My 27th Prostitute--Young Anal Delight! free porn video

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The 27th prostitute I saw was a short woman in her early 30’s with a few piercings and one tattoo on her ankle, and gorgeous facial features. Beautiful eyes, lips, & cheek bones and her make up looked great. She was slightly on the heavier side, but not fat by any means. I had contacted her because she offered “Greek” a.k.a. anal, which I had not done in over 20 years.

I drove to the hotel at the agreed upon time. It was a cheap budget place. Not the worst I’ve ever seen. I like a cheap place as long as it doesn’t seem dangerous. It can be nerve wracking seeing someone for the first time. Fear and paranoia of it being a set up can really invade your mind. I bit the bullet and knocked at her door and she opened up right away. She was much younger than me and she looked sexy so I was happy right away. We took care of the money immediately.

I can’t say she was in a great mood, really she seemed a bit sour. I made small talk, trying to make some kind of connection with her. She had just visited with her Dad and she started talking about him, his sense of humor, what music he likes, a disagreement they had, food he enjoys. It became clear to me I probably had more in common with him than her. It sounded like he and I are the same age. I also wondered if perhaps she had daddy issues of some sort.

She let me know her lists of rules, what she didn’t like basically. One of them was no breast touching. This was the only rule I was disappointed to hear. I’d say she was a solid D cup, so she was probably sick of guys grabbing at her tits. I made peace with it and didn’t complain. Hey, at least I got to look at them, they were spectacular when she took her bra off. And besides, I was going to get to do anal, how could I complain?

She asked if I wanted to start with anything or get right to the anal. I choose anal right out of the gate. She decided a covered blow job was the best way to start and I didn’t argue with that. We got undressed and I lay on the bed. She stroked my cock for a minute while making a bit more small talk, then she put the condom on. She leaned over and put it in her mouth. Her mouth formed a very tight grip around my old cock. Honestly, it was a treat to watch this young lady bobbing her head up and down on my member. I stared and enjoyed the show, looking at her body, her nice big tits, staring back again at her mouth with my cock in it, up and down she went, taking it in her mouth. Beautiful.

“This is the only position I do greek from” she said, and she got on all fours in doggystyle. I had no problem with that. I hadn’t even thought to do anal from missionary frankly. She got out some lube and applied it to my cock. “Okay, go ahead”. I slowly pushed my old dick against her young anus, holding onto the sides of her ass, slowly I pushed, she let out a quiet moan which made me even hornier. Her ass opened slightly and accepted my cock and I pushed it in, then a little deeper. She moaned again, “Ohhhhh”, I loved the sounds she was making. I watched my cock going in her ass, then out, then back in. In and out, in and out it went. It was so tight in her ass. I stared down at her. She was ass-up face down with her head turned to the side so I could see her profile, she did not look pleased, she was grimacing. I looked back down and stared some more at her ass with my dick going in and out, in and out, in and out. It was mesmerizing, and it felt incredible. I loved being with a younger woman, a total stranger, who was letting me gently fuck her in the ass. It was a rush.

I knew I wasn’t going to last long. I tried to take it all in and savor the moment. Staring at her face with her pained expression, I then glanced around the room, sunlight pouring in through the crack in the blinds, a cleaning woman’s noisey cart down the hallway, the sound of the bed creaking with my slow thrusts in and out of her ass, and her quiet moans.

I had wanted to nut on her back but she told me it cost extra to do that, and I didn’t have that kind of cash on me. The excitement had built, my old cock buried deep in her tight young ass, her expression of unhappiness which turned me on for some reason, the moaning, I was going to cum. I began to spurt inside her. I stared down at her beautiful ass as I orgasmed. My body involuntarily spasmed as the last of my cream shot out.

When it was over she instructed me to flush the condom. I was already taking care of that, never leave it behind. She wiped herself and cleaned up, offering me a clean washcloth also. She seemed cheered up now that it was over. She was in a good mood! She seemed as sweet as sugar now. We chatted for a few minutes, it was great. We hugged and parted ways.

She came back to town about 2 months later and I went and saw her, but she was in a terrible mood the second time, and I knew I would probably never call her again. The 2nd visit was just to difficult, not an experience worth paying for. But when I think of her I think only of the 1st visit. Her youth, her possible daddy issues, and gently ass fucking her.

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Even then, though, I already enjoyed the male attention. I guess it was the beginning of my journey to slut-dom, fucking every cock I can find and posting my nude photos and sex videos online, especially now I’m 34E. One spring day, a boy I knew a bit came up to me behind the shelter sheds at lunchtime and started talking to me. I used to hang around there because it was a bit out of the way and allowed me to get away from the hustle of the schoolyard. He was a bit nervous and suddenly he...

2 years ago
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Brother prostitute

The night was warm for a Friday, most summer nights was so hot you would sweat even in the shade. Jasper made his way home as fast as he could for he knew that his mom was on a date and would be out till midnight at some party, and he also needed to relieve the pressure that has built up in his still hard cock, thinks to his bitch of a girlfriend. As he walked in to the house he ran up to his room pulling off his cloths until he was naked, he sat down on his bed and started to stroke his hard...

4 years ago
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The Prostitute Wives

It was Tina Barton's birthday. She, her husband Mark and their son, Tag had gone to pick up her new BMW and dinner at one of their favorite places to eat. She had a couple glasses of wine, her husband some beer and Tag some coke. They were all quite happy when they got home quite late. Tina suggested that Mark made sure that Tag got his shower, brushed and flossed his teeth, and then got him into bed. She told Mark to also get his shower and she would meet him later in their bedroom. In the...

Lesbian
3 years ago
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How I became a gay prostitute

In talking with some of my hamster friends, I told them about my sexual experiences. Some of them suggested I write them as stories for everyone to enjoy. I thought that would be a good idea, since I also like sharing and talking about it.Everything you are about to read really happened, and it happened to me. The story is absolutely true to reality and is not embellished in any way. How I became a gay prostitute.When I was nineteen, I was working in a restaurant. It was fairly fancy, and the...

4 years ago
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Britney A Beautiful Prostitute 2

Joe and many other men checked out these beautiful women. None of them knew that these woman fucked for money, only Joe knew that. Before any other waiter could go to attend Britney and her friend, Joe ran towards them. “Welcome,” Joe said and thought if he should call Britney by her name or just say, ma’am. “Thank you,” Britney replied with a big smile, as she remembered that Joe was the man who fucked her last night. Joe took Britney and her friend to a table in the corner. Men in the...

MILF
4 years ago
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Confession Me a prostitute No waywell maybe

For a few months, we hooked up for sex whenever he was in town. On the whole, it was good. There were times he didn’t treat me very nicely but most of the time he lavished affection and praise and compliments. And of course there was the money. During that time, he had paid me over $3,000 in total!!One night when he had taken me out to dinner and was sweet talking me, he told me about a friend of his who was going through a divorce and said he wanted me to do something for him. He wanted me to...

2 years ago
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The Gentle Prostitute

(continuation from 'Elizabeth's Fall From Grace'.) Some weeks later, Helmut asked Elizabeth if she would like to earn alittle money. 'By what means Helmut?' 'A travelling salesman visits me once a month, and stays at the night atlocal hotel. Would you like to have him stay at your house instead?' 'We have no spare room in our little house.' 'I know. But he'll pay handsomely if he can share your bed!' Helmutreplies with a grin. She is shocked by what he proposes! Elizabethreplies...

4 years ago
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amatuer crossdressing prostitute

So it started out by just a regular day. Work was really becoming a drag, and it was only 11:00 am, and my mind started wandering about what I was going to do when work was over for the day. I stopped at the mall on my lunch break and when I was done at the food court I decided to stroll through Dillard’s on the way back to the parking lot. I couldn’t help but pass through their lingerie section and noticed the cutest little bra and panty set. It was kind of a purplish flower ensemble that I...

2 years ago
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Pretend Prostitute Part 2

Late last night my phone rang. It was Brad. He said that his friend that thinks I'm a prostitute was in the mood for my services again. They'd gotten a hotel room close by, and I was to arrive as quickly as possible, following the instructions I'd been given.Forty five minutes later I was in the lift at the hotel. My face was heavily made up per Brad's instructions, I was wearing knee-high Fuck Me Boots with stiletto heels, stocking and suspender belt as requested. I was also wearing a mid...

Straight Sex
2 years ago
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Experience With Prostitute

Hi All, My name is Sandip. I am 5.8, fair boy, work in IT idustry. Ladies are welcome to open up their wishes of secret encounters, do catch me at This is a read story which happened with me last year. I am a religious and spiritually inclined person. I normally visit new places. One year ago I visited Kamakhya Temple, Guwahati and it is one of the best Shakti Peeth in world. I did a lot of research about Kamakhya temple and it’s famous annual festival Ambuvachi Mela. It was from 22 June to 26...

4 years ago
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My Wife A Lesbian Prostitute 8211 Part 3

A big Hi, to all of the readers of ISS. Its really a privilege that such a forum has been created by the makers of this website. I find many of the stories being too artificial and made up while some are certainly genuine. As I have mentioned in my earlier parts, this is a fact of a story. But due to the gravity of the matter , I have to be extra cautious, in divulging the details of character involved and their location. Also , ISS takes a lot of time to publish stories. In this case it was...

Lesbian
3 years ago
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My Experience With Prostitute

Hi i am jaya prakash from villupuram which is in southern part of india.I was studying first year of engineering so my age was 19 years when this was happened. I have experienced a sex when i was traveling in bus a man aged 40 or something came to sit near me and i was sleeping too during this he started to put his hand in my thigh i thought it might me due to his sleep but he started moving his hand towards my penis I noticed and i let him do that slowly he moved his hands and started pressing...

4 years ago
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From Neighborhood Aunty To Prostitute

Hi friends this is Naveen, am normal typical south Indian guy little fat. Naturally my body looks like a masseur, even I hit gyms also because of laziness, I won’t able to continue the gym. I work here I stay here with my friend, we both work in a same company but in different shifts we were college classmates and also working in a same company, he is tall guy and nice slim body good guy most of the girls talk to him, he also talk to many. From the school days and college life most of girls...

4 years ago
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Banged A Hifi Prostitute In Open Balcony

Hi to all ISS readers this is Varun back to share my another experience and for those who don’t know me I am Varun 23 years old guy from Chennai 6 feet tall average body and have a 6 inch tool and I thank you for all your response for my last story. Any ladies can contact me through This is my experience of me fucking a prostitute. Now coming to the story I have always had a desire of fucking a high profile prostitute in a nasty and a forceful but I feared it was risky but finally decided to...

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