Time with a Mature Stripper Ch. 02

I woke up because my cock was getting stroked. I opened my eyes and saw that it was morning; I looked next to me and Stephanie was looking at me. She was propped up on her left elbow, and her right hand was under the covers slowly stroking me to full hardness. I had met Stephanie last night at a crummy little strip club. She's a dancer there under the name "Midnight". Stephanie had caught my eye at the strip club because she had easily been the oldest one dancing there. To me, she just looked hotter than all of the younger girls performing. Big blue eyes, pale skin, dark black hair, giant boobs, a big ass with round, squeezable cheeks, and a black bush above a perfect pussy.

She had approached me for a private dance and I had accepted. I even gave her a $100 tip because she had mentioned that she needed to make a certain amount that night. The private dance had been excellent. Dry humping, tits and pussy waved in my face, but no touching. Worth every penny. After the dance, I had invited her out for breakfast and she joined me. Without asking her to, she blew me in my car and swallowed when I came in her mouth. After we had eaten, we went to my place and I had gone down on her, then fucked her missionary on my couch. We'd then fallen asleep together in my bed. Now she was jerking me off under the blanket.

She smiled at me and said "hope you don't mind being stroked awake. I've been up for a few minutes and I'm horny as hell. Ready to go again?"

I replied "absolutely, and you feel free to wake me up to fool around any time. Especially if you wake me up by getting me hard."

She grinned and flung the covers back as she stopped stroking my dick. It was standing straight up and she got on her knees and straddled me. She used her right hand to guide me into her snatch. As she lowered herself down, she let out a satisfied sigh. Stephanie didn't move at first. I reached up and started squeezing and massaging her enormous, slightly drooping breasts. I gently pinched and pulled her pink nipples until they fully hardened. Once they were, she raised herself up and my dick started to slide in and out of her pussy. It was tight, hot, and had to be dripping because I slid in and out easily. She was humping me with a slow, gentle rhythm and I could hear a wet sound each time she raised or lowered herself. She would grind her hips each time she lowered herself. She ground her clit against my pelvis each time she did.

After a few minutes of her slow fucking me, she leaned forward so her belly pressed against mine. Her face was in front of mine and we looked into each others eyes as she started to move her ass and hips faster. We had both begun to breathe harder.

She panted "the girls at the club taught me how to twerk. It gets me good tips when I bounce my fat butt for the guys. And it feels great to do it when I've got a good cock in me too."

She was right, it did feel amazing as she twerked on my cock. I could hear her pussy squishing on me faster and faster. Her tits were mashed against my chest so I reached around her and started rubbing her back as she bounced her pussy up and down on me. She was moaning in my face and I guessed she was about to cum. I raised my head up and kissed her. She returned my kissed and I felt her cunt grip me even more tightly.

She broke the kiss and cried out "ah! Ah fuck, shit, cumming so good!"

She ground her clit harder against me as she rode out her orgasm. Her twerking and humping had stopped and she flopped down bonelessly on my chest when she had finished. I could feel her juices dripping down my balls as she recovered from her orgasm.

She looked at me, smiled and asked "damn that was good for me, did you get off?"

I shook my head and said "no, but I'm really close. Can I fuck you from behind? I want to pull out and cum on your beautiful ass."

Grinning, she nodded and said "I love doggystyle. And I'm glad guys like my fat ass."

Stephanie raised herself off of my cock with a squelching sound. The air was cool on my prick because it was wet with her cum on it. She got on her knees and elbows in front of me and I got to me knees. I grabbed her waist and pushed my dick all the way back into her soaking pussy. Her big butt was pressed against my lower stomach as I started thrusting into her. I moved my left hand from her waist to her left cheek and started squeezing it. I humped into her faster and my thighs made a clapping sound against hers. I was pounding into her cunt from behind hard and fast. In and out, in and out, I loved seeing my dick plunge into her over and over. Seeing, hearing, and feeling my prick getting gripped by her pussy while I humped in and out of her was an intense turn-on.

I was close to orgasm before I had even gotten behind her and and after only a few minutes I said "I'm not going to last long like this."

She looked at me over her left shoulder and said "good, I want your cum to splatter my big ol butt."

I held out for maybe another minute of slamming my cock in and out of her cunt before I needed to pull out. I stroked fast and started cumming. My first shot roped out onto her lower back. I aimed the next two shots at her left cheek, spurting out two big strings of spunk onto it. My last three spurts were aimed at her right cheek, covering it in my white cum. I continued to stroke the rest of my cum out and it dribbled into her crack. I sat back on my heels and admired the view. She had cum on both cheeks and lower back. It was slowly dripping down from ass toward the back of her thighs.

She said "it feels like I'm covered!"

I said "you are. It's hot as hell too."

She asked "mind if I use your shower?"

I shook my head and she went into the small bathroom connected to my bedroom. I heard the water turn on and laid back down while she showered. I used a shirt to clean off my prick and waited for her to finish in the bathroom.

About ten minutes later, the water shut off and she came into my bedroom. She had dried off, but her hair was wet. She'd cleaned off the makeup she'd worn the night before, but she still looked great.

I asked "what's your plan for today?"

She shrugged and said "all I need to do today is make a deposit with that cash from last night, and then drop off a rent check. Then I have another shift at the club at 10 tonight. Friday and Saturday nights are the best nights for tips. Want to get dressed and take me back to my car?"

I laughed and said "no, I'd rather stay naked with you forever, but yeah. Let me get up and shower real quick."

She chuckled and went back to the living room to get her clothes. I got up, showered quickly, dressed in jeans and a t-shirt and went into the living room. She was just putting her shoes back on when I came in.

I asked "want me to come with you while you run your errands?"

She said "sure, beats doing them alone. Can you run me by my apartment so I can change into fresh clothes?"

I nodded and we left my apartment. We chatted while she gave me directions to her place. She only lived a few miles from me. Stephanie asked about my job. I was new to it, but it was a nice fit for me. I enjoyed the office environment and was good with clients and staff. I asked her about her job.

She said "I love dancing. It makes me feel sexy when guys watch me. The money is still decent, but not as good as it was even 5 or 6 years ago. It doesn't help that the club I'm at now is pretty bottom tier. There are a couple nicer clubs in town, but they won't hire me on. They have age limits on their girls."

I said "that's dumb. I bet you're hotter than any of the girls they have performing."

She replied "thanks, but most club owners disagree. I figure I only have another year or two left before I have to quit and find another job. By the time I'm 60, I figure I won't make enough tips to live on anymore."

I asked "what about online? There are sites you can get set up on to receive tips for stripping online."

She replied "like what?"

I said "there are sites for porn stars and amateurs alike. You can post pictures and videos, and people can pay to see them. By either buying viewing access, or they can send tips."

She said "sounds neat, but I wouldn't have any idea how to go about it."

I said "if you'd be interested, I could show you a site and help you with it. It'd be a way to reach a much wider audience and probably make as much or more than you would dancing."

She looked skeptical and said "and guys online would be interested in seeing an old woman like me when they can see porn starlet 20-somethings with fake titties?"

I chuckled and said back "you'd probably be surprised with how many people would want to see your body. Not just guys either."

She shrugged and said "what the hell, I'll give it a shot. I'd like to do sex work as long as I possibly can."

We arrived at her place and I stayed in the car while she went in. A few minutes later, she came back wearing black leggings and a Van Halen t-shirt. She also had a small bag with her besides her purse. Her ass looked amazing in the leggings. They clung to her like a second skin.

She got back in the passenger side and said "to the bank, please, driver."

I played along and said "at once ma'am."

She held up the bag and said "for my shift later. Red hot pants and red bikini top. Usually a crowd pleaser."

I said "that does sound pretty good. Maybe I'll come by and watch the show."

She gave me a sly look and said "you can have a private show after I get out for the night. No need to pay the cover price again when I'll give you all the dancing you want tonight."

That sounded great to me. We arrived at her bank and she went inside while I waited in the car. I watched her ass sway in the leggings as she went inside. A guy opened and held the door open for her and I watched as he gave he gave her butt an appreciative look. Yeah, she could make a killing online I thought.

Ten minutes later she came back to car and said "okay, rent won't be late. Hungry? There's good Mexican restaurant up the street."

I nodded and we went to the restaurant. I was still very slowly learning places in my new town. After the waiter took our orders we started talking about my online idea again.

She asked "so people subscribe to see pictures of me? How do they even find me on there?"

I replied "I think you can search for certain models, or search by tags. Like keywords that describe them."

Dryly she said "like 'old'?"

I said "no, I'd say you were 'mature.' Also I'd tag you as 'natural', 'big tits', 'exotic dancer', 'bbw', and probably some more."

She asked "what's bbw?"

I said "it stands for 'Big Beautiful Woman'. Any girl online gets labeled that if you can't see their ribcages."

The server brought our drinks with chips and salsa over. We stopped talking until he had left again.

Intrigued, she asked "so how do we go about it? What do you charge for a subscription?"

I said "you can charge whatever you want, but I'd start off with a free account. Then have some picture sets on there that people can see, and have some more explicit stuff that they have to pay to see."

She nodded and said "ah, we do that at the club. Tease them on stage so they're dying for more and then they pay for private dances."

I said "exactly. And if you wanted to do videos, I'm sure people would pay for those."

She asked "what kind of videos?"

I shrugged and said "porn stuff. Masturbation videos, sex stuff, I'm sure feet videos would probably get certain viewers' attention. Your dancing would probably make for some great videos."

She said "okay, I think I'm getting it. What do you think, like, 10-15 free picture sets to get people interested?"

I said "maybe start with 5 sets, and then when you have 20 or so subscribers, upload something more explicit. There's also other stuff you can do for tips. You can do custom uploads too. Like someone might want you to say their name in a video, and they'd pay for that. You'll be able to send and receive messages. A lot of models will do 'dick ratings;' they charge a fee and a guy will send a dick pic, and you tell them what you think."

She giggled and said "no way! Really? I'd do that for sure. Usually I get them unsolicited. So it'd be nice to get paid for them for once. Have you ever done it?"

I shook my head and said "no, I've never felt the need."

She said "well I give it a ten. Your tongue too. So, you'll have to help me. Unless all my pictures are going to be in front of a mirror, you'll have to be my photographer. Do you have any photography experience? And if I progress to sex, you'll have to be my stud. We'll split any money that we make. "

I said "no, you're doing the work, I'd just be taking pictures with a boner, you should keep the money. I don't have much photography experience, just a photography elective in high school."

She laughed and said "that's fine, better than what I could do alone I'm sure. How about 70/30? I insist. If this makes money, you should get some too, it was your idea."

I agreed as our order came out and we ate and talked about her new online venture. She was getting excited about it now. We planned a few things she wanted to try. Certain outfits, poses, makeup etc. After lunch, she wanted to get started. We went back to her place; it was a small apartment that was clean and tastefully decorated. We sat together on her couch and I brought up a site on my phone. We set up an account and set her up with an online payment account to attach to it. She was going to be "Midnight Dancer" on it.

I said "it looks like you can pay to have your account boosted so more people see it. That would probably be a good idea at the start."

She said "yeah probably. Want to get started? I got some new lingerie last week and it would probably be a good first outing."

I told her that I was ready to start too. She led me to her bedroom so she could get ready. I removed a lampshade from the lamp on the nightstand. It brightened the room considerably. Stephanie opened her dresser drawer and pulled out a black, lacy bra, black stockings, and a black thong and laid them on her bed.

She asked "think that will make a good shoot?"

I said "looks sexy to me. Let me get a photo of the outfit."

I used my phone camera to snap a shot of the lingerie. Stephanie took her shirt off and she was wearing a beige, functional bra underneath. She unhooked it and let her boobs hang free. I took pictures as she did.

She reached toward her leggings and I said "wait, let me get some shots of your pants. Your ass looks amazing in them."

She turned around and let me get pics of her big ass in the leggings. She bent over and stuck it out. I was already getting hard and she hadn't even touched the lingerie yet. I took more pics as she lowered the leggings and stepped out of them. Stephanie then started putting on the black bra. It had low cut cups that just barely covered her pink nipples. Then she pulled on the thong, and snugged the back between her pale, round cheeks. She then sat down on the bed and started putting on the stockings which came up to mid-thigh on her. When she was finished dressing, she stood up and checked her reflection in her mirror.

She turned in a circle and asked "how do I look?"

I gestured at my hard-on and said "you look great."

She laughed and said "well that's the idea. I'm just going to pose on the bed and strip. You take photos and then we'll decide which ones look best. Ready?"

I nodded and she got back on the bed. She laid down with one leg crossed over the other and I took a picture. Then she widened her legs. I moved in for a close shot of her panty covered pussy. She sat up and I continued shooting. She then removed her stockings; I made sure to get shots of her legs and feet. Her cleavage was deep as she leaned over to remove the stockings and I got a close shot of her hard nipples poking the bra fabric. Stephanie turned over and got on her hands and knees. The thong looked so good in between her ass cheeks. She smiled at me over her shoulder, it made for a sexy shot. She rolled over again and took the bra off and revealed her naked breasts to the camera. She held them up and then let them go. She then laid on her back and raised her legs up. She slowly took the thong off, pulling them off her legs. I got in for a close up view of her pussy shown through her legs. She then lowered her legs and spread her arms above her head. Her naked body looked excellent on camera. She spread her legs, revealing her pussy and pubic hair fully to the camera. She then spread her outer lips so I could get a pic of her wet, inner, pink lips. Fully naked, she posed a few more ways for me.

I got a few more shots and said "I think that's good. Any other shots you want?"

She said "no, but I need to get fucked. Posing was a huge turn-on for me."

I was more than ready. I took my clothes off and said "want to take pics while we do it?"

She said "no, just fuck me right now."

Stephanie moved to the edge of the bed and laid on her side with her legs straight out in front of her. Her ass protruded from the bed slightly and standing, I slid my cock into her dripping pussy. I'd never had sex with a woman in that position before. Sort of a sideways doggy style. She bit her lower lip and looked at me as I entered her. I started humping into her and I enjoyed seeing myself plunge in and out from the side like that. After a few minutes, she told me to pull out so she could readjust. When I had pulled out of her hot pussy, she moved to where she was on her fully on her back. She lifted her legs up and put her heels on my shoulders. I held onto her legs and she used a hand to guide me back into her soaking cunt.

She started rubbing her clit and said "give it to me. Hard and fast, but don't pull out when you cum. I want to feel your spunk inside me."

I did as she said and fucked her as hard as I could. I slammed my prick in and out of her and she moaned on each forward thrust. My hips made a slapping sound against her thighs over and over. Stephanie rubber her clit in circular motions and started breathing even harder than she had been. Her tits bounced in a rhythmic motion with my thrusts. I felt sweat drip down my back. I kept my pace up as long as I could but I felt my orgasm about to hit me.

Panting, I said "I'm gonna cum!"

She yelled "yes! I'm close! Cum in me now!"

With a groan I pushed into her as deeply as I could and started cumming inside her beautiful pussy. I watched her face as I blew and her got wider. Her hand was a blur stimulating her clit, I looked down and watched as her pussy contracted around my dick. As she came, she arched her back and moaned out a long "oooh" sound. I stayed inside her cunt until her orgasm began to subside. When she finally finished, I pulled out. My white spunk immediately started trickling out of her pussy and dripped toward her ass. Stephanie sighed contentedly and stood up and quickly walked into the bathroom. I laid down on he bed. A minute later I heard a flush and she came back into the bedroom. She leaned over and used her mouth to clean off her and my cum from my deflating dick.

When she was done, she laid beside me and said "mm, I love the taste or our cum mixed together."

I kissed the top of her head and said "you're the sexiest woman I ever met."

She cuddled closer to me and we talked until the evening about our lives, and what we thought would be good to try on her site account. I'd just met her yesterday, but I already felt close to her.

***

Thanks for reading, your feedback, and your ratings. If you keep reading, I'll keep writing. All people mentioned in this story are fictional.