I had been friends with Riley for years. We’d been neighbours since we were kids and since then, I’d considered her my best friend. She grew up to be the hot girl everyone wanted to be with, while I was a bit more secluded and introverted.
Riley was still my friend, and that made everyone jealous. They envied me for having one of the hottest girls in town as my friend. She was pretty short at 5’5, with lucious brown hair winding down to her lower back, and emerald eyes that sparkled in the sun.
Yep, I could definitely see why everyone wanted her. She was part of my fantasies for a while. In the end, I saw her as a friend. To be honest, she was my only friend.
I always dreaded the day of us getting our college admission letters. I felt it would be a case of us breaking up our friendship or at least, not seeing each other as often. But as luck would have it, we ended up enrolled in the same college.
Riley even came up with the idea of becoming roommates. She trusted me and she didn’t have any girlfriends joining us over there. I said yes, not just because I would share an apartment with a stunning woman. I agreed because we were comfortable with each other.
The first couple of weeks were great. We began to experience college life together.
At first, there was some awkwardness. However, we reached a point where she felt comfortable running around in her underwear when we were alone.
I didn't wear tight pants because I wanted to hide my feelings around her. Inside, I wished she would take a risk. I hoped she would remove her underwear and come to me. But fate had something different in store for me.
About a month in, Riley approached me with a question.
“Hey so you have a minute?” she asked me while I was lying on my bed playing with my phone.
I noticed there was concern in her eyes and immediately motioned for her to sit with me. “What’s up Riley? Something happen?”
“Oh no, nothing like that,” she said with a quick smile. “I met this guy in one of my classes. I was wondering if it would be okay with you if I invited him over.”
She bit her lip while looking me in the eyes.
I laughed. “Oh course it’s ok,” I said with a smile, “I’m not getting in the way of your dating life. Let me know the date, and I’ll make sure to stay in my room that night to give you guys privacy. That ok?”
She hopped onto her knees and gave me a long hug.
“Yes that’s perfect! Thank you for being so understanding!”
Two weeks later, I sat in my room playing a video game on my laptop. Riley was talking to a guy in the shared space. I’d been in my room before he even arrived so I decided to just stay in and not bother them.
I felt a twinge of jealousy knowing this guy had a chance with her. I quickly let it go and decided to call it a night.
A few hours later, I woke up to moaning sounds. I quickly realized my childhood best friend was having sex across the hall. And she was loud!
I tried to get back to sleep but everything was too distracting. Eventually, I felt my hand creep into my pants and grasp my cock.
I took a deep breath and started stroking. I focused on her moans and imagined her on top of me, riding me like it was her last night on earth.
It didn’t take me long to cum but I muffled my groans to make sure they didn’t hear me. That was enough to put me back to sleep.
The morning after was awkward to say the least. I was the first one up and was fixing myself some coffee when they emerged.
“Hey! Good morning,” said Riley with a smile.
I nodded and approached them, extending my hand towards her, I would now assume, boyfriend.
“Hey, I’m Connor, Riley’s roommate,” I said, “Pleased to meet you.”
“I’m Ben,” he said, taking my hand in a strong shake, “Riley didn’t mention she had a male roommate.”
He glared at me as Riley fumbled a bit.
“Well it never came up. Hope that doesn’t make you uncomfortable.”
There was concern in her voice and I could tell she liked the guy. I was feeling guilty but staying in my room until he left wasn’t an option. He’d have had to meet me at some point.
There was a lot of tension in the air until they both eventually left for class. I waited a while and texted her:
“Is everything ok? Ben gave me the impression I was causing problems :/”
“No it’s fine :) I’ll talk to him. I’m sure he’ll understand once he learns about how long we’ve known each other!”
Part of me wanted everything to work out for her, but another part wanted them to break up, and hope that she would see me in a new light. While they didn’t break up, a new light did start to dawn on me in her eyes.
Riley had late classes that day so by the time she came home, dinner was on the table and I was just about to start eating.
She came into the apartment looking confused. I immediately got up and approached her with concern.
“Hey, you look down. What happened?”
“I’m not sure,” she said, her voice shaky. “I thought we had fun yesterday, but he kept ignoring me today after we left.”
I took her to the couch and sat her down.
“It’s about me isn’t it?” I asked.
"Well, yeah," she said with a sigh. "He doesn’t like that I have a male roommate. Even though we’ve been friends for years, he doesn’t trust that nothing will happen between us under the same roof."
“Oh come on! That’s crazy! Want me to talk to him?”
“Well, there’s no need, because he did suggest something, but I told him it would be going too far.”
“What did he suggest then? If there’s anything that would make him more comfortable, short of me moving out, I’m all for it!”
She looked at me and I saw a determination in her eyes.
“Well, this is gonna sound really weird, but he suggested that while you and I live together, that you wear a chastity cage. That way he’d know that nothing is happening between us. At least, until he gets to know you better.”
“Wait a chastity cage? I don’t know Riley. We’ve never even seen each other naked. It would feel weird.”
“I know but I’ll try to make you as comfortable as possible. If it helps, I’ll start having him over everyday and we can hang out together. He’ll see he has nothing to worry about.”
“I mean we can try, but something feels off to me. You sure you’re ok with this?”
“I am if you are. He’s a great guy and I really like him.”
Well I guess ok then. Where do we begin?
She grabbed her bag and started rummaging. It was then that she brought out the cage to show me. “I kind of bought one. I’m sorry if this is weird.”
“That’s ok,” I said, stifling a moan. I had a massive boner now and I realised the whole idea was turning me on.
“So you wanna give it to me so I can put it on in the bathroom?”
“Why don’t you put it on in front of me? I’ll help you.”
“I’d have to get naked to do it though,” I said, worried that this would impact our friendship.
“Hey don’t worry, it’s just me. I promise this is only temporary and nothing will change between us.”
I decided to go through with it. My reasoning was that it would make her happy, but in hindsight, I should have asked more questions before committing.
The cage itself was made up of small bars. This made sure I would be able to clean myself without actually needing to take it off. I started undressing awkwardly, while Riley started rubbing my arm, comforting me.
I was eventually down to just my boxers and Riley helped me stand. Falling to her knees, she started taking them off until my cock popped free and hit her on the nose.
She started laughing and despite the circumstances, I laughed too. It was a calm moment in that moment of tension. My cokc was erect and my best friend was mere inches from it.
“I’m not gonna be able to get this cage on you with your cock like that,” she said with a smile, “Is that why you wanted to go to the bathroom?”
“Kind of yeah,” I stammered, feeling shy.
“Well we can’t have that! Which means there’s only one thing to do in this case!”
With that, she lunged forward and my cock was suddenly in her mouth. I felt her tongue jumping around licking the base of my shaft all the way to the head.
I could barely process what was happening. She bobbed her head up and down at a rhythmic pace while I fought to stay on my feet. As I felt my orgasm coming, I tapped her shoulder to warn her, and at that she simply looked up and winked.
I came down her throat and collapsed onto the floor, unable to take the sudden rush of excitement of the situation. While I tried to recover from the experience, I felt Riley lock the cage on. Suddenly there was a CLICK sound, and just like that my fate was sealed.
I looked at the cage encasing my limp dick and then at my smiling bff. She was wiping her mouth with a tissue.
“Well someone had a lot of pent up frustration,” she joked.
“It’s not everyday your best friend goes down on you,” I retorted with a smile.
“You owe me one, but make sure this stays between us. No need for Ben to know what just happened. As far as he’s concerned, I gave you the cage and you put it on.”
“Got it!” I said with a nod.
“Ok then goodnight!” she said, giving me a hug.
I slept fitfully that night. It didn’t take long for my cock to try and get hard again, but the cage stopped it. The padlock was pretty strong so breaking it without power tools was definitely not an option. Peeing was already a challenge and I had to sit down to do it without making a mess.
In bed, my mind kept drifting to that glorious blowjob I’d just received, with Riley swallowing my load over and over again. Needless to say, being unable to touch myself was frustrating and I was already regretting it.
Riley left early the morning after and I didn’t get a chance to talk to her. As the day went by, I was reminded of the cage almost constantly, and I couldn’t get her out of my mind. I was also really self-concious about it, and felt like everyone knew that I was wearing it.
When I got home, Riley still wasn’t there, which was strange since her classes ended early that day. I decided to text her.
“Hey everything ok? Expected to find you at the apartment.”
“Yeah sorry forgot to mention I’m sleeping at Ben’s tonight.”
“As long as you’re fine :) Hope everything worked out.”
“Oh yeah, it worked out! Thanks for doing this, I really appreciate it! Hope it’s not too hard on you”
“I’ll manage. Lemme know when we can all hang out! :)”
“Will do!”
I didn’t hear from her the rest of the night. I experimented with trying to take the cage off, even trying to pick the lock but to no avail. Eventually I settled down for another fitful sleep.
The morning after, I awoke to my cock throbbing painfully in the cage. Again I tried to no avail to jimmy the padlock open, but it was relentless. Sighing to myself and wondering what I had exactly gotten myself into, I decided to settle on some coffee.
Again Riley was not here. She must have stayed at Ben’s for the night. Ironic how he needed me locked in a cage to make sure he can have sex with my best friend.
I avoided people throughout the day, especially other girls. The pain was growing intense and I was honestly getting worried that something was wrong. I was thinking of texting Riley but decided not to bother her. I only hoped she would be home that evening.
My wishes were answered. I walked into the kitchen after a full day of classes, and saw something that made my jaw drop.
Riley was sitting back on a chair wearing a sheer robe. It was open down the middle, and Riley wore absolutely nothing else. For the first time, I could see her nipples and breasts peeking out of the open robe and a small mound of hair hidden behind her crossed legs.
She smiled a devilish grin.
“Welcome home!”
“Riley, what’s going on?” I stammered, my breathing heavy.
“I haven’t been home in two days and I know you’re suffering because of the cage, so I thought I’d give you a treat.”
“Seriously? But what about our friendship? As hot as you are I really don’t want to risk it.”
“Oh we’ll be fine hun don’t you worry.”
“God Riley, this thing has been killing me. I’ve been in pain all day. I can’t wait to take it off.”
“Take if off? Sorry, but that’s not the plan for tonight. I couldn’t even if I wanted to.”
“What do you mean?” I asked, my voice getting a bit whiney, “Can’t you just grab the key and leave me unlocked? Ben wouldn’t know.”
“That’s the thing. I don’t have your key. Ben’s keeping it so I don’t get tempted.”
“Wait, so what happens now? When am I getting unlocked?”
“Don’t worry about that for now. It will happen I’m sure. For now though, I need you to return a special favour.”
And with that she opened her legs and I was staring at her gorgeous pussy for the first time. Not sure what came over me, I decided to go for it. Falling to my knees I buried my face and started licking.
She screamed over and over as orgasm after orgasm rocked her. I never knew I was this good at licking pussy. It took her 5 orgasms before she pulled my face away. I was absolutely drenched in her juices and I revelled in the glow of her face as she sighed and leaned back.
“Damn, that’s one way to repay a favour! That was amazing!” she said.
“Riley, I'm in a lot of pain,” I said, my eyes tearing up a bit, “Is there no way to take this off? Please?”
“I’m really sorry,” she said, quickly dropping down next to me and hugging me, “there really is no way out without the keys. I can’t ask Ben, that’s not the agreement.”
Then she looked at me and it was like an idea popped into her head.
“Wait, I think I know what the problem is. You’re in pain because you haven’t cum in 2 days, right? I mean, your balls are a shade of blue.”
“How’s that revelation going to help? I can’t cum with this on.”
“Actually, you can!” With that, she jumped onto her feet and rushed into her room. I just sat there on the floor, dazed and confused.
After some time, I heard her calling for me and I slowly made my way to her room. I was greeted by Riley, standing next to her bed, with a strapon around her waist.
“Wait what?” I asked dumfounded.
“This is the solution. If I can fuck you just right, you’ll have a prostate orgasm. I’ve read a lot about it and it is definitely doable.”
I couldn’t believe what I was hearing or even seeing. My mind screamed at me to just refuse and just wait for the actual unlocking. But my cock told me otherwise. I was soon on my hands and knees on her bed, my ass getting lubed.
She thrust into me slowly at first, and then starting slowly fucking me. The experience was unlike anything I experienced before. She rode me like a bull, and soon she was slapping my ass and playing with my balls.
Then it happened. I felt a jolt of electricity running through me and then I felt my cum dribble out through the cage. Riley finally stopped pegging me and looked down, happy and satisfied.
“That should do it! See, I told you it would work. Now we don’t need to worry about unlocking you.”
I had no strength to argue back, despite the bad feeling I was getting in my stomach. I spent the night cuddled up with Riley, her ass wiggling against the cage for the entire night.
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