Trailer Trash Tycoon Ch. 02


It was the start of the month and thin little brunette Jasmine had just finished ‘paying her rent’. I thought her pigtails were very cute, especially with her young-looking face. I’d been tempted to use them as handles during the blowjob she gave me but behaved myself and let her do things at her own pace. Her pussy was nicely tight, even though she’d given birth five months before. As we were drying each other after a shower, the doorbell rang.

I wrapped a towel around my waist and went to the door. When I opened it, I saw a redheaded woman with large breasts who looked like she was about 30. She had some small wrinkles on her face but was still pretty. A much younger redhead stood beside her. The older one had the beginning of a ‘baby bump’ and held up one of my business cards. “Can you help us find this place?”

I recognized my card immediately by the red lips kissing a rounded cross that looked a little like a dick and a pair of balls.

“You’re looking for the Slutty Sinner’s Salvation Center? You’re pregnant?”

She looked very ashamed. “My daughter is three months pregnant, and I’m at six months. Do you know where the Center is?”

I smiled and told them, “You found it. Come in and have a seat.” I noticed the younger one was staring at my bare chest. “Would you like something to eat or drink?” Both were hungry and I gave them sandwiches and glasses of milk.

Jasmine walked out to the kitchen slowly, with both hands on the wall. “Have you seen my glasses? Without them or my contacts, I’m blind as a bat.” She was only wearing panties and a towel on her hair. Her small tits were fully exposed.

I took a step toward her and said, “I think they’re in the bedroom.” As Jasmine was feeling her way around, her hand caught the edge of my towel and pulled, leaving me naked in front of the two strangers. “AIEE! Back in a minute!”

I ran for the bedroom and found Jasmine’s glasses next to my alarm clock. I quickly threw on sweatpants and a tank top. When I got back to the kitchen, I saw the young girl had helped Jasmine to a chair and they were talking. The mom asked, “Is this some kind of weird sex brothel? Is that guy dangerous?”

“Leo? No! Leo’s a big puppy dog! He helps a lot of pregnant girls. He’s been great to me! Give him a chance.”

I handed the glasses to her. “See! Leo’s a life saver!” She moved to kiss me before putting the glasses on and tried to make out with a jacket hanging on a hook.

The rest of us laughed loudly. She asked, “What? What’s so funny?” She put her glasses on and laughed along with us.

She went to the bedroom to finish dressing, then left.

I gave the two redheads my usual speech. “Don’t tell me any more about yourselves yet. If I know a girl’s name and hear about her, I might have to tell the police where she is. If I know a girl is under 18, she can’t stay here and I can’t help her.” I paused.

“If I ask your name and age and you don’t have any ID, I just need to take your word for it, right? If you tell me your name is Martha Washington and you’re 300, I have to believe you until I see something that says otherwise.”

The younger one smiled. “I guess.”

“Just take a minute to think, then tell me your names and ages, please.”

The mom looked at a magazine with a bunch of fruit on the front cover. “I’m Amanda Apricot, and I’m 29. My daughter Cherry is 18.”

I quickly did the math and joked, “That really must have hurt?”


“Giving birth when you were only eleven.”

We all shared a laugh, then I asked; “Do you need to see a doctor or anything major today?”

“No. We need a place to stay, but we don’t have any money. And maybe some clothes? These are all we have.”

I explained, “I’ll be happy to help you two, but you can probably guess I expect something in return. You’re pretty ladies and I’d like to spend some time in bed with you.”

‘Cherry’ nodded. “Okay.”

‘Amanda’ said, “You want us to have sex with you to stay here? I’ll do it, but I don’t want my daughter screwing you. She’s only… she’s only 18.”

I said, “If she’s already pregnant, she’s old enough for sex if it doesn’t hurt her, right?”

I held Cherry’s hand and asked, “Do you think kissing me and sucking my dick will hurt you?” She shook her head. “I understand that you don’t know me and you’re nervous. Jasmine got me off twice just before you knocked on my door. Did it look like I hurt her or that she was even sad?”

“No, she was smiling. And she said you’re great at… um… some stuff.” She blushed vigorously.

I asked, “Do you drink or smoke, any drugs?”

The mother ‘Amanda’ said, “I smoke and I caught her once, but she’s not allowed. I quit drinking when I found out I was pregnant. No drugs in a long time.”

“At least that’s good. I don’t mind if you smoke in the living room, just open a couple windows. Do you need anything else?”

“Clothes, please? We’ve been wearing these for three days.”

“Let me make a couple calls.”

A few minutes later I told gaziantep eskort them, “Amanda, Melissa is coming over soon. She’ll take you to get some clothes and give you some advice about how things work here. In a little while, Jasmine will come back and do the same for Cherry. Once you have more to wear, we’ll get a shower and watch a movie before bed.”

When Melissa left with Amanda, Cherry told me a lot of things she didn’t want to say in front of her mother.

“I don’t want Mom to be mad, but I REALLY want a cigarette! Please?”

“Sure. I keep some in the bathroom closet. You can turn on the fan and smoke in there and your mom won’t see.”

“And, um…”


“Will I have to do sex with you in front of Mom? That would be SO embarrassing!”

“It’s a two-bedroom house. One of you can stay with me, and the other one in the spare room. But I want you to watch each other at least a few times. I’m not gonna pass up the chance to screw you in front of your mom and look at you as I do it with her.”

“Um… I… I guess I could do it once or twice, maybe. And Leo, I hope it’s okay if I just have sex with you. I really hate doing blowjobs. If I don’t have to suck you, we can fuck two or three times a day. I’ve been super horny since I got knocked up.” Her face slowly turned red as a beet.

“Sounds great! I’ll go get you cigarettes.”

When I came back I sat next to her on the sofa and said, “Go ahead and sit in my lap while you smoke. I’d like to play with your chest.”

My cock liked the pressure in my lap as she sat on me, and it began to swell. She lit up and took three rapid puffs. “Aaaah! I haven’t had one since yesterday. Thanks!”

As I fondled them gently, I said, “You have some nice little boobs. The baby should make them grow quite a bit. I love it when a girl is close to giving birth and she starts giving milk. That won’t happen to you for about half a year, though. I can’t wait.”

Her mother returned earlier than I expected and angrily said, “You’re smoking! And letting him…”

I interrupted, “If she’s 18, she can make her own choices. She is 18, right?”

“Um… yes.”

“I don’t want either of you smoking a lot ’cause it’s bad for your babies, but a few a day shouldn’t hurt much. If she wants to sit in my lap, that’s up to her.” After that, Cherry started sitting in my lap any time we were with her mother. I thought she mainly did it to annoy her.

Jasmine knocked and walked in. “Hi, Cherry. Let’s go get you some clothes.”

When they left I told Amanda, “Come sit in my lap and have a smoke.”

She asked, “We can do it quick while she’s away, if you want?”

“You read my mind! Let’s go in my bedroom, it’ll be a lot more comfortable.”

She followed me and said, “I hate giving head, but you can do my ass sometimes. I kind of like anal.”

“Sure! Sounds good to me!”

“And, um… can you do me from behind most of the time? I like the feel of having a dick in me, but I like women a lot better.”

“No problem. Lean over the bed and let me pull your panties down.” I played with her ass cheeks and lubed up her butt crack.

She said, “I talked with Melissa and I like her. Maybe we can work something out?”

Instead of inserting my cock, I sat next to her and asked, “What were you thinking of?”

“Melissa is sad and lonely after her ex-girlfriend moved out. How about I do anal or fuck you sometimes but live with her?”

“How about once a week and mostly anal?”


“And I get to do it with your kid watching us three times, and I get to screw her in front of you, too?”

“Well… that would be SO EMBARASSING! But… I guess if we have to.”

“We have a deal, then. I LOVE anal! I’ll try to take it slow and easy to start. I think it will go better if you put a pillow under your belly, to angle your butt upward.”

She moved a pillow as I stood and moved behind her. I stroked my dick a few times to get it fully hard again, then slowly pushed into her tight and slippery anus. She asked, “Ungh! Slow please? I like it after the first minute or so, but it hurts at the beginning.”

“I’ll try and take it easy. Let’s give it some more lube too.” I squirted a little more onto my shaft and pulled back, then entered fully but very slowly.

“Oooh! That’s not so bad.”

“Good. Rub your pussy, that will help. This should help too.” I reached to the remote and turned on a webcam channel. Slutty Asian girl Jee was sitting on her bed as she slid a small red dildo into her pussy.

After a few more strokes I sped up and leaned forward, so I could hold Amanda’s big tits as I stuffed her butt. She stared at the screen as she rubbed herself. Before long, she started moaning in pleasure instead of discomfort. “Mmmmm. Yeah. I like it in my ass when it doesn’t hurt.”

I matched the speed of my thrusting to the dildo Jade was sliding in and out of herself. I slowly increased the pace as Jade did. I pumped a load into ‘Amanda’s eskort gaziantep ass just before the Jade on the screen got herself off. “Ohhh! So good!”

I was a little surprised she had an orgasm too. I rolled off her, then played with her curly red hair as I rested. She said, “I don’t mind doing that once a week, if I can see a pretty girl while we do it.”

“I think you’ll like it even better if you’re on top of Melissa, with her licking you.”

“Mmmmm! That sounds great! I better clean up before Cindy… before Cherry comes back.”

“Sure. I’ll see you at Melissa’s place in a few days.”

After supper I played with Cherry’s long red pigtails as she sat in my lap smoking a cigarette. She said, “I have a sexy idea. There’s an old saying that ‘if she smokes, she pokes’. I’m super horny lately and only smoke about five a day. How about any time you see me smoke, you can poke your big dick in me?”

“EXCELLENT idea! Sit up a second.” I slid her skirt up and moved her panties to the side, then guided my rod into her tight pussy as she sat back down.

She moaned, “Ooooh! So nice! Just hold still a minute! I want to enjoy just having it in me before we start.”

“Yeah! Another great idea!” I savored the hot wet pressure of her vaginal flesh squeezing me. I played with her little boobs and stared at her lips while she finished her cigarette, then started lifting her up and down on my rod. I was close to finishing when there was a knock at the door. I shouted, “JUST A MINUTE!”

Much more quietly, I groaned and said, “Yeah, Cherry! So good! UNGH! Yes!”

Amanda walked in and said, “I forgot my cigarettes…” The shock of seeing me fuck her daughter stunned her into silence. I stared at the shape of her big tits through her blouse as I lifted Cherry up and down.

Cherry cried out in surprise, “Eeeh! Mom!”

I exploded into her hot little pussy. “YEAH, CHERRY! URRRR!” She jumped off me and pulled her skirt down, as I sprayed most of my spunk onto the floor.

The two stared at each other silently as I panted. Once I caught my breath, I said, “That’s once for Cherry. She only needs to let you watch two more times.”

I saw Amanda had a hand between her legs and looked quite excited. She asked, “Can you go again? So… so I can get one out of the way too?”

Before I answered, there was another knock at the door. I hoped to get the usual reaction when I loudly said, “Just a minute!”

I put my pants on and whispered to Amanda and Cherry, “I’ll bring Cherry over to Melissa’s place tomorrow night. See you then.”

As Amanda opened the door and walked out I saw a vision of loveliness at my door, two beautiful little blondes who looked like clones of each other. Each was slightly under five feet tall and held one of my cards.

I motioned toward the kitchen and told them, “Come in. Please.”

At the same time, in about half a second, they asked, “Can you help us?” “Is this the Salvation Center?”

“It is. Please have a seat. If you’re pregnant and need help, I’m all ears.”

I could hardly understand their extremely rapid speech as they talked over each other. “Well, we’re not pregnant, or probably not.” “Can you tell us where to go if we’re not pregnant?”

“Cherry, could you go watch TV in my bedroom for a while? I think they might want to talk to me privately.” She did as I asked, then I continued, “Ladies, one at a time, please.” I pointed at the one on the right. “You first.”

“We got in big trouble and Mom kicked us out of the house. With us changing into women and homones and all that, it’s hard to be good sometimes. We got grounded for a month when she caught us smoking. Then we got grounded for another month when she caught us licking each other. When she caught me sucking her boyfriend’s dick and him playing with my twin’s pussy, Mom went crazy slapping us and shouting. She kicked us out, and we don’t have any place to go.”

I was amazed she could get out so many words in so little time. I paused a moment to process it all, then pointed to her sister. “Your turn. Anything else?”

“We only started our Freshman year two months ago, and now we don’t have anyplace to live. How could she kick us out when we’re only….”

I quickly held up my hand and cut her off, “Whoa! Whoa! Whoa! Before you say anymore, I need to tell you a few things. Please listen until the end, okay?”

They nodded and I gave them my user boilerplate speech. “If I know a girl’s name and hear about her, I might need to tell the police where she is. If I know a girl is under 18, she can’t stay here and I can’t help her.” I paused a few seconds.

“If I ask your name and age and you don’t have any ID, I just need to take your word for it, right? If you tell me your name is Martha Washington and you’re 300, I need to believe you until I see something that says otherwise.” They nodded and smiled.

“Please take a little while to think, then tell me your names and ages.”

They looked gaziantep bayan eskort at the costume jewelry rings on their fingers and I followed their eyes. The cheap rings were obviously plastic with gold paint and a few fake stones.

The one on the left said, “I’m Goldie and my sister is Gem. We’re um… We’re 18.”

I asked, “So when she said you’re Freshmen, she meant college Freshmen, right?”

“Um… ah, yeah.” Their size and the shape of their faces hinted otherwise, but I wasn’t going to dig any deeper.

“Good. I think the first thing we need to do is find out if you’re really pregnant or not. When was the last time you had sex?”

‘Gem’ said, “Last week. I sucked him off and he fingered me a while. I didn’t come, but I don’t think you need to cum to get pregnant, right?”

“No, but you need a dick in you. When was the last time you two had INTERCOURSE?”

They blushed and Goldie said, “Ah, never. We’re virgins but we want to try it.”

I declared, “Okay, so there’s no way you’re pregnant. I usually only help pregnant girls…”

Goldie cut me off, “Please! We love doing blowjobs! We don’t need much room. We can share a bed. We’ll suck you off any time you want! Five times a day, even! Please?”

Gem jumped in, “We love sucking cock! We like girls a lot too. If you have a girlfriend, we can do stuff with her! And you can fuck us. Please?”

“I was about to say, I only help pregnant women, but I can make an exception for some pretty little ladies like you.”

They both sighed in relief. I asked, “Is there anything urgent you need today? Do you need to see a doctor, get medicine, or anything like that?”

They nervously looked at each other. Gem asked, “Could we get cigarettes, please?”

“Sure. I’ll round everybody up, and we’ll go on a shopping trip. Do you have any money?”

They sadly shook their heads. I reached in my pocket and handed each of them a hundred-dollar bill. “I think you dropped these on the floor.”

“Thanks!” “Thank you so much!”

I asked, “What kind of cigarettes do you like? I don’t think the store cashiers will believe either of you is 21, or even 18.”

Gem giggled and said, “Menthols, long ones like 100’s.”

Her sister flirtatiously commented, “Yeah, we like sucking on the long ones.”

“Hahaha! Wait here with Cherry, while I go see if any of the other girls need to go to the store.”

Only Cherry and the twins needed anything, so my minibus was mostly empty. As we walked through the grocery store parking lot, I slipped Cherry a hundred bucks. I walked slower than usual, following the girls so I could watch their cute butts while they browsed the aisles. It wasn’t even Halloween yet, but the store already had Christmas items on the shelves. I was annoyed they were trying so hard to push holiday sales, but grabbed a couple boxes of candy canes. I LOVED seeing pretty girls suck things, even things that weren’t attached to my body. As we approached the registers at the end of our grocery trip, I saw some extremely long cigarettes in the display, menthol 164’s. I got a carton each for Cherry, Gem, and Goldie. I felt my underwear slowly tighten as I anticipated bedtime.

After supper and an extremely crowded shower with all three, I ecstatically discovered they made an excellent sex team. One of the beautiful young blondes licked and sucked my cock while the others watched and I played with their little breasts. Pretty redhead Cherry was more than happy to ride me reverse cowgirl style as a blonde rode my mouth with her delicious and tiny pussy. Only seconds after I climaxed and she moved off me, a blonde was sucking my cum out of Cherry while the other licked me clean. It was AMAZING, some of the best sex I’d ever had!

We cuddled in bed watching the news, then Cherry asked if we could try doggy style. I was beyond happy to do her from behind as we watched the twins sixty-nine each other into unconsciousness. I spooned behind Cherry and played with one of her little boobs as she lit up one of the extremely long white cigarettes. Its size made her seem even smaller. Seeing her cheeks and mouth as she sucked on it reminded me of the wonderful blowjob I’d gotten when we started, and watching the stream of white leave her lips made me think of the little blonde licking up my jizz.

I gently stroked her hair and thought about the future. Cherry wouldn’t give birth for five or six months, and the twins weren’t even pregnant. I knew Cherry would be with me about half a year, and I hoped the pair of pretty blondes would keep warming my bed a long time. Eight of my ten trailers had people living in them, and Cherry’s mother would move into the last decent one after she had her baby.

I checked my bank accounts on my phone and saw they held a bit over two million, as I expected. I checked my investments and saw the twelve million I’d put in had grown to almost sixteen. I decided I could afford some expansion and upgrades.

The next morning, after kissing Cherry as I screwed her missionary style, the four of us had a nice breakfast. I told the girls to stay home, I needed to take care of some business. Before I left, Goldie and her sister gave me a glorious smoky blowjob as I stood in the living room. Watching them alternate between licking my cock and blowing smoke on it was very arousing. I was glad they liked to swallow.

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