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OMG Last Night

"last night a first for me"

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Famous Story

I suppose I'd better start at the beginning. Well, my femme name is Carly Hughes.I'm a 47-year-old male who has probably been cross-dressing since he was seven. I started dressing in my mum's and sister's clothes. I've built up stashes of clothes many times and binned them through guilt. I've probably wasted so much cash it's unbelievable.

Anyway, I've done all the manly things in my life like football, being a jack the lad, getting married, becoming a dad, etc. Through all the years my cross-dressing was suppressed, but three months ago I split up with my wife not because of the cross-dressing but due to other reasons. I think I hid the cross-dressing well and she never realized I had a secret stash of clothes in the attic.

Now I am living in a rented room in a very nice lady's house. My cross-dressing urges have come back with a vengeance, from maybe dressing three to four times a year I'm now dressing every Friday and Saturday night as my landlady goes to her boyfriend's on the weekends.

My make up skills have vastly improved going from looking a little feminine, to with the help of eBay and YouTube videos to looking very very feminine. Contouring videos on YouTube are a must for anyone who does not want to look like a clown. In addition to that, I'm about 74 kgs (just under 12 stone), 5ft 8, and I've managed to slim down to a 32-inch waist so I can fit into UK size 12 women's clothes.

Anyway last night, I had grown bored of standing in front of my mirror changing outfits every five minutes, I'd been venturing outside at night, at first just driving around and finding somewhere extremely quiet and going for a quick, exciting walk, till the events of last night which were a first for me.

So last night I used medical adhesive and glued on my breast forms. They were only cheap ones but using a little silicone putty around the top and sides I blended them into my skin and then used a little foundation and powder to blend them in so you couldn't see where they joined my body. I'd also glued on my bum and hip silicone pads. I did not bother blending them in though. I'd tucked and used a little tape to hold myself in place downstairs. Because I couldn't shave my legs as I'm going away soon, I put on a pair of tights then my tiny thong panties and then another pair of tights just so you could not see any leg hairs,

My clothes for the evening were. A black Lycra skirt that's let's just say figure hugging around my bum and just over knee height, I teamed that up with a black vest top that clung to my now ample breasts, I was going braless as I'd glued my puppies on.

I had applied my make up perfectly well in my mind anyway. I put on my blonde Jennifer Anniston style wig, brushed it out and styled it to suit then slipped on my black ballet pumps, next was my brown short leather jacket, it's sort of biker style with lots of zips on it. I grabbed my handbag and headed out.

I had decided tonight's plan was to walk to the cash point about ten minutes away, get some cash then come home, by now it was around 10 pm, so it was dark, my favorite time as it's much much easier to pass in the dark.

I had been to the cashpoint and was on my way home when I saw a transit tipper van coming down the road heading towards me. It went past me. I thought 'phew,' but as I went around a corner, I heard the same van reversing quickly and racing back in my direction. I didn't know the reason why but I just knew he was coming back for me,

I panicked and started walking much quicker as I did not know if he realized I was a guy and coming to take the piss or to give me aggro or whether he liked what he saw and was coming to try his luck with me. The van raced down the road and slowed down as it drew alongside me, it revved its engine, and I heard the electric passenger window come down. To be honest, I was absolutely shitting myself as I was just thinking this is only going end badly.

The guy shouted to me through the window, "Hey beautiful what's a good looking woman like you doing walking home by herself this time of day."

 I froze and stopped walking an looked at him, he then shouted, "If you were mine I'd never let you outta the bedroom." He then asked if I wanted some fun.

I put my right hand on my hip an waved my left hand at him an said in the most feminine voice I could muster, "Sorry honey I'm married an just off home to my lucky husband."

 He said my husband was a lucky guy and raced off.

I had never been so glad that when I split with my wife that she gave me back her wedding and engagement rings an with a little effort, I could get them on.

Quickly I made it home.  As I got into the house, I was so nervous as that was my very first interaction with anybody dressed as Carly, it was amazing, exhilarating but also very very scary.

I relaxed in the front room with a Baileys or two or three and thought about how the events could have turned out much worst. I decided I was a lucky girl and had got away with it.

About 2 hrs later around 12.30, I decided that if I had passed with the van driver that I'd go out again for a walk, this time I felt a lot braver as I had more than a few Baileys, and because of my interaction with the van driver.

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I had been walking for around 15 minutes when I was just about to go around a corner, I could hear two guys chatting as they headed my way.

To be honest, my bravery went out of the window, and I chickened out, I turned around and started heading back the way I'd just come, as I did I heard the two guys voices get a lot louder, I thought to my self that I was lucky that I had turned around when I did.

But then I realised their voices were much much louder, then they came around the corner an I realized that they were on bikes, I heard one say, "Fucking hell, Gary, look at that, I smash that in a heartbeat."

I chuckled to myself, then the fear of god went through me as I realised that he was on about me, just then I had two routes I could go, to the left was a dark alley, to the right was a well-lit road.

I decided to go to the right the well-lit option, as the guy who had said about doing me went to the left, up the darker alleyway and Gary went to the right, Gary shouted to the other man, "Night mate I'm off, and rode off into the night,"

I relaxed as I thought they had both gone, just then the guy who had gone along the dark ally came out of an alleyway on his bike.

He rode up next to me jumped off his bike and walked next to me while pushing his bike. He grabbed my hand an spun me around before I realized it he had his hands around my waist an was kissing me. I do not know if it was the drink, but I responded I parted my lips slightly, his tongue invaded my mouth.

As he kissed me he pulled me in close to him, he must have been at least 6ft or maybe taller because as he pulled me in close to him, I could feel his cock pushed into my stomach. I sort of liked the feeling that this guy was hard for me, yes me, if only he knew I had the same equipment tucked away in my panties.

I felt him touch one of my breasts, I moaned with pleasure as he touched me, just to keep up the effect as if they were real, as I didn't want him finding out I was the same sex as him. He rubbed my nipples, I moaned a little more, he then grabbed my hand an placed it on his dick, my god he was huge.

To be honest, I do not really know what huge is in dick sizes, but I just knew he was much larger than me, and I am not tiny.

I do not know why but I unzipped his jeans an pulled out his cock. I could now confirm that he was huge. I started to wank him as his hand slid down my body, I knew it was heading south, he stroked my bum before his hand drifted around to my stomach, I felt his fingers start to pull at the waistband of my skirt.

 I thought quickly and told him "I was on my period," but I could satisfy him if he wanted me to. He said "Yes please, babe," and without realizing it I dropped to my knees an took him in my mouth. I started to give him the best blow job I could, trying to remember what I liked my wife doing to me,

I decided to try and take as much of him in my mouth as I could. There was no way I could deep throat him like the wife used to do to me,  but I did gently let my teeth run against his shaft as I moved up an down his hard dick. It did not take long until I felt his cock harden, then twitch a little bit more, till he filled my mouth with his hot salty cum.

I swallowed as much as I could, I think there was just a bit on my face that I wiped off with my finger, I licked him clean.  He put himself away and said, "That was awesome," to say I was pleased that I had gotten away with passing as a woman and satisfying a man with just my mouth was an understatement, it's amazing how much power a woman has over a man, when his cock is in her mouth.

He jumped on his bike an said "that was much better than my girlfriend does" and e asked if could he have my phone number, I said to him "I'm married," and flashed my wedding ring at him, and that it was a one of. He looked at me with a look of anger on his face and rode off on his bike.

I stood there alone for a few minutes had a cigarette, and thought how lucky I had been as if he had found out or realized I was a guy he could have beaten me to a pulp. I thought taking control was my best option, I know I sucked his cock, but it could have been worse, and he may have tried to rape me as he did not know I was a guy.

I have now decided that when I go for a walk at night not to put my self in dangerous places and to stick to well-lit areas, just like a real woman would and not draw attention to myself.

Anyway, at least the guy on the bike has a story to tell his mates, that he got a blow job on the way home, from a good-looking woman, although they probably won't believe him lol.

It was a night of firsts for me, before last night I'd never spoken to anyone as Carly, and I had always hidden away or turned around if someone was walking my way through fear of being read. It was not the night I had planned to have. But at least I now know I can pass as a woman even with my voice in a scary situation.

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Written by carlyhughes2018
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