Cindy Hammons walked around the corner ready to cross the street to her building where she lived with her boyfriend Fred. They had moved in the week before and she enjoyed living in the city. She looked both ways before crossing, rolling her makeup bag behind her. She had just a few hours to grab something to eat before she was off to her next appointment. Cindy was a makeup artist. Mostly she did weddings and some theatre work but lately she had begun working on businessmen and women. It was fun to transform a dreary, tired looking executive into someone not even he or she recognized.

As she pulled the bag up on the sidewalk again, she noticed something from the corner of her eye. A large bundle of dirty clothing lay close to the entrance to the building. As she passed it, she looked closer and noticed it actually moved. It was a person.

“Hey, you can’t stay here. There is a shelter a few blocks away,” she said in a kind voice. She used to help out at a shelter when she was younger and knew how much good they did.

“Fuck off bitch and leave me alone,” came the harsh answer from within the bundle.

Cindy ignored it and went into her building. Many of the vagrants had mental issues or were just angry at the world. In the elevator she checked her face in the mirror. She liked to look good for Fred. Her makeup was perfect as expected and her hair was in place even though the breeze had given it a hard time during the five-block walk. She wore tight fitting jeans a simple white top and a leather jacket that ended just above her hips. Practical and stylish.

As she approached the door to their apartment, she could hear music; Iron Maiden blaring out of the speakers.

She found Fred in the kitchen using a fork and a spoon as drum sticks playing in the air.

“Honey, honey!” she shouted.

Fred jumped at the sound of her voice and then used the remote he had in his pocket to lower the music.

“Hey, baby. I didn’t hear you come in.”

He came forward to hug her. Fred was wearing an apron that had the text “Master Chef” stencilled on the front and nothing else.

Cindy smiled as she saw his cock harden, poking at the apron.

“Hey, I see you are cooking. What’s for lunch?”

He hugged her and they kissed. “Some tasty German Bratwurst is what’s for lunch.”

Cindy giggled and lifted the apron. Behind it, Fred’s cock stood at attention. A large red cockhead and the thick shaft with protruding veins.

“Looks good, how the sauce that comes with it?” she said while stroking him.

Fred was fumbling with her jacket and then her top. He got them off her and then undid her bra which fell to the floor spilling out her firm C cups. He licked each nipple in turn and then nuzzled her neck. “Hot and a lot of it, it’s all for you.”

“Really, all this for me?”

“Mm, get out of those jeans.”

She did and her white thong followed them. Fred lifted her up and placed her on the dining table. Behind her was the window that faced the street. She lay back and wrapped her legs around Fred’s hips. He grabbed his cock and lined it up with her shaved pussy.

“You are so hot, baby,” he mumbled as he pressed himself inside her.

“Ah, yes, god you feel good.”

Fred watched as his cock slid in and out of Cindy. Her pussy stretching and becoming wetter. Her legs pulling him closer, her boobs moving with her body as it rocked with his thrusts.

Cindy closed her eyes and let Fred do all the work, and he was good. She loved the way he fucked her. Few men had ever made her come with their dicks but Fred could. She grabbed the edges of the table and lifted her body a little. Fred pumped harder and faster. She could hear from his breathing he wasn’t far from coming, but that was no problem she herself was on the edge.

Cindy arched her back a little then she thrashed with her head, her long dirty blonde hair spilling out.

“Oh, oh, here I come, fuck me harder, baby,” she moaned.

Fred felt her pussy clutching his cock as her body tensed and she stopped moving. He gave it a few more thrusts before pulling out. Grabbing his cock, he jerked it and within seconds large globs of cum shot out spraying Cindy. Some flew as far as her face but most landed on her boobs with their hard nipples.

Cindy giggled and wiped some cum off her lips. Fred moved back and she sat up with her legs dangling over the table.

“Why didn’t you come inside me?”

“I thought it would be sexy to come on your boobs.”

She played with the cum that slowly ran down her boobs and dripping onto her legs. “It sure is warm. I need a shower. Finish lunch and I’ll be right back.”

Fred added salt and pepper to the Carbonara sauce he was making.

Cindy and he had met at college. He was working on his MBA when he had met the sexy undergrad at a party. It had been love at first sight. They spent every waking hour together if they weren't in class. When he graduated, he stayed in town for two years while Cindy studied and finally graduated. That’s when they had decided to move to the city. Fred found work as an investment banker while Cindy worked hard being a makeup artist.

Slowly she grew a customer base and now she was doing great. He was very proud of her and often bragged to friends and co-workers about her.

“Is it ready, I’m starving?”

He turned and there was Cindy. She wore slacks, a white blouse with her hair and makeup to perfection. It was hard to believe he had been fucked hard just twenty minutes earlier. That was one thing he loved about her. Most women took time to get ready, not Cindy. She could go from vicious hangover to a cover girl looks faster than it took him to finish a cup of coffee.

“Yes, have a seat. There is something I need to tell you.”

She did and he placed their plates on the table.

“What’s up?” she asked.

“I need to go out of town this weekend. A client is in town and he wants to go golfing.”

“Okay, that’s fine. I can hang out with Emma if I get bored.”

Emma was a friend from college who had also moved to the city after graduating.

“You sure, you are not upset?”

“Why would I be? It’s your work.”

“Okay, cool. How’s the pasta?”

“Fantastic, as usual.”

Cindy walked out of the elevator an hour later. Her pussy still felt slightly stretched and she had a stupid grin on her face. After lunch, Fred had fucked her again, but this time he had come inside her. Another shower but no clothes change this time.

The bundle was still lying on the sidewalk.

“Are you sure you wouldn’t be better off at a shelter?” she asked when she stopped by it.

It moved and a face showed. A heavy grey beard and long dirty hair framed it. It was smudged with dirt and the lips were cracked. Blue eyes stared back at her in defiance. “Leave me the fuck alone, woman.”

“Okay, okay, I just want to help. No need to be rude.”

“Fuck off, bitch.” the face turned into the dirty blankets.

Cindy sighed and walked on, heading for the closest subway station two blocks away.

Later that evening when she came back the man was still there but he had moved closer to the stairs leading up to Cindy’s building. As she passed him, he said.

“Spare some change, lady?”

“No, you were rude to me.”

“Fuck you then, rich bitch.”

She ignored him and sighed going up the stairs.

After dinner, she and Fred watched TV and snuggled in the sofa with a bottle of wine. As usual, it led to him suckling on her boobs and then they moved into the bedroom where he fucked her. Cindy loved having such an active sex life even though they had been together for a long time. Many of the women she worked on often complained about the lack of attention they got from their husbands or boyfriend. She couldn’t put herself in their shoes because she had never had that problem with Fred.

He wasn’t her first, far from it. Ever since she turned sixteen, Cindy had had an active sex life. She wasn’t promiscuous, at least she didn’t think so. She just liked to fuck and explore her own sexuality. She had even had a lesbian experience in high school and while it was fun it wasn’t really her thing. No, she loved the feeling of a hard cock penetrating her tight pussy and how it filled her up with it’s hot cum.

The morning Fred was to leave they had breakfast together and she mentioned the vagrant outside. He had been there for almost a week now and some of the other tenants had complained.

“Maybe you should call the cops?” suggested Fred over his black coffee.

“No, he hasn’t done anything wrong apart from being rude.”

“He could be dangerous.”

“Doubt it, I don’t even think he drinks. He never smells of alcohol.”

Fred got up and placed his mug and plate in the sink. “I got to go, baby. See you tomorrow evening.”

They kissed goodbye in the door and when Fred was gone Cindy took a shower and got dressed.

It was a warm spring day and the sun was shining. She put on her sunglasses and turned right, heading for the park a few blocks away.

The vagrant was sitting on the sidewalk with his face to the sun. Cindy stopped. He hadn’t noticed her yet. From where she stood, she noted his jawline and the way his face came to life under the dirt. He had at one point been a very handsome man, she realized.

“Good morning,” she said expecting some nasty words from him.

“Hi, there. I’m sorry for being an asshole these days.”

Cindy’s jaw dropped and she just stared at him before saying. “Okay, that’s cool.”

He smiled at her. “I get angry sometimes and I take it out on people around me, not your fault.”

“Can I help you in anyway, food maybe?”

He shook his head slowly and scratched his beard. “No, I’m fine. Thanks anyway.”

She left him and headed for the park. She liked to sit on a bench and watch the people walking by. It was relaxing and during a day like this, she got some sun on her. While she people watched she thought back to the man outside her building. Her uncle Derek had been a vagrant. In the beginning, he was a successful insurance salesman but then drugs and alcohol had taken hold of him. As the years went by it got worse up until her family stopped helping him. He lost his job, house and family. He ended up on the streets and finally died of an overdose in a dirty alley.

It had hurt her and she had often wondered what would have happened if anyone had given him a helping hand instead of pushing him away. She was only a young girl when this happened but from that day she decided to help those in need.

On her way back home she stopped at a thrift store and bought clothes and shoes. As she walked up to her building she saw that the man was still there.

“What’s your name?” she asked.

“Tom. Why do you want to know?”

She hunkered down in front of him. “I want to help you. I bought you some clothes and I want you to come with me. You can shower and I’ll make you something to eat.”

He looked at her with suspicion. “What’s in it for you?”

“Nothing, I just want to help.”

“Will you call the cops while I shower? Maybe tell them a story how I broke into your apartment?”

She laughed. “No, nothing like that. I just knew someone who ended up like you and I don’t want you to end up the same as him.”

“Who was it and what happened.”

“My uncle and he died.”

“Sorry.”

“C’mon, you can tell me your story over lunch.”

He gave her a grin. “You wouldn’t believe me.”

Tom looked at himself in the bathroom mirror. Cindy had given him a scissors and suggested he cut his hair and beard. The dirt was like a second skin on his face and body. He had lost a lot of weight over the years and what once had been a sculptured body with well-formed muscles was now a scarecrow of a man. He begun to cut his hair and then went to work on his beard. He scooped out the hair from the sink and dropped it in the toilet. Watching it spin around as he flushed, he noted a laundry basket. On top was a black thong. He picked it up and felt the soft silk between his rough fingers. Putting it to his nose he smelt the faint fragrance of body lotion and pussy. His cock grew hard which was the first time in months. After a final whiff he dropped the item into the basket and went over to the shower. It was one of those with multiple jets.

The grime and dirt ran down his body and he washed himself and his hair several times. Then he shaved and finally soaped himself again.

After drying, he dressed in the clothes Cindy had given him and stepped out. He felt like a new man.

Cindy turned when she heard him. “Oh my God, Tom. You look great.”

In front of her stood a man in his late fifties or early sixties. Even though he looked tired and he was undernourished she saw a handsome man with a square face and clear blue eyes. His hair was short but could use a professional touch.

“Please have a seat, lunch is ready. Would you like a beer or a glass of wine?”

Tom sat. “No, thanks. I don’t drink.”

She sat and they ate in silence. Cindy would steal glances at the man but he sat with his eyes half closed eating and chewing slowly. Cindy finished first and put on the coffee machine.

“This was very good, thank you,” said Tom when she took his plate.

“White or black?”

“Black, please, no sugar.”

She smiled. “Just like my boyfriend Fred.”

“Is he the tall guy, with a crew cut?”

“Yeah, that’s him.”

“Good looking guy. Does he treat you right?”

“Yes, he does. We have been together since college.”

“Cool, what do you do?”

“He works in banking and I’m a makeup artist.”

“I see, like in movies?”

Cindy put down the coffee mugs and then sat. “No, I wish. I do mostly weddings and some theatre.”

“I once had a makeup person.” Tom sipped his coffee and looked out the window with a vacant look.

Cindy was curious. “Did you? How come?”

Without turning to her Tom sighed. “I was in the movies, a long time ago.”

“Wow, maybe I have seen one of your films.”

He smiled at her. “I doubt it, you must have been a kid back then and it was adult films.”

Cindy put down her mug. “Really, you were in porn?”

“Yeah, for ten years. Made a career out of it and a lot of money. Back then we were stars, not like now when anyone with a camera can become famous because of the net.”

Cindy got up and a few minutes later came back with a laptop. She turned it on. “What’s your full name?”

“Tom Davidson, why?”

She typed and then put her hand to her mouth. “Oh my god, it’s true! You look so different.”

Tom laughed. “I was in my mid-twenties back then.”

“Tom and the Babysitter - that was the most famous film.”

“It sure was. Does it say why?”

Cindy read the information and slowly shook her head. “No.”

“The actress, Anna Barnes, she was just sixteen when she made the movie. She had given the producer a fake ID. And when the news came out people went nuts and the film became a success.”

“But, if she was underage, how did the film come onto the market?”

“It took a few months before the news came out and by then thousands of copies had already been sold. Remember back then it was VHS cassettes that anyone could copy at home and sell or give to friend. With no internet the police couldn’t track them.”

“What happened to Anna?”

"She didn’t make another movie until she was eighteen and then she had a brilliant career for a few years.”

Cindy closed the laptop and tilted her head. “So, what happened to you?”

Tom sighed. “Like I said, this was before the internet and DVD players. Porn was more artsy back then. As time went by things changed, I didn’t get as much work but kept on spending my money. One day I was broke. I tried to get into the newer stuff but no one wanted a thirty plus guy.”

“What about a regular job?”

“No education, and a no one want’s to employee an ex-porn actor. Not a resume to be proud off. I did get some work, mostly fast food restaurants, bar tendering and such, but nothing that stuck.”

“Still, you had income, no reason to end up on the streets.”

“I know, but back then I did drink and that’s how I ended up like this. I used to clean myself up but over the years it has become harder and harder.”

They sat in silence for a while then Cindy asked. “Out of curiosity, what’s it like to fuck in front of a camera crew? Isn’t it hard with everyone staring at you?”

“It was, in the beginning I was very nervous but you get used to it. The ‘hardest’ thing was to keep my dick hard. Back then we had no Viagra.”

“Oh shit, how did you do it?”

“We had fluffers. Between shots some wannabe actress had the job to keep the guys hard but not making them cum. It was difficult work, and some literately sucked at it.” Tom laughed.

“I guess the industry has changed a lot.”

“It sure has. Anyway, once I got used to being watched I could fuck for a long time staying hard. Not even after coming did I go limp.”

Cindy giggled. “Oh, really. That sounds amazing. My experience is that guys usually can fuck twice maybe three times before the cock gives up.”

“Not me, I did a minimum of five, sometimes eight fucks in a row.”

She looked out the window and her mind began to race. Here she was sitting across from a real porn star with, according to the covers to his movies, a long dick. Not as thick as Fred’s but a lot longer. What if? No, she couldn’t, or could she? Fred was away until the following evening and she had never cheated on him, well, apart from that girl which he knew about.

“I know what you are thinking, but I can’t guarantee anything.”

His words brought her back to reality. “What?”

“You are thinking about how it would be to fuck me.”

She crossed her arms and leaned back in the chair. “No, I wasn’t, that's crazy,” she smiled.

“I can spot a horny woman easily. You licked your lips, your chest heaved as your breathing increased, you crossed and uncrossed your legs as you felt yourself becoming wet. It’s fine, if you don’t want to.”

Cindy stared at him. She had never been read that well in her life. She was wet, she was horny and yes, she wanted him to fuck her. She stood up and went around the table. “Show me.”

Tom opened his pants and pulled out his cock which was hard.

“Wow, that is long.”

“Some girls called me “foot long” back then.”

She laughed. “That is funny.”

She grabbed his cock and began to stroke the full length of it and as she did the cockhead slid out, red like a strawberry and so inviting. Kneeling between his legs she took him in her mouth. She couldn’t get all of him inside but she tried hard.

“It’s okay, just relax, don’t force it,” Tom told her.

Stroking and sucking him made her even hornier. She slid a hand down and opened her pants and then wiggled out of them while still sucking. She had to stop to take her top off and then she moved in closer and wrapped her tits around his shaft.

“Those’re some boobs you have there,” said Tom.

“Thanks and they are real.”

“Yeah, I can feel that, not hard as the fake ones.”

He watched as his cock slid between her tits and the pre-cum began to trickle out. He wanted her badly, to again feel a hot pussy around his cock. It had been many years since the last time.

Tom pulled her up and pushed the naked Cindy over the table. His cockhead spread her swollen pussy lips.

When he entered her it was like no other experience she had ever had. There was no end to his cock, it only slid in longer until it reached the end. She was stretched but it didn’t hurt, it felt amazing. Once he began to move she thought she would die of pleasure.

“Oh, oh, I have never had this much cock in me.”

“Glad to be of service.”

His hand had reached around her front and he pulled at her nipples as he fucked her harder and harder. His balls smacked into her and her legs began to weaken.

“Yes, yes, Tom, give it to me, fuck me like you did those porn starlets.”

He grabbed her hips and rammed his cock as far inside he could not slowing down. She grabbed the table cloth and tried not to scream but when she came, she did, worrying that the neighbours could have heard. At the same time as the orgasm shot through her, Tom shot his load inside her. She felt it run down the inside of her legs. But he didn’t stop or become limp. Instead he turned her around so she was sitting on the table.

Looking down she saw his cock sliding in and out of her and the sight of it made her come again. She began to rub her clit and came once more. Tom moaned and pulled out, shooting his load over her breasts and stomach, still staying hard.

He reached for something behind her and when he poured extra virgin olive oil over his shaft and then rubbed it in, she thought she knew what was next.

“I’ve never been fucked up the ass,” she whispered

“No? You will love it.”

She leaned over the table again and before she could say a word Tom’s cockhead pressed against her anus. It must have been the horniness because she opened up like a flower in spring.

“Oh, oh, that stings a bit,” she protested.

“Shh, Cindy, just relax.”

She did and as he began to fuck her a warm feeling came over her. She felt so exposed but it was hot and sexy, dirty and pornographic, and she loved it.

She slid a couple of fingers inside herself and that made it even better. Within minutes she came and her anus clinched Tom’s cock.

“I’m going to fill your ass with cum,” he whispered in her ear.

“Please, please give it to me.”

All her nerve endings tingled as the older man came deep inside her and when he finally pulled out it, and it ran out in a steady stream she must be gaping, she realized.

Turning around she noted how his cock was going limp. “Oh, that is so sad,” she said and gave it a squeeze.

“At least I gave you a few good orgasms”

She kissed his lips. “Yes you did, thank you. You must have been amazing when you were at your peak.”

He laughed. “I sure was. As much fun this has been, I must go. I realized that I need to get my life back and I know just where to start.”

A few weeks later Cindy and Fred sat in their sofa. He is working on his computer and Cindy watching a movie. She had introduced anal sex to him and he had liked it. She had said it was a long-time fantasy that she had finally decided to act out on. He had to be gentler with her than Tom since his cock was thicker but it was great when she became used to it.

“Oh my god, I can’t believe it!” shouted Fred and stood up.

“What, what?”

“Honey, he wrote me. After all these years I have finally found my dad, and he sent a photo.”

“That is so cool, let me see.”

She placed the laptop on her lap and then looked at the photo. A knot formed in her stomach and she looked up at Fred with a weak smile.

“He is coming here next Saturday; can you believe it. Fuck, I’m so happy!”

“That’s great, honey. What’s his name?”

“Tom, Tom Davidson, and get this. He used to be a porn star, isn’t that crazy. He got my mom pregnant when she was just sixteen. My step-dad was cool with it and he was a great dad to me.”

“What was your mom’s name as single.”

“Barnes. Why?”

Cindy smiled up at him. “Oh nothing, honey, nothing at all.”