Tony to Tanya Ch. 02

Author's Note:

Thanks to everyone who read, voted and commented on the first installment of the "Tony to Tanya" series. I'm really appreciative of you all. It is, after all, always good to get such positive comments as a new writer.

I'd also like to say that i have another installment after this one. It's only the most basic of ideas right now, but it will come to me. I'll start on it, or at least outline it, when it comes to me. i do, after all, have other projects to do on other sites that i've been meaning to do for a while now.

Thanks again to everyone that have read and enjoyed this series so far.

Enjoy.

***

Tony woke up on Saturday morning feeling excited without knowing exactly why. He tried to sit up, but his left arm was pinned down by Sarah's body. This was normal for a Saturday morning, since she tended to sleep at Tony's house on Fridays.

The reason he was excited suddenly hit him. On Tuesday, Sarah had told him they were going shopping today. This had been right after a great fucking-session in which Tony had been dressed in Sarah's old school uniform and she'd fucked him with a strap-on dildo. It had been a very kinky evening.

Very carefully and gently, Tony extracted his arm from underneath his girlfriend and made his way to the door. He went down the hall for a shower, wondering what shops they'd be visiting and what they'd be buying for him. He knew it'd be girl's clothes, but he had no idea what-so-ever what kind.

While he was pelted with water from the shower, images came to his mind. Thongs, skirts, stockings, dresses, blouses, and every other kind of girly clothing-article he knew of. In his mind's eye, he was wearing them and examining himself in a mirror. Tony's hand drifted towards his crotch as he thought of these things, and he began to stroke it absently.

Thankfully, Tony wouldn't have to be sized-up for these clothes. He wasn't much taller than Sarah, and the extra height was just leg. He'd be dressed up when they went out, and he'd be using his best girly voice, which he'd been practicing in his spare time.

When he was trying anything on, Sarah would go into the changing room with him, under the pretext of helping one of her girlfriends find clothes that suited "her". Nobody would know it was actually her boyfriend. Tony just hoped he wouldn't see any of is friends in the town centre; that would be uncomfortable.

The sound of the bathroom door opening snapped him out of his thoughts, and he realised that he was actually stroking his cock. He quickly stopped.

"I'm in here," he called, thinking it must be one of his parents or his older sister. "I must have forgotten to lock the door."

"Don't worry," Sarah's responded. "It's just me. Nobody else is home."

"Right," Tony said, feeling like an idiot. His parents would be at work and his sister would be out with the friends she hadn't seen since her last holiday from college. "I forgot that nobody would be in at this time."

Sarah walked into the bathroom and looked around the shower curtain. Her eyes wandered Tony's body and she noticed his erection.

"Excited about today, eh?" she asked with a sly grin.

Tony blushed slightly. He was comfortable with being naked in front of Sarah, and he was comfortable with what had transpired on Tuesday. But for some reason, admitting being excited about the day's planned shopping was slightly embarrassing. Instead of saying anything he just nodded.

"Well, we can't have you walking around with a raging hard-on, now can we?" Sarah asked, sounding amused. "Unless you want people to know you're cross-dressing?"

Tony shook his head vehemently. He didn't want people to know that. He wanted his life to be without people automatically thinking he was gay, which he was certain most of his friends would do if they were to find out.

"Then you'd best make sure that goes down before we go out." She told him. "Wash yourself with this hair-and-body wash and use some conditioner, your hair's long enough for you to not need a wig." She added.

She left to have breakfast, leaving Tony to wash himself as she told him to. He had to be able to pass as a girl in scent as well as looks, after all.

When he'd finished showering, Tony went downstairs wrapped in a towel and made himself a bowl of cereal. He went to eat it in front of the TV where Sarah was eating her own breakfast and watching a sitcom.

While he was eating, Tony kept giving Sarah side-long glances. She didn't seem to notice, or if she did, she didn't show it.

He was starting to get nervous about today's plans. He'd be out, dressed as a girl, and with England's weather, the skirt he'd be wearing would probably be caught in anything from a strong breeze to a strong wind. That would probably expose him to everybody in the vicinity.

Tony still couldn't quite believe what he'd gotten himself into. He'd always known his girlfriend was kinky, but he'd never in a million years imagined she'd get him to dress as a girl, fuck his ass, then take him shopping for some girly clothes of his own at the weekend. He enjoyed it, but he was still apprehensive about the entire thing.

"We'd better get ready." Sarah told him, breaking his chain of thought.

"Sure," he said. "You are going to help me, right?"

"Of course I am." She told him. "You'll have to practice the hair and make-up part yourself, but I'm sure you can dress yourself." She added teasingly.

Tony took their plates into the kitchen then they both climbed the stairs and went back onto his room.

Sarah went through a drawer where she left some of her clothes for whenever she slept over. It saved her having to bring a change of clothes with her.

'Two changes in this case.' Tony thought to himself.

She brought out two pairs of panties; a thong and a full-seat pair, two skirts and a couple of plain tops for them both to wear. She handed him the panties, keeping the thong for herself, and then a skirt and top before going back into the drawer to get herself a bra.

They got dressed quickly and Tony waited while Sarah did her make-up. When she'd finished, she motioned him to sit in the chair she'd just vacated and she did his. Nothing extravagant, but enough to ensure nobody recognised him as a boy. Then she did their hair; straightening it and ensuring that it made them both look sexy, and in Tony's case, like a girl.

Sarah handed Tony a pair of stockings and pulled a pair on, herself. When he had them on, she picked a pair of shoes for him and then they went downstairs. She put on the shoes she'd brought with her the night before and grabbed her handbag. They were ready to go out and Tony was extremely nervous to say the least.

An hour later, "Tanya" and Sarah were walking down the high street in the city centre. Sarah had noticed that Tanya looked worried and only one thought passed through her mind when she had first noticed it: cute.

Many people turned their heads to get a second look at the two of them. This was what Tanya was worried about; that somebody might notice she wasn't actually a girl. Luckily, she hadn't seen any friends from college. If she had, she'd have probably passed out from fear of discovery.

They reached a clothes shop exclusively for girls and went inside. It was beautifully set-out. Unlike the unisex or men's shops in the city centre, everything was in a specific location. Underwear was hung along one wall on hooks and on a few small stands just in front of the wall. There was a wall exclusively for shoes and then there were skirts, dresses, blouses, stockings and tights, trousers and even hats in their own little, neat sections.

"Welcome, ladies!" the woman behind the counter said, enthusiastically. "How may we help you today?"

"Oh, we're just looking for some clothes for my friend, here." Sarah said, without even a hint in her voice to insinuate that Tanya was actually Tony.

"Alright, what sort of thing are you looking for?" the shop assistant asked.

"Some sexy clothes." Sarah told her. "Something that suits Tanya, here."

"I think we have something she'd look very sexy in." the shop assistant said, winking at Tanya.

She motioned them forward and they walked towards the changing rooms. They stopped half-way down the shop and the woman grabbed a few items. They went further and she grabbed a few pairs of stockings.

"I'm grabbing you things that go well, together. I hope you don't mind me picking a few items to try." She said.

"Not at all. Any help you can give me is welcome." Tanya replied.

"My name's Sophie." The assistant said.

"Nice to meet you, Sophie." Tanya said.

As they'd been walking, Sophie had grabbed more things for Tanya to try. They reached the back of the shop and stopped.

"You can wait here, if you like, Sarah. You don't need to keep an eye on me. I remember our deal." Sophie said with a wink at Sarah.

She pushed Tanya into one of the booths and pushed her down.

"You're very sexy, Tanya." She said. "Or should I call you Tony?"

"You know?" Tony said, reverting back to his own, male voice. "How?"

Sophie chuckled. "Sarah and I are friends. She comes in here to shop every so often and we built up a friendship. She came in on Wednesday and told me of your hot fuck-session. I wish I was there to watch, and maybe join in."

A large grin was on Sophie's face by this point and Tony was seething silent anger towards his girlfriend. She'd told him this was to be a secret and then she'd gone and told this woman all about it.

"Before you two were dating, Sarah and I were actually fuck-buddies." Sophie continued with her monologue, ignoring Tony's obvious anger. "She's told me quite a bit about you when we've had lunch together and we both think you'll like me."

At that point, Sarah popped her head around the door and Tony's head snapped around so he could glare daggers at her.

"Sorry, Tony. I had to tell her. She's not you're average girl." She said apologetically. "Anyway, she falls under the category of one of your fantasies."

Tony was baffled, he had plenty of fantasies. Every guy did. He was running through them all when Sarah spoke again.

"About the agreement, Sophie." She said, and Sophie's head snapped around. Sarah smiled. "Anything goes. I was a bit reluctant, but go for your life."

"Thank you, Sweetie." Sophie said and Sarah left, closing the door behind her. Sophie quickly locked it.

Tony was still going through all his fantasies. Or rather the fantasies that were relevant to the situation he was in. Lesbian seemed to be the obvious fantasy. But then, there wasn't another girl in the room...unless his alter-ego, Tanya was involved. Tony's mind was racing when Sophie answered which fantasy it was.

Sophie unzipped her skirt and pulled hit down, revealing lovely pink lace panties. She had brilliant legs and Tony could also see she had a magnificent, round ass. There was something out of place, however, but before his brain registered it, Sophie was pulling her panties down, as well.

When she stood up straight again, Tony could see a rather large cock between her legs. Sophie was a Transsexual. Tony had had fantasies of fucking a shemale for years. He thanked Sarah in his head with extremely humble apologies for being angry at her. He cock was responding to the amazing woman before him.

"By the way, I figured I ought to tell you why Sarah has that strap-on." Sophie said. "It was so she could return the favour to me. We usually only ever did anal, and she liked to fuck my ass every once in a while."

Tony's cock was fully hard by the time she'd finished and he was dying to get a piece of her. He felt very restricted in the panties Sarah had given him earlier that day.

Sophie smiled as if reading his mind before kneeling down and sliding her hands up his thighs slowly and seductively. Her hands reached the waistband of Sarah's panties and her fingers hooked under them. She pulled them down, stopping only so Tony could raise himself of the changing booth's bench so she could take them off.

Once Sophie had pulled the Panties over the shoes Tony was wearing, she bunched them up and put them next to him. Tony noticed that the beautiful Transsexual woman was looking at his cock and licking her lips.

She stared at Tony's cock while she gently pushed his legs open. When they were open a decent amount, she leaned forward and licked up his shaft, causing Tony to grunt with pleasure.

"I want you to use your girly voice, not your every-day voice," she told him with a smile, before diving back to licking his hard shaft. Tony released a small, girly moan of pleasure this time, as Sophie wanted.

When she got to the head of his cock, she swirled her tongue around it like a pro. Tony had to stop himself from screaming his assent.

Sophie noticed this and picked up the discarded panties. She balled them up and pushed them into Tony's mouth so he wouldn't have to hold his moans back as much.

When that was done, Sophie slid his entire cock into her mouth. Tony's pleasure was so much that he almost screamed into the panties in his mouth. He was having his cock sucked by a shemale, he was in heaven.

Sophie started sliding her mouth up and down Tony's cock, swirling her tongue around the head when she reached it. He could hardly hold back from cumming, and even with his best efforts, he'd cum soon, anyway.

As the thought hit him, he felt the familiar sensation in his balls that told him ejaculation was on its way. He couldn't say anything, because of the panties in his mouth, and he was feeling too good to take them out.

Suddenly, Sophie stopped sucking him and looked him in the eye. She gently pulled him down off the bench and onto the floor where she straddled his head and got back to what she'd stopped. It was only then that Tony realised she'd been stroking her own cock.

Without hesitation, he removed the panties from his mouth, raised his head and started sucking her cock, like she was his. They were now both sucking each other and moaning into each other's cocks.

Suddenly Tony came. Moaning into Sophie's cock as he filled her mouth with his cum. She was milking every last drop from him as she continued to suck. Before he'd finished cumming, her own orgasm started.

Warm cum shot into his mouth and he struggled to swallow it before the next spurt came. He swallowed furiously, as he might do with a glass of water in summer after being outside for several hours.

Eventually, their orgasms both stopped, and Sophie stood up, shakily.

"That was amazing." She said. "We'll have to do more another time."

She pulled her panties and skirt back on, and when she was fully dressed she'd regained her composure. She no longer looked as if she was about to collapse. Tony follower her example and took the panties he'd been wearing off the floor and pulled them back on. They were damp with his saliva.

"Shall we go and get those clothes paid for, 'Tanya?'" she asked with a grin and a wink.

Tony just nodded, and then followed her out of the changing room where they met Sarah.

"Have fun?" she asked with a wide smile on her face.

"Yes, thanks." Tony said in his best girl-voice.

"I finish work at six if our plans or still on tonight, Sarah." Sophie said.

"Sure, Sophie." Sarah responded. She then turned to Tony and said, "You don't mind having dinner with me and Sophie do you, Tanya? We'll do something fun afterwards, too."

"Of course I don't mind." Tony said, still using his girl-voice. "I'm sure it'll be a lot of fun."

Tony had no idea what Sarah had planned, or Sophie, for that matter. He was sure it'd be fun, though, and he already had his suspicions as to what the plans were.

To be continued...