My Qualifications to Write About Crossdressing
- 2 years ago
- 30
- 0
Caught Crossdressing...... free porn video
The below is a true story so naturally names and places changed but the rest of it remains to be one of my memorable moments!!
What seems like many years ago now when I finished university my then girlfriend Lexy and I went down to Cornwall to stay in her parents holiday home for the summer while we worked out what to do. To be honest at this point we both know that we aren’t “the one” for each other but I think we both had the same thought, see what happens over the summer and then make decisions from there. A free house for the summer in the coast, who would say no? The only thing was that her parent would come down occasionally to stay but there was plenty of room so it didn’t really matter. They were quite chilled out and easy going so it was set to be a good summer.
it was getting towards the middle of the summer and Lexy had a week away booked in Ibiza with the girls from Uni so to be honest it was nice to have the place to myself and really chill out for a week. After dropping Lexy off at the train station I grabbed a few beers and supplies from the shop and headed home for an easy day on the beach. With it being quite an over cast day I went back to the house, cooked some food and chilled for a bit and then had a shower and then this is where it all started to go off plan!
When I stepped out of the shower I couldn’t help notice a pair of Lexy’s knickers and I don’t know why it caught my attention as they were always lying around but this time they really stood out. Now I’m not squeaky clean I admit yes I tried on knickers before always loved lady’s in lingerie but it wasn’t something I would say I have done. Also I’m sure a lot of you will appreciate when you have some free time the first night you have free you really feel like it’s time to make the most of things!!! So next thing I know I’m stood in the bed room looking at myself in the mirror wearing the knickers and first impressions are that I’m feeling pretty good, naughty but good. At this time in my life I was quite fit and had a nicely toned upper body only slightly though and quite slender legs and as I’m told a good bum. I quite convinced myself looking in the mirror that my bum and legs could probably pass for quite convincing girl. By now was feeling excited, nervous and in a way a bit guilty for some reason! However I had also convinced myself that I would probably look better in stockings so after quickly finding some I sat on the bed and started to put them on. This was 100% new to me but also there is no one else here and sod it really but the feeling of the nylon stockings going up my legs was a whole new sensation for me and one I will never forget. Something about it felt quite feminine and sexy , I have also loved women wearing them ever since I can remember so it’s only fair I try them as well.
After checking myself out in the mirror quite a few times I put on a dressing gown and went to chill out on the sofa watching a film but I have to be honest by now it’s pretty hard not to notice that this is making me really quite horny and my cock was loving the feeling of the tight silky knickers. The next few minutes were quite possibly the only time in my life I wanted the ground to open up and swallow me!!! I heard a key in the door and voices.........panic like I never have felt before set in and at the time I should of been whipping off the stockings, hiding them and acting normal just chilling out in a robe I found myself running back and forth in the living room repeating shit, oh shit, oh if shit!!!!
As the door opened I just froze and kind of yelled out hi Henry and Jane how are you I don’t realise you were coming!!! My best bet at this point was just to act as normal as possible and pray the my don’t look down at my feet and realise I’m wearing a pair of stockings!!! It was clear they had a few G&Ts on the train so I’m starting to think I have nailed this and then it happens Jane looks down at the floor as she puts her bag down and I see her pause. Oh no I’m thinking trying to move around the sofa but I think it’s too late, had she seen or not?? As she stood back up she looked at me and just said we’ve had such a long journey we will be off to bed, sorry for disturbing you but let’s talk in the morning.
As they go off to their bedroom my world is ending around me pretty rapidly and in my head I’m making my exit plan and if I hadn’t if had a few beers before I would of just grabbed all my stuff hoped in the car and fled into the night. Needless to say I didn’t sleep much that night at all and thought it best to leave the house early and stay out as long as I could and delay my next embarrassment. It got to lunch time and in my hurry I had left my wallet and decided to head home and face the music as it would have to happen sometime. When I got back I saw that Jane was out sunbathing on the deck and although the panic hit me again I couldn’t help but notice that Jane had an incredible body in her bikini. Jane was mid 50’s tanned and blonde and I have to admit she was a very good looking lady with gorgeous curves and boobs and I would be lying if I said I hadn’t thought about her once or twice before. All this went out the window though as it was now or never that she would say something or should I but as I approached her she said hey you why don’t you grab a Pimms and come and join me. I thought if all the excuses I could say but it was an impossible offer to turn down so I sat down and with each minute passing without it getting mentioned I was panicking less and relaxing. Turns out Henry was playing golf and then going out for drinks so we had plenty of time to catch up. Jane then started adding gin into the Pimms and we were both getting a little tipsy and not relaxed and the next bit threw me as Jane said why don’t you go and make me one of those funny cigarettes I know you have sometimes. She then explained it had been years since she had had a “smoke” and she would love it. I was quite young still and always kept a little bit for a party so I happily obliged and we enjoyed a bonding moment shall we say.
We chat until the late afternoon and then Jane just lowers her sunglasses, looks right at me and says do you always wear tights or stockings when you’re in your own?!? There it is the question I had been dreading and I imagine her anxious to ask. What do I say to her that she will believe as this is genuine first time really and if I say that I’m sure she won’t believe me. I kind of put together a stumbled answer of no it’s my first time errrr kind of thing. I literally said to her please can you not tell anyone as this is rather embarrassing for me. She sat back on her lounger and said quite casually it’s none of my business but I would imagine you look very nice in whatever you were wearing and I was professional make up artist for a while and she said I had good features!!! What the hell is going on I ask myself but at the same time I noticed that her tone had changed and something about it was quite enticing!! After a bit of my drink she then went in to say it can be our secret but she would love to get her kit out and turn me into a girl for a giggle, as I mentioned I’m quite tipsy by now and I’m half saying no but half saying yes just for the laugh. Maybe a little horny too..
After a bit of joking she sends me to the living room while she gets her kit that she kept here and I have to say at this point im just going with the flow and having a laugh. Jane brings out this case which is huge with all her make up and wigs too. It took her a while but she did it she worked her old magic and made me look pretty feminine with a brunette long wig. We joked around a bit more all harmless and and I said right Henry will be back at some point let’s take it off. Jane’s tine changed again to a bit more assertive and said not a chance we said it will be our secret and I can turn you into a girl and your not dressed yet. She then produces a pair of her stockings, very sexy knickers and a sexy black basque!! I’m starting to think this is a little too far but what the hell! Jane then handed me a dress and a pair of heels. Never in my life would I think I would be doing this but it also felt pretty good. Somehow I managed to squeeze my feet into the heels and the dress only just fit and to my surprise I looked really quite feminine and also a little slutty.
I won’t lie I’m feeling really naughty and horny by now and Jane suggests that we should try and fill Henry for a bit as he would of had a few drinks and wouldn’t notice. Just 10 mins she said then I could leave and creep in the back while she distracted him. I also mentioned I was feeling naughty and by this I mean Jane is really in my thoughts now as she is still in her bikini and a sarong and I can’t take my eyes off her gorgeous full mature boobs. Somehow she convinces me and I think the gin helped but Henry comes home and Jane introduces me as Sophia and Henry goes on to bore us with his golf story and Jane was right he had a few and I was starting to think he wouldn’t notice. Watching the clock 8 mins have passed and I’m out of here in two then Jane announces she is off to get dressed and will be right back. Don’t go until I’m back Sophia she says!! Oh great how am I going to convince Henry and as he speaks to me I put on my best girly voice and reply short answers. It seems to take Jane forever to get dressed and when she came out I honestly didn’t know what to think, she comes out in six inch shiny black heels, anklet, stockings and a very shirt and tight latex skirt and white blouse. I can see underneath her gorgeous breasts at a guess they must of been EE or FF they were simply stunning. Although I was excited by what I saw also feeling that this is an odd situation.
As this all happens Henry obviously feeling like his luck is in in said Sophia I hope you don’t mind me saying but Jane you look incredibly sexy but we do have a guest. Jane laughs it off saying all her other clothes are in the wash!!! Haha anyway Jane wants cocktails so we head to the kitchen and Henry starts doing his best Tom Cruise making the cocktails. Jane and I are stood the other side of the kitchen island and I can feel her hand grabbing my bum and as Henry isn’t paying attention whispers in my ear you look hot Sophia!!! Mind boggling moments for me and without a care in the world I whispered back to her that i felt so horny and girly!! We’ve all had a few drinks and I have almost forgotten that I’m not Sophia and I’m face these are my girlfriends parents but I’m feeling something I’ve never felt before and I’m loving it. Henry decided to go outside for a smoke and for me and Jane to join him if we want. Ad he leaves the room Jane turns round to me pulls me in and kissed me so softly and licking my lips and just lips right at me and says tonight you’re going to be my Sophia.......
What seems like many years ago now when I finished university my then girlfriend Lexy and I went down to Cornwall to stay in her parents holiday home for the summer while we worked out what to do. To be honest at this point we both know that we aren’t “the one” for each other but I think we both had the same thought, see what happens over the summer and then make decisions from there. A free house for the summer in the coast, who would say no? The only thing was that her parent would come down occasionally to stay but there was plenty of room so it didn’t really matter. They were quite chilled out and easy going so it was set to be a good summer.
it was getting towards the middle of the summer and Lexy had a week away booked in Ibiza with the girls from Uni so to be honest it was nice to have the place to myself and really chill out for a week. After dropping Lexy off at the train station I grabbed a few beers and supplies from the shop and headed home for an easy day on the beach. With it being quite an over cast day I went back to the house, cooked some food and chilled for a bit and then had a shower and then this is where it all started to go off plan!
When I stepped out of the shower I couldn’t help notice a pair of Lexy’s knickers and I don’t know why it caught my attention as they were always lying around but this time they really stood out. Now I’m not squeaky clean I admit yes I tried on knickers before always loved lady’s in lingerie but it wasn’t something I would say I have done. Also I’m sure a lot of you will appreciate when you have some free time the first night you have free you really feel like it’s time to make the most of things!!! So next thing I know I’m stood in the bed room looking at myself in the mirror wearing the knickers and first impressions are that I’m feeling pretty good, naughty but good. At this time in my life I was quite fit and had a nicely toned upper body only slightly though and quite slender legs and as I’m told a good bum. I quite convinced myself looking in the mirror that my bum and legs could probably pass for quite convincing girl. By now was feeling excited, nervous and in a way a bit guilty for some reason! However I had also convinced myself that I would probably look better in stockings so after quickly finding some I sat on the bed and started to put them on. This was 100% new to me but also there is no one else here and sod it really but the feeling of the nylon stockings going up my legs was a whole new sensation for me and one I will never forget. Something about it felt quite feminine and sexy , I have also loved women wearing them ever since I can remember so it’s only fair I try them as well.
After checking myself out in the mirror quite a few times I put on a dressing gown and went to chill out on the sofa watching a film but I have to be honest by now it’s pretty hard not to notice that this is making me really quite horny and my cock was loving the feeling of the tight silky knickers. The next few minutes were quite possibly the only time in my life I wanted the ground to open up and swallow me!!! I heard a key in the door and voices.........panic like I never have felt before set in and at the time I should of been whipping off the stockings, hiding them and acting normal just chilling out in a robe I found myself running back and forth in the living room repeating shit, oh shit, oh if shit!!!!
As the door opened I just froze and kind of yelled out hi Henry and Jane how are you I don’t realise you were coming!!! My best bet at this point was just to act as normal as possible and pray the my don’t look down at my feet and realise I’m wearing a pair of stockings!!! It was clear they had a few G&Ts on the train so I’m starting to think I have nailed this and then it happens Jane looks down at the floor as she puts her bag down and I see her pause. Oh no I’m thinking trying to move around the sofa but I think it’s too late, had she seen or not?? As she stood back up she looked at me and just said we’ve had such a long journey we will be off to bed, sorry for disturbing you but let’s talk in the morning.
As they go off to their bedroom my world is ending around me pretty rapidly and in my head I’m making my exit plan and if I hadn’t if had a few beers before I would of just grabbed all my stuff hoped in the car and fled into the night. Needless to say I didn’t sleep much that night at all and thought it best to leave the house early and stay out as long as I could and delay my next embarrassment. It got to lunch time and in my hurry I had left my wallet and decided to head home and face the music as it would have to happen sometime. When I got back I saw that Jane was out sunbathing on the deck and although the panic hit me again I couldn’t help but notice that Jane had an incredible body in her bikini. Jane was mid 50’s tanned and blonde and I have to admit she was a very good looking lady with gorgeous curves and boobs and I would be lying if I said I hadn’t thought about her once or twice before. All this went out the window though as it was now or never that she would say something or should I but as I approached her she said hey you why don’t you grab a Pimms and come and join me. I thought if all the excuses I could say but it was an impossible offer to turn down so I sat down and with each minute passing without it getting mentioned I was panicking less and relaxing. Turns out Henry was playing golf and then going out for drinks so we had plenty of time to catch up. Jane then started adding gin into the Pimms and we were both getting a little tipsy and not relaxed and the next bit threw me as Jane said why don’t you go and make me one of those funny cigarettes I know you have sometimes. She then explained it had been years since she had had a “smoke” and she would love it. I was quite young still and always kept a little bit for a party so I happily obliged and we enjoyed a bonding moment shall we say.
We chat until the late afternoon and then Jane just lowers her sunglasses, looks right at me and says do you always wear tights or stockings when you’re in your own?!? There it is the question I had been dreading and I imagine her anxious to ask. What do I say to her that she will believe as this is genuine first time really and if I say that I’m sure she won’t believe me. I kind of put together a stumbled answer of no it’s my first time errrr kind of thing. I literally said to her please can you not tell anyone as this is rather embarrassing for me. She sat back on her lounger and said quite casually it’s none of my business but I would imagine you look very nice in whatever you were wearing and I was professional make up artist for a while and she said I had good features!!! What the hell is going on I ask myself but at the same time I noticed that her tone had changed and something about it was quite enticing!! After a bit of my drink she then went in to say it can be our secret but she would love to get her kit out and turn me into a girl for a giggle, as I mentioned I’m quite tipsy by now and I’m half saying no but half saying yes just for the laugh. Maybe a little horny too..
After a bit of joking she sends me to the living room while she gets her kit that she kept here and I have to say at this point im just going with the flow and having a laugh. Jane brings out this case which is huge with all her make up and wigs too. It took her a while but she did it she worked her old magic and made me look pretty feminine with a brunette long wig. We joked around a bit more all harmless and and I said right Henry will be back at some point let’s take it off. Jane’s tine changed again to a bit more assertive and said not a chance we said it will be our secret and I can turn you into a girl and your not dressed yet. She then produces a pair of her stockings, very sexy knickers and a sexy black basque!! I’m starting to think this is a little too far but what the hell! Jane then handed me a dress and a pair of heels. Never in my life would I think I would be doing this but it also felt pretty good. Somehow I managed to squeeze my feet into the heels and the dress only just fit and to my surprise I looked really quite feminine and also a little slutty.
I won’t lie I’m feeling really naughty and horny by now and Jane suggests that we should try and fill Henry for a bit as he would of had a few drinks and wouldn’t notice. Just 10 mins she said then I could leave and creep in the back while she distracted him. I also mentioned I was feeling naughty and by this I mean Jane is really in my thoughts now as she is still in her bikini and a sarong and I can’t take my eyes off her gorgeous full mature boobs. Somehow she convinces me and I think the gin helped but Henry comes home and Jane introduces me as Sophia and Henry goes on to bore us with his golf story and Jane was right he had a few and I was starting to think he wouldn’t notice. Watching the clock 8 mins have passed and I’m out of here in two then Jane announces she is off to get dressed and will be right back. Don’t go until I’m back Sophia she says!! Oh great how am I going to convince Henry and as he speaks to me I put on my best girly voice and reply short answers. It seems to take Jane forever to get dressed and when she came out I honestly didn’t know what to think, she comes out in six inch shiny black heels, anklet, stockings and a very shirt and tight latex skirt and white blouse. I can see underneath her gorgeous breasts at a guess they must of been EE or FF they were simply stunning. Although I was excited by what I saw also feeling that this is an odd situation.
As this all happens Henry obviously feeling like his luck is in in said Sophia I hope you don’t mind me saying but Jane you look incredibly sexy but we do have a guest. Jane laughs it off saying all her other clothes are in the wash!!! Haha anyway Jane wants cocktails so we head to the kitchen and Henry starts doing his best Tom Cruise making the cocktails. Jane and I are stood the other side of the kitchen island and I can feel her hand grabbing my bum and as Henry isn’t paying attention whispers in my ear you look hot Sophia!!! Mind boggling moments for me and without a care in the world I whispered back to her that i felt so horny and girly!! We’ve all had a few drinks and I have almost forgotten that I’m not Sophia and I’m face these are my girlfriends parents but I’m feeling something I’ve never felt before and I’m loving it. Henry decided to go outside for a smoke and for me and Jane to join him if we want. Ad he leaves the room Jane turns round to me pulls me in and kissed me so softly and licking my lips and just lips right at me and says tonight you’re going to be my Sophia.......
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