The One Night Stand (Ch. 01)

Story Info
Riley wakes up and recalls last nights date.
1.4k words
4.22
18.4k
23

Part 1 of the 4 part series

Updated 02/10/2024
Created 10/02/2023
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Riley wakes up in the morning, his ass still sore from last night. He smiles as he gently rubs it, he couldn't see it but he knew it was as red as the devil's dick. He wiped away the cum that had overflowed overnight and sat up a little. Lifting the sheets, he took a few seconds to look at his slender feminine legs covered in last nights cum that had hardened. He looked to his side to see the bed was empty, rubbing his hand over it, it was still warm.

"Guess she left recently".

He giggled to himself and picked up his phone to go through all the pictures he took last night with her. As he went through them, he sort of missed her. He was used to one-night stands where he was just grabbed and brought up to his room, or someone else's room, or just the pulled down under a park bench, but this was different. They had a nice meal, they watched a movie together and the whole time she wouldn't let him touch her massive bulging cock, even when he was watering at the mouth. It was all worth it though. He laid back into bed as he looked around the room, his panties thrown to the ground, his clothes torn into pieces as they were ripped off. He blushed a little as he slumped back into bed and thought back to last night's events.

He had gotten home from work and quickly showered. He was ready for a date and it was the first time he was actually invited to a restaurant. He got out and slipped on his favorite pink panties. He looked at himself in the mirror, if it wasn't for his tiny little dick, he could easily pass for a girl. He went through his closet and pulled out the new dress he had gotten just a week prior, a black gown that showed of his leg. He quickly did his make up and hair and was out the door in high heels. Soon he was at the restaurant and he looked in to see her.

"She looks even more beautiful than her profile" he whispered to himself. He walked in carefully balancing on the new heels, he waved at her as he approached her. She wore a deep blue dress, some jewelry and was carrying a large purse. She was obviously taller than her but he had gotten used to all the futa being much taller than him. She exuded a level of sophistication and power that he had never felt, making him get flustered. He stood next to the table and stuck out his hand.

"Hello there! I'm Riley! Its so nice to finally meet you" He smiled

"Oh! Hello Riley, its nice to meet in real life. Although I was expecting a boy" She giggled

"Oh, ummm, haha, I- I- " He stammered

"Calm down and sit!" She giggled as she pointed to the seat. As he sat she leaned forward and whispered "I know exactly who you are"

Riley blushed bright red. He had never had someone play with him like this before. His tiny little cock got hard from the playful bullying and he could see her dress changing shape as well. He smiled as the waiter came over and took their order and as soon as he left, Riley dropped his fork under the clothed table. He looked at her and with a wink said "Oops! Let me get that". He quickly got under the table and was immediately hit with the invisible cloud of musk. He could feel his mind getting numb as he looked up from the floor to his date, only to see her legs spread, and her panties moved to the side by her hand as her massive cock hung out. At nearly one foot long, this was probably one of the largest he had ever seen.

"See something you like?" She giggled as she slumped back a little, still holding her panties to the side, teasing him, to make him stare at her massive cock. He grinned as he reached out to grab her cock, but his hand was immediately slapped away. "Not yet honey! You'll have to earn it" She teased as she stuck her foot out, right under his chin. "Go on then, prove you're worthy" She giggled. Riley quickly slipped of her shoe and kissed her feet through the stockings. He kept his eyes on her cock as she slowly brought up her other foot, forcing it into his mouth. "Well if anything you could be good pet" She giggled, making her cock bonce a little. "You can just rip them off, I want to feel your tongue on my soles" She purred as Riley quickly complied and soon both her big toes were in his mouth. He licked them and played with them with his tongue, his eyes still glued to her cock. She lifted her feet as he stuck out his tongue and began licking her soles. He reached out again to her cock but again his hand was quickly slapped away, but this time she pulled her dress over it and pulled her feet back and put on her shoes.

"Now! Now! Someone's greedy! Lets finish eating first" She giggled from above as Riley heard the sound of plates being put onto the table. He quickly grabbed the fork and got out from under the table. He took a deep breathe of the fresh air outside the table cloth. He was blushing as he got out from under the table as she grinned at him "We can get some desert later.... If you earn it!" She giggled playfully as she began eating, while also making some light conversation. Riley began eating too as he tried to keep up. He could feel her foot on his chair between his legs but not touching him, until suddenly his cock was right between her toes. He yelped and almost stood up as she laughed.

"Wow! You're pretty tiny down there huh?" She laughed a bit "So is that why you like big dicks? You don't have one so big its nice to be around ones that are?"

He blushed bright red "N-no Its just that... I just.. I've just always been attracted to women, but I... Just never liked having sex with them" He had never been asked something like this. Usually by now he would already be on his back or his belly as he was being rammed.

"Oh come on! Obviously you didn't like sex with women! How would you even fuck them with this!?" She moved her foot over his dress and onto his panties, feeling the bulge out and tapping it. Riley blushed as he held her foot in place too embarrassed to do anything about it.

"Well yeah, maybe that was it, haha" He laughed awkwardly, but now feeling braver and more open. "But the first time a futa had her way with me, I realized, I just love cock more" blushing a bit and still laughing he ate more of his food, her foot still in his lap until she pulled it back and leaned forward and put her finger under his chin.

"Well, I think it's a good thing your little dicklet is useless. You would definitely make a better sissy than a man".

Riley blushed as he closed his eyes and was about to kiss her, but she suddenly backed away and laughed. "I think you should finish your food first, then maybe we can go and watch a movie" She took the last bite of her food as she signaled the waiter to get the cheque. "Maybe we can see if you're worthy" She giggled as she went through her purse and paid the bill as Riley quickly finished his food. They both left together. This was Riley's first ever date that was an actual date and not just a booty call. They walked in the street together, Riley holding her arm as he leaned over onto her, feeling a connection as her strong hands held his waist. They spent the next hour talking and discussing what was happening in their lives and shared stories of their past, although Riley didn't tell her everything, he became very open with her and enjoyed her company. Finally, they reached their destination. The Cinema.

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AnonymousAnonymous7 months ago

I'm digging it. Looking forward to more.

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