Lisa Gets More Than She Bargained For
- 2 years ago
- 12
- 0
Crossdresser Gets More Than She Bargained For free porn video
My story is like many I have read on here and which I only fantasised about, till now. This story is all true, I thought about embellishing it to make it sexier but thought I’d let you know what happened just as it did. A short history of me and dressing up first.
I have been crossdressing for as long as I can remember, from sneaking a pair of my sisters panties, to even sneaking into the gardens of my parents neighbours and pinching underwear from washing lines. In my late teens when I found girls (and sex) I purged any clothing that I had and managed to put the ’urge’ behind me. I settled down got married etc. etc. Unfortunately for me (or not?) my wife like to wear very sexy underwear, stockings and very revealing outfits which meant there were a lot of these ‘things’ around the house. It started small, again, when on a day off I would be doing some washing and find myself holding the knickers against myself, then wearing them until before long I was back to a full ensemble masturbating furiously.
My wife soon found out what I was doing and, instead of disowning me like I thought she would, she said she understood and would help me out. Before long I had a drawer full of my own clothing and even a couple of pairs of 5 inch stiletto heels, one black pair and a pair of bright red Mary Janes , my favourite. The only stipulation she put on the arrangement was that I only dressed inside the house and if she was with me not in our bedroom, I obviously agreed.
This arrangement went on for quite a few years and to be honest it was all I ever wanted, whilst on a night out she would say to me “when we get home we’ll ‘get comfortable’” she knew this would get me going. I would proceed upstairs and dress in one of my many outfits and we would have the most amazing sex.
I have been a little vague up to now so as not to get the reader to aroused as this isn’t my main story just an insight as to what got me here. My story starts when my wife went away one weekend on a girls hen night, just before she left she whispered in my ear, whilst stroking my cock through my jeans, that if I dressed up tonight at ten o’clock sharp, she would go into the ladies wherever she was and stroke her clit thinking of me doing the same, I nearly came there and then.
Around eight o’clock I started to get ready although as I had been quite excited and had got everything laid out on the bed ready, I was showered and busting to get on with it. I was ready for about eight thirty, walking around the house, I kept walking up to the tall mirror in the bedroom looking at myself, I was quite happy with what I saw. I was wearing a red skater dress which just covered my thighs, I had on a very silky pair of red knickers, my stockings were natural, glossy hold ups with a very deep lace top and the heels had to be of course my five inch bright red Mary Janes, I put on my blonde shoulder length wig and did my make-up as best I could, this was one of the things my wife always did but I was getting better at it.
While I waited I got a little impatient and decided to do something that I had always wanted to, as it was dark outside I thought how naughty it would be to go for a quick drive, I had seen some youtube videos of Gurls walking in front of their cars down quiet lanes etc. I drove to a local industrial estate that as it was weekend would be deserted, I drove around for a short while before parking up at the end of a quiet street where they park the lorry trailers when not in use, what I didn’t know was not all of them were ‘not in use’ I set my camera rolling and started walking up and down in front of my car, stopping every now and then to adjust my stockings and pout at the camera when, to my sheer horror I saw a man standing, looking straight at me. I hadn’t seen him due to the glare of the headlights, schoolgirl error. I went to get into my car, shaking like a leaf, I opened the door and looked up one last time to see that he was near my car and smiling, I don’t know why I did it but I asked him if he’d ‘enjoyed the show’, I think it was now that he realised all wasn’t as it seemed but he answered “very much thanks, hope to see it again sometime” he then went to walk back to his lorry. I closed the door to the car without getting in it and walked after him, he turned and saw me walking behind him but didn’t stop, he got to his cab and climbed in. I arrived at the side of the cab and looking up at him I realised he was older than I’d first thought, maybe about fifty, my age, he put his finger to his lips as though to tell me not to talk then pulled his jeans down around his ankles and started to stroke his cock whilst looking down at me, I think he was quite happy just to carry on but I wasn’t, I climbed up onto the step and grabbed his cock with one hand, steadying myself with my other, he gasped and let me carry on. His cock wasn’t huge, about 7 inches and not too thick either, I even thought that it would be just right if tonight was going to be the night that I pooped my cherry (it wasn’t), I then got into the cab, crawled across him in a not very ladylike way until I was kneeling .on the other seat I bent down and took his now pre-cum filled member into my mouth, it didn’t taste as I thought it would but I didn’t care, it was a bit stale at first but as I licked and sucked that was replaced by the sheer overwhelming desire for him to cum down my throat, it didn’t take long before I got my wish, being a novice I didn’t realise that the ‘twitching’ that was happening was a sign of what was to come, he jerked and arched his back all the while holding the back of my head, he came with such force I thought I was going to choke but I managed to take most of it with some running down my chin and onto my dress.
I could sense that this was time to leave as my ‘conquest’ was now looking rather sheepish and obviously didn’t fancy a post coitus chat. I got down from the cab as ladylike as I had got in being hindered by the erection in my knickers making life hard work, when I got back to the car I leant against the side, got out my cock and after about ten strokes, shot the load of a lifetime all over the door.
Whilst driving home my wife rang me to say that she was having an amazing time and asked if I had enjoyed myself at ten o’clock, I then realised that at that time I probably had another mans cock down my throat so I told her that yes, I’d had a VERY nice time
I have been crossdressing for as long as I can remember, from sneaking a pair of my sisters panties, to even sneaking into the gardens of my parents neighbours and pinching underwear from washing lines. In my late teens when I found girls (and sex) I purged any clothing that I had and managed to put the ’urge’ behind me. I settled down got married etc. etc. Unfortunately for me (or not?) my wife like to wear very sexy underwear, stockings and very revealing outfits which meant there were a lot of these ‘things’ around the house. It started small, again, when on a day off I would be doing some washing and find myself holding the knickers against myself, then wearing them until before long I was back to a full ensemble masturbating furiously.
My wife soon found out what I was doing and, instead of disowning me like I thought she would, she said she understood and would help me out. Before long I had a drawer full of my own clothing and even a couple of pairs of 5 inch stiletto heels, one black pair and a pair of bright red Mary Janes , my favourite. The only stipulation she put on the arrangement was that I only dressed inside the house and if she was with me not in our bedroom, I obviously agreed.
This arrangement went on for quite a few years and to be honest it was all I ever wanted, whilst on a night out she would say to me “when we get home we’ll ‘get comfortable’” she knew this would get me going. I would proceed upstairs and dress in one of my many outfits and we would have the most amazing sex.
I have been a little vague up to now so as not to get the reader to aroused as this isn’t my main story just an insight as to what got me here. My story starts when my wife went away one weekend on a girls hen night, just before she left she whispered in my ear, whilst stroking my cock through my jeans, that if I dressed up tonight at ten o’clock sharp, she would go into the ladies wherever she was and stroke her clit thinking of me doing the same, I nearly came there and then.
Around eight o’clock I started to get ready although as I had been quite excited and had got everything laid out on the bed ready, I was showered and busting to get on with it. I was ready for about eight thirty, walking around the house, I kept walking up to the tall mirror in the bedroom looking at myself, I was quite happy with what I saw. I was wearing a red skater dress which just covered my thighs, I had on a very silky pair of red knickers, my stockings were natural, glossy hold ups with a very deep lace top and the heels had to be of course my five inch bright red Mary Janes, I put on my blonde shoulder length wig and did my make-up as best I could, this was one of the things my wife always did but I was getting better at it.
While I waited I got a little impatient and decided to do something that I had always wanted to, as it was dark outside I thought how naughty it would be to go for a quick drive, I had seen some youtube videos of Gurls walking in front of their cars down quiet lanes etc. I drove to a local industrial estate that as it was weekend would be deserted, I drove around for a short while before parking up at the end of a quiet street where they park the lorry trailers when not in use, what I didn’t know was not all of them were ‘not in use’ I set my camera rolling and started walking up and down in front of my car, stopping every now and then to adjust my stockings and pout at the camera when, to my sheer horror I saw a man standing, looking straight at me. I hadn’t seen him due to the glare of the headlights, schoolgirl error. I went to get into my car, shaking like a leaf, I opened the door and looked up one last time to see that he was near my car and smiling, I don’t know why I did it but I asked him if he’d ‘enjoyed the show’, I think it was now that he realised all wasn’t as it seemed but he answered “very much thanks, hope to see it again sometime” he then went to walk back to his lorry. I closed the door to the car without getting in it and walked after him, he turned and saw me walking behind him but didn’t stop, he got to his cab and climbed in. I arrived at the side of the cab and looking up at him I realised he was older than I’d first thought, maybe about fifty, my age, he put his finger to his lips as though to tell me not to talk then pulled his jeans down around his ankles and started to stroke his cock whilst looking down at me, I think he was quite happy just to carry on but I wasn’t, I climbed up onto the step and grabbed his cock with one hand, steadying myself with my other, he gasped and let me carry on. His cock wasn’t huge, about 7 inches and not too thick either, I even thought that it would be just right if tonight was going to be the night that I pooped my cherry (it wasn’t), I then got into the cab, crawled across him in a not very ladylike way until I was kneeling .on the other seat I bent down and took his now pre-cum filled member into my mouth, it didn’t taste as I thought it would but I didn’t care, it was a bit stale at first but as I licked and sucked that was replaced by the sheer overwhelming desire for him to cum down my throat, it didn’t take long before I got my wish, being a novice I didn’t realise that the ‘twitching’ that was happening was a sign of what was to come, he jerked and arched his back all the while holding the back of my head, he came with such force I thought I was going to choke but I managed to take most of it with some running down my chin and onto my dress.
I could sense that this was time to leave as my ‘conquest’ was now looking rather sheepish and obviously didn’t fancy a post coitus chat. I got down from the cab as ladylike as I had got in being hindered by the erection in my knickers making life hard work, when I got back to the car I leant against the side, got out my cock and after about ten strokes, shot the load of a lifetime all over the door.
Whilst driving home my wife rang me to say that she was having an amazing time and asked if I had enjoyed myself at ten o’clock, I then realised that at that time I probably had another mans cock down my throat so I told her that yes, I’d had a VERY nice time
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