The Andrea Arrangement

Andrea spent the night on Sunday - but got up early and left for work. Nothing happened that night or in the morning, to my disappointment. We did, however, text constantly through the week. Almost entirely sexual. I was at home and, as I've mentioned, didn't have to work since I had plenty of money, so I spent more time than usual that week drinking. And the more I drank, the more bold I became in my texts. When she asked what turned me on the most about her, I told her. Here was our text thread. She had a lot of misspellings not surprisingly...I left them out because otherwise this would be almost unreadable. Let's just say, I'm surprised she graduated high school.

"To be honest, I think ur hot but the way you take control is what's really gets me hard."

"LOL I know John. I've had submissive boyfriends before. Well not really but one once. I always just dated real tough guys with big dicks. But I REALLY prefer your type!!!"

Somehow I had a hard time believing it but I didn't care. In fact, after that last text I jerked off immediately. later that night, still drinking, I told her about it - about how what she said had turned me on so much.

"You naughty boy. Seriously, John, you jerkoff too much. I think we need to control that."

I definitely thought she was kidding. But the next picture was one of a chastity device, which I had only seen in some of my porn clips that I loved. It was light purple. I became very hard at the thought.

"This might be fun," she texted. "I want to try it. I also want to come over on Thursday and stay for the weekend. Order that cage. I'll be there by Friday."

I was drunk. I immediately told her "yes!!" and ordered it.

The next morning I woke with immense anxiety. Partly from being hungover but also from everything we had discussed. I mean, wasn't this all just a fantasy? and I'm not lying: in the exact moment I felt myself getting hard. I knew I wanted it. I also knew I could end it at any time, so why not see how this once in a lifetime opportunity plays out?

I ran errands and cleaned the house before she came over Thursday. You may wonder why I didn't just pay for cleaners: well, with only myself at the house it was very easy to maintain. I just didn't see the point.

All through the week I jerked off, at least 3-4 times a day, just thinking about Andrea and how this chastity cage would be. On Thursday morning the package arrived. It was early. I texted Andrea to tell her, and also to ask what time she'd be over.

"Sorry, I can't actually stay tonight. But I want to stop by on my lunch break. I'm VERY curious about this cage! Can you put it on for me?"

I was pretty curious myself. I decided to try it out. It fit but it was tight. It squished my dick into almost a ball. There was no way I could get hard. It had a key lock at the top. The entire device was purple plastic except for the lock.

She asked me to text her a picture but I didn't. She texted an angry faced emoji and then told me to leave it on. As lunchtime approached, I started to feel embarrassed and silly so I put clothes on over the cage. It was small enough where it wasn't all that noticeable.

The first thing she said when she walked in was, "oh, ya can't even see the fuckin' thing! That's good!" Then she aggressively grabbed the cage and yanked it. "How does it feel?"

"I can't really feel anything. It doesnt hurt. It's pretty tight though."

"Ha, good! I like my little boy locked up. Hey, I have to run back to the office. I just came by to see and give my little one a kiss. Let me see the keys."

I handed her the two keys. They were pretty small--i was worried she would lose them. She then walked out of the house.

"Hey! That's not funny bring those back!" I yelled. She turned and gave me the middle finger and smiled.

"Learn to keep it on! Just try it. I'll be back tomorrow morning." And then she backed out of the driveway and left.

At the time, I sort of thought it was funny but in the back of my mind i didn't doubt that I could just get it off myself. The problem was that I couldn't. It was just tight enough where there was honestly no way to get it off, short of going to the hospital or a local fire department.

So, I decided to have a few cocktails and watch movies. I'd wait until morning. I probably would have been fine but Andrea kept texting things that started to make me very horny. Getting extremely turned on in a tight cage is strange. It hurts but also sort of feels good. It's 90% pure frustration though.

"How's my little pet doing? You like being locked?"

"Not at all - this is hard!!"

"I doubt it's hard at all LOL LOL!"

"No, it can't get hard."

"I sort of own you right now don't I? I own that little dick if yours don't I?"

"Yes."

"Good boy."

I stopped texting. I needed to calm myself from getting too horny. The biggest annoyance wasn't even that. It was when I had to urinate. It never occurred to me that I'd have to sit. I tried standing but there was no way it would work without getting piss everywhere. As I sat there on the toilet I truly started to feel slightly "owned"....sitting wasn't my choice. I had to do it. So this was the first of many things that I had to do because if my circumstance. It was scary but also a major turn on.

That night was not easy. Men have natural hard ons all through the night. So each time my body wanted one it would wake me up. I woke up tired and cranky. And with a text.

"How was my little pets first night in a cage??"

I told her how horrible it was.

"Don't worry, I've read it gets easier. I'll be over soon."

"Ok. Don't forget the keys!"

She didn't text back. When she came over around lunchtime, she walked in wearing sandals and a very short pink sundress with lots of cleavage. It must have been the nicest dress she owned because I had never seen her look so good. She gave me a long, deep kiss.

"Hi pet." Hearing someone call you that in person is so erotic I can't describe it. It's one thing to have it in an email or a text, but when it becomes real life it's an indescribable wave of new emotion that envelopes you.

She even gave me a light slap on the ass. "Go get my bags and bring them in. I want my suitcase in the guest room for now." I was confused. I went out and sure enough she had not one, but three bags. One suitcase and two other large duffle type bags.

I brought them in. "Uhhh, are you staying awhile?" I only meant it as a joke -mostly-but I could tell it made her angry.

"I'll stay as long as I fuckin' want. I don't think the pet in the cage should be saying things like that. Put my shit in the guest room. Put that pink bag in the bathroom. And then make us each a drink."

I started to make us a drink. My emotions were wild. I was nervous about this whole thing. I didn't like things out of my control when I wasn't fantasizing and jerking off. But I was so overwhelmingly horny that there was no way I was going to push back. And it was all happening so fast.

She came out and grabbed the drink. She seemed back to her pleasant self.

"Let's go out side. I want to smoke." She went out and lit a cigarette. I followed. It was very warm so we sat in the shade. She looked over at me. "What do you think you're doin'?"

I had no idea what I did wrong, but fortunately she had a slight smile on her face

"When you're caged and we ain't in public I want you naked. You want to be my pet, don't you?"

"Seriously?" I honestly couldn't tell if she was joking or not.

She looked at me and snapped her fingers and point to the inside, as if to say "yes, go do it." So, I did. I came back out naked. The only thing I had on was my cage. Fortunately my entire backyard and pool area was fenced in and extremely private.

"Look at how cute you look in your little purple girly cage!" And then she laughed. God how I had hoped she'd take it off any minute. Instead we sat outside for another hour. She took a few naked dips and a few work calls. On her last call she said something like "ok, see you in a week or two."

I looked at her. "Ya," she said. "I'm taking a vacation and I'm staying' here. At least a week. You like that, don't you pet?"

"Yes, of course!" I was so horny. She stood there in her towel, completely naked.

"I'm going to change and then I'm gonna go out for a little." I gave her a look of confusion.

We went inside and I waited as she changed back not her sundress. I was sitting in the kitchen stool. She walked over and rubbed her hand on my cage. Then she walked over to the couch, bent over, and put her ass in the air. She wasn't wearing any underwear.

"Come here, pet. Lick my ass."

I stated to lick her ass cheeks. "No, I mean lick my fuckin' hole." So I did. I placed my tongue directly over her asshole and pushed in while licking around. She was very hairy but not as hairy as her pussy. I put my hands on her cheeks to spread them.

"Not so aggressive. Take your hands off." I did and kept licking. She tasted so good and I was so horny. She let out a small moan and then stood up and pushed me slightly away.

"Do you want out of your cage?"

"Yes!"

"Yes what??"

"Yes....please?"

"That's good enough for now. Give me your jeep keys. I'm not driving my piece of shit car to these nice malls around here."

She left and took my jeep. I was so horny and desperate. I looked around. I ran into the guest room to find anything of hers I could shove in my face but there was nothing there and had worn yet. I tried yanking on my cage. It did feel good but basically seemed pointless. It didn't seem possible to cum that way.

So, I sat on the couch and calmed myself and waited. Finally she texted.

"I bet you're pretty horny aren't you? How does it feel not to jerk that little dick every 5 minutes?"

I was honest. "It sucks."

"LOL awwww. I know it does sweetie. I'm going to let you out of it for tonight, ok?"

I nearly shouted for joy. "Ya that sounds great!!"

"But I need you to do something for me."

"Anything." I just needed to cum.

"I want you to Venmo me some money so I can do some real shopping."

"How much?"

"You decide. What you decide will determine what I give you tonight :) "

I thought about it. $300 seemed like a lot of money, so I venmoed her that and texted her to ask if she got it. She only wrote back "thnx". I almost sent her more but decided to wait.

She finally came home in the evening. As soon as she walked through the door she said "fetch my bags from the jeep. Where's dinner?"

I suddenly sound myself apologizing. "Oh, uhhh...I thought I'd wait to talk to you so we could decide together."

"That's nice of you but you should have texted me and asked. Because now I'm starving. Didn't you stop to think about my needs? Being on my feet all day, you had to have known I'd be tired and hungry."

I didn't answer but instead ran out to get her shopping bags. I couldn't see but it felt like clothes.

I ordered food and we both ate pretty quickly. She was on the phone with her mother talking about her day. And didn't mention me, but talked about how nice the malls in this neighborhood were and how tired she was from shopping all day. When she finished she hung up and went to the couch. I started to clean up.

"When you're finished come in here. I think it's time you get your reward."

I quickly cleaned up and walked to the couch. She lit a cigarette. She knew I hated it inside the house. "Go get the ashtray from outside." She was just daring me to say something. To push back. To tell her it was gross and to leave. But I didn't. I needed to be released.

I handed her the ashtray. "Good boy. Stand up."

She handed me a key. Unlock yourself. She watched as my dick slowly unraveled into a skinny hard boner.

"Now, I don't know what you're expecting but you didn't send me a fuckin' jackpot did you? DID YOU?"

"No, but I thought --"

"You thought wrong. What the fuck can you really get for $300? Sit down in the chair."

I sat down. She turned on her back and placed her feet over the edge of the couch end. Her sandals were still on.

"This is what you've earned. Take my sandals off. Massage my feet. Then smell my feet. And then I want you to lick them clean."

I did as she asked. I massaged her feet in the time she smoked two cigarettes. She had closed her eyes so I could tell it felt good. Even as I massaged them I could smell them. They were sweaty and dirty, and the smell was strong.

As soon as she "that's enough" about the massage I dove into her feet. I sniffed hard and immediately started to jerk off. I couldn't get enough.

I had only started to lick once or twice before I came. Cum sprayed onto my chest and hands. I let out a small involuntary moan.

"Already?? See, that's what happens when you don't cum every 5 minutes. It don't take you as long, and that's a good thing because it's not fair for me to have to sit and watch you for so long. Go clean up."

I went to clean up. I felt very strange. I was suddenly owned by her - at least it felt like it. I think what was weird was that it wasn't a role play. It wasn't like she was doing it at all for her pleasure, and honestly it didn't seem like she cared about mine. It felt strictly like a transactional kind of thing. I began to have serious doubts until I got out and started to dry off and noticed I was hard again. And then I was right back on the train.

I walked out into the living room and she was smoking a cigarette. I asked her a question.

"If I had sent more money, what would I have gotten?"

"Oh, much more. And I might have even touched your little dicklet." Then she walked over and kissed me on the cheek. "Let's put that cage back on and watch a movie together!"

It took awhile for my dick to get soft and limp again but as soon as it did, I complied.