A Night of Her Dreams

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A crossdressing sissy gets used by an attractive couple.
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-based on my real experience-

As I am making my way to their house, I remember the months I have been talking to them and how I have longed for this to finally happen. I have done this kind of meet up before but it's been almost two years since my last time. I don't meet people as often as I say I want to because I am very scared to. I often worry I wouldn't look pretty in the eyes of others, and of course the fear of being exposed. But something about them made me sure that I didn't have to worry so I decided that I wanted to do it. It was only a matter of when and that time is now.

They told me to be at their door at 7pm. I got off at the bustop near their place at 6:30pm. It's a 10mins walk so I get some water from the convenience store and wait there nervously for 20 minutes. I want tonight to go well so I have not eaten anything since last night, and spent all day cleaning out my "pussy" a dozen times. I have a buttplug in my pussy and I have a bag with all of my girly stuff in it. Nobody passing me on the streets would know what I am about to do.

It's time, and I walk to their place. I arrive and I text them that I'm downstairs. I nervously wait until a man opens the door for me. He is a really big, attractive, masculine man, one like I have never been with before. I have sucked three different guys in my life and they were all very average sized with average level of attractiveness but the man I am following after at this moment is a real man with arms that I am sure could lift me up without any difficulty. He is to be my Master? I scream to myself inside with excitement under my panties.

I follow him into his apartment and he points me to where the bathroom is. I take off my shoes, and then I see a woman entering the living room and immediately, I am shocked how beautiful she looks. She is everything I have always wished to be. We share greetings and she hands me a drink and I enter the bathroom. My excitement grows after seeing my new Master and Mistress. I have to impress them tonight, I think to myself, if I want to be their slave they would want to keep.

In my life, prior to this night, I have sucked three different men (first two for only one session and the last one for two sessions), they all told me what a good cocksucker I was but I have never let them fuck my pussy. I was always scared and was never ready to have a real cock inside of me. I played with a couple once which was with that last man I sucked off. He had a female partner, and all we did was that he fucked her pussy and came inside her and made me lick his cock and her pussy clean after. I wished we did more but I moved to a different city after so we never met again. After that, I have served two different women (both of them for one session only). One, I served by worshipping her pussy for hours and she fucked my pussy with her small strap-on dildo so it wasn't very challenging. One, I served by being her tease and denial toy. She was very much into teasing and denying me for hours and fucking my pussy with a 6inch dildo of mine. 6inch dildo is the biggest one I've had in my pussy so far but all that is about to change tonight.

Back in the bathroom, I start getting changed. I have a lacey pink and black panties, a pink bra, black thigh highs, a white blouse and a black tight mini skirt on. I put on my favourite black heels, put on my makeup and a wig. I am not very good at makeup and wish I was more skilled. I wonder for a bit, if I could ask the Mistress outside to help me with makeup but I don't want to bother her. I am here to serve them. I look at myself in the mirror one last time. I am ready. I take a big sip of the drink. I knock the door from inside the bathroom to let them know I'm coming out.

I see them sitting in the living room. Still unable to believe how attractive the couple looks and how lucky I am to be their slave tonight, I walk towards them nervously and sit next to the Master on the couch, with Mistress sitting on the coffee table across from me. They ask me my name and I tell them "Haley".

"Wow you are gorgeous", says the Mistress.

"Thank you", I respond shyly.

"She is really cute", the Mistress says to the Master.

"Yeah, this is my present for you", the Master responds to the Mistress as I start to blush.

"Yeah? Well, Haley, how submissive are you?", the Mistress asks me.

I wanted to tell them that I am probably the most submissive girl they will ever find but being a shy girl, I only mutter out "very".

The Mistress still seems to like this answer, gets up and says "yeah? Then we will have to test you" and she goes into her room.

She comes back out with a pinwheel. My excitement grows as my panties start to get very wet. I have seen this on the internet before and I have always been curious to try. This would be my first time. She runs it along my sensitive inner thighs. Does she know my inner thigh is one of my erogenous zones? I love the feeling of it. So I tell them that I like it when they ask me if I do.

Next they instruct me to stand up and the Mistress sits on the couch next to the Master. They tell me to turn around so they can have a look at me. I can hear them talk about me as if they were at a shop observing the good and it turns me on even more. They caress my thighs and my ass with their hands and feet, telling me to open my legs wider. I am loving having their hands and feet all over me.

The Master says to the Mistress, "have you ever seen a girl like her?"

"No, she is really gorgeous and cute", Mistress responds.

Their conversations are making me both blush and wet. The Master then faces me towards them and whispers to the Mistress, "this girl is very special"

"What is so special about her?", asks the Mistress.

The Master guides the Mistress' hand to my clitty and takes off my panties. My clitty springs out of my panties, making me embarrassed. They talk about how hard and wet I have already gotten and put back on my panties.

The Master tells me that one of my jobs is to serve his cock for the Mistress. He gets up and takes off his PSG shorts and his cock is bigger than any cock or dildo I have ever seen in my life. It seems about at least 8inches long but its thickness is what has me in shock. He has the most handsome, thickest and hardest cock. A cock I have dreamed of all my sissy life.

The Mistress says she is going to show me how a girl should suck a cock. She gets on her knees in front of the Master and starts sucking his cock while I stand there and watch, learning from her skills. It looks so fun I can't wait to give it a try myself. She then gets up and tells me to get on my knees in front of his cock. I get on my knees in front of him and the Mistress sits back on the couch next to us. I am an inch away from his cock which is glistening from the warming up it has just received from the Mistress. I have my hands behind my back and slowly take his cock into my hungry mouth. My first real cock in years and it makes me realise what I have been missing out all these years. I love cocks and I'm a cock sucking whore, it is ingrained into my brain as I move my head up and down my Master's cock, dancing my tongue under his shaft. Mistress holds my head and guides it in and out of his cock until I have everything down my throat. I am pretty confident with my deepthroating skills but a cock this long and thick is testing my skill. I want to say that I'm still doing a good job. They make me deepthroat several times and already his cock is covered with my saliva which the Master rubs all over my face.

I hold my heels behind my back as the Master begins to fuck my mouth and the Mistress feels my body up behind me, commenting how good I am at sucking a dick. The Master pulls his cock out of my still hungry mouth, I have some tears forming up in my eyes from choking on his cock. They now sit on the couch and I am facing them kneeling on the floor. The Mistress sits back, takes off his panties and tells me to lick her pussy. My hands now cuffed behind my back, I lower my head slowly and start gently worshipping her. Soon, my face is buried between her legs, as I continue to lick her pussy. She slowly moves my head down and tells me to lick her ass. I eagerly lick her ass and my nose is buried in her pussy. She squeezes my head with her thighs for a bit and lets me go. They both look amused with what I do with my mouth and say they want to see what more I will do with my mouth.

The Mistress lifts her left foot and puts it in my mouth. I lick every inch of her foot. The Master says "wow she will just suck anything we put in her mouth" and puts his finger into my mouth which I instinctively suck. He comments how soft my tongue is and the Mistress puts her fingers in my mouth too. I suck them while looking both of them in the eyes and then the Mistress puts her right foot in my mouth and I repeat what I did with her other foot. She puts both of her toes into my mouth as they continue to sound amused at what a slut my mouth is.

The Master gets up, and goes to the kitchen to get a drink and I am left there alone with the Mistress to once more serve her pussy and her breasts. The Master comes back and they tell me to follow me to their bedroom.

They uncuff my hands and I get up from my knees and walk into their bedroom after them. I get on my fours like a dog on their bed. They take the buttplug out of my "pussy" and the Master stands in front of my face and I start to suck his hard cock again. The Mistress behind me is getting my pussy prepared. They cuff my hands behind my back again and the Master grabs my head and starts to fuck my face. He lets go off my head and I just fall deep into his cock, choking on his cock, unable to lift myself up. The Master does it a couple times more. I love feeling helpless like this.

Now, it's time for the real fucking. The Master stands behind me, they put some lube over my pussy. My pussy is about to have its first real cock inside. The Master starts to push but it hurts. It is so thick and my pussy is not used to that level of thickness at all. They are very kind and patient though. They take their time in stretching my pussy and the Mistress holds my hand as the Master slowly pushes his cock in. I feel proud that I got everything in and the Master starts to fuck me. However, it is now the length that is giving me trouble as I seem to have a rather shallow pussy, or just a pussy not used to 8inches of cock yet. He fucks me slow so I can get used to it and the Mistress sits in front of me with her strap on dildo and I suck it for a little bit too.

Now, it is the Mistress' turn to fuck me, they switch sides and Mistress starts to enter my pussy and the Master slides his cock into my mouth. Being spitroasted has been one of my biggest fantasies and it has finally become a reality. Mistress fucks me gently first while I am sucking the Master's cock, but every time, I deepthroat and choke on his cock, my pussy pushes the Mistress' cock back against my will. They realise this and I feel bad that I may have disappointed them.

The Master takes his turn in fucking my pussy and I am slowly getting used to it and the Mistress takes her turn again. They start to fuck me faster and harder.

I love having their cocks inside of me, I would bend my legs to hold their legs to keep them in. When Mistress is fucking me harder and harder, I cry out "it hurts" but my legs are holding her tight so she wouldn't be able to stop fucking me. She realises it and says how I am saying one thing but my body is saying another and she says "oh it hurts but it feels good so I shouldn't stop?" and she continues to fuck me harder. She is absolutely right, I don't want them to stop.

The Master brings a mirror in front of me so I can see my face when I am getting fucked. I see a little girl with messy hair, tears in her eyes, slutty eyes, getting fucked by either my Master or the Mistress. It turns me on even more. I lose count how many times they rotate in fucking me. My face and tongue rest on my Master's cock, inhaling the masculine aroma of a real man as the Mistress fucks me hard and the Master would tell me to keep working on his cock. When my Master is fucking me, he buries my face to the bed.

The Mistress slaps my ass and thighs hard and being the pain slut I am, I really love it. She probably sees this and her slaps get harder. The Master comments that it must be painful. He is right but I love it and I want more. The Mistress slaps my face a couple times and chokes my throat softly once. I am in ecstasy as they continue to rotate in fucking and abusing me. They roll and move me around and my mind has gone blank. I just let go of myself, as they continue to fuck me like I am a brainless sex doll. They give me breaks in between too, which I feel grateful for.

They show me at one point another bigger dildo during a break and say that I will eventually learn to take it. I feel scared but at the same time excited to take it all in my pussy and make them proud of me one day. The Master asks me whose cock I like better, his or hers and I can't answer because I love both but I have been asked a question so I must answer but I don't know how and mutter softly, "both". The Mistress says that it must be like choosing between daddy or mommy. I felt embarrassed about a cock being compared to a daddy or a mommy but for some reason, that embarrassment soon turned into an excitement. It makes sense because I am a slave for cocks.

After some fucking they did to my pussy until my legs shake and my whole body trembles, they begin to make love with me laying at the bottom. I lick his cock and her pussy as they fuck on top of me and the Mistress is playing with my clitty.

It makes me cum all over her hand and when they are done fucking, she gets all the cum on her hand and feeds it to me. I lick her fingers covered in my cum and swallow. She then rubs her fingers on my face and on my thighs.

I am just laying there, with a blank mind and the Master and the Mistress begin to fuck again while I watch. I want to join in and lick their cock and pussy or their feet or fingers again but my body is still trembling and this is their time so I don't want to be rude.

After they are done, we cuddle together on the bed. The Mistress on the right side of the Master and I lay on the left side of the Master. I rest in his muscular arm and chest and I just want to fall asleep in his arms. My mind has gone completely blank but the good kind of blank. We chat for a bit and they hand me a towel to shower.

I get up from the bed, my legs still shaking. I pick up my panties on the floor and walk into the bathroom. I look at myself in the mirror, and I am a mess. I have dried cum all over my face, makeup almost gone, hair in a sticky mess. I regret not taking a selfie of that beautiful mess they have left me. I shower, get changed and walk out of the bathroom. The Mistress has already gone to her home. I say goodnight to my Master and make my slut self back home with the legs still shaking.

It was the best night of my sissy life. A perfect night that I, and my pussy, won't forget for a while. All I can think of now is, I hope they liked me, I hope I didn't disappoint them, I hope they would want to see me again, I hope they would keep me as their slave.

For three days, my pussy stayed sore but a craving for their cocks grew more and more. I will have to practice and become better so I can take any size of cock they decide to fill my pussy with.

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