Before we start can I just say that anyone who gives me hassle for spelling mistakes please understand that this is U.K. English. This story has been run through a UK English MS Word spell and grammar checker so if it is still not right blame Bill Gates.
Who has not had a fantasy of sleeping with an older woman and luckily I have discovered the secret to doing this, it requires a bit of cleverness, a bit of bravado and a talent for knowing when to say the right thing.
So far I have managed to sleep with 9 women aged over 50 which for a 25 year old man is quite an achievement, the vast majority have just wanted to feel wanted and attractive and the trick is to make them feel special. All of the ladies I have slept with have been married and are not looking for love; all they want is to get fucked.
Oh and by the way my name is Steve, I work in an office as I.T. support and some of the women I have met I did meet in the office one of whom is a lady called Cynthia, she is the head of archiving and is a sweet lady in her late fifties who is very prim and proper until the day of the last Christmas party when I shagged her in my hotel room.
Cynthia dresses like you would expect an elegant lady in their late fifties would dress, sensible shoes with trousers or knee length skirt, a button up blouse and cardigan or jacket complete the ensemble, she always wears half moon glasses with a chain so they hang around her neck when she is not wearing them. She has grey hair and an attractive but not stunningly beautiful face, she is about 5 feet 6 inches tall and is a UK size 10 with D cup breasts with nipples like pencil erasers when erect.
I am 6ft tall and play football at the weekends so am still quite trim, I have dark brown hair and a face like Bryan Adams apparently. I can also talk the birds from the trees and middle aged women out of their knickers, I'm not sure where it comes from because my dad is a morose man with no discernable skills at speaking to ladies and my brother can't pull even though I can, we look similar and use similar chat up lines so is it the way I deliver them or is it my smile? Who knows and to be honest I'm not that bothered.
The first time I met Cynthia was when she reported a fault with a printer and I was assigned the job. She looked at me over her glasses and smiled when I explained who I was and what I was doing in her area.
Her smile lit up her face and she went from looking like a librarian to a sex goddess in my eyes, she removed the glasses from her face and sucked the end of one of the arms in her mouth as she listened to me talk, after 10 minutes I had got the printer working and I showed her what to do if the problem happened again and she seemed grateful as she touched my arm and said in her wonderfully soft voice "I'll ask for you again."
A week later I was sitting on my own in the staff restaurant at lunchtime when I heard her voice ask "Is it ok if I sit here?"
I looked up and smiled and said "Only for my favourite archivist," and pulled the chair next to me out so she could sit down, she returned my smile and sat down next me and we chatted as we ate until it was time for me to go back to work. "Can we do this again, I don't get much chance to spend my time with a good looking lady?" I asked.
She blushed and said touched my hand and said "I would like that once a week just you and me."
"It's a date," I replied and took my tray to the clean up area and waved as I left.
For the following 6 weeks we met every Wednesday lunchtime, I discovered that she was married to a man called Gerald and had been for 30 years, I playfully told her that if she ever fancied a change to let me know and I would gladly step into the breach and she giggled and placed her hand on my knee. She didn't object when I did the same thing and for the 6th "lunch date" we sat close to each other and that is when she asked "Are you going to the Christmas party in a couple of days time?"
"Yes, I'll be there, I was hoping I would see you dressed up in something sexy and revealing," I replied.
She giggled and said "I've bought a new dress, I hope you will like it."
At this point I knew I could get her into bed, she was going to wear a dress that she hoped I liked and had told me so.
"I've booked a room at the hotel so I don't have to worry about taxis, you can use it to get dressed in if you like?" I offered.
"My husband is away which means I would have to get a taxi there so it will make live easier," she said thoughtfully, "but you cannot see me get changed as after all I am a married woman."
"I shall be the perfect gentleman but if you look too gorgeous I may not be able to control myself," I replied.
She looked at me, smiled and just said "down boy," and then it was time to go back to work, we were the only ones in the lift back to the office floors so I slipped my card with my mobile number on it to her and smiled and gave me a little wave when she exited the lift on her floor.
Friday lunchtime I got a text from Cynthia asking if my offer was still open and I arranged to meet her by my car just after everyone had left so that we wouldn't be spotted. We chatted on the way to the hotel and I checked in when we got there and we walked to the room, the evening was smart casual so I had a quick shower and dressed in a shirt and chinos and left Cynthia in the bathroom, I watched TV and had a couple of drinks from the mini bar and passed Cynthia a couple when she opened the door a crack.
After 45 minutes she called ready and opened the bathroom door. I sat there with my mouth open and just said "Wow." She was wearing a yellow thigh length dress that was strapless and fitted where it touched, she looked absolutely stunning and so I told her so "Shame you are married or I would try and have my wicked way with you," I responded and she blushed.
She looked at me and said "Do you like it then?"
