Nicki's First Time

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"Now, put these clothes on and be careful putting on your stockings" Amy gestured towards the bed on which she'd laid out Nicki's clothes. Nicki saw that together with the stockings she had black panties and bra with inserts, a red sheer blouse and best of all, her black Latex skirt. Nicki put them on, not without difficulty but she finished and then stood in front of her Mistress. Her black latex skirt clung to her thighs just above her stockings.

"Sit down on the chair again, and let me put your wig on."

Nicki did so; she crossed her legs automatically as Amy slipped the long brunette wig on to her head. Nicki found that the wig completed her transformation. She felt like a woman, she wanted to enjoy being a woman.

"Now pose for me." Amy took out her camera and snapped several pictures. "I think I'll do some before and after shots," she smirked. "And, if you don't do exactly as you are told tonight or if you let me down in any way, I will send pictures of what happens tonight to Peter, do you understand?"

Peter was Nicki's boss and Nicki again shuddered when he thought about how Peter would react to the pictures that Amy had.

"Now come on, we've got places to go and people to see, get your shoes on, we are going out."

Nicki stared at Amy; she had thought that they were staying in the room.

"But I can't go out like this! It's still light and this skirt doesn't even come to the top of my stockings!" Nicki knew it was pointless to protest but she was shocked by what Amy had said.

"Ha, yes that's true. But then again, you are a slut so you should enjoy it! Stop arguing, get your shoes on and be grateful I don't put you on a lead."

"Where are we going?"

"Never mind, just get ready. I'm getting tired of your questions, slut." Amy glared at Nicki "Are you trying to irritate me?"

"No Mistress." Nicki obediently put on the black shiny high heels and stood up. She followed Amy out of the room wordlessly. Amy handed her a red clutch bag.

"If you need to re-do your make up then use what's in here, don't worry there isn't any money in there."

Nick glanced inside, no money, just some lipstick and blusher. She wondered what was going to happen to her this evening. It was so uncertain; she had no idea at all and was placing all her trust in Amy. She walked carefully down the steps into the Lobby, a few steps behind Amy who was carrying Nicki's bag of clothes. Amy walked over to the front desk and handed the bag to the receptionist, Julie. Nicki could see them talking when Amy gestured over to Nicki, they were both laughing. Nicki watched Julie get up and take the bag into another office.

Amy walked back over to Nicki grinning like a Cheshire cat.

"What's happened?" Nicki asked fearfully.

"Oh, nothing really," Amy said "I just told her that the bag contained all your male clothes which you no longer needed because you loved dressing like this. I told her she could keep them or dispose of them, give them to a charity shop if she wanted."

"What!" Nicki couldn't believe what she was hearing.

"Don't talk to me like that slut." Amy rounded on Nicki "if you give me trouble, I'll send those photos to your boss and your wife. Maybe if you are good tonight, I will get the clothes back from the receptionist. The one thing she's said she won't do is give them to you directly, so you are fucked, aren't you?"

Nicki looked at Amy's stern face and realized it would not be good to dispute this in public and Amy was right she had Nicki exactly where she wanted her. Nicki noticed the girl come back to the desk at the counter, glance up and grin broadly at them both. Why did everyone find this so funny, Nicki thought?

When they stepped outside, Nicki felt the coldness of the air around her ass and the tops of her legs. She felt exposed and nervous but also horny. They walked up the street, they passed several people. There were some who seemed not to notice and those who starred open mouthed at Nicki's long legs, short skirt and blatant make up. They turned the corner into a side street, which was rough and had lots of ripped and damaged buildings. Amy glanced up at Nicki

"Get in." she hissed.

Nicki had been so focused on the people and buildings that she hadn't noticed the Audi convertible they stood next to. She got in and tried to do it as decorously as possible. How crazy, she thought, I am dressed like a hooker and worried about how I look getting into a car!

"It's such a nice day, I think we'll have the roof down," said Amy

Oh god, Nicki realized that this would expose her to all the passing traffic. They sped off into the outskirts of Manchester. Amy seemed to take great delight in making sure that she always stopped on the right of any other car so that the driver could clearly see Nicki and some of what she was wearing. When they stopped next to a lorry, the driver looked down and could see Nicki's black latex skirt and the tops of her stockings. He honked his horn and waved at Nicki.

"Wave back Slut." Amy said as she noticed the driver. Nicki waved not very confidently, the wind blowing in her hair. The lights changed and Amy sped off. "Pity, I've got other plans for you, and I don't want to be late, but he could have used your sweet virgin ass couldn't he? "

"Yes Mistress." Nicki didn't know whether to be relieved that they had not stopped or even more concerned about what they were late for. They drove further out of Manchester, past disused factories, abandoned warehouses and general run down neighbourhoods. Amy looked over at her and said:

"How about I leave you here Nicki?" they had just come to an area of deserted road in middle of redevelopment site. There was a tram station up ahead about 500 yards, but other than that it was pretty desolate, they were about 4 miles out of Manchester.

Nicki just looked at Amy in speechless fright, if she left her here, how would she get back to hotel? She was dressed like a slut and she had no money phone, or anything.

"You would have to find some way of getting people to help you, wouldn't you?" Amy continued "maybe the men would give you a lift if you gave them a blow job?" Amy arched an eyebrow, laughing at Nicki.

Nicki didn't know what to say, she didn't want this at all, but what could she do?

Amy laughed out loud "Don't worry, not this time, I've got better plans and anyway we are late for your date" Saying this Amy raced down the road her eyes sparkling and her hair flying in the wind. Presently, they turned into a parking area by some flats.

"Out you get Slut!" Amy said as she pulled to a stop. Nicki stepped out gingerly and looked around. They were outside an impressive modern set of flats, part of the renewed landscape around Manchester. The parking area had secure gates and Nicki could see that the doors were key card access only. She followed her Mistress as she set off for one of the flats. Once inside, Amy told Nicki to sit down and offered her a glass of wine. She then busied herself in another room as Nicki waited anxiously. She could see through the windows into the flats opposite as people were going about their daily lives, little realizing what they would be able to view in a few minutes.

Amy came back into the room and slipped a blindfold round Nicki's eyes. She whispered into Nicki's ear "Now you are completely in my control, you are helpless aren't you Slut?"

"Yes Mistress." Nicki enjoyed being robbed of her sight but her fear levels increased as well. She thought she heard a noise from outside the flat.

"Stay there!" ordered Amy as she went out of the room to the front door. Nicki could hear voices, she couldn't tell how many, but it was definitely one male voice!

After a while, Amy came back in the room, wordlessly grabbed Nicki's hand and led her out of the room.

"I hope you will behave for me slut, this is a very special surprise and if you let me down I will be very cross." She whispered close to Nicki's ear as she led her through the flat. Nicki was aware of being lead into a room and heard the door being closed behind him. Suddenly her back was pushed against the door and she felt Amy grab her hands and heard the click of handcuffs as Amy secured them in front of her. Next her feet were pushed apart and into ties so that she was standing legs wide apart flat against the door.

Nicki heard some doors open across the room, she recalled there were French windows opposite the door, and the lights were on so everyone could see she was tied against the door.

"Here she is," she heard Amy say "do what you like to her, she is a real slut, she loves cock and she'll do anything. I'll be back in about 30 minutes, let me know then whether she will be of any use to you later."

Nicki was shocked, what was Amy thinking, she was tied up and helpless and who was this she was talking to? She felt someone move closer to her.

"Be good now or else!!" It was Amy. Nicki felt the brush of Amy's lips against her cheek and then she was gone. Nicki stiffened with fear, the room was silent, and then she heard someone moving across the room. Suddenly a hand grabbed her arse and felt her fake tits.

"Mmmmm, Amy was right you're a real slut aren't you love? You wanna suck Jimbo's cock? Jimbo loves having his cock sucked and you look ripe for it" the man smelled strongly of cigarettes and his hands were all over Nicki's body, squeezing her arse, mauling her chest. He stuck the dirty fingers of one hand in her mouth while the other hand played with Nicki's cock.

"Suck these slut mmm, what a slut you are. I love your skirt you filthy bitch" Jimbo pulled his fingers out of her mouth and pushed Nicki down on her knees. It was really uncomfortable as Nicki's feet were still tied to the door. Jimbo's cock was shoved towards Nicki's face. It was a big one and Nicki struggled to take it all in her mouth. It was a thick uncircumcised cock and this guy seemed to want to shove it all the way down Nicki's throat. Because her hands were tied, Nicki could not stop him shoving it hard in her mouth. It was clean though and despite her position, Nicki was enjoying sucking and licking this monster. Nicki slid down to her knees, her feet still attached to the door,

"Come on bitch suck it, suck my cock"

"She loves it doesn't she?" Nicki heard Amy's voice from out of nowhere, she hadn't left him! She'd tricked him into thinking she had, and she was watching his performance as were the people in the flats opposite no doubt. Suddenly Nicki felt her feet being untied. She was able to move her head up and down on Jimbo's cock as his hands pulled at her chest and skirt. He was thrusting hard into Nicki's mouth his breath coming hot and hard. He pulled out and shoved his hand in her mouth again. Nicki felt her blindfold being lifted and she was blinded by the brightness of the lights in the room. She saw Amy embrace Jimbo and kiss him deeply while playing with his cock in her hand.

"Mmm she gets really jealous watching me do this;" Amy murmured loud enough for Nicki to hear "are you going to fuck her mouth Jimbo?"

"Good idea, drag her over onto the bed."

Amy pushed Nicki over and onto the bed so that her head was hanging over the edge. Jimbo stood on the other side of the bed, which was right by the window. Nicki could dimly see figures standing across the courtyard watching what was going on. Jimbo was at just the right height to thrust his cock deep into Nicki's throat. He pulled it nearly all the way out, then thrust it nearly all the way in, back and forth. Nicki felt like she couldn't breathe. His cock seemed bigger and it was deep in her throat now. Nicki had never done this before and she felt like she was going to choke.

"Ahh that's good, you fucking cocksucker, that is really good!" Jimbo said "I'm gonna cum all over your face."

Nicki attempted to nod but that was difficult in the position she was in. Then she felt Jimbo's cock twitch as Jimbo's breathing increased. Suddenly it erupted, cum went everywhere; into Nicki's mouth, hair and even up her nose. Nicki tasted his cum; it was strong, tangy and thick, the smell filled her head as he pumped into her mouth. Jimbo shook his cock in Nicki's face, the last drops going in her eye now as well.

Amy laughed at the amount of cum on Nicki's face. Nicki was gasping for breath and her own erection subsided as Jimbo looked down on her.

"What a slut," she said through her laughter "and this is just the test, do you think she can cope later Jimbo?"

"Oh I think so," he said "I want my friends to use her and I want the virgin ass you promised me." He tucked his cock back into his shorts and walked towards the door.

"Well maybe," Amy said "not sure if this slut deserves that, but we'll see you later."

Nicki realized that the night had only just begun and the cum that was now dribbling down her face was only the start.

To be continued...

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4 Comments
AnonymousAnonymousalmost 3 years ago
Older Man

I in joy being a sissy cross dresser full time.I just found our should i say he just found me.We met at a book story and we sat and talked for some time.He said he would like to take me to bed and treat me like a lady.When we got to his place he was all over me.Feeling me up kissing me removing my dress and sucking my breast.Once we got to the bed he removed this pants and out pooped the biggest fates cock i have ever seen.He layed on top of me rubbing his monster cock all over my body.Soon he was forceing it in my mouth and started to fuck my face.Once hard he flipped me over cuffed my hands behind my back and he pushed his cock balls deep in my ass.He fucked me all night and started again the next day.

AnonymousAnonymousover 11 years ago

Loved the start of your story, continue adding chapters.

AnonymousAnonymousover 15 years ago
Nicki's learning rapidly:)~

Go on Nicki, I'm sure you'll learn even more valuable lessons with the next story.

AnonymousAnonymousover 15 years ago
So good.

More, please

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