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By (user no longer on site) OP
over a year ago
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These stories usually go the other way around. An older male boss having his wicked way with a younger female employee and I guess there's something more exciting in that. Something that more guys can relate to and get turned on by. However I'm not really one for conventions so I think it makes sense that my story flips that around. I'm going to relate to you the time I was seduced by my older female boss.
It wasn't quite a tale of virginity loss but it wasn't far off for me. I'd had a couple of fumbles and a nervous, long-planned night with a girlfriend the sane age as me when I was a year younger. This though was the start of my sexual awakening and the things she introduced me to or the particular things I remember about her are still guaranteed to get me hard or get me off much quicker than anything else. A white blouse; a pencil skirt; stockings; an old fashioned 80's style hairy bush; big, pink areolas; a front-opening bra. I'm half hard just thinking about the clothing she wore to be honest, never mind her distinctive body parts. She wasn't the first woman I'd has the pleasure of but she was the first I'd known who had embraced her sexuality and knew how to use it and importantly for me, how to guide me around her body. She was a wonderful teacher and it would be years before I met anyone to compare to her.
It all started when I was 17. I think Helen must have been early 40's but possibly late 30's. I never really knew for sure. She was what would be called now a milf. That term didn't exist back then but it's a pretty accurate descriptor. I knew I'd like to fuck her from the moment she introduced herself on my first day. It was quite a large company and she was head of personnel. I was starting as an office boy, first job out of school and eager for a pile of disposable income to blow on weekends out and my car.
I was sat at a desk filling in paperwork. She came out her office, and introduced herself. I later found out she'd arranged for me to have the desk in front of her office so she could watch me as I worked. She'd had her eye on me from the moment she saw me and what followed over the coming months was entirely orchestrated. Some say she used me and I guess that's true, but had I known I would probably have eaglery gone along with it.
Anyhow, where was I? Ah yes, she stood at my desk and looked at my paperwork, pointed out something and told me the correct way to follow in whatever it was. Then she bent over. Right in front of me. Her blouse gaped and she carried on speaking but all I could see were her breasts, hanging like full ripe melons (cliché I know but they were just that size) encased in a white lace bra. Her cleavage was dark and inviting and though she was still talking I was lost in the curve of her flesh until she stood up and asked if that was ok, if I needed more help to see her. Then she turned and went back into her office. I was left with a semi and a beautiful memory. This is where it all started.
I wanked myself silly that night. I was giddy at being so close to those big, beautiful breasts even though I was pretty sure it had been accidental on her part. I went straight to my porn magazine stash and spent the night imagining Helen's face on several of the Reader's Wives. I wondered what her nipples looked like. Were they big and dark pink like Annette's (43, brunette from Derby, 36D) or small, smooth, pale torpedo tips like Beverley (34, blonde from Chingford, 34C)? Maybe there was a thick dark bush between her legs like Jacqui (40, brunette from Dudley, 36F) or was she smoothly shaven with meaty lips like Kelly (37, short blonde pixie cut from Hounslow, 32B)? The possibilities swam around in my mind as I came again and again and again. By the morning I think I'd imagined Helen posing for my camera in every position possible running through a naughty photo shoot scenario in her office.
That made it kind of awkward when she called me in to see her first thing in the morning. I sat down at her desk, trying to banish the thoughts I had been having about her. Quite apart from the embarrassment I was feeling I was keen not to lose my first job on account of some indiscretion, imagined or otherwise. Helen stood and walked round the desk to close the door. This seemed serious. I could feel her eyes on me as she walked back to take her seat. She sat down and looked into my eyes as she started to speak. She told me that she was happy with my work so far and thought I could progress far. She would like to help me do that, if she could and if I was willing. She leaned forward and I couldn't help but notice that her blouse was unbuttoned rather low. Her breasts rested on the desk and squeezed together, showing an ample amount of cleavage. The way to progress in this business she said, was to put in the hours, over and above, get yourself noticed and get a reputation for reliability and work ethic. Would I like that? I replied that I would and wasn't afraid of hard work. Good she replied, if you can stay an hour later tonight I'll show you something I've been working on alone. It will be much better with your input though. I agreed and she said see you at 5pm sharp.
5pm rolled around and as the other office staff were leaving I knocked on the door of Helen's office, entering as she called for me to come in and closing the door at her request. She smiled at me and closed the blinds. Taking her seat she told me that she needed my help with a rather particular problem. I'm a career minded woman she explained. It wasn't easy for a woman to make it in this environment. She was divorced, had made sacrifices to pursue her career and wasn't going to stop. That left little time for building relationships and after her wreck of a marriage she wasn't looking for a man to be worth in any traditional sense. She was focused in herself. However that didn't mean she didn't have normal appetites to satisfy.
At this she opened a drawer and took out a long, thin plastic vibrator which she put on the desk in between us. I want you to help me unwind. To relax. I saw how you stared at my breasts yesterday. I think you're interested in me and I am interested in you. I would like you to be my sexual release. I can only perform in my job if my other urges are satisfied. A young man like yourself has a libido to match mine so I think we are well suited. This would be purely about sexual release. If feeling become involved we would end the arrangement.
She picked up the vibrator, touched it to her lips and kissed it, then pointed it at me. What do you say?
I couldn't do much but nod enthusiastically. She smiled and laid out ground rules. One: We have sex when I choose. I expect you to be reasonably available. Two: Nobody apart from us is to know. Three: You're free to have other relationships or sexual contacts provided they don't infringe upon our arrangement. Four: You will pratice safe sex with any and all other females. Five: We will not use condoms. I do not like the feel but will take contraceptive measures and bear that responsibility. Six: I will teach you how to make me orgasm and ask that occurs at least once each time we have intercourse. Seven: I will advance your career in return for this. Eight: I realise that as an older woman I might not quite be your type. I will give you an opportunity to see me naked and if I'm not to your taste we'll call off the deal and not mention it again. I won't hold it against you. Ok?
I agreed wholeheartedly. She offered her hand and we shook on it. Lock the door, she told me. I did so and felt a growing bulge in my trousers. As I turned I saw her breathe in deeply, steeling herself for the moment to come, and I realised that underneath the hard, confident businesswoman was something softer, more vulnerable. Like those Reader's Wives shots of bare breasts and open legs, the smiles disguised the fragile intimacy of the situation and made them all the more attractive.
I sat on the swivel chair, my hands gripping onto the sides and could feel my palms becoming sweaty. Helen came around to stand between me and the desk. She put her foot on the chair, between my legs and rolled me backwards, creating a wide space between us. I'd seen a couple of strippers at the pub before and her movements reminded me of them and I wondered how many times she had taken off her clothes like this. She started with her with satin blouse, unfastening each button and letting it fall off her shoulders to the floor. Her body was lightly tanned and she was wearing a pale blue bra which held her ample tits proudly. She ran her hands through her hair, down the back of her neck across her chest, lingering on them, then down the sides of her nicely curved torso. Her tummy wasn't flat but not fat, just a nice curve to it. She looked at me questioningly, as if asking my approval, and I smiled at her which she returned with a glint in her eye. |
