Flash in the Night

It was finally happening.

My wife was going away for a weeklong business trip.

In the last 5 years I got into crossdressing. I have an extreme fetish with stockings and high heels, which my wife is not really keen off. I started by trying on some of her stockings when I was alone in the house but gradually, I evolved into a proper crossdresser.

I started buying my own kinky clothes online and trying them on any chance I had when alone at home. I was always getting very sexy "fuck me" high heels, much higher than any shoes my wife ever tried, hold up stockings or garters in any shape and colour. Panties I sometimes tried from my wife's drawer as I thought that was kinkier. I had tried several different options for dresses, but my absolute favourite was a red tight dress that made my figure quite feminine or a kinky maid's costume, full with apron, bows etc.

Most of the times I had a couple of hours to wear my sissy gear before my wife was back from work. So, you can imagine how excited I was in the prospect of her being away for 7 full days.

I dropped my wife at the airport and made sure she left when I made my way home. I have read a lot of stories and sissy captions about hubbies getting caught by their wives but that was not a fantasy that I wanted to explore. I was way too scared to lose her.

Once in the house, I almost run to my closet to take out the "sissy bag", a nice backpack where I kept all my sissy clothes safe. I took out everything and put them on the bed and then I grabbed some things with me in the shower.

The water felt very warm and weird running down my now smooth legs. I have never had smooth legs before. I knew there was no time for hair to grow back in 7 days, but I decided to do it anyway and tell my wife I was trying out some hygiene trim bullshit excuse. The feeling was so strange, but I already started getting hard. I made sure all my body was baby smooth and I applied some cream.

I spent a lot of time in the shower with an enema head that I bought as I wanted all my dildo play to be very clean, like an anal pornstar.

When I went out of the bathroom, I was smooth like a woman, body glittering from the cream, nails polished bright red, and a nice clean, empty feeling in my anus. I was standing in front of the bed looking at my clothes.

For my first day of the week, I wanted to go kinky and I had chosen the maid's costume, a pair of white hold up stockings with matching garter belt, pink panties and matching pink stilettos.

First, I put on the costume, adjusting the belt, tying the bow and fixing the kinky apron. Then it was time for my ever-favourite part. putting on the stockings! I sat down at the edge of the bed and made sure to slide each leg slowly and in a very sexy way in the hold ups. I have read it in forums, but the feeling of smooth legs in stockings... it is another level of feminisation.

I was starting to get hard which I did not want to happen because of the next item in the list. In anticipation of the week, I bought myself a cock cage. I wanted to lock myself for the week and make myself really horny for when my wife was back. I put the cage on. I thought that my cock was going to break in two and it felt extremely tight in there. But I could already feel how this would make me hornier by the minute.

Standing up, I put on the high heels. The mirror in front of me was telling me that besides my masculine face, the rest was an extremely passable sissy girl.

FLASH!!

What the hell was that? I thought. It came from the window. The curtains were still on!! In my heat I completely forgot to close them. I run and shut them. I peeked outside. There were no lights to be seen and it was raining. It was a thunder I thought.

I managed to relax after a few minutes, making myself sure that it was a simple thunder from the rain.

In full sissy attire, there were a couple last things to fix. I started toying with my butt for a bit and then I inserted a medium sized butt plug. I wanted to start stretching my asshole while I was going to fix my makeup and wig.

...And Done! I look at the mirror. Now in full make up and blonde ponytail wig I was really a woman. I could not believe at the sexy - or should I say very slutty girl - that was looking at me through the mirror.

I stood up and went to the living room, walking in my heels made me feel so horny. I connected my laptop with the TV and broadcasted some high-quality sissy porn on the screen. It was time to have some fun.

DING DONG!! the bell rung.

I was completely frozen. I tried to stay still and make no sound, hopping that the porn sound from the TV would not be heard.

DING DONG!! again ...

...

BANG BANG BANG!! someone was really knocking on the door.

I was getting afraid that the next-door neighbours would hear the noise.

"Luis!" I heard a voice shout. It was the neighbour from across the road. We have met each other on morning jogs. He is an instructor and has helped me with some exercises in the past.

"Luis, it's me Mike, I know you are in, open the door."

I was not going to open the door dressed like a sissy maid. So, I decided to pretend to be away.

BANG BANG!

"Luis, I know you are in, check your phone now!"

He was going to wake up the whole building. I reach for my phone and saw that I had a message from him. I open my inbox and I see a picture of my room, with me in sissy clothes fixing my garter belt, caged cock in full display.

It was a flash from a photo, it was not a thunder, was my first thought... FUCK!! was my second. what was I going to do now?

At that moment, I received another message.

"Now that you read the message, I know you are in and you need to open the door if you want this picture deleted."

I walked to the door and unlocked it. I was too scared to open it though as I was completely dressed and ashamed. Mike pushed the door open, making me lose balance in my high heels and fall on the ground.

"HA, look at you Luis, I mean, I always thought you had a small frame, but seeing you in these clothes, with the wig and make up, if you didn't give me a full dress up show from the window I wouldn't believe it's you."

"Mike... it's not.. I am just fooling around; I am not gay or anything ... I did not give you a show... I forgot about the window."

"Is that so?" he said as he walked and sat down on my sofa. "Your choice of porn seems pretty gay to me, and the fact that you are one of the sexiest sluts I have seen, well, it is not really manlike Luis. Or should I say LUISA!"

I was still on the floor, in shock and could not move. Mike took his phone out and took another picture of me, now from up close and from inside my living room.

"Listen up Luisa, the way I see it, you have two choices. Either these two pictures are delivered to your wife's phone or you do as I say for an hour and then I will delete the pictures and we will forget about this incident."

"My wife?... no.. Mike, please, you can't do this... She cannot find out about my fetish!"

"I don't want that either Luisa, so I guess you choose option 2?"

Still on the floor, I simply nod. Considering my options, I cannot let Mike send those pictures to my wife. She will never understand my fetish and she will break up with me. So, defeated, I nod.

"Good girl, now let me tell you how this night will go. I will forgive you this time only, but from now on you will answer my questions with - Yes Master - and you will do exactly as I say. Do you understand Luisa?"

Dressed up like a slut, my sexy makeup and wig must look really funny to him as I matter, "...Yes Master."

"Good. Ok your first task is an easy one. I like how you are down on the floor. Now be a good slut and get on your knees and crawl all the way to me."

I bring myself together and gather my strength and start to crawl towards him.

"Do it like you mean it slut!", he shouts and takes out his phone again, pointing at me. "Don't worry Luisa, we will delete them all at the end, if you are a good and obedient sissy. Now crawl like a sexy woman like you would."

I arc my back and stick out my ass as I crawl to him, making sure I wave my buttocks with every step. I reach the sofa just in front of him and start getting up.

SMACK!! He slaps my face.

"Did I tell you to stand up Luisa? Continue like this and all the pictures will go to your wife!"

Still shocked from the slap, my mind is completely full of his threat and I don't realise how easily I say "oh please Master, I will be an obedient sissy from now on."

"Good, that's what you will be. Now, I see that you have put on a very sexy red lipstick. Well Luisa, there is only one reason to put on red lipstick and don't deny it, you fantasize of sucking cock, don't you, you pathetic sissy? Well, you are very lucky." he says as he puts down his sweatpants.

an amazing black cock emerges - oh did I mention that Mike is black? - It appears to be 8" while still not hard.

"Now show me what all the hours of sissy porn have taught you Luisa."

I cannot deny that sucking black cocks is one of the most common captions and porn that I search when I want to touch myself but having a live black cock just inches from my face as I am fully dressed is quite something. I am very scared, but I can also feel something that can only be described as excitement growing in me.

I grab his big cock and lift it up. It is easily twice the size of my penis. Well, now my penis is a little limp prick in a cage I think in my head.

As if reading my mind, he says, "Admiring the size of a real man's cock you little sissy? I am sure you will find out that it tastes as nice as it looks." He grabs the back of my head and buries my face under his balls. "Lick my balls and rim my butt Luisa. This is your first lesson on how to worship Master's cock!"

The manly smell and his brute force are taking control of my mind as I start giving him a rim job. I am licking his balls and all the way down to his asshole. I cannot believe that I am doing something that a few minutes ago would seem so repulsive as a man, and it actually makes me feel horny. I am glad that I am in a cock cage as I wouldn't want him to see me get hard from doing this degrading act.

"Enough foreplay, time for the main act Luisa", he says and he releases his grip on my head. I go back a bit, still his cock in my hand and as I lift my eyes, I realise that his phone is in his hands and he is filming me. On my knees dressed up, my fingers wrapped around his cock, looking straight into the camera. He promised that he will delete them all if I do as he says so I just try to play the part.

I give a good few licks on his now erect and easily over 9" cock and then I open my mouth. I take his cock head in and suck it for a few moments.

"That's good Luisa, but if I wanted to have my cock kissed, I would hook up with a lady. A sissy like you needs to learn how to deepthroat. Now, I know you are new to this and I will not push you hard, but I will give you an incentive. If you don't take more than half my cock in your mouth by the next 2 minutes, I will press send on these pictures."

I am not sure who is taking over my mind as I hear myself say, "Yes Master, thank you for giving me a chance Master." and I put his cock in my mouth.

In the next couple of minutes with a lot of gag, pause, gag and effort, I get half of his cock in my mouth. His hands grab my head and push me 2 inches deeper.

"There you go, consider this a helping hand sissy. You are safe.. for now. This will do just fine." he says while laughing.

I feel him standing up, his grip still strong on my head as I struggle not to gag. Now standing, he starts fucking my face. I can feel saliva and precum running all over my chin and my face while my eyes are watering. I am sure I look like one of this cheap pornstars that are being throated and degraded. I sure feel like one.

He suddenly stops. I am both relieved and disappointed. Am I really enjoying this? He lifts me up and throws me on the sofa and tells me to lay on my back and hang my head over the edge. He comes over and mounts my face.

My mouth starts hurting while my face is a complete mess by now. I cannot even open my eyes as they are full of precum and saliva. His heavy balls slamming my nose and forehead with every thrust. Does that mean that he is all the way in? Did I manage to deepthroat all of it, I think to myself and I realize that I feel proud.

"You really enjoy this you fucking slut don't you?" he says, and I realize that in this position, my skirt is lifted and he can see my caged cock that is now dripping a lot of precum.

It was different before when he was "forcing" me to obey and satisfy him, threatening me with his pictures. Now he knew that I was actually getting horny from being facefucked and degraded.

"Get on your knees and open your mouth and get ready for your sissy baptism!" he tells me.

I jump of the couch like an eager slut, get on my knees and open my mouth as I look at him. He takes his phone from the table as I realize that he has been filming my facefucking all this time and he points it at me.

"For your final task, show me how you want my cum. Beg for it and if you make me finish I will delete all the pictures."

By now I don't really need the threat but I act as if I do. I look straight in the camera and say, "Please Master, give this sissy whore your precious cum.. let me feel it on my face and in my mouth and let me swallow it."

He must have been at the edge because by the time I finish the sentence a rope of thick white cum splashes over my face. I quickly open my mouth to catch the second shot while he sticks his cock in my mouth for the rest. He stays in my mouth for some time as I clean him well with my tongue. He pulls out, gives me a few cock slaps and then a couple soft slaps with his hand. His phone always pointing at me.

"Well, wasn't that just nice?"

"Yes Master, thank you for your cum!" I say, thinking that I should still address him as Master and still be in role for him to delete the pictures.

As I am still on my knees, my mouth aching and can't really understand what has happened, he stands up, lifts his sweatpants, gives me a pat on the head and moves to the door.

"That was a good performance Luisa, almost as good as my fleshlight." He tells me, while I feel humiliated that I compared to a sex toy, and also angry that I come short in the comparison. "I am going home now and will use your pictures to wank tonight and will delete them all afterwards. You deserve it.", and he leaves.

It takes me some time to stand up. I stay there soaked in cum and saliva and feeling really slutty. There is still sissy porn on the TV which makes me really horny to touch my caged penis.

Before I manage to do anything my phone rings, it's my wife.

"Hi honey, I just landed. I miss you already. I hope you are not feeling too alone at home without me."

I try to compose myself as I speak to my wife on the phone while dressed as a sissy with Mike's cum still on my face. "I will be fine baby, don't worry about me. Mike was actually here. He showed me some new exercise to practice at home. He just left." is the only thing I could say.

"Have to go now. Love you!" and she hangs up.

My phone still at hand I receive a media message from Mike. It's a video of me begging for his cum. "I deleted all the photos as I promised Luisa, but I didn't say anything about the videos!" it reads.

WHAT THE HELL! I think.. he now has videos of me and won't delete them. This is really bad. I know that if I threaten him it will go really bad for me so I try to play it the slutty way. "Oh naughty Master.. what do I have to do to get you to delete those?" I can't believe I wrote this, but what other choice did I have?

"You filthy slut!! Well, tomorrow evening when your wife is out, dress up and invite me over. I am sure we can figure something out."

What I did next must be one of the stupidest things I've ever done. Instead of letting him think that he can meet me tomorrow when my wife is away, I tell him - "My wife is away for the whole week!"

"In that case, let me grab some things from my flat and move into yours for the week. Call in sick at the office. You will get to be my weeklong sissy pet." he says, attaching a snap of my face full with cum. "Don't even think to deny me!"

- To Be Continued -