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Bo Peep and the neighbor

crossdresser role play
It had been a hot summer and I had no luck finding a job. My parents did not seem to understand that there just weren't that many companies hiring that year due to the economy so they had really been pressuring me to find a job. They all wanted someone with experience but having just graduated high school I had none.

I was nearly at my wits end so when I was asked to house sit for my uncle I jumped at the chance. He lived a half an hour out of town in a nice quiet neighborhood and had a nice place. He was going to visit a sick relative out west and would be there for at least a week. He needed someone to take care of his two little dogs for him. I packed a small bag and was on my way in no time.

I pulled into the carport and let myself in with the key he kept stashed in a paint can in the carport closet. I checked on the dogs and they were fine so I let them out to do their business and helped myself to a beer and had a look around. The front yard was small but perfectly manicured and the back yard was huge but he only took care of the first 50 or so feet and had enclosed that part with tall privacy fencing.

Inside the fence he kept his garden. He had a section to grow vegetables and had rose bushes all over the place in the rest of the yard with little walkways winding through. He was well known for his roses and had actually won some ribbons for them when my aunt was still alive. He grew them and cared for them and she got all the credit when she would enter them at the garden club shows. No one ever thought anything about a man being so into flowers; we all assumed he did it to please my aunt. After she died we assumed he kept them going in her memory. 

The inside of the house was typical of people their age with the 60's furniture and hundred of little trinkets gathered over their lifetime. I was going to have to be careful not to break anything. The spare bedroom was nice and the bed was sooo soft I lay on it to just chill for a little while. I pulled off all my clothes and got a pair of panties and a Cami top from my bag and put them on and hung out a while in my panties drinking beer. I was going to enjoy being able to dress in drag for a while without fear of being caught. That night I dressed up in my favorite slut outfit and played with my dildos until I was tired enough to go to sleep. 

The next morning I had a bath and put on my least slutty outfit to hang out in. I had breakfast and sat in the den to watch TV for a while. I ended up getting bored and started looking through my uncle's stuff. It was what I would expect from a man his age. Sports magazines, tools, ammunition for his many guns, pictures, etc... I went into the guest room and started rummaging through the large closet in there. Mainly old clothes and a lot of boxes in the back.

I was going through the boxes when a flash of blue caught my eye. In the back of the closet I found a blue dress and behind it a pink one and a yellow one. There were petticoats behind them and in one of the boxes I found panties, shoes, stockings and all kinds of other very dainty wear. I took the blue dress out and held it up in front of me. This might just fit me I thought. This was strange because I first thought this must all be my aunts old stuff but she was a very large woman and there was no way this would fit her. My uncle on the other hand was about my size and it just might fit him. Was my uncle a crossdresser too?

I pulled the dresses and boxes out of the closet and started arranging all the stuff on the bed. There was a lot of stuff there and they were not like the clothes I wore when in drag. My stuff was club wear and lingerie where this stuff was more for sissies. This was the kind of thing a little girl would wear. It did look pretty though and the fabrics were all soft and satiny and lacy. Of course I had to see if it would fit so I stripped off my slut clothes and tried a white pair of silk panties that had ruffles on the butt.

They did fit me but felt a little different than the panties I normally wear; the butt was tight and the crotch was loose. I wasn't tucked and my clitty rubbed the loose silk as I walked and felt awesome. Next I tried a white lace suspender belt and white lace topped stockings which also fit well. Next a white lace bra and some of the other panties stuffed in to fill it out. I noticed a blond curly wig and a blue bonnet so I decided to try the blue dress. First I put on a petticoat which is something I've never worn before. Then the dress went on. I looked in the mirror and realized this was a Little Bo Peep outfit. The wig and bonnet went on next and after some more looking I found another box that had more wigs and some make up in it. 

I took the box to the bathroom and after removing my slut make up started to apply the make up in the box. I used the foundation which was very light and the fake eyelashes. Next was pink eyeshadow and lots of blush and pink lipstick. I even made freckles with a pen I found in there. I went back in the bedroom for the last touch. A black pair of black Mary Janes.

I remembered seeing a light blue umbrella in the closet so I retrieved it and when it opened I saw that it had white lace trim and obviously went with this outfit. there was also a large lolly pop in one of the boxes. I grabbed it and the umbrella and stood in front of the mirror. I had turned into a little girl! An excitement I had ever felt before grew in me and I felt like skipping and giggling like the girl I was. So that's what I did. I skipped down the hall into the kitchen loving the way all the lace and silk felt on my body. The club wear I owned made me feel like a slut but this made me feel like an innocent little girl. I loved it! 

I went out back into the sunshine and sat on the back porch swinging my legs back and forth like a little girl and breathed in the fragrance of all the roses and other flowers and enjoyed for once not being a man or a cum loving slut but being a little girl. I skipped around the garden twirling the little umbrella and licking the lolly pop and stopped to admire one particularly beautiful rose. It was pink and big and smelled divine. I stood there quite a while touching it and smelling it and just admiring it's beauty when suddenly a hand lifted up my dress from behind and a large hand was between my legs squeezing by balls. 

Then a mans voice came from behind, "Bo Peep. Have you lost your sheep again?" 

Of course I was shocked at this. I had not heard anyone approach and did not expect anyone to be stopping by, but here I am dressed like a total sissy and there was a stranger's hand squeezing my balls. I didn't know what to do. I just stood there as the hand moved up to my clitty and started rubbing it through my panties. 

"What's wrong Peep? Cat got your tongue?

That's when it hit me. This guy obviously thought I was my uncle and apparently they were playmates. Realizing this I calmed down and as I turned to face him I said in my girliest voice "I'm afraid I'm not the Peep you are looking for."

The man was my uncles next door neighbor Hal. I had met him once years ago. He was a widower in his forties who worked from home. He was about 6 feet tall and about 180. He had brown short hair and no facial hair and was built pretty well. I thought he was going to pass out. He was more shocked than I was.

"I'm Jim's nephew Dave. He's out of town and I'm watching the dogs for him."

"I didn't know he was gone."

"Yes he had to leave suddenly, his cousin is real sick and he went to New Mexico to visit him."

"I see you found his fun clothes. Let me say that you look better in them than he does."

"Thanks, Hal is it? So you and my uncle are play friends?"

"Well, yes. We get together a few times a week. You ever play with other men?"

"Yes, maybe I can fill in for uncle Jim if you want?"

He explained that he and my uncle had been playing for years and that usually they did role play. My uncle would call him up and they would decide on a scene to play out then Hal would come over. They usually were scenes where he would catch my uncle doing something wrong then would discipline his "little girl" by spanking her and forcing her to suck his cock then he would fuck her. He said that he had seen the top of the little blue umbrella over the top of the fence so he figured my uncle was dressed up. He had decided to surprise him and improvise some hot role play by coming over and catching him off guard.

I had already decided I wanted some of this man so I immediately went into my role as Bo Peep.

"I'm sorry father, I didn't mean to lose the sheep again. Please don't be mad at me!"

He smiled briefly then with a firm voice said "now Peep we've been through this before. You know better than this. You know I must punish you for this don't you?"

"But father, I promise it won't happen again!"

"It Better not!" he scolded as he walked over tot he porch and grabbed a chair. He put the chair in the walkway and sat down. "OK Peep you know what to do. Get over my knee now!"

I slowly walked over and lay on his lap. He scooted me up so that my clitty was between his thighs. He raised my dress and petticoat and lowered my ruffled panties to expose my creamy white ass, then started spanking me with his bare hand. He swatted me hard, first on one cheek then the other, smack smack smack smack.

After a dozen or so swats he stopped and ran his finger up and down my ass crack, stopping to put pressure on my puckered little hole, then reached down and fondled my clitty before resuming the spanking. He spanked me for quite a while telling me what a bad girl I had been and that little girls who were naughty deserved to be punished. Every ten or so swats he would stop to fondle me and finger my hole. By the time he was done my clitty was hard and my ass glowed a warm red.

When he finished he told me to stand before him. He stood up and dropped his pants and boxers to his ankles then sat back down and spread his legs apart. His long cock hung between his legs, begging to be sucked.

"You know what to do little girl. Now get to it!"

I dropped to my knees and reached for his cock and he pushed my hand away saying "you know daddy does not like to get his pants dirty! Now take them off and fold them like a good girl!" 

I slipped his shoes off and set them aside then pulled his pants off and folded them and placed them on top of his shoes, then did the same with his boxers. I then leaned in and took his cock in my mouth. He was about six inches soft and was uncut. The taste of his cock and the smell of his musk was intoxicating! I pulled back the foreskin and licked his head like an ice cream cone.

I fondled his balls and took his growing member in my mouth and sucked until it was fully hard then took the whole thing down my throat. He started fucking my throat and telling me what a good girl I was to give daddy such pleasure. Tears were streaming down my cheeks as he rhythmically fucked his cock down my throat and back over and over again. He pulled out and told me to open wide as he stroked his now eight inch hard cock.

After a minute or so he shot his load in my mouth. I swirled it around in my mouth savoring the taste then swallowed it down. I took him back in my mouth and sucked him until I had gotten every drop then sat back and smiled at him. 

He took off his shirt and handed it to me. I didn't have to be told to fold it and put it with his other clothes. "That was nice Peep, now grab daddy's clothes and let's go in and get daddy something to drink" he said.

I picked up his clothes and followed him into the house. He sat on the sofa and told me to get him a beer. I handed him the beer and he told me to remove my panties and lay across his lap. I removed the ruffled panties and handed them to him then lay across his lap as instructed. he stuffed the panties in my mouth and lifted my dress and petticoat. He reached into his pocket and took out a small tube of lube and squirted some on my hole. As he drank his beer he worked first one then two then three fingers into my hole. He worked them in and out slowly while he drank. By the time he finished his beer my hole was gaped open and I was ready to be fucked!

He told me to get up and go into the kitchen. He followed me into the kitchen and had me bend over the table. It was a small table so my chest and tummy were on the table but my ass hung off one end and my head and arms hung from the other. He removed my stockings and garter belt and used the stockings to tie my ankles to the table legs leaving my legs spread wide then he used the garter belt to tie my wrists together. He then went to the hall closet and retrieved a long wooden paddle. 

"Now Peep, I'm going to allow you to have pleasure but first I must administer your final punishment," he said while rubbing the paddle up and down my ass cheeks. "You will count the strokes out loud; do you understand?

"Yes father," I replied.

The paddle made a loud smacking noise as he brought it down across my ass cheeks. It hurt so much that tears formed in my eyes, my ass burned terribly, and my face flushed red. Oooowww, I yelled, trying to catch my breath. I didn't know how many times he intended to hit me with that thing but I found myself hoping he would stop soon.

"I don't hear you Peep! How many was that?

"One sir!"


"Two sir!

He kept smacking me and I kept counting until my ass was numb to the pain and the adrenaline was coursing through my veins giving me an intense rush every time he would bring the paddle down on my ass. He finally reached twenty five and put the paddle down on the table. He gently rubbed my cheeks and probed my hole to make sure I was ready for him then came around to my face and pushed his cock into my mouth. I sucked him until he was hard and he walked around behind me and positioned himself between my legs.

He slowly pushed his cock inside me. Oh it felt so good! I love getting fucked when my ass is nice and warm from a spanking! He went all the way in and all the way back out slowly. Then all the way in again. He slowly pumped in and out building up speed gradually until he was fucking me pretty good. 

"Tell me how much you like it!" he said.

"I love having your cock in me daddy!"

"Now beg for it like a good girl!"

"Oh daddy I love your cock! Please fuck me with it! I love your big hard cock! Please fuck me harder!"

He pumped away and smacked my ass from time to time until I was ready to explode. He reached around and grabbed my clitty and I instantly spilled my jizz on his hand and the floor. My ass clamped down on his cock and that did it for him. I felt him filling my insides with squirt after squirt of cum.

When our orgasms had subsided he withdrew and told me to hold my hand under my hole to catch any that dripped out. I couldn't do so with my hands tied so I told him so. He untied my legs and hands and I stood up and held my hand under my hole. He told me to squat down and push out his cum into my hand. I squatted on the floor. I could feel my ass gaping open and when I pushed a gush of cum spilled out into my hand. I lifted my hand to my mouth and licked it all up then dipped my fingers in my ass to get any that was left. I licked my fingers clean then he gave me his cock to clean. When I had him clean we kissed before he got dressed and went home.

I ended up staying there another five days after that and we played every day or night. We did Little Red Riding Hood, Alice In Wonderland, I dream of Jeannie, and the last night I took control and dressed in my sluttiest outfit so he could see what a real cum slut looked and acted like. I didn't say anything to my uncle when he returned but Hal must have. I got a call from him a few days later and he asked me if I'd like to come visit for a few days. Of course I did but that's a whole different story.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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