A Night to Remember

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Story of a sissy’s first time out with Mistress.
2.9k words
4.39
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Part 1 of the 8 part series

Updated 06/11/2023
Created 02/09/2022
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Edit by dpga4625

First time i post a story here, hope you like it.

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This was going to be a special day, my heart exploded in my body, thoughts full of both excitement but most of all... fear.

How should I manage this evening? So, playing at home or at Mistress's was one thing, but to actually go out! Traveling to a BDSM club on a Saturday night?

At the same moment, a ping appeared, 'Hey slut! Ready for a cozy evening? I'm so proud of you to finally come with me out.'

These words did not make it any easier, I couldn't say no now! The thought of betraying my Mistress would ruin everything! No, I had to do this. I sent a message back. 'Hi Mistress, I have to say I'm a little nervous, but it's definitely going to be an exciting night I think.'

'Yes, slut, it will be an exciting night, a Night to Remember!'

Time felt like it was standing still, then the alarm sounded to go, which awoke excitement in me, time was right to meet Mistress. I'd packed everything I felt was necessary. After the drive, I was now ringing the doorbell of Mistress. The door opened slowly, there she stood, beautiful, with a warm seductive smile and a spark that made anyone want to kneel down at her feet.

"Hey slut, glad you came."

I got in quickly, my heart was pounding, trying very hard to stay as calm as possible.

Mistress came behind me, stroked my hair slowly, other hand sliding up along my thigh and playing between my crotch and ass. My eyes just closed from the pleasure. She moved slowly around me, hand sliding to the front of my pants where she slowly stroked fingers on my crotch. I noticed my shaft started pumping, it got stiff which caused her to stand with a wide smile. Leaning her lips right up to my ear, licking the earlobe saying, "I said this would be an evening you would not forget slut!"

I closed my eyes with pleasure, so delicious, so exciting as she kept sucking and giving me small bites on my earlobe. "Oh my, slut, are you horny? I said this was going to be special."

Slowly she started to unbutton my pants, she pulled them down gently. Her hand slowly felt outside my boxers, I was almost completely stiff out of horniness and pleasure. She grabbed the inside of my boxers, sliding my shaft out, slowly beginning to jerk my cock. Moving behind me, using small jerks, I could feel the now steel hard cock. Her other hand went between the globes of my ass, stroking gently to play with my hole. Slowly, she started to spank my ass, I jumped but again there was a slap, she just laughed again.

"Wait here, slut!" As she disappeared and returning quickly with a dildo in hand. She stroked it between my ass and balls, sliding it further between my legs, she stroked it slowly next to my cock. The dildo came up along my stomach up to my mouth. I did not hesitate, opening my now wet lips, I wanted it so bad.

"Kiss it slut!"

I made my lips ready to kiss the head of the dildo which then got a wet kiss, my lips opening up, my tongue coming out under the head of the dildo. Slowly. my lips started to take shape around the dildo. Still jerking me, feeling so delicious, I was in another world. I started to push more, almost right there, I was going to cum. That's the moment she stopped, coming behind me, holding her hand outside the dildo so it got stuck further into my mouth. She slapped hard on my ass again 3 times, slap, slap, slap, I shuddered in fear, I didn't get the dildo out, and she hurt my ass! She gently pulled the dildo out, smiled, and kissed me on the cheek. I said, "Why did you do that? It hurt!"

"Here it's me who decides slut! You are not allowed to come until I say so! Oh, from the slap you got, your cock has now become slack again."

I had not noticed it, wow... it has become slack again. She held out a pink cage which she slid onto my cock which was locked it in place and the key hung around her neck.

"Time to undress, slut."

I took off my clothes, folded them nicely, and put them on the bench which brought her smile back. "How smooth and nice you are slut, bend over at the dining table for me." My ass was now bent over a table, at the same moment she was holding something in front of me. A metal butt plug with diamond end. She laughed, greased my hole, first one finger, then two, finally the cold metal plug slid into me. "How sweet that you have become my slut."

She came at me with a smile, hand holding out a red thong panty with lace. I lifted my legs, slowly she slipped the panties into place. She found two silicone breasts that she attached to my breast, they actually sat in place of the vacuum. A red lace bra came on the outside which she fastened in place. She studied me," Hmmm how sexy you are." Then she found all-black tights with a wide opening in the crotch and all the way to the back of my ass, it was pulled in to place. "Sit down slut."

I sat down on the chair next to her, she calmly began to do makeup on my feminine face. She took her time, but came with big smiles that showed pride in the job. Red lipstick was the final face touch-up.

"Now you start and become a special slut."

She pulled a white slim fit blouse onto my arms which was buttoned in place, the top two buttons left open so the breasts in the bra could appear a little. I lifted my legs to get a black leather skirt that tightened well on my ass but didn't cover more than a little over the ass edge. I got a black leather corset in place, which tightened well around my stomach and my breasts making a beautiful bulge. She then helped me with some boots that went up to my knees. I would probably say I was lucky not to have a high heel. The final finish was a wig with curls in dark brown half-length hair over the shoulder. She smiled and studied me, she guided me to her floor mirror where I could see my whole body. It was not possible, it was not me, I was so sexy! I wanted to fuck the girl I saw in the mirror!

"I know you would like that slut, now I'll just put on something, then we'll go to the club... slut."

She disappeared with laughter. I was so hung up on myself, I was so sexy! I stroked my breasts, my tight ass. It started to push in the cage. Suddenly Mistress was ready. She gave me a short leather jacket that would match, then she took me by the hand and we left.

After a quiet and more or less alone train ride, we arrived in the city where there were more people. Fear built up, no this was not good, what have I agreed to! "Come on slut, it's not far."

I got up; eyes narrowed a little thinking, 'Look how many people there were. My God, I can't go out here!'

"Come on slut, I know you can do it. Either way, you look so sexy."

I squeezed my eyes together, exhaled, gathered what I had of courage, and my legs began to move little by little. We walked together into the train hall, a lot of people walked past us, I noticed a bunch of boys in their 20's whistling at me, making my body go hot, my self-confidence builds up as I started walking more straight backed. After some walking, we finally came to a building. Mistress just smiled; she called the doorbell, the door opened with a guard standing inside the door

She hung up and went inside. There were a lot of people there, they were dressed in such incredibly sexy things, which lit me up, seeing all this was something completely new, completely unreal. Seeing the beautiful butts of other Mistress' women, girls, Daddy's and Masters. Suddenly there was a slap on my ass, I could not help but splash red in my face. Mistress looked at me.

"Slut, it's not nice to be staring, not too much at least. Come on, you're gonna greet some people."

Mistress took out a collar which she fastened around my neck; I could see a glowing smile appeared in her. After a lot of talking and greeting new people both men and women, we went to a private room. The room had a sofa, a table with lots of fastening links, a kind of stand with fastening cuffs for legs and arms and much more. Mistress came towards me, she moved so slow like time stood still. Her eyes stared straight at me, lighting up kind of seductive, it felt like time stood still again. Her lips just passed mine and kissed me on the neck and stroked my ass.

"Now slut, do you want to be allowed to come today?"

"Mmm yes Mistress...."

"Fine, if you do what I command you, you will be get a blow job

afterwards."

"Yes mistress, I'll do anything!"

She came at me with a wide smile, "Okay slut, time to work a little, do you see what's on the wall?"

Eh, I swallowed a little heavy now, "Yes I see it... it says gloryhole."

"Good slut, you know what to do, start and use your lips."

I was skeptical, scared, but she looked me deep in the eyes and smiled, kissing me on the cheek again. "Do this for me slut, then you will have an orgasm you will never forget."

Slowly I sank on my knees, down onto a flat pillow in front of the hole. I looked at Mistress who was smiling, you could see she was bursting with joy and excitement. It did not take long before a dick suddenly appeared. I shrugged a little, my eyes went back to Mistress who just gave me a smile to a nod as a sign to get to work.

I slowly started to stroke the cock that was just sticking out of the hole, slowly I started jerking it. I noticed the dick became stiffer. I started to kiss the head of the dick, opening my mouth, my tongue slowly playing with the cock that was in front of me. Slowly, my tongue moved back and forth, rolling the tip of my tongue around the dick head. My lips opened, red lips forming around the stiff cock that now stood in front of me, I started to suck him. Calm movements back and forth, while I slowly jerked him. Working efficiently, I noticed the dick of the stranger was completely stiff creating a feeling of pride, so my pace increased, it did not take long before he was on his way to cumming. I just jerked him off before he got into a proper squirt. The cock disappeared while I calmed down a bit.

Mistress now stood by my side, she looked down at me, "So good slut you are, did you get aroused by this?"

I was quiet... she ran her finger under my chin to lift my head. "Yes mistress, I was excited."

"Nice slut, will slut suck another?"

"Yes mistress, please!"

"Okay slut, but you have to promise me to try to swallow a little, deal?"

"Yes mistress, I will try." It did not take long before another dick appeared. A little bigger this time but perfectly fit. I started jerking it, it didn't take long before I licked the stiff cock. I was faster, more eager. My lips quickly formed around the now stiff cock in front of me working it well in and out, I made a good effort to go deeper and deeper. I noticed it now when pumped in his cock, he was about to come. I jerked him off and had my tongue ready to do what I had promised. I was going to swallow another man's cum for the first time. He came in a real splash, it hit my tongue that was out, the rest hit around my lips. I got my tongue in and I swallowed what I could. It was a little weird because I actually came with a moan!

"Look here yes, the slut is with me too, I hear."

She stood by my side, stroked my cheek, smile coming to her face as I got a feeling of pride, or maybe I just wanted it? Had she just opened the door for me? Let me experience my own pleasure?

She took me by the hand, led me to a bench, bent me down so my stomach was on the bench. My ass was in a full doggy style, I felt that I must look like a really cheap whore in a porn movie. She came in front of me, squatted down saying, "Now slut, I'll play with your pussy hole, but the question is.... Should I fuck you, or would you rather be fucked by a real man."

"You Mistress...."

She just smiled, "Okay, I can, but next time you must take a real dick, Slut."

I noticed I was getting hot in the face, clearly blushing. She was now standing behind me, slowly lifted my skirt, pulled my panties down to my knees, my ass now naked. There were some slaps on my ass that actually made me moan and make some pathetic moaning tones that would have been on a porn movie. She stroked my ass gently, then slapped it again. Then she gently pulled my metal plug out. A new layer smeared on my butt, clearly lubricant. Slowly a finger was pushed into my ass, then two and three, I just moaned, horny as hell.

She was playing with me which I noticed she enjoyed every second. Slowly she pressed a dildo against my hole sliding gently into me. Slowly it went in and out, back and forth. Getting deeper and deeper each time, when it slid all the way in, it hit my prostate which caused me to shake and tremble with pleasure.

I moaned. She fucked me now calmly but in a steady thrusting. I just moaned more and enjoyed every second of it. She kept going, spanking my ass, suddenly grabbed my hips, and really pushed it in, I started screaming with pleasure, I had never screamed so much! I didn't know if it was a feeling of pain, pleasure or simply an orgasm that built up, it being a whole new experience. I could barely say I was on my way to cumming. She gently pulled out the dildo, grabbed my arm, and pulled me up. She took me to a tripod shaped like an x, clearly made of thick wood. There were arm cuffs upstairs and leg cuffs on the bottom. She fastened my arms in place as well as my legs. She studied me and just smiled.

"Well, slut, you must have been pretty good today. I'm going to keep my promise to let you cum, do you want a blow job?"

"Mmm yes, please, Mistress!" I glowed, "I want to cum!"

She smiled, slowly and gently she loosened my cage. It slid gently off and the over horny dick popped out. Slowly she jerked it, lubricated it with lubricant, played with it. "Well, you will get your blow job... slut"

I just smiled, at the same moment the door opened, another girl came in. In fact, after more study, it was another sissy slut, actually quite sexy dressed in some sort of school uniform with a skirt! I was terrified where I was padded. I just looked at Mistress with a disturbing look. "You did not think I was going to suck you?" She just laughed... "This slutty sissy girl is going to give you your well-deserved orgasm."

The sissy girl sat on her knees in front of me, she slowly stroked my cock, played with it, which only made it stiffer. She looked me in the eyes the whole time as her lips opened, they formed around my cock in a pleasure I had never experienced. I just moaned, so delicious, so exciting, I no longer cared what it was, it was just heavenly. She made it an absolutely fantastic pleasure, feeling her lips play up my dick, getting jerked off, played around the dick head... the moaning just got more and more.

The girl smiled, she got up and pulled a condom on my cock. She smeared a thick layer of lubricant. She turned, lifted her school skirt and pushed her panties aside. She pushed my cock into her hole. The sexy sissy was now doggy fucking me! I just moaned, I could not move since I was attached, frustration spread in me! I came in a real splash, moaned and moaned; the girl looked at Mistress but her words were just...

"Don't stop, fuck my slut."

She smiled and just kept going... I started screaming in orgasmic pain, now it hurt! Stop, stop! She finally did, slowly she pulled the dick out, slowly slipped the condom off and sucked me clean.

She just smiled at me, got up, and gave me a juicy heavy kiss.

"Thanks for the help slut, you can go."

I was completely exhausted where I stood... What had really happened to me today?

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