Chapter 1

Her name was Kathy. 33 years old, chubby, dirty-blond hair. I met Kathy when I visited the restaurant where she worked as a part-time waitress. I’m a relatively well-off guy, and I dress like it. Kathy was attracted to my looks, my self-confidence, my deep voice. She flirted with me, we exchanged numbers, and that evening I found myself taking her out to a nice dinner, then going back to her place for sex.

It’s particularly nice to bed a woman when she is really into it, excited by the novelty of a new man, excited by dating above her social class. Her clothes came off so eagerly, there was real enthusiasm in her blow job, and she was so wet when I moved onto her plush, plump body and sank into her fiery depths. That first night, I lost count of her orgasms, and I came a couple times myself, in her mouth and in her pussy. Cuddling post-sex was nice, but then she reluctantly asked me to go home, because she’d find it awkward in the morning, to explain a man in her bed to her daughter.

Ah, her daughter. Kathy and I became a steady thing, so I eventually met her daughter, Kaitlyn. 14 years old, chubby like her mom, a freshman at the local high school. She was quiet, a little shy around me. She liked reading books, and she played videogames for hours. She usually stayed in her room, especially when I was over at their apartment.

This went on for some months. Eventually, Kathy and I started seeing less of each other. I started dating a new woman, Susan. Susan was 40 years old, smart, sophisticated, independent. She had a realty business and drove a Mercedes. Our dinner dates were full of intellectual conversation. We liked spending time together, like going around town, even shopping with her was fun. The only catch was that Susan wasn’t particularly sexual. She liked kissing, and she liked it well enough when I went down on her, but intercourse was brief and mechanical, and she had zero interest in my cock going anywhere near her mouth.

So, I still occasionally saw Kathy, basically as a booty call, preceded by dinner.

Then, Kathy’s life took a turn for the worse. She got behind on her rent, and lost her apartment. She scrambled for another place to live, and knowing that I managed some rental properties, she asked me. I fast-tracked Kathy’s application, told my staff to ignore her dismal credit rating. I paid for a moving truck. She and her daughter had a place to live again, a smaller apartment, in my cheapest property. She scraped together her first month’s rent, and I waived the deposit. I was now their landlord.

Everything seemed fine until one month later. I went by their apartment on Saturday morning. Kathy let me in. She was wearing a loose robe, looking like she just rolled out of bed. There was breakfast still on the breakfast table, and the TV was going. Kathy went to the sofa, and I sat in a chair across from her. She turned down the TV and gave me her full attention.

“Your rent was due yesterday, Kathy.” I gave her a serious look.

She nodded. “Yeah. I’m totally going to have it for you. Next week?”

I sighed. “That’s not how this works, Kathy. You’ll need to find the money.”

She looked worried. “I thought ... I thought we had a relationship? I mean, I know I’m not your girlfriend, but ... I do things for you.”

I smiled. “Yes, you do. Are you really comfortable with that? Let’s get this out in the open. Trading sex for rent? I mean, you’ve probably never traded sex for money before.”

She frowned. “I’ve never done that outright, no. But I like you, Mike. And you like me. And sex with you feels good. So ... if you don’t mind getting part of your rent in sex ... I think I’m OK with that.”

I nodded. “So, we make it explicit. You’re willing to become my sex worker.”

She nodded and smiled.

“I’m glad that you’re comfortable with that,” I said. “But you have to admit, I am holding all the cards here. It is, as they say, an imbalanced power relationship. What if I said I wanted more? Like, I wanted to fuck you right out there in public, for everyone to see?”

“You’d get in trouble.”

“OK, what if I asked for ridiculous, kinky stuff? Like, if I wanted to watch you fuck yourself with a cucumber?”

She laughed. “For the rent? Sure, I can do it with a cucumber. As long as you take it out of the fridge for a while, so it’s not too cold.”

“OK, how about anal sex? Anal sex, or you’re out on the street? Your only options would be to do it, or say no and leave.”

Her smile faded. “I ... I guess I would learn to enjoy it.”

“OK. How about Kaitlyn?”

There was a long pause. Kathy looked at me in shock. “You ... you want to have sex with my daughter?”

“Let’s say, not full sex. Hypothetically, just fooling around with her. Like, oral sex.”

“That’s still statutory rape!”

“For fuck’s sake, Kathy. I’m only suggesting that your daughter suck my cock. How old were you when you first gave head?”

She paused and nodded. “OK, I was 15. But Kaitlyn...”

“She’s already fooled around with boys. You told me that. Look, I’ll make a perfectly clear proposal. I presume Kaitlyn’s still a virgin, she stays a virgin. Her panties stay on. I don’t have any interest in fucking her, young teenagers are too inexperienced and usually don’t know how to enjoy fucking yet. So, just oral. All I require is that I come in her mouth.”

Kathy sat there in stunned silence for a minute. “You’re serious.”

“Yes. I don’t care if she gives me a full blow job, or hand job, or talks dirty, or however she does it, or if you help her. All I require is that the head of my cock is inside her mouth when I ejaculate, and that she swallows. Did you swallow, when you were 15?”

She shook her head. “No. I spit. I didn’t swallow until I was 19 and I met Kaitlyn’s father. I was crazy in love with him and I’d do anything.” She stared at me. “Why don’t you just come in my mouth? You like my blow jobs. I swallow for you.”

I shook my head. “Sorry, dear, but to put it bluntly, I can come in your mouth any time. Your 14-year-old daughter is what I’m asking for. I want the kinky thrill of doing it in her innocent young mouth. I want to watch her cute young face as she swallows my load.”

Kathy shook her head. “That is so fucked up! What about her? Does she get a choice?”

“Of course she does. Neither of us is going to force her. If your daughter’s acceptance of the arrangement is your only objection, just ask her. I imagine she’s in her room? You could go explain the situation to her. Tell her it’s for the rent, for having a place to live. See what she says.”

“That’s not my only objection! She’s a human being, Mike. You’re talking about treating her as nothing more than a sex object. I am her mother, I worry about what effect that will have on her. She’s more than just a hole for your perverted fantasies.”

I sighed. “I know that, Kathy. She’s a bright young woman, with a possibly bright future ahead of her. But look at it this way, she won’t have much of a bright future if you’re evicted tomorrow and you’re out on the street.” I paused. “Go ask her.”

Kathy frowned and shook her head, but she got up and went down the hall to Kaitlyn’s room, closing the door behind her. I went to their fridge and helped myself to a beer, then sat back down to wait. In just a few minutes, they both came out of Kaitlyn’s room and came over to sit on the sofa in front of me. Kathy was frowning, but Kaitlyn, still in pajamas, was smiling.

“I’ll do it!” said Kaitlyn.

“Great,” I said. “So ... have you done it before?”

“Not really. I’ve done it for guys with my hand. I’ve seen boys shoot their stuff. It sounds gross to let you do it my mouth, but there are a lot of worse things me or Mom might have to do, to make our rent.”

“I couldn’t talk her out of it,” sighed Kathy.

“That’s an impressively grown-up perspective to take, Kaitlyn,” I said honestly.

“I’m 14! I’m not a kid. And I’m not going to let any random creep do it to me. I know you, Mike. You’ve always treated my Mom really nice. If this weird sex thing is what you want, and we get to stay in this apartment, I’ll do it.”

“Great,” I said, standing up and unzipping my pants. “How about now?”

“Jesus Christ,” muttered Kathy.

“Sure, now,” said Kaitlyn, nodding but looking a little apprehensive.

“Shouldn’t I leave the room for this?” asked Kathy.

“Hell, no,” I said. “Remember, Kathy, your job is to make sure I come in her mouth. Since you’re not volunteering to help her, she’s going to have to try to do it herself this time. She’s never given head before, she might not get me off. You need to watch, and you might need to give advice.”

“Oh, fuck. This is fucked up,” said Kathy, but she didn’t leave.

“So ... what do I do?” asked Kaitlyn.

I moved to stand in front of her. “To start with, just take out my cock. Get familiar with it. When you’re ready, try sucking on it. Be careful not to graze me with your teeth.”

“Oh. OK.” Kaitlyn was a little timid about actually reaching into my boxer shorts to pull out my erect cock, but once it was out, she barely looked at it before popping the head into her mouth.

“Oh my God,” said Kathy, staring intently.

“That’s beautiful,” I said to Kaitlyn. “Good girl. I’m honored to be the first cock in your mouth. Now, try sucking me in and out a bit. Just like how you’ve given hand jobs before, except you’re using your mouth to get me off.”

For a minute, there was just the soft sound of sucking, Kathy and I watching intently as Kaitlyn practiced.

“Kathy,” I said. “Don’t forget. Your job is to make sure I orgasm.”

“How am I supposed to do that?”

“There are lots of things you could do. But you could start by standing here next to me, and kissing me while she sucks.”

“Mike, I don’t feel like kissing you. I’m pretty pissed off about what you’re doing to my daughter.”

“That’s fine. So come give me an angry kiss. Sooner or later, you’re going to have to relax and accept what’s going on. Your resistance is kinda sexy. So, come kiss me.”

Kathy stood up. I pulled her to my side, bringing her face to face with me. She stared into my eyes with a complex blend of emotions, and then we kissed, at first roughly, and then more tenderly. It felt lovely, my tongue in Kathy’s mouth, gently being sucked, as Kaitlyn similarly sucked the head of my cock.

“Tell me you want me to come in her mouth,” I suggested, breaking the kiss.

“I don’t want you to come in her mouth.”

“Yes you do, because it will allow you to stay in your apartment.”

“Well, alright. In that sense, I do want you to come and get this over with.”

“Great, let’s work with that.” I reached my right hand into the loose folds of her loose robe, slipped my hand into the cup of her loose bra, and fondled one of her large, floppy tits, finding a nipple with my fingers. “Let’s try this again. Tell me you want me to come in her mouth. Ask nicely. Make it sexy.”

“Oh, fuck,” muttered Kathy. “Sure. Whatever. You want me to talk dirty about it, that’ll get you off? Do it, Mike.” She paused to kiss me again, deeply. “Go ahead. Pretty please? Fuck my daughter’s innocent little mouth and shoot off in it. Please fill up her young mouth with your cum.”

“That’s good,” I said, reaching down with my left hand to gently run my fingers through Kaitlyn’s dirty-blond hair. I gently grasped her head, encouraging her to take a bit more of my cock, being careful not to press too deep. I didn’t want her gagging. After she was comfortable with it, I pulled her head off my cock. “Kaitlyn, how about you? I’d like to hear you ask for it.”

Kaitlyn looked up at me, saliva running down her chin, breathing a little hard. She was still getting the hang of remembering to breathe with her mouth full. “Ask ... for it?”

“Yes. Smile at me and tell me you want me to come in your mouth.”

“Oh. OK. Um.” She managed a weak smile. “I want you to come in my mouth?”

I smiled. “Not very convincing, but we’ll work on it. Good enough for now.” I pressed myself up to her lips, and she took me in and resumed sucking. I went back to kissing Kathy and rolling her nipple between my fingers.

“Is she doing a good job?” asked Kathy, breaking the kiss to whisper in my ear. “Are you going to give her your tasty cum to drink?”

“I am pretty close,” I replied, “but at this rate, her jaw will probably be sore by the time I finally come. Since this is her first time, I’ll make it easy on her.” I gently pulled my cock back. “Kaitlyn, darling, I’m going to jack off my cock.” I pulled my right hand out of Kathy’s clothes, and used it to stroke my erection, right in front of Kaitlyn’s face. “Just keep your mouth available. When I come, be sure to capture it all, and swallow. Got it?”

“Yeah. OK.” Kaitlyn looked up at my face, then back down to my stroking cock.

“Oh, that looks so hot!” said Kathy, in a convincingly lustful tone of voice. “Masturbate yourself into her mouth!”

Something in the way Kathy said it, pushed me over the edge. I felt my orgasm beginning, my legs got a little weak. I adjusted my stroke, pushed the head up to Kaitlyn’s lips, she took me in and I started ejaculating. I managed to look down at her young face, to see the look of surprise, then a scrunched-up look of distaste, and then finally a serious look of resolve as she sucked and swallowed me down.

“Good girl, Kaitlyn!” I said, as I finally stopped spurting, and pulled my cock back, tucking it into my pants. “You did great!”

“Ewww,” she said.

“So we’re good for the rent?” asked Kathy.

“Yes. And I must say, Kathy, you sure know how to talk dirty.”

“Men are simple. I know how to push your buttons.”

“You do. In fact, you can go ahead and stop worrying about paying rent, ever again. I’ll just drop by from time to time, and the two of you can do whatever it takes, to get me to come in Kaitlyn’s mouth.”

“Time to time?” asked Kathy.

“Yes, not too often. I mean, I’ll still enjoy dinner and sex dates with you on occasion. I promise not to use Kaitlyn’s mouth too often. Say, once a week or so? Kaitlyn, can you handle that?”

“Yeah, I guess so.” She frowned. “It doesn’t taste great. I’m going to go drink some soda pop to get the taste out.”

I saw my proper girlfriend Susan a couple times that week, which satisfied me in every way but sexual. On Thursday, I had a date with Kathy. After dinner, we went back to her place. There was no sign of Kaitlyn. Kathy and I talked for a long time, unpacking our feelings about what we did with her daughter the previous weekend. She told me that Kaitlyn used to have a crush on me, but now had very mixed feelings since I was using her as a sex object. I told Kathy that just before I orgasmed, I started to believe her dirty talk, that maybe she actually was getting off on the situation. She denied it, but not very convincingly. Soon we were in her bedroom undressing, I came once quickly in her mouth, she came once quickly on my fingers, then I fucked her silly through several positions and orgasms before I finally came again. Kathy is pretty loud during sex, and I knew that Kaitlyn could hear us through the walls of their cheap apartment.

On Friday night, an evening with Susan ended back at her place, with her requesting oral sex, getting off, then apologizing for not being in the mood to return the favor, and me going home alone and sexually frustrated.

By the time I showed up at Kathy’s apartment on Saturday morning, I was horny as fuck.

“I assume you’re here for the rent?” said Kathy with a wry smile, as she let me in. “And by rent, I mean my daughter’s mouth.”

“Yes I am.”

Kathy called for her. Kaitlyn came out of her room, wearing the same pajamas as the week before. The pajamas were pale blue, with fluffy white cartoon clouds on them. They were large, to fit on her plump body. Now, most people in this culture would call Kaitlyn a fat girl. But my tastes in women run to the plus size, and by my standards, she wasn’t that big. Attractively curvy, yes. There was weight on her face and her belly, but also sexy weight that sat on her breasts and hips that made her body look much older than 14.

“Mike,” said Kaitlyn as she came over and sat across from me. “We can do the thing, but ... I want to say something first.”

“Sure,” I smiled. Her apprehension was adorable. “Go ahead.”

“Mom says you’re treating me like a sex object. But I wish you would treat me nicer than that. I mean, you can still do the thing in my mouth. But you could at least kiss me and stuff, first. The boys I’ve fooled around with did at least that.”

I smiled. “Sure, darling. I like you. You’re a beautiful young woman. I’d be happy to kiss you or make out with you or anything you’d like. In fact, that would turn me on even more, which would help you accomplish your goal of getting me off.”

“You think I’m beautiful?” she said, quietly, clearly surprised.

“I do, and I am completely honest.”

She smiled softly, and approached me where I sat on the sofa. I took her hands, and drew her to me. Our first kiss was awkward, but eventually she relaxed a bit. I pulled her to me, and she giggled as she moved to sit in my lap, facing me. I don’t know if you’ve ever had a 200+ pound girl sit on your lap, but it’s a major thing; thankfully, the sofa had a lot of give, and her legs on either side of me took some of the weight. We kissed and kissed. Her tongue came out shyly to meet mine. My hands went around her body.

“Do you want to play with my tits?” she asked. “Boys usually like that.”

“I’d love to,” I said. “Does it feel good for you, when boys do that?”

She pulled her pajama top off. She was braless, and even at 14 the weight of her chubby breasts was pulling them downward. She shrugged. “I don’t know. Kinda. I mean, touching my nipples can feel kinda sexy, sometimes.”

I played with her nipples with my fingers, then alternated kisses with nipple sucks, trying various things with my tongue to gauge her reaction. Mostly, she giggled.

“This is fun, but you’re squishing me,” I said.

“Oh! OK, let me suck on you now.”

She got off my lap, and knelt topless on the carpet in front of me. I helped her fish out my nearly-hard cock. She launched right into a clumsy, amateur blowjob. I had to tell her to slow down, to watch out for her teeth. More sucking, less head bobbing.

“I see you’re getting on just fine,” said Kathy, coming into the living room, observing the blowjob in progress.

“I need your help,” I said. “She’s only just learning to suck cock, so it’s going to take more to get me off. Strip naked.”

She stared at me in surprise. “Right here ... in the living room ... in front of my daughter?”

“It’s nothing I haven’t seen before, and if your daughter isn’t already familiar, I’m sure she doesn’t care what naked adult women look like. Strip, then sit in that chair across from us.”

“OK. Fine.” She removed her robe, then her bra and panties, then she sat her pleasantly plump naked body down facing us.

“Spread your legs,” I instructed. “Touch yourself, as you talk dirty about what we’re doing.”

“You kinky fucker,” she said. She spread her legs. “You want to watch me masturbate while my daughter sucks your cock?”

“Exactly. Remember, I like to hear you asking and encouraging me to come in her mouth.”

“Yeah, yeah, I remember. This is still fucked up.” She sighed, then I saw her hands start moving between her legs. “I see you already got her top off. Did you enjoy playing with her cute little teenage tits?”

“I did, and they aren’t that little. She offered them to me, and I wasn’t going to turn her down. I tried sucking her nipples, but it didn’t do much for her. Not like you, Kathy, you nipple slut.”

“You’re damn right I’m a nipple slut,” she said, using her free hand to roll one of her own nipples between her fingers. “How does her sweet little mouth feel on your cock?”

I put one hand on Kaitlyn’s head, gently using it to speed up her sucking a bit. “It feels great. She’s got potential. She could grow up to be a champion cocksucker, like you.”

“Good.” Kathy’s hand was moving a little quicker now, between her legs. “I ... I really, really want you to bust your nut in her mouth, and give her a big mouthful of sperm to swallow.”

“Your dirty-talking game is strong,” I said. “My girlfriend left me high and dry last night, so my balls are probably really full right now.”