A sexy Crossdressing Affair
When I was in my early forties I started an elicit affair with a divorced woman called Sandra. We both worked for the same company and just after our affair started the company was taken over by a company in Leeds and relocated there. Several of the staff were needed to relocate the manufacturing process including Sandra and myself. We travelled to Leeds on a Monday and returned on a Friday.
Sandra was a very attractive woman in her late forties with a great figure and an insatiable lust for sex. She just oozed sex. Very soon in our relationship she discover that I was a 'closet' crossdresser and she didn't mind in the least and actually encouraged me. I'd pick Sandra up from her house early on a Monday morning and, usually, even before she'd got to the end of her road, she'd be undoing my trousers to get my cock out, taken off her knickers, that's if she was wearing any and putting my free hand and fingers up her pussy. Before we got to the motorway she'd usually sucked me off and she'd had her first orgasm. We always stopped again just past Mansfield in a secluded lane and she either wank me off again or if the weather was ok we'd get out the car and I'd fuck her up against the car or over the bonnet. I think the record for the day was four wanking sessions for me and nearly ten orgasms or fucks for Sandra. She really did like sex.
The company was very generous and put us up at a very nice hotel in the centre of Leeds and which also had a underground car park. I also have a 'kink' for prostitutes, it's just how they dress sexily and how they are used and before long Sandra found out about this side of me too and, like I knew she would, joined in the fun. Once or twice a week we'd venture out to the red light area in Leeds around Chapletown and also the red light area in Bradford. We'd cruise around with me looking at the girls whilst Sandra wanked me off. Sometimes she would insist that I dress as a whore and that's when the underground car park came in handy as I could slip out dressed quit easily. Most of the time she just wanked me as we drove around but a couple of times we'd stop to talk to one and as I was talking to her about how much she'd charge Sandra would try to bring me off in front of the girl.
There was a sex shop in Bradford and before we went cruising one night we went in the shop and bought a vibrator and a quite big dildo for her to use whist she was wanking me looking at the prostitutes. One of Sandra’s things was that she liked being fingered and brought off before I fucked her. Her cunt became very tight after she'd cum and she enjoyed me having to really force myself into her drying cunt. She often screamed with pain but she always told me afterwards that she enjoyed it that way. Apparently, when she was in her early years an uncle used to use her and when he fucked her with his big prick it used to give her pleasure and she never forgot it or the pleasure of him abusing her.
One night we'd gone out, me dressed, for one off our usual evenings jaunts and we'd ended up in the Leeds red light area. We'd gone past one particular girl a couple of times and Sandra could tell, from my throbbing prick, that I quite fancied her. She asked me if I fancied picking her up and, after some hesitation, I said yes so the next time we drove by we pulled over to her. She was, or looked,I thought no more than seventeen or eighteen, at the most but she might have been younger. She was dressed in a very short red plastic mini shirt, a cropped top and very high heels. She was obviously very surprised when she looked in the car and saw me dressed, cock exposed and Sandra gently wanking me. I think at first she was a bit wary but after some reassuring words from Sandra she got in the back seat. We drove to a builders yard that she explained was quite safe. It was very quiet and a warm summer night so we got out the car. The young prostitute lent back against the car and pulled down her knickers. She had a beautiful tanned body and thinking on it now, must have been as the hair on her pussy was very soft and fine. Sandra told the girl to wank me, which she did while I kissed Sandra. The young girl then got out a durex and rolled it onto my, by now, very large and throbbing prick. I wasn't going to last long. I started to fuck her but she was quite tight for a prostitute but all the while Sandra was rubbing her pussy like mad and after only a couple of minutes, if that, she demanded that I start fucking her. She'd orgasmed by now, so as usual, was quite tight. The young girl held the lips of her cunt apart, pulled the rubber off and guided me into her. I cum almost immediately and soon the spunk was running down Sandra’s thighs. The young girl commented that she'd not seen anything like this before and what a hot couple we were. I'd agree with that.
Another time she arranged to meet me, not in Leeds but back in our home town, late one night in our local red light area. I turned up dressed as 'ordered' looking, as usual like a tart. I parked up and sure enough Sandra pulled up shortly afterwards she gestured that I should get out the car and come to her. At first I didn't want to for obvious reasons but soon relented and, on my very high heels, tottered towards her car. The street was reasonably busy with a few girls on the various street corners and a few punters driving by. When I got to her car she told me to go to the end of the street, stand on a corner while she drove around the block before picking me up. Do it for me like a good whore, she told me.
We, I'm sure you can imagine, how nervous I was and also excited, at the same time but off I went as ordered as Sandra drove off. I was dressed much the same as I was when we had the encounter with the young prostitute in Leeds, wearing a very short black leather mini, a see though blouse, black holdups and sky high red patent heels so I was pretty 'obvious'. It wasn't far to the street corner, thank goodness but by the time I got there one car had already pulled up along side me. His window came down and a young Asian guy, about twenty asked me 'How much?'. Well I was pretty speechless and was about to start having a conversation when I saw Sandras car coming down the street. I made my excuses and quickly got in her car, very excited but also quite relived. Sandra was wearing a white trench coat but I could see that she was wearing her trade mark black stockings and high heels. We drove off to a more quiet area but still very run down and parked at the end of a dark alley, lit only by a nearby street lamp. Barbara told me to get out the car and led me up the alley where she opened her Mac to revel that she was only wearing a basque, stockings and heels. Well she was well fucked up against that wall having first fingered her to climax and the fucking her tight cunt xxx
We were at it night and day and on one occasion we were working late in the factory and we had sex on the board room table and another time in the gents toilets.
Our affair sort of petered out when the factory moved again to Scotland and as we weren't prepared to relocate that far we were made redundant. I did see her a few times afterwards either at her cottage or in the country lanes near where she lived. If I met her in the countryside I'd always dress and we'd have sex in the car or in summer, in a field. I remember once we went Ito one field that bordered on to the M4 motorway and she sucked me off, me in my whores outfit and her in just a bra and pants in full view of the passing (and speeding) motorway traffic. Probably wasn't the most sensible thing to do to encourage safe driving!!
On another of our meets we were down a quiet country lane when a cyclist came by and obviously spotted what we were up to and shortly after passing us came back to see more. Sandra didn't worry at all and demanded that I carry on going down on her and fingering her. The guy on the bike, after watching us for a few minutes looked around and downed his Lycra shorts and, still on his bike, started wanking while watching us, I have to say he had a huge cock and if he hadn't spunked so quickly I'm sure Sandra would have taken him. We had quite a few near misses, which included a jogger watching me cum, a girl on a horse and a farmer who got out of his combine harvester to watch as I fucked her up against a tree.
When I went to her cottage I always dressed, sometimes in her clothes but usually, as I enjoyed and she did too, as a slut. One night, quite late on, she took me to a local 'dogging' site although I think it was used mostly by courting couples. When we arrived there were three or four other cars s**ttered amongst the parking area and trees. As usual we stated doing our own thing and didn't take much notice of what was going on in the other cars, well I didn't anyway. We weren't there long before two guys appeared at the window both with their cocks out and started watching us. Well I was going down on Sandra so I didn't really notice them but Sandra wound down the window and while I was down licking her pussy she started wanking the two guys though the window. One of them soon spunked, most of it over Sandra’s face and the when I came up from her cunt she started wanking us both at the same time. We both cum much about the same time, Sandra getting another face full and me spunking all over her stockings. She loved it and wanted to do it again but it was soon after that that our affair finished and it never happened again. Still think very fondly of Sandra and our happy times..
Sandra was a very attractive woman in her late forties with a great figure and an insatiable lust for sex. She just oozed sex. Very soon in our relationship she discover that I was a 'closet' crossdresser and she didn't mind in the least and actually encouraged me. I'd pick Sandra up from her house early on a Monday morning and, usually, even before she'd got to the end of her road, she'd be undoing my trousers to get my cock out, taken off her knickers, that's if she was wearing any and putting my free hand and fingers up her pussy. Before we got to the motorway she'd usually sucked me off and she'd had her first orgasm. We always stopped again just past Mansfield in a secluded lane and she either wank me off again or if the weather was ok we'd get out the car and I'd fuck her up against the car or over the bonnet. I think the record for the day was four wanking sessions for me and nearly ten orgasms or fucks for Sandra. She really did like sex.
The company was very generous and put us up at a very nice hotel in the centre of Leeds and which also had a underground car park. I also have a 'kink' for prostitutes, it's just how they dress sexily and how they are used and before long Sandra found out about this side of me too and, like I knew she would, joined in the fun. Once or twice a week we'd venture out to the red light area in Leeds around Chapletown and also the red light area in Bradford. We'd cruise around with me looking at the girls whilst Sandra wanked me off. Sometimes she would insist that I dress as a whore and that's when the underground car park came in handy as I could slip out dressed quit easily. Most of the time she just wanked me as we drove around but a couple of times we'd stop to talk to one and as I was talking to her about how much she'd charge Sandra would try to bring me off in front of the girl.
There was a sex shop in Bradford and before we went cruising one night we went in the shop and bought a vibrator and a quite big dildo for her to use whist she was wanking me looking at the prostitutes. One of Sandra’s things was that she liked being fingered and brought off before I fucked her. Her cunt became very tight after she'd cum and she enjoyed me having to really force myself into her drying cunt. She often screamed with pain but she always told me afterwards that she enjoyed it that way. Apparently, when she was in her early years an uncle used to use her and when he fucked her with his big prick it used to give her pleasure and she never forgot it or the pleasure of him abusing her.
One night we'd gone out, me dressed, for one off our usual evenings jaunts and we'd ended up in the Leeds red light area. We'd gone past one particular girl a couple of times and Sandra could tell, from my throbbing prick, that I quite fancied her. She asked me if I fancied picking her up and, after some hesitation, I said yes so the next time we drove by we pulled over to her. She was, or looked,I thought no more than seventeen or eighteen, at the most but she might have been younger. She was dressed in a very short red plastic mini shirt, a cropped top and very high heels. She was obviously very surprised when she looked in the car and saw me dressed, cock exposed and Sandra gently wanking me. I think at first she was a bit wary but after some reassuring words from Sandra she got in the back seat. We drove to a builders yard that she explained was quite safe. It was very quiet and a warm summer night so we got out the car. The young prostitute lent back against the car and pulled down her knickers. She had a beautiful tanned body and thinking on it now, must have been as the hair on her pussy was very soft and fine. Sandra told the girl to wank me, which she did while I kissed Sandra. The young girl then got out a durex and rolled it onto my, by now, very large and throbbing prick. I wasn't going to last long. I started to fuck her but she was quite tight for a prostitute but all the while Sandra was rubbing her pussy like mad and after only a couple of minutes, if that, she demanded that I start fucking her. She'd orgasmed by now, so as usual, was quite tight. The young girl held the lips of her cunt apart, pulled the rubber off and guided me into her. I cum almost immediately and soon the spunk was running down Sandra’s thighs. The young girl commented that she'd not seen anything like this before and what a hot couple we were. I'd agree with that.
Another time she arranged to meet me, not in Leeds but back in our home town, late one night in our local red light area. I turned up dressed as 'ordered' looking, as usual like a tart. I parked up and sure enough Sandra pulled up shortly afterwards she gestured that I should get out the car and come to her. At first I didn't want to for obvious reasons but soon relented and, on my very high heels, tottered towards her car. The street was reasonably busy with a few girls on the various street corners and a few punters driving by. When I got to her car she told me to go to the end of the street, stand on a corner while she drove around the block before picking me up. Do it for me like a good whore, she told me.
We, I'm sure you can imagine, how nervous I was and also excited, at the same time but off I went as ordered as Sandra drove off. I was dressed much the same as I was when we had the encounter with the young prostitute in Leeds, wearing a very short black leather mini, a see though blouse, black holdups and sky high red patent heels so I was pretty 'obvious'. It wasn't far to the street corner, thank goodness but by the time I got there one car had already pulled up along side me. His window came down and a young Asian guy, about twenty asked me 'How much?'. Well I was pretty speechless and was about to start having a conversation when I saw Sandras car coming down the street. I made my excuses and quickly got in her car, very excited but also quite relived. Sandra was wearing a white trench coat but I could see that she was wearing her trade mark black stockings and high heels. We drove off to a more quiet area but still very run down and parked at the end of a dark alley, lit only by a nearby street lamp. Barbara told me to get out the car and led me up the alley where she opened her Mac to revel that she was only wearing a basque, stockings and heels. Well she was well fucked up against that wall having first fingered her to climax and the fucking her tight cunt xxx
We were at it night and day and on one occasion we were working late in the factory and we had sex on the board room table and another time in the gents toilets.
Our affair sort of petered out when the factory moved again to Scotland and as we weren't prepared to relocate that far we were made redundant. I did see her a few times afterwards either at her cottage or in the country lanes near where she lived. If I met her in the countryside I'd always dress and we'd have sex in the car or in summer, in a field. I remember once we went Ito one field that bordered on to the M4 motorway and she sucked me off, me in my whores outfit and her in just a bra and pants in full view of the passing (and speeding) motorway traffic. Probably wasn't the most sensible thing to do to encourage safe driving!!
On another of our meets we were down a quiet country lane when a cyclist came by and obviously spotted what we were up to and shortly after passing us came back to see more. Sandra didn't worry at all and demanded that I carry on going down on her and fingering her. The guy on the bike, after watching us for a few minutes looked around and downed his Lycra shorts and, still on his bike, started wanking while watching us, I have to say he had a huge cock and if he hadn't spunked so quickly I'm sure Sandra would have taken him. We had quite a few near misses, which included a jogger watching me cum, a girl on a horse and a farmer who got out of his combine harvester to watch as I fucked her up against a tree.
When I went to her cottage I always dressed, sometimes in her clothes but usually, as I enjoyed and she did too, as a slut. One night, quite late on, she took me to a local 'dogging' site although I think it was used mostly by courting couples. When we arrived there were three or four other cars s**ttered amongst the parking area and trees. As usual we stated doing our own thing and didn't take much notice of what was going on in the other cars, well I didn't anyway. We weren't there long before two guys appeared at the window both with their cocks out and started watching us. Well I was going down on Sandra so I didn't really notice them but Sandra wound down the window and while I was down licking her pussy she started wanking the two guys though the window. One of them soon spunked, most of it over Sandra’s face and the when I came up from her cunt she started wanking us both at the same time. We both cum much about the same time, Sandra getting another face full and me spunking all over her stockings. She loved it and wanted to do it again but it was soon after that that our affair finished and it never happened again. Still think very fondly of Sandra and our happy times..
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