Chapter 49: Paybacks And Fantasies (And Guilt)

I opened my apartment door and let Megan in. She was wearing a long winter coat that went almost to her ankles, and she had a bag of cleaning supplies in her hand.

“Good afternoon, Sir,” she said. “I’m here to do your cleaning, as usual.”

She pushed past me into the livingroom, and took her coat off. Underneath it, she was wearing the sexy maid costume that she and Cheryl had purchased for what I like to call my dream weekend. It consisted of a very short and very flared black skirt with a white ruffle and a black corset-like top that was very low-cut and very tight. Megan’s curves stretched that outfit to its absolute limits. Her boobs looked like they might explode out of their prison at any moment, and the bottom of her ass cheeks showed under the skirt. A tiny white apron finished the look off. The first time she had worn this costume for me, she’d had on a pair of black stockings and some high-heeled shoes, but this time she’d gone with a pair of black boots. They reached almost to her knees, and had heels that gave her ass even more shape than it usually had. She was also wearing a ton of makeup: lipstick, eyeshadow, mascara, perfume.

“Wow,” I said. “What’s with the outfit? You usually work in jeans and a t-shirt.”

She blushed. “I know, Sir. But with it being Christmas and all, and you being one of my favourite customers, I thought maybe I’d dress up a bit. You know. Give you something to look at while I clean. You don’t mind, do you?”

“Not at all,” I said. “But I’m glad my girlfriend isn’t here today. She might not want you showing me this much skin.”

Megan suppressed a giggle. She knew that this was part of the game.

“That’s probably true, Sir. But what that cute little girlfriend of yours doesn’t know can’t hurt you, right? Anyway, you’re not paying me to stand around. I’d better get to work.”

For the next couple of hours, Megan cleaned my apartment. I felt kind of guilty, making her do that. But on the other hand, this was her payback for the time I had cleaned up her place, and my apartment was nowhere near as bad as the mess I had cleaned up for her. She washed my bedding, and put it back on my bed again, and she cleaned the toilet and sink and bathtub and bathroom floor, and the kitchen counter and stovetop and kitchen floor, and she washed the dishes that were in my sink, and then she dusted and vacuumed the entire place.

I watched her - I couldn’t have taken my eyes off her if I had tried - but I didn’t touch her. This was part of my plan. Most of the time I just sat on the couch, though sometimes I got up to see what she was doing. She came close to me a few times, and stuck her tits or ass practically into my face, reaching over me to dust or bending in front of me to vacuum, and I certainly thought about just grabbing some ass or even pulling her little thong to one side and sliding a finger inside her pussy. But I didn’t do it. I just watched her work, and enjoyed the show that she was putting on for me. And yes, I did take a couple of pictures, so that I could show Cheryl later.

When Megan was done the cleaning, she came and perched on the arm of the couch. I noticed that she had re-applied her makeup. I also noticed that the position she was sitting in gave me a great view up her tiny skirt to her barely-covered pussy.

“I’m finished the cleaning, Sir,” she said. “That is, unless...”

“Yes?”

“Well, I’m finished, unless you want me to do anything else for you today.”

I tried to look puzzled.

“I’m sorry. I can’t think of anything else I need done.”

“Are you sure, Sir? I’m just asking because ... well ... I noticed you staring at me as I worked. And I was just thinking. It’s almost Christmas, Sir, and I could use some extra cash, and so if you wanted me to, I could ... umm ... take care of any needs that might have come up. Like this need, maybe, Sir. It seems to have come up quite a lot.”

As she said that, she leaned down and began to caress the bulge that my cock was making in my jeans.

“Excuse me?” I said. “I have a girlfriend!”

“I know that,” she replied. “But you were clearly enjoying the show today, and you haven’t tried to take my hand off your cock, so I’m thinking that you might be open to some of the extra services that I would be willing to provide for you. I mean, no offense to your girlfriend or anything. I’m sure she’s a great little fuck, when she wants to be, and I bet she sucks you off sometimes, too. She might even let you fuck her up the ass once in a while. But I know that there are times when she doesn’t meet your needs. I’ve seen the crusty panties under the side of your bed, and I know that means you jacked off in them. Besides, all guys have fantasies that are too taboo for them to even think of telling their girlfriends about. And all guys like to try a little strange pussy sometimes.

“So what about you, Sir? What are your raunchy, nasty, secret fantasies? What is that you can’t bring yourself to ask your girlfriend to do for you? Do you want to put me over your knee and spank me until my cheeks are nice and red, and then fuck my tight little asshole? Do you want to grab me by the hair and force me to take your cock so far into my mouth that I gag on it and my eyes start to water? I brought some toys along, too, in case you want to use them. You can tie me down to the bed. Or you can cuff my hands behind my back right here. You can make me be your little toilet slave. I’ll do anything you want. All you have to do is ask me. Or order me. Or just take what you want from me.”

My mouth had gone dry. I’d planned this, sort of. I hadn’t scripted it, though, and what she was offering was much more, and much more explicit, than we had talked about.

“What will this cost me?” I asked her.

“Well, I just want to make a little bit more cash for Christmas,” she said. “So if you pay me maybe double the usual pay for the cleaning job as kind of a holiday bonus, then I can be totally yours all afternoon.”

I didn’t answer, or at least I didn’t answer with words. Instead, I took hold of her wrist and pulled her - gently - so that she was lying on the couch, her head down in the cushions, her butt across my lap, and her feet sticking out over the arm she had been sitting on. I kept my left hand wrapped around her wrist, holding her one arm behind her back, and used my right hand to lift up her tiny black skirt.

Megan has a magnificent ass. She really does. And having it across over my knee, bare except for a tiny thong, and with permission to spank it ... oh yeah. I was going to do that. But first I was going to feel it up a bit. She gasped when I grabbed her. Maybe I was bit rougher than she was expecting. I squeezed both of her cheeks, and gave her a couple of pinches. Then I raised my hand and brought it down. That made her jump. I slapped her a few more times, enough that her butt turned a nice shade of pink. I reached between her legs, pulled her thong to one side, and slipped a finger along her slit.

“Fuck,” I told her. “You’re so wet. You must be a total slut, to get this turned on this fast.”

She moaned.

I found her clit with my finger, and began to rub it, lightly. She arched her hips to try to get me to apply more pressure. I watched her closely. I’d fooled around enough with Megan in the past few weeks to know when she was getting close to coming. I took her almost to the brink ... and then I stopped, and pulled my hand away.

“Not so fast, slut,” I told her. “You’re going to have to earn that.”

I slapped her ass a few more times, then let go of her arm and helped her to stand up. Then I spread my legs and pointed at the floor between them.

“Get down there, slut, and show me what your mouth is good for.”

Megan didn’t hesitate even for a moment. She dropped to her knees in front of me and unbuttoned and unzipped my pants, and then unbuttoned my boxers and pulled out my cock. It was already hard, and oozing precum. She licked it clean and then took it into her mouth. Megan once asked me who was the better cocksucker between her and Cheryl. I declined to answer, mostly because it seemed the right thing to do, but honestly I don’t know if I could have answered. They’re different from each other, but they both have skill, and God knows they’ve both had practice, and they both give a damn good blowjob. So I let Megan do her thing for a few minutes. She knows how to get a guy going, and she knows specifically how to get me going.

But I didn’t want just a blowjob. You see, Cheryl and I had been talking, one morning a couple of weeks ago. I’d gotten a tad more aggressive than I usually do when she sucks me off, and had ended up making her gag a bit with my cock. She’d said it was ok, because it showed how excited I was, but she’d also told me about a previous boyfriend who used to try to make her gag on his cock, repeatedly, whenever she sucked him off. I’d been thinking about that ever since, and I’d decided it might be fun to try it, just once, and since Megan had promised me any kind of sex I wanted, I had decided that this was the time.

I took hold of Megan’s head, and pushed it down, until I felt my cock pushing against the back of her mouth. She gagged, and tried to pull back, but I didn’t let her. I kept my cock buried deep in her mouth as she gagged a couple more times, and then let go of her head. She pulled off, took a big gulp of air, and took me back inside her mouth. So I did it again.

And yeah, it was kind of fun. I did like the control aspect. It was cool to feel her struggling a bit, and it was hot to see her makeup getting streaky and knowing that I’d caused that by making her eyes water. But I had to admit that ultimately I would get a far better blowjob if I let Megan move her head and use her lips and tongue, instead of just forcing her to hold my cock at the back of her throat. So I released her head and let her please me, at least until I felt that tingling feeling beginning to rise. Then I grabbed her head again, and pushed my cock deep in her mouth, and held it there, and pumped what felt like a litre of come out of my cock.

It must have felt like a litre of come to Megan, too, because she couldn’t hold it all, and when I released the death grip I had on her head and she pulled pack, my cock and pubic hair were covered in frothy white goo. I let her catch her breath while I made her pose for a picture.

She already knew what I was going to make her do next.

“You’re the fucking cleaning girl, right?” She nodded. “So do your job. Clean up that mess you just made.”

I didn’t need to tell her that I didn’t mean for her to use a cloth. She bent her head back down into my lap and licked and sucked all of my come - and all of her drool - off me. By the time she finished getting me cleaned up, I was well on my way to getting hard again. I pushed her away, and stood up, pulling her to her feet with me, and told her to take off her boots. I loved how she looked in them, but they would get in the way later. When she straightened back up after doing that, I spun her around, so her back was to me, and removed the wrist cuffs from the bag she’d brought with her. I attached the velcro straps around her arms, and then clipped the cuffs together behind her back. Then I positioned her on the couch, on her knees, her legs spread apart a bit, with her feet sticking off the couch and her upper body supported by the cushions. That left both her pussy and her ass totally exposed and vulnerable, covered only by the thin fabric of her black thong.

I left her there for a minute or two while I got undressed. And yes, I did take another picture. Cheryl would want to see these, and I would enjoy masturbating to them later. Megan would likely do the same. I grabbed the bottle of lube that Megan had brought from her bag as well, and set that on the couch where I could reach it easily when I wanted it. And then I leaned in, pulled her thong to one side, and buried my face in her cunt.

I think that she started coming the minute my tongue connected with her clit. She squirmed and moaned and bucked her hips back towards me. She was incredibly turned on from the combination of sucking me off and having her hands cuffed - Megan loves being restrained - and likely still some of the residual effects of showing off for me while she was cleaning.

“Fuuuuck,” she moaned, as she came down from the high. “That was amazing.”

I straightened up and stood behind her, putting my hands on her hips, and positioned my cock at the entrance of her cunt. I knew she was wet, so I didn’t try to go slow - I just shoved it in in one hard thrust. Megan grunted as I bottomed out. I reached up and grabbed the cuffs that were holding her arms behind her back, and used that to get additional leverage as I fucked her.

I could have come in Megan’s cunt. I could have. But I didn’t. I had other things I wanted to do to Megan before I was done with her. I reached for the bottle of lube, and dribbled a bit on her asshole. Then, while I kept fucking her, I slipped a finger up inside her butt. The couple of times I’ve had the chance to do this, I’ve really enjoyed feeling my cock moving around inside a girl’s pussy from inside her butt. I pulled my finger out, dribbled a bit more lube on Megan’s butthole, and slid my finger back in again. I wanted to get her nice and slippery, and relax her a bit, if I could. I pulled my finger out again, and let a bit more lube drip onto her.

But this time I didn’t put my finger back in her butthole. This time, I put my cock in her butthole.

She tensed a bit as she felt the head of my cock pressing against her. Again, she’d known what was coming - and if she hadn’t known ahead of time, she would have figured it out pretty quickly when I started to lube her up. She took a deep breath, and I pushed a bit more, and the head slid inside. I let her get used to the intrusion for a few seconds, and then I pushed it the rest of the way in.

Megan had been an anal virgin at the time that the two of us first had sex. She’d been hanging on to that virginity (Cheryl calls it her ‘prune’) for a long time, and yet she had been willing to give it to me as part of what I call the dream weekend. Cheryl had helped coach her through that first anal penetration, and the next day both girls had used a strap-on to fuck each other’s assholes.