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 4 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?"
"I love it and it makes me wonder what you would look like out of it," I replied.
She smiled and just sighed "I'm married and old enough to be your mother."
"Doesn't mean that I can't find you attractive though," I said.
She laughed and took my hand and said "Let's go to the party."
When we got there I spent some of the evening with my team and she spent some of the time with hers and we both had a fair amount to drink. The slow dances started about 10:30 and I as asked to dance by a few ladies but I politely declined until I felt a tap on my shoulder and there stood Cynthia. "May I have the pleasure of this dance?" I asked.
"You may kind sir," she replied and she took my proffered hand.
We danced in the darkest corner of the dance floor and by the end of the 3rd song my hand had moved from her hip to her bum and she had wrapped her arms around my neck, I looked around and everyone else was too drunk or wrapped up in their own dancing to see what we were doing as I pulled her close so she could feel my hard on against her hip, "did I cause that?❤" she asked.
"Well I'm not dancing with anyone else," I replied and kissed her gently on the corner of her mouth. She looked around and then kissed me back with recklessness and a passion that I found surprising and we exchanged tongues until I said "My room now!"
She took my hand and led me straight to the room where as soon as the door was closed she leapt on me, we were kissing and groping each other against the door and before long we both naked but neither of us could remember removing the clothes and I picked her up and carried her to the bed where I lay on top of her and kissed her thoroughly before kissing down her body, her breasts had a little bit of sag but her nipples were enormous and I kissed down her body and sucked one of the nipples into my mouth, she gasped and panted as worked one nipple then the other and she started to moan when I stopped to be replaced with a giggle when she felt my breath on her mons and then a shriek as my tongue flicked her clit, for the next 10 minutes I worked her neatly trimmed area with my tongue and lips and played with her nipples with my fingers and then she came, she had been playing with my hair and then she stopped and I felt her whole body tremble and then she soaked my face with her juices and made a series of grunting noises as the orgasm wracked her body with sensations that she hadn't experienced for a long time, she was still trembling as I climbed her body and kissed her on the lips as my cock entered her sex with no guidance.
She wrapped her arms and legs around me and we kissed as we slowly screwed, she was panting and shook again as another orgasm radiated from her core to her fingers and toes, "Fuck me now❤," she commanded so I did.
My hips were a blur as I pounded her twat for all I was worth she let go of me and her legs and arms flopped onto the bed and she let me take her, I was there to use her body as I wanted and I just kept fucking her, after a few minutes I felt the familiar tingle as I knew my climax was approaching and so I warned her, "In me come in me," she said breathlessly and threw her arms around me again just as I felt the come shoot out of my cock, "Yes❤, Yes❤, Yes❤," she cried as she trembled and came again as she felt my seed splash her insides.
I stayed inside her for a few minutes with Cynthia grasping me close before I rolled off and lay on my back next to her and the only sound in the room was 2 out of breath people trying to regain their composure.
She turned her head and looked at me and rolled onto her side and threw and arm and a leg over me and rested her head on my shoulder, "Thank you❤" was all she said, I reached an arm under her neck and wrapped it around her and she cuddled me close.
5 minutes later she got up and went to the bathroom and came back after a couple of minutes and crawled under the covers with me and kissed me on the lips, "Thank you for making an old woman feel attractive❤," she whispered into my ear.
She rolled on top of me and I said "no thanks needed, the pleasure was all mine and you are an attractive beautiful lady who needs to be loved," as she started to play with my cock which soon reached full stiffness and she then raised her hips and lowered herself down on to me taking my cock deep inside her pleasure palace.
The next morning she snuck out of the hotel at about 6am to avoid being seen with me but only after making me promise that we would get together every now and then for a night of good old fashioned shagging.
One of my favourite other ladies I see on a semi regular basis is Fiona, she is 51 years old but looks older, she always used to look worried and stressed. She lives 4 doors from my house and lives with her husband and his mother, they seem to take the piss out of her and despite the fact she works full time they still insist she does all the cleaning, cooking and shopping, her husband is a fat lazy git and his mother isn't much better but due to their ways Fiona ended up in my bed.
Fiona is quite tall about 5ft 10 inches and skinny, she has small breasts that are still pert with nipples that point north. Her hair is grey and her face looks a bit like the Queens but she always has a frown on her face, one day I saw her walking home carrying the food shopping as the bus drivers were on strike, I was in my car and pulled over and wound down the window, when I offered her the lift it was the first time I had ever seen her smile despite being her near neighbour for over 6 months.
She dumped the bags on the back seat and got in the front and thanked me profusely. "I really didn't fancy the walk home with those bags so you are a true hero coming to my rescue," she said and briefly squeezed my hand.
"Why didn't you husband come and pick you up?" I asked.
"Because he said that he has had too much to drink," she replied with an annoyed tone.
I replied "forgive for saying so but he seems a total arse, you deserve a man who will treat you like the princess you are."
She blushed and straightened her hair before saying "You really know how to make a lady feel better about her self."
"Well if you didn't have a husband at home I would take you back to mine to try and have get you naked in my bed," I replied smiling.
We talked as I drove and helped her carry her shopping bags into her house when we got to our street, her husband grunted something about why had it taken so long and I pressed my card with my mobile number on into her hand and she said "thank you," before I left.
For the next 3 months I helped her with her shopping and I would meet her outside Tesco at 5PM. She was always waiting outside with a trolley. On day I pulled up and as it was late spring and getting warmer I saw she was wearing a blue zip up blouse and grey trousers that showed her bum to be pert and firm looking, the blouse was also tight and showed that she had a flat stomach.
I got out and helped her load the shopping into the boot of the car and then we drove home, she explained that her husband had never let her learn to drive so that she would be dependant on him, the only trouble now was that he was drinking more and was never sober enough to drive her anywhere. There was an accident on the ring road so we spent a while talking whilst waiting for the traffic to clear, "I'll teach you to drive," I offered, "though when you pass your test it means you will not want me to drive you about so I will miss spending time with the most beautiful lady in the street."
She looked shocked and then smiled and stroked my face and said "You really are sweet and I think you really are quite handsome. Just a shame I'm married and you are younger than me, "
At this point I knew I could get her on her back screaming for more of my cock if I played my cards right. I looked at her face
"Well age is just a number and I can forget you are married if you can," I replied with smile.
She giggled and said "Yeah right, you wouldn't want to sleep with me❤."
"Oh I would," I said.
"Prove it!" she responded.
"Let's drop your shopping off and then you come to my house and I will slowly strip you naked and then I will lick your bits until you scream and once you have stopped screaming and shaking I will feed my cock into your love tunnel and slowly make love to you or I could just rip all your clothes off and fuck your arse off," I responded.
She looked at me with an angry expression and just said "Take me home now."
Not a word more was said until I pulled up outside her house and then I helped her carry her shopping to her front door and then as I turned to leave she said "Where do you think you are going?"
She pulled me inside and took my hand and led me to her bedroom where she shut the door and kissed me hard on the lips, I unzipped her blouse and released the kiss and whispered "where's your husband?"
"Out and will be until tomorrow morning, now let's see if you are all talk❤," she breathed as she ripped my shirt off me. I pulled her close and kissed her whilst finding the button and zip for her trousers, I soon had then down around her ankles and pulled myself away from her welcoming lips, I kissed down her body and pulled her knickers off and then helped her step out of them, she had by now removed her bra and I saw a nice pair of pert breasts that were just begging to be sucked, she then returned the favour and pulled my trousers, pants and socks off and held my hand as I stepped out of them, we resumed kissing and fell on her bed and then I remembered about her mother in law. She must have read my mind and just said "she's away with my husband now what did you say about licking my pussy?"
I pulled her so her bum was at the edge of the bed and knelt on the floor between her legs and draped them over my shoulders. I then proceeded to lick and kiss her slit, hole and clit, I worked my tongue and lips over her area until she went stiff and came, she grunted and pulled my head fully into her groin as the orgasm flowed through to her extremities and then jerked a few times as the sensations passed, she let go of my head and in between pants of breath said "Sorry, will you do that again please?❤"
I stayed between her legs for another 15 minutes licking, kissing and sucking until she came again and then I stood up, she scooted back into the middle of the bed, spread her legs and beckoned me to her with her finger, I crawled over to her and lay between her legs, I then kissed her thoroughly as she run her hands over my back and arched her back ready to receive my love tool into her love tunnel. My cock entered her with no help from either of us and she sighed loudly as she welcomed the intruder that filled her in one movement, we kept kissing as we made love on the bed she shared with her husband. I felt like we had melded into one being as we kissed and screwed, after a few minutes of slow gentle love making I upped the pace and she responded with enthusiasm, we were flying our hips at each other and then she came again, this time she screamed and laid still as she felt all her nerve endings tingle with delight, I stopped moving in and out of her left my cock half in as she came, as she calmed down I rolled us over so she was on top so I could play with her deliciously pert breasts as she started to screw me hard, she smiled as she felt my cock touch her deep inside and started to quiver as another orgasm descended upon her senses.
"I'm coming," I announced and she ground harder until she felt my seed explode into her tunnel, she made a yelping noise as she came again and pressed my hands hard onto her breasts crushing them and I could feel her rock hard nipples between my fingers.
"You can come here again❤," she said after a couple of minutes and let go of my hands and collapsed on top of me and kissed me on the lips, after a few minutes she got off and lay on her back next to me.
"Now what?" I asked.
"You fuck me again when I've calmed down and this time I want us to do it doggy style❤, and then we go to sleep together and then you fuck me again in the morning before my dipshit husband gets home," she said in a matter of fact way.
"Sounds good to me but what I meant is this a one night stand or a more regular thing?" I responded.
"Unfortunately my husband isn't away that often but when he is I expect you in my bed fucking me, he has never given me an orgasm so you really are something quite special❤," she replied as she rolled over and rested her head on my shoulder and stroked my chest.
We talked for a bit before I fucked her doggy style as she requested and she was smiling contentedly before drifting off to sleep. The next day was Saturday and I was woken up by her sucking my cock into her mouth and Fiona placing her mons over my face for a morning 69 session, she wasn't very good at blow jobs but I figured I could teach her and I soon had her on the boil. When she came she released my cock and screamed very loudly and I watched her arse and thighs wobble around my head, "I want to fuck you now," I told her and she eagerly turned around and held my cock in her hand and she dropped down onto me, my cock pierced her lower lips and soon we were bumping uglies. I pulled her down so her chest was rubbing mine and I was pushing up into her, I held her close and we kissed as she fucked, "I'm coming❤," she suddenly announced I felt that tingle in the end of my cock and said "so am I."
She grunted as she felt my seed flood her cunt and then shook uncontrollably as the orgasm washed over her body, I by now had pushed my cock in as far as it would go and then she kissed me hard as she came down from her orgasmic high. We kissed and cuddled before we both showered, she never had a joint shower before and was pleasantly surprised when I fingered her to another orgasm as I soaped her back.
-x-X-x-
So for the past 2 years we have been fucking whenever her husband is not around and I must say she is now a lot better at blow jobs as well.
My other favourite and semi regular partner is Cathy. Cathy is the MD's secretary at where I work, I first slept with her on her 50th birthday when her husband didn't turn up to take her to dinner, if nothing else I am an opportunist and opportunity certainly knocked for me that night.
Cathy is just over 5ft 8 inches tall and is a UK clothes size 8, I found out she wears a D cup bra and has dyed brown hair, she had a cute face and her facial features remind me of Helen Mirren. She always dresses immaculately and has a reputation of a bit of guard dog for the MD. I first met her when she logged a call for a problem with her email and managed to sort it out and engaged her in conversation, I found out she was married and had twin boys who were both at university, she was open and friendly towards me but the other engineers were scared of her so I ended up taking all her calls.
Over the next few months we talked and I found out it was her 50th birthday a few days in advance so arranged to pop by and wish her a happy birthday, the MD wasn't in so she was sitting in his office and beckoned me in, I kissed her on the cheek and wished her a happy birthday and passed her a single rose which she took and kissed me on the cheek back. She didn't look very happy though and when I asked her what was wrong she spat out "My bloody husband can't be bothered to make sure he gets back for my special birthday so I will be on my own this evening. He says he's working but I'm sure he's a got a younger bit of stuff somewhere."
"Well I'm not doing anything so I can be your younger bit of stuff and I will take you out for a meal if you want," I offered.
She smiled and said "thank you it is so nice to meet a decent young man so I accept❤."
"Excellent, I'll come and pick you up at 7pm this evening, give me your home address and dress smartly as we'll be going somewhere nice," I replied.
She clapped her hands and then wrote her address on a piece of paper and passed it to me and said "Don't be late."
I arrived at exactly 7 o'clock and rang the doorbell to her house. She answered the door wearing a see through white blouse with a white camisole top on underneath, on her bottom half she had on a black pair of trousers that fitted her just so, I presented her with another rose and said "wow, look at you, if I didn't know any better I would think you were hoping to get lucky tonight."
She giggled like a teenager and said "I'm hungry let's go and eat and looped her arm through mine as we walked to my car." We chatted as drove to the Italian restaurant I knew and the meal was very good and as I was driving she had most of the wine to herself, this seemed to loosen her inhibitions and on the way home she rested her hand on my leg and said "Thank you, that was a perfect way to spend my birthday, now would you like to come in for a coffee to finish the evening off❤."
We pulled up outside her house and I took her up on her invitation for coffee and followed her into her house, we stood in her hallway and I took the bull by the horns and kissed her gently on her lips, she returned the kiss gently and stroked my arm, I wrapped an arm around her waist and held her close as the kisses became more passionate until we were sharing tongues, she led me I into her lounge and pushed me onto the sofa and then straddled me and kissed me on the lips, I undone the buttons on her blouse and she helped me remove it from her arms and shoulders, she didn't object when I pulled the straps of her camisole off her shoulders and pulled it down o her breast were now free, she pulled away and she removed my shirt and stood up and held out her hand, "my bedroom now❤," she commanded.
We walked upstairs to her room where we both stripped naked before falling onto the bed, for the next 10 minutes we kissed and touched each other all over, her skin was soft and she had a bit more meat on her than either Cynthia or Fiona and then she said "lay on your back❤."
I lay down on the bed with my head on the pillow and she straddled my face, I knew what she wanted and as it was her birthday who was I to disappoint her. I licked and kissed and sucked her lower lips and lit until she had a crashing orgasm and then did it again until she lost all her strength and collapsed on top of me, I rolled her over and lay on top of her and guided my cock into her tunnel, either her husband had a very small dick or she hadn't been shagged in years, she was so tight and it took a while to feed all of me inside her. Once we fully joined she just whispered "Go slow it's been quite a while❤," as I slowly shafted my cock in and out of her, she whimpered and made a grunting noise so I stopped but she said "don't stop please❤, just be slow and gentle❤."
For the next few minutes we slowly rocked ourselves together as we kissed and then it felt like my cock was no longer being held in a vice and things moved easier, she wrapped her arms around me and said "faster please❤," and I felt her legs go into the air and I seemed to sink deeper inside her on my down thrust, she started to shake and then she came with a cry of "Oh my god❤, I'm coming on your gorgeous cock❤."
I felt me cock being bathed in warm liquid so I went even faster and soon she was egging me on, I was now hammering into her and she moaned and came again quickly before I felt the tingle and know I wouldn't be long before I painted her insides, I sped up even more and she knew what it meant as she breathlessly whispered "I want to feel you spurt in me❤" so I did, I coated her insides with my hot sticky seed and she held me close and kept whispering "that feels wonderful❤" over and over again.
We lay locked together for a little while until I whispered "Happy Birthday," in her ear which prompted a laugh and then she realised I had not gone soft, there was something about this 50 years old wife, mother of 2 and grandmother of 1 that kept my attention as started to pump in and out of her slowly again, her hair was a mess and her makeup smudged but she was hot to trot as se moved her hips in time with mine, "What do you want?" I asked.
"Your cock❤," she replied.
"How?" I asked as our hips moved in unison.
"Deep inside my neglected pussy❤" she said.
So I kissed her and this time we fucked ourselves stupid, it seems I had burst her dam and she was determined to enjoy it. I left at 6 in the morning and was tired the next day as I had got very little sleep.
I got a call to see her in the morning for her printer and she was her normal playful yet professional self at work but emailed me later that day and it read:
"Dear Steve,
Are you free Wednesday next week as my husband is away and I would like for you to come round to my place and work on my muscle tone, there are a few new exercises that I would like to try and would gratefully appreciate your assistance.
Thanks in advance
Cathy Dobson."
I thought about a suitable reply and eventually came up with this:
"Dear Cathy,
I would be honoured to be your exercise partner but I warn you the exercises I have in mind could possibly take a few hours and will leave you feeling out of breath and could make you perspire, there are also special clothing requirements please see link below (I inserted a link to the Ann summers website).
Kind Regards
Steve."
Steve's adventures will continue shortly.