It was the mid eighties and I had been married and divorced and went out with a number of women my age and younger in my bid to find a new partner, but my fantasy for older women was still strong. I met a lady whose name is Yvonne and who worked for me. I was a retail operations manager for a chain of retail outlets in the south of England. Yvonne worked in one of the stores, part-time, lived locally and I got to know her at work. She was divorced and lived with her son who was in his twenties. We chatted socially and she knew I was divorced. I was in my early thirties and I think she was in her mid fifties. She was interested in me and my life style and often asked me about my social and love life. We became quite friendly and had a common bond in that her manager was failing which she knew it as did I.
She was quite tall maybe 5 foot 7 or 8 and probably weighed about 180 to 190 pounds. She was heavily built – with wide bottom, large breasts big enough for me to have to use two hands to hold one. Her legs were stocky and her thighs quite thick to match her hips and bottom. Her hair was grey and quite straight, down to her shoulders. She was pretty and full of face and always looked and smelt lovely. She was always presentable, despite being on a low income. She was not a grandma but would pass as one.
When at her work she was often bending and crouching as she replenished the shelves and when carrying out her duties of administration. I often noticed her deep cleavage and more as she leaned forward and as she sat at her desk and often peeked up her skirt as she climbed ladders and crouched during her work. I always left that store with an erection.
Just in conversation one day I suggested that we go out one evening for a drink as we were both single and got on well and to my surprise she agreed. I had been having fantasies about her with her being big breasted and mature. As I said earlier I have a thing about older ladies.
I masturbated during the days leading up to our meeting and imagined her big bra and her breasts spilling out of it, her wide bottom and her large thighs. I wondered what her knickers were like. The culmination of my fantasy was her sitting on my erect penis facing me, with her grey tight skirt around her waist displaying her light tan stockings and white suspenders and her thick thighs, her breasts were naked as her bra had been discarded earlier, and they hung down swaying as she moved. This was all in my imagination as I had not been with a large mature lady before.
The day arrived and I waited in my car near to the store until she finished work at 9 pm on that Sunday night. We had to be discreet as we did not wish for our colleagues to know about our date.
I saw her leave the store and walk across the road towards my car casting a look over her shoulder to see if she was being watched. She looked good, her hair was tidy and she wore a tight grey skirt just below her knees, as usual, it was spring time and quite warm so she wore just a white buttoned blouse and a grey jacket on top. Her breasts stood out firmly as I viewed her profile and her bottom looked wide inside her tight skirt. Her legs looked like those of a younger woman. Was she wearing any leg wear? Maybe, I couldn't be sure, but I did like her red high heels.
I opened the car door from inside and she quickly got in. We exchanged greetings and I asked her what she wanted to do. "Let's go for a drink" she replied and I asked her if there was any where in particular she liked.
"Let's go out of town as we don't want to be seen by anyone who knows us, do we?" she suggested.
I looked at her and she smiled, her makeup was perfect, lovely red lipstick, she had made an effort to look good and she did. I glanced at her knees which were revealed as her tight skirt rode above them. She was wearing leg wear, light tan and shiny. I wondered if they were stockings or tights. Her blouse was buttoned up but revealing a hint of her lovely deep cleavage. We drove to a village pub where we got drinks and sat and chatted about our lives and work. She had a gin and tonic and I had a beer. After a while I asked what she wanted to do next and she said, "I would like to go to your place for a coffee." My heart beat rose and my mouth went dry, my mind was racing. She wants to come back to my apartment. That means she wants to be intimate with me. My word, I was so excited.
We left the pub and walked to my car, she smelt good as I held the car door open for her and I watched as she got into her seat. Her legs looked sexy as she swung them into the seat revealing a little thigh but in a lady-like fashion.
During the short drive I was conscious of her breasts right next me and the cleavage in view between the lapels of her blouse. She had undone one button when I wasn't looking and so I could see the beautiful soft curves of her breasts. We arrived at my apartment and I walked ahead of her to the bottom of the steps and then followed her upwards. I looked at her swaying bottom and we ascended to my fount door. I was wondering what type of knickers she was wearing.
I opened the door and she entered first. She removed her jacket and I placed it on a chair. She looked amazing in her tight skirt and tight white blouse. Her breasts were causing it to wrinkle it was so tight around her upper body. The buttons were straining to keep together and I could see a little of her bra which was pale grey in colour.
She sat on my sofa and I made us coffee. I asked if she wanted a drink but she did not. I placed the coffees on a table near to the sofa and sat next to her keeping my distance. Her skirt had risen well above her knees revealing her wonderful thick thighs and her blouse was bursting with her huge breasts sticking straight out in front of her. Her bra was doing its job well but the outline of her nipples was visible and they looked large and erect from where I was sitting. My cock, which was already firm and hardened and I had to adjust its position but discreetly.
I was nervous and so was she. As we chatted she licked her lips and I detected a quiver in her voice and there were some gaps in the conversation. What should I do?
I decided to go for it, so I moved closer to her and put my arm around her shoulders; she stiffened a little and took my hand as it rested on her right shoulder. I leaned in to her and kissed her on her bright red lips. There was no reaction so I kissed her again and lingered for longer this time. This time she turned towards me kissed back and squeezed my hand. I looked her in the eye and asked her if this was alright with her and she smiled and nodded "Yes, of course but don't expect too much."
I kissed her again and my lips parted and I pushed my tongue gently past her lips. She responded and opened her mouth. Our tongues met and caressed slowly and softly. She pushed back hard and so did I. She turned her body towards me and I felt her huge breasts against my chest. They were so firm inside her bra. We continued this embrace and the passionate kissing for a while until she pulled away and looked at me. Her face was glowing and so was her neck and chest. "Are you Ok John" she whispered huskily. "I haven't kissed a man like that for ten years. You are a great kisser".
I started again and while doing so knelt up on the sofa and embraced her and she followed my example by caressing my back and shoulders. Our bodies were pressed hard together as I felt all over her back. I could feel the middle age spread around her shoulders and her waist and the magnificence of her huge bra. The back band was at least three inches deep and there were five clips. She wanted to stand and so I let her and when she was up right we continued our embrace which became more passionate. I felt all over her upper body from her ear lobes over her wide fleshy back and down to her broad hips. I had never caressed a woman this size before or of this age. Her under wear fascinated me. I wanted to see her substantial bra and she appeared to be wearing some sort of corset and what about knickers, what would they be like?
My cock was bursting as it pressed against her belly. She pushed back which was the signal for me. She wanted it and I wanted her. My hands slipped to her large bottom. Her skirt was so tight across her bottom. I pulled her against me and then caressed all over the soft fleshy mounds, then to her hips and upper thighs. She was passionate; her tongue was feasting on mine. I went for her neck and her ear lobes and she threw her head back and I kissed and licked all over her neck and upper chest and as far down to her cleavage as I could. Her face and neck were flushed and she was panting.
I pulled away and started to undo the buttons on her blouse and she whispered into my ear "are you after my boobies?"
"Yes please, may I see them and touch them Yvonne, please. I am desperate to touch and caress and kiss and lick your wonderful breasts."
"I know you are and I am equally anxious to feel your young fingers and lips all over them," she replied.
The blouse was open to the waist band of her skirt and I tried to pull it out from inside her skirt and she helped me. I could see the massive grey half cup bra and the substantial shoulder straps. The blouse was fully open and now I pushed it slowly off her shoulders to reveal her fleshy upper body. Her upper arms; her whole upper chest was flushed with desire, her blouse fell onto the sofa and now to begin with, I felt her breasts through her bra. The material was quite course and firm but it would have to be to hold up those massive breasts. I squeezed her taught nipples and caressed the area which was exposed above her half bra cups.