Tem 13, 2022 // By:analsex // No Comment
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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?”
“The way you looked at the waitresses’ breasts got me wondering, do you like women?”
“Do you mean like in a sexual way?” 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 factly. “A number of times when I was younger, in college, but not 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 realized I was getting little done because my mind kept wandering back to Jenn.
When five o’clock came I had made up my mind, I went to the washroom 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 izmir escort bayan 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.”
“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 honor 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.
“More,” she said. “I want to see more. I want to see you cum.”
I stood up, reached under my skirt and removed my panties. I laid them on the desk and sat back down, hiking my skirt up and placing a leg over each arm of my chair exposing me wide open to her gaze. My nervousness was gone as my sexual needs took over. I placed my left hand back on my breast and my right I slid down to my wet pussy. As I ran my finger across my clit I closed my eyes and moaned. I was already so close to cumming. I continued rubbing and in less than a minute I was orgasming. When I opened my eyes Jenn was staring at me, my panties were in her hand she had then pushed up to her nose smelling them.
“Again,” she said. “I want to see you cum again.”
I did not think that would be much of a challenge as I slipped a finger inside and started to fuck myself. I alternated between fucking myself and rubbing my wet finger over my clit and within five minutes I was cumming again for her.
“That was great,” she said in a breathy voice. “Thanks for the show.”
She got up to leave but I stopped her. “Now it is my turn to pick a challenge. You up to it?”
“Challenge away,” she said.
“Ok, Peter is going to Vegas for the weekend, he is due back Sunday evening but I bet he will call in sick Monday morning to get an extra day.”
“Sure,” she agreed. “If he is in, you owe me again, if not I owe you. Deal.”
As she left I straightened out myself. It was only after she had left that I noticed she had taken my panties with her. I was still worked up and on the way home I fingered myself escort izmir again in the car.
On the weekend I thought about what I could make Jenn do. I came up with what I thought was a great idea and headed down to a local adult store to pick up what I needed. Monday morning I was disappointed when Peter walked into the office.
When Jenn saw me that morning she said, “Seems like I am on a winning streak. I will have some instructions for you later today baby.”
I was a little disappointed that the item I had bought in anticipation of a win would have to sit in my bottom drawer and wait for another time, but then again the thought of putting out again did not bother me.
Late that afternoon Jenn came into my office with my instructions.
She looked at me in an authoritative kind of way and ordered. “Tomorrow, when you come to work, you will wear a short skirt, something that comes above your knees. You will also not wear panties. Oh and bring something to snack on at your desk because we will be busy during lunch hour.” With a wink she turned and left.
My mind raced with the possibilities of what she had in mind. Which of course got me very excited. This in turn, forced me to lock the door to my office at home time and finger myself to orgasm.
As I dressed the next morning I was already wet. I had been having erotic dreams all night about what she might do and the anticipation was killing me. I had got up extra early and showered and shaved myself clean. I dressed in a nice blouse and a skirt that came about three inches above my knees. Nothing too indecent for work but easy access if it was needed.
Just before noon Jenn came in. “Ready to go?” she asked.
“I’m more ready than you know,” I replied.
“Good, were off to the mall then.”
The mall? What could we be doing at the mall? My mind again reeled with the possibilities.
As we traveled there I tried to get her to tell me what she had in mind but she put me off telling me I would have to wait and see. When we did arrive she led me to a bench toward the South end of the mall and sat down.
Across from us was a shoe store and Jenn pointed towards it saying. “Ok the first thing on our agenda is for you to expose yourself to a complete stranger.” The look of shock on my face made her laugh. “Oh you can do it, see that girl at the shoe store over there, her name is Lindy. I have bought shoes from Lindy before and got the ‘vibe’ from her. I have the feeling that she is a lesbian or at least bi-sexual. Your assignment is to go in there to get a pair of shoes. Have Lindy help you and as you try on shoes you will let her see up your dress to your exposed kitty. I will be watching from here to see yours’ and hers’ reactions. When you are done come back here and we will move to part two of this little adventure. Ok go to it.”
I just sat there. I did not know if I could just do that with a stranger.
“Need I remind you that it was you who suggested the latest bet that you happened to lose?”
I shook my head no and on weakened legs I stood up and headed towards the shoe store.
There were two sales girls in the store and I moved near the section where the girl Jenn had pointed out was working. I looked her over. She was in her early twenties, dark blonde hair, ruby lips, and nose stud. She was very thin, a little too thin for my liking, and small breasts. The one thing that drew me to her was her smile; it was beaming as she asked me if she could help me.
“Yes I would like to try on some shoes please,” I responded.
“Sure what would you like to try?”
I quickly looked over the selection and pointed to two pairs. “Can I try these two please, in a size eight?”
“It will be just a moment,” she said, as she disappeared into the back room.
I took a seat in one of the chairs, making sure my dress was high up on my legs.
When Lindy returned a couple of minutes later she knelt down in front of me and pulled up a foot rest. I lifted my foot and she slipped the pump I was wearing on my right foot off. When my leg had lifted I had felt a breeze across my lips it told me two things, I was exposed to her gaze and I was wet. She removed one of the shoes from the box and slipped it on my foot. As she started to look up I saw her eyes widen as they spotted my exposed womanhood. It was only a slight hesitation before her eyes continued up to my face.
“How does that feel?” she asked.
“Not bad,” I answered. “But I don’t think it is really grabbing me, could I try the other style on too?”
Her head moved back down and she started to remove the shoe. Her head was tilted down but I could see that her eyes kept darting up looking up my dress. It took her longer than it should have to get the shoes switched around as she was fumbling a little.
“How about that one?” she asked when she was done.
“Hmmmmm, no I don’t think this one really suits me either.”
“I have something you might like,” she offered as she removed the shoe. She packed the second pair away still kneeling before me stealing peeks. She then got up and went to the back room again.
God I felt wet, I hoped it was not too obvious to her just how aroused I was.
She returned a minute later with another pair. “These are some of my favorites,” she said as she got back to work placing it on my foot. When she did the ankle strap up her hand stayed on my leg for a long time and seemed to give it a small caress.
“Oh, those are pretty, let’s try the other one on too,” I said.
As I shifted from on leg up to the other I was sure a felt a bead of liquid run down the crack of my ass. I was so embarrassed but so turned on at the same time.
Again Lindy took her time getting the other shoe on, her hands lingering on my leg, her eyes darting between my thighs. When she was done I stood up and walked around in the shoes.
“Those look great; I think I will take them.”
“Would you like to wear them out or carry them?” she asked.
“Carry them I think,” I replied. I wanted to give her one more chance to have a look. I sat down, making sure my skirt was even higher than before as she got to work removing the shoes and getting one last eyeful of me.
I paid for them and headed back out to Jenn.
“So how was it?” she asked. “I saw her eyeing you up.”
“I was so nervous but it was very exciting.”
“Great, we have twenty minutes; on to part two. Come with me.”
She took me further down to the mall to a women’s clothing shop. We enter together and Jenn moved over to a rack of clothes. She browsed through them for a minute before selecting one outfit.
“Come with me,” she commanded.
She led me to the change rooms in the back and we both entered one. She hung the outfit on one of the hangers and turned to face me. “I just wanted to see how that last encounter affected you,” she said.
With that she stepped over to me and reached her hand up under my skirt, her finger slid between my wet lips and up over my clit. My legs quivered and I thought they might give out right there. She slipped her finger down and inside of me, commenting on how wet I was. She started to slide it in and out as she finger fucked me. First slow then faster and harder. I exploded in orgasm in that public change room, my moans muffled in the crevice of her neck. She then proceeded to lick her finger clean before returning the outfit to the rack and both of us heading back to work.
For the rest of the afternoon I had to keep using tissue to mop myself up before a left a wet spot on my skirt and chair.
These adventures were really turning me on. They were all I could think about. Jenn was ready for more too. The next morning she stopped by my office with the next challenge.
“I don’t know if you heard but Henry lost the ‘Hopkins’ account yesterday. I hear that they are going to fire him and I bet that he will be gone by the end of the day,” she challenged.
“They would not do that to Henry, I will take that bet.”
I still saw Henry there that night when leaving but waited till I saw him there the next morning before showing up at Jenn’s cubicle to gloat. The funny thing is that they had escorted Henry out by noon that day but that bet was that he was to be gone yesterday. I had my first win.
“Come to my office first thing in the morning tomorrow and we will get started,” I said with a smile that would just not leave my face. A few people commented that day how happy I seemed. If only they knew what I had waiting for Jenn in the bottom drawer of my desk.
The next morning Jenn was there right at eight. I asked her to lock the door and have a seat.
“Well, it seems the tables have turned.” I crowed. “I have a little something for you.” I reached into my drawer and removed a package contained in a brown paper bag and handed it to her.
She removed it from the bag to have a look. “It’s called the Butterfly and it is designed to wear like a pair of panties,” I explained. “You will notice that it has a butterfly shaped device that fits right where your clit is. The other item in the package is for me. It is a remote control that turns the vibrating action on and off and controls the speed. I want you to wear this for the day.”
She looked up at me, a thoughtful look on her face. Then that little impish grin of hers crept in and she said, “Alright.”
She opened the package and we inserted fresh batteries in the device and remote. She then slipped off her pants and panties giving me my first wonderful view of her pussy. She was shaved bare except for a thin strip running up. She put on the Butterfly and then her pants.
“I will keep those panties for you,” I said as I took them from her and gave them a sniff before putting them in my desk drawer.
“That is all,” I said and she got up to leave. Just before she got to the door I stopped her. “Wait a sec, let’s give this try.” I turned the remote to slow and I saw her eyes close briefly and her thighs clench as the vibrations were sent over her clit. To see what would happen I turned it up to max and Jenn’s legs started to buckle and she almost fell to her knees before I lowered it back down.
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