The start of my new business and new life as a real prostitute.

After a good night of sex with 3 different men I sent Hank to my spare bedroom. Then I went to sleep alone. I laid down and I was still leaking cum. I couldn’t believe I was even doing this. But I had done this before with my husband. And I did make enough money to pay the bills that were due this month. I had a hard time putting my morals on hold. I have been told all my life that prostitutes were just dirty women with no shame. And I had a lot of shame so I didn’t think I would make a good prostitute. I turned on my light and counted my money. I smiled patted my wet pussy and told her to keep up the good work. I push my shame to the back of my mind. And drifted off to sleep.
I woke up early took a long shower then cleaned out all my dirty holes and took another shower. By then Hank was up and moving around.
“Hank I need you to run to the adult store across town. I need a nice size butt plug and some lube. Pick up some condoms large ones. Here’s ten bucks for gas. I’m going to stay here and do some yoga and stretching. I have a feeling tonight. I’m going to need to be limber.”
Hank came back and I went back to the bathroom to clean myself out again and then I lubed up the very large butt plug Hank I bought me. It took a bit to get seated into place. I was about to ask Hank for help with it when my ass opened and the base of the plug went right up in between the cracks of my ass.
I pick myself up off the floor and stared in the mirror with my mouth still open wide, not believing that something that big was still inside me. I was thinking about pulling it out but the thought of pulling it out was just as painful as the thought of keeping it in. So I walked gingerly to the living room and sat down on the couch.
“Are you okay Kathy?”
“ I will be. I just need a minute. This plug is a little bigger than I thought it would be. “
“ well I thought about getting the smaller one. But then I thought about how large Doug was. Then I thought about how big I was. I’m not sure how big the guys that I know at the gym are. So I thought might as well go big.”
“ well it’s big.”
“ why don’t you just make some breakfast and try to pretend it’s not there.
“ hank, I don’t think I’m going to forget there’s a 2 1/2 inch all the rubber sticking up my butt. But I am getting hungry, so I guess I can make breakfast.”
Waddling around my kitchen with my ass stretching with every step was a new sensation. And by the time I got my eggs finished, I was kind of horny again. I was thinking about asking Hank if he was in the mood. But by the time I finished my eggs, I had thought about it. And decided that having two or three guys having sex with me tonight. Maybe I should take the morning off. By 3 in the afternoon I couldn’t stand it anymore and took my anal plug out told Hank to call one of his friends and to bed I went to wait for my first customer.
My first customer showed up his name was Jeremy. He was a little on the small side. Maybe 5 1/2 inches once I got him hard. He was definitely into my breast. He sucked on them quite a while and my nipples actually hurt not in a fun way. I had to tell him to hurry up and put it inside me. Which he did and he knew how to use what he had. I had a nice orgasm. And I looked up and I could tell that he was about to have his own when I yelled at him to stop.
“ Jeremy, I know you said you only wanted to have vaginal sex. But I’ll be having anal sex tonight with a few men and I was wondering if you would do me a favor and kind of warm me up. I have a large butt plug, but it’s nothing quite like the real thing.”
“ are you joking? You’re just going to roll over and give me some ass.”
“ if you want. As long as you last a good five minutes.”
To my painful surprise. Jeremy lasted 10 minutes. And I was farting lube for the next half hour after he left. But I was definitely warmed up. My plug went back in easily and I made a quick snack for Hank and myself. Doug showed up at 6 o’clock sharp. He was very eager to get started. But I insisted on a little foreplay. Which he was happy to give and so was I. He started getting a little aggressive, fucking my throat. And I decided that it was time to just spread my legs and get it over with. But Doug took his time, stretching my pussy out first. Then he asked if I was ready for the main event. I nodded my head and rolled over with my ass in the air. Doug pulled hard on my plug and there was an audible pop when it came out that took my breath away.
“Holy shit!! Easy Doug or this might be the last time you get a chance at my ass okay.”
“ sorry Kathy. I’ll be gentle. At least until you tell me to get a little rough.”
Doug laughed I didn’t. I had to keep reminding myself that he wasn’t my lover. He was my customer. But he was a very courteous customer. Who started off gently and loosened me up quite well. Then when I was sure I was stretched out enough I begged him to go to town and pound on my ass for a while. That might’ve been a mistake. Doug went to town. And he tore my ass up for the next half hour. I found out later that he loved popping Viagra.
By the time he was done my guts hurt and I was sure I wouldn’t shit right for the next few days. Then he finally finished by giving me what I can only describe as a cum enema. He laid on top of me catching his breath and when he rolled off I thought I was shitting myself. But it turns out it was just a river of cum pouring out of my broken butthole.
“Holy fuck Doug. No one has ever abuse, my butt that bad.”
“ well I wanted to get my moneys worth “
He sure got his moneys worth that was for sure. He took a shower and I was just laying in bed occasionally running my finger down to check to see if my asshole was ever going to get tight again. Or at least tight enough for a good fuck later on. As Kevin said that he would be glad to pay another $200 for anal tonight. Kevin was a young college kid spending his parents money. I figured even if I was a little loose, he wouldn’t mind.
I said goodbye to Doug and then lamp up to the kitchen to get me a drink
“ it sounded like Doug was killing you back there”
“ well it felt like he was killing me or at least part of me. I don’t mean to turn you on by doing this. But come over here and look at my butt hole. Am I bleeding?”
“ well you’re red and swollen a little bit. Looks like Doug had a good time.”
“ I had fun too for a while. But then it got painful before he was done. “
I took another bottle of water out of the refrigerator and went to the couch with. I said that cool model between my legs and it felt good. I had a 30 minute rest before Kevin showed up. When he did, I had Hank fix him a drink, and I took a quick shower.
Soon Kevin was back in my room. He was eager to find out what I hot milf tasted like. I wasn’t going to turn a man down that wanted to heat me out. He did a good job and brought me to an orgasm maybe two. Then he stroke my pussy with that beautiful cock of his. He was warming me up good and I had another orgasm. I felt bad because I knew he was going to come soon. I didn’t stop him. I could have I could’ve rolled over and let him fuck my ass the way he had wanted to. But I just smiled and let him continue. And soon he was dumping his load.
“ it’s OK Kevin. I’ll give you a piece of ass next time OK? “
“ okay. Man I just couldn’t stop. You’re the best Kathy “
I wondered how many women Kevin had been with to think that I was the best. I decided not to ask.
I said goodbye and Hank told me that he friend tom wanted to know if I was available.
“ well I guess so. I mean I’m a whore right. I don’t say no. It’s in the job description.”
Hank smiled. He knew I was tired and I wanted to go to bed. But one more customer wouldn’t hurt.
Tom was not hung like a horse, thank God. But he had a great 7 inches that made me feel good. I did have to add a little lube before he finished. But it was still nice.
After a long night Hank offered to help me in the shower. I knew he was horny. But Man wouldn’t be sitting out in the living room listening to me, moaning all night. I let him help me wash up. I even went to my knees and gave him a nice blowjob. I even let him come on my face since I was already in the shower. I told him it wouldn’t be an all the time kind of thing. But I didn’t want to show how much I appreciated him.
I made just over a thousand dollars in one night. My butt felt like I had fucked a freight train. My poor pussy was swollen and it hurt to even touch it. My nipples were still hard and red from the chewing that Jeremy had done earlier. I laid down in bed for the night and I knew this job would really hurt my body if I had to do it all the time. This was a job for young women. Not one pushing close to 50. I enjoyed sex. But not sex work. I would be taking a few days off. But I couldn’t deny that even with a few days off and working only two or three days a month I could easily pay all my bills. It had an appeal to it. Maybe I’ll stay in the whore business. Maybe. We will have to see.
Thank you for reading.
Comments are always welcome. I’ll try to answer as many as I can.
If you’re reading this and you wanted something else. I’m sorry they didn’t have a prostitution category.

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