The Homeless Peeper

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Life was hard. I was 18 and out in the world by myself. My home life was not a pleasant situation. My Dad beat my Mom and if I happened to get in the way, he’d pound me to a pulp. I left home when I was 14. I wanted to stay and help my mom but I just couldn’t take it anymore. I love my mother dearly, but I just couldn’t handle it.

I got by pretty well for a homeless kid. I ate scraps that restaurants threw out. I’d found some pretty swanky restaurants that tossed out some near full meals that customers hadn’t eaten. I would encounter cooks taking smoke breaks in the alley and I got on good terms with them. About once a week I’d find a complete meal in a Styrofoam container. I got clothing from a homeless shelter and I was always able to find someplace dry to sleep.

During the day I would stay downtown by the river and entertain myself. There was a lot to do. In the evenings I would wander the streets looking for my lodging for that night. It wasn’t the greatest life, but it was certainly better than being beaten by that asshole I lived with. Everyday I thought about my mother and wondered how she was doing.

Today I did something different. I got on our LRT system and rode out to the suburbs. I hadn’t been in the ‘burbs for more than 2 years and I was curious to see how things had changed. I was lucky that I didn’t run into a transit employee because I hadn’t bought a ticket. I rode for about 45 minutes and then got off at a random stop near a residential neighborhood.

I wandered around looking at the houses. There was quite an assortment; they ranged from pretty average looking streets to some fine looking houses. I stayed mostly in the nicer areas. A kid likes to dream, right? I had been wandering for quite a while when I saw the sun was starting to set and I hadn’t found a place to sleep yet.

I stopped being a house voyeur and looked for a place to rest for the night. I found a park in not too much time at all. I loved that about suburbia; there were parks and schools EVERYWHERE. I looked through the park for a secluded place where no one would notice me. I learned very early in my homeless days that most people didn’t like vagrants hanging around their neighborhoods.

I came upon a wooded area and thought it would be perfect. The sun had set now. I settled down for a rest; I had been on my feet for hours without sitting down. I rested for a bit and then went off in search of dinner. I took notice of exactly where I was so that I could get back to my sleeping area.

I was walking through the woods when I saw a house with lights on the bottom floor. I went a bit closer and was shocked at what I saw. There was a pretty woman standing in her bedroom – NAKED. I had never seen a naked woman before. Since I left home my life had been about survival; I had not even THOUGHT about sex. Even when I lived at home I rarely thought about it. Sure I was fourteen when I left, but my thoughts were more along the lines of exacting revenge on my abusive father.

But here was this beautiful woman not 50 feet away from me. I had to get closer. I crept through the trees to her yard. There was only a small fence so I was able to leap over that quickly. Now I was about 30 feet away from her. There were some shrubs in her yard and I concealed myself behind them while I snuck closer. I could see a lot more now.

She was putting some kind of powder all over her body. She was facing away from me, but I could see her reflection in the mirror. She had pretty big breasts and an hourglass figure. As she patted the powder on her form her hips swayed back and forth as if she was keeping a beat. This was the coolest thing I had ever seen. I looked down and saw my dick was hard as a rock. THIS hadn’t happened for a while. Back to her.

She finished applying the powder and turned around. My heart stopped. What if she saw me? I ducked behind the shrub and stayed there until I felt it safe to look. After a few minutes I looked around the bush and my world darkened. She was gone! The lights were out and she was gone. I waited for some more time before I got up to go. I had to come back here. I snuck around to the front of the house and took note of the address.

I went back to my sleeping area and crashed for the night. I hadn’t had any supper, but that was nothing new. I’d live.

I had a pretty good night and woke up at sunrise. I went about my day as usual, wandering around, looking at houses and looking for food. Not too far from the park I found a restaurant and was able to score some scraps to fill me up. Nighttime came and I went back to my woman’s house. There were no lights on so I was able to get closer and look directly in the windows.

There were three bedrooms on the main floor and the kitchen. The three bedrooms were easy to identify with the contents; the master bedroom, the daughter’s bedroom and the son’s. The master bedroom had a big bed and a jetted bathtub in the en-suite. The daughter had typical daughter stuff in it; a few dolls, some posters of rock bands and 2 a frilly bed. The son’s bedroom was all about sports. I spent most of my time looking into the master bedroom. I was looking at the big TV sitting on the dresser when the light came on. I hit the dirt fast.

Soon I heard the water in the tub go on and rose up a bit. She was in the bathroom. I slowly made my way over to the bathroom window and got there just in time to see her unfastening her bra. She put in on the counter and stretched her arms over her head. They were perfect; big breasts with hard nipples about as wide as my thumb. She got into the tub, turned the jets on and adjusted her position a few times. She sat there and soon I could see her hand dart down. She was masturbating. My cock was harder than yesterday and I took it out to play with it. She kept playing with herself as the jets roared away. Soon her hips began to buck and I realized that the jets were aimed right at her pussy. She was using THEM to masturbate with as well. My cock started to spew its load. It hit the lower left window pane and slowly dribbled down. She came too and I knew it was time to get out of there.

Just as I turned to go back over to the bedroom the light in the daughters’ room flicked on. I had to at least look.

I surreptitiously edged up to her window and peeked in. She was as hot as her mother – and equally as naked. She had VERY perky boobs with pointy nipples and a blonde pussy. I guessed she was a bit over 5 feet tall and rather curvaceous. She walked over to her bed, sat down and removed something from her bed-side table. It was a dildo.

She laid back and traced lines around her nipples with the dildo. I couldn’t hear if it made a noise, but I suspected it didn’t. She dragged the dildo down her body to her pussy and teased her pussy lips with it. She did this for a while before slowly sliding it into her wet pussy. She started out slow; in and out, in and out, in and out. By this time I had another raging hard on and I was beating my member along with her. As the minutes moved by her actions sped up. Just before she clamped her knees together she was pounding the dildo into her at a ferocious pace. When her orgasm hit, her knees snapped together and she quivered and shook for 10-15 seconds. About now my cock erupted for the second time tonight and spewed its lava on the lower left part of her window. I put my weapon away and got out of Dodge.

The next day went by quickly. I played in the park for a while, talked with a few people that came by and waited for night to come. I was again there before they went to their rooms and had the same seat as the night before at the master bedroom. Tonight I noticed a clock in the corner of the room. At 9:00 PM the light flicked on and she entered. Just as the previous night she disrobed and ran the bath. I hid myself better today and was able to watch her take off her dress and bra. She wasn’t wearing any panties. I slid over to the bathroom and watched her get in the bath. Again today, she settled down and started to masturbate in the tub. But today was a little different. Part way through she got up and took something out of the drawer and sat on the edge of the tub. It was a dildo.

‘Like mother like daughter,’ I thought.

She didn’t tease herself like her daughter; she started pounding her pussy immediately. She was facing the window as she plowed herself so I had to very careful not to be seen. I had my cock in my hand and was sliding my right fist up and down. I had not masturbated much at all in my life, but it seemed to come very naturally (no double entendre there, is there?). As the mother fucked herself I was getting more and excited and in a matter of minutes shot my wad on the lower left window pane. There was still a cum trail from the day before and I added more. The mother came in short order and relaxed in her bath. I watched the sexy goddess for a while and then moved over to the daughters’ room to see if there was going to be a show tonight.

There was no light on, but I decided to wait. It’s not like I had anything better to do. I sat there thinking about the good fortune I had run into and was lost in fantasyland when the light was flipped on. In came the daughter. She was wearing tight sweat pants with ATLAS HIGH across her ass. She had on a tight pink shirt that showed off her bosom handsomely. She got out her iPod and sat on her bed listening to music. As she listened she would occasionally rub her breasts with both hands. She sat propped up against the wall moving her upper body to the beat. Soon her hands began to caress her legs and inner thighs through the sweats. She rubbed her legs up and down, sometimes touching her pussy area. This went on for some time before she put both hands into her sweats and began rubbing her pussy. Of course I couldn’t see exactly what she was doing, but she came soon as did I; spraying my line of cum on the lower left part of HER window, too.

This went on for about a week. Every night I’d go and watch the two sexy ladies. They didn’t masturbate every night, but I sure did; always depositing my cum in the same place – the lower left pane or the lower left part of the window. They were so sexy. They didn’t even have to get naked to get me excited. At the end of the week my life changed.

It was Thursday and I had just watched to mother have her bath. She didn’t masturbate tonight, but it was still an incredible time. I had just moved over to the daughters’ window when I heard a noise beside me. I spun around and there she was – the mother.

I turned to run, but she had a hold of my hair before I could move.

“I don’t want to scare my daughter. Come with me peacefully or else,” she said.

I complied.

We entered her back door and went to her room. She shut the door and pushed me into a chair in the corner. She looked at me with an icy glare.

“Care to explain?”

I sat there silently. I couldn’t think of any words.

“I know you’ve been watching me. I found the mess you made on my window. I don’t mind so much for me, but when I found your signature on my daughters’ window that was too much.”

“I’m sorry,” I stammered.

“I need more than that, young man. I can pick up the phone and call the police. I have no problem doing that.”

“I’m sorry,” I said again.

“We’ve covered that.”

“I…I…I’m sorry, ma’am. I just came out here from the city and I don’t have anyplace to go. I saw you a week ago and you’re just so sexy. I’m sorry.”

“You have no place to go?”

“No. I sleep in the park. Please don’t call the cops. I didn’t mean to hurt anybody. I’ll leave. You’ll never see me again. I promise.”

“You sleep in the park? Don’t you have a family?”

“Yes, but I ran away 4 years ago. My dad beats my Mom and me. I couldn’t take it.”

As I spoke her bathrobe opened slightly and I could see the upper part of her huge right breast came into view. I couldn’t avert my gaze. She noticed where I was looking.

“What do you eat?”

“I get scraps they throw out at restaurants.”

“Are you hungry now?”

“I’m always hungry but I do okay.”

“Wait here.”

She left the room and I sat there. I was truly scared. In a few minutes she came back, carrying a sandwich.

“I hope you like peanut butter and jam.”

“For me?”

She nodded and handed me the sandwich. I ate it in seconds.

“Thank you, ma’am.”

“Tracy. What’s your name?”


“And how old are you, Don?”

“I’m 18.”

“Well Don who’s 18, it seems we have quite a dilemma, doesn’t it?

“What’s a dilemma?”

“A problem.”

I didn’t know what to say.

“You have no place to go and I can’t let a young man sleep in the park. I can’t let you sleep here either. I don’t know you. I feel for you, though. You’ve been through quite a horrible ordeal. I can’t imagine what it was like.”

“It wasn’t fun.”

“I’ll bet. I’ll tell you what. There’s a motel a few miles away. Can I get you a room there and you can stay there for a while.”

“You’d do that for ME?”

“Money’s not a problem. My husband died 3 years ago and he had lots of life insurance. I’ll get dressed and drive you there.”

She rose and walked to the closet but before entering she turned around and her bathrobe hit the floor. She was naked in front of me. I was awestruck. She turned in a circle before going into the closet and getting dressed. She came out, went to her kids’ rooms to tell them she was going out for a bit and led me out to her car.

We got in her Cadillac Escalade and she drove me to the Budget Inn Motel. Along the way I had visions of her standing naked in the closet door running through my head. We arrived and she got me a room.

“You have a good sleep, Don. Can you get back to my place?”

“Yeah. You’re at 14756 XXXXXXX Pl. (I keep this out to protect the innocent/guilty)”

“You come back to my window at 1:00 tomorrow afternoon.”

“I don’t have a watch.”

“You just find a clock somewhere and be back at my window at 1:00 tomorrow.”

I agreed. Tracy turned to leave and put a twenty on the bed.

“This is for a bit of food tomorrow.”

“Wow. Thank you, Tracy.”

I had the best night I’d had in over 4 years. I slept in a bed for the first time since I left home. It was great. Usually I jumped in ponds late at night to clean myself, but today I got to have a shower. I ate a bit of food. I didn’t have too much because I wanted to make the $20 last. After I had some lunch I saw from the clock in McDonald’s that it was12:15.

I walked back to Tracy’s. I was surprised at how easy it was to find her place. When I go there I didn’t know what time it was so I went in the park. I saw an elderly man and asked him. He said it was 12:50. I waited for what seemed like about 10 minutes and went back to Tracy’s house. Just as usual I crept through her yard and up to her window. When I got there I saw Tracy – naked on her bed. She was bouncing up and down on her dildo. Her big boobs were bouncing with her. She saw me and smiled, but didn’t stop. I stood there mesmerized. Tracy continued to ride her dildo. She made a fist and moved it up and down.

‘She wants to watch ME jerk off, too,’ I thought.

I pulled my pants down and started stroking my cock. Tracy pointed to the right and I moved. I was in the middle of her window, jerking off and watching her ride her dildo. This was the coolest thing EVER. Tracy began to scream and came hard. I was still pulling my guy. She recovered and came to the window. She got down on her knees, opened her mouth and pushed it up to the glass. I shot my load. It would have splattered all over her face if not for the glass. Tracy moaned so loud I could hear her through the window. She motioned for me to come in. I did.

Tracy met me at the back door.

“Fuck that was hot, Don. You’ve probably figured out that I’m quite the exhibitionist, haven’t you?”

“I didn’t know it was called that, but I sure do now. That was incredible.”

“This had been a fantasy of mine for a long time, Don. I’ve always wanted a horny young guy to watch me masturbate. I’ll pay for you to stay in the motel and we can do this every day under ONE condition.”

“What’s that?”

“You stay AWAY from my daughter’s window. You can watch me all you want, but you stay away from Monique.”

I agreed and we talked for close to an hour about lots of stuff. She was very interested in what I’d done to survive for the last 4 years.

“Time to go. My kids will be home, soon.”

She gave another $20 for food and told me to come back the next day at the same time and any other time I wanted. This was so cool.

I stayed in the park for the afternoon and when dark came I went back to the house. I sat under the window and waited for Tracy to enter. When she did I stood up with my cock in my hand and began masturbating. She didn’t see me right away but when she did she smiled and ripped her clothes off. We came close together with my cum spraying all over the center pane. Tracy jumped up and pretended to lick my cum off the glass.

It went on like this for a little more than two weeks. Some days we’d talk; other days I’d just masturbate and leave. Tracy’s window had cum all over it; we never cleaned it off.

It was a Tuesday and I was standing outside Tracy’s window masturbating as usual when she started motioning for me to come in. I left my dick hanging out and walked into her house. As soon as I entered Tracy was right in front of me.

“Today we’re changing things a bit.”

“Really? How?”

“You’re going to fuck me, Don.”

And with that Tracy dropped to her knees and took my cock into her mouth. She sucked my cock for a while, rose and pulled me into her bedroom. She flopped on the bed on her back and spread her legs.

“Take that magnificent cock of yours and cram it in my cunt!”

She didn’t need to repeat herself. I almost dove on top of her and rammed my cock into her inviting pussy.

“Uuugggghh!” she moaned. “Fuck me Don. Make me your slut. Fuck me hard.”

I ground my pelvis into her, driving my cock in as far as I could.

“Damn you feel good, Tracy.”

“Stop your talking and fuck me, Don. I haven’t had a cock inside me since my husband dies. You’ve got three years of pussy aches to heal. Get fucking!”

I drove my cock in and out of her as hard as I could. She grunted with every stroke. Tracy had quite the mouth on her.

“Fuck me luck a horny slut, Don. I’m your whore. Punish me for making you jerk off on my window for a month.”

I loved her dirty words.

“Stop, Don! I want to get on top and ride your cock like I’m a bronco rider.”

I rolled over and Tracy mounted her steed. She bounced up and down just like I’d seen her do with her dildo.

“Oh yes, Don! This is it! I want this! Yes! Yes! I’m cumming! I’m cumming! Yes! Oh, yes! Oooooooooooh!”

And with that she collapsed on me. I was still moving my cock in and out.

“Don, that was wonderful. Let me taste you. I want you to cum in my mouth.”

She pulled off my cock so fast there was a small popping sound. She immediately took my cock in her mouth and sucked me with abandon.

“Oh yes, Tracy! Suck my dick! You’re so good! Suck me!”

Her head bobbed up and down fast. I knew I was not going to last long at this rate. I felt it happening.

“Oh, Tracy! Here it comes! I’m cumming!”

I filled her mouth full of my demon seed and she moaned with every squirt. When it was done she moved up and opened her mouth to show me all of my cum inside. She closed her mouth, smiled and swallowed.

“Fuck, Don. Your cum tastes so sweet. I love it.”

We laid on her bed kissing and fondling each other until it was time for me to go.

Our relationship progressed and over the next few months we had sex almost every day. Then one day when we were done we were talking afterward.

“Did you go by Donny when you were younger?” she asked.

“Yeah. Why?”

“No reason. I was just wondering.”

She asked me a few more questions and then we fucked again.

The next day we fucked harder that usual. Tracy had started having me play with her ass a few weeks before and this day she took my dick in it. It was a bit painful for her, but by the end she was loving it. I came inside her ass and we both screamed with pleasure. When it was time to part she asked me to come to her front door the next day.

The next morning at 11:00 I rang the bell and Tracy answered.

“Come in and sit in the living room. I have a surprise for you.”

I sat and she left the room. In a minute or she came back and I was turned looking out the window.


I knew that voice. My head snapped around.


She was in tears. I ran to her and threw my arms around her.

“Oh, Donny. I thought I’d never see you again.”

Now I was in tears, too. “Mom… oh, Mom.”

Now Tracy was crying. Mom and I hugged for what seemed like forever. When the tears had subsided we sat on the couch.

“Mom, you look so good. But what about him? Is he still…”

Mom cut me off. “He’s in prison, Donny. When you left that was the jolt it took for me to get help. I had him arrested the next day and within 6 months we were divorced. The courts gave me everything. I sold the house and moved to this part of town. I’m just so thankful that Tracy said something about you to me. How do you know Tracy?”

This was something I should have been expecting but it never dawned on me. I looked at Tracy. She shrugged.

“I used to walk her dog for her.”

Mom turned to Tracy.

“I didn’t know you had a dog. When did you get it?”

Now Tracy was on the hot seat.

“Uh…we only had it a few weeks. Turns out Monique was allergic. We had to get rid of it.”

We looked at each other with a knowing glance.

I left the motel and moved in with Mom. We had 4 years to make up for. I still saw Tracy, but not every day. To this day Mom has no idea that I’m boning her best friend.