The Andrea Arrangement Ch 04

The next few days were surprisingly normal. Nothing sexual happened, and I had my cage on, but we had done normal relationships type things. I showed her around the city, which she rarely had experienced living in the rural outskirts, and we went to several restaurants. Turns out she loves to eat out. We talked a lot about her life. It wasn't very complex, but did confirm that she had grown up pretty poor. She said she realized at a young age that men wanted her body, so she had a lot of boyfriends but liked to be the one in charge. The problem, she said, was that until me she never found a guy that was genuinely submissive...except one guy but she wouldnt say anything about him. i gathered that it was a long time ago. I wasn't sure how to feel about all that but I decided not to ask.

Toward the end of the week I felt like we were starting to get much closer. I finally admitted to her that I didn't really have a full time job, and told her the truth about my inheritance. We were sitting in my kitchen eating takeout food. That was when she proposed the first stage of an arrangement. Of course, she was smoking cigarettes but at this point I couldn't tell her no.

"Look. I know I'm exactly what you want. You're what I want too. And so... I'm kinda thinkin' I should move in." I was totally surprised. It was so sudden. And also, what about her home and work? I asked her about all of that.

"John. I'll move in here and I'll drive to my job every day. And I'll help pay your mortgage."

"The house is already paid off, you know that."

She smiled. "I know John. I was fuckin' with ya. So what do ya say? Huh? You know that little dicklet of yours would love to have me live here." She reached across the table and rubbed my cage through my jeans. I could feel my dick starting to swell inside the cage.

"Well... I think this could work."

She quickly took her hand away. "What do you mean work? I thought we were really becoming a couple. I thought you wanted this? Now you're making me feel like a fuckin' mooch??"

I back paddled fast. "No! Not at all! I really want you to stay. Sorry, it's just happening so fast."

She then sounded more relaxed and put her hand back over my cage and started to rub it. "Good. I know this seems fast, sweetie but it's for the best--for both of us. Now stand up and take your pants off and then sit back down."

I did as she said. She reached into her pocket and pulled out the chastity key. She stared into my eyes as she unlocked it. She then got up and moved behind me as I sat on the kitchen stool. She reached around and started to stroke my dick with two fingers. She leaned right next to my face and gave me a kiss on the cheek. Then she whispered into my ear. She smelled like a mix of cigarettes and perfume.

"Doesn't that feel good, John? Having your baby dick out of the cage? I can feel it starting to get hard." With just a few tugs with her fingers it was as hard as ever.

"Yes it feels amazing."

"Wouldn't it be nice to have this all the time? With a girl that knows what you need?"

"Oh my god yes!"

"You're not worried that I'm older than you, right baby?" I really hadn't thought about it much, but she was 11 years older than me, in her early 40s. She started to have some rough edges and she definitely didn't care about shaving, but she was still as hot as any 30 year old.

"Not at all."

"Good boy." She stroked harder. "You like it when I use my fingers on your dicklette don't you? Does that cum need to get out? Tell me."

"Yes. Yes! I need it out!"

"Good boy. Now stand up." I got up off the stool and stood there. She told me to cup my hands under my dick. "I want you to catch your yucky cum for me so you don't make a mess. Understand?"

"Yes!" She then stood right behind me and began stroking harder with two fingers. Her other hand started to squeeze my ass. And then I slowly felt one of her fingers work its way into my ass cheeks. I began to moan. I'd never felt any fingers in that area.

"Hold still. I want you to think about how fuckin' awesome it's gonna be having me live here with you!"

Right then she pushed her finger that was already between my ass cheeks directly onto my asshole. I instinctively jumped forward slightly. She pushed it in just a centimeter or two. It felt amazing. I wasn't sure if it was the actual feeling or just the mental aspect, but I felt very vulnerable and horny at the same time.

"Ohhhh, John, you like that, don't you baby boy? What a good boy." I moaned, and she pressed her finger harder against my hole. "Think about how much you'll love me, and how much I'm gonna own this hot, tight ass of yours!" And then I lost it. Cum squirted out of me and into my hand, as I let out a loud moan I could feel the hot sperm cover my hands and squirt into my palms and fingers.

"Ohhh! What a good boy! Doesn't that feel so good??" She kept stroking and it felt really good.

Finally she stopped and also pulled her finger away from my ass. I stood there with cum filled hands and suddenly felt embarrassed.

"Quick, go clean up in the bathroom, you're a mess." I walked in and started to wash my hands. The post orgasm clarity started to kick in. Was this really happening? That felt amazing but was I really going to have Andrea move in?

Almost as if she could hear my thoughts, and came into the bathroom at that exact moment and gave me a hug. It felt good.

"Did that feel good? I hope it did."

"Yes, it felt really good. I've never....uhhh..."

"I know. I've actually only touched one other guy down there. I think every guy would actually love it, but only certain guys seem willing to try."

We walked back out of the bathroom and I started to put my boxers and pants back on. Before I could pull them up, and started to place my cage back on. I had hoped she'd forget about it.

"What certain guys? What do you mean?"

"John, you know what I mean. Fuckin.... Like sissy....i mean... guys like you. Ya know...guys that like to be submissive. Like, not macho kind of guys."

"Like Ron?" Ron was the mechanic that owned the small dumpy shop where I had met Andrea. The muscular tattooed guy that didn't seem to like me.

"Ya, like Ron. You think he'd ever let a woman touch his ass? Ha! Fuck no. He only goes straight for the pussy."

I didn't respond. In that moment I realized she really saw me differently than the kind of man I always thought I had to be. But wasn't this what I wanted? I never felt satisfied with all the standard women, no matter how hot they were.

"See John? You need me. Trust me. Me moving in will be so fun for both of us." She then jumped over to me and gave me a big hug. She seemed really excited, which made me feel good.

After that conversation she wanted to begin the process immediately. We decided she'd move into my room upstairs and we'd keep the guest room downstairs open. We drove to her house that evening with my jeep to pack all her stuff. When we got there, I was reminded of just what a dump her place really was. We went into her place and she began to grab a few bags and told me to place them in the jeep.

"This is all?" I asked.

"Ya honey. Everything else is shit. Don't worry, Im still working here so I can always grab anything i forget." The thing was, there's no way she had more than a few weeks of clothes. I didn't understand it at the time, but looking back it was clear she had planned out everything.

We brought her bags to my jeep and I began loading them into the back as she sat into the passenger seat. Suddenly Ron came out from the garage, having been working on some car. He wore a tank top which showed off his enormous muscles and tattoos. He was dirty and greasy and looked pissed off, as usual. He stopped at the passenger door and started talking to Andrea. They were practically whispering, but I figured it was about work. i dont know what he said but she was quiet and seemed sad when i got back into the car. i tried to ask but she brushed me off. by the time we pulled into my driveway she was crying. Not a hard cry, but a few tears were visible. And she was silent. Turns out, leaving that shit hole was a lot harder than she had expected. Moving into a house like mine in a wealthy neighborhood was just too strong of a change--or at least, that was her concern. She felt like it wasn't really her.

"Well," I said. "I'm not really sure what you want. I mean, what if you don't fully move in and we just keep doing what we're doing?"

"No! I really want us to live together. It's just...my whole life is back there and I don't know anyone here and I'm not one of these rich asshole types like that guy." She pointed to one my neighbors who appeared to be putting golf clubs into his BMW.

She grabbed my hand and looked at me. "Honestly, John, what I really want is for you to move in with ME." Once again, I was surprised. I mean, that whole place was a shithole. As I've gotten older I could see how someone like her wouldn't or couldn't want to leave her roots but there was no way I was going to live there. Or so I thought.

"Andrea. I mean.... I reeeeallly like you, as you know, but I mean... "

"I get it. You already have a house. I know. I get it."

"Well, it's late now. Why not just stay tonight and think about it? Maybe you'll change your mind?" She looked at me and grinned.

"Or maybe you'll change yours? How about this...I'll stay for the rest of the week. Try it out."

We got out of the car and went inside. We brought her bags in.

That night, and for the next five nights, was torture. In a good way, but still torture. We had our normal days - she would go to work and come home, and I would do my normal errands and play video games and such -- but every evening she had me going down on her with zero reciprocation. She wouldn't allow me to ask about it either. The last few nights she just sat in the living room on the couch and opened her legs and said "make me cum John" as she smoked her cigarettes. As much as I loved doing it, it was life torture. My dick would swell so hard against the cage. No matter how much I tried to yank on it I couldn't cum. And then I would have nearly sleepless nights. When Andrea would drive off for work I would look everywhere for the keys and try everything to get my dick to cum. It was all for nothing.

Finally, on the 6th night, when she opened her legs and asked me to go down on her, I put my foot down.

"Andrea. I'm dying over here. Please. I need to be let out of this damn thing!"

She stared at me from the couch. "What's wrong? Can't handle it? Come over here." She patted the couch. I went over and sat next to her. She lifted up her t-shirt. She liked to wear old raggedy t-shirts for some reason. Underneath, her beautiful breasts popped down. They were so perky and big. She hadn't showed them to me for a long time. "Suck on these, John."

I dove in and sucked on each nipple. I kept going back and forth. "No, no sweetie. Just one at a time. Here." She cupped one of her tits and gently put it in my mouth. "Don't lick, suck. I'll let you know when to switch."

We did this for a long time as she watched TV.

"Feel better baby?"

I stopped sucking. "A little."

"Aw. My poor baby. That cums all built up inside isn't it? Your little baby ball sack can't hold all that cum can it? Get up and take your clothes off."

I can't describe my excitement. 5 days and nights of being caged while going down on her delicious pussy and sleepless nights...finally about to get some action.

I undressed. She then instructed me to get on the couch facing behind --on my knees-- with my hands on the back of the couch. She then stood up and put her hands on my ass. She rubbed all around them, and occasionally one of her hands would rub my caged dick. I moaned.

She stood back and suddenly I heard her opening something. I heard a bottle open. Then I heard her putting on gloves. I started to turn around.

"Face forward." So I did. And then I felt it. I felt a cold, wet, gloved finger pressed directly on my asshole.

"Remember this??" She said.

"Oh my god yes."

She pressed it harder. I felt the tip of her finger starting to enter my hole. Her other hand rubbed my back.

"That's a good boy. Keep face forward. Come on, open up for me. I know you want this. And I know you want to get that cum out, don't you?"

"Yes. Please. "

My dick had swelled so hard against my cage that its skin was seeping out of the cage. Her finger went further and further into my ass, until suddenly I felt it stop. It was pressing against something. I got scared for a moment. Was this the wrong direction or something? What was she hitting? She could tell was nervous.

"Face forward! Just relax. If you tense up I can't get it all the way in. Just fuckin' relax and take it. You can do this. Breathe. You're just very tight that's all."

She kept rubbing my back. I started to relax. She kept moving her finger inside and out up against this spot.

"Come on John. She me how you can open for me. Show me you're my bitch!" And right then she pushed forward her finger right passed what I thought was some kind of blockage. Whatever it was, it felt unbelievable once her finger was all the way in.

"Ahhh! Ohhhhh!" I moaned. She moved her finger in and out and all around. I looked down and saw that my couch was soaked below me. Had I came?? No, it was all leaking precum. Tons of it.

"Goood boy!!! You're doing great John. Keep going. Keep that hole open for me." Then and pushed her finger in and out and all around more aggressively. I felt streams of precum leaking out of me. She started to keep her finger entirely in. She was pressing against one spot.

"Yep. That's your special little girl spot John. That's what I call it. Hit that fucker and all that cum will start to come out. It's what we call milking, John."

It felt amazing. I remember realizing that what she was talking about was probably a prostate massage. I had only seen them in porn clips.

Turns out, it really does work. I started noticing that not only was a leaking more pre-cum, but that what I was releasing was thickening. It was cum but without the orgasm. We did this for about 30 minutes.

"I think we're done John." She continued to move her finger around. There was a large thick puddle of cum below me on the couch.

"Ohhh," I moaned. "Please no!" I didn't want it to end. I felt like maybe I could had an orgasm if she kept going. I felt a little relief but no less horny.

"You want to REALLY cum don't you John? But we just got all that cum out of you! We milked it out, together. You did such a good job. Look at that mess you made."

"Please??"

"No."

She pulled out her finger and took off her glove. I started to get up.

"Stay right there." She stood up and pulled down her shorts and underwear. Her tight, tan thighs looked so amazing. She walked over to the other end of the couch. She sat down and spread her legs. Her hairy bush seemed bigger than in past weeks. It extended down her legs a bit. Even her legs were hairier than usual.

"I bet you want to stick that little thing in this pussy don't you?"

"Oh wow. Yes! Yes I do!"

"Stick your finger in it." I reached down and slide my index finger in. "Now pull it out and suck on it until tell you to stop."

She watched as I shoved it into my mouth. It tasted so good. "Your finger felt like your little dick! Just as skinny." She laughed. "suck that finger good." As I sucked, she reached down and started to unlock me. I couldn't believe it. As soon as the cage unlocked my dick sprung up straight and hard.

"Now sit in the couch." I sat down and she flung her legs over me. She placed her hand behind me on the top of her couch and slowly started to sit into my lap. Then she brought her pussy directly over my dick and sat right on it. Oh my god. My dick went straight into a wet, hot hole and it was very hot.

But she didn't move. She said and stayed there.

"How does this feel John?"

I had no words. I instinctively started to try to move my hips up and down. She slapped me lightly on the face. It probably would have hurt if I hadn't been so incredibly horny.

"NO! Do not fuckin' move. I know this feels good for you. Do you want more? Answer me."

"Yes!"

"Do you want to cum?"

"Yes!" I honestly think if she had sat there in that exact stationary spot I would have eventually came.

She looked deep into my eyes and brought my hands to her tits. The she wrapped her hands around my neck and gave me a very long kiss with her tongue deep into my mouth.

"Baby boy. Move in with me to my place. I'll give you everything you need. Do that, and I'll let you cum. Right inside of me. Just like a real man." Then, she slowly lifted her has in the air and the quickly plopped it back down onto my dick.

"Ahhh" I moaned.

"Come on baby. What's your answer going to be?"

"Yes! Yes I'll move in with you!"

"Oh good boy!" And then, to my surprise, she just hopped off me.

"Wait?? Where are you going??"

"I told you, I'll let you cum when we get to my place. First I want to be sure you're serious." Then she came back over and sat next to me. And grabbed my dick with two fingers and started stroking. "You were serious, right? You want me to make this little baby dick cum right?"

"Yes!" And then she stopped and started to put her clothes back on. I swear, if she had stroked it one more time I would have came.

"Can we go tonight? Please?"

She laughed. "Oh John, I love when you're this desperate. This is when I know you'll do anything for me. No, we'll go in the morning."

"PLEASE!"

"Don't be so pathetic John. If I let you cum now, will you promise you'll still move in with me??"

"Yes, of course! I want to! I PROMISE!!"

"Are you going to pay my fuckin' rent??"

"Yes! Yes I will!"

"All of it? All of it John. Not your little hand-me-outs. It's a lot."

"Yes, all of it!"

"Ok John. You've earned it. I don't even know if you have any cum left in those little balls. Let's see. Lay down on the couch."

Naked, I laid down and looked up at her. She was all dressed again at this point. She looked down at me. "Jerk yourself." I quickly grabbed my dick. It was the first time I had touched it in what felt like weeks.

She then lifted her foot and placed it directly onto my mouth and nose. I breathed in hard and immediately started stroking fast. She moved her foot up and down as I stuck out my tongue and licked the sweat and dirt. In less than 30 seconds I came all over myself.

"Ha! So pathetic, that was like 10 seconds. Feel better?"

I laid there exhausted.

"Yes."

"Good. Start packing your shit." She grinned.

I wasn't sure what I had just signed up for, but I did know that she was the hottest woman I'd ever met. As these thoughts were going through my head I heard her on her phone in the other room. i couldnt make out everything, i heard her say this:

"yes, we'll be there tomorrow. i cant wait either. ya, this will change everything."

Then a pause. And then: "Yes, a collar."