Favourite wank fantasy number 2. Tracey Middlemass
A few years back I worked with a lady who reminded me very strongly of the softcore model Tracey Middlemass (search for Tracey on this site to take a look). Her name was Sheryl. She was about 50 at the time. Tracey was modelling in the early/mid 80s. So she would have been about Sherylâs age at this time. Sheryl had very similar features to Tracey. And the same shapely figure and big tits. She often wore tight jeans to work and they would stretch pleasingly across her ample bum. I never for one moment thought Sheryl was actually Tracey. But the similarities were striking.
I got quite close to Sheryl during our time working together. We spent breaks together and had the occasional lunch out of the office. Nothing ever happened between us. Though I still wonder how she might have reacted if I had tried something on. I do believe she might have been okay with it. I certainly found her very attractive. And the object of many an enjoyable wank.
My favourite fantasy had Sheryl admitting to me that she had done some modelling for top shelf magazines when younger. She was in fact Tracey. She asked if I would like to see one of her sets. Of course I told her that I would. She suggested I come round her house after work to have a look at a copy of Mayfair that she was in. I knew her husband was a lorry driver, working nights. So he wouldnât be around (this was actually true. Sherylâs husband John was an HGV driver. And he did work odd hours. And had regular nights away).
So I rocked up at her house that evening. Sheryl opened the door. She had on her tight jeans and a plain white blouse. It was unbuttoned just enough to show off a bit of fine looking cleavage. I thought she had made her face up since leaving work. She was looking pretty hot.
She showed me through to the living room and told me to take a seat on the sofa. She crossed to a dresser standing up against one wall, opened a drawer and took out a magazine. She came over and sat beside me. She was very close, her thigh pressed up against mine. She smelled nice. I realised she must have had a shower and applied some perfume since getting home. She placed the magazine in my lap. It was an old, well thumbed copy of Mayfair. She lent over me and began to turn the pages. I was very aware that her hand was a matter of inches away from my groin. I felt my cock begin to stiffen.
Sheryl sat back. The magazine was open in front of me. The pictorial was headed âTraceyâ. The pictures were clearly of a much younger Sheryl. In the first one she was pictured from the waist up, wearing only a bra. In the second she was in a silky shift. She was pulling it up to show off her stockings and suspenders. A hint of dark bush was just visible. In the third the straps of her shift were down around her upper arms and her big, gorgeous tits had tumbled out.
âThatâs me as a twenty year old. What do you think?â.
I mumbled something inadequate about how nice she looked. She was leaning across me to get a look at the pictures. One of her big boobs was squashed up against my upper arm and her thigh was pressed up hard against mine. My cock continued to swell and there was now a bulge in my trousers which Sheryl couldnât have failed to notice as she looked at the magazine in my lap.
I turned the page. There was a full page shot of Tracey/Sheryl naked save for her stockings and suspenders with her back to the camera. Her bum looked wonderful. I couldnât help but think how good it would be to shoot my load over those cheeks. My length was immediately ramrod straight and positively straining against the cloth of my trousers. The picture on the opposite page was even better. Full frontal this time. With a naughty grin on her face, her big boobs thrust forward and her magnificent, dark bush framed by her stocking tops and suspenders.
Sheryl was grinning broadly. âYouâre hard arenât you?â, she whispered in my ear. âWhy donât you take your trousers off? Youâll be much more comfyâ.
I didnât need to be asked twice. I put the mag down and stood up. I unzipped my fly and pulled down my trousers and pants. I sat back down and put the magazine back in my lap, my fully erect cock now quivering over it.
Sheryl was staring at my hard member. âYou have a lovely cockâ, she said. âI should love to feel it in my pussy. But only John can fuck me. But I should be happy to touch you if you would likeâ.
I could only nod agreement. Sheryl immediately reached out and took my stiff member in her hand. Very gently and slowly she began to stroke my cock. She was whispering in my ear again. âYouâre so hard. Does that feel good? Do you like my pictures? Tell me what you would have done to me when I was young and hotâ.
I could barely talk. I was looking at the two full page pictures that showed her full frontal and with her back to the camera. Both were superb and I should happily have wanked over either. I managed to tell her that she was still hot and that I would love to fuck her now. The speed of her strokes increased a little as I spoke. She was getting into this. She gasped in delight as the angry red head of my cock popped out from my foreskin.
âYour pictures are amazingâ, I gasped. âI would love to have played with your big tits. I would have sucked on your nipples then got you to wrap your boobs round my cock for a tit wank. I would have cum all over your tits and watched you rub my jizz into your skin. I love your hairy bush. I would have gone down on you and licked your beautiful pussy. I would love to have fucked you doggy style. Iâd pull out just before coming to spunk all over your bumâŚ..â.
I couldnât take it any longer. Sheryl sensed this and bent her head down to my groin as my cock began to spasm. She took me in her mouth as the first jet of cum blasted from my cock. She sucked on me enthusiastically, happily swallowing my seed. Another shot followed. And another. Sheryl was sucking me dry. A dribble of cum ran down her chin. A final load of cum oozed from my cock. Sheryl gratefully swallowed it downâŚâŚ.
I got quite close to Sheryl during our time working together. We spent breaks together and had the occasional lunch out of the office. Nothing ever happened between us. Though I still wonder how she might have reacted if I had tried something on. I do believe she might have been okay with it. I certainly found her very attractive. And the object of many an enjoyable wank.
My favourite fantasy had Sheryl admitting to me that she had done some modelling for top shelf magazines when younger. She was in fact Tracey. She asked if I would like to see one of her sets. Of course I told her that I would. She suggested I come round her house after work to have a look at a copy of Mayfair that she was in. I knew her husband was a lorry driver, working nights. So he wouldnât be around (this was actually true. Sherylâs husband John was an HGV driver. And he did work odd hours. And had regular nights away).
So I rocked up at her house that evening. Sheryl opened the door. She had on her tight jeans and a plain white blouse. It was unbuttoned just enough to show off a bit of fine looking cleavage. I thought she had made her face up since leaving work. She was looking pretty hot.
She showed me through to the living room and told me to take a seat on the sofa. She crossed to a dresser standing up against one wall, opened a drawer and took out a magazine. She came over and sat beside me. She was very close, her thigh pressed up against mine. She smelled nice. I realised she must have had a shower and applied some perfume since getting home. She placed the magazine in my lap. It was an old, well thumbed copy of Mayfair. She lent over me and began to turn the pages. I was very aware that her hand was a matter of inches away from my groin. I felt my cock begin to stiffen.
Sheryl sat back. The magazine was open in front of me. The pictorial was headed âTraceyâ. The pictures were clearly of a much younger Sheryl. In the first one she was pictured from the waist up, wearing only a bra. In the second she was in a silky shift. She was pulling it up to show off her stockings and suspenders. A hint of dark bush was just visible. In the third the straps of her shift were down around her upper arms and her big, gorgeous tits had tumbled out.
âThatâs me as a twenty year old. What do you think?â.
I mumbled something inadequate about how nice she looked. She was leaning across me to get a look at the pictures. One of her big boobs was squashed up against my upper arm and her thigh was pressed up hard against mine. My cock continued to swell and there was now a bulge in my trousers which Sheryl couldnât have failed to notice as she looked at the magazine in my lap.
I turned the page. There was a full page shot of Tracey/Sheryl naked save for her stockings and suspenders with her back to the camera. Her bum looked wonderful. I couldnât help but think how good it would be to shoot my load over those cheeks. My length was immediately ramrod straight and positively straining against the cloth of my trousers. The picture on the opposite page was even better. Full frontal this time. With a naughty grin on her face, her big boobs thrust forward and her magnificent, dark bush framed by her stocking tops and suspenders.
Sheryl was grinning broadly. âYouâre hard arenât you?â, she whispered in my ear. âWhy donât you take your trousers off? Youâll be much more comfyâ.
I didnât need to be asked twice. I put the mag down and stood up. I unzipped my fly and pulled down my trousers and pants. I sat back down and put the magazine back in my lap, my fully erect cock now quivering over it.
Sheryl was staring at my hard member. âYou have a lovely cockâ, she said. âI should love to feel it in my pussy. But only John can fuck me. But I should be happy to touch you if you would likeâ.
I could only nod agreement. Sheryl immediately reached out and took my stiff member in her hand. Very gently and slowly she began to stroke my cock. She was whispering in my ear again. âYouâre so hard. Does that feel good? Do you like my pictures? Tell me what you would have done to me when I was young and hotâ.
I could barely talk. I was looking at the two full page pictures that showed her full frontal and with her back to the camera. Both were superb and I should happily have wanked over either. I managed to tell her that she was still hot and that I would love to fuck her now. The speed of her strokes increased a little as I spoke. She was getting into this. She gasped in delight as the angry red head of my cock popped out from my foreskin.
âYour pictures are amazingâ, I gasped. âI would love to have played with your big tits. I would have sucked on your nipples then got you to wrap your boobs round my cock for a tit wank. I would have cum all over your tits and watched you rub my jizz into your skin. I love your hairy bush. I would have gone down on you and licked your beautiful pussy. I would love to have fucked you doggy style. Iâd pull out just before coming to spunk all over your bumâŚ..â.
I couldnât take it any longer. Sheryl sensed this and bent her head down to my groin as my cock began to spasm. She took me in her mouth as the first jet of cum blasted from my cock. She sucked on me enthusiastically, happily swallowing my seed. Another shot followed. And another. Sheryl was sucking me dry. A dribble of cum ran down her chin. A final load of cum oozed from my cock. Sheryl gratefully swallowed it downâŚâŚ.
3 years ago