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TomBoy's Awakening Ch. 1

By: Wilrun



As long as I can remember Missy has always been one of the boys in our family. I have two boys Justin and Jacob. Missy was a neighbor girl who grew up with my oldest boy and went everywhere with the boys. She went fishing, hunting and played football, baseball and basketball equally as well as the rest of the boys. She wouldn't even think of herself as a girl and always wore jeans and loose shirts. 

It was this one particular weekend as the group had been getting older and ready to go back to school, that we took off for a weekend at our cabin in the mountains. We had arrived and opened the cabin and put away the food. I have a loft bedroom and the boys and their friends have a bedroom with four bunk beds, so they can have friends along.

Justin had gone outside and Jacob and Missy were still inside horsing around. Jacob has always been in the middle of any activity and was trying to bug me while I was reading a magazine. So I grabbed him and wrestled him to the floor and was tickling him, when from behind, Missy couldn't resist the opportunity. She dove into the back of me and pinned my arms down long enough for Jacob to escape. Out the door Jacob ran and his older brother called to him to go fishing. Missy was on my back laughing and doing everything she could to hold me down. I leaned forward and rolled her off onto her back with both of us now laughing and wrestling each other. Then it happened, I reached down to pin her leg and she moved and trapped my hand between her thighs and locked it next to her little cunt. I think we both realized what happened about the same time. I went to move my hand and could feel those nice little pussy lips against my fingers.

Missy wouldn't release my hand but just kind of smiled at my predicament. Suddenly after all these years my thoughts changed from just another boy to this young woman coming of age. My thoughts went from wrestling with a boy to lust for a young virgin pussy, at least I thought Missy might still be a virgin. After all she always looked like a boy, hair short, dressed like a boy and acted tough like a boy.

I decided to see how far this might go, so I just started rubbing against that tight little pussy. It didn't take long and I could see Missy was relaxing her grip on my hand and starting to breathe a little heavier. By now my cock was starting to get hard and my hands were shaking. I leaned over and asked Missy in a low voice, as if anyone could hear anyway, if what I was doing felt good. She smiled and said it did. Then I asked if she wanted me to do some more and she nodded her approval.

I moved my hand up and down her thighs and back over her pussy feeling through the soft material of her sweat pants. I then reached up and untied the drawstrings to her sweat pants so I could get a better look at what was hiding underneath. By now her bulky sweatshirt had pushed itself up under her soft white cotton bra. I could see the underside of her two small firm breasts pushing against her bra. I reached up and ran my hand over her right breast and felt the hard nipple through the soft material of her bra. My breathing was getting heavier by the minute. 

Those small breasts felt so firm under my massaging fingers and Missy was getting hotter by the minute also. I moved back down over her flat stomach to the top of her sweatpants. I pushed the sweatpants down to reveal her panties. They were girls Jockey panties with little yellow and purple flowers printed on the cotton fabric. Missy lifted her back up a little so I could push her panties further down her legs. I was now gazing at a perfect little cunt that had some of her auburn hair covering a small part of her "V". The lips to her cunt were swelled from my stimulation and pouted out wanting for more. I left her pussy exposed and moved my hand back to her soft white bra and moved the strap aside and lifted one of her tits out for my viewing. The nipple was like perfect Hershey kisses with quarter size dark rims flaring up to those hard little points. I bent down with my mouth and took the nipple in my mouth and gently started sucking on it. With my free hand I reached over and started once again to massage those little cunt lips.

Missy was now starting to push against my finger and let out a soft low moan of appreciation for what I was doing to her. As my finger pushed further into her secret place I could feel the sweet nectar oozing out over my fingers making them wet. Both of us were now thoroughly enjoying what was happening. I took my finger out and tasted that sweetness that was clinging to the end. I could smell the slight musky odor from her secretions and it just about drove me over the edge.

Then it happened I could hear the boys coming back from fishing! Missy and I quickly rearranged her clothing and tried to act normal as the boys came through the door.

Stay tuned for the further awakening of Missy.

TomBoy's Awakening Ch. 2



The rest of the afternoon, Missy followed me around like a puppy dog, wanting to get close or next to me wherever I went. Not that I minded as my cock was now definitely ruling my mind. 

We had finished supper and the night air was cooling down and a full moon would make it light outside almost all night. The boys had all taken showers and were getting ready for bed as Missy took her shower. When she came out of the shower, I noticed her in a different light for the first time. She was wearing a short cotton nightie that just barely covered her little panties. Her dark nipples pushed out against the soft fabric and she noticed me watching her and smiled to herself. 

Jacob always wants me to read a book to him as he goes to sleep and tonight was no exception. Justin had jumped up into the top bunk and was almost instantly asleep. Missy had crawled into the bunk opposite Jacob and was quietly lying there as I read the book. It wasn't long and I could tell that Jacob was also asleep. I got up to leave and a hand reached out and rubbed my leg, it was Missy. I reached over turned the light off and leaned down close to her to see what she wanted. She didn't have to say a word; she just lifted the bed sheet and beckoned me to crawl in with her. My heart started pounding again as I anticipated what I was about to do.

I crawled in beside her and could feel the warm soft flesh lying next to me. I just lay there waiting to see what would happen next. Missy reached over, took my hand and lifted the top edge of her panties, placing my hand down between her legs. Then for the first time she took her hand reached across and placed it directly on my cock, which was now at full attention to what was happening. She was new at this and didn't quite know what to do, so I helped her feel my cock and than she felt my soft balls with her fingers, gently massaging them. I knew that things were going to progress further and didn't want it to happen there in the bunkroom. So I gently kissed Missy on the lips and told her I was going upstairs to bed and she could follow if she wanted.

I left her bed and went upstairs to mine, trying to rationalize what might happen next. She was definitely of age so there wasn't any legal problems with what I was doing; it was that I had always thought of Missy as a boy and not a girl. Boy was I wrong on that one. Anyway as I lay there she must of known what she wanted, because I could hear the stairs creak as she made her way up to my bed. I lifted the sheets for her and she crawled in next to me snuggling up close. The moon was bright and lit up the room so you didn't need any lights to see clearly. I looked into her face and asked her if this was what she wanted? She nodded, smiled and said make me feel good again. 

I leaned over kissed her on the neck and then kissed her on the mouth and let my tongue explore her sweet young mouth. With my hand, I slid down between her thighs and found her panties waiting for me. The surface of her cotton panties was already getting wet in anticipation of things to come. As we kissed I could feel her hand starting to explore on her own, seeking out my cock and rubbing it through my pajamas.

I kissed my way down and over each of her breasts moving the short nightie up and over her head, leaving only those little panties covering the last part of this girl. As I kissed and sucked on her breasts, my hand were kneading and massaging those outer lips of her cunt. I could feel the blood engorging its way into the lips making them pout and swell. I reached up and started to slide her panties off and she lifted her hips so I could slide them down and off her ankles. Now she lay there completely naked to my view and exploration. I inserted one of my fingers in between her pussy lips and gently explored up and down finding her little clitoris. When I brushed against it, it sent a shock wave through her and she jerked in response. I then moved my finger in and out, finger fucking her.

She started to moan and respond with her hips starting to move in rhythm. I didn't want her first climax to come by my finger, so I pulled out and quickly replaced it with my tongue. The nectar that was oozing out tasted oh so sweet. My tongue moved in and out like a small cock and I could feel how tight her cunt muscles were. As my tongue picked up the pace so did her hips and moaning. She said oh oh do it some more, don't stop. With that she grabbed my head and pulled me closer into her pussy. Her cunt muscles tried to grip my tongue as it would a cock in the same place. Missy finally went over the edge and washed cum all over my face. I gently feasted on her now wet cunt as she slowly started to subside from her first real orgasm. After she slowed down, I could feel her reach over and start to massage my cock again, which by now was thinking it had been completely neglected.

My cock was now standing straight up pushing my pajamas out like a tent. I lifted my hips and Missy tugged my pajamas down exposing my cock to her view. I just lay there as she explored my cock and played with my balls. She got down real close to my cock and quickly took her tongue and tasted the head of my cock. Having decided it wasn't to bad she went back to my cock and her tongue started to lick all over the head. Precum started to ooze out of the head and I could tell she liked the taste. Then she started to suck over the whole cock trying to get as much as she could into her mouth. I didn't want to come in her mouth but would rather shoot my load into that tight little cunt of hers. I wasn't afraid of getting her pregnant as I have had a Vasectomy after Jacob was born.

So I pulled out of her mouth and she looked a little astonished. She wanted to know if something was wrong and I smiled and said no, she was very good. Then I asked her if she would like both of us to come together for her first time. She smiled nodded her head in approval, but looked a little worried. I told her it was going to hurt the first time, but I would be as gentle as I could. She then lay back down; smiled once more and spread her legs wide apart and reached out to pull me down on top of her. I slowly moved my cock up and down over the entrance to her perfect little cunt, making sure the head of my cock was well lubricated before I pushed further into her. The head of my cock slowly worked itself into this very tight pussy and I slowly moved in and out so she would get used to having a cock in there.

As I pushed further in I finally found the protection of her hymen, blocking the way to further penetration. At this point I could sense the tension and pain that was developing. I moved my mouth over Missy's mouth and gently kissed her as I pushed forward breaking through the final passage. With a stifled scream from Missy I pushed my cock all the way in, with my balls tight against her ass. I just lay there waiting for Missy to get used to the feel of a full cock resting in her most precious treasure house. As the pain subsided I could feel Missy's muscles contracting around my cock. I started to move in and out slowly. Her cunt was very tight around my cock and stuck like glue as I tried to move in and out.

As our momentum started to build, I could tell she was approaching another orgasm. We both started moving in unison with pleasure building between us. As my cock started moving faster and faster, I felt my balls tightening, as my load of cum was about to shoot deep into this precious cunt. As I went over the edge Missy wrapped her legs around my waist and shot forward as another massive orgasm shot through her body. My cock shot a huge load of cum into her and I could feel her cunt squeeze every drop from my balls. As Missy slowed down and my cock shrank once more, it finally slipped out of her cunt and we both relaxed. 

The next thing I knew, I could see the sun rising over the mountain and there was a warm cuddly Missy, that was no longer a Tom Boy, laying sound asleep next to me. I gently woke her up and helped her put back on her panties and nightie. With that I sent her back down to her own bed, before the boys woke up. As Missy goes off to college I will wonder if she will remember the time when she was awakened from being a Tom Boy.