Frat Boy Turned - A Day with Jess

I woke up the next morning as Connor walked back in our room from his morning shower. I couldn't believe how well I had slept! I guess Jess really was right that I just needed a smaller cage.

I didn't have much time to think about my new cage because my mind was immediately taken elsewhere when Connor dropped his towel to get dressed. Damn, his cock was perfect.

"Like what you see?" Connor asked with a grin. "I figured I don't need to worry about covering up anymore around you. I've seen yours, so you might as well get to see mine."

Seeing Connor completely naked for the first time immediately turned me on. Not only was his cock mesmerizing, but he also had an amazing body. Connor was fit, strong, six-pack abs -- the whole package. How had I never noticed this before? I think being caged was already changing the way I thought, and it had only been 4 days! Damn, I'm in trouble.

I looked at the time and realized I slept a lot later than I intended. I needed to shower fast. I hopped out of bed and saw myself in the mirror -- all I had on was the red thong from yesterday. I really was high last night.

Connor saw too, "Fuck, Ry. I cant't lie - you really do have a girl's ass." He grabbed my butt and I felt my cage twitch. Still looking in the mirror, I could see his cock had sprung to about half mast. "After your day with Jess, you might be able to pull off the whole look."

He saw the look in my eyes and could tell I was surprised. "Yeah, Jess already told me you two have plans today. She's pretty excited to help turn you into a total sissy. Honestly, I'm excited too. Can't wait to see what all she has in mind. I'll just get to reap the benefits".

He pulled his boxers on; his cock making a pretty obvious tent in the front. Something mine could no longer do. "You better run to the shower, don't wanna be late to class. Send me a pic of whichever panties you choose today before you leave though."

"Shit," I thought. "Please let one of the private shower stalls be open." I knew I'd just have to skip a shower altogether if they were taken. I couldn't bring myself to risk it in the community shower. Luckily there was only one other guy in the bathroom and he was already showering. I hung my towel on the hook and hopped in the other stall. I was nervous, but everyone was in a hurry to try to make it to class on time so I figured no one else would come in.

Luckily, I was right. I finished showering and scurried back to the room to get dressed. I picked the light blue striped cheeky panties and pulled them over my butt in front of the mirror. Connor was right, I did kind of have a girly butt. The panties accentuated that. I snapped a pic, sent it to Connor, and then was on my way.

Class was uneventful. I had marketing and economics that morning. I usually went to the cafeteria after, but since I knew I needed to be on time to Jess's, I just grabbed a snack to go from the student center.

I threw my new toys in a bag with the rest of my panties, just in case Jess wanted to see what all I had. The address Jess gave me was about 20 minutes away, so I hopped in my car to head out.

I was so excited to see her again, although was not getting my hopes up for another blowjob. I pulled into the driveway of her house -- which was impressive for someone our age. How did she pay for this?? I learned later on that her dad was pretty wealthy and bought her the house after her mom had died. He was pretty aloof and lived in New York for business, so she had the whole place to herself.

I rang the doorbell and saw her turn the corner into the foyer. She was wearing a super soft looking pink robe.

She opened the door and welcomed me in. Before I could say anything though, she instructed me to get out of my boy clothes. "No need for those here. It's just us girls around!" I handed her my bag and stripped down. She took my clothes and threw them in the corner.

"I love the panties, Ry. They're cute -- no need to try to go for the slutty route every day." She led me to one of the bathrooms and grabbed another robe off the hook. "Don't want you getting too cold! We'll have you in the shower in no time. First I just want to talk though. Tell me all about how you got to this point -- don't spare any details."

She grabbed us two glasses of white wine and I told her about my whole journey -- starting back when my sisters played dress up with me, to finding CFNM porn, my tumblr, my progression to chastity porn, sissy porn and hypnosis, all the way to seeing Connor's cock this morning.

Jess told me more about her too. She told me about her dad and the house (put me at ease knowing no one else lived here). She had gone to art school, but quickly learned that wasn't going to help her make it as an artist. She was naturally gifted and told me that all of the art in the house was actually hers. Instead of wasting time in class, she opted to spend it honing her craft. Not like she had to worry about money anyway.

The job at the sex shop? Just what she liked to do in her spare time. She told me she'd always had a huge sex drive -- and that she was pretty kinky herself. She loved men and seeing them melt under her control, but she'd never found anyone that really let her indulge in all of her kinks. With a body like hers, she typically attracted the alpha-jock type.

After learning about each other, she told me more of what she wanted our relationship to look like. "I know you're still in school, so this can't be a full time thing. But that doesn't mean it can't be a total transformation when it is one. You've obviously flirted with this idea for a while, and I can't wait to help you explore your sissy side. From now on, when you're with me, you're Riley - not Ryan."

"Honestly, you're a lot further in than I first thought. With all the sissy hypno you've watched over the years, there's definitely some underlying triggers in your brain already. That explains why you've been so mesmerized by Connor's dick. I'm not sure which ones you've watched, but a lot of them train your brain to immediately slip into girl mode when you see a big cock. You'll associate big cocks with your horniness - and we both know you don't really have one yourself anymore, so the chastity will push you further and further down that rabbit hole."

I was scared to admit how much I had watched, but knew she was right. Who knows what else was already embedded in my mind.

We had finished the full bottle of wine over our discussion. I was definitely feeling more comfortable, other than my cock straining in the cage from all of the talk.

"Now that we're both on the same page -- let's get to the fun stuff!"

She stood up and led me toward the master bedroom. It was beautiful. Exactly what you'd expect from Jess. She slid her robe off her shoulder and tossed it on the bed, revealing the full set of white lingerie she had on underneath.

"Gosh, I wish I looked like that." I caught myself thinking. She spun around, slid my robe off and tossed it on the bed too. Then she bent over and shimmied my panties down my legs too.

"Omg, that cage truly is perfect for you. It's so cute." She gave it a quick kiss and then grabbed my hand to take me into the bathroom.

She bent at the waist again to turn the bath on (I swear she was doing that on purpose to tease me, because she was by far the sexiest girl I had ever been around). She then grabbed some Nair from under the sink and handed it to me.

I knew what to do. Honestly, I had fantasized about what it'd feel like to be completely hairless many times before. I wasn't super hairy to begin with, but there's still a big difference in being 100% smooth. I spread the Nair across all of my body from the neck down. Jess made sure I got between my legs and my butt, too.

After a few minutes, I could feel it all tingling and slid into the bath. She handed me a loofa and then some girly soap as she poured in some bubble bath.

"It's best to soak to really get soft, smooth skin like mine. You stay here for a bit, I'll go get you a towel and some fresh panties." When she came back, I could tell it wasn't any of the panties that I had brought over. Instead, it was a matching set that she had on - just pink instead.

After I dried off, she showed me how to get into the lingerie. This was my first time dealing with real lingerie. She told me to put the garters on first, then the lacy panties. Then she had me turn around as she clipped the bra on me.

"You're not allowed to look in the mirror yet," she said. "Not until I do your makeup. I want you to wait to see the finished product."

She sat me in her makeup chair, but spun it around to face the bath instead of the mirror while she worked on my face for the next thirty minutes. Then she went back to the bedroom and came back with a brown wig. She got it fitted on my head and gave me a huge kiss.

"Omg, you're just perfect, Riley. Now you're ready to see for yourself."

She walked me back to the bedroom to the full body mirror she had. Honestly, I couldn't believe my eyes. I never thought I could look this feminine. If it weren't for the outline of my cage through the lace panties, no one would know I wasn't a real girl. I was still a bit taller and bigger, but I was pretty thin for my height. We could be taken as sisters. Her boobs filled out her bra better than mine, obviously. But there were plenty of flat chested girls out there. A horny college guy wouldn't care at all as long as he was getting his rocks off.

"Now that I've shown you how great it feels to look like a girl, now I want to show you how great it feels to play like one."

She opened the top drawer of her dresser and revealed a myriad of sex toys. She had everything you could think of -- perks of working at the sex shop I guess.

"Don't worry, we'll ease you into all of these. For now, I want you to find your g spot."

I was a little confused, knowing guys didn't have g spots, but had a feeling I knew what she meant.

"Once you feel what it's like to get your prostate stimulated, you'll never want to go back to stroking your cock again. Not that you really have that option anyway. We'll ease you into the dildos later," she said as she giggled.

She grabbed a prostate massager that looked oddly like a penis head on the end and a bottle of lube.

"Okay, come with me and I'll show you your room."

I had my own room here?! I guess since she had the whole house to herself, there was no need to share a room while I was there -- even if I wanted to. We walked down across the hall into a room even girlier than her own. Her room had an elegant, feminine vibe. This one was 100% slutty teenage girl. Baby blue walls, a pink bedspread with plush, fuzzy pillows, a closet full of short skirts, tight dresses, onesies, body suits, etc. The walls were full of posters of ripped, hunky guys. And there was a massive tv across from the bed that had to be at least 80 inches.

"This is where you'll sleep when you stay over! You can change whatever you want in here, but I doubt you'll want to. I think it suits Riley well," she said with a wink.

Honestly I wanted to see what all was in the dresser after seeing all the clothes hanging in the closet. But that was for another time. She told me take my panties off, lay on the bed, but to lay on my stomach facing the tv.

I did as I was told, like an eager slut. Now I understood why she had me out my panties on after the garter and stockings. She turned the tv on to a 2 hour video. Then climbed behind me on the bed.

"You just settle in, I'll handle everything. All I want you to do is to watch the tv and enjoy the ride."

I then felt something cold on my hole, which I quickly realized was lube. She shot a little into my hole with a syringe and then used her finger to spread the rest. She even slipped it in a few times, which I secretly loved.

It wasn't long until I was completely entranced by the tv. This was a new sissy hypno that I hadn't seen before -- much less any this long. I usually gave in and jerked off after thirty minutes or so. It started with a girl that looked a lot like me as she was getting dressed. Her man entered pretty quickly and all I could notice was how insanely big his bulge was in his boxer briefs. Thankfully I didn't have to wait long to see it as she dropped to her knees and slid his underwear down, his cock hitting her in the face as it sprang free.

I felt more pressure on my hole and realized Jess was sliding the vibrator in. I could feel my hole stretch around it and soon it slid all the way into place. Honestly, I loved how full it made me feel. I was too busy watching the tv though to have much of a reaction. That is until Jess turned the vibration on. I let out an involuntary moan and heard her giggle behind me.

"I told you you'd love this. I've got some other things to take care of now, so I'll leave you to it. I have the vibrator set to match the action on the tv, so I'm sure you'll be leaking pretty soon. Enjoy it baby, this is just a taste of how good it feels to be a girl."

She turned the light off on her way out, which only made me focus more at the massive tv in front of me.

With the vibrator matching the hypno, I really started to feel like I was the girl on the tv. As she started getting fucked, I felt the vibrator pulse with every thrust. Gosh, it was amazing. So amazing that I didn't realize the door had opened again.

I didn't notice anyone had come back in the room until they walked in front of my eyesight to the tv. But then I quickly realized it wasn't just Jess. She had a guy with her. As I came to, I saw it was Connor.

"Wow, you really did a number on him. I never thought Ryan would turn this fast -- or even look this good honestly."

Jess cut him off, "This isn't Ryan, from now on when she's dressed -- or even when it's just the three of us -- this is Riley."

"Oooh I like that. Well, Riley, you look stunning. Turning me on already and I just got here."

I could see the outline of his cock through his sweatpants and all I could think about was how badly I wanted it in my mouth.

"Can I please suck your cock, sir?" I suddenly heard myself ask.

Connor and Jess both looked a little surprised. "Holy shit, what all did you do him?" asked Connor.

"I didn't do anything other than encourage the real Riley to come out. She's already watched a ton of sissy hypno the last few years, so I guess all she needed was a little push to really be her real self. Honestly, I didn't think she'd be asking for cock this fast, but that's what you wanted so why deprive her of it?"

They were talking about me like I wasn't right in front of them, but I didn't care. All I wanted was Connor's cock in my mouth. I also noticed Jess was referring me with she/her pronouns now, but I didn't care about that either. This whole day really had fucked with my head.

"You're right," said Conner, "might as well give the slut what she wants." He pulled his sweatpants off to reveal he wasn't wearing any underwear.

There it was, my roommate's half hard cock just inches away from my mouth. Was I really going to do this? Would this make me gay? I didn't care at all. With the vibrator pulsing against my prostate, my cock straining in its cage, and my melted brain, all I wanted was his cock.

He took another step toward the end of the bed as I slid toward him and felt his cock swing into my cheek. I eagerly opened my mouth and took the head of his cock in. I was surprised how wide I really had to open to fit my lips around it. I guess I'd never thought about it actually being a challenge in that sense. Luckily I'd watched enough porn to know exactly what to do to get him fully hard.

Just as Jess did to me the day before, I made sure to lick from his balls all the way up his shaft before I'd spend some time just licking the head.

"Fuck, she really is a natural," he said to Jess. I glanced over and saw that she had pulled one of the pink chairs over to get a front row seat to the show. She had also pulled her skirt up so she could play with herself as she watched.

It didn't take long for Connor to take control as he flipped me over on my back so my head could hang off the edge of the bed. He leaned over me and flicked my cage a few times laughing at how much I was leaking. "She even gets wet like a girl too," he exclaimed.

All I could see was the underside of his huge cock. His balls were right at my forehead and his cock easily extended past my chin. Honestly just the head of his cock was about the size of my locked clit. It was humiliating, but turned me on so much. I eagerly tried to slip his cock back in my mouth.

"This bitch really wants it bad," he said, still talking about me like I wasn't even there. "Let's see if she can deepthroat too."

I felt him position my head against the side of the bed to really give himself a good angle to use me like a toy. Then felt him slide his cock into my throat. He maybe got 4 inches in before I started gagging, but that only spurred him on.

"If you're going to dress like a slut, you better get used to being treated like one," he said, addressing me for the first time. Then he continued fucking my face.

I was gagging, drooling everywhere, and crying too from the brutal facefucking I was receiving. Yet, still felt an overwhelming sense of pride as I felt his balls finally start slapping against my face as he long stroked me.

"You've got some training to do to really master this, but don't worry -- we've got plenty of time. And we're roommates. I'd gladly offer my cock for you to practice on anytime you want. Or anytime I need to blow a load, I'm the one making the decisions here," he said with a grin.

Jess chimed in, "I love that she can't even deny that she loves this too. Her little clitty tells it all based on how much precum it's leaking."

After a few minutes of this, I could tell that he was getting close. I couldn't wait to swallow his cum. Unfortunately, he pulled out and shot all over me instead. I watched his balls twitch as I felt shot after shot land on my lingerie all the way down to my cage. I was so disappointed I didn't get to taste his cum. And disappointed that my new set of lingerie was covered in it now too.

"Fuck, that was good," I heard him say. "You can scoop up what you can if you really want to eat it. I just couldn't resist cumming all over your cute little outfit here. Trust me, you'll have plenty more chances to take my load."

Connor put his cock back in my mouth for me to clean it off, slapped it against my cheeks a few more times, then put his sweatpants back on.

"Jess, I'm impressed. I never expected he'd be sucking my cock this soon. It hasn't even been a week and he -- oh, I guess I should say she -- is already acting like a desperate cock slut. And a super hot one at that."

"You should probably just stay here tonight, Riley. I've got a date and am planning to get some real pussy tonight. But I'll see you tomorrow -- we've got the party at the house Friday night and then tailgating all day Saturday. I don't expect you to dress for that -- your secret is still safe with me. But you better wear panties and a plug. You need to start training your hole if you want to take a real dick."

With that, he headed out. He left me lying there covered in cum. And I mean covered. He came so much. I looked to Jess hoping she'd give me a towel or something to clean up with, but instead she told me I better not waste any of it. I knew what that meant, so I started trying to scoop up as much as I could on my fingers as I licked them off to get as much of it as I could. After I finally got enough of it to stand up without it all running onto the bed, I got up to head to the bathroom.

That's when I saw the stream of precum coming from my cage. He wasn't lying, I really was wet just like a girl would be. I kind of felt proud.