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Caught Crossdressing by Friend

Caught crossdressing by friend

My name is Geraldine and here is a story of how a friend discovered that I was a secret cross dresser. The experience I am about to tell you about happened when I was about 23. I had been dressing for years and loved how amazing wearing female clothing made me feel. I about 5ft 7 and have a very slim and toned body which I keep in shape by going to the gym and running. I was firmly in the closet at this time although I had often toyed with the idea of going to a crossdressing club dressed as a girl and my ultimate fantasy has always been to go on a date with a guy.

On the morning in question I woke and checked the time which was 8:48. I had arranged to meet a friend at the gym later that morning but had over an hour to kill. I had recently purchased a bikini online and had been dying for a chance to put it on. I got out of bed and removed the bikini which was black from its packaging and proceeded to put the top on.

The top was a little tight but I managed to put it on and then proceeded to slide the bottoms which were super cute up my legs. I put on my brunette shoulder length wig and posed in front of my full length mirror and was pleased with how sexy the bikini made my body look. I also started to feel jealous of genetic girls who have the opportunity to wear clothes like this out in public.

After a while I decided that I needed to get ready to meet my friend so I took off the bikini and put on my normal boring male clothes for the gym which consisted of a loose fitting t-shirt, knee length shorts and a pair of trainers. I had a good session in the gym concentrating on the cross trainer and squats to help reduce my waist even more and instantiate my arse in an attempt to give myself more of a more hour glass figure.

After the gym, me and my friend Greg decided to go for a coffee. We were talking when Greg suddenly asked me how long had I been wearing women’s clothes. I stuttered and asked what do you mean.

Gregg said that he noticed when we were getting changed that there were strap marks on my shoulders and back and that it looked like I had been wearing a bra. I went bright I hadn’t even crossed my mind that my dressing session earlier that morning would have left any telltale marks. I confessed that I enjoyed wearing women’s clothes and that he was right and that I had been wearing a bikini top that morning.

Gregg smiled and said that he was fine with it and that he would love to see me fully dressed some time. I laughed and said that I only did it in private. However, the thought of somebody else seeing me fully dressed was secretly starting to turn me on.

Several weeks passed and me and Gregg hung out quite a bit and went to the gym a few more times without anymore being said. However, one evening when Gregg was over at my apartment my curiosity got the better of me.

We were playing a racing game which required us both to put in a user name. I decided to be a little naughty and instead of putting in my real name I entered my female name Geraldine. Gregg asked me if that was my female name and I smiled and said yes.

I also went a little bit further and asked him if he was still interested in seeing me fully dressed. Gregg said yes so I told him that I would need to go to my room to get ready and left him playing computer games.

I felt very excited. Once in my bedroom I stripped completely nake-d and looked at myself in the mirror. I had kinda already thought that things might happen and had spent time earlier that day removing all of my body hair. I opened my underwear draw and took out a red satin bra and pantie set with black lace edging which I put on.

I then put a pair of nude seamed stockings up my legs. I checked myself in the mirror to make sure the seams were straight. I was happy with how lovely it made my legs appear so smooth and se-xy.

I then went to my wardrobe and started to look at my collection of female clothes and tried to decide what i was going to wear next. I took out a couple of outfits but decided that a silky yellow skater dress that came to just above my knees was just right for the occasion.

I put the dress on and started to apply my make up. I applied foundation and then mascara to my eye lashes and then proceeded with eye liner. I then added some blush and started to contour my face paying attention to my cheek bones and then finished my make up with some bright red lipstick.

I completed the look with my brunette shoulder length wig and started to pose in front of the mirror pleased with the look of the pretty albeit a little bit slutty girl staring back at me. I slipped on a pair of black heels which seemed to make my legs and arse look even more shapely.

I couldn’t believe that somebody was about to see me fully dressed for the first time and I could feel butterflies in my stomach as I walked back into the living room to show Gregg.

Gregg just said wow which made me blush and I gave him a bit of a twirl and felt the skater skirt rise as I did so exposing my stocking tops. I have to admit I was starting to feel extremely arous-ed. Gregg said that I looked amazing and that he would just like to see me in my under-wear.

I was nervous at first but I was feeling so arou-sed I decided to unzip the dress and let it drop to the floor and just stood there in front of him in just by bra, panties and suspenders. Gregg started to cross his legs and I could see that he was starting to find this whole encounter as se-xy as I was.

I asked Gregg if I was starting to turn him on to which he replied yes. I grinned a mischievous grin and started to crawl on all fours towards him and felt the suspender straps digging into my arse.

I felt so se-xy as I knelt in front of him and brushed my hand against his bulge which I could visibly see starting to get hard through his trousers. Gregg didn’t resist so I proceeded to unzip his flies and release his co-ck and slowly started to rub the shaft up and down.

Gregg wasn’t fully hard yet so I leaned over and took the tip in my mouth and felt a great sense of excited go through my whole body as I felt him become fully erec-t in my mouth.

There I was on all fours wearing possible the se-xiest lingerie set I had ever owned giving my first ever blow-job. I was in heaven and had never felt more womanly in my life.

I started to bob my head up and down stopping occasionally to concentrate on the head. I started to tease his fore-skin with my tongue and then proceeded to slip my tongue under his fore-skin which made him become even harder.

I continued to alternate from bobbing my head up and down to just concentrating on the head and could tell from the sounds that Gregg was making that he was enjoying himself. Gregg said that he wasn’t going to last much longer which just encouraged me to suc-k even harder.

‘Oh you se-xy girl’ I heard Gregg whimper as I started to feel his co-ck start to throb in my mouth and was soon rewarded as I felt stream after stream on sem-en erupt from his co-ck and hit the back of my mouth.

This was the first time I had ever tasted sem-en and as I had gone this far I decided that I was going to go the whole way and swallow. I swallowed it all down and started to lick his co-ck making sure it was fully clean and then winked and thanked him.

I felt so empowered being able to make a man cu-m only using my mouth and Gregg said that it was the best blowjob he had ever had.

I thanked him for the compliment and put the dress back on and poured us both a drink.

Gregg left soon after and as he left I still couldn’t believe what I had done but that but it was not the last time that he got to meet Geraldine.

The End

Story written by Geraldine01

Facebook Comments


  1. Mmmm… lovely story Geraldine!! I felt really identified with you, and it was so exciting to read how you describe your love encounter with your friend… To experience that would be a dream come true for me… Thanks for sharing, and for write so well!

  2. I dress every day I enjoy it. This is what I do to make time go faster. I like the feel of the clothes and I like warring skirts I feel it is easier to go the bathroom in a skirt then with pants. Men sometimes fight to get the zipper down but with a skirt just lift it up and go.

  3. Oh how wonderful for you so very exciting to think about thanks so much for sharing, hugs,patty

  4. What a lovely story, it made me so hard and jealous. Just the thought of being dressed in female clothes and being with a man is such a turn on.

  5. Me encantó tu historia y tu relato me sentí muy identificada me pasó algo muy parecido a los 26 y desde allí no pude parar mas, trato de superarme como mujer día a día hoy tengo 50 años y trato de vivir como Martina lo máximo posible en el día y saliendo de noche también desde hace unos años. Soy de Buenos Aires. Argentina.
    Beso grande.

    1. Martina me gusto tu mensaje y me gustaria ver algunas fotos tuyas 😘😘😘

  6. Merci pour ce récit Géraldine. Je me suis mise à ta place un instant c’était un moment délicieux.

  7. First co-ck. Even if just in the mouth, you’ll never be the same.

  8. Omg that was very sexy. The part about anticipating that something might happen was my favorite. What a beautiful story!

  9. I’m glad to hear Geraldine swallowed, I always swallow because it’s the least messy option & men expect you to do so, but above all I just love the taste & as a woman I’m showing my appreciation to the man who has usually he’s just given me a good seeing to.

  10. wish i had a friend catch me when i was young

  11. Lucious story and encounter!

  12. Awesome story. I have a couple friends I would love to do the same.

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