Tony to Tanya Ch. 03

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Tony, Sarah and Sophie go out for the evening.
4.5k words
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Part 3 of the 3 part series

Updated 10/23/2022
Created 01/20/2010
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joshy029
joshy029
967 Followers

authour's note: i'm terribly sorry it took so long for me to write this. i know that at least a few of you are pretty peeved at me. to explain, i got writer's block and i just couldn't think of any way to end it. as a result, the ending isn't as good as the rest of it, in my opinion.

as i've mentioned before, this is the last chapter planned in this series, though i may come back if i have any ideas in the future.

i've currently started work on the start of another series, but i'm not revealing any details yet.

i hope you enjoy the story.

***

Sarah finished applying make-up to Tony's face. It was mostly subtle, just enough to highlight his eyes and cheeks. The only part that wasn't so subtle was the lipstick; bright red.

He was already dressed up in a beautiful black dress that left his back and shoulders exposed and only went down to mid-thigh. It was one of Sarah's, since they didn't want to spend too much money on a dress that was only planned on being used once. He was wearing realistic breast-forms, glued on to fill out the chest of the dress a little. They looked pretty good to him.

Underneath, he was wearing a pair of lacy, red, French-knickers to match the red lipstick his girlfriend had just applied to his lips.

Tony was worried again, though. Just a few hours ago, he'd been shopping with his girlfriend Sarah. They'd gone to buy some clothes for him. Girl's clothes. He'd gone out dressed up, but that was only for a short amount of time, most of which he spent in a dressing room of a shop. This time they were going out for several hours, all of it in full view of the world. Surely somebody would realise he was a guy, not a girl, even if he had the figure of a young woman.

He'd also met an old friend and fuck-buddy of Sarah's. She was called Sophie, a beautiful transsexual woman. Under the guise of giving "Tanya" help getting changed and to give her opinion on the new clothes, Sophie had sucked Tony's cock. Tony had returned the favour, sucking his first cock and carrying out one of his fantasies, being with a transsexual, in the process.

Now he was going out to dinner with his girlfriend and Sophie, who he supposed was his new friend. They were going to a nice Italian restaurant on the other side of town. Tony had been there before, for his eighteenth birthday. They did good food and he liked Italian food.

There was a knock at the door and Sarah went to answer it. When she came back into the room, she was accompanied by Sophie.

"Hello Tanya," Sophie said with a wink. "How you doing?"

"Fine thanks." Tony replied in his very best girl-voice. "What about you?"

Sophie made a motion indicating that she was fine while Sarah told them both that she was going to get ready. She'd spent all her time helping Tony that she hadn't had time to get changed or put any make-up on.

Tony and Sophie both nodded. Tony went and got the shoes he was wearing for the evening. They were black with 3-inch heels and the perfect size for him.

"Has Sarah told you the plan for this evening?" Sophie asked him as he put his shoes on.

Tony nodded. While he'd been in the shower, Sarah had been on the phone with Sophie, getting the details. After dinner, they were going to a nightclub for a few hours before heading back to Sophie's place for the night. Tony's parents weren't expecting him home and neither were Sarah's.

Tony and Sophie exchanged a bit of small-talk on the sofa while waiting for Sarah. They told each other a little about themselves and things they enjoyed doing. The main thing they had in common was Sarah: they both enjoyed doing her.

While they were chatting, Tony checked Sophie out. She was wearing a stunning red dress that barely reached below her ass and showed ample cleavage. Her shoes matched her dress, red with 4-inch heels.

Her dress was riding up, so that it was practically around her waist. She didn't even attempt to adjust it, she just left it like that. Tony observed that she was wearing a blue thong that only just covered the slight bulge of her soft cock and her balls.

Her hair was straightened to frame her pretty face, much like Tony's was, but much more elegant due to the fact that her hair was longer. It fell like a sheet down to her shoulder-blades with slightly curled tips.

At first-glance, it didn't look like she was wearing any make-up other than her deep-red lipstick. Upon closer inspection, she had subtly applied blusher, mascara and a very light amount of foundation that was hardly noticeable at all.

About ten minutes after she'd left, Sarah came back into the room and put her own shoes on while listening to their conversation. She was also stunningly beautiful in a dark-green dress and matching 4-inch heels. Her outfit was only slightly more conservative than Sophie's, reaching down to mid-thigh and showing less cleavage.

The three of them sat talking for half an hour before getting in Sophie's car and heading to the restaurant. They arrived ten minutes before their reservation, but the booth that Sophie had reserved for them was free to they were seated and talking while waiting for the waiter to arrive and take their orders.

When they'd ordered their food and drinks, they kept talking and joking to pass the time. Tony made sure to be careful with his voice, since he was out as Tanya, not himself.

After eating, Tony excused himself to use the bathroom. Walking into the Ladies' room instead of the men's took a lot of concentration, he didn't usually think about it. He met the girls back at the table before they left and got back into the car.

They pulled into a car park near the club and found an empty space. Tony didn't usually go to nightclubs, and even when he did, he wasn't dressed as a girl. Id they asked him for ID he was screwed, his alter-ego didn't have any.

Luckily, he didn't need it. Sophie knew one of the doormen and they go in without a fuss. Unlike the rock bars Tony had been to, this bar was a mixer, playing all kinds of music, from jazz to indie, to rap. It turned out to be quite a fun place. They had a few drinks, Sophie going for water or soft drinks since she was driving, and a few dances.

After a while, Tony needed to go to the bathroom again. Pushing through the people that were dancing, he didn't notice that somebody was following him. Still oblivious, he walked into the ladies' room and into a cubicle.

A minute later, as he was leaving the cubicle, he bumped into Sophie. She pushed him back in and he stumbled back, ending up sat on the lid of the toilet. Sophie walked into the cubicle, closing and locking the door. Tony would have had no escape, even if wanted to escape.

"Do you know how hard it is to resist your girlie-voice?" she asked, obviously flustered.

"No I don't." Tony said in the very voice she was talking about. He grinned. "How hard is it to resist?"

"Lets just say I wanted to throw you on the table at dinner and fuck you." She replied, even more flustered.

"I wouldn't have minded." He told her, putting a hint of invitation into his voice. "We're alone here, how about I let you relieve your tension?"

That brought a big grin to her face. She pulled the hem of her dress up and exposed her hard, thong-clad cock.

Tony knelt on the floor and looked up at her. She looked back, her eyes begging for him to suck her cock. He waited until her eyes told him she was experiencing unbearable sexual agony before licked her cock through her thong.

Sophie uttered a moan of relief and pleasure as he continued to lick, causing the material to slowly soak with saliva. As he licked, he moved a hand up and cupped her balls through her underwear, gently squeezing and manipulating them, occasionally going to lick them or suck them.

Tony stopped licking and pulled the material of her thong aside, allowing her rock-hard cock the freedom it would be begging for, if it could speak. He began to lick it again, savouring the taste of her bare cock. He allowed his tongue to flick over the head of her dick, tasting her salty pre-cum. He wanted more that that, however.

He licked down to her balls, licking and sucking them before licking back up her shaft and engulfing the head. Sophie sighed as he licked a circle around her engorged head, then slid more of her shaft into his mouth.

Tony brought his head back, allowing his tongue to slide along the underside of Sophie's cock, causing another sigh of relief. When he had only the head in his mouth, he bit down lightly before sliding back down, taking more of her in, this time.

He started bobbing his head back and forth, coating her shaft with his saliva, before releasing the beast from his mouth and standing up. Her disappointment was palpable. He'd stopped before she came and she wasn't happy.

He kissed her before she could voice her outrage. Her tongue brushed his lips and he parted them in an invitation, which she instantly accepted. Their tongues danced a waltz, exchanging saliva and her salty pre-cum.

Tony slid his hands up Sophie's waist, underneath her dress as she pulled his dress up and grabbed his ass. As she kneaded his ass cheeks, Tony stroked her waist and back, slowly going up until he had his hands on her large breasts.

He ran his thumbs over her nipples, before squeezing them between thumb and forefinger. Sophie moaned into his mouth and sucked on his tongue while she slid a hand under the thin piece of material in his ass crack and rubbing his tight, puckered anus.

Tony pulled her dress over her head, breaking the kiss for a second to do so, and dropped it on the lid of the toilet behind him before going back to work on her nipples. He alternated between squeezing, twisting and rubbing them.

Tony broke the passionate kiss and stopped playing with Sophie's nipples. Once again, he knelt down, this time hooking his thumbs into the waistband of her thong and pulling it down to her ankles. She lifted each foot off the floor in turn so that he could fully remove her underwear and place it on top of her dress.

All the while, he was watching what she was doing. He was as hard as she was, and it showed. The tip of his cock was peeking out of his own thongs waistband. He removed it and let his cock spring free, putting his underwear with hers, then he removed his dress and did the same. They were both naked now, apart from their high-heels.

When Tony had finished removing his clothes, Sophie spat on her fingers.

"Turn around, bend over and spread your cheeks." she told him.

He did as he was told, bent over slightly with his hands spreading his cheeks so his anus was clearly visible.

Sophie slipped he fingers between is splayed ass cheeks and rubbed her saliva into his anus. When his hole and her fingers were sufficiently wet, she slipped her middle finger in up to the first knuckle. His sphincter clamped down on it tightly and she slowly pushed into him until she had her whole finger in.

Tony moaned in pleasure, despite the pain that accompanied it. He'd been dying to have Sophie in his ass, and now she was working to have the same thing.

She slowly started to pump her finger in and out of his ass, allowing time for him to relax. When he had and his ass was a little looser, she started pumping faster, making Tony moan a little louder.

After a while she slid a second finger in and a few moments later, a third. She continued to pump her fingers into him, hardly breaking the pace she'd set when she slid the next finger in. He moaned louder and louder with each added finger.

When Sophie was satisfied that he could handle her cock, she pulled her fingers out of his ass and slid her shaft between his cheeks. As she rubbed her cock between his cheeks, Tony could feel the pulse of the blood flowing through it. The slight vibration of it felt wonderful.

She offered the fingers that she'd had in his ass to him and he clamped his mouth around them. He sucked and licked them as if his life depended on it.

After a short while, Sophie removed her fingers from Tony's mouth and used a hand to spread his cheeks while she lined her cock up with his anus. When she was ready, she gently pushed forward, easing herself into his tight, warm ass.

Within a minute, she was balls-deep inside him and he was moaning in pure pleasure. It occurred to her that somebody could come in at any second and hear them fucking, but she didn't care. In fact, she welcomed them, maybe when they saw that she had a cock they'd want her, too.

Slowly, she pulled out until only the head of her cock was inside Tony. She stayed there for a few seconds, then she slammed back in as deep as she could get, making him cry out loudly. She set a slow, steady pace and, after a while, Tony pushed back to meet her strokes, causing them both a lot more pleasure, their moans mixed; the sounds of shared bliss.

As she ravaged his ass, Sophie reached around and grabbed Tony's cock and started to stroke it, matching the strokes of her hand with the strokes of her cock.

Tony wasn't making any noises of pleasure any more; he was trapped so deeply in the throes of his pleasure at being penetrated, that his voice was failing him. On top of that, his knees were buckling. Soon he'd be on the floor.

As if she was reading his mind, Sophie gently lowered him to the ground, not removing her cock from his ass. Once they were both knelt, she resumed her thrusts with vigour, increasing the speed and strength of them.

Before long, Tony felt a tightening in his balls. He was about to cum, but he couldn't tell Sophie because he couldn't even articulate screams of pleasure.

Suddenly, Sophie plunged balls-deep into him and held herself there. Her cock bucked several times, shooting jet after jet of hot cum into Tony's anal cavity. He could feel it splashing against the walls of his ass and trying to escape. At this point he was unable to stop himself cumming and he shot several jets onto the floor of the cubicle.

Sophie held herself in his ass as she slowly softened inside him. He saw her reaching for her tiny handbag. When it was out of his sight, he heard her take something out, but he was too drained to turn to look.

Finally, she slid her cock out of him. Before any of her cum could escape, she slid a butt plug into his still-gaping hole.

Ten minutes later, they were searching the club for Sarah. When they'd both recovered, they had cleaned the cubicle, gotten dressed and touched up their make-up before leaving the bathroom.

They found Sarah waiting impatiently at the bar, where they'd left her. They walked over to her and she hugged and kissed them both before turning to Sophie.

"I told you that you could fuck him and come right back, not fall asleep afterwards." she said indignantly.

"Sorry. We got a little carried away." Sophie replied. "Shall we get going?"

Sarah nodded and the three of them left the club and got back into the car. Tony found this a little uncomfortable, since when he moved, the butt plug moved. It did help him walk a little more femininely, though. He'd practised that, but it was always forced. With the butt plug it was more subconscious so that he was comfortable.

"So, did you have fun in the bathroom, you two?" Sarah asked.

"Yeah," Sophie said. "It was a lot of fun. You should have heard Tanya scream."

They both laugh and Tony felt himself blush a little. The rest of the long trip was almost silent and it was a relief when Sophie pulled her car into her driveway.

Tony thought that the house Sophie lived in was that it was too large for one person. And he marvelled at the size when she gave him a tour while Sarah went to grab some drinks for them. It was a four-bedroom house, meaning there was a lot of unused space. The last room to look at was the attic, which was Sophie's bedroom. It was spacious and had two windows; a skylight and one on the side of the house, during the day the room would be very well-lit with natural light.

In the middle of the room was the largest bed Tony had ever seen. It would easily be able to hold six people quite comfortably, and it looked extremely soft. The rest of the room was quite messy, papers, books and clothes strewn around, as if somebody had been looking vigorously for something and not tidies up afterwards. The only tidy things in the room were the TV stand, computer desk and bed.

"Sorry about the mess," Sophie said. "I don't usually have a reason to clean up. The clothes on the floor are clean, I just don't have the time to put them away. Well, that, and I don't have the room for them anywhere."

To show what she meant, she walked over to the wardrobe in the corner and opened it, then opened the drawers next to it so that Tony could look in them.

Inside were a lot of clothes and items she obviously used when she masturbated or when she had somebody to fuck. Dildos, butt plugs, strap-ons, vibrators and just about any sex-toy that Tony could imagine was in the drawers. The wardrobe held mini-skirts, tops, catsuits, and sexy outfits of every kind made of just about every material. He found himself a little light-headed and he felt his jaw literally drop.

When he heard the door open, Tony turned and watched as Sarah climbed the stairs carrying bottles of beer, vodka and coke in a box.

"From the look on your face, I take it she's showed you her collection of toys and clothes?" she asked with a slight smile.

Tony could only nod in response.

"Aww, looks like she's speechless." Sophie teased, still calling him by his portrayed gender.

She closed the wardrobe and drawers and gently pulled a still-speechless Tony over to the bed and pushed him into a sitting position.

When he finally snapped out of it, Tony found himself cradling a beer he only just remembered being passed to him. He took a sip and collected himself. He noticed that Sophie also had a beer, while Sarah had a vodka and coke.

They talked and joked for an hour while the alcohol lasted then had to decide on what they were going to do next; sleep or something else. It was Sarah who came up with the most fun idea.

"Well I say we have a threesome." Sarah suggested.

"I agree." Sophie piped in. "Tony?"

"Yeah." he said, enthusiastically.

Sarah jumped at them both, knocking them flat on their backs, and hugging and kissing them both, laughing. Tony had a feeling Sarah had wanted a threesome with him and Sophie for a while, now.

She finally stopped and let them sit up. Sophie stood, walked over to the wardrobe and opened it, once again revealing her kinky clothes collection.

She started rummaging inside, and when she turned around again, she had three outfits: a skin-tight latex bodysuit that looked like a one-piece swimsuit with a hole in the crotch that was obviously for her manhood, and two French-maid outfits. She tossed one of the maid outfits to Tony and the other to Sarah.

"You'll have to take the breast-forms off for that, Tanya." she said. "It's a bit tight in the chest."

Tony nodded and went to the bathroom to change and take the breast-forms off. First, he took his dress and shoes off, then concentrated on the breast-forms. The glue holding them on was water-soluble, so he daubed water around them until they were able to be easily removed.

Next he got dressed in the outfit Sophie had given him. It was too tight in the chest for him to have worn with the breast-forms on, as she'd said. The outfit was a standard French-maid outfit: white blouse, black dress, white stockings, a matching garter-belt and a bonnet. He thought he looked quite sexy in it.

He picked up the dress, shoes and breast-firms he'd discarded and carried them back into Sophie's attic-bedroom. He discarded them once again, where Sophie indicated and she handed him a pair of shoes to put on. They were simple shoes, black with flat heels.

Sarah was wearing the exact same outfit as he was and looked very sexy in it. Sophie, however, was wearing what Tony suddenly thought of as her dominatrix outfit, her cock and balls hanging through the hole in the crotch.

joshy029
joshy029
967 Followers
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