Even more really hot early sexual adventures xxx
The sexy hot summer of 62 continued unabated, in fact it got even hotter, if that was at all possible, certainly sex wise!! My Sunday evening visits to Ron and auntie Mary’s house no longer included a nice Sunday roast but did involve regular visits to the local red light area, me sometimes dressing up as a whore or something along those lines and always making sure that auntie Mary’s new found insatiable appetite for casual sex was satisfied.
I suppose we went down to the red light area, probably another dozen times, or so, that summer and I loved every single visit. It was however becoming very obvious that, and I wasn’t complaining, our visits were being driven by auntie Mary’s lust for sex. I’d normally get to Ron and Mary’s house about seven o’clock in the evening and Mary would be either already dressed in her ‘whores’ outfit or just finishing getting ready. Her outfits were becoming more and more ‘tartish’ if that’s the right word. I’d known auntie Mary, ever since I’d been ‘offered’ to her brother Ron by mr Vaughn for sex, about four or five years earlier and the change in her was amazing. She’d gone from a nice fairly frumpy middle aged spinster, who was at Ron’s beck and call and erstwhile sexual assistant, to a confident, assured rather attractive good looking woman and, from what I could see, determined to make up for lost time!!
I have to say that she always looked the part, that’s if you wanted to look like, a well used slightly older prostitute on the game. Mary was attractive rather than pretty and didn’t have to a bad figure, her tits were a bit too large for her body but with a nice half cup balcony bra they perked up nicely, her legs were good too and with the sort of high heeled stilettos she was now wearing showed them off to perfection. When I’d first met Mary I’m pretty sure that, apart from a bit of foundation, she didn’t wear any makeup at all but now it was bright red lipstick, rouge, red nails and she’d even started dying her hair lighter, not peroxide blond but very nearly. Her clothes too were totally different as well, even around the house, with short skirts and dresses (even shorter, ridiculously so, on our trips out!), skimpy tops (see through sometimes) and the ubiquitous stockings and suspenders with the straps and tops on show.
Of course I wasn’t left out and as Mary and I were both about the same height and size, body wise, I got to wear a lot of Mary’s clothes too. I absolutely loved it when we got dressed together in her bedroom, especially when she’d suggest I wear a particular dress or skirt and help me on with it, adjusting it to fit and making me twirl around showing it off, I just loved that!!! I loved it too when she’d help me with my stockings, suspenders, tucking my cock in my knickers and fitting my favourite pink bra, it was all just magical. Of course I’d help her too, sometimes applying her makeup (got quite good at that) and generally just being girly together xx
I didn’t always dress as I actually preferred and quite liked being in the car with Ron and watching the girls ply their trade and especially watching Mary as she stood on the corner. We’d invariably both get our cocks out as soon as Mary had got out the car and I think we both enjoyed wanking each other while we watched Mary and the other prostitutes. For an older guy, he had a really nice clean cock (they weren’t always clean or nice!!), was big girth wise, longish with a huge purple knob end and he could be wanked off and sucked for ages before he spunked but when he did, gosh, he cum absolutely loads!! While Mary was out of the car looking for punters we’d have some interesting chats and I was always probing him about his sex adventures, his relationship with Mary and on one occasion whether he fancied any of the prostitutes we were wanking over. He’d apparently been with a few, in the past, but it wasn’t his scene and he much preferred young boys like myself although one night, when I was with him,he did nearly get tempted by a quite young slim girl wearing a very pair of very tight, extremely short and revealing blue satin hot pants. I think it was more the fact she looked a bit ‘boyish’ that did it for him plus her short cropped hair, flat chest and white knee socks and before he could talk to her he’d spunked his load over me!!!
The other nice bit about being with Ron was that he knew the sort of prostitutes I enjoyed looking at and wanking over and we’d drive around wanking each other off while Mary was doing her thing, getting her brains fucked out. I just loved the really tarty looking ones who dressed in obscenely whorey outfits, tartier the better for me, I wasn’t very worried about their ages although I was always looking out for the young one I’d seen on my first night with Barry. As it was the summer months most of the girls didn’t wear much anyway and the mini skirts and dresses got shorter and shorter and the tops flimsier and flimsier, stockings, in the main, being replaced by fake tanned long legs. We were almost part of the scene and quite a few of the girls knew that we were connected, in some way, with Mary, who was making quite a name for herself, not all good. Apparently the girls always agreed a price before getting in a car and certainly before sex whereas Mary sometimes forgot to ask them even after she’d been fucked!! Anyway both Ron and I had our favourites who, if we saw them, would make a beeline for. Ron’s favourite was a very tall blond Swedish looking woman, probably about thirty, who had legs you could only dream of and usually wore a leopard print micro mini dress that barely covered her tiny black thong and when she sidled up to the car window and bent over her tight thong was a joy to behold. She cottoned on to Ron eventually but not before he’d got her to give him a quick wank through the car window and Ron had promptly spunked over her hand. He must have planned that as he could literally spunk to order.
One night, when I wasn’t with Mary, he offered to pay for me to have one if I wanted. I didn’t take too long to make my decision and before long we were going up one street and down another with me looking at all the girls in a different light. I finally decided I’d go for a girl I’d seen a few times before, young, probably only about eighteen, very pretty, quite dark skinned, bit of Indian I should imagine, but what did it for me was she was all in black leather for head to toe. As with the majority of the girls her soft leather mini skirt barely covered much at all and the bustier top enhanced her beautiful pert breasts and all finished off with a pair of black leather knee length stiletto boots, she was a stunner. We, well Ron actually, agreed a price with her and Ron drove the three of us to a spot we knew Mary had used before and Ron got out, going for a walk around the block, while we got down to business. It wasn’t as if I was a beginner in the sex stakes but it was the first time I’d actually been with a real prostitute, for sex anyway but luckily, despite her young years, she knew how to give her a good fuck. Just as I imagined it would be, we did it up against a wall, with her just pulling her thong to one side while I slipped my durex sheathed cock into her, surprisingly pert but moist cunt. I didn’t let the side down but I didn’t last as long as I should have but I’m sure the occasion got the better of me. She seemed pleased anyway and I certainly was. We’d just dropped her off before Mary came back, smiling, satisfied with her evenings business.
You have to remember that back then cross dressing and dressing up as a woman was only for the Danny la Rues of this world on tv and not as accepted as it is today, well certainly a lot more accepted than back then so I was definitely the exception to the rule when Mary took me with her onto those street corners dressed as a whore!! I was lucky that, well I like think so, that with my slim frame, good legs, Mary’s excellent makeup I could just about get away with it although I can absolutely assure you that I was bricking it the entire time I was with her!!! I probably went with her, dressed, only about five or six times, altogether, always being introduced as her daughter or a friend and most times just watching although if they asked I’d suck the punters cock before they fucked auntie Mary while I watched on intently. I found it really hard to get my head around how she touted herself for business, acted so sure of herself and was totally addicted to sex. She did have a bit of a penchant for younger Asian guys and one night we went, well she did, with four or five, all within about two hours, two of them fucking her in turns for about thirty minutes or more and she lapped it up. She never asked any of them to wear a rubber, she didn’t seem mind if they did or didn’t, only that they gave her a good fucking and dumped plenty of cum into her gaping hairy pussy. I queried Ron, when we were alone, about Mary and their relationship and it turned out that they actually had full sex quite often, which surprised me, but even more often since we’d started going down to the red light area and she’d stared dressing provocatively. He admitted to me that he was getting a bit concerned for her insomuch as that she’d started demanding that he take her down there on other evenings besides the Sunday nights when I came around.
If I remember rightly it was probably the last night I went dressed with her to the red light area, the pair of us got picked up by a well built black guy. He actually wanted me but, as usual, auntie Mary explained the setup and he seemed happy to fuck her instead, Mary throwing in a blow job from me to seal the deal!!! Good of her!! Mary’s dress ‘code’ had got really extreme in the ‘looking like a total whore’ style. That night she’d worn her usual sheer black stockings, suspenders and high heels but whereas her skirt usually made at least a stab at some degree of decency it didn’t seem to apply that evening and was nothing more than a thick belt rather than a skirt and thinking about it now, I’m not sure she was wearing her usual skimpy knickers either!! She topped it off with a totally see through black blouse and much much more makeup than usual. Me, well I was just a side show compared to Mary but she’d not held back, dressing me, and like her in black stockings, a pair of her white stilettos, a black pleated school girl skirt (Rob liked me to suck him off in that!!) and a white blouse.
He really was a big guy in every way, very muscular and toned, and when I got down in front of him and got his cock out I was pretty shocked I can tell you. Over my formative years I must have wanked and sucked hundreds of cocks, big ones, tiny ones, long, short, white, black, smelly and sweet but this one took the biscuit size wise, even semi hard it was huge and once I started sucking it, it grew to enormous proportions making it almost impossible for me to take even a couple of inches in my mouth, satisfying him and myself by just licking and sucking his large pink knob end. I could see Mary’s eyes agog, practically licking her lips in anticipation of taking his cock, of which I was sure she’d love and and take with ease and had already hitched her apology for a skirt up around her waist, her hands pulling the lips of her cunt apart as she lent against the factory wall ready for him, the perfect filthy whore she’d now become!! I’d like to think I was giving him a lot of pleasure as he seemed reluctant to leave me and once again asked Mary if he could have me but once again she refused. Thank god!!! Anyway she took him like the good ‘whore’ she now was and the pair of them gave as good as they received, he thrusting his rampant rock hard cock into her with an almost venomous intensity and Mary moaning and pulling him into and onto herself seemingly scared to miss a single inch of his long cock. Eventually he cum, his cock spunking into her cunt then pulling it out and draining the rest of his thick white cream over her belly, hairy cunt and stockinged legs. I must say that it was the most intense fuck between a man and a woman that I’d seem up until then and both of them were completely drained both physicality and, in Mary’s case, emotionally too, she certainly looked her advanced years after that fuck.
After they’d both regained their composure the three of us, in his car, went back to where Ron was parked, got talking and Errol, that was his name, I’m pretty sure, invited us both to a private members club on Brunswick square the following week for a ‘special’ back room ‘party’ with a few friends which Mary, obviously, immediately accepted but I had my reservations as Errol was definitely still under the impression that I was Mary’s daughter!!!! Mary was full of it that night and, as had had happened on most evenings I’d accompanied Mary dressed, Ron wanted sucking off (obviously wearing my schoolgirl attire, and always a pleasure) and when we got home Mary needed yet another fucking by myself. I must confess I was a bit turned on with the thought that Mary had had that huge cock up her and there I was giving her, hopefully as much pleasure on her living room floor!!!
That turned out to be the last time I went with Ron and Mary to the red light area but did I go to the party, did Mary go? Why was it the last time? Quite a few questions but, don’t worry, I will be telling all xxxx soon.
I suppose we went down to the red light area, probably another dozen times, or so, that summer and I loved every single visit. It was however becoming very obvious that, and I wasn’t complaining, our visits were being driven by auntie Mary’s lust for sex. I’d normally get to Ron and Mary’s house about seven o’clock in the evening and Mary would be either already dressed in her ‘whores’ outfit or just finishing getting ready. Her outfits were becoming more and more ‘tartish’ if that’s the right word. I’d known auntie Mary, ever since I’d been ‘offered’ to her brother Ron by mr Vaughn for sex, about four or five years earlier and the change in her was amazing. She’d gone from a nice fairly frumpy middle aged spinster, who was at Ron’s beck and call and erstwhile sexual assistant, to a confident, assured rather attractive good looking woman and, from what I could see, determined to make up for lost time!!
I have to say that she always looked the part, that’s if you wanted to look like, a well used slightly older prostitute on the game. Mary was attractive rather than pretty and didn’t have to a bad figure, her tits were a bit too large for her body but with a nice half cup balcony bra they perked up nicely, her legs were good too and with the sort of high heeled stilettos she was now wearing showed them off to perfection. When I’d first met Mary I’m pretty sure that, apart from a bit of foundation, she didn’t wear any makeup at all but now it was bright red lipstick, rouge, red nails and she’d even started dying her hair lighter, not peroxide blond but very nearly. Her clothes too were totally different as well, even around the house, with short skirts and dresses (even shorter, ridiculously so, on our trips out!), skimpy tops (see through sometimes) and the ubiquitous stockings and suspenders with the straps and tops on show.
Of course I wasn’t left out and as Mary and I were both about the same height and size, body wise, I got to wear a lot of Mary’s clothes too. I absolutely loved it when we got dressed together in her bedroom, especially when she’d suggest I wear a particular dress or skirt and help me on with it, adjusting it to fit and making me twirl around showing it off, I just loved that!!! I loved it too when she’d help me with my stockings, suspenders, tucking my cock in my knickers and fitting my favourite pink bra, it was all just magical. Of course I’d help her too, sometimes applying her makeup (got quite good at that) and generally just being girly together xx
I didn’t always dress as I actually preferred and quite liked being in the car with Ron and watching the girls ply their trade and especially watching Mary as she stood on the corner. We’d invariably both get our cocks out as soon as Mary had got out the car and I think we both enjoyed wanking each other while we watched Mary and the other prostitutes. For an older guy, he had a really nice clean cock (they weren’t always clean or nice!!), was big girth wise, longish with a huge purple knob end and he could be wanked off and sucked for ages before he spunked but when he did, gosh, he cum absolutely loads!! While Mary was out of the car looking for punters we’d have some interesting chats and I was always probing him about his sex adventures, his relationship with Mary and on one occasion whether he fancied any of the prostitutes we were wanking over. He’d apparently been with a few, in the past, but it wasn’t his scene and he much preferred young boys like myself although one night, when I was with him,he did nearly get tempted by a quite young slim girl wearing a very pair of very tight, extremely short and revealing blue satin hot pants. I think it was more the fact she looked a bit ‘boyish’ that did it for him plus her short cropped hair, flat chest and white knee socks and before he could talk to her he’d spunked his load over me!!!
The other nice bit about being with Ron was that he knew the sort of prostitutes I enjoyed looking at and wanking over and we’d drive around wanking each other off while Mary was doing her thing, getting her brains fucked out. I just loved the really tarty looking ones who dressed in obscenely whorey outfits, tartier the better for me, I wasn’t very worried about their ages although I was always looking out for the young one I’d seen on my first night with Barry. As it was the summer months most of the girls didn’t wear much anyway and the mini skirts and dresses got shorter and shorter and the tops flimsier and flimsier, stockings, in the main, being replaced by fake tanned long legs. We were almost part of the scene and quite a few of the girls knew that we were connected, in some way, with Mary, who was making quite a name for herself, not all good. Apparently the girls always agreed a price before getting in a car and certainly before sex whereas Mary sometimes forgot to ask them even after she’d been fucked!! Anyway both Ron and I had our favourites who, if we saw them, would make a beeline for. Ron’s favourite was a very tall blond Swedish looking woman, probably about thirty, who had legs you could only dream of and usually wore a leopard print micro mini dress that barely covered her tiny black thong and when she sidled up to the car window and bent over her tight thong was a joy to behold. She cottoned on to Ron eventually but not before he’d got her to give him a quick wank through the car window and Ron had promptly spunked over her hand. He must have planned that as he could literally spunk to order.
One night, when I wasn’t with Mary, he offered to pay for me to have one if I wanted. I didn’t take too long to make my decision and before long we were going up one street and down another with me looking at all the girls in a different light. I finally decided I’d go for a girl I’d seen a few times before, young, probably only about eighteen, very pretty, quite dark skinned, bit of Indian I should imagine, but what did it for me was she was all in black leather for head to toe. As with the majority of the girls her soft leather mini skirt barely covered much at all and the bustier top enhanced her beautiful pert breasts and all finished off with a pair of black leather knee length stiletto boots, she was a stunner. We, well Ron actually, agreed a price with her and Ron drove the three of us to a spot we knew Mary had used before and Ron got out, going for a walk around the block, while we got down to business. It wasn’t as if I was a beginner in the sex stakes but it was the first time I’d actually been with a real prostitute, for sex anyway but luckily, despite her young years, she knew how to give her a good fuck. Just as I imagined it would be, we did it up against a wall, with her just pulling her thong to one side while I slipped my durex sheathed cock into her, surprisingly pert but moist cunt. I didn’t let the side down but I didn’t last as long as I should have but I’m sure the occasion got the better of me. She seemed pleased anyway and I certainly was. We’d just dropped her off before Mary came back, smiling, satisfied with her evenings business.
You have to remember that back then cross dressing and dressing up as a woman was only for the Danny la Rues of this world on tv and not as accepted as it is today, well certainly a lot more accepted than back then so I was definitely the exception to the rule when Mary took me with her onto those street corners dressed as a whore!! I was lucky that, well I like think so, that with my slim frame, good legs, Mary’s excellent makeup I could just about get away with it although I can absolutely assure you that I was bricking it the entire time I was with her!!! I probably went with her, dressed, only about five or six times, altogether, always being introduced as her daughter or a friend and most times just watching although if they asked I’d suck the punters cock before they fucked auntie Mary while I watched on intently. I found it really hard to get my head around how she touted herself for business, acted so sure of herself and was totally addicted to sex. She did have a bit of a penchant for younger Asian guys and one night we went, well she did, with four or five, all within about two hours, two of them fucking her in turns for about thirty minutes or more and she lapped it up. She never asked any of them to wear a rubber, she didn’t seem mind if they did or didn’t, only that they gave her a good fucking and dumped plenty of cum into her gaping hairy pussy. I queried Ron, when we were alone, about Mary and their relationship and it turned out that they actually had full sex quite often, which surprised me, but even more often since we’d started going down to the red light area and she’d stared dressing provocatively. He admitted to me that he was getting a bit concerned for her insomuch as that she’d started demanding that he take her down there on other evenings besides the Sunday nights when I came around.
If I remember rightly it was probably the last night I went dressed with her to the red light area, the pair of us got picked up by a well built black guy. He actually wanted me but, as usual, auntie Mary explained the setup and he seemed happy to fuck her instead, Mary throwing in a blow job from me to seal the deal!!! Good of her!! Mary’s dress ‘code’ had got really extreme in the ‘looking like a total whore’ style. That night she’d worn her usual sheer black stockings, suspenders and high heels but whereas her skirt usually made at least a stab at some degree of decency it didn’t seem to apply that evening and was nothing more than a thick belt rather than a skirt and thinking about it now, I’m not sure she was wearing her usual skimpy knickers either!! She topped it off with a totally see through black blouse and much much more makeup than usual. Me, well I was just a side show compared to Mary but she’d not held back, dressing me, and like her in black stockings, a pair of her white stilettos, a black pleated school girl skirt (Rob liked me to suck him off in that!!) and a white blouse.
He really was a big guy in every way, very muscular and toned, and when I got down in front of him and got his cock out I was pretty shocked I can tell you. Over my formative years I must have wanked and sucked hundreds of cocks, big ones, tiny ones, long, short, white, black, smelly and sweet but this one took the biscuit size wise, even semi hard it was huge and once I started sucking it, it grew to enormous proportions making it almost impossible for me to take even a couple of inches in my mouth, satisfying him and myself by just licking and sucking his large pink knob end. I could see Mary’s eyes agog, practically licking her lips in anticipation of taking his cock, of which I was sure she’d love and and take with ease and had already hitched her apology for a skirt up around her waist, her hands pulling the lips of her cunt apart as she lent against the factory wall ready for him, the perfect filthy whore she’d now become!! I’d like to think I was giving him a lot of pleasure as he seemed reluctant to leave me and once again asked Mary if he could have me but once again she refused. Thank god!!! Anyway she took him like the good ‘whore’ she now was and the pair of them gave as good as they received, he thrusting his rampant rock hard cock into her with an almost venomous intensity and Mary moaning and pulling him into and onto herself seemingly scared to miss a single inch of his long cock. Eventually he cum, his cock spunking into her cunt then pulling it out and draining the rest of his thick white cream over her belly, hairy cunt and stockinged legs. I must say that it was the most intense fuck between a man and a woman that I’d seem up until then and both of them were completely drained both physicality and, in Mary’s case, emotionally too, she certainly looked her advanced years after that fuck.
After they’d both regained their composure the three of us, in his car, went back to where Ron was parked, got talking and Errol, that was his name, I’m pretty sure, invited us both to a private members club on Brunswick square the following week for a ‘special’ back room ‘party’ with a few friends which Mary, obviously, immediately accepted but I had my reservations as Errol was definitely still under the impression that I was Mary’s daughter!!!! Mary was full of it that night and, as had had happened on most evenings I’d accompanied Mary dressed, Ron wanted sucking off (obviously wearing my schoolgirl attire, and always a pleasure) and when we got home Mary needed yet another fucking by myself. I must confess I was a bit turned on with the thought that Mary had had that huge cock up her and there I was giving her, hopefully as much pleasure on her living room floor!!!
That turned out to be the last time I went with Ron and Mary to the red light area but did I go to the party, did Mary go? Why was it the last time? Quite a few questions but, don’t worry, I will be telling all xxxx soon.
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