A New Awakening

[ Mg, tg, 1st, anal, oral, ped ]

by Damien

damien78x@yahoo.com

Published: 9-Feb-2013

Word Count:

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Disclaimer
This work is Copyrighted to the author. All people and events in this story are entirely fictitious.

Let me start off by telling a little about myself. My name Derek and I am a 35 years old single male. I'm 6 feet tall, 190 lbs, blue eyes and short dark brown hair. I do home remodeling and as a hobby, I buy, fix up and sell houses. In the middle of January 2012, I bought a house, gutted it and remodeled it. When spring came, I turned my attention to fixing the outside. As I stood there looking at the new siding I finished putting on, my neighbor, Cindy, stopped over to ask me if I could fix her kitchen floor. She's very sweet and pretty, so I said sure.

The following Saturday, early in the morning, I started on her kitchen floor. About 8 am, she came into the kitchen with her 8 year old daughter and gave her a bowl of cereal. She's about 3.5 feet tall with a petite figure, pale skin and extremely cute. She has green eyes and short brown hair. She had on a pink tank top and short silk pajama shorts.

"Riley, I'm going to take a shower. Don't get in Derek's way." Cindy said.

Riley nodded and continued eating her cereal.

"Hiya, Riley, how are ya?" I said.

"I'm fine," she said.

"That's good," I said.

Every so often, I would catch a glimpse of her staring at me. I am a good looking guy and in good shape, but I just figured she was watching what I was doing. She got up from the table, walked over and placed the bowl in the sink. I turned my head and smiled at her. She smiled back and as I looked away, something caught my eye. I looked back at her, but she had already turned and began walking away. I couldn't help but look at her little ass as she walked out of the kitchen, I was surprised it had a nice heart shape to it, especially for a young girl like her. I shook the vision from my mind and went back fixing the floor.

Every so often, Riley would peek around the doorway and watch me. A couple hours later, she walked in the kitchen, I turned my head and looked her up and down. She wore a tight white tee shirt and a black skirt with black knee high stockings. She smiled at me as I checked her out. She then opened the refrigerator door and bent over. I quickly looked away. I heard the door close and she walking away. I thought it was cute how she was showing off, but it weird me out.

Shortly after, I finished the floor and Cindy walked in.

"Floor is done." I said.

"Oh great! Thanks Derek! What do I owe you?" She asked.

"Nothing." I said.

"Oh I must pay you." She insisted.

"I have a small garden and several flowers that need to be planted. If you plant them, we'll call it even." I said.

"Okay, deal. Riley and I will come over tomorrow." She said.

It was 10am when Cindy knocked on my door.

"Derek, can I ask you for a favor?" Cindy asked.

"Sure you can." I said.

"I just got a call that my mom is in the hospital, so can you watch Riley?" She asked.

"Sorry hun, I hope she's okay and yes, I'll watch Riley." I responded.

She smiled and said, "Thanks so much! Riley will be over soon and I should be back by 4pm."

"Okay, no problem." I said.

Short time later, Riley came over while I was in my backyard raking.

"Hey Derek."

"Hi there, Riley. Ready to plant some flowers?"

She nodded and walked over to me. She wore a light blue sundress that went to her knees and flip flops. She looked adorable and in her hair, she had two flower hair pins.

"I'll show you how with the first plant, then you can do the rest."

She watched as I dug a hole with a small shovel, placed the plant in, cover the dirt back over, pushed down a bit then gave it water using a watering can.

"Got it, hun?" I asked.

"Yep!" She said.

She kicked off her flip flops, lifted her dress a little and sat down on her knees. She then planted a flower perfectly.

"I'll be in the house, come get me when you're done, sweetie." I said.

She smiled and said, "Okay, Derek."

About an hour later, she walked to the room where I was.

"All done, Derek." She said.

I turned around, she stood at the doorway, her hands, feet and knees covered in dirt.

I giggled and placed the paint brush down. I then said, "Lets go get you cleaned up."

I led her to the bathroom and turned on the sink. I squirted soap on her hands and she placed them under the facet. She wasn't doing a great job, so I helped her. She had cute little hands with short nails that were painted pink. It was tough getting the dirt from under her nails.

"I'll get the dirt from under them later, I have a nail file at home." She said.

"Okay, now for your feet and knees...sit on the edge of the toilet cover, please." I said.

I grabbed a towel and a washcloth. I knelt down in front of her and laid the towel over my knee.

"Place your left foot up on my knee." I said.

She did as I said and I started to clean her foot which also had pink nail polish. Since her knee was elevated, my eyes were drawled to between her legs. Her dress rode high, giving me a small view between them. She wore blue panties with tiny flowers on them. I tried not to look, but every so often I would take a peek. After I was done with her little feet, I moved up to her knees. I noticed she had dirt marks closer up between her legs. I moved up her right thigh and as I came to mid thigh, she spread her legs and slid her dress up, leaving me full vision at her crotch. I then felt my cock stir in my pants.

I tried to hide the fact I was staring, but something didn't look right. I thought the light overhead was playing tricks with my eyes. I moved my head to get a different angle and still saw something. It was a tiny bulge, I could see an outline of a small penis head and ball sack. I was taken back, but I kept my cool. I slid further up her leg, an inch from her panties and wiped.

She had little dirt in the crease of her crotch and as I was wiping, her panties started to lift up. The tent in her panties stood up about two inches. I was shocked, I would have never guessed she was a boy. She looked like a girl, from her face to her figure and she sounded like a little girl. I wasn't disgusted, I wasn't going to judge her, I just figured she was more comfortable living as a girl and I wasn't going to treat her any different.

I noticed that her little boner pushed her panties away from her creases. I couldn't see her penis or balls, but there was room to wipe. I was wiping her left crease when I slowly moved closer to her penis. I slid under the side of her panties and as I gently wiped her little penis jumped a few times. It was cute.

"Sweetie, I can't clean you good. Can I remove your panties?" I asked.

She nodded and said, "Yes."

She held up her dress as I grabbed her waist band and she lifted. I pulled her panties down and when it passed her penis, it shot straight back up. It was little and cute. It was two inches long and a half an inch thick and circumcised. The head of her penis was light red in color, whereas the shaft and ball sack were her skin color. The sack was small and also tight, as she was very aroused. She was completely bald too. I removed her panties and placed them on the floor.

"Lemme rinse the cloth and warm it up." I said.

She smiled and said, "Okay."

I knelt back down and she watched as I gently began wiping around her penis and balls. Her penis jumped as I wiped around the base. I then slid up the underside of her shaft, over the head and then down the other side. I slowly wiped over her ball sack and began massaging along the sides. I noticed her breathing picked up as her tummy went in and out faster. I then slid the washcloth over her shaft and began stroking her with my index, middle, and thumb. I looked up and saw she was watching my hand stroke her. She began thrusting her hips forward while flexing her pc muscle. I could felt it jump as she did.

"Oh Derek!" She moaned.

She tensed up then her penis began to throb between my fingers. I continued stroking while she orgasmed. Her little penis continued jumping, but she didn't ejaculate, so I figured she couldn't produce sperm yet. I was so turned on, but it felt odd as I have never had any gay thoughts before. I guess I was turned on because I looked at her as a girl, even though she has a penis and testicles.

I end up getting a charlie horse, so I stood up and worked it out. When I looked at Riley, she was staring at the tent in my pants. I was so hard and turned on that I just removed my shirt, undid my pants and let them dropped to the floor. I removed each leg then slid my thumbs in the waistband of my boxers and slid them off. I stood straight up and my six inch cock also did and very hard.

"Do you want to touch it, sweetie?" I asked.

She nodded and I stepped between her legs. My cock was inches from her face when she took it in her hand. It jumped and she slowly began stroking it.

"You don't need to keep your dress on, hun." I said.

She let go and raised her hands as I leaned over and pulled her dress up over her head. I noticed she was hard again as she grabbed my cock and started stroking again. She was so sexy sitting there naked.

"Riley?" I said.

She looked up and said, "Yeah?"

"We are going to have sex, okay?" I said.

"Okay," she said.

"I gotta get something," I said.

I turned around, opened up the medicine cabinet and took out the vaseline. I opened it up and removed some with my fingers. I turned back to her.

"I need you to turn around and kneel on top of the toilet cover then bend over and stick your butt out." I said.

She did exactly as I said and my god, her ass was adorable and nicely shaped. Her anus was cute and dark red in color. I stepped up behind her and smeared vaseline over my head and shaft. I then rubbed the rest over her anus.

"If it hurts and or you wanna stop, just say so, okay?" I said.

"Okay," she said.

"Try to stay relaxed, hun."

I placed my index finger on her anus then slowly slid it in up to my big knuckle. She jumped a little, but didn't complain. I worked my finger in and out a few times. Her asshole was super tight. I then slid my middle finger all the way in with my index finger. She let a little moan as I slid my two fingers in and out.

"You okay?" I asked.

"Uh huh," she moaned.

I spread my fingers apart, trying whatever I could do to loosen her up before I stick my cock in her ass. After a few minutes, she began to push back against my fingers. Her asshole tightened around my fingers. I knew then she was close to an orgasm. I reached around and started stroking her little penis while I slid my fingers in and out of her tight virgin ass. She started bucking her hips and moaning. Then suddenly, she let out a long moan, her penis started throbbing and her asshole pulsated around my fingers. Her orgasm washed over her for a whole minute. Then her penis went limp in my hand and I removed my fingers from her ass. She laid her head and her arms down over the back of the toilet.

I positioned her feet between my legs as I stepped closer. I crouched a little to line my cock up with her anus, then placed my other hand on her shoulder and held her as I started pushing. The head slid in with easy, but then it got a bit tougher. I pushed harder and she grunted. I continued and the further my cock went in. I was about halfway when I slid out to the head and slid back in.

"Ugh...hurts a little." She grunted.

I slowed myself and gradually eased my way in her ass. It took several long minutes to bury my cock deep in her. When I slid my cock to the base, my god, it was amazing, her insides were unbelievably tight and hot. Also, I don't know if she was doing it on purpose or it was involuntary, but her anus kept opening and closing around my cock while the walls of her rectum milked it. I never felt something milking my cock like that before.

"You okay, hun?" I asked.

"Uh huh," she muttered.

I kept my cock deep in her till her insides fully adjusted to it. I ran my hands over her back and around to her flat chest. I lifted her chest and pulled her back against me. She held onto my arm as I slowly stood up causing my cock to go even deeper in her ass.

"Uhhhggg, Derek!" She grunted.

Her ass squeezed even tighter around my cock. I held her as I slid my other hand down her front. When I came to her penis, it was nice and hard. I slid it between my middle and ring finger as my hand went down. I then gently massaged her ball sack and taint.

"MMmm!" She moaned.

I tried sliding my cock out, but her ass gripped it too tight.

"Relax your ass, sweetie...try pushing a little, like when you poop." I said.

She nodded and moaned, "Okay."

She grunted a little and pushed. I was then able to slid out to the head and back in again.

"Mmm Riley, you're doing so good." I moaned.

She was moaning so erotically as I continued sliding in and out of her ass. When suddenly, a stream of pee sprayed up towards our faces. I quickly aimed her penis towards the wall and continued massaging her taint and ball sack while she orgasmed. Her penis jumped up and down between my fingers and every second, pee would spray across the wall. She sprayed at least ten times up over the wall.

I started thrusting my cock in and out. She held on tighter, bouncing up and down. I then began stroking her penis. She was non stop moaning and I couldn't take it any longer. My cock swelled up and I drove it deep in her. My orgasm hit me so hard, my cock started throbbing and I shot my cum deep in her. She then orgasmed again, her penis throbbed in my hand, and spraying a couple times. I continued cumming, squirt after squirt of seamen poured into her rectum.

As my orgasm subsided, I was able to think and realize that she may have to go potty when I pull out.

"Sweetie, when I slide my cock out, I want you to sit on the toilet with the cover up." I said.

"Okay," she said.

I slowly slid out and quickly lifted her down. I flipped the cover up and she sat down. A few seconds later, I heard my cum drip into the toilet then her poop followed, splashing down into water. I looked down and noticed there was some on my dick. I then turned the shower on.

"Hun, when you're done, come get washed up." I said.

She smiled and said, "Okay."

After I stepped into the shower, I washed my dick then leaned against the wall, drained from the best fuck of my life. Shortly after, I felt a hand on my side. I turned around and there stood Riley, I looked her up and down. She was beautiful, with her pale skin, flat chest, hard little nipples and little penis.

I began washing down her back and to her ass. She jumped a little as I wiped over her anus.

"I'm sorry, hun." I said.

"It's okay, Derek...just a little sore." She said.

"Lemme see," I said as I knelt behind her.

I gently spread her cheeks and was glad to see her anus had shrunk back to normal. I gently wiped down her crack and over her anus. Her anus squeezed tight as I wiped over it.

I kissed it and said, "All better!"

She turned and giggled, then gave me a kiss on the lips. We then got out of the shower and got dressed. I noticed she didn't flush. I was surprised and relieved that there was no blood in the water. I flushed the toilet as I took a piss. We then left the bathroom.

"Wanna go watch t.v. and wait for your mother?" I asked. "Okay," she said.

We sat down on the couch and I put my left arm around her as she snuggled up against me. She laid her head against my upper rib and her right arm over my lap. An hour went by when I felt her penis grow hard under my hand. I put my hand under her dress and she spread her legs. I then rubbed the head of her penis with my thumb.

I don't know what possessed me to do what I did next, but I did it. I knelt on the floor in front of her and slid off her panties. She held her dress up as stroked her penis. I then bent down and sucked her penis into my mouth.

"Mmm!" Riley moaned.

I swirled my tongue around her shaft and over the head. I then sucked up and down her penis. She started moving her hips and moaning. I went down to the base and stuck my tongue out and licked over her ball sack. I felt her penis jumped a few times, hitting the back roof of my mouth. I went back up to her shaft and sucked up and down. A couple minutes later, she thrust her hips up, her penis swelled up a little and then it started throbbing. She moaned loud and orgasmed. I continued sucking while she humped my mouth. Several seconds later, she started to relax. I removed my mouth from her limp penis and sat down next to her. She laid there catching her breath.

"Did you like that, sweetie?" I asked.

She smiled and said, "Yeah!"

I unzipped my fly and pulled my cock out. She got down and knelt between my legs. She took my cock in her hand, stroked it a few times then lowered her mouth down over the head.

"Mmm!" I moaned.

She slid her tongue all over the head then sucked it. Soon after, she slid her lips down the shaft and about halfway down, she gagged. She then stroked the shaft while she sucked up and down it. She was amazing, her mouth was nice and wet, lips and tongue were very smooth and soft and she gave the right amount of sucking. She gagged a few times at first, but then gradually learned how to take more in her mouth. By the time she worked three quarters of the way down my cock, I felt my orgasm coming.

"Just suck the head and keep stroking, sweetie" I said.

As she followed my directions, my cock swelled up and I then shot my cum into her mouth. I didn't think I would have came so much, but I did. Some leaked out the sides of her mouth and ran down her chin, but she kept stroking and sucking. My cock went limp and she removed her mouth. She lifted her head up with my cum still in her mouth.

"Sweetie, it's okay to swallow it." I said.

She squinted as she swallowed my cum.

I giggled and asked, "You okay?"

"Yeah,"she said.

"Did you like the taste?" I asked.

"Yeah, but the feel of it was...weird." She said.

"Oh okay...wait here, I'll get a cloth to wipe your mouth." I said.

I put my cock away, then went and got a cloth. I wiped her mouth and gave her a kiss. Suddenly the doorbell rang.

I shot up and said, "Put your panties on."

I went to the door and opened it.

"Hi Derek," Cindy said.

"Hey Cindy, please come in." I said.

She stepped in and asked, "How was Riley?...hope she wasn't any trouble?"

"Oh god no, she's an angel and was a lot of help too." I said.

Riley walked in the hallway, hugged and greeted her mother, "Hiya mom!"

"Hi sweetie, heard you had fun." Cindy said.

Riley smiled and said, "Yep, I planted flowers and painted a little."

"That's good, darling! Well thank you for watching her, Derek." Cindy said.

"Oh no problem, anytime you need me to, I will." I said.

"Okay, great...well time to go Riley." Cindy said.

Riley turned then gave me a hug and said, "Bye, Derek"

I hugged her back and said, "Bye, sweetie."

They stepped out and went down the steps. She turned her head back to me and smiled. When she got out of sight, I closed the door and leaned against it.

"Yep, I'm keeping the house and living here! First thing I'm going to need is a bed." I said.

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Tina

Nice and lovely story!

dusty825

loved the story

Nipplelover

Wonderful story! Would really like another chapter so the mom can get involved.

cuchilo

That was an interesting story, and it got me really hard. Quite a twist.

Ron

Even though the story was very hot, wish it would have been a little girl. Maybe next time...

o

Wow, did that ever take me back! When I was a little boy I loved to wear girls clothes and ,luckily, had a couple of friends who let me wear theirs. Their mothers seemed to find it amusing to see me in panties and dresses and (I'm glad to say) never mentioned it to my mum who was very straight-laced. I could happily have been Riley, thanks for the memory.

Lolibill

A very nice story, I think you have the right characters to write at the least another story or two and I hope you do.

Derek

Nostalgic overload!

Amoureuse

Really nice and erotic. Love stories about little boys brought up to be girls.

Licker

Loved the story, very erotic. I do hope you will write more about Riley. I was surprised that Derek didn't warn Riley about not telling anyone about what they did to each other. It would be very interesting indeed to learn how mommy would react if she found out.

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