Frat Boy Turned — Caught

Please read part 1 if you haven't yet! It will give a lot more detail into how I got where I am now.

We left the story when I got my first cage freshman year of college. Honestly not much happened to note the rest of that year -- more parties, casual hook ups, and me fantasizing on my own about locking my cock up and wearing panties.

I guess the one thing to include is I started to explore my hole a bit. Since I didn't have a roommate, I didn't have to worry about anyone seeing the cage. I'd try to wear it for a few hours at a time, at night, and eventually made it a full 24 hours before I unlocked and came all over myself. That was a pretty regular cycle for me the rest of the year.

Around that time I found literotica and started to read more and more forced feminization stories; naturally, my favorites always included chastity cages. Those stories often included butt plugs, dildos, and even real cocks. Things that I always thought would gross me out, yet they only turned me on more when I was locked. I started to finger myself in the shower during my locked sessions, but was scared to order any real toys. I had read about the elusive "sissygasm" as they called it, and dreamed of experiencing that for myself, but we'll come back to that a lot later on.

All this to say, I was going deeper and deeper into the sissy rabbit hole. I was learning all kinds of things and loving all of it. I even stumbled upon sissy hypno for the first time and loved cumming to those videos.

All of this was still just fantasy though. I'd explore it all in private while continuing to lead a 100% normal college life on the outside.

That summer was more of the same. I went home and hung out with friends all summer. Had a couple of fun trips with friends full of lots of drinks and even a little weed. But then I'd get horny and go straight back to panties, my cage, and tumblr/literotica to get my rocks off.

Summer was coming to an end, and I was excited to find out that I'd be living in the fraternity house my sophomore year. Party central. It couldn't get better than that.

I remember packing my bags and contemplating whether I should throw my panties and cage away, but I couldn't bring myself to do it. I stuffed them into a corner of my suitcase and covered it with the rest of my normal boxers. That'd turn out to be a pivotal mistake. If only I'd have thrown them away then, my life would look a lot different now. I just couldn't break the addiction though. That's what it had become -- I was addicted to sissy porn. More so, I was addicted to the thrill of giving up control of my cock. And of course all of the attention I was getting from my thousands of tumblr followers.

I made it to move in day. We didn't get to choose our roommates, but I got paired with my pledge brother, Connor. We weren't really close freshman year, but he was a cool guy. We had the room set up to accommodate both of our mini fridges, couch, double TVs of course, and Xbox's. I unpacked all of my clothes and quickly hid my secret where he wouldn't stumble upon it. I could explain the panties by saying one of the girls must have left them at some point, but would be kind of stuck if he saw the cage.

The first few weeks went along without a hitch. We all picked up right where we left off and were loving living in the same house. Weekend parties were so easy just to walk back up to our room with whichever drunk, hot girls wanted to mess around.

I really didn't post much online those first few months since I was scared to even try to take any pics. The panties and cage stayed hidden, but I was still jerking off to tumblr and literotica pretty regularly when I knew Connor was in class or something.

As the weeks went on, I got more and more brave. I'd even wear the cage under my clothes sometimes while we had friends in the room playing video games. It was exhilarating to know what I had hidden under my sweatpants.

One afternoon, Connor left for class and I knew I had about two hours before he usually got back to the room. I waited fifteen minutes or so to make sure he hadn't forgotten something and had to come back then I put my cage on and my pair of panties (yes, still the same white pair with little pink flowers on them). I pulled out my laptop to find a good hypno to listen to while I read some of my saved stories on literotica. I was planning to goon/tease myself for a full hour. That still gave me plenty of time to unlock and actually jerk off afterward before Connor got back. I locked the door, turned the lights off, put my headphones on, and started reading. (Odds are it was one of silkstockinglover's stories, her sissy stories are top tier).

About twenty minutes in, the lights came on.

I don't think I've ever felt more immediate panic. The only way the lights could turn on is if someone was in the room. And the only way someone could be in the room is for them to have unlocked the door. How did I not hear that?!

I pulled my headphones off, slammed my laptop shut, and grabbed the towel I had next to me to try to cover up. I wasn't fast enough.

"What the fuck?!" yelled Connor. "You could just let me know if you needed some time to jerk off"

"Why are you back already?!" I asked. (His class got cancelled last minute, so he came back to the house).

Ignoring my question and answering my internal question of if I covered myself with the towel fast enough, he asked "Wait, are you wearing panties??"

He locked the door and told me to give him the towel. Knowing I didn't have much other choice, I did.

"Holy shit, and is that a chastity cage under them? I've always wanted to see one in person. I'd ask you to explain, but I know all about sissies. Apparently sissies give way better head than real girls."

"I'm not a sissy!" I exclaimed. But he wasn't buying any of it.

"If you're not a sissy, why is your cock in this little plastic cage? And why are you wearing panties instead of just jerking off like a normal guy? You're a sissy, even if you don't fully know it yet. But I'll help you figure it out."

All I could do was nod as I tried to cover the cage bulge through my panties with my hands. He saw how embarrassed I was and decided I needed to take my panties off. He wanted to see the cage.

I slid the panties off and handed them to him. He told me I'd have to earn them back, but I didn't know what he meant. He bent down to really get a good look at my locked cock, gave the clear plastic cage a flick, and laughed. He pulled his phone out and took a few pictures too. To this day, I don't think I've ever been more embarrassed.

"Here's what we're gonna do," he said. "I'm going to do you a favor and help you become a well behaved sissy boy. In return, you're going do whatever I tell you. If you don't want that, you can always tell me to fuck off and I'll gladly tell all of our fraternity brothers about your little secret. I doubt it would take long for them to show the pics to their girlfriends too. Soon every student here would know. Your choice."

I froze for a few seconds as I tried to process what had just happened. I think I was still in shock that my roommate had just caught me with my pants down, literally.

"I don't expect an answer. What I do expect is for the keys to that little cage to be in my hand in the next 30 seconds or I'll take it that you're going with option two."

Fuck. What choice did I have? I couldn't show my face again on campus if he told everyone. Much less hope to get a girlfriend or even hook up with a girl again.

He started counting backwards from 30. He got to 15 and I knew I had to give him the keys. Maybe he'd even take it easy on me and tell me he was joking. Unlikely, but possible. I scrambled to my dresser, opened the top drawer, and grabbed the keys from under my underwear. I turned and had them in his hand as he made it to 1.

"What a good little boi. I can already tell we're going to have some fun together. But for now, I'm just going to keep these little keys on my keyring so you don't get any ideas and try to unlock yourself. What's the longest you've stayed locked before anyway?"

"Only for a weekend, I usually unlock after I get horny enough," I admitted.

"Well, you don't have that option anymore. I think we'll start off at a week. I'll unlock you to shower/clean, but only if I'm in there with you to make sure you don't try to jerk off. You might wanna make sure none of the other guys are around though when I'm not, because that cage doesn't come off without me until I know you can be trusted."

The fraternity house had community bathrooms, so all of the guys that lived on my floor shared one bathroom. It had two "private" showers, but you could basically see through the shower doors still. Then there was one massive shower with like 6 shower heads for when everyone had to get ready at the same time.

"I'll let you get back to your little sissy session in here, I think I've got all I need for now," he said as he tossed me my panties.

"Remember, no cumming for a week. Unless you can cum in your cage I guess, but I doubt that's possible unless you have some other toys in here. After a week, we can decide if you deserve to be unlocked for a quick release, but I wouldn't get your hopes up. Then we'll start phase two of your training."

Connor headed out of the room with a bit of a laugh. I fell onto our couch with my head in my hands still trying to process what had just happened.

A whole week?! How was I supposed to keep this hidden for a week?? Not to mention, there goes any possibility of hooking up with someone at our party that weekend.

I wondered how Connor knew so much about chastity cages and sissy stuff. He definitely didn't seem like the sissy type, but I didn't feel like I did either on the outside. Based on how quickly he took charge though, there's no way he's submissive. Was he gay? How long did he plan to keep me caged? What would phase two of my training involve??

So many questions. No answers. Just me, my little caged cock, and a big problem.

End Part 2

**disclaimer: while this is partly a true story, I've definitely added some embellishments and details to make it more fun to read. And I've changed names and all that of course.