Jenn and I have worked together for over two years. We are both in the accounting department of a large firm which I will not mention here for privacy reasons. I head up the accounts receivable division and Jenn is one of my staff members. We have become good friends over that time and though we had never seen each other out of the work place we did spend many lunch hours together chatting. Most days we would just head to the cafeteria in our office building but once in a while we will go out to a restaurant that is close by.
It was on one of those days at the restaurant that the seeds were planted that would change our relationship and open my eyes to a whole new sexual world. We had finished our meal and the waitress was refilling our coffee cups. She was young, I would guess around nineteen. Her blouse had three buttons undone and when she leaned over to fill our cups it gave me a very nice view of her ample cleavage.
I guess I must have been staring because as soon as she left Jenn said, "She has nice breasts, doesn't she." "Ummmmm, ya I guess so," I replied. "Oh I saw you looking," she accused, "don't pretend you weren't." "I was just remembering the days when mine were firm like that." While I was only 36, two kids and gravity had started to take their toll and my breasts were just not as perky as they used to be. "You have beautiful breasts," she responded. "I wish mine were bigger like yours."
"Oh sure they look ok when they are all held up in a bra, but are a little too saggy for my liking when I let them run free. You on the other hand, while they may be smaller than mine they are very perky. I think I would prefer to be more like you and sacrifice the size for the firmness."
"Is that not always the way, we all want what the other person has," Jenn commented with a laugh. Then she got a little more serious, "Can I ask you a personal question?" "Sure." "The way you looked at the waitresses' breasts got me wondering, do you like women?" "Do you mean like in a sexual way, like lebian?" I asked. "Yes, have you ever been with a woman sexually?" "No!" I quickly replied. I paused for a moment then continued, "Ok that is maybe a little bit of a lie, there was one time at a party, we were all drunk and with the encouragement of the guys there, me and another girl kissed and she groped my tits. But that was just a drunken, spur of the moment thing. I have never been farther than that. Ok I may have thought about it from time to time but have never acted. I sometimes look. I love the shapes of a woman's body but....." I realized now I was just rambling on as I let the sentence trail off. I had to get the subject off of me before I said something really stupid. I figured I would turn it around. "What about you, have you ever been with a woman sexually?"
"Yes," she stated matter of fact. "A number of times when I was younger.My first time was in college, but not I have not had a lesbian partner for the last few years." Just then the waitress returned with our bill, we paid up and left as we had to get back to the office. Not another word was said on the subject for the rest of the day.
It was just after five thirty when Jenn came into my office, most people were on their way out and I was just setting aside some files I would need in the morning before I also headed home.
"Have a good night," she said, "see you in the morning." With that she grabbed the bottom of her top and lifted it up exposing her naked breasts to me. I think I must have just sat there with my jaw on my desk. With that she just smiled, lowered her top and turned and left.
As I drove home that night Jenn was all I could think about. I could not get the image of her breasts out of my mind. That night after my husband and kids were in bed I masturbated thinking about her.
The next morning I only saw Jenn once in the hallway in passing and there was not an opportunity to stop and talk. When lunchtime came we met in the cafeteria but there were some other ladies with us so we could not discuss what had happened. As the afternoon wore on I realised I was getting little done because my mind kept wandering back to Jenn.
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When five o'clock came I had made up my mind, I went to the wash room and removed my bra, before heading back to my office. Just before five thirty, I called her on her extension as asked to see her before she ran off for the day. When she came in ten minutes later I asked her to shut the door. As soon as she did without a word I lifted my top exposing my breasts to her.
She grinned, winked at me and said, "I will be thinking about those tonight. See you in the morning."
I lowered my top and she turned and left. The thought of her masturbating to the vision of my breasts really turned me on. Before I left work that night I waited till things quieted down and slipped my hand down my pants and fingered myself to orgasm. The next morning Jenn was still on my mind when she showed up at my office door. She sauntered over to my desk and leaned over giving me a nice view of cleavage. "Do you want to make this more interesting?" she asked. "What do you have in mind?" "A little challenge," she offered. "Winner gets to choose." "Choose what?" "What they want to other one to do." "Within limits that is?" I asked. "Of course, nothing that would get us fired or upset your marriage." "Ummm Ok, what is the first challenge?" "Well I called 'Superior Contracting' this morning to ask about their overdue account. They said the cheque was in the mail. I don't believe them. I don't think they have sent it yet. If it is already in the mail then it would arrive by Friday. If they put it in the mail today then it would not arrive till next week. I bet the cheque will not arrive till next week." "Ok you're on; if it arrives this week you owe me." "Deal," Jenn agreed. "See you at lunch."
Today was Wednesday no cheque came today from 'Superior' and no cheque came on Thursday. As Friday rolled around I don't know if I was hoping there was a cheque or not. If I won I had no clue what I would make Jenn do and if I lost I did not know what she would want. If I did lose would I have the courage to honour the bet? The tension was killing me and I just wanted to get it over with. When Jenn entered my office just after eleven that morning the smug look on her face told me who had won.
"Don't even think about leaving early today. I have plans for you," she said. She turned and with a little wiggle of her ass left my office. At lunch every time I looked across the table at her she was looking back with an impish grin which had my mind whirling about what she had in mind. For the rest of the day my mind played through the possibilities of what she might make me do. I was nervous like a teenager on a first date but the dirty thoughts running through my head were also taking me to a state of heightened sexual arousal.
It was just before six when she came to my office. "Just about everyone is gone," she said as she locked my door behind her. "Are you ready to fulfill your part of the bet?"
I could not speak I was so filled with nervous excitement. I just nodded.
"For losing today's bet......," she paused to heighten the anticipation. "........I want you to masturbate for me." Just hearing the words from her mouth almost sent me over the edge. I could do this. I needed it so badly anyways. "Ok but shut off the main light so anyone who comes by will think I am gone," I asked as I turned on my little desk lamp.
She moved over and flipped the switch, then returned bringing a chair around the desk and sitting down a few feet away to watch. I had worn a button down blouse and skirt today and started by undoing my top, revealing my bra enclosed breasts. Normally when I masturbate I like to play with my nipples first to get them hard but there were already aroused so I pulled and flicked them through my bra for a couple of minutes.
"Get them out," Jenn whispered. In the dim light I could see was intently watching my every move.
I reached around and undid my bra clasp, then slipped them out of their confinement. I continued flicking, twisting and rubbing them as I watched Jenn watch me. I then raised one to my mouth and flicked my tongue over the nipple. I heard Jenn moan when I did that and knew she was as horny as I was.
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