Groped at Anime Convention Pt. 03

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Man continues to be blackmailed into doing more stuff.
2.7k words
4.57
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Part 3 of the 3 part series

Updated 06/13/2023
Created 01/22/2023
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Author's Note: Sorry it took so long for this chapter, sorta hit a small writer's block trying to decide how I want this to continue.

This is part 3 so go read part 1 and 2 before reading this

tl;dr guy gets molested while cosplaying then is pickpocketed and blackmailed into doing more lewd stuff which leads to him getting blackmailed even more.

It's been a week since that terrible incident with that man from the anime convention. I'm trying my best to forget about it but the dread and fear is forcing me to think about it all the time. The fact that he has a video of me sticking a dildo up my butt and a list of all my contacts is scaring the shit out of me. It's supposed to be summer break and I'm supposed to be relaxing, but how can I relax when this guy can ruin my life at a moments notice.

Just then I hear a buzz from my phone in my pocket. I take it out and see I got a new msg from that guy again.

"Hey baby gurl hows my lil slut doin?" he texts.

"Leave me alone you pervert," I respond.

"Now now, that's a very rude thing to say to someone who helped you have such a fun time, I bet your friends and family would love to see how much fun you had last week," he texts back.

Fuck, he really is gonna blackmail me after all.

"What do you want from me?"

"I wanna fuck your tight virgin pussy ;)."

What the fuck this guy is so weird.

"Well that wouldn't happen even if I wanted to, we both know your cock is way too big, if you fucked me I would have to wear diapers for the rest of my life," I respond

He takes a few minutes before responding.

"Okay here's the deal, I won't leave you alone til I get 1 time fucking you in your pussy and throat, now since you can't handle my massive cock right now, I will train you until you can, once you can handle it, I'll fuck you and then you will never have to see me ever again if that's what you like," he texts back.

I paused and thought for a second, what the fuck did he mean by train? Thinking about him fucking me with his 8 inch massive cock made me want to puke but this was maybe the best offer I was gonna get. He's been honest with me before so maybe he would still be honest with me again.

"Fine if you promise to keep your word then its a deal," I respond.

"A promise is a promise, after I fuck you, you won't have to see me ever again unless you want to," he texts.

"Now here's how its gonna work, we will meet once a week to work on this until you are able to take my cock in your pussy and throat, we can start tonight if you are free," he texts again.

It was Friday night and I had nowhere to be and I guess the quicker we can get this done the better it is for me.

"Fine I can come over."

"Good, come over at 4pm and don't worry about clothes, you can come in your normal clothes for now," he texts.

He sends me the address of his house and I get ready to go over. I tell my parents I'm going to see a friend and that I don't know when I'd be back. This way they won't get suspicious of what I'm actually doing.

I get there at about 4:05 and ring the bell. About 30 seconds later the door opens and I see the same man open it. He looks no different from at the anime convention, wearing a stained white wife beater and boxers. The only difference is that his body odor had somehow become even more foul. Likely combining with the foulness of his house.

"Well then don't be shy come on in, now the first thing you need to is to go into the bathroom and take a shower, then I want you to shave everything except your hair, you'll find a razor in the shower, take your time," he said.

What does me shaving have to do with anything I thought. I didn't care that much though because I didn't grow much body or facial hair anyways. I stepped into the shower and noticed that he had only feminine body wash and shampoo that made me smell like roses. What the fuck is this what he usually uses? Then I remembered his awful odor and knew that couldn't be the case, he left this for me I guess. I ignored it and finished washing and shaving myself afterwards.

I then stepped out of the shower and to my horror I can't find my clothes anywhere. Instead I see a small pair of pink panties and small pink bra.

"What the fuck," I say out loud.

"Can't have you wearing the same thing you wore before the shower, defeats the whole purpose," he yelled from the other room.

"Now quit whining and put it on, you will look cute in it anyways," he added.

I begrudgingly put it on and walk out the bathroom to she him. He's sitting on the couch in front of his TV watching football when I come out. He pauses it and looks at me.

"Damn girl you do look fine, alright first things first were gonna need you to get used to having something in your butt if you are gonna eventually take my cock and this will help," he states as he pulls out a small 1 inch diameter buttplug.

"Y-you want me to put that in my butt?" I ask.

"Yes you will need to wear that for as long as possible in order to help make you able to take my cock, now quit complaining and bend over the table," he says pointing to his dining table.

I reluctantly walk over to the dining table and bend over it. He then walks up behind me, his shadow completely covering me up. He pulls my panties to the side as I feel a liquid touch my butthole. I yelp from the shock of how cold it was.

"Relax girl, this will help it slide in so it doesn't hurt you too bad, although since you've already taken a 5 inch dildo, a 1 inch diameter might not be that bad," he says as he chuckles.

I then feel the buttplug poke inside me and I yelp again from the shock. Then a few seconds later and its completely inside me. He then pulls my panties back into place and then slaps my ass which causes me to moan.

"See it wasn't so bad, you're feeling good already," he laughed as he said this.

"Alright now I'm gonna have you move around a bit with that inside you so that you can get used to the feeling and become more comfortable with something that wide inside you. Firstly I want you to clean up and take out the trash from the house then I want you to do the dishes, after that come back to me and I will tell you what to do next," he stated.

What the fuck I'm basically this guy's maid at this point. But whatever not much I can do at this point, I'm stuck here until he gives back my clothes so I have to do whatever he says, at least it wasn't sexual.

Cleaning up and doing his dishes were disgusting though, it seemed like he hadn't cleaned up in ages and everything smelled horrible. I nearly puked several times while trying to clean up but I finally got finished about 30 ish minutes later. At first the buttplug was annoying me, but after awhile I sorta stopped noticing it and it sorta felt good. When I got back to him I saw him on the couch watch football yet again. I stand there for about 15 seconds before he finally notices.

"Damn girl you finished that pretty quickly, you'd be a good maid or housewife," he laughed loudly at his own joke.

"Okay damn that was good, alright then now I'm hungry and thirsty, go make me a nice sandwich with ham, cheese, lettuce, and mayo, and also get me a cold beer from the fridge," he firmly commanded.

What the hell, he's basically just making me his slave at this point. I quickly throw together what he asked for and walk out to him and place it on the coffee table in front of the couch.

"Thank you baby girl now come sit down next to me and watch the last quarter of the game," he says while putting his arm around me and pulling me onto the coach.

He doesn't even give me any time to protest as he pulls me up close next to him with his right arm. My head is pushed straight into his fat chest which makes me shudder in disgust. His arm keeps me locked up against his body with no room to squirm.

With his other hand he picked up the sandwich I made for him and took a big bite out of it. I could hear him chewing loudly with his mouth open which disgusted me even more. He then leaned down to look at me while moving his right arm up to my head. He leaned in closer and began French kissing me out of nowhere. It was even more disgusting because he had barely swallowed any of his sandwich cause my mouth to get filled with his saliva mixed in with the sandwich I made for him. It was so gross it made me feel so weird.

"What do you say to daddy?" he asked.

"Thank you daddy," I quietly said back out of obligation.

"Hehe good girl," he chuckled.

We finished watching the game and it was about 5:30 pm.

"Alright girl we only got two more things to do today and then you can go home," he stated.

He turned around and grabbed a blue dildo.

"Your gonna spend 15 minutes practicing giving this 6 inch dildo a blowjob and then 15 minutes sticking it up your pussy, we will slowly work you up until you are able to take my 8 inch cock," he stated.

Fuck he was gonna watch me masturbate again and there was nothing I could do. This time I was even more naked that before. I slowly walked up to him and took the dildo from him.

"Now lets go to my bed for this so you can get comfortable while you are doing it," he said as he guided me towards his bedroom.

After arriving I got up onto of his bed which smelled disgusting just like him, while he grabbed a chair to watch me.

"Start by blowing it and make sure to face me while doing it, I want you to look at me while you go down," he stated firmly.

"Yes daddy," I say as I begin going down on the dildo. This one is noticeably harder to keep down as compared to the one at the hotel, but it isn't impossible. I periodically remember to look up at him to make sure he doesn't get mad at me. When I look up to meet his gaze I see him looking a me smugly as his dick gets noticeably bigger in his pants.

After about 15 minutes he tells me to switch to my butt and I slowly pull out the plug I had been wearing up until now. I kinda forgot I had been wearing it until now and taking it out made me feel weird as there was a clear hole in my butt. I then began slowly inserting it into my butt just like I had done before. It wasn't even that bad despite the size upgrade since my butt was already spread a bit due to the buttplug.

After about 5 minutes of pushing it in and out of me it begins to feel good again just like in the hotel and with my free hand I go to rub my penis through my panties making me feel good.

"Hold up stop everything," he yells.

Before I can do much however he gets up from his chair and grabs my hand I was using to touch my penis.

"I don't want you to get yourself off using your hand, that defeats the purpose, I want this to be good training for you. You need to learn to focus on the pleasure from your ass not your penis," he states.

"Come with me we need to do something before you finish" he says while dragging me by my arm to the kitchen.

"If you can't behave on your own then I will make sure you don't act naughty,"

He then grabs an ice pack from the fridge and presses it up against my penis which causes me to scream from the cold. He then pulls out a small pink thing that sort of looked like a cage.

"This is called a chastity cage and it goes on your penis to stop you from being naughty," he says.

Before I can say anything in protest he leans down and pulls my panties and puts it firmly on my penis, he then pulls out a key attached to a thread and locks it in place. He then puts the key around his neck like a necklace and tucks it under his wife beater.

"Now that we got that all sorted out we can finish the last 10 minutes of your session and you can go home," he say.

I try to say something but I can't think of anything, I go back to the bed and finish what I had started. It still felt good and I had the urge to rub my penis but couldn't. It was like heaven and hell, it felt good but the fact that I couldn't act on it made me feel agony.

"Alright its been 10 minutes then you can stop, now don't forget to put your buttplug back in, you should be wearing that whenever you can, at least if you want to be able to get this over with any time soon," he said calmly.

I looked down and noticed my panties were still somewhat wet, I guess even though I couldn't get hard it still dribbled a little precum through my cage. Maybe once I get home I can relieve myself.

"Here's your clothes, no need to go to the bathroom you can put them on right here," he stated.

It took me a second but I noticed that my underwear were missing.

"Where's my underwear you pervert?" I asked.

"Your wearing a perfectly good pair of underwear right now, so quit whining and put it on" he firmly demanded.

"Wait, wouldn't it be easier to take off the cage now, rather than when I put all my clothes on?" I asked curiously.

"Haha, what made you think I would release you so quickly afterwards? You need to spend more time getting used to using your butt, I can't let you go masturbating with your penis right now. Once we are done together I promise I will let you out, but until then it will be best to keep it locked up," he calmly said.

I silently pouted and the fact he wasn't gonna let me masturbate until I let him fuck me in the ass. I begrudgingly put my pants and shirt on as he showed me to the door.

"Wait before you go here take this," he said while handing me the 6 inch dildo.

"I expect that you play with it at least once a day, trust me its best because next week I'm bumping you up an inch whether you're ready or not so you better practice so it doesn't hurt next week okay?" he said while patting my butt.

"Yes daddy, thank you," I said while walking out the door.

I quickly made my way to my car as I thought about what just happened. Great, I'm gonna probably have to see him a couple more times at the pace were going which means I might not be able to masturbate for a month. This was definitely going to be hard.

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AnonymousAnonymous28 days ago

I loved the entire series up to the end of this part. More please, like another part. It's very good, and well written.

AnonymousAnonymousabout 2 months ago

Wow i loved this i looked up the character you were dressed as for the convention and its amazing i loved how girly it is something id love wearing. Change your name to Brianna soon as you know what is going to happen your getting erections and enjoying what he is training you to do and soon daddy will make you his girl and fuck your boipussy and give you his semen. Prepare yourself for having your cherry popped it will be amazing and you will want it again. Why do i say that because i know as i dress girly since my early teens and love having a daddy fuck me like a girl. Having a sissygasm by penetrating your boipussy is a wonderful feeling but when you are penetrated by a penis and filled with his semen is even better. Like you i have a similar size erect quite thin and my sissyeggs are small. I used to be ashamed how tiny my ladycock was but daddys love it so now i love my size. Keep writing id love to hear how your daddy mounts you and fucks you and how the ezperience changes you. SissyErica UK

AnonymousAnonymous5 months ago

Hi there, just finished the last chapter, ;), Mommy told me to never say bad things about things so i won't. Have a great day.

AnonymousAnonymous7 months ago

Really looking forward to the next part(s)

sissy8oysissy8oy9 months ago
I love these

I hope you are able to write more stories soon

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