Learning The Chastity Ropes Pt 03

I woke up the next morning expecting to feel ashamed after sharing how submissive I really wanted to be to my wife and our bull. I woke up and actually felt refreshed. I made my wife breakfast. I couldn't stop smiling. I felt like a weight had been lifted off of my shoulders.

There was always the nagging thoughts of "What if she doesn't deliver on this? What if it's too much for her? What if I can't handle this in reality," but I didn't care. I was focused on loving the amazing communication between my wife and I.

This was years ago so I'm trying to remember the exact timeline. I think it was even before I'd made breakfast I reached out to Jason and asked if he could spend the day with us. He had plans in the morning but would be other right after lunch. I was so excited to be their bitch. And yes, I know how crazy that sounds.

My wife and I had a pretty mundane morning and I pampered her some. She was excited Jason was coming over again. Her sexual stamina is insane. That hasn't changed one bit.

With Ashley and I not talking much about anything during the morning I wondered if she felt weird about what I'd said. It sure didn't feel like it the night before. It was like she was reading my mind and she put her book down and said, "We're doing some shit tonight. As in we're going out and Jason has somethings he wants to try."

She was smiling at me and her eyes lingered before going back to the book.

"I'll try anything once," I said. That'd been my sex mantra for years.

"I think you'll do what you're told," she shot back without looking up.

Jason got there around 11, a little earlier than expected. He was wearing a skin tight t-shirt and khaki shorts. Ashley was wearing a skin tight, short blue skirt with a pink thong and a white spaghetti strap shirt that showed some nice cleavage and left a few inches between the shirt and her skirt.

While she was grabbing her back Jason walked up to me and said where she couldn't hear, "She wants to make you regret everything you said last night."

He smiled and slapped me on the back.

"You're driving, CUCK," Ashley emphasized as she and Jason got in the back seat. She then told me where we were going, which was a beachfront bar a good 45 minutes from the house. I assumed that was due to wanting some anonymity.

I put it in the GPS and got us going. I immediately heard them making out. I couldn't see much in the mirror but could tell it was a hot makeout session.

I heard a zipper then a "Hey bro," from Jason. "Tilt the mirror down for a second."

I tilted it down to see my wife pulling his cock out and sucking on it as he smirked at me. I strained incredibly hard immediately.

"Don't wreck," he said with a smirk. He came in her mouth and I didn't wreck, so everyone was happy.

We all chatted after that about things. They were being vague but said they had some things to try out on me that should make me very happy. I was nervous but more excited than anything.

When we pulled into the parking lot I got a tap on the shoulder from my wife who handed me a pink thong. I realized quickly this was her pink thong and it was soaked because shed been turned on for the entire drive.

"Take yours off, put these on." I didn't know if I was ready for this but then realized I was straining. They made jokes about people seeing me changing while I put it on in the front seat.

It was was tight but it was working. She looked at it cradling my cage and started cackling. I put my shorts back on over them and we walked inside. I felt so damn exposed, like I had nothing on. As I walked up to the attractive hostess I remember thinking "If only she knew."

We were sat at a high top right near the sand where there were some guys playing cornhole. Our waitress was a college-aged girl with blonde hair and was pretty cute. Her name was Britt.

What I vividly remember when she walked up was how she was obviously trying to figure out the dynamic of the table with me sitting across from my wife and Jason scooted over close to her. Ashley was holding onto his arm.

Britt introduced herself and Ashley did the talking. She then asked Jason, "What would you like to drink, babe?" He got a beer. She continued, "I'll take a margarita... and he'll have a water. He's our DD."

I felt about two feet tall because it was pretty obvious what was happening. Britt smiled and looked at me as she walked away. Ash looked at me and I could tell she was proud of herself. I didn't say anything but I had enjoyed that.

"She thinks you're hot," Ashley said, looking at me, "you see the smile she gave you?"

"She smiled at me because its quite evident that I'm a sidelined husband out with his wife and her lover," I said, dismissing the possibility she was attracted to me.

Jason said we should play cornhole and I said I was good just hanging at the table for a bit but they should go. They hopped up and said they'd love for me to join whenever I wanted.

A few minutes went by and they were playing a game against a couple of bros. I vividly remember how hot she looked out there and I felt myself year to take her body. I was snapped out of it when Britt walked back up with our drinks.

"A margarita for the lady, a beer for... the gentleman, and a water for you." She sat my water down right in front of me and turned to look at me.

"So, that's your wife and.. he's what? Her boyfriend?" she asked.

"More or less" I replied. My mouth suddenly feeling very dry.

"I can't get one guy and she finds two hot guys. Life isn't fair." she chuckled.

"Yeah, its a complicated situation but she seems very happy," I said, kinda hoping that'd end the conversation.

"Well, good on you, man." Britt playfully hit me on the shoulder. "You're giving your wife what she wants and have made her crazy happy. It's sweet."

I had visions of my wife getting railed by Jason and internally laughed at the thought of it being "sweet." The guy plows her while she taunts me but I guess Britt didn't know that.

"I don't know if sweet is the right word," I said. "I'm just a different kind of dude I guess."

"You got an incredibly hot woman to marry you, you must he an alright 'dude'."

I don't remember what I was thinking at this moment to blurt this out but I was staring at my wife and said, "A hot woman that I don't fuck anymore."

Britt's eyebrows went up as she searched for the right words.

"Not sure what to tell you there, man." she laughed and put her hand on my thigh for a second as she walked away.

I sat there for a second wondering why the hell I'd just outed myself like that.

Jason and Ashley came back to the table and I was a little shaken still. Ash knows me well and asked what was wrong. I told them what happened and they both laughed pretty hard.

Britt came back and took our order, again, my wife ordered for me. She definitely did it just to watch me squirm. I just knew Ash was going to say something to her about what I'd said but she didn't.

Ash got up to go to the bathroom and when she got back she told us Britt had stopped her and just said, "You are my hero, by the way." Ash stopped and asked why and she said, "Bagging two hot guys like that. But you're gorgeous so it makes sense."

Ash laughed with her and shot back, "You can borrow the one on the right, he's not doing anything with his dick anytime soon though."

So there it was. Completely outed to the attractive waitress.

Britt gave us more attention than we needed. I think she was fascinated.

Ash called her over and she asked how she didn't have a boyfriend since she was so cute, etc.

Ashley was playing with the key necklace right in front of her, pretty obviously wanting her to ask about it. She finally did.

"What is that key for?"

"I'm still getting used to wearing it. It's the reason he's not using his dick for anything anytime soon."

Britt looked over at me.

Ash continued and she started blushing and laughing while she spat out, "He's in a chastity cage."

From her reaction Britt had heard about them or was able to surmise what it was.

"Oh my god." Britt covered her mouth, "You are a different kind of dude."

Ash and Jason laughed.

"So you just, don't cum?" she said quietly.

"Not until I say he does," Ash answered for me.

"Holy shit, I'd go insane," Britt said quickly. Ash was very much in agreement with that.

They talked for a few minutes about it and she then show Britt a picture of it.

"Why is it so hot?" she said, looking at the picture. She chuckled and was blushing.

She finally walked away a little later. Our food came and the other girl who brought it out also looked at me with a grin. I knew they'd been talking.

Britt came back and asked a few more questions. How long had it been? Did Jason wear one? (That was met with a huge laugh from both of them)

Ash said, "No, he fucks my brains out. Right in front of that one," she said taunting me as she pointed. It's worth noting she was a couple of margaritas in by this point.

"Fuck I need to stop asking questions about this while I'm at work. This is so hot." She and Ashley shared phone numbers. They were really hitting it off. It turned out she lived in an apartment about twenty minutes towards our place.

We ate and they drank some more. They ended up making out at the table and Britt took that moment to walk up to the table and drop off the check.

Where it usually said, "Thanks for coming! :)" or whatever it instead said, "Enjoy the blue balls! :("

I chuckled but Ashley almost died laughing when I showed her. When Britt came back she got up and gave her a hug. "I love you already," she said in a very tipsy voice, "fucking tip her big," she said to me. I did.

While I drove us back to the house they couldn't keep their hands off of each other. Neither one had their seatbelts on and Jason had somehow found a position where he could eat her out and I was leaking into the thong as I listened to her screams and thought about Britt.

Her body was so sexy. I hadn't been ogling her but of course I couldn't help but notice. It turned me on knowing that another hot girl knew I was a caged cuck. I figured Ash would think the night was a success in taking a dive into the humiliation side of things.

When we got back to the house they were still all over each other when we got back to the house. They barely made it through the door they were making out so much.

They were going to the bedroom and I followed when Ash said, "WAIT!" We all stopped.

She looked at me as she backed onto the bed, "Take your pants off, slut." she was still tipsy. I took them off and the front of the thong eas soaked with my precum.

Ash and Jason took in the sight of me and she made me take my shirt off. There I was in just my cage and her pink thong digging into my sides.

"Owwwww" she said laughing, "spin around for us!" I turned around, insanely humiliated.

"To steal a phrase from my new bestie, 'Why is it so hot!?'" Jason was smiling but I could tell he was wanting to fuck her so badly.

Ash called me forward and we were super close with her hand on my face.

"Now go sit in the chair and watch how a man who doesn't wear a cage takes care of your wife." She kissed me aggressively then pushed me away playfully.

Jason was naked before I knew it and the next 15 minutes was the most intense sex I'd ever seen to that point in my life. Ash was as turned on as I'd ever seen her. He started slamming her missionary then stopped halfway through and made her suck him.

After that he spun her around and had her facing me doggy-style. She had her head down and he grabbed her by the hair while he was pounding her.

He pulled her head up by her hair and said, "Look in his fucking eyes." She and I were staring at each other and my balls were sizzling to the point I didn't know if I could take it. I started squirming. I wanted to jack off and just cum everywhere.

She saw this in my eyes and her mouth was hanging open as she got pounded. She tried to smile at me a couple of times but was in a trance.

"How are you liking those blue balls?" she gasped out.

I was feeling desperate and I said, "They're so sore baby..."

"Good!" she managed a smile. "Enjoy the blue balls... because we are never going back."

I felt my balls tighten. For the first time since I put on the cage I was legitimately freaking out. It was day three and I thought this was it. This is how I'm going to break. I was so close to begging like a little bitch to get out of the cage.

She came three times on his cock throughout this session. When he finally came he did it inside of her pussy with a lot of loud groaning. They'd both been super charged and needed to fuck.

After he got off of her Ashley was spent but I saw in her eyes a realization as she spun and got down on her back.

"Come here, come here," she said to me. She pointed to her pussy. As I got closer she grabbed my hair and pulled me down, putting my face inches from her pussy.

It was at this moment I realized Jason pulled out more than I thought and his cum was all around her pussy and it looked as if it were still leaking out.

"Get in there!" she said loudly. "I know you've been wanting this to be part of the routine."

I did, but I was also mid-freakout about my own desires at the moment. Without hesitation, I buried my face in her pussy and licked up every single drop. The amount of cum was insane. I glanced up and saw Ash taking a video of me doing this.

Jason watched for a second, "That's fucking hilarious." As I finished, Jason went to the bathroom.

I came up from her pussy as disgusting ss you could imagine.

I was still straining so hard and panicking a little bit. or a lot.

"Baby.... baby, I think I need out. I cant..."

"No, no, no..." she interrupted, "it's been three days! You said no matter what you wanted to make it to 30 for the experience."

"It's so hard," I said.

"I'm sure it is!" she chuckled, "I know I couldn't do it." She sat up, still completely naked, and reached down to my cage.

She lifted everything by putting her hand under my balls and smiled as she looked down, "We're getting you your own thongs. This looks too hot."

I was trying to hold back tears.

"Babe, are you for real?"

I nodded and said I and felt like I was going crazy.

"You know how disappointed you'd be if you gave up after 3 days?"

I didn't answer but knew she was right.

"Don't worry, you only have ten times that long to go. Minimum."

I really wanted to cry now.

She continued, "If you really want out we'll do it but that'll be the end of this chastity stuff."

I sat there quietly and she leaned in, "And I'm really starting to love it."

She pulled back and said, "You told me your fantasy was for you to be broken. Is it really?"

Somehow I managed to nod.

She abruptly grabbed my chin and got our eyes to meet.

"So... break."

She got up and walked over to the bathroom and cracked the door. She spoke to Jason for a minute before turning back around to me. Her ass looked incredible with the red marks still on it from where he had manhandled her.

"Hey," I looked over to her, "Jason said he wants me to take a shower with him. Knowing him he'll probably want a blowjob already again, right?"

"Why don't you to get both of us some water and then go play some video games or watch a movie downstairs to take your mind off of your blue balls, if that's what you want."

Her words stung but I knew she was pushing hard to make me feel my fantasies coming to fruition.

I somehow managed a "Yes, ma'am," and went to get them both a glass of water. I came back a couple of minutes later and they were already in the walk-in. I looked through the glass and saw her behind him with her arms wrapped around him with soap in her hands.

I stood there for a second and neither of them looked at me. I put down the waters on the counter and I heard her say, "Thanks, cuck."

Somehow feeling more jovial I said, "You got it."

I walked out of the bathroom and bedroom letting them have the rest of the night. I played video games for about five minutes but ended up watching a movie.

My wife came down probably an hour later, still completely naked, and told me to take off my blanked. I was still just in my cage and thong.

"Good," she said. "I want you in just that. I think it's sexy... I don't know how that man reloads so quickly but he already came in my pussy again."

I felt the strain bad.

She stood up and said, "I love you. I'm proud of myself for not giving into your begging earlier. I'd be a terrible keyholder if I didn't remind you how disappointed we'd both be if I'd have let you quit."

I told her I loved her too and even thanked her for being so strong.

"One of us has to he," she laughed as she bent down in front of me, key dangling freely.

"Have a good night. We'll expect breakfast in the morning but we won't be up too early. He'll probably be doing things to me all night, you know how he is.."

With that she kissed me and I watched her perfect body slide out of the room.