Frat Boy Turned - Shopping Day

**Disclaimer, the first two parts of this story are available on my profile. They give lots of backstory, but aren't necessarily required to read before this one!**

I had a late afternoon class that day, so I knew I had to pull myself together. It took thirty minutes or so for me to truly accept my predicament before I glanced back at the time and realized I needed to get a move on. I put on some boxer briefs and got dressed then began my walk to class.

My class was on the other side of campus and the entire walk I felt like everyone knew what was under my pants. Obviously they didn't, but it's a wild experience being caged in public for the first time. I made it to class on time and tried my best to focus on anything but my locked cock (sadly not with much success). I couldn't tell you a single thing my professor talked about that day.

Finished class and made it back to the fraternity house. Connor was playing Call of Duty in our room when I got there. I sat down on our futon and grabbed a controller for the next game trying to act normal. He finally broke the silence and asked if I wore my panties to class.

He seemed disappointed that I didn't and told me I had a lot to learn. He told me he expected me to wear panties the rest of the week, but I only had the one pair.

"Looks like you've got some shopping to do before you can play CoD tonight. I know this is overwhelming though, so you can do your shopping online for now. I'd suggest Amazon, so you can get one day delivery. Eventually you'll be shopping at Victoria's Secret though to pick out your lingerie in person. Find at least a week's worth of new panties - but make sure you try different kinds. I don't want you just to stay in the basic pair you have now. Speaking of, you need to put them on. If you're going to play around like a girl, you need to dress like one. Plus, there's no need for extra room in your underwear knowing your little cock can't get hard anymore. If I catch you in normal underwear again, you'll regret it"

I pulled up my Amazon app and started my search. There's lots of "sissy panties" made specifically for men, but I really loved how real panties felt. I knew my waist/hips measurements, so I could make sure the sizes I ordered were correct. I added a red, lacy thong to my cart first. Then I found a pink Victoria's Secret thong that I really liked too. I found some cute hipster and bikini cut panties too with little designs on them. Lastly I got a pair of baby blue striped cheeky panties.

My cock was straining in my cage the whole time as I already was picturing myself in them. I couldn't deny that I loved this. But Connor didn't need to know that.

Connor wanted to see my cart before I ordered, so I told him I was finished and handed him my phone.

"Damn, you really are a sissy. I don't think I could have found anything girlier than these. Nice choice on the thongs by the way, I'm sure you'll feel like a real slut wearing those to class. I approve, you can order them."

I placed the order and he handed me my controller. The rest of the night was completely normal. Neither of us acted like anything was different - just two normal college guys playing video games and drinking on a weeknight.

I didn't sleep much that night thanks to the cage. I had never really tried sleeping in it before. But the nighttime erections were brutal. I was straining in my cage basically all night. Luckily I had an 8am class the next morning, so I had to get up pretty early anyway. I got dressed for the day quietly trying not to wake Connor. But apparently he was awake because right before I left he made me show him my cage and panties for the day.

"Can't wait to see all your new panties tonight sissy boy".

Pretty normal day outside of grabbing the package from my mailbox in the student center and then the "fashion show" for Connor that night. He told me to wear the red thong the next day. He apparently had plans for us after class. I still wasn't sleeping well, but didn't really have much choice but to get used to it. He assured me it would get easier after a few nights.

"I'll pick you up after your Econ class today. We've got to run a few errands."

I was pretty worried about what he meant by that, but couldn't deny that it turned me on a bit too based on the wet spot in my panties. He was waiting on me outside of the business school at 4. I climbed in his 4Runner and he started driving to town.

"I went through your stuff and realized you really don't have any toys, unless you're just really good at hiding them. I figured it was time to get you some. You're only going to get more horny as the weeks go on, so you'll need something to play with. Trust me, you'll thank me later.."

(Wait, did he just say weeks?? Surely that was just a mistake, right?)

"I'm sure you're going to want the real thing eventually, but I don't want to force anything on you. You'll have to ask me for that."

About that time, we pulled in to the parking lot. I had only been in a sex shop once before - kind of drunk with one of the kinkier girls I had hooked up with freshman year. We went in and she kind of just giggled as we looked over all of the dildos and vibrators. Didn't even buy anything -- I'm sure the clerk loved having drunk college kids come in just to mess around. Before we got out of the car, Connor told me I was to pick out at least 1 dildo, 1 butt plug, and lube.

I was kind of nervous to have to actually buy these things in person, wondering what the clerk would think. But once we walked in, the excitement of it all outweighed my nerves. I was actually going to have some toys of my own to play with like all of the tumblr posts I'd saved/reposted for years. 3 days in the chastity cage probably had something to do with that too.

We walked in and grabbed a basket. The female clerk welcomed us in. Honestly, she was pretty hot. Probably 2-3 years older than we were, fit, small perky tits, straight dark brown hair, wearing a tight crop top with some leggings. She was short and small - fun sized, just how I liked them. I thought I saw her give me a little wink as she asked us if we needed any help. I felt my cock twitch in the cage. She was definitely my type.

Before I could answer, Connor told her his little friend here was just looking to buy a few toys to play with. I couldn't believe he had actually said that. I felt my entire face turn as red as the thong I was wearing.

"If you've got any suggestions, I'm sure he'd love the help. This is his first time actually acting on his sissy desires in person. I'm just trying to help him out."

That's all it took for her to march over to help. "Oh, I love helping new bois with their journey. Trust me, you aren't the only one. We probably have at least one or two shy guys come in a week to buy stuff that they claim is for their girlfriends. But we see enough of them to know what they're really doing. I'm so proud of you for taking this step to really accept who you are. And you're lucky, not everyone has good friends like this to help."

I literally couldn't believe this was happening. Connor was clearly loving this, but I was mortified. Not only was another person learning my secret, but it was a super hot girl around our age. She could know other people on campus for all I knew. I guess she could tell, because she quickly threw her arms around me and gave me a hug.

"Oh, please don't be embarrassed. Your little secret is safe with me, but I really do want to help you with any questions you might have! Today or down the road -- give me your phone and I'll put my number in. My name's Jess by the way."

"Now tell me, what exactly are you looking for today?"

I expected Connor to interject again, but he just nodded to me, indicating that he wanted me to actually have to tell her.

"Well, I need to get some lube, a buttplug, and a dildo." I admitted.

"Perfect! I can definitely help you there," she said as she led us to the right side of the store. "As you can see, these are our dildos."

I didn't even know where to start. There were so many -- small, pink dildos with confetti on them all the way to 12"+ BBC dildos. She grabbed one off the wall and put it in my basket. "This one's great for beginners, but still not too small. I know bois like you have pretty greedy holes. Don't want to start too small and have to come back tomorrow."

I looked down and saw a 6.5" white dildo with balls and a suction cup. It felt fitting that my first dildo would be about the same size as my actual cock when it wasn't locked in this cage. Although, admittedly I was closer to 6" if we're being honest. What did she mean by beginner though? I'd never had any girls complain about my size before?

"Okay, next you'll need a plug, but I think you should get to pick this one."

There were tons to choose from. Training sets that came with 4 different sizes, vibrating plugs, Bluetooth plugs, and the classic metal plugs with the jewels on the end that I had seen all too many times online. I knew that's what I wanted. I loved the pink jewel accent for some reason. I grabbed one from the wall and put it in my basket.

"Yes, how cute," she exclaimed. "You really are a bit of a sissy aren't you?" Girls always gravitate toward the jewels. "I bet you're wearing panties right now aren't you?"

"Go ahead and show her. There's no one else here. I'm sure it won't be her first time seeing a locked boy in panties." Connor naturally filled the dominant role that he had assumed over the last few days.

I pulled my joggers down a bit to show her the top of my panties. But quickly realized that wasn't going to suffice. They wanted my pants all the way down. I shimmied them down my legs, revealing the tight, red thong. I thought about trying to cover my crotch, but knew better. I just held my hands close to my chest, embarrassed.

"Aaaaand you're locked already?! Omg, you're just perfect aren't you?! I'm going to be your new best friend. I love chastity cages -- I tried it with my ex, but he could barely fit in our biggest cage. And he just wasn't into it, just finally let me try it on him after I had asked so many times. I've always wanted to keep a guy locked to see how desperate he'd get to serve me."

She bent over to get a closer look. "This is the best day of work I've had in a while! You're so cute."

I felt a mix of flattered and humiliated at the same time. I didn't want her calling me cute, I wanted her naked on her knees sucking my cock. Even more, I wanted her bent over as I made her moan before filling her pussy with my cum. That wasn't really possible given my current predicament though.

"These enclosed plastic cages are so much work," she said. "Can I get you a better one? We have all kinds, but I really think the 3D printed ones are the best. They're much more breathable, light, and super easy to clean. The enclosed plastic traps so much moisture, which really can cause problems if you're wearing it for longer periods of time."

Connor seemed to like the idea. It was obvious that I did too, this thing was killing me at night and I had to constantly adjust it during the day.

"Okay, come to the back and we'll get you fitted. Don't worry, this one is on the house." I pulled my joggers back up, she grabbed my hand, and started to lead me toward the back. She looked to Connor and asked him to watch the store for a few minutes. Unfortunately, as we got to the back room, I remembered that I didn't have the key to actually unlock this one. I told Jess and she giggled as she flipped back to ask Conor for it. Could this day get any more humiliating?

Connor laughed too and tossed her the key from his key ring. Back with Jess, before she did anything else, she grabbed my shoulders, looked me straight in the eyes, and asked very seriously, "Are you okay with this? If he's forcing you to do this, I can give you this key and let you out the back. You don't have to do anything you don't want to. Trust me, I can make him regret this."

I pondered for a moment, tempted to get out of this entire situation. But as I looked at Jess in front of me, thought of the pics that Connor had, and really thought of how I'd fantasized about this for a while, I told her I did in fact want it. It was new, but I'd wanted to explore my submissive side for a while. I told her that Connor was my roommate and explained what had happened earlier when he walked in on me.

She gave me a kiss on the cheek and told me how proud she was of me. Then she told me strip down again. "This time panties too, babe," she said with a smile.

She squatted, her face now inches from my cage, as she unlocked me for the first time in 3 days. Before she could even slide the tube off, my cock sprung to life.

"Whoa there, you really do like this! I've barely even touched it yet." She pulled the tube off, but there was no way the ring would come off with how hard I was. To my surprise, she opened her mouth and licked all the way up my shaft - starting at my balls all the way to the head. She looked up at me, made eye contact and whispered, "This can be our little secret. Honestly, the thought of having a cute sissy friend has me so wet. One last blowjob might be good for you."

She proceeded to give me the best blowjob I'd ever had. I don't think I had ever been that hard before. Maybe it was from being caged for 3 days. Maybe it was because the ring of my cage was still on - kind of working as a cock ring to keep all of the blood in my cock. Maybe it was the panties around my ankles. Or maybe it was how sexy Jess was. She could deepthroat my cock with ease and knew all kinds of tricks I'd never felt a girl do before. I wish it could have lasted forever.

Sadly, after only 3 minutes or so, I could tell it'd be ending soon. She had one hand folding my balls and could feel them starting to tense up. She must have noticed too because it only seemed to encourage her more. She pulled her mouth back to just the head and continued to lick the underside of my head as she stroked my cock with one hand and played with my balls in the other.

She looked up and locked eyes with me again as I started to cum. I shot at least 7 times. She kept eye contact with me the entire time as I continued to fill her mouth with all of my cum. My orgasm finally ended (one of the best I'd ever had if we're being honest). Without missing a beat, she popped up and began to kiss me. I quickly realized she hadn't swallowed any of my load. Instead, she'd just held it there to feed back to me.

I didn't have much of a choice -- not that I would have protested anyway. I'd do anything for this girl. I had tasted my cum many times before, trying to follow the instructions on whichever sissy caption or video I was watching. It was never this much of it, though. I could usually only bring myself to try a small taste after I'd cum. The most I'd tasted was when I came upside down, with my cock aiming at my face so I couldn't wimp out (sissy hypno and JOI can make you do some crazy things).

Jess kept making out with me though, not giving me any option not to swallow all of my own cum. Honestly, I loved every bit of it. Knowing I was doing what she wanted made me so happy. She finally broke the kiss and said, "Good bois always clean up their messes." Another one of her cute little winks followed.

She squatted again to make sure she had cleaned all of the drool and cum from my cock. Went in for another kiss to give me the rest, pulled the old cage ring off, then went straight for the new cages.

I was so surprised at what had happened, still reveling in the orgasm I'd just had. And the fact that I'd eaten so much cum. It definitely had a new aftertaste I'd have to get used to. My cock shrunk back to normal size. I had a bit of post-nut clarity as she started to hold the new cages to my soft cock. I couldn't say no to such a beautiful woman, especially after the orgasm she'd just given me.

"This will be such a step up from your old cage." She really was acting like that was no big deal whatsoever, just back to business. Meanwhile, my mind was melting. I'd do anything for her. "Your old cage was kind of big for you to be honest, I bet you were having an awful time sleeping. A smaller cage will keep you from getting hard at all, which will help so much when your little cock tries to start getting hard. The right sized ring will help a lot too," as she slipped my balls and cock through the new one.

I looked down at her holding two cages to the sides of my cock -- one black, one pink -- both at least half an inch smaller than my old one. They looked tiny, there was no way I would fit.

"I think pink is the obvious choice to go with your cute panties. The black cages are more for masculine guys, pink is always the way to go if you're into sissification. I'm so excited to have a little sissy girlfriend to play with."

She slid the cage on, and I was shocked that it actually fit without much effort. She slid the key in, twisted it, and pulled it out, giving the cage a little kiss on her way. "So much better! You're just perfect! Now let's get you back to Connor before he starts getting impatient."

I put my clothes back on. Couldn't deny how much better the cage felt. It also looked a lot better in my panties -- just a little nub compared to the clanky cage bulge I had before.

Still acting like this was completely normal, she led me back to the main room of the store. She told Connor how much better it fits and that he wouldn't need to worry as much about regular unlocks to clean anymore thanks to the new model (not like he had unlocked me much to begin with, but it had only been 3 days).

"I'm sure I'll have plenty of time to see it later," he said. "Thanks for helping with that!" She handed him both of the new keys, but he quickly gave one of them back to her. "I think it'd be good to have you hold on to one of these. Safer if I'm busy and he needs to unlock for an emergency or something. And I think you'll be a good influence for him as he continues on this little journey."

"I'm honored! And I can't wait to play with -- wait I don't think I even know your name yet!"

"Ryan," I said.

"Here, give me your number too. That way I can text you if you get a little too scared to text me first."

As I did that, she grabbed two bottles of lube from the counter and started ringing all of my items up. Came out to about $80, but she put in her employee discount code, which brought it down to just over $50. I put my card in the card reader as she and Connor exchanged numbers as well.

"You two come back anytime. Just text me beforehand - as long as I'm here, I can get you the employee discount."

"Oh, trust me. We'll be back. I already saw lots of other things Ryan will be needing pretty soon. That little plug and dildo won't keep him satisfied for long."

We got back in his car and honestly, I felt bliss. Could have been the blowjob, but really I think it was that I was actually living out one something I had fantasized about for years. I had a full week's worth of panties to wear, a plug and a dildo to play with, my roommate as a keyholder, and now a dream of a girl as one too.

We got back to the house and Connor wanted to see the new cage. I wanted to show him too. I was kind of starting to long for his approval. I stripped down and presented myself as he'd taught me -- hands behind my back, head down.

He laughed. "Holy shit dude, this thing really is tiny. I think the head of my dick is bigger than that."

He pulled his cock out, which was probably half hard at this point. At least I thought so based on the size -- there's no way it could be that big soft. He was right though; the head of his dick was about the same size as my little locked nub. Maybe slightly smaller, but I'm sure it would grow more when it got 100% hard.