My name is Pete. I’ve worked for the last fifteen years at a large financial institution based in Silicon Valley and have managed to work my way up to a good position as an assistant manager. I’m not terribly interested in moving higher than that simply because of the headaches I’ve seen my boss get from climbing higher in the corporation. My boss’s name is Nicole.
When I started with the company, she was one position lower than I am now. Back then, there were only five people in the whole department. She currently manages over forty people and doesn’t get paid for the overtime she has to put in for all the reviews she has to write. She’s good at her current job, but she had to take a pay hit at first to be placed in a salaried position. Over the years, we’ve become good friends, partly because we’re the only ones who have remained in the department this whole time. Before you get any ideas, let me just tell you that Nicole is only a bit younger than my mom, and quite frankly, I kind of think of her as a surrogate mother.
One of the perks I’ve enjoyed about this job is that most of the people involved in this business are women, especially in my department. There were about three years when I was the only man working here, and I really loved my job for those three years. The ages of the women working in my department have spanned from about 16 to roughly 60 years. The older women treated me like a son, the younger ones like a little brother, and the youngest ones like a … well, like a friend that they had just noticed was a guy. I tended to flirt a lot with the departmental cuties.
One of the rules I’ve always had was that I would never get into a romantic relationship with one of my co-workers. The last thing I wanted was to have my personal relationship break-up and be forced to work with my ex while working through my feelings. That just would be too much for me to handle. So, although I flirted with some of my co-workers, I never ended up asking any of them out for a date. I still think this was for the best. Okay, I used to ask Nicole to let me take her oldest daughter out. I stopped asking when that little girl of hers wasn’t such a little girl anymore, and I realized that I wasn’t joking anymore either.
You now know how everything stood until a couple of days ago. The company I work for processes the accounts of large retailers as an accountant would, so the retailers don’t need their own accounting departments. My department processes our customers’ deposits before they are sent out to the banks, reconciling their accounts balance and correcting any discrepancies in the day’s receipts.
I guess I should mention that one of my co-workers for the last four years is an attractive young Vietnamese woman named Jennifer. Actually, Jennifer is just her nickname, but I have trouble pronouncing her real name, and we never use it in our department.
Jennifer is twenty-two years old, and when she first started in our department, she was a high school dropout gangbanger. She would wear baggy sweatshirts and jeans, no makeup, and a backward baseball hat every day to work, and just quietly sit at her desk. This was acceptable since we don’t have customer contact, and the dress code is relaxed for us. But I will never forget the day she decided to get rid of that gang look. When I saw this attractive young woman sitting at Jennifer’s desk, doing Jennifer’s work, I went to Nicole.
“Who’s that sitting over there?”
Nicole laughed and said, “That’s Jennifer. Who else would it be?”
That was pretty much how the whole day went. Some guy would come in to start work or stop in to make a photocopy, see this unfamiliar young woman working at Jennifer’s desk, and ask Nicole who it was. It was obvious none of us guys had taken much notice of her before by how much attention she was getting now. None of the women said anything then, but when I talked to some of them recently, and they all noticed as well. The only difference was the women had paid enough attention to her before that they could recognize her. Nicole had a great time that day watching the expression on all the men’s faces one at a time as they found out who it was at that desk.
Jennifer had changed her whole look. She had traded the baggy sweatshirts for skirt suits, the tennis shoes for high heels, the baseball hat for hair combs, and the jeans for pantyhose. I knew Jennifer had long hair but was now showing it off by letting it hang free or in ponytails, instead of putting it up under that baseball hat all the time. It was evident that she had a lovely, petite figure she had been hiding under those baggy clothes. It was like having a new lady in our department.
Since then, I’ve made casual friends with Jennifer. We would talk about business and what was going on in our lives. I found out that she had trouble keeping her relationships going. Quite frankly, I was never impressed with the young men she dated. They were often distant and very unfriendly. I guess they could be described as “exciting” types – always moving from one adventure to the next, and girls were just another adventure. I’ve never understood why young women find these guys exciting, but I have discovered that women usually outgrow that stage. I can’t say the same for the men.
Last week Jennifer’s car broke down. She couldn’t keep it in good repair, and it gave out last Thursday. She was able to have it towed, but she missed that day at work. She managed to get to work on Friday by using the bus and light-rail. The mechanic called later that afternoon, and after Jennifer got off the phone, I asked her how the conversation went.
“Well, it went okay. It’s not going to be expensive to fix it, but it’ll have to be in the shop for a few more days. They expect to have it done by Wednesday,” she explained.
I was happy for her. I knew that she couldn’t afford expensive repairs on her wages. “How are you getting home tonight?” I asked.
“Oh, I’ll just take the light-rail and bus, or something,” she said.
“Why don’t you ask Nicole if she’ll give you a lift?” I suggested. “She’s dropped Brenda off before. She probably won’t mind.”
“Yeah, that sounds like a good idea. I’ll try that.”
That was pretty much it for our conversation at that time. We both went back to work, and I guess she asked Nicole for a lift. About a half-hour before quitting time, Nicole’s husband called, reminding her that he had to go in to work early that night to clean up after a party at the hotel where he worked. She needed to come home soon to take care of the kids. I found out about that because Nicole had to leave immediately to make it, and asked me to take Jennifer home for her.
I had no problem doing this since it wouldn’t be the first time I had given a ride to one of my co-workers. She lived out in the ‘burbs, but I could take her over there without a serious problem. Besides, I felt better knowing she would be safe and not riding the light-rail and bus alone that late at night. After seeing everyone else out of the department, Jennifer and I started for her home. As we sat in the car, I found myself casting a few admiring glances her way. She was wearing a navy-blue skirt that ended about three inches above the knee, showing off a nice pair of legs, a silky white blouse that wasn’t too clingy, and a navy-blue jacket. Her hair was loose behind her, showing off her thick, black locks. I thought Jennifer pretty much hit all the right notes with her outfit.
For most of the trip, our conversation was pretty casual. It seems Jennifer had broken up with her most recent boyfriend just the previous week. I asked her why she had shown him the door, and she replied: “Because he was weird.” I had to bite my tongue because I was thinking that she specialized in weird boyfriends.
“How was he being weird?” I asked as I turned off Broadway onto her side street.
“Well, he wanted to date other girls and bring them back to my place so we could both have sex with him and stuff like that.”
“Ah,” I said, “so he was in it mostly for the sex and the adventure.”
Sounded like her type, I thought. We started to drive up to her apartment at that point.
“Yeah.” She was quiet for some time before she spoke again. “Ya know, I’m feeling really horny right now,” Jennifer said timidly.
Then to my surprise, a bit more plainly, “Would you like to come upstairs and fuck?”
My eyes must have nearly popped out of my sockets. Here was an attractive, exotic, well-dressed young woman asking me to have sex with her, and she wasn’t making any bones about it! It sounded like any number of fantasies I had in my younger days.
I somehow managed to say “What?” without sounding accusing.
“Well, I like you, you’re a nice guy, and I’d really like to get off,” she stated.
I hadn’t misunderstood her. The shock of the situation, as well as trying to keep the car under control, kept me from responding for several seconds. Then my morals got the best of me.
“Um, thanks, but I can’t. I really love my wife, and I wouldn’t want to do anything that might hurt her or my daughter. I do appreciate the invitation, though,” I replied honestly.
“Oh. Okay. You know, that’s one of the things I like about you, you’re so nice and thoughtful.” She continued: “Well, I guess I’ll just have to grease up the ol’ vibrator and masturbate myself into a frenzy.”
I’ll be honest. The way this young woman was talking to me really surprised me. Of course, the way she was talking was also getting me very turned on. I started to get an idea.
“Hmm,” I said to stall until the idea took shape and passed my internal morals committee.
“You know, most men consider it a bit of a … treat … to watch a woman masturbate. Would it bother you if I went with you and was your audience? I’d just be sitting in your room, watching. Nothing else,” I quickly added.
“You want me to put on a show for you?” Jennifer sat there thinking for a few seconds while I kept the motor running.
“Sure,” she said, “That sounds like fun! It would be better than just being by myself!”
With that decided, I parked the car on the street. We quickly got out of the car, and she led me to her second-floor apartment, giggling much of the way.
After closing the door behind me, Jennifer said: “This is going to be SO much fun!”
Then a look came across her face, I guess she had just remembered to act as a hostess and asked: “Would you like anything to drink? Some wine or a soda?”
“I’ll take a Dr. Pepper if you have one,” I said.
“No problem!” she replied, and quickly entered the kitchen. She brought back a glass of soda for me and a full wineglass for herself. She must have taken off her jacket while in the kitchen and left it in there.
“And now,” she said with a flourish, “it’s off to the bedroom! Follow me, sir!”
“Won’t your roommate mind?” I asked.
“She’s not here tonight. She spends all her weekends with her boyfriend. So, it’ll be no problem at all,” she explained. She then motioned me into her room and pointed me toward a chair in the corner opposite her bed.
“If you just take a seat over there, the show will begin shortly,” she said with a grin.
She went to a stereo on her dresser and put on a disk of some boy group, kicked off her high heels, and lay down on her back on the bed. For several minutes she simply listened to the music and drank the wine. I was in no hurry and didn’t want to spoil her concentration, so I just sat in the chair quietly and relaxed.
After several minutes, she gave out a sigh and ground her shoulders into the pillow behind her. “I’ve never done anything like this before,” she said lazily.
“Just do whatever you need to be comfortable. Don’t pay any attention to me,” I said.
She waited for a moment, and then she started to brush her right breast through her blouse. She used the entire length of her hand, held rigidly, to brush over the tip of her breast through the cloth, and then would make circling motions with just her palm, before cupping and squeezing it a little. She then started doing the same to her left breast, massaging her right breast at the same time. After stroking her nipples like this for what seemed like forever, she slowly moved her left hand and started unbuttoning her blouse one button at a time. After the third button, she moved her free hand inside. She began to massage her breasts directly, all the while continuing to unbutton her blouse. By this time, I could finally confirm what I had suspected – Jennifer didn’t wear a bra!
When she had unbuttoned her blouse, she slowly sat up and removed it, letting it fall over the edge of her bed onto the floor and slowly stretching like a cat. Her breasts were not large but were quite firm. They did not flatten out at all when she stretched. The areolas were a little larger than quarters with the nipples standing out like little pencil erasers in the middle. Her skin was a beautiful dark olive with no tan lines. I was entirely caught up in everything by this point. Excepting my wife, I hadn’t seen a woman naked like this in some time. Not bad for a show that had hardly begun. Jennifer then slowly lay back down and started playing with her breasts again, this time alternating the brushing by her palm with tweaking and rolling her nipples between her fingers, still one breast at a time. She started licking her fingertips, rubbing them on her nipples, and then blowing across her breasts. Whenever she did this, her nipples seemed to get just that much more erect from the cooling action of her breath.
This was clearly getting her turned on as she was by now mercilessly massaging her breasts. Her hand was slowly stroking down her stomach and working its way toward her waistband before returning to her breasts for more attention. After doing this several times, she finally lifted her bottom up and unsnapped and unzipped her skirt, quickly pulling it and her panties off and kicking them onto the floor.
Jennifer looked at me, grinned, and asked: “Enjoying the show so far?”
“Definitely,” I replied.
Jennifer lay back down, and now the pace picked. She kept up her pattern of before, massaging her breasts, blowing across her nipples, running her hands across her stomach. Now she added some movements that were really starting to get to me. She was caressing her hips and grabbing her bottom while rocking her hips and then returning to her breasts. Each time her hands went lower, and her legs would part a fraction of an inch, showing me what was below that neatly trimmed little bush of hers.
This was a torment! She finally started gently tickling the inside of her thighs, tracing the inside with a fingertip. At the same time, the other hand had a grip on her breast. Finally settling on her outer labia, she stayed there for just a moment. I’m not sure if she was savoring the feelings in her body, or if she was unsure if she wanted to keep going, or both. She finally spread her lips a bit and slowly moved her finger between them. She then quickly brought her finger up, traced her juices around a nipple, and blew across it. Her hand found its way back to her pussy, and she started fingering herself in earnest, rubbing her hand across her mound before sliding a finger in to rub over her nub for just a second. She did this several times, until she finally pushed her finger all the way inside for a couple of strokes, and then followed it with a second finger. She held them both inside her, slowly twisting them, and then pulled them out before adding the third.
“Oh, God, this feels good!” Jennifer said.
“It looks great from over here,” I replied, just a bit breathless.
I was blown away by all of what I had seen so far. This was actually quite beautiful in a way, positively not obscene. After several minutes of this, she stopped, reached over to her nightstand and pulled a large vibrator and a tube of K-Y out of the drawer.
“Now for the good part,” she said.
The vibrator looked like it was about a foot long and about two inches in diameter, certainly more substantial than any I had ever seen. It was pink, had a head like a real cock, and bumps along the length. I was wondering what a small woman like Jennifer would do with such a hog, when she turned it on and started moving the tip around her nipples, one at a time.
By the look on her face, it was evident she was really enjoying the feelings. Her eyes were closed, and she moaned quietly as she slowly circled her left nipple and then slowly traced the tip through her cleavage to circle her right nipple before brushing the length of the vibrator along the tip of her breast. She stopped, placed it in her cleavage pointing toward her face, and pressed her breasts around it for a bit, just letting it sit there, buzzing away.
She then surprised me by turning the vibrator off. The sudden lack of that buzzing sound almost made me jump. Jennifer then looked around, found the tube of K-Y, and proceeded to rub a small amount of the jelly onto the vibrator. Taking the lubricated plastic phallus in hand, she started to place it between her legs. For several seconds she did nothing, just laid there with the tip placed against her pussy lips. She then began to rub the head against her clit, back and forth several times before returning to her opening.
“Are you ready for this?” she asked.
“Um, don’t hurt yourself for my behalf,” I said with some concern.
“It doesn’t hurt. At least not in a bad way,” she said while still rubbing the tip of the vibrator against her opening. I was sure that this was all she was going to be able to do with that monster dildo, considering her tiny size.
But then she said, “Here it goes!” and reached down with one hand to spread her lips and started to push it slowly up into her vagina!
Once the head was just a bit past the opening, she turned the vibrator back on. The way it made her twitch in the bed and grunt, she must have enjoyed it! She almost sat up as she placed the heel of her hand against the base of the plastic penis to push it entirely up inside her!
I was sitting at the edge of my seat at this point. I was concerned that Jennifer might accidentally hurt herself while trying to show off for me by taking much more than she was built for. Still, I was surprised at how much she stretched to take the vibrator! It looked like she was at her limit and that she couldn’t possibly take any more, but after a few moments, she managed to take the entire length all the way down to the base!
This was certainly more than I had bargained for, and if I had paid a thousand dollars to see this, I would have gotten my money’s worth. For a minute or two, Jennifer just laid there with the vibrator buzzing away inside her, only the very end visible. Then she grabbed the base and started twisting it around and pulling it out slowly. This continued until it was almost all of the way out, and then she pressed it back inside, much faster than before. When it was all the way back inside her, she let out a little gasp and held it there, twisting it around, before pulling it back out again. She finally sat up a bit and propped herself up with a pillow against the headboard so she could change her angle.
Breathing heavily, she looked at me and winked. “Watch this,”
She then started pushing the vibrator back inside with one hand and started rubbing her clit with the other as we both watched. After a few pumps like that, she laid her head back and closed her eyes, just enjoying the sensations she was giving herself. She started to push her hips off the bed to match each push of the vibrator as it slid up into her vagina. The slurping sounds that her pussy made each time she pushed it in were louder than the buzzing and mixed with her scent, were driving me wild! I sat in that chair, back ramrod straight, not believing my luck! No guy I knew had ever seen anything this erotic before!
With each thrust, she moaned with pleasure. She was beginning to lose a bit of control and was thrusting the monster cock into her pussy very hard now. I could see each bump of the vibrator as it rasped against her pussy lips and the head as she pulled it almost all the way out before jamming it back inside to fill her to capacity! Her moans were becoming louder now as she began to climax. I have always loved to watch the expression on a woman’s face as she reaches that moment of sexual release, but I had never witnessed a woman climax so strongly before! It looked like Jennifer was in pain! She was bouncing around on the bed like she was having a seizure before she pushed her hips forward one last time and pushed the vibrator to the hilt inside her while moaning aloud: “Oh GOD!” Her juices flowed out around the vibrator as she squealed one last time before collapsing on the bed, spent.
She was breathing very heavily now and was covered with a sheen of sweat. I saw her turn off the vibrator, but she left it inside her for several minutes, just resting, before sliding it out and placing it on the nightstand. She looked like she had run a marathon race.
I got off my chair, walked over to her, and said: “Great show,” and started for the door. Just before leaving, I looked back, saw Jennifer beginning to go to sleep.
“I doubt I’ll ever see anything else like that again. Sleep well. I’ll see you at work on Monday.”
“Well, I’ll need a lift next Monday and Tuesday,” she reminded me sleepily.
I let myself out, wondering what the next week would be like.
