Florida Vacation

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Trip to childhood resort turns her into a woman.
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I called him "Uncle Matt," but he wasn't really my uncle. He was more my father's best friend, childhood friend actually. Our families were really close. He had a daughter, Carmel. She was a year older than me and we were friends, though not best friends like my daddy and Uncle Matt. She was a little too snobby sometimes, all because her father owned "six dealerships in four different counties," blah blah blah. But when she wasn't being snobbish, we were cool.

One weekend we all went to Florida to have a small vacation at their "summer" house. They really didn't go there often and I really don't remember them ever spending a summer there other than that first one when they brought the house and they went to Disneyland. We didn't go because daddy wanted us to visit grandma and grandpa in upstate New York. We all arrived there Thursday night. Mom, dad, Aunt Elaine and Carmel all went out looking for maps and stuff so they can preplan our trip. They wanted to feel they got their money's worth.

"Disneyland is so big, it would take more than a weekend to see everything," Aunt Elaine said.

I didn't go because I didn't even want to be there. Disneyland is for babies, I told them. I'm a young woman. I am no longer a child, I turned 18 years old last week. Carmel looked at me and stuck out her tongue. I knew she loved Disneyland and that just made her one big baby in my eyes. Uncle Matt stayed behind with me. He told everyone I shouldn't be here by myself (I guess he thinks I'm still a baby, too), but he leaned in my ear and said it was because he didn't really like Disneyland too and we should let the children go have their fun. I laughed at him. We smiled because we now had this secret and this common bond—our hate for Disney.

It was hot in the house. The air conditioner was apparently broken and it was too late to call a repair guy so Uncle Matt said he will call one in the morning, but we'll just have to suffer through the night. Uncle Matt saw my discomfort and suggested that I take a swim in the pool out back to keep cool. Ok, I said and went to get the bathing suit Carmel gave me. It was an old bathing suit of hers, a bikini. I was smaller in frame than Carmel and she outgrew it a long time ago, so she thought it would fit me. I didn't own a suit. Even though I knew how to swim, I didn't do much swimming at home. We didn't have pools and stuff.

I put it on, but apparently I wasn't as small as everyone thought. The top just managed to cover my nipples. The strings were not very long and it was tight as I tied it around my back. It pushed my breasts inward, making them squeeze out to the side. But there was nothing I could do about that; it was too hot in the house. The bottom fit though, so that was good. I left the room I shared with Carmel and ran to the back of the house. Uncle Matt was nowhere to be seen. He was probably in the room he shared with Aunt Elaine. The water was heaven. It cooled me off instantly. I had to have swum for 20 minutes or more. Uncle Matt came out to the pool, probably to make sure I didn't drown. He watched me in the water. Finally he said it was getting late and I should come out. So I swam to the steps and climbed out.

Uncle Matt stared at me. I smiled and told him that was great. He said he was glad, and then he told me to come closer. Confused, I stepped over to his chair. He reached out and wrapped his hands around my waist. He was looking at me, at my body. I felt a weird sensation in my chest, like when I'm cold. But I wasn't cold. I was just right. I followed his glaze. The water wasn't good for my suit. It seemed to have shrunk. My nipples harden and more of my soft mounts became visible. The fabric of my bottoms sunk into the hole of my puss. You can see the line were my two lips met. It was embarrassing. I tried to cover up. I folded my arms over my chest and bent forward to hide myself, but he stopped me.

No, he said. I was beautiful and I shouldn't hide. He also said I was right, that I'm a young woman now, with a young woman's body and that I shouldn't be ashamed. He separated my arms and gently held them out to my sides so he could look at me again. I don't know why I let him. I knew it wasn't right. Uncle Matt shouldn't be looking at me, even if he wasn't really my uncle. He shouldn't be looking. But I let him look, I didn't really want to admit it, but I liked him looking at me.

It became harder to breathe. He saw that. He asked if I were tired and if I needed to sit down. My legs were weak so I said yes. He said I could sit with him on his chair, but there wasn't any room on the chair so he suggested I sit in his lap. I eased onto his lap. I didn't quite know where to go so he helped me. He turned me so my back was to his chest; he told me if I opened my legs and straddled his I would be more comfortable. He was right. There was something poking me in my hip. I told him so; I suggested it may be his keys and that it hurt so could he please move it. He lifted me up by my hips and readjusted me. I felt the weirdest sensations as he touched me, sort of like I get when I see Orlando Bloom, that actor from Lord of the Rings, who played the elf. He was so cute. Only these feelings were more intense. I never felt anything so strong. When he stopped moving me, the hardness moved to the crack of my ass and was sandwiched by my ass cheeks. That was better, but I was still confused, why didn't he just remove it from his pocket. I wasn't sure what it was, but it didn't feel like keys anymore. It was kind of rounded and ...

Ooooooh myyyyyy godddddddd!

I knew what it was! I knew what it was! It was his privates! It was his dick! It was his... cock (giggle). I knew because I heard the girls talking at school. They said it became hard when a boy got "turned on" by you, and when he wanted to put it inside of you, when he wanted to fuck you. I couldn't believe it. Uncle Matt wanted to fuck me. ME! I really was a woman if I could turn a man's head like Uncle Matt. We sat there for a minute, him and me. My back to his front. The more time went by the more I became relaxed and sort of sunk into his body, his heat. Then his hands moved.

They moved from my hips to my tummy. My hands were resting on the chair arms and I gripped them in surprise. There was that feeling again. It moved with his hands, along my tummy. I couldn't breathe. I had to force myself to take a breath. I was scared and I was excited too. I never felt like this. His hands stroked my skin, softly, inch by inch. Each movement became more and more unbearable. I didn't know if I could take it. My tummy.

"Uncle Matt," I cried out. "Please stop doing that."

He stopped. He asked if he was hurting me.

"No."

He asked what was wrong. I told him the feelings were too much. I didn't know if I could handle them. He asked if the feelings were bad.

"No," I said again. "They are different, but not bad."

His hands moved upward, they moved the fabric from my breasts. I looked down and saw my nipples poke out into the night air.

"Oh god, " I moaned.

His fingers touched my tips and my pussy tightened, it clenched, squeezed tightly inside its self. I couldn't control it. His hands, cupped my breasts-- my mounts and he squeezed them softly. I moaned some more. It felt... it felt...

His fingers found my nipples and then squeezed them. Oh god, the feeling-- it shot from my breasts, down my tummy, then to my puss, between my legs. I felt warm sticky moisture leak out of me. It was warm, yet cool to my heated thighs. I think some of it spilled onto his thighs. He was breathing harder now too. His dick, that hard part, was pressing up against my butt, in the crack. He was moving his hips under me, sliding his cock against me, rubbing me with it. He pulled my nipples. I screamed. It was too much.

He squeezed harder, harder, harder and he twisted them, left then right, then pulled them up, then down, and then around and around, and I was crying. It hurt so badly. It felt so good. I couldn't hold on anymore. I moved my hips with him. I moved against his cock, but it wasn't my ass that ached, it was my puss. My puss hurt so badly.

I didn't know I said the words out loud until he told me he would help. His hand left one of my breasts.

"No!" I cried. "Please."

But he put his hands there, in the heat of me, in the center of my pain. My body jerked from feelings so intense. He found that hard button between my lower lips, he stroked it, he touched it and my body-- my body lost control. My body wasn't mine. I couldn't think. He stopped. He stopped stroking me. The feelings were still there, but the building of pleasure stopped. I cried out again, begging him to continue. He lifted my hips off of him and moved me upward on his body. I didn't know what he was doing. I looked down just as he lowered me back down. I saw this round brown tip with a hole in the middle peak through my thighs. It was his dick. It had to be. It looked just like the pictures. He moved my hips, sliding my pussy along his shaft. It felt good, as good as his fingers and it was then that I figured it out.

I pumped my hips with him, sliding, rubbing my pussy along his dick. The more I slid the more wet he became and each slide became easier. He was leaking moisture too, from his tip. It was sliding out of his hole, down his cock; some of it fell onto my clit. I saw it. I felt it. It was so sexy. It was so nasty. I was riding Uncle Matt's cock. I closed my legs so I could trap him better between them. I felt him even more. It added more pressure to that point where I needed it and I moved. I moved. I bounced on him. He let me. He released my hips and let me move on my own. It was building. I felt it. It was building. I couldn't breathe. All I could do was feel my pussy as it started to contract.

'Oh god,' I chanted, over and over, and then he griped his cock, from under me, he gripped it at its based and held it steady. I wanted to cry. He was interfering with my rhythm. He lifted me up again and moved his tip to my hole, my opening, and he pushed. It felt so good. Oh god. And I pushed back and then it started to burn, there was heat everywhere. It burned and burned until it started to hurt, then my pussy started to squeeze again and I lost it. It was squeezing, squeezing so hard at that tip, at that head of his cock. My world turned completely upside down. I was cumming, and I squeezed the cock tip right out of me.

I was so tired. After a minute, I tried to breath and I felt tears roll down my eyes. I lifted my head from his shoulder and looked back down. His cock was still between my legs, still here, still hard. Tentatively, I touched it. The hole was still leaking. He moved then, he rose from the chair and took me with him. We were both standing, but I couldn't support myself so I leaned on him. He turned me. He told to lie down onto the floor and spread my legs. I did. He removed his shorts. That was all he was wearing on this hot night. He went to his knees; he leaned over me and completely removed my top and untied my bottoms. We were both naked. We looked so different he and I. He was flat where I had curves. It was weird seeing his hips, so unlike mine, so straight. His chest was hard with muscle, he worked out. I was too lazy to workout. He had hair all over his body. I was smooth. He had a lot of hair down there, around his hard pole. I didn't have much. I've had hair down there for over 2 years now, but it wasn't much. It looked like peach fuzz, almost, but it was there. You could see my lips more clearly then I could see his balls.

He leaned over me and he kissed me. Uncle Matt kissed me like a man kisses a woman. His tongue was so strong and sure, like his touch. I felt like I belonged to him, like I was put there just so he could touch me, squeeze me, lick me, and eat me up.

I was his.

He kissed his way down my body; he sucked on my breasts. Oh god, I loved that. The harder he sucked the more I loved it. I couldn't keep still, my god, he was so good.

"Harder! Harder!" I cried.

And harder and harder he sucked, holding my breast steady as he tried to put all of me in his mouth. Then he changed his method. He started to use his teeth. The moment I felt that intense pain/pleasure I nearly came again. His fingers found my pussy as he sucked me. I was in heaven with his mouth on my titties and his fingers on my clit. He rubbed me, and then he moved lower to my pussy. It stung slightly from the stretching before. He dipped his finger in me and stroked. He stroked and stroked, while he sucked. One finger became two and he rubbed and he rubbed. Two figures became three, and the burn came back. The burn. It hurt yet it made me wetter. The burn felt good and bad all at once. Then he bit my nipple, so gently, and my pussy tightened, undoing all his work. So he had to start again.

One finger. Two. Three fingers. Four. He stroked me. He fucked me with his hands. I fucked his fingers as he sucked. One breast then the other, one nipple then the other. I felt like I was breastfeeding him. I imagined milk flowing from my body as he sucked, sucked all my juices. He removed his fingers. I could hear the suction from my body as it let him go. He stopped sucking me. He moved upward. I opened my eyes and watched as he held his cock and moved it to my pussy opening. He moved it and pushed. The burning started again.

The burning. He pushed. It hurt. I cried out. He stopped. His fingers found my clit and he rubbed it in circles, around and around. It was as if he was somehow opening my puss by circling my button. He slid in some more. I wish I could say it was an inch, but it was more like a centimeter. He was trying to get his head all the way in, past the little nub that was at the opening of my puss. But I was tight, so all it did was burn more as he tried to open me up.

"Relax," he told me. "You have to relax."

But I couldn't relax; it hurt-- the burn, but the stroking of my clit helped and with each pass he slid in a little more. Finally he told me to do it. So my hands reached down my body and I expertly rotated my button the way I knew how. His hands reached for my breasts so he could play with my nipples. Oh yes.

He watched me rub myself. He watched as my movements opened my pussy around his cock and he watched as his cock head slid completely in. It was then that he moved out of me and then pushed back in. It was easier this time, but he still only went in so far. So I continued to stroke and rub, like he did, and he continued to push and pull from my body. He continued to twist my nipples, keeping my pussy juices flowing. In and out, he moved slowly, moving against the burn. I was really starting to like the burn now, as long as he continued to move slowly.

Deeper and deeper he moved in me until, suddenly, I screamed in pain.

Oh my god it hurt so much!

He stopped, shocked. Then he took my hands from my pussy. He held then down beside my head. I started to cry. The pain was easing, but I still felt it.

"Uncle Matt?" I cried, unsure. "I think I want to stop."

He moved over me, and the burn intensified. He moved back, out of me, moving further than he did before. He was leaving me. I began to relax. He leaned over and kissed me again. He told me I was sweet. He told me I tasted like candy and felt like paradise and he kissed me. I sighed as the burn and the pain decreased.

Then sudden his whole body slammed against mine. Hard, deep, deep was the thrust of his cock, up into my body, tearing me apart. I felt a rip inside me and I cried. I cried. He stopped. He was in completely now and finally he stop moving. He kissed me. He kissed my tears; he kissed my cheeks; he kissed my lips. I turned my head away. I didn't kiss him. I wanted him to stop. I didn't like this anymore.

"Please, Uncle Matt, please stop. Please get out of me. It hurts." But he didn't move. He said nothing. He just continued to kiss me. My thighs began to ache. They weren't used to being spread this wide this long, but slowly, after I don't know how many minutes, I relaxed. It felt like he was in me for hours, but he was still hard and you can't stay hard for hours, can you. He kissed me. Softly. Signing, I looked at him with soft, sad, brown eyes. He licked my face. He cupped my breasts again and took another nipple into his month. He sucked me again, he drank from my tittles, twisting them with his tongue, using his teeth like I liked. I started to get hot again. I started to feel that internal fever that couldn't be washed away with water. The flow started again, past my pussy lips; my hips moved on their own. They moved around him. My clit was so sensitive the wiry feel of his public hair against it was almost too much. He moved out of me. It hurt, it burned, but it was different. I kind of liked it now. He sucked my nipples and increased his pace. He started to fuck me. He started to fuck me and he started to talk.

"Yeah. That's it. Open up for me, baby. Open that sweet pussy. I'm going to fuck that pussy. I'm going to fuck your pussy, Brie. Do you feel, me?

I'm going to open you up and fill you with cum from my cock. But first let me feel you cum on my cock. Open for me, baby. Give that sweet cunt. You're a woman now. Fuck me like a woman can."

No one ever talked to me like that before. I loved it. The pleasure was back. I couldn't breath again. It was like a mind-over-matter thing. I told myself the burn felt good and then it did, it felt good.

"Uncle Matt, fuck me," I said. "Suck on my titties. Drink me. Drink my milk. Fuck me and fill me with your milk. Make me wet with your crème, with your milk, fuck me."

He lifted my legs and put them on his shoulders. His thrust was harder and deeper.

"Oh yeah. Oh yeah, " I whispered.

He was fucking me. Fucking me outside by the pool, on the ground. His cock was deep inside my body. My little hole was spread open for him, yet still tight and wet, all for him. He fucked my lil pussy hole. He fucked me... he fucked... he fucked me.

"Fuck me. Fuck me. Fuck me," I screamed

The feeling was much more intense. When my pussy started to squeeze, started to contract, it did so against him and with the fit being so tight and his dick being so hard, the pleasure was more than I imagined, and I came. I came all over his dick. His dick. I fucked his dick and for the second time that night my heart stopped and I died.

I couldn't do it anymore. My body slowly relaxed around him. I became numb. I couldn't feel anything. I felt nothing but him, still moving over me, in me. He was so wet. His sweat was dipping onto my body, onto my face. His hot breath was harsh on my lips as he moved in me, still fucking my hole. He was barely withdrawing now. He was just pushing, pushing, pushing in, as if he was trying to crawl inside me by means of his cock.

One jerk, two jerk, three! His breath exploded from his lungs. His shout of release could be heard passed the pool walls. A smaller shout interrupted next, right before he fell on me, breathing hard. His dick was still inside. He just lay there, he lay on top of me, nearly crushing me with his weight, but I didn't mind. I just rested there and let him. He dick began to soften and slide out of my pussy. I felt more of my pussy now. It was on fire and this time the burn wasn't good. He rolled off of me, falling to the ground beside me like dead weight. He tried to control his breathing. He coughed.

"Whew" he said, resting his arm over his eyes.

I sat up. My body was so stiff, I could barely move. The hard floor didn't cradle my soft curves. I felt like I took a beating. I looked down between my thighs. The spot where his pelvic bone beat into my hip was sore. I would have a bruise in the morning. Then something caught my eye. There was blood on my thighs, not much but it was there. I turned to him.

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