I probably needed to be drunk to try it with my friend even though she seemed willing. I did not want her to think I was a pervert or something.

Karen was going to have a party at the home of her parents. She needed some help moving furniture to get ready for the party and she asked me to help.

When I arrived at the house, it was just the two of us. I started moving furniture when I became distracted by the nice cleavage Nabs was showing. I knew the low cut blouses and sweaters could not be a coincidence.

I came up behind Karen and grabbed both of her big breasts. She moaned slightly and let me feel her up.

"I didn't plan on this," she moaned. "I don't have my birth control with me."

I was thinking that I would just have to fuck her later when she grabbed my hand and led me to her parents' bedroom.

She told me to get undressed and lay on the bed. Of course, I followed instructions. I was on my back, naked with my already hard cock sticking straight up. Then, to my great surprise, Karen crawled up on the bed still fully clothed and gently cupped my balls. I was still trying to figure out what was going on when Karen engulfed my entire cock with her mouth.

I have never been more surprised. First, I thought she didn't like oral sex. Second, no girl had ever come anywhere near taking all of my cock in her mouth. I could not believe how good it felt.

I could not resist raising up a little and looking. I looked down at my crotch and saw Karen's lips at the base of my cock with my pubic hair in her face. She looked up as she bobbed slowly on my dick and our eyes met with most of my dick down her throat.

It was awesome! My cock is pretty long and thick, but this little girl had it down her throat. It felt as good as her pussy. Nothing but her mouth ever touched the shaft of my cock. She kept one hand gently on my balls and was sucking up and down on the base and lower half of my dick.

I should have been happy with the deep throat blow job, but I even went further and started thrusting my cock into her mouth. I thought sure she would gag, but she just took it. I kept thrusting up harder and harder and she just took it.

Before too long, the excitement of getting deep throated by a girl who I thought did not suck cock was too much for me.

I said, "Karen, I am cumming!"

I warned her because I still did not know what she thought about oral sex. But, instead of coming off my cock, she went all the way to the base of my cock and sucked for all she was worth. I shot stream after stream of cum down her throat with a loud groan.

She kept my dick in her mouth until she was sure I was finished. Then, she came up and hugged me with her head on my chest. Her face was red or maybe a little blue. She was huffing and puffing trying to catch her breath. Her eyes were watering and she had saliva or cum on her face. I had never seen a woman so winded and exhausted from any kind of sex.

I was amazed by the way she put everything she had into my sexual satisfaction. I had never experienced anything like it. It literally took her about five minutes to catch her breath and return to a normal color.

I told her over and over that she was amazing. Then, curiosity got the best of me and I said, "Clearly, you have done this before, Nabs. Why did you refuse to have oral sex before now?"

She got a little embarrassed and said, "Every time I do this to a guy, it is all he ever wants to do."

As I lay there completely spent from her blow job, I thought, "No shit!"

However, I said, "It was wonderful and the best I have ever had, but I would never be like that."

Nabs just quietly said, "We'll see. I hope that is right."

I drove home that day thinking that the girl had unbelievable talent sexually. I had been with sexy girls, but that was mostly based on looks, big boobs or being promiscuous. Nabs was not a classic babe but she was awesome at sucking and fucking. I guess it makes sense that some people will be more talented than others at having sex, but I had never experienced anything close to the things that Nabs could do. Given her experience with every guy she was with wanting nothing except her mouth, I guessed that Nabs knew she was great at having sex.

As I thought about my cute little friend being a great cocksucker, I decided that it made sense. Some guys have natural ability to hit a baseball or throw a football and a few of them also work hard at getting even better. I had stumbled on to the Babe Ruth of cocksuckers. She also had the ability to concentrate completely on the task and clearly had the desire to give pleasure and improve her skills.

I wondered how many cocks had been down her throat.

The next morning was a work day. I woke up with a boner wanting to go to Nab's house for a blowjob. However, I managed to resist. I did not want to be like all of the other guys who only wanted her to suck cock.

I tried to concentrate on work, but I kept thinking about looking into Karen's dark eyes while my cock was embedded in her throat.

At 11:30, I gave in and called her.

"Will you join me for lunch, Karen?" I asked.

"I am going for Tex-Mex with a couple of the guys, but you should come too."

"Why don't you ride with me? Just the two of us." I suggested. "I have an idea that might be a lot of fun after lunch."

Nabs innocently asked, "What is your idea? I don't have too much extra time today."

"Oh, I don't know. I was thinking we might find a spot to mess around."

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