Crossdresser Leaves the Closet

I looked back in the mirror. Again I was met by the reflection of an attractive woman, even if I do say so myself. In her early thirties, well made up, with perfectly shaded eyes, ruby red lips, and long red hair. A red stretchy top was wrapped tight around my very large tits...I mean, two hands full each side! A black tight skirt fell to the mid of my thighs. My legs in fishnet stockings, in knee high tight leather boots, with spike stiletto heels.

I had seen her so many times before, and everytime I had bottled it when wanting to go out like this. Every time I just returned to some chatroom for a horny chat, and maybe jacking myself off on camera, only showing my face to other cross dressers, never to admirers.

"Not today!" I told the woman in the mirror."

"Today you will go out, dressed like this, and you will like it! No, love it!! And if anyone gives you grief, you carry on. And if you someone fancies you, and you fancy them back, go for it!"

I was determined to not waste another day, pondering about what might have been. And not to mention the money spent on clothing, make-up, shoes...the supersized breastforms did not come cheap, that's for sure.

Anyway, I digress. I am Charles in my born male guise. Now 32 years old, and a long practicing cross dresser. In fact, practicing is just about all I've done in fairness. Firmly tucked away in my closet, only venturing out online. Such nice and sexy people I've spoken with. Just everyday stuff, but also really sexy chats, and phone calls. A few of my online contacts really lived within a 15 minute walking radius from where I was.

But, I had managed to dodge every offer to meet up, no matter how tempted I was. My nerves always got the better of me, and I had weaseled or lied my way out of meeting up countless times.

I had recently lost a friend to illness, and my last few talks with him very much centered around opportunities missed or wasted. I decided to take his advice and 'live life like my life depended on it'.

I started following tutorials online about make-up. My smokey eyes were soon very sexy and smokey, with the various colour schemes matching hair colour of my wigs, and clothing I wore. I became a dab hand at applying fake eye lashes and nails. Working alone and from home I learned to type, use my phone and do all sorts of jobs with long nails without chipping them or getting caught in or by things.

When fully dressed Charles became Carey, and Carey was becoming increasingly confident and an increasingly frequent presence over Charles. And now, after around 6 months of perfecting being Carey to just the way I Iiked her, in various looks and styles, she was ready to venture out. I had made some video calls to business contacts as Carey, pretending to be Charles' assistant. None twigged, two even contacted Charles to ask if Carey was single and available. Charles politely brushed them off, knowing at least one of them was married.

It was now Sunday afternoon, and Carey looked stunning. I put a long jacket on, which fell well past my skirt. It would however invite people to try and see what they could get a glimpse of as I walked by. I grabbed a shoulder bag, and checked one last time in the mirror. The long red hair framed my face. If the wind were to catch it, my dangly earrings would show. I have plenty of jewellery on. A long necklace with a large pendant rested on my fake tits, and a few bracelets rattled as I moved my hands.

I opened my front door, carefully looking if anyone was outside. Nobody was there, which was a relief. The door closed behind me, and I was off! I was confident in heels indoors, outdoors there are literally quite a few potential pitfalls. However, soon I was focussing on my stride, shortening my steps to increase the sway of my hips. I slowed myself down, now starting to enjoy the ticking of my heels on the pavement.

I saw several people, and they appeared to not see or notice me. Carey was just blending in so far. Until I saw a female figure I recognised. Rebecca, one of the local cross dressers I had met online, was also out. Rebecca was the one that came closest to luring me out before I was ready. And Rebecca had clocked me, and made a beeline towards me.

Rebecca is about 10 years my senior, however, many women, or men, of the same age, would be envious of how well and attractive Rebecca looked. We are the same height, at 5ft11, in heels we reach well over 6ft. However, with women being taller these days, we didn't stand out as much in heels.

Rebecca is slim, but muscular. The best legs ever, and a sweet soft spoken voice. She carried herself in a manner that was elegant, stylish and dripping with grace. She wore a short red dress, bare legs in sandals with a nice 4 inch heel. Her hair was done up in a loose bun, fanning out. Rebecca's make-up was fantastically well done. Truth be told, she was the one I aspired to match in the quality of applying make-up.

Her honey blond hair moved in the wind as she headed towards me. The loose bun almost fanning out, the strands framing her face looked perfect. Her green eyes were smiling along with the rest of her face. Her red lips and nails were a perfect colour match with her dress. I was largely relieved that the first person Carey came across in the flesh was a friend. Rebecca was well aware I had chickened out of every attempt to meet up, and she had said so much. She also said that she would be happy once I made that first tentative journey out.

"Carey?!" she called out as she approached. The last few metres she ran - quite well in those heels - and grabbed my hands.

"I did it Rebecca! Day one of Carey and her new confidence being let loose on the world," I laughed.

"Sweetheart, I can't tell you how happy I am for you!" she replied.

She actually started to tear up a bit. She hugged me, then kissed my cheeks.

"Were you heading anywhere in particular?" she asked.

I told her I was just wandering around, trying to think of somewhere to go, or something to do. Rebecca was heading to the town centre, do some shopping, and have a coffee.

"Do you care to join me? Or is that still a bit scary?" she asked.

"And you don't have to worry about looking convincing enough, you look gorgeous and beautiful. And I still haven't forgotten our last naughty phone call. At least I know now that we're one step closer to making that come true as well," she said whilst taking my hands.

"I really like you, and I really want you, just so you know," she added.

I could feel something stirring inside me, something that had never seen the temptation in real life. Carey was blossoming inside me, and I felt my new found confidence soar.

"Come on, let's head into town," I said, as I hooked my arm into Rebecca's.

In town we shopped, for make-up and shoes, and I bought a sexy corset, with six garter straps. The girl in the shoe shop took her time to help me in and out of shoes and boots, her hands lingering on my legs for inappropriately, but very lovely, lengths of time. She kept trying to peak under my skirt and under Rebecca's dress.

Rebecca was certain the little slut was touching her own pussy as she was trying to ogle my man pussy, which we were sure she thought she would find there. I walked away with a pair of red sandals with a wrap around Roman strap, and 5 inch heels. Rebecca dared me to wear them on our next time out.

We went for lunch, with me paying from my new woman's purse. A small but significant victory. We talked about all sorts, and I felt more Carey and less Charles by the minute. I also realised how I had nearly ended up wishing my life away.

"Would this new Carey have said yes if the little shoe slut had been more brazen, and asked you out, or made a pass at you?" Rebecca asked.

"Well, I could be tempted. But there's people that I certainly could not resist," I replied.

"Might I be one of those people?" Rebecca asked, with a glint in her eyes.

"Sweetheart, you only have to ask once, and I would not even want to try and resist you," I said, feeling very assertive all of the sudden.

Rebecca sat there for a minute, quietly enjoying her green tea. She was clearly thinking of something, and after a few minutes of silence she looked me in the eye.

"Come with me, as in come home with me. You have no more excuses, we both look hot as hell, and I want you. I need you in my arms, in my mouth, in my tranny cunt. We are going to have long horny sex, and I am not taking no for an answer!" she said.

"Well, you're not wasting any time, are you?" I laughed.

"Are you horny now Rebecca? Do you want to suck my cock, and finger me from behind? Do you want Carey as your lover?" I whispered, staring her deep in her eyes.

"Yes...I do," she whispered back.

We finished our drinks, and got up. Our large tits pressed against each other. We both noticed two women licking their lips watching us. We smiled sweetly, then kissed each other, openly, hungrily, tenderly. One of the women, a beautiful black woman, ran her hands over her tits, down to between her legs. Her full pink lips were moist as she ran her tongue over them.

As we walked past her table she handed Rebecca a note, with her name and phone number on it. She looked at us, and said: "anytime, one of you or both of you."

Her name, according to the card, was Ruby, and we quickly introduced ourselves too.

"Now go, she wants you. Fuck her good and hard," Ruby told me with a knowing smile.

Rebecca almost dragged me with her. I was about to be used and abused, and I was looking forward to that a lot.

We walked home together, and my female stride had become more and more assured. We hooked arms, laughed, talked. Every so often we stopped, for a very public display of affection. We kissed, our tongues becoming acquainted.

When we got to Rebecca's house, she stopped in front of her door. She wanted to triple check I wanted to go through with this, and she made me promise before unlocking her front door.

"Come in, and make yourself at home. Let's get to know each other better...much better," she said as she gestured me through to her living room.

As I would expect, her sense of style was impeccable. Elegant, tasteful, and extremely feminine. Erotic artwork adorned the walls, and I recognised Rebecca in two of the photographs, one in stylish black and white, the other also in black and white, however her eyes and lips were in strongly accentuated colours, green eyes and red lips. I loved that picture.

"That is you, right?" I asked.

"Yeah, that's me. It's one of the pictures taken during my first ever photo shoot. And someone from a make-up company liked me so much I actually got contracted for three ad campaigns by now," Rebecca said, with a hint of pride.

"I will introduce you if you want, they'll love the look of you. And of us potentially, they like contrasting hair colours in one image. Your red and my blonde will look great together," Rebecca said.

We sat down, legs brushing against the other's. Rebecca looked at me, and smiled. She moved in for a kiss, and the moment our lips touched I reckon we generated enough electricity to light up her whole house. I bit her bottom lip gently, she reciprocated by sucking my tongue. Eventually she broke the kiss off, her face still very close to mine.

"Please stay the night Carey," she whispered in my ear.

"I would love that," I replied, equally soft.

"I want to know you much better, and I want to make love to you. And I want to make it last," Rebecca told me, whilst her hands started to caress my legs.

"I love your fishnets. Are they tights or stockings?" she asked.

I stood up, showing the suspenders keeping my fishnet stockings up. Rebecca licked her lips, and ran her hands over my thighs, towards the black lace triangle of my panties.

"We will get to that later," she said with a smile that told me sexy times laid ahead, but that she would tease me at every opportunity. Which in fairness was no more than I deserved for standing her up online all those times.

Rebecca wanted to know how I got into cross dressing, and how on earth I had taken this long to come out of the closet.

"I was introduced, or seduced, by my flatmate, about 10 years back," I started.

"I had moved town for work, but I didn't have a budget to live on my own. So, I responded to an ad online. When I showed up I met Rob, who lived on his own after his girlfriend had left him. He needed someone to share the bills with. Rob was very upfront about the fact he liked dressing as a girl on occasion, which was exactly the reason his girlfriend had packed her bags."

"She had however left quite a stash of clothes behind, including lingerie and make-up. She did phone him a couple of times wanting it back, but he said he'd given it to a charity shop. He had only moved it to his own wardrobe and drawers," I said.

"We did what two guys that age might do. One drunken Friday night, we were too short on cash to go out. We got a bit drunk, and bored. Rob started making some silly suggestions, including watching porn. Lots of his stash was about lesbians and shemales, and cross dressers of course. And some threesomes, with two men and one woman, with both men fucking the woman, but also each other," I said, trying to read Rebecca's expression.

"At first we would just rub our cocks over our jeans. Then it was just our underpants, and soon our cocks came out. We would jerk off together, then clean ourselves up. I started to wonder more and more what it would feel like to be the girl rather than to fuck the girl," I carried on.

"Then one night after watching tranny porn, Rob wanted to wank me, and vice versa. What I had not noticed was his painted nails. So, when Rob started running his red nails over my cock I came within seconds, it was the sexiest thing ever. He then started to lick my cum off my chest, then started to suck me to make me hard again. I stopped him, and asked him to put lipstick on as well. He then sucked me, leaving red smears all over my cock, but he absolutely drained me," I said.

Rebecca was transfixed and clearly wanted to hear more, as her hands ran over her chest, massaging her breasts and nipples.

"I then did the same to Rob, putting on nail varnish and lipstick. His was the first cock I ever sucked for real, and he shot four loads deep in my throat. I couldn't swallow all of it, but we swapped the rest with a red lipstick kiss. The next day when we were getting ready to watch cross dressers porn, Rob asked me to wait. After an hour or so he came back, in a tight black dress, fishnet stockings with a seam, and in shockingly high heels. He had put make-up on, and wore his ex-girlfriend's perfume. He had even styled his long hair!" I continued.

"As he walked up to me, he told me to call him Bobbi, and he asked if I wanted to suck his girl cock, and then fuck him in his man cunt," I said, whilst looking at Rebecca.

Rebecca's hand was under her own dress, and she was clearly playing with her own cock. She took my hand, and placed it on the mushroom head of her fat cock. I told how I had taken Bobbi's cock in my mouth, sucking it hard and deep. Bobbi had cum loads in my mouth, then came over my cock, lowering himself onto me, and riding me hard. I had thrown him on his back halfway through, and then fucked him deep and hard, whilst his legs spread, with his heels digging in my shoulders. I have never cum harder than at that moment," I said.

"God that has made me so horny," Rebecca moaned.

"I can feel that," I smiled.

"You're big...I want all of that," I said, but Rebecca urged me to finish the story first.

"Well, I had already wanked him off, just as a guy thing. I had already sucked his cock and eaten his cum, more leaning towards a gay thing. Sucking him when he dressed as Bobbi only seemed like natural progression. The outfit and make-up were a nice bonus, and a very sexy touch I thought. He looked rather hot as a girl. I sucked his cock, and that was a 9 inch slab of meat! He came in my mouth, almost drowning me in cum."

"After that Bobbi asked if I ever thought about being a slut like him, just like watching the cross dressers and shemales in the porn we watched. I told him I did. Bobbi told me to suck his cock one more time, and then we would dress me up and he would let me be the slut," I went on.

"Bobbi had gotten some of his ex-girlfriend's clothes out to let me pick, and given I wasn't that colour conscious, he suggested a matching pink bra and lace and silk panties set. They were the first lingerie items I ever wore. And they changed my mind forever! I felt sexy, and horny beyond belief. The feel on my skin was like nothing I had ever experienced. We found a pair of pink stockings and a garter belt as well. Putting them on almost made me cum on the spot. The feel of stockings rolling up over your legs, especially freshly shaven legs, is the sexiest feeling ever," I said.

"Stocking fetish?" Rebecca asked.

"Still going strong," I smiled.

"Bobbi found a pink dress which just about fitted me. There were a pair of pink pumps, which were two sizes too small at least, but I was willing to suffer for a good fuck. I put lipstick on, and after letting me give him a twirl, Bobbi went down on both knees, and begged me to fuck his mouth, like they did to those trannies in the videos. I really didn't last long, and Bobbi swallowed what he could. We did a cum kiss, and then he wanted to fuck me. He lubricated me with cum and saliva, before filling with all nine inches of him. Even talking about it now, I can still feel his load shooting inside me. That was when Carey was born," I finished.

"Wow, that was something," Rebecca said, her eyes bright and sparkling with life and lust. "So, could you still take 9 inches? And why did Carey not venture out after she was born? Surely you should be celebrating her loud and proud!"

I told her that Bobbi was badly beaten up after being set up by someone in a chatroom. I was just too scared to let Carey face the world. I did take various martial art classes, and have black belts in several, so I could hold my own. I just didn't want to put myself in a position of police enquiries, or social media exposure. I had stuck with Bobbi, and helped him best I could, but he faded a bit. He needed time to regroup and wasn't sure if Bobbi would ever come back.

"That is such a bad way to be," Rebecca said. "Could you, or could we, try to find him via social media, maybe just reach out and ask how he or she is doing?"

I agreed to try and find out more, and see if Rob or Bobbi was interested in rekindling our friendship.

"And, in answer to your other question, I can handle upto 11 inches now, courtesy of some practice with my flexible friends," I winked.

"That's good to know. Just thinking out loud sweetheart," Rebecca smiled. "And what size do you pack?"

"Well, nine and a bit inches, but maybe the right pair of lips or the right pussy, could make me get a 10," I replied.

Rebecca's hand caressed my face, then she put her hand in the back of my neck, and she pulled me close. She kissed me, she kissed me hard, with a lust that unleashed years of pent up desire inside me. I returned the kiss, our lips and tongues hungry and needy. Rebecca climbed on top of me as she forced me back on the sofa.

"God you're beautiful. I want you so bad, I need to fuck you and I need you to fuck me Carey. I am so glad you went out, I was going crazy just meeting you online!"

With that the doorbell rang. Rebecca shot up, cursing whoever it was breaking up the moment. She tidied her dress, tucked her erection away, and did her hair before answering the door.

She let in her female guest, a rather attractive blonde, in her 50s maybe. She introduced her as Linda, and told me Linda was the photographer who made the portraits that were up on the walls.