Role Playing Ch. 06: Homeless

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Woman helps homeless man.
2.5k words
4.48
9.1k
14

Part 6 of the 9 part series

Updated 06/11/2023
Created 08/23/2022
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ROLE PLAYING 6, HOMELESS

I was sitting on the sidewalk. It was night and I was huddling in my old jacket, trying to keep warm. My wife and I were doing another role-playing adventure. She had come up with the idea of me being a homeless person and she being a 'do-gooder' who wanted to help the less fortunate. I didn't know what she had planned, but I eagerly wanted to find out.

She walked up to me and said, "Hello Raymond (not my real name). How are you tonight?"

I said, "Hello, Miss Sally (not her real name either). I okay, I guess."

She said, "I brought you some food and some things to help you clean up." She had a big shopping bag full of stuff.

She went on, "I brought you some new clothes to replace those dirty things you are wearing."

I said, "Thank you. You are very kind." I looked down shyly.

She said, "I think I have things that will fit you. You are about the same size as my husband so I took some of his older things." She removed a shirt, pants, socks and underwear from the bag.

I said, "Thanks. I'll put these on after you're gone."

She said, "You need to clean up before you put on these clean clothes." She had a small basin and a couple of bottles of water. I wasn't sure what she was going to do.

She instructed me to "Take those old things off and we'll get you cleaned up."

I asked, "You want me to undress here?"

She saw my point about stripping on a public sidewalk, so she suggested we walk to a nearby park. It was dark and the park was empty. We found a secluded spot next to a small creek that ran through the park. I was eating the fried chicken she had brought me. When I finished a couple of pieces, she stopped me.

"Okay, give me those old things." She said.

I said, "You want me to take my clothes off in front of you."

She said, "If we're going to clean you up, yes."

I hesitated until she said, "If you'd rather not, I'll take this stuff back home."

I reluctantly said, "No, no, I'll do it."

I pulled off my greasy jacket and then pulled the sweater I was wearing over my head. My undershirt was next. She took the items and put them in the bag.

Miss Sally dipped some water from the creek into the wash basin she had brought. Then she wet and rubbed a bar of soap on a washcloth and stood beside me and washed my back, my chest and under my arms. Having her hands rub the cloth all over me felt really good in the cool air. She took another cloth and washed my neck and face. It was cool and I was naked so the cool water was exhilarating to say the least. I lifted my arm and she washed my armpits.

"You need a shave." She said. She had a razor and shaving cream. "First, let's finish washing you."

She looked down, obviously wanting me to take off my pants. I kicked my shoes off, then dropped my pants which were held up by a rope. I had to put my arm on her shoulder to keep my balance while I removed my dirty socks. I could smell her wonderful scent.. Then, with a deep breath, I pulled my underpants down. I stood before her buck naked.

She put more water in the basin and got another rag. She went down on her knees and washed my legs and moved up to my waist. She took her time washing over my bare ass. Then, she started to wash my cock and balls. I immediately got hard.

"I apologize for getting hard. It's been a long time since a woman touched me there." I meekly said.

She said, "That's okay, it's nothing I haven't seen before."

She washed my prick and balls with the damp cloth and as the water evaporated in the cool air, I really felt good. She continued to wash me. She got more water from the creek and poured it over me to remove the soap. The cool water gave me goosebumps. She got me to bend over so she could wash my ass. It was embarrassing, but when she rubbed the wet cloth between my legs, I lost my inhibitions and let her do whatever she wanted. She pumped my dick with the cloth, getting it much cleaner than any other part of my body. I was close to coming when she stopped.

"Let me shave you." She said.

I knelt in front of her, both of us on our knees. She lathered up my face and began to use the razor on my face. I was looking right into her eyes and I smelled her perfume and the shampoo in her hair. This was amazing. I could see down the front of her blouse to where her breasts started to curve out. I wanted to put my face in there and smell her intoxicating scent. She must've read my thoughts because she pulled my head into her chest and rubbed the washcloth in my hair. My nose and face were touching her soft skin and inhaling her perfumed scent. I let her run her hands through my hair while I tried to catch a glimpse of her nipples. I stared down her blouse at her pink breasts moving with her breathing. I wanted to just lose myself in her cleavage.

She finished shaving my face and then had me lift my arms. She shaved under my arms, something I had never done myself. Kneeling with my arms in the air and by dick standing out in front of me was really erotic. My dick was ready to pop-off by itself.

Then she told me to stand up. I stood in front of her, with my dick at her eye level.

"For good hygiene, I should shave you down here too." She surprised me.

Before I could even respond, she had lathered up my pubic hair with shaving cream. She rubbed it in thoroughly and stroked my dick with the shaving crème in her hand and then took the razor and started to shave me.

'Be careful, please." I begged.

She said, "I'll be careful, but I need to be sure I get everything." She lifted my balls and ran the razor over them. The sharp blade on the delicate underside of my balls scared me. She even shaved my cock, even though there was no hair on it. She lathered up my dick with her hand and then ran the razor over my skin. She shaved all of my public hair, leaving me bare. My cock was so hard, I thought it would burst.

"Oops. There's a small nick."

She had drawn a little blood. She licked the underside of my prick with her tongue to remove the blood. This woman was sucking blood from my cock. I couldn't help myself any longer. My cock blasted a wad of semen and it hit her on her nose. The second spurt hit her chin and the rest went onto her hand.

"You nasty old man." She said, acting offended. "You shot your filthy semen on my face."

I started to apologize, "It was an involuntary reaction. I'm sorry. What you were doing felt so good that I couldn't control myself. I haven't been with a woman in years."

She said, "You disgusting old man, you should be ashamed."

I decided to flip the script a little and said, "You should've known you'd make me come, playing with my cock like you did. You're the one who should be ashamed."

I went on saying, "You are taking advantage of a poor homeless person."

She blushed and started to get to her feet, but I pushed her onto her back on the grass. She acted shocked, but let me push her down.

I grabbed her legs and reached for the waist of her slacks. I pulled them off, along with her panties, exposing her pussy.

"Hold still while I shave you." I said.

She started to get up, but I held her legs. I quickly lathered her pussy with shaving cream and took the razor. With the razor near her delicate parts, she didn't dare move. I carefully began to run the razor over her pussy, removing her blonde bush. One stroke, then another exposed her bare skin where her pussy hair had been. I pulled her legs up and shaved between them, alongside her labia. I was very careful not to nick her. She laid there compliantly, letting me finish.

I leaned back to observe my handiwork. Her cunt was shaved clean for the first time. I liked it with hair, but the thought of shaving her was sexually exciting and my dick was hard again.

"Oops. I nicked a spot. Let me clean it up."

I hadn't nicked her, but took the opportunity to lick her clit and then I moved down to lick the opening of her vagina. She arched her back and put her hand behind my head to hold me there. I licked her pussy clean, tasting the shaving cream that was still on her cunt. She was spasming and lifted her pelvis up in her orgasm. I held onto her ass and kept my face in her cunt, rapidly licking to keep her orgasm going. She really liked felling my smoothly shaved face nuzzling her smoothly shaved cunt. She jerked as she came.

She was starting to calm down when I moved up and slid my cock into her with one thrust. She gasped at the intrusion. She still had her top on. I roughly pulled her blouse and bra over her head, leaving her naked beneath me. I put my face into those tits that had tantalized me a few minutes earlier. I bit her nipples and held them in my teeth for a few seconds each. She yelped at the pain, but continued to come.

"Miss Sally, you sure know how to help the needy and I needed a piece of ass." I said.

She looked up and said nothing as I continued to fuck her. I leaned down and kissed her, sticking my tongue in her mouth. She was beautiful laying there in the moonlight with her pretty breasts moving with my thrusts into her pussy. Finally, I produced another load of cum. I emptied into her wonderful cunt. I continued to pulse to get all of my semen into her. She laid there. I leaned back and looked at her nude body, laying in the grass, with semen starting to drip from her cunt. My earlier load was still on her face.

She hadn't planned on me turning the situation in my favor and fucking her like I had done.

While she was starting to recover, I had to take a leak, so I walked over to some bushes and relieved myself. When I turned around 'Miss Sally' was gone. I looked and saw her running away. I didn't understand until I realized that she had quickly dressed and had taken my clothes, both the old and the new set. I was stranded naked. I remembered that she had met me on the sidewalk a block away, but I didn't know where she had parked. I couldn't walk out on the street naked anyway. I didn't know what to do, but damned if I didn't have another hard-on.

I carefully walked to the edge of the park, moving from behind one bush to another. I looked for my wife, "Miss Sally", but she was nowhere to be seen. I guess she thought it was funny leaving me exposed after I had stripped her in public a couple of times. But society is much more tolerant of naked women than of naked men. If I were caught, I could be in serious trouble. I could be arrested and lose my job.

My fears were realized when a couple walking by the park saw me. The woman called me a flasher and a pervert and her companion turned them around and started to walk the other way, saying he saw a policeman at the corner. "Oh shit." That's all I needed was to get arrested for public indecency. Where was my wife. I watched as the couple walked quickly looking for a cop. There were two other couples and a group of three men walking my way from different directions. The men would probably kick my ass if the cop didn't get me first. I was almost in a panic.

Then, thankfully, I saw my wife's car driving down the street. She waved as she drove right by me. I had stepped out onto the sidewalk to meet her, which exposed me to the other people on the street and a passing car. My wife kept going, driving by and leaving me naked on the sidewalk.

Fortunately, she saw trouble coming for me and did a U-turn at the intersection. She drove back and pulled to the curb, on the opposite side of the street.

"Run for it honey." She yelled from her open window. She could've at least pulled onto my side of the street. I couldn't quibble so I ran across the street, completely naked, with more than half-a-dozen people watching. I tried to run, but the stones hurt my feet, so I had to step carefully. My dick was bobbing and my little nipples were hard in the cold night air. The cool air, or maybe it was the embarrassment caused my dick to shrivel a bit. I heard the people behind me talking when they saw me.

I got to the car, but the back door was locked. My wife fumbled for a few seconds to find the button to unlock the doors. That left me exposed even longer, and I was under a streetlight. I opened the door and jumped in the back seat. My wife slowly drove us away. I looked back to see a police car come around the corner, just missing seeing us.

"You nasty bitch, leaving me like that." I was laughing and regaining my breath.

She said, "You like to get me naked in public. How do you like it?"

I said, "It's not the same. Women like to be watched; men like to watch."

She said, "Oh really. Well, I sure liked seeing you prance around with your cock bobbing and all the people watching."

I had nothing to say in response to that.

As we drove off, she threw some clothes back to me and said, "Well Raymond, I'm going to drop you at the homeless shelter unless you have somewhere else to go for the night."

I replied, "Well Miss Sally, why don't we go to your house."

She said, "Hmm. That's an idea. I could nurse you back to health. It might take all night."

I said, "What about your husband?"

She said, "Fuck him."

I said, "That sounds like a fabulous idea."

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AnonymousAnonymousabout 1 year ago

More playful than erotic, at least for me. I was hoping the wife would have an encounter with an actual homeless guy, and take care of his needs beyond food and clean clothes. Oh well.

Wilson SpaldingWilson Spaldingover 1 year ago

If Bing Crosby and Grace Kelly played exhibitionist games, it would've looked like this...

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