When Janie got the urge for a smoke she would most ofter find me to accompany her. She was my boss and had been for the last two years. She felt guilty sneaking out so would include me to ease her conscience with the idea we could be discussing the work load while we smoked. I had become her confidant and right hand man in the last year. My first year with her, she saw me as a threat but with no attempt at usurping her authority and proving my self to be industrious, even sometimes cleaver, I became a friend.
We often talked of business while appeasing our nicotine craving and joked around a lot. It was good natured and always sexual but she was married and had shown no intention of starting an affair. I had recently told her of my sexual philosophy. Things like “ the worse piece of ass I ever had was magnificent”and “ the best I won't know about until you say yes”.This is her second marriage and she is happier than she has ever been in the past but you could tell life still isn't quit right for her. She is of average height with a nice figure. Short red hair and medium sized breasts. I found her body to be sexy and her face attractive.
She was complimenting and thanking me on my latest bit of dazzling brilliance that had saved the whole departments ass. I had seen a paperwork screw up that would have caused a ton of useless work and been a big embarrassment to our immediate upper management down the road. I had told her to take credit for the find, as I didn't need the recognition but to remember it at review and raise time. She had been pressing me to be her fill in when she went on vacation. I have never been happy as a boss and had refused most temporary and all permanent positions. I was happy going through life smokin and jokin.
Today she had said I had a knack for “thinking outside the box”. My reply was all I think about is getting inside yours. She had turned a little red but not to be bested by my wit, countered with lets make it interesting and see how clever you can be attempting that. I will stand here and let you try but you cannot use your hands. I asked if that meant I couldn't use them or touch her with them. Her reply was not to touch her or her clothing with them and if I did or couldn't complete my quest in a reasonable time I had to be her vacation replacement.
We were behind the building in a fenced storage area with only one entrance which was blocked from view by large wooden containers. The entrance is about 50 yards away so you can hear the heavy metal doors open if someone is coming out and would have ample warning. I had been back here with other women to do a little groping and making out, so new it was safe.
She was leaning against a pipe safety rail. She had one foot hooked on the bottom rail which was about two and a half feet off the ground as she usually did. The top rail was about two feet higher and I always thought it was a provocative stance with her one leg up and spread like that but it was not exposing anything. Today she had on a dark wool pleated skirt with bare legs. Her legs were tan so she could get away with it. My mind was running a mile a minute figuring how to go about this when I came up with a plan.
Lets get the rules straight first I stated. You have to keep both hands on the top rail and your right foot on the bottom rail just as you are standing now. If I can get it into you without touching you with my hands I can have sex right now. She thought about it a moment and said “yes” but if you can't or you touch me with your hands you have to cover my vacations as long as you are working for me. I added since the stakes went up if you remove either your hands or your foot before I’m finished you have to give me a blow job with a climax. She almost choked but nodded reluctantly and said “agreed”.
We were both smiling at each other and I could tell she was thinking I had backed myself in a corner and all she would have to do was stand here and watch me fail. I asked if she had any other rules and if she was sure she wanted to go through with this. Janie was one of those people that would not back down from a challenge no matter what, which I was using against her and almost felt guilty for. I told her I was not kidding and it was her last chance to back out.
She said do your best smart guy and prepare to be my defeated vacation replacement for a long time. My first move was going to be the toughest for me. It would be to unzip and pull my cock out in front of her. I'm not shy but that is a dangerous thing to do with today’s sexual harassment views. I was thinking maybe I had made a mistake but the thought of sticking my dick in her was to tempting to pass up.
I was already getting an erection which helped since I wouldn't have to pull a small limp dick out in front of her and be even more embarrassed. I did pull it out and stood in front of her and the expression on her face was priceless. It was such a shock she almost lifted her hand from the rail. Her face turned bright red and her eyes got big. I think she had expected me to try some rubbing around and have to admit my failure.
I removed my Cross pen and pencil set from my pocket and knelt in front of her. Taking one in each hand I used the left to lift her skirt above her waist and was happy to see she had on normal panties. I took the other and slipped it in the side of her panties and pulled them across to the other side of he mound where they stayed very nicely. Her pussy hair was neatly trimmed short and she was not a natural red head. She started to squirm as I purposely let the pen slide into the cleft of her vagina and rubbed it up and down before putting it in my mouth. With her panties aside and pussy spread wide I put my tongue against her slit and slide it into her licking up and down against her clitoris. She was moaning and saying at the same time this was not what was supposed to happen. Her pussy smelled very strong and she was immediately leaking juice that I was lapping up with great enthusiasm..
I stood up still holding her skirt up and was looking her in the face. My dick was rock hard and as I stepped forward and placed the head in her wide open slit. I pressed and starting to penetrate her vagina. I could feel the heat inside her as my cock just barley entered and I stopped with just the head in. I then looked into her eyes again and she was crying but turned on at the same time. I didn't know what to say and for the first time felt that I had fucked up big time. She had not tried to stop me and I wanted very much to plunge my dick into her but couldn't bring myself to take someone unwillingly. I backed up and pulled both pens away, putting them in my pocket. I then took my hand and laid it on her arm and said you win as I turned around and started putting my cock back in my pants.
She put her hand on my shoulder and turned me around before I got it put away. She reached down and took it in her hand and squeezed very hard. Then pulled me by my cock toward her and said I had to win but you are still going to put that inside me before I go crazy or I will have to stand here and make myself cum before we go back.
I said I would love to see that as I lifter her skirt again with one hand and held her panties aside with the other. She took the other hand and started running her finger over her clit and then deep into herself.
I watched as she massaged and masturbated both of us for a couple of minutes. We were both breathing hard and ready so she guided my dick into her very wet pussy. She was burning up inside as my dick slowly slide all the way in. All pussy is hot inside when you first penetrate but Janie’s felt like it had a fever. The first two strokes were very slow and made me think I would have burn blisters on my cock later. On the second stroke I stopped at full penetration and slid both hands under her sweater lifting it over her breasts. I pulled her bra up and over letting both boobs fall free.
I would have had to pull my dick out to get them in my mouth so I took each nipple between my thumbs and index finger, pinched and rolled them around. She was bent back over the rail with her eyes closed and moaning in pleasure. I started with the slowest and longest strokes I could manage, then soon began pounding away. I was getting great penetration with her foot still up keeping her legs wide open. Within four or five minutes she was cumming and with her thrusting her hips back at me it brought mine on also. We finished and as I pulled out and stepped back the sight was so sexual I wanted to go again. She stood there with her foot still up and panties pulled aside with my cum leaking in big globs onto the ground. Her sweater and bra were still pulled up over her breasts. The sight was intoxicating to be clothed but at the same time have everything exposed.
When she recovered her breath she asked me to hand her purse to her for a Kleenex. She didn't have one and said she was going to be big mess before she could get to the ladies room. Seeing the dilemma she was going to be in I stepped forward and squatted before her, putting my mouth over her vagina. I had never gone down on a woman right after shooting a load in her before but figured if a woman can swallow my cum I guess I can. I then sucked and licked all of our remaining love juices from her until all that was left was her starting to get aroused again.
I continued working her pussy over and she was approaching another orgasm. She wanted me to stop but I persisted and soon she was in the thrall of her second orgasm. As she finished I stood and said we had better leave before we get so excited we have to have another go at it. She put her foot down and looked unsteady. I stepped forward and helped her straighten her bra and sweater. I reached down and pulled her panties back into place and patted her vagina mound. She stood there shakily and said my first multiple orgasm and as we walked back to the building she said (with a lewd grin) the first time I ever saw a man clean up a mess he made.
She came and got me for another smoke late that day and wanted to talk about what happened. The following was how she felt about our situation:
My husband has not had sex with me for about six months and when this started as a joke I was hoping you would find a way to make it happen. I was sorry for the tears but they were more tears of joy than shame or guilt. I knew you would feel guilty and I had to win. I new you would not put it in me if you thought it was going to hurt me emotionally. Cheap trick but a win is a win and that was the most erotic sexual experience I ever had. A day of firsts -My first time standing, first time outside and first multiple orgasm which made it the best fuck of my life. What new experience do you have planned for our next time and I hope I don't get wet every time I have a smoke just thinking about it.
Boy is she going to be pissed when she finds out that I was offered a job I will probably take in three months since her next vacation is in six months away. I’m not going to tell in the meantime. My mind is already thinking of a way to get my dick in her ass and a good blow job.