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They talked about what she’d done since she’d arrived—seen a musical, had a nice dinner—and how she was faring with the jetlag. She started to get up to refresh her mug of tea and he sprang up at the chance to do it for her, his first opportunity to serve. She liked a builder’s brew, sweet with a lot of milk, and she laughed when he said he wouldn’t hold that against her. She was as easy to talk to in person as she had been to chat with for weeks now, and Ben was giddy with his own good fortune.

There was a comfortable lull in their conversation, and he gazed at her as she held her mug in both hands in front of her. He knew that no one in that lounge with them would guess or imagine her sexual desires, not in a million years. Her appearance, lovely but utterly ordinary, belied what burned intensely inside of her.

She sipped her tea and her fingers played with the key hanging from her neck. “Are you curious about the box on the table?”

“I’ve been so busy looking at you that I hadn’t noticed it,” he lied in an attempt to flirt with her.

He’d both noticed the box and hadn’t stopped thinking about it since he’d noticed it. She’d told him that she would have a surprise for him when they met the first time. The box had to be it…didn’t it?

“Take the box and place it in your lap, but don’t open it.”

Ben did as he was told. It was the kind of box that baked goods might come in, but it seemed unlikely that it contained biscuits or cake. It was a little heavy and he felt something move around in it when he lifted it from the table.

“Go to the bar and ask for the key to the toilet. Once you’re inside, send me a message to tell me that you’re ready.”

Curious and nervous, he obtained the toilet key from the bar attendant. It was a single-occupancy toilet and he was grateful that there was no other cubicle for someone to occupy. He set the box on the edge of the sink and sent her a message: *I’m ready*.

*Open the box and follow the instructions*, came her reply.

He opened the box and on top was a card with handwritten instructions.

*Read all of these instructions before doing anything with the contents of the box.*

*You may choose which size plug you’d like to use.*

*Send me a photo of Daddy’s pretty pussy when you’ve made your choice.*

*Put the panties on before you come out of the toilet.*

*Make me another cup of tea.*

His phone pinged with a message from her: *You have five minutes*.

His heart was pounding. The contents of the box were obscured by tissue paper, which he lifted to reveal a pair of lacy black panties, a small bottle of lubricant, and a set of three hot pink silicone butt plugs. The flange of each plug was heart-shaped and set in the heart was a clear plastic rhinestone. The smallest one looked about one inch wide and the largest one looked about two inches wide.

Ben had a decision to make. He wanted to impress her but wasn’t sure that he could get the largest plug into himself in the time he had left (less than three minutes!). He unbuttoned and lowered his trousers and squirted some of the lubricant onto the medium-sized plug that looked to be about an inch-and-a-half across. After coating the plug, he squirted a gob of lubricant onto his fingers and rubbed the lubricant onto his asshole, working his fingers a bit into his hole. Once he felt his asshole was thoroughly lubed up, he pressed the tip of the plug against his asshole and bared down, relaxing and opening himself to accept the plug.

His phone pinged: *Two minutes*.

He moaned as he slid the plug into himself, his asshole quickly closing around the stem of the plug. He washed and dried his hands and then grabbed his phone to snap a picture of the heart-shaped jewel that protruded from him. He bent over and stretched his arm behind him and snapped the picture. He was quite pleased with the look of it! He quickly sent it to her and removed his shoes and trousers so he could pull on the panties.

Ping! *One minute*.

When he was pulling on the panties he noticed that there was precum leaking from his caged dick. The butt plug was having its intended effect on him, as were the panties. All of it was doing exactly what she knew it would do to him. Fully dressed, he put everything back into the box, washed and dried his hands again, and walked out of the toilet. He returned the key to the bar attendant before going over to the sideboard to make her another mug of tea. He tried to be inconspicuous when he knelt on one knee before her and extended the mug to her. As she took it from him, her hand grazed his, sending a shiver of pleasure through him.

He took his place again in the chair across from her and placed the small box back on the table.

“How do you feel?” she asked.

“Honestly? I feel fucking amazing. Utterly amazing.” He closed his eyes and inhaled deeply, smiling. He couldn’t help himself: he wiggled in the chair, just enough to make the plug in his asshole move a bit. The pleasure of that feeling made his dick leak more; he could feel the wetness against his skin in his trousers.

She curled her finger to him, a “come here” gesture. He went over to her chair and knelt beside her, resting his arm on the arm of the chair. She lowered her head so that her lips were at his ear; he could feel her warm breath and her lips tickled his earlobe. “Does Daddy’s sissy feel like a proper whore with Daddy’s clit locked and Daddy’s pussy stuffed in public?”

Ben almost fell over. He felt his face flush and his whole body grew warm. With those words, he was hers.

“Shall we go up to my room?”

Ben didn’t need to be asked twice. She stood and extended her hand to him and he took it, grabbing his rucksack with his free hand and sliding one of the straps over his shoulder. They made their way out of the lounge and into the hotel to the lifts, she a few steps in front of him leading the way. In the elevator she pressed the button for the sixth floor, and then she stood next to him with her hand at the small of his back. He felt her slip her hand down the back of his trousers and into his panties until they met the jeweled plug, and he felt her press the plug into him. His knees buckled and he whimpered with pleasure.

When the lift doors opened, she led him by the hand to the room at the end of the hall. When the door clicked shut behind him, she turned to him and in an pleasantly authoritative voice said, “Strip down to your panties.”

She sat on the edge of the bed and watched him remove his clothing, which he folded neatly and set on a shelf in the closet by the door. He placed his rucksack on the floor nearby. It was cool in the room, thanks to the air conditioning, and he shivered a bit.

“Are you cold, Tessa? Come to Daddy, I’ll warm you up.”

Hearing her call him Tessa sent a shiver up his spine and made him flush. This was the moment he’d been waiting for for the last three weeks: the moment that he could be Tessa with her in person, and she would be his Daddy. *I kinda want you to call me Daddy while I fuck you, is that strange?* she’d asked. It wasn’t strange; it was his dream! Even though he was attracted to both men and women, it was dominant women like her who held his heart. And the fact that she wanted him as a sissy, as Tessa, made him feel like the luckiest man on earth.

He didn’t feel quite so cold anymore, but obediently he went and stood in front of her, his hands behind his back and his head bowed. She was still fully dressed, wearing a dark pair of jeans and a black button-down top, and she stood up and wrapped her arms around him. They were almost the same height, so they were face-to-face and she kissed him, her tongue gently opening his lips to taste him. Her hands ran down his back to his ass and she cupped his cheeks in her palms. He wrapped his arms around her, enjoying the closeness of her even as he longed to feel her skin against his.

“So you liked the surprise you got down in the lounge?” asked, still holding him.

“Yes Daddy, it makes your sissy’s pussy feel so good and look so pretty!”

“Yes, it does,” she murmured, kissing his neck. “When I saw that jewel in Daddy’s pussy, it made my own pussy very wet.”

“Can I taste your pussy, Daddy? Pretty please?” Tessa gave her his best puppy-dog eye pleading look while her fingers played with the key around her neck.

She laughed and stroked his cheek. “Not yet, slut. You’re not quite ready. Daddy has another surprise for you.”

Only then did Tessa notice the pink gift bag on the bed, with pink tissue paper poking out of the top of it. Her Daddy sat on the bed and patted the spot next to her. Tessa sat down, his knees pressed together and his hands clasped, waiting obediently and expectantly.

She set the bag on Tessa’s lap. “It’s all yours.”

Tessa lifted the tissue paper out of the bag and then squealed with delight as she lifted the green ruched satin bodycon dress out of the bag and held it up. She loved the cut-out in the middle that would show off her toned stomach and the figure she worked so hard for. She sincerely hoped that Daddy would let her try it on tonight. “Thank you, Daddy!” she said, kissing her cheek.

“There’s more,” she said.

Amazed, Tessa looked down into the bag and drew out a black lace bralette that matched the black lace panties that she was wearing. Bouncing with excitement on the edge of the bed, she pulled out the small rose-printed cosmetic bag that was also part of her surprise. She unzipped it to discover it complete with mascara, eyeliner, eyeshadow, blusher…and lipstick! Bright red lipstick, perfect for the sissy slut that she wanted to be for Daddy.

“Thank you! Thank you!” Tessa threw her arms around her Daddy and covered her face with kisses.

Her Daddy laughed and kissed her lips sweetly. “Go put your new things on and make yourself the prettiest little sissy for me. I’ve given you a lot, now it’s your turn to thank Daddy properly.”

Barely able to contain herself, Tessa gathered up everything and went into the bathroom. Where to start? She remembered that her heels were in her rucksack, so she grabbed it quickly (smiling and waving briefly at her Daddy), before enclosing herself in the bathroom again. First, she put on the bralette and decided that her silhouette would be much improved with the breast forms that were in the rucksack. She fished them out and slipped them into the cups of the bralette and was amazed at her transformation. Her medium-length hair had been up in a ponytail but she pulled off the elastic and gave her hair a shake as it fell into place. Even without any makeup on, she decided she was quite a good-looking woman. She ran her hands through her hair and then enjoyed her reflection in the mirror as she posed provocatively, enjoying the look of her tits in the black lace. She turned and looked over her shoulder so she could see her ass in the black panties. Delicious! She knew that her Daddy loved her ass.

Tessa took her heels from the rucksack and slipped into them before sliding the green satin dress over her head, letting it fall over her tits and hips. She could barely believe what she saw in the mirror: she was womanly. Willing to show Daddy, she applied the makeup in a fairly conservative and classy style, but she loved the touch of the bright red lipstick and how slutty it made her look. How slutty it made her feel. She pursed and puckered her lips and made sure her lipstick was perfectly applied to accentuate the mouth that would soon be worshipping every part of her Daddy.

It had been a couple of years since Tessa had been a sissy with anyone in person. More than she felt nervous, she felt a bit shy. How ridiculous, she wondered—Daddy had seen every bit of her already. About a week before Daddy arrived in London, she and Tessa had done a video call and Daddy had made her fuck her sissy pussy with a dildo while she watched and also made Tessa stroke her little sissy clit until it spurted cum everywhere. Then Daddy had told her to eat all of her cum, the way that she would have to when they were together in London. Remembering the call made Tessa’s cage feel tight.

*Now or never*, wondered Tessa as she turned off the bathroom light and stepped out into the room. Only the lights at the head of the bed were on, and the semi-darkness made her relax a bit. She could hear a bit of music playing as well. As she made her way back to where Daddy was sitting on the bed, still fully clothed, Daddy turned to look at her and let out a low whistle.

NSFW: yes

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