Pizza Delivery with a Twist Ch. 13

Let's check the Saturday scorecard. I sucked off my new friend Chase to start my work day and left with only a nice tip and a boner. I'm 0 -- 1 for the day. Then I sucked off Ken with his wife's approval and left with a very big tip and another boner. Now I'm 0 -- 2 for the day. Around 10 pm I caught Zack and Miss D having sex and had to help them both out with a few of my good ideas. So, by 10:30 pm I'm 0 -3 and it seems like I'm going to have to jack myself off.

How does the cute one end up being 0 -- 3 on a Saturday night? I better win one soon. Wait, I might be 0 -- 4 if Ken's wife Naomi is getting pounded by her frisky husband, especially if I'm not there to watch? I hope she is on her hands and knees.

I made a crazy proposal to Karen. I suggested that her and her boyfriend Todd stop by unexpectedly Tuesday while Josh and I were getting hypnotized by sissy videos. Josh needs some action and Todd needs some faggot ass. However, I had to offer myself up to Karen as payment.

I'm standing at 0 -- 4 for the night, so I am so ready to leave.

"Sal, you got anything for me?"

"No Brie, the Summer Festival is keeping us slow again. I'm glad it's over tomorrow morning. One of you can go home if you want to."

In the background there were a few voices from the chorus line. "You mean Brie can go home early, right?"

Sal wasn't looking at us so I turned to face my jealous co-workers and lifted my shirt and exposed my bra to the small crowd. I finished my response by sticking my tongue out. It was actually well received. I guess Suzie was right, they all do want to see me naked. I pulled my shirt back down rather quickly when Sal spoke again.

"Karen, can you cover Josh's line for the next 2 hours?"

"No problem Sal. But just so everyone knows, next weekend I will need to leave early. I have plans with Brie. I'm calling it now."

"Noted. Josh you can go if you want to."

I gave Karen a look. She smiled and made a quick stroking motion with her hand. Then she turned to the team and lifted her shirt and showed her bra. She really fills out a bra nicely. Show off.

I have a few possible solutions to my 0 -- 4 record. Ask Zack for a late-night visit, ask Josh to stop over now, go to Miss D house and see what happens or stop by Lisa's house to see if anyone is willing to help me out. I thought I might start with Zack. He was heading my way anyway.

"Brie, I'm glad there are no secrets between you and Miss D. It was the right thing to do. Anyone else on the list that should know?"

"Probably everyone, but CD's don't start with that. If I get called out, I won't deny it, but I'm not going to start with it. I actually like the way it happened with Miss D. She developed a comfort zone with me before figuring it out and nothing bad happened."

"I'll support whatever decisions you make. Now, what are you going to do for the rest of the night?"

"I don't have a plan. I'm just happy to be off work. The Festival is closed so I suppose I'll get cleaned up a bit and kick my feet up. Maybe watch some TV and doze off. Why?"

"Well, why don't you text Suzie and ask her if I can visit you after work tonight. She would take her phone to wedding, right?"

"What, why would I ask her?"

"Because she is your master and she needs to provide you with permission."

"She is my Mistress. Mistress Z. How do you know this information?"

I looked over towards Karen. I gave her a look that says I am mad and I am glad. She gave me the hand stroke motion again and smiled. That's when my phone buzzed. It was Suzie.

"Zack can fix your oven tonight."

"It will be a big step."

"Karen left her lube in you room."

"I seen it. Go dance."

I put my phone in my pocket.

"What time will I be expecting you and what will you need?"

"I'll be at your door at 1 am. I want you to go home now and shower. Give yourself enough time to fix your wig properly. I would like the short blonde wig, perfectly in place. I would also like you to have your boobs tonight. Let's say a black bra and panties set? You will greet me at the door wearing those two items under your bath robe. I will take a shower alone to wash the day away and you will bring me a beer while I'm in the shower. That's our thing now. When I get out of the shower you will be in the bed waiting for me, still wearing your bra and panties. I just so happened to have clean clothes in my trunk so I will have fresh boxer shorts. I will work on your oven with my tool. I'll cook it twice if I screw up the first one."

"Sounds like a plan, but what about the soap thing? The soapy B?"

"Good point. You can apply the Soapy B when you bring me that beer in the shower. Just a few strokes."

"Anything else?"

"Well, I've been told that Karen must supervise us, like a chaperone. Is that a problem?"

"I'll see you both in a couple of hours."

About that time Karen was grabbing my arm and dragging me to the Ladies Room. She had a small box in her hand.

"Karen, why didn't you mention this while we were talking before?"

"Shut up and hurry. Here, open up the box. I need to get your leggings down. Suzie asked me pick this up for you yesterday."

She proceeded to remove the bottom half of my clothes as I opened the box. It was a butt plug with a bright blue bejeweled end piece. The size wasn't frightening, it almost looked perfect. My stare was frozen on the plug when Karen broke my glare.

"Bend over a little and get ready for insertion. But first, I'm going to fuck your mouth with it. You know, to get it wet."

Karen 2.0 keeps throwing surprises at me. Before I knew it, she had one arm around my neck and the other hand was pumping my mouth with my new toy.

"Get plenty of suction on it. Get it real wet. That's it, Brie suck your new butt plug like it's Zack's dick. It has to be wet. OK, open up your mouth and bend over so I can open up your tight little ass."

I bent half way over and grabbed my calves. I was fully presented. I also hoping no one else walked into the bathroom right about now. All of a sudden, I felt something wet touch my rub bud, but it wasn't hard plastic. It was soft. OMG, it's Karen's tongue. She's licking my cake spoon and I'm about to faint.

"I know you like that Brie. I needed to get you wet as well. I'm going full insertion now. Prep yourself."

Oh my, I felt the insertion. It was a big insertion and then it popped around the reduction area. It was in. Karen slapped my ass hard.

"It looks good Brie. Very sissy like. Now you have to leave it in until the last moment. You want to be a little stretched before Zack plows this tight faggot asshole. The end piece is a pretty color too."

"Don't call me a faggot Karen."

"Sorry sissy. OK, I'm done back here. Let's get you dressed and on your way. I know it's new to you, but no matter what, leave it in. Also, it's coming out with a plop, so do it when you have a private moment and have a place to put it out of sight by your bed. Now go get that dick."

"I'm going to take a shower."

"OK, take it out, clean yourself and the plug and put it right back in. You need to be stretched."

"Thanks Karen. I better head out."

"No head tonight sissy. This is all about your true cherry. I'll see you at 1 am.

I have two hours to get ready. I showered first to get that over with. Done. I went through my drawers and closet to get everything else ready. Every cross dresser has matching black bra and panties. Done. I pulled my blonde wig from the closet shelf. It is super cute and has a red head ban as an accent piece. Done. My largest 34C implants. Done. I wanted to add thigh high sheer black stockings, but he did not request them so I laid them over the dresser in plain view. Just in case. I placed Karen's tube of Electro Glide on my Bed Stand and put the little butt plug box on the bottom shelf. Maybe I will move the box to the bathroom. I'm such a rookie.

On a side note, I have worn the plug for over one hour and I hardly know it's there. Something I should done over a year ago. Even straight folks should give these things a try.

I moved my vanity table chair and positioned it to where I thought Karen might like to sit, because she is a freak and likes to watch things.

I spent the rest of my 45 minutes getting dressed and adjusting my blonde wig. This wig is so sassy and cute. I'm not sure I'm all that as a blonde, but he requested it, so he gets it. Add the silicon breast forms and I'm ready for company. Oops, where is my bath robe? Do real women have a checklist or something? There is a lot of stuff to do and remember. Slow down Brie, you're starting to sweat.

Then there was a light knocking on the door. I answered the door as requested in my black bra and panties and bath robe. I left the bath robe slightly open in case there were any questions or doubts. Karen plunged through the door first and had Zack by the hand. They both gave me the once over as I closed and locked the door.

"Right on time as always. Thank you both for coming over. Karen, I don't know what your plans are exactly, but I have a chair in for you in the bedroom to sit in or you can stay on the couch. Zack, the shower is ready for you with fresh towels. I won't mind a moist body if you don't dry off completely. I'll bring you a beer once I hear the water running."

Without a lot of words, Zack went one way and Karen went the other way. I went to Kitchen and grabbed a beer and went to the bathroom. I didn't even knock. I opened the curtain and set the beer down on the shelf. I used my other hand to stoke his dick a few times. He already had it soapy. Just a few strokes. I returned to the bedroom.

"I like the chair. Thanks. That wig is hot. How does the plug feel?"

"Wonderful. I love it."

"OK, here's what we're going to do. As Zack is crawling into your bed, you point your ass at me and I will extract the plug and put it away in a wash cloth. We'll have to be slick about it, but we can do it. The water shut off. Showtime. Go get a wash cloth and an extra towel."

"What's the towel for?"

"In case you two get all messy."

I retrieved these two items from the Linen Closet and returned to the bedroom. Karen was busy removing her clothes when I returned. I couldn't worry about her as I had just enough time to crawl into bed before Zack entered the room. Karen, in her bra and panties, walked over and turned the light off. I lifted the blanket in that inviting fashion and he climbed in. I scooted my butt towards Karen so she could extract the plug. Mission accomplished. Zack looked over at Karen.

"Karen, it seems to me that you should be holding one of those Dom switches or something."

"It's at home. Brie, do you have something else I can use?"

"No, I do not."

"I'll leave now and give you two some privacy. I do not want to leave, but I respect your entitlement to privacy."

"I don't mind if you stay Karen. Zack, what say you?"

"I'm getting used to an audience, so I'm good."

"I will close my eyes if your intimacy involves kissing. Or is it game on?"

"We don't kiss. Will you hand me the lube please?"

Karen stood and went to the dresser to grab the tube of lube. She extended her arm to hand it to me. I grabbed her arm and pulled her into the bed.

"Chaperones should always be close by. We don't know exactly what we're doing."

"Agreed. Zack, point that monster my way and I'll lube you up. Brie, position yourself on your hands and knees."

I got up on all fours in a doggie position while Karen jacked his rod with blue goo. Zack crawled around me, pushed my panties to the side and began his insertion. Between the plug and the lube, he went in so easy. He was at full thrust quite quickly and I was rocking back and forth in matching harmony. We were all groaning, even Karen. She moved near my ear and whispered.

"I understand that true sissies will cum from just being fucked. Let's see if you're a real sissy or just a cross dresser."

"Karen, put your hand on lower belly to see if you can feel him thrusting me?"

"Oh yeah, I can. He is so deep in you. Geez, I need to do this at home. You OK back there Zack?"

"So tight, it's so tight. I've never had it so tight."

"Good, Brie likes to hear that. Her balls are tensing up. Pound that tight little hole Zack, pound it. Brie, let it go, I can see your balls moving sissy. You're going to cum without being touched. Release those balls just because Zack is ripping your ass a part. Release Brie."

In the video screen in my head, I am watching my ultimate favorite WEBM. The one where the Trap is down low on his knees and taking it like a pro while his bull is giving it so good. I'm the Trap on the bed.

"Karen, stop with the dirty talk. I can't hold out. It's too much. Zack, keep going baby, don't stop. Wreck my panties and my ass. It's all for you. Oh shit, Karen, I can't stop it."

With that, Karen put the towel underneath me to catch my load. It's a good thing she did. My panties were everywhere except where they were supposed to be. There was nothing I could do to stop it. I'm not sure how many squirts I released, but I finally got a score for the day. Meanwhile, my lover was still going at my ass with no signs of slowing up. Praise the Lord for lube. I knew I would feel this in the morning, but right now it feels good.

"Brie, I knew you were a true sissy. You came without any touching. Zack, are you getting close to delivering back there? This sissy needs that cream pie to complete her transformation."

I knew exactly when his first burst came because he jammed me down on my belly and began shaking. I felt several more violet thrusts as he emptied himself deep into me. No matter what anyone says, you can feel it. You know it's in there. Zack and I laid there to catch our breath. Karen went into Phase 2.

"Brie, wipe that the lube off his dick with this towel and suck that limp dick and get to the bathroom. It doesn't stay in there for long."

Zack fell back onto the bed exhausted. I actually kissed his chest as a sign of approval as I wiped his cock clean and then went down on his spent cock. Before I left the bed, I whispered into Zack's ear.

"If you have it in you, she really needs it. Anything you can muster. I'm going to be in the bathroom for a few minutes."

Then I headed to the bathroom and let gravity to do its thing. I think the score is 1 -- 4 now, but my one win is worth a lot. Zack has a perfect size tool and he knows how to use it. I wonder why his girlfriend broke up with him?

Wait, I did cum from just being fucked. I think I'll score that as a win. 2 -- 4 to this point.

I was cleaning myself up when I noticed noises coming from my bedroom. It sounds like sex to me and I have no problem with that. I had to know if Karen was on her back or on all fours. I entered my bedroom and found a little surprise. It was a position I did not know of. Zack was in a sitting position with Karen on top of his lap, facing him with her arms around his neck.

"Nice position. What is this one called?"

"Cowgirl. Forward Cowgirl, I think. A sissy can do it this way. Thank you by the way."

"You're welcome. But, can you get pregnant right now? He produces a lot of swimmers. I mean a lot. Maybe he should finish in my mouth?"

"Way to spoil the mood, but you're right. Here, trade places with me. You should still be stretched and he is very wet. You OK with that Zack?"

Zack responded by grabbing Karen's shoulders and forcing her down on his cock. His grunts and facial expressions let it be known that he came inside of Karen. He bounced her up and down several times. Nothing good is going to come of this.

"Damn it, Zack. I could get pregnant. What were you thinking?"

"I was thinking that I've wanted to fuck you for over a year and here we were. Sorry, but there is no way I was gong to pull out. Brie, I apologize to you as well."

Karen slipped out of his grip and fell downwards on his belly. The next thing I knew she had his limp dick in her mouth.

"Karen, what the hell? That's my thing. Get off of him."

"I taught you the Cowgirl and you taught me about soft dicks. We're even. Put that on your precious score card. Zack, are you spending the night here?"

"No, but if you give me ten more minutes, I can finish you off in the doggie fashion that Brie likes so much. Are you up for that? I'm sure Brie would like that."

"This is messed up. Brie, you set this up."

"Sorry, but I knew you needed some dick. I didn't mean for him to cum inside of you. Do you want me to suck him hard? I do like to watch people take it doggie."

"Well, because you like certain things and we're all naked, let's do it. I'm not explaining this to Suzie."

"Zack and I had sex. End of story. Now let me get this boy hard for you. We all know I like that doggie thing but I won't complain if he slips out and re-enters through the wrong door."

Karen was already getting into position and Zack was already responding. What a Saturday. Where is my score card?

End Pizza delivery with a twist 13