Its Christmas time again. This story came about as a result of what happened at my employer’s recent (2001) Christmas dinner party. As usual the grand event was scheduled at a local restaurant. And as usual as soon as the dinner concluded, a group of us headed for a bar/nightclub to really celebrate the holiday. This year my husband decided that he had enough fun in the past and bowed out of the grand event. So his leather clad wife went alone to the party. If you’ve read one of my previous stories, I can tend to make things eventful for one of our lucky male employees. This year I wore my sexy knee length black leather pencil skirt. I really love the skirt and is probably the sexiest of the several that I own. I also wore my sexy silk black and white printed blouse with a leather vest. I kept the top two buttons of the blouse open to show my cleavage. Finishing off the outfit was a pair of black mist thigh highs and a new pair of high heel black leather knee high boots. I have to admit I did look pretty good. After finishing my make up and lip gloss off to the party I went. As I expected as soon as I hit the door of the restaurant all eyes were upon me. Especially the men. And it was amazing how many of the guys felt a real need to hug me as if they hadn’t seen me in a long time or how they felt a need to stand next to me and put their arms around me as if I were their date. The evening was still young and I bet I had been rubbed and felt up at least 50 times before dinner. As the cocktail reception was winding down I happened to glance at the doorway and to my surprise standing there was my former boss, Jim. Jim had left the company a little over a year ago for another opportunity. I had worked for him for 3 years and we had a great relationship. To be honest, I sensed a sexual attraction to him while we worked together, but he was a pretty straight guy who had visions of advancement and didn’t want anything like having sex with his assistant to ruin any chance of his progression. I always put him in the category of tall, dark and handsome. I used to have fun in the office with him on days I wore leather. I knew he enjoyed seeing me dressed in a leather skirt or a pair of my leather pants. Many times I could see the bulge in his pants that I created. It must have driven him crazy seeing me dressed so sexy and provocative. We’ve flirted with each other but never had anything come of it. As soon as I saw Jim I immediately walked over to him. I kissed him on the cheek and told him I was so glad to see him. Judging from the smile on his face and the way he was eyeing me up and down, he was glad to see me too. He told me that he had gotten a special invitation from my current boss (who happens to be named Jim too) to attend this years party. He had some business in
town so he decided to drive from Chicago, take care of his business and attend the party. I noticed his wife wasn’t with him and upon inquiring he explained that she decided to spend some time with some old friends this evening and he would meet her later at the hotel. He put his arm around me and told me how glad he was to see me and how good I looked tonight. As we stood and had a drink together he told me he was sort of glad that his wife decided to not to attend so he could spend time with me and catch up on things. As I was finishing my drink, I happened to notice that something was beginning to grow inside his pants. Since he and I were without partners I asked him if he would like to enjoy my company during dinner. While having dinner I noticed that every chance he could get, Jim found a reason to touch me. It started with just a gentle rub or brush of his hand but by mid meal and a few glasses of wine he got braver and placed his hand on my thigh or even brushed against my breasts. Talk about flirting. Well in all honesty his touching began to get me a bit horny and by the end of the meal I began to feel some wetness between my legs. My black silk panties were getting a bit warm. As I said dinner was pretty uneventful with the exception of Jim’s petting and flirting. As usual a group of us decided
to go to a nearby bar to really unwind and celebrate the holiday. Jim had asked if I wanted to leave my car at the restaurant and he
would drive us over to the bar and would bring me back later to pick it up. I wasn’t totally stupid as to why he asked to drive me. On the way over I purposely sat in a position to give Jim a view of my sexy leather booted legs. I also made sure that I hiked my leather skirt enough to give him a good view between my legs. Upon getting out of the car I could tell my little show had an effect on him. Once we were at the bar our group immediately began to loosen up and have some fun. Somehow Jim was able to commandeer me to the bar where he got a couple of bar stools and asked me to sit so we could talk some more and catch up on each other. As we sat and talked his hands began wandering again and it was beginning to get obvious to me that he was really aroused. I looked down at his crotch again and could tell that his manhood was pressing against the cloth of his slacks. I knew I was causing him to have the ultimate boner. Seeing him getting so hard was also getting me quite aroused. He leaned over towards me and whispered in my ear.
He told me how sexy I looked tonight and when he initially saw me at the cocktail party, he felt himself begin to get hard in his pants.
Then, almost to my disbelief, he further admitted that in the time I worked for him how many times he’d get turned on looking at me dressed in my sexy leather skirts. He was so afraid to say or do anything becausehe didn’t want to chance my getting upset or causing him to take stupid risks that could hurt his chances for advancement. He also admitted that several times he’s masturbated thinking about me. Wow, I thought to myself. That took a lot of nerve and courage to admit. But the more he talked about it, the more I wanted to hear. I nearly had an orgasm sitting there and listening to him. All the while and not paying attention to who may be seeing us, Jim moved his hand to my leather covered thigh and began rubbing. Within a short time his hand moved up my skirt and ended up against my wet silk panties. I, in turn moved my hand onto his thigh and then right into his crotch. I couldn’t believe how hard he actually was. I began rubbing and stroking him through his pants. I couldn’t have made him any harder than he actually was. I told him now that he was no longer with the company he didn’t have to worry about risking his career and advancement. He said the only advancement he was interested in at the time was with me. That’s all I had to hear…… The two of us got up from the bar and out the door we went, not caring who may have seen us leave together. We made a “b-line” right for his car. Once inside the car we embraced and began
kissing and making out like two kids on a first date. As I kissed him I began fumbling around with his pants and unzipped them. I placed my hand inside and couldn’t believe how wet and sticky he was from all the precum that oozed from his penis throughout the evening. He was hard. Very very hard. Actually he was so hard that anything other than just stroking him would most likely have made him uncomfortable. I released his penis from his pants and in looking at it I couldn’t believe how dark the tip of it was, most likely from an enormous amount of blood rushing through it. He began to moan about how hard he was and how much he needed to cum. I was
really turned on hearing that and began to stroke him softly and gently so not to hurt him but make him feel good. He moaned that he wanted me to make him cum and how much he needed to unload for me. The more he spoke the more I rubbed him. I placed one hand under his balls while the other hand continued to seductively stroke him to jack him off. “Oooh you are so good,” he kept moaning. I decided to vocalize myself by telling him how hard hewas and how much I wanted to make him cum. The more I spoke the faster he moved his hips in unison with my hand. I began rubbing the sensitive area underneath his penis. Being an expert, I know how good it feels to a man when I rub him in that spot. He was nearly there. As I blurted “cum baby, cum for me, he finally tensed and I began to feel his cum running through the tip of his penis. I moved his penis and my hand down to my skirt where I let his creamy liquid run through my fingers and onto my skirt. “God, that feels so good” he moaned as he unleashed spurts of cum onto me. The more I stroked it the more cum would run out. I loved feeling the pulsation of his dick as he continued to empty himself on me. I couldn’t believe the huge amount of sperm that poured from him. He finally emptied himself and told me how good I was in jacking him off. I kind of jokingly told him that his wife must be depriving him of sex because he was so intense and he seemed to have a rather large amount of cum. He told me that he just had gotten so turned on seeing me and that I was so good at making him cum that I must have milked every drop out of him. Thinking we may be done I began to prepare to get out of the car. Jim took my arm and pulled me to him. He began to kiss me again and started lifting my leather skirt towards my hips. Once the skirt was up he reached under and pulled my panties down. The next thing I knew his face was buried in my crotch and I could feel his tongue enter me. I leaned into the car door and let him enjoy the sweet wet fruit. He was so good at it too. Had I known how good he was at eating pussy I would have never let all that time pass. God he was so good. I pulled his face further into me and had a huge orgasm. Jim tried desperately to suck and lick all of the cum running out of me. God it was so good. As I finished cumming I reached down and felt his crotch again. For a man who just poured all of his sweet cum on me he seemed to be rather large again. I just knew I couldn’t let the evening go by without giving one seductive blow job. As he moved his face from my pussy, I leaned forward and was able to go down on him. I sucked and kissed the tip of his dick while I used my other hand to stroke him. He couldn’t believe I was doing this to him but again moaned how good I was. After sucking and licking him for just a short time he tensed again and I knew he was ready to cum. He pulled my head into him more and I was able to take as much of him in my mouth as I could. I felt him explode in my mouth and being the expert I am, I was able to swallow his cum and let it run into my throat as he ejaculated. Not as much cum as before but it seemed to be a rather large amount too. Well he finally emptied himself and our lustful event had finally concluded. I guess I can consider this another Christmas to remember…………