Not Careful Enough Ch. 02

When I woke up I felt sticky and I didn't know why at first. Then I remembered my late night session and how I didn't even clean myself off. I got up and went to the bathroom and used a washcloth to scrub off the dried cum.

I was startled when there was a knock on the door and my dad's voice sounded off.

"A package came for you. I put it in your room."

I tried to think if I had ordered anything recently but I couldn't think of anything.

"Thanks dad," I said.

When I got to my room I saw a largish box in my bed. It didn't have any shipping labels or return address. Just a label with my name on it. I grabbed a knife and opened it. When I saw what was in it my heart sank.

The box was full of dildos, outfits, butt plugs, lubes, and makeup. How did Jerry get all of this stuff out together? He just said his stuff wouldn't even show up for a few days. I grabbed my phone and shot him a text.

"WTF? How did you get all of this stuff so fast?"

I didn't have to wait long for a reply.

"I take it, you got my care package?"

"Yes I got your box of deviance. What do you expect me to do with it?"

"All good things in time. First, how about a good morning?"

I rolled my eyes and sighed.

"Good morning," I texted back wishing I could relay annoyance.

"Good morning, what?"

"Good morning sir," I texted back.

"Better. Now, how did your night go? Did you enjoy the video?"

"It was fine. I've seen better."

"Not like this you haven't. Did you cum?"

I wasn't sure if I should answer that.

"Maybe..."

"Hahaha I knew you would. That's good, that'll help. In the box there should be a chastity cage. Put it on."

"Now? I just woke up?"

"Yes now. And send me a picture when you do."

I put my phone down and searched through the box and found the pink chastity cage. It had a little lock on it but the key must've fallen out. I opened it up and pulled my pants down. I was still wearing those panties. Once I got it on I locked it's closed, it needed the lock or it didn't stay on. I then grabbed my phone and took a picture of it.

"That's a good girl. And don't worry I'll teach you to cum another way."

"I didn't find the key."

He then sent me a picture of a tiny little key.

"I have the key. I'll decide when and how you cum."

My heart sank again. I just let myself get tricked into a chastity cage. How could I have been so stupid?!

"Now find the smallest butt plug and insert it."

I dreaded that command. I've never had anything up my butt before. I saw a lot of videos about guys getting a finger up their butts during blowjobs or pegging videos. I even came across sissy hypnosis porns that encouraged you to play with your butt while watching but I never got curious about it. Now I didn't have a choice.

I dug through the box and found the smallest butt plug. There are three metal plugs of various sizes. There was a box of a butt plug looking thing that had a remote with it. I wasn't sure what that was about. I grabbed one of the bottles of lube and applied it to the plug and then a generous amount I rubbed to my hole.

I squatted down and probed around with the plug until I lined it up right and pressed it in. It kind of hurt even with the lube. I had to start and stop several times. I was starting to get discouraged when I felt it spread open my butt hole and it sucked it to the hilt. It was the strangest sensation I've ever felt. I just stayed there breathing until I stood up and grabbed my phone.

"Now what?" I texted him.

"Send me a picture of course."

I rolled my eyes and reached my phone around to get a picture of the fake jewel shining from my butt.

"Good girl. Wear that for an hour then take it out for two then back in for an hour until tonight."

"What's tonight?"

"I'll be over to show you the rest of the box. Until then, enjoy."

Why was Jerry coming over again? I would ask my dad but it felt strange to ask. Like how could I not make it sound like I was eager to see him again.

I pulled my pants up and it was strange with the panties and cage. As I walked around I could feel the plug lodged in my butt. I set an alarm on my phone so I remembered to remove it. When I left my room I felt like I was correcting my gait every step.

When I got downstairs my dad had breakfast laid out. I sat down without thinking and thumped the plug making me jolt in surprise. My Dad handed me a plate and I served myself.

"Jerry will be joining us for dinner again tonight. I hope that's okay."

I tried to sound none committal.

"Yeah of course why wouldn't it be?"

"Well I recognize I'm not home a lot and having someone else over takes time away from us."

"It's fine Dad, I get it. You're trying to make him feel welcome. It's no big deal."

"I'm glad you understand. Well eat up then join me in the garage I need your help with the car again."

The car was a vintage mustang. It was my dad's pride and joy. He insisted we work on it together even though I really didn't care about cars. When I finished my plate I helped clean up and put the food away. Dad always made a lot so I had food during the week. When I got to the garage dad had me help him jack the car up so he could crawl underneath it. By now the plug was kind of hurting. When I heard the joyous sound of my alarm I quickly grabbed my phone and ran to the bathroom and pulled out the plug. It felt really good to have it out. I washed it and put it in my pocket. I set a 2 hr alarm and joined my dad.

We were in the garage for a while. We finally stopped and I went back to my room. It was almost time to put it back in. I compared the size of the one in my pocket to the biggest one and it made me gulp.

For the rest of the day I did what I was told and kept myself plugged. What was truly uncomfortable was that I was often straining against the chastity cage. I really wanted to get hard but I just had to lock myself in this stupid cage.

When evening came I kept looking out my window at every sound looking to see if Jerry had come yet. Not that I was eager to see him, just that I was anxious about what was going to happen tonight. Was he going to make me jerk him off again? Or something worse?

There was a knock on the door and I looked and saw Jerry's car. When I got downstairs dad was already letting him inside. When he saw me coming down the stairs he winked at me behind my dad's back.

We all chatted a bit in the living room. When the conversation died down Jerry asked if he could use my computer again to check on his stuff.

I knew it was a ruse but I agreed and escorted him upstairs to my room. Once in my room I heard him close the door behind him. He locked it and I turned to face him. He had a mischievous grin.

"I thought he'd never shut up. Now show me what you're wearing."

"Seriously right now? But my Dad...?"

"Relax, just a quick peek."

I sighed and pulled down my pants to reveal my pink panties and the pink chastity cage. I held my hands out presenting the display.

"You look so cute. Now let me see the plug."

I turned around and slightly bent over and spread my ass cheeks. I was surprised to feel him behind me. I straightened up and felt his bulge press against my backside. He ran a hand on my bare butt and with a finger thumped the jewel. The sensation made me squeal. He whispered in my ear, his breath warm against my neck.

"How did it feel to have something in your butt all day?"

I tried to squirm away but he was holding me tight.

"It was uncomfortable" I mostly lied.

"Oh don't be like that. I bet you liked it more than you think." He chuckled, giving me a peck on the neck.

The feel of his lips on my neck sent shivers down my spine. I bit my lip so I didn't make a compromising noise. I reached my hand back to push him away. I could feel his bulge twitching against me.

"I've been thinking about you all day baby girl."

He ground his hips into me as he spoke.

"Now let me give you the rest of the box. Where is it?"

Glad to be free of his embrace I pulled up my pants and pulled out the box from its hiding place. Jerry opened it and pulled out various items.

"I got you a couple of outfits, schoolgirl, maid etc. You already found the butt plugs."

He pulled out that box with the butt plug with the remote.

"This is such a fun little toy. It is a thrusting plug. Don't worry you are not ready for it. There are some makeup kits here. I'll send you some tutorials this week when you get the house to yourself again. I got you a couple of dildos. They both suction cups to the wall. Everything a budding girlie needs."

He turned back to me smiling.

"We should probably go back down. My dad will get suspicious," I said, averting my eyes.

"Sure sure we can't have that."

He walked to the door and unlocked it. He held the door open for me and I walked past him. When I did he gave me a smack on my ass making me jump. When we came back downstairs my dad was outside firing up the grill. I didn't want to stay inside and be alone with Jerry again so I went and joined him. We all sat around outside and chatted some more.

"So what's this I'm hearing about a vintage car?" Jerry asked.

"Oh you heard about that did you?" My dad chuckled as he put the food on the grill.

"Mark, show Jerry the mustang. I think you'll appreciate it."

"I'm sure I will," I heard Jerry say under his breath, mostly for my benefit.

I saw the ruse. It was just an excuse to get me alone. I shuffled my feet but I got up and showed Jerry to the garage. I was half way in when I heard the lock set on the door.

"I can't tell you how tired I am about hearing about this damn car," Jerry said, walking towards me.

I backed up until I pressed up against the side of the car. Jerry kept marching toward me like the Terminator. Once he was pressed against me I felt his crotch press into mine. He reached his arms around to cup my butt and he nuzzled my neck. I had my hands pressed against his hard chest. I knew I couldn't stop him. He was too big and muscular.

He whispered in my ear as he kissed up and down my neck. Sending shivers down my spine.

"Mmm, I've been thinking about you all day. Imagining what I'd like to do to you. How much I want to bend you over this stupid midlife crisis car."

I gulped nervously. I didn't know what I should do.

"Don't worry baby. I know you're not ready for that."

He pulled back and put a heavy hand on my shoulder gently pushing me down. I got the idea and sank to my knees. I was trapped between the car and this bulk of a man. I was now eye level with the bulge in his pants. As he fiddled with the buckle. I was panicking on the inside.

When he dropped his pants his standing erection bounced in the air, nearly hitting me in the face. I know I saw it last night and even touched it but seeing it this close. I gasped in amazement. It was so huge!

I heard Jerry chuckle and looked up at him with what I'm sure must've been frightened eyes. He caressed my face with his hand and pulled my head closer to his hard cock.

"Come on baby, give it a kiss."

I stared straight ahead and licked my dry lips. I really didn't feel comfortable with this but I pucker my lips and planted a kiss on the head of his hard cock.

"Good girl. You look so cute down there."

I know it wasn't exactly a compliment but it still made me feel warm and fuzzy. I gently reached a hand up and grabbed his cock. I started to slowly stroke his cock inches from my face. I was concentrating on my actions. I didn't realize I was biting my lip.

Feeling bold I straightened up and licked my lips. I knew this is what he was wanting me to do. So I brought my face closer and felt the head of his warm cock on my lips. I opened my mouth to accommodate it and felt it slide past my lips and over my tongue. I couldn't believe what I was doing. I was on my knees actually sucking another man's cock. Does this make me gay now?

I started to bob my head and create a vacuum with my mouth. My jaw was already getting sore from being stretched around this thick cock. Jerry put his hand on my head and grabbed a handful of my long blonde hair.

"That's a good girl. Keep sucking that cock. Work the shaft as you do it. That's it baby. Are you sure you've never done this before?"

My eyes met his and I shook my head on his cock.

"Such a good little cocksucker. Now let's see how far down you can take it."

He let go of my hair and put both hands on either side of my head and began to push. I raised my hands to rest on his muscular thighs. I squinted my eyes the more that he pushed into my throat. When I started to choke and gag he didn't stop at first. I pushed on his thighs and he backed off enough for me to get a deep inhalation and when I did he redoubled his efforts and pushed even further than before. I was starting to panic from all the gagging and choking I was doing. I couldn't breathe. I pounded on his thighs but he just kept pushing. Finally he pulled out and I dropped to the floor heaving and coughing.

"I suppose that's pretty good for a rookie. You nearly got half of it. Come one girl you're not done yet."

He pulled me up and pushed my back against the car. My eyes were still watery and I just opened my mouth when I felt him slapping my face with his heavy cock. With my mouth open he just pumped and pumped using my face like a fleshlight. When I was finally able to open my eyes again, I saw his phone in my face. I tried to shy away but he held me firmly in place.

"Hey hey hey don't worry this is just for me. That is of course unless you want to stop right now. I can show your dad what a filthy cocksucker his sissy son is. Maybe even the boys in the squad would love to see this video."

I relaxed and Jerry continued to fucked my mouth.

"That's what I thought. Don't worry we are almost done here."

He said he was almost done but it felt like forever until I started to notice the signs that he was about to cum. I braced myself. I expected him to just cum in my mouth but suddenly he pulled out and with one hand on my head and the other stroking his cock I realized what he was about to do.

He erupted in a torrent of thick sticky ropes of white cum all over my face. A few shots landed in my mouth but the first big shots plastered my face right between my eyes. He was grunting so loudly I was afraid my dad might hear him. When I was truly drenched in his thick semen he released my head but I was in shock to do anything but just sit on my heels.

I saw him pull out his phone again and snap a couple of pictures. I don't know if he said anything to me. I was in a haze. It took me a minute to even register that he had left me there on my knees, his cum dripping down my face. I felt like those girls my porn videos.

When I got up I looked around for something to wipe my face with. When I found a clean rag I wiped what I could and hoped anything else wasn't noticeable. I then realized that it was time to remove the butt plug so I figured I could do that right now. When I left the garage I poked my head out and didn't hear anything.

As I returned to the living room I saw my dad and Jerry outside laughing amongst themselves. I figured this was my chance to sneak off to my room. As I was crossing the room my dad saw me and told me to join them outside and food was done.

I joined them outside and my dad handed me a plate of food which I ate in silence. When I finished I asked to be excused and my dad allowed it. Then I went up to my room.

Once in my room I sat on my bed and just kind of zoned out. I just sucked a dick and the worst part was that the whole time I was on my knees and sucking that dick, I could feel my penis straining against this ridiculous cage.

At some point I heard the door open and shut. I looked out the window and saw Jerry leaving. He didn't even say goodbye. I mean why would he? He got what he wanted. Except there was a whole box of stuff that I haven't even begun to go through.

I got a text alert. When I looked at my phone it was from Jerry. He must be sitting in his car. He sent me a picture of my face covered in his thick white jizz.

"Next time I'll really make you feel pretty."

I didn't know how I should respond to that. There was going to be a next time. Another message came in while I was contemplating the first.

"Tomorrow I want you to move up in butt plug sizes."

"Okay," was all I texted back.

"Excuse me?"

"Yes sir, I'll move up in size tomorrow," I corrected myself.

"Good girl. You did good today, keep it up. We are going to have lots of fun."

"Yes sir," I texted back.

I put my phone down and watched him drive away. Now what was I supposed to do? I couldn't watch porn because I was still locked in this cage. A part of me wanted to watch that video he sent me last night.

I decided to take a shower first. It was awkward to shower around the hard shell cage but I guess I did the best I could. When I got back to my room I put on boxers and left out the butt plug for the night. I washed it in the shower.

I crawled into bed and just stared at the ceiling. I really wanted to watch something. I didn't know if I was just bored and I normally watch porn when I'm bored or if I was actually horny.

Cutting my losses I opened my phone and found the link from last night. When I clicked on it the video was different. It was still spirally and colorful but it didn't start the same.

"You are a sissy cocksucker. You love to suck cocks."

It flashes images of women sucking and deepthroating various cocks. In between those images were close up images of big hard cocks.

Now this was torture. I was really straining to break free of the cage. I had to stop myself from watching more. I turned off my phone and rolled over. The cage was uncomfortable to sleep in.