Holiday slut: Orgin story

The date was June 1st, a date I would not forget. My girlfriend was out for the day and I was feeling horny. I was pretty sure she was cheating on me, and well I was lonely. I messaged someone on a hookup site. She looked cute, sweet, innocent even. Oh how that was wrong. I set it up, I was thinking with my dick I'll admit it.

Her name was Jamie. Jamie said to meet her at her place. I went in and immediately she was on me. She kissed me passionately, deeply, like she needed me. She lead me to the bedroom, I stripped quickly while she ran to the bathroom. When she returned she was wearing a black negligee, and panties she told me to get on the bed and put on the blindfold. She said she was kinky so I didn't ask questions. Why was I thinking with my dick. She started sucking my dick, slowly at first but she knew what she was doing. She teased me for a while until she was ready for me to enjoy myself. She throated me hard, she'd clearly sucked more than her fair share of dick. I grabbed the bedposts and flexed as I writhed in pleasure.

"Jamie, you gotta slow down, you're gonna make me cum before I get inside you!" I half yelled half moaned.

Jamie came up for air "Oh no, we don't want that. Tell you what I do want though, I want you handcuffed to the bed."

I agreed, I didn't think anything of it either. I figured it would give me a hint of respite to gain some stamina back. Hell maybe I'd eat her pussy for a bit. Ha, yeah I was completely oblivious. She handcuffed me to the bed, all fours. As much as I begged she didn't let me eat her pussy. Probably should have been a hint. She applied lube to my cock and slid down my cock slowly. I knew I wasn't in her pussy. She started riding me, slowly grinding her ass on my groin. I held out but it was obvious I was loving this. She rode me and started talking dirty to me.

"You like fucking my ass?"

"Fuck yes!"

"Is anal your favorite?"

"I fucking love anal baby"

"Yeah, I know you do, you want me to play with your ass? I think it's hot when boys aren't weird about their backdoor."

"Sure, you can play with my ass!"

"MMM! Baby you are exactly what I need!"

"Oh yeah baby I was made for a girl like you!"

"Oh, you like girls like me huh?"

"I fucking love girls like you baby, I need girls like you baby!"

"Oh yeah? How many girls like me have you fucked?"

"No where near enough baby!"

I felt her hand gather lube from my cock and started lubing my ass. I had never done anything with my ass, but she baited my responses out of me. I should have suspected something then for sure but I was on another planet. She fingered my ass rather sloppily honestly but I guess that's to be expected she was still riding me. She started moaning hard, clearly playing with my ass was turning her on a lot. Her moaning was getting me in the same place. I knew I wouldn't last long, I didn't think she would either. She pulled her finger out of my ass and started grinding on me hard. She was squeezing my cock hard with her ass.

"Oh man you're going to make me cum just fucking my ass!"

"Yeah baby? Is that good cock?"

"Mmmm the best baby, are you getting close too?"

"Fuck yes! You keep squeezing my cock! I'm sitting right on the edge!"

"Good baby, let's cum together then!"

She pulled herself off me and started jerking my cock fast. She was masturbating over me and I could hear it. We moaned back and forth for less than 30 seconds. We both came at exactly the same time. I'm sure she planned that. I came, really hard. I felt my cum hit my mouth, face, and chest. I didn't want to react negatively and honestly I was mid orgasm and reacting wasn't really possible then. She was moaning and cumming at least as hard. She made a lot of impressed positive moans. I still had no idea. Then she started in with the after care.

"Oh baby, I got cum all over your face, I hope that's ok, it was an accident, I mean I think it's hot as fuck but I didn't mean to!"

"It's ok, girl, if you think it's hot I'm ok with it."

"Oh God you are the best! Would you lick a little bit of it up for me?"

"Sure baby!"

I licked a bit of cum off my face and held it out on my tongue on display for her. She kissed me aggressively, sucking the cum out of my mouth. She started licking the cum off me and feeding it to me via aggressive kissing. We did this for about a minute.

"Mmm baby, that was so fucking hot! Now that we've cleaned you up let's get that blind fold off!"

I heard a beep to the left of me and my blindfold was removed. I was in utter panic then despair when I saw my girlfriend Alex, holding a camera right next to the bed. I looked down and noticed that Jamie had a cock! A tiny cock was hanging out of her panties slowly going flaccid. I panicked, my eyes went wide as planets! I started hyperventilating. I wanted to yell but since i was still tied down I had no idea what to do!

Alex piped up.

"Alright, here's the deal, I've got about 10 minutes of really high quality video here that shows you are a premature ejaculator, into t-gurls, and a cheater. If you don't want this plastered on your social media and personally emailed, texted, and mailed to everyone in your phone you're going to do exactly as I demand, sound good?"

I nodded, dumbstruck by what I was hearing.

"Good, you're going to be exactly like Jamie here, mine to do with as I please, you'll be in chastity all day everyday, I will hold the key. You will be let out on holidays, holidays only! You're going on hormones, and you will be my third fuck toy. The other two will use you every week, I will use you every day. You'll serve me in anyway I see fit, if I want you to get surgery, you will get surgery. I own you completely, from this moment forward. Do you understand?"

I nodded solemnly, slowly, knowing I have no other options. If I didn't agree I'd be homeless, single, and no one in my family would talk to me. I'd be fired for sending that video to everyone in the office, I'd be ruined. In a literal day my life would fall apart completely. Sure my life would be drastically different but at least I could break news to people selectively. I'd still have a place to live, a job. I knew it was the only choice I had.

Alex motioned and Jamie went to get a chastity cage.

"Good, we'll cage you, give you your first dose of hormones, and send you on your way while we make a few copies of this. Well, while I make a few copies of this. Jamie is going to eat my pussy while I watch this a few times. I'll give you a pass for today. You don't deserve to eat my pussy today. When I get home you'll be in a dress and panties. Can you handle that?"

She glared at me while I nodded. I still had no words. I was trying to wrap my head around what was happening, while Jamie affixed my cage. I felt a stabbing sensation in my stomach, as Jamie injected hormones into me, and finally I felt my tight ass stretch around a small butt plug that Jamie slid into me. I was overwhelmed, but I had a feeling that my life as I knew it was over while I felt deeply uncertain I wasn't really scared. I felt like everything was going to change but it would be ok.

Jamie looked at me and while absent mindedly playing with my caged cock told me,

"Don't worry, you'll get used to it, your cock is going to shrink, and you're ass is going to loosen up. You'll learn how to suck cock, how to actually please a woman, and you'll learn how to do what I did to you with my ass! I'm not gonna lie, she's pissed. She knows and cares for you a lot, but she never thought she'd have to make you into a sissy. She's told me the sex you two have is mediocre, and she wanted to work on it with you, but now, well you two will probably never have sex again at least not like you have. You're not her boyfriend anymore, you're not even a lover to her anymore, now you're a vibrator. Hell, you're not even that, you're basically worthless to her. It's gonna be rough being you for a while. Keep your plug in, it comes out for bathroom time and that's it. If you get out of your cage without her permission she'll leak the video. If you ever think you can without her knowing just remember the first thing you did she didn't like was try to hook up with me. Do you think that is a coincidence? Alex is scary smart, and knows waaaayyy more than she lets on. This is your life now, accept it or accept the alternative. At least this way you'll get out on holidays. Anyway I gotta get in there and calm her down. I'll do what I can, but I'm not sure any amount of orgasms will make her forgive you. That will take time, submission, and commitment."

Jamie unlocked my handcuffs and showed me the door. I still didn't know what to say but I finally found some words.

"Thank you for the advice, thanks for what you're about to do. You're a nice person and you have a lovely home."

"Don't sweat it, sorry you chose me, She kinda set you up but still, I feel a little bad. I am excited to have a new person in our group though! I have to admit watching men slowly turn into a sissy mmmm I like it a lot. Can't wait to see you again. You'd better get home, I've got a lot of pussy to eat."

She closed the door and I headed for home, my whole new life ahead of me.