Asian couple vacation Ch. 01

Story Info
Boy gets locked in chastity before trip with shy girl.
5.2k words
4.6
28.1k
37

Part 1 of the 3 part series

Updated 04/21/2024
Created 03/14/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is a completely new series using recycled characters but in a completely different universe. This story is purely fiction, all characters and events are fictional, any resemblance to actual people or events is purely coincidental. The story contains public play, F/m sex, mild Dom/sub, femdom, non-consent, and chastity. This is a multi-part series focused on shy but sex-craved Asian friends going on a holiday. This story sets the stage on the conditions before the trip.

It was late afternoon, just after the lunch rush, and the restaurant was not too crowded. Lillian and Cassie sat in a U-shaped booth near the back of the restaurant. Lillian had just broke up with her boyfriend a week and a half ago. She was definitely saddened by it and wanted to get her mind off things. Cassie, her roommate, took her out for lunch.

"Oh come on Lillian," said Cassie, "don't feel so down. I know he's your first boyfriend you've ever had but there are lots of other guys out there. It probably sucks that he took your virginity!"

Lillian blushed, she was always shy about intimate stuff due to her conservative upbringing and her inexperience. She acted innocent and always felt embarrassed talking about intimate topics. Lillian was a 22 year old slender Asian girl who just finished college. She was a 5ft4 girl with wavy hair down to her shoulders, smooth pale skin, small but perky breasts, flat abs and toned legs. She was wearing a halter top and a short summer skirt.

"Tell me, Lillian," continued Cassie, "was the sex good? If not, here's your chance to date and sleep with other guys. Experiment a bit and see what you like. Enjoy a bit, go wild for once!"

Cassie, her roommate, on the other hand, was older and more open. She was 28 year old, 5ft9, bustier and was a more confident and assertive Asian woman. She was always the older sister type bossing people around.

"I don't know," replied Lillian, "I think I just want to take my mind off things. We booked that trip to Europe leaving in a week and then you had to cancel at the last minute. Now I'm thinking if I'm ready to go so far away for so long by myself."

"Ah yes, that trip I made you book after you broke up with that guy. Don't worry, I have found someone who can take my place and chaperone you."

"You did? Who is it?"

"You know him, he's coming for lunch."

"Him?"

At that moment, Brandon showed up at the restaurant and greeted Lillian and Cassie.

Lillian was surprised and was not expecting Brandon to show up, let alone accompany her on her trip to Europe. Brandon and Lillian had been friends and classmates since they were in college. Brandon had a crush on Lillian since last year, but she was dating another guy at the time.

"Hey Brandon!" said Cassie, "come have a seat!"

Cassie scooted over in the U-shaped booth. She was in the center of the booth while Brandon and Lillian were on the two sides facing each other.

Lillian whispered to Cassie, "He's going to take me to Europe? You told him? I can't travel with a guy?!"

"Shush Lillian, I haven't told him yet. Let's order food first then we can talk."

The three of them ordered and ate while Cassie explained the meet up.

"Thanks for coming to lunch Brandon," said Cassie, "I'm going to be direct with you on why I invited you. I know you don't start your job until after summer, so you have this time off. I have a favor to ask you. Can you give up your free time and accompany Lillian on her summer trip to Europe? It will only be for a month, unless she decides to extend it.

"I know it's a bit last minute to ask you about this, her trip leaves in a bit over a week, so I really appreciate it if you can be her chaperone. You know, take her to the airport, to the sights, keep her safe, make sure no creepy guys are hitting on her..."

"Cassie! He's a guy, I can't be going with him and sharing a room and all that," interrupted Lillian.

"Oh Lillian, stop being so picky. Face it, who else would go with you besides me or Brandon. All your other friends are timid and boring. They're either no fun or too scared to even travel. Plus, Brandon is a young sexy guy, at least he's easy on the eyes and look at those muscular arms, he can definitely protect you," said Cassie, looking at Brandon in his gym tank top after his workout.

Indeed Brandon was a charming and handsome Asian guy. He was 21 year old, 5ft8, smooth, slightly tanned, and an athletic build with a well-defined chest.

"Well Cassie, Lillian," said Brandon, "I'm honored you invited me to your trip. You're right, I don't start work until the end of summer, so I do have some free time. I can definitely go away for a month or two and help Lillian. Plus it will be good for her to travel and get her mind off things."

"But he's a guy," protested Lillian, "it's going to be so awkward being with him and sharing a room or a bed and all that."

"Lillian, you've known him for many years now," said Cassie, "he's your friend, there's nothing wrong with traveling with a guy friend. Who knows, maybe you two might spark some romance on your trip."

Lillian stayed silent, biting her lips, trying to think of what to say next.

"Stop being so whiny Lillian," continued Cassie, "you're an adult now. You've seen your boyfriend naked so you know how guys are and how they behave. You should trust that he'll protect you. Were you expecting to have sex with him all the time? How many times have you had sex with your ex-boyfriend?"

Lillian gave Cassie an awkward and embarrassed look and didn't respond.

"Ok Brandon," said Cassie, "how many girlfriends have you had? And do you feel awkward about traveling with a girl?"

Brandon replied, "Well, to be honest, I've never had a girlfriend before. But I'm totally fine with traveling with Lillian and taking care of her."

"Really? You've never dated before? Are you a virgin? or gay?" asked Cassie.

"No! I'm not gay. I, ehh, hooked up with a few girls before. But I promise, I won't do anything that will hurt Lillian or make her feel uncomfortable. I'll do anything both of you say."

"You hear that Lillian? He'll do anything for you on the trip. You shouldn't have to worry. I can see he's obedient and passive. He'll be like your little handsome boy toy and do whatever to satisfy you. Isn't that right?"

"I guess you can call it that."

"What do you say Lillian? Take him with you, what else are you afraid of?"

"Well, you know, he's a guy and I'm a girl, it's just that..." said Lillian.

"Ok, I'll be blunt," said Cassie, "You're trying to be all innocent and precious. Are you afraid that he's going to masturbate in front of you or try to have sex with you? With his little pecker."

"His what? I didn't mean that!"

"Face it Lillian," continued Cassie, "You think all guys are out to fuck you, maybe they are, maybe they're not. But maybe in reality, you're just as horny for dicks and just won't admit it."

Lillian was speechless, but she wasn't mad. In some ways, it was true, Lillian had been craving more sexual liberation but was too afraid to publicly express it. And she felt pressured around Brandon and Cassie.

"Ok, I think I have a solution," said Cassie, "we'll lock his pecker up in a chastity device the entire trip. That way you control his pecker, he can't possibly masturbate or have sex, and you'll be safe. Plus he'll be horny and will probably do anything for you the entire time."

Brandon was shocked, but oddly enough, he has read about chastity devices on the internet. A plastic or metal cock cage that prevented erection. If he wore one all trip, he would not be able to get hard or cum.

"Wait what?!" protested Brandon, "You want me to do what all trip?"

"Please Brandon," pleaded Cassie, "can you do this for her? She just broke up with her boyfriend and needs someone to go with her and feel safe. I know you like her so how about a bit of sacrifice for our friend, just to see her happy?"

"What is a chastity?" interrupted Lillian.

"A chastity device is a thing that goes around his penis and prevents him from having penetrative sex with you or any girl for that matter. It also prevents him from masturbating and giving in to his sexual urges.

"He can show how committed he is by giving up control of his dick and his sexual urges to you. You can hold on to the key and you decide when he gets to cum. If he behaves and is a good boy, then maybe you can reward him. It's a great way to control a guy."

Brandon thought for a while, about giving up cumming all month. He has always fantasized about being submissive to a woman or couple. One who would boss him around and make him serve them. He liked the thought of having the girl he liked controlling his cock. It could be worth it if he showed her how loyal and obedient he was, he could use it as a chance to profess his love for her on the trip.

Brandon looked up at Lillian and said "OK if Lillian is ok with it, I'll do it for her, to make her feel safe."

"Great," said Cassie, "what do you say Lillian? He'll be locked up all trip and accompany you. You won't have to worry about his penis or him making unwanted advances."

Lillian was uncomfortable with the conversation and still didn't even know exactly how a chastity device worked but was warm to the idea that Brandon will stay obedient and be serving her and not do anything sexual.

"Ok Brandon, let's get some measurements of your dick so I can fit you with the right cock cage," said Cassie. Since they were in a secluded booth in a nearly empty restaurant, she instructed him to take his shorts off.

"Can we just do it in the car or the bathroom?" asked Brandon.

"No, do it here so I don't have to move. Plus Lillian is on the other side, she can't even see your dick. We'll keep it under the table, it's private enough here."

Brandon felt uneasy but seeing that the place was almost emptied out he obliged and rolled his shorts down to his knees. His cock flopped up, it was already hard from all the talking. It was an average sized 5.5in uncut cock.

"Whoa, you sick little pervert, it's already hard from our conversation! We'll need to get that soft before we take measurements," said Cassie, "let me jerk it for you."

Lillian was embarrassed but also started to get horny. Although she couldn't see anything, the thought of her roommate holding her friend's erection on the other side of the table made her wet. She reached down her skirt discreetly and felt a wet spot in her panties. She wondered what her friend's cock looked like and how it compared to her ex-boyfriend's cock.

She has never experienced any public play before, so this was definitely turning her on. She started to fantasize more about Brandon being naked in public or just naked in front of her. She was turned on by his vulnerability and helplessness and submissiveness. Maybe it was something she could try out on their trip.

"Wait, you can't just jerk me off inside the restaurant!" whispered Brandon.

"Well how else is it going to get soft, you want me to get some ice?"

"No no, let's just jerk off and get this over with."

"Good, it should be fast, your dick doesn't look or feel that big anyways."

Brandon looked embarrassingly at Lillian, not knowing what she was thinking, hearing about the size of his cock.

Cassie continued to rub her hand on his Asian cock. It was slim and fit perfectly in her hand, she rubbed his foreskin up and down and squeezed some pre-cum from the tip of his penis head. She rubbed her thumb around the wet tip of his penis.

Suddenly, they were interrupted by the waitress, a slim pretty white girl in her mid 20s wearing a skirt uniform and thick framed glasses. She came by and threw down 3 cups of coffee and said, "Here you go, 3 after meal coffees. Would you like any cream and sugar with it?"

Cassie responded, as if nothing was going on, "No cream or sugar needed, we can milk our own cream. How about you bring us a little glass?"

The waitress looked at Cassie then looked down at Brandon's crotch and clearly saw what they were up to. The waitress winked back and said, "I'll bring you a glass, hope that cream is tastier."

Seconds later, the waitress came back with a little glass and took another look at Brandon's pink exposed cockhead on full display with Cassie's hand gripping his dark shaft. "That glass better be full when I get back," the waitress snapped back.

Cassie continued to stroke Brandon's cock and then placed her palm in front of Lillian. She told Lillian to spit on her hand. Lillian didn't quite seem to understand the reason.

"Spit on my hand! Got to give him some lube so he can cum. I can't be stroking his little dick all day!"

Lillian gave Cassie some spit and Cassie continued to rub Brandon's cock. Brandon was now fully aroused. He was embarrassed and tried to look away from Lillian but he fantasized about her stroking his hard cock. He wondered what she would think of his cock and how horny he would be serving her in a chastity. What if she made him lick her sweet pussy during the trip. He looked at her once more until the point of eruption when he closed his eyes.

Lillian was very wet by now. The public play and Brandon about to cum in front of her were making her very aroused. As he closed his eyes for his imminent orgasm, Lillian quickly slipped her hand down her panties and rubbed her moist clit. How badly she wanted to cum as well with Brandon in front of her. She looked straight at his orgasm face about to give a faint scream.

Brandon gripped Cassie's wrist as he was about to cum and Cassie quickly grabbed the glass to capture his creamy load. He shot 4 loads into the glass, it was a heavy load that filled a quarter of the small glass.

"Wow, big load," said Cassie, "when was the last time you came?"

"Around 2 days ago," replied Brandon exhaustingly.

Cassie put the glass down on the table. Lillian's eyes opened up and was surprised at the huge thick load that Brandon had. Her ex-boyfriend never had such a big load before so it was clearly something new for her. She got horny again thinking what if she was covered in all that cum.

"Nice, can't wait to see what it will be like after a month!" said Cassie, "I think Lillian you should drink it, to partake in our little fun."

"Ew no! That's gross," said Lillian, "that came right from his you know where!"

"You mean your ex-boyfriend never made you swallow?"

"I mean he tried but I spit it out everytime."

"Just take a sip, get out of your comfort zone! Add some kinky fun to your life!"

Lillian was hesitant, she put the glass up to her lips and took a small sip before putting it down. She felt embarrassed to be drinking her friend's cum and inside a restaurant. Her small Asian lips were covered in her friend's moist milky seed.

The snappy waitress came back and saw Brandon's now deflated cock and the glass filled with his cum. She said, "Wow that little cock sure had a big load and none of you wanted to taste that warm creamy load?"

The three of them all looked at the glass then back up at the waitress. The waitress took the glass and gulped it all down and said, "Yum, bitter and sweet, never tasted Asian cum before." She gathered the glass and some leftover plates and walked away.

Cassie then pulled her phone out and used an app to take some measurements of Brandon's soft cock. She pulled his foreskin back to expose his head and took a few more pictures. She noticed that his pubes were trimmed but told him that he needed to be fully shaved before putting the cage on.

"All done," said Cassie, "now put your pants back on and we'll have your cage on in a few days. Any questions boy? Remember, from now on, your dick is going to be locked and Lillian is going to be in control. You'll be doing anything she wants on her trip and if you upset her, you're not going to cum. Got it?"

"Yes ma'am," said Brandon looking at Cassie then to Lillian, "I'm going to do everything Lillian says on this trip and be obedient. Rest assured, I won't do anything to upset her or hurt her."

***

A few days passed until Cassie sent Brandon a text message to meet up to give him his chastity device. She told him to go back to the same restaurant in the afternoon during the quiet hours between lunch and dinner.

When Brandon got to the restaurant, he didn't see Cassie and sat down at the empty booth at the back again. He waited a couple minutes until the same waitress from last time came to his table.

"You're the Asian boy that was jerking off a few days ago right?" she asked.

"Uh, yes," replied Brandon trying to avoid conversation or get in trouble.

"Good, your domme friend gave me your cock cage and told me to lock you up," she said.

"Uh what? Ok, I can go to the bathroom and put it on."

"No, she told me that I had to supervise and lock you up myself. I know it sounds humiliating but you're going to be a sub soon. I know how you subs think, you crave a woman dominating you."

Brandon didn't say anything, he was not prepared that his submissive summer vacation would start with being locked up by some random waitress.

"There are no customers right now, let's go to the bathroom and get this over with," she told him.

He followed her back to a large and clean gender neutral bathroom.

The waitress locked the door and pulled out a black plastic chastity cage along with the base ring and lock. It looked to be 3D-printed made to fit his limp cock perfectly. Brandon looked at it and felt a bit terrified, not knowing what he was getting into. The cage looked smaller than what he was anticipating.

She looked him in the eye and said, "Strip!"

Brandon didn't know how to react and looked back right at her.

"I said strip, boy. I need to lock this tiny cage on your cock."

Brandon felt vulnerable. He felt humiliated to have this random white girl he met a few days ago to tell him to get naked. Yet the power she exerted over him turned him on. He slowly pulled his shorts down and revealed his navy blue briefs.

"Everything off! Tank top and briefs!" the waitress said, "I want to see that fit Asian body of yours. And you sure you're not gay? You sure like to show your muscle and skin for a guy."

"Thanks, I try to stay fit. And I'm not gay."

"Well whatever, hurry up, boy, take your top and your undies off! And throw them over in the corner by the door."

Brandon hastily took his top off and then pulled his briefs down and threw his pile of clothes to the door. He was now stark naked in front of this random waitress who was about to lock his cock up. He was scared and aroused at the same time with his cock was starting to get hard.

The waitress walked over to him to inspect him and said, "Wow, you're really enjoying this aren't you? Your cock is getting hard from me dominating you. Look at that athletic body, nice muscles. Looks like you shaved all your boy hair as well, all ready to be locked up. A smooth locked sub."

Her teasing and talking made him even more horny and by now his erection was at full mast.

"So boy, are you ready to have your cock locked up for your girlfriend?"

"Yes ma'am."

"Yes what?"

"Yes ma'am, please lock my cock up so I can submit to my friend."

"Good boy. Once you're locked, you will treat her with the respect and give her the praise she deserves. She will decide when you can get pleasure, if at all."

"Yes ma'am."

"But your cock is rock hard right now, I can't possibly fit you in this tiny cage. What to do."

Brandon looked at his cock and knew there was no way it would soften with so much teasing. He wasn't sure what to say, hoping she would jerk him off like what Cassie did a few days prior.

She gave him a kiss on the lips and then a deeper kiss forcing her tongue in his mouth as she gripped his 5.5in uncut hard cock and started pumping it. He tasted her tongue in his mouth as she stroked his hard cock and rolled his foreskin back.

12