The Babysitter's Secret

byWannabe Chick©

"Oh darn," she said with a very sardonic tone. I looked at her and raised an eyebrow. "You and me. All night. The kids are asleep. Your wife is gone. I'm hornier than I've ever been in my life. I think this is an answer to my prayers."

"We don't have to do anything else if you . . ." I began.

"Yes, we do!" she exclaimed, laughing. "I'll call my Dad."

Jenny skipped away to the kitchen to call her house. A few moments later, she asked me to come in, and handed me the telephone. I was nervous speaking to her father, fearing that Mike somehow psychically knew what I had just done with his daughter, but he was very understanding of the situation. He agreed that it was complete reckless to drive and was very grateful of my offer to let Jenny sleep "on the pull-out couch."

When I was done, I handed the phone back to Jenny. She said goodnight to her father, then to her mother, and then hung the phone up on the receiver. As soon as it was down, she squealed with excitement, and threw her arms around my neck. We kissed again, but more passionately and intensely than before. Already, my cock was hard again.

"We just have to keep it down," I said. "We can't wake the twins."

"Those two can sleep through a fire alarm," Jenny pointed out as she kissed my face and neck.

"Good point," I remarked, "now let's go upstairs."

I scooped Jenny up and held her in my arms. She laughed and kicked her feet excitedly as I carried her out of the kitchen. Up the stairs I carried her into the room that I had shared for years with my wife and was now about to share with a transsexual teenager. I have to admit that there was some guilt about my infidelity, but I could not stop now, even if I wanted to.

I placed Jenny on the bed, then climbed on top of her. I spread hungry kisses all over her face, then on her neck, and of course on her delectable lips. Jenny wrapped her arms around my neck and her legs around my waist, clinging tightly to me. My right hand founds its way to her breast and began to massage the tender flesh through her sweater. To my surprise, Jenny pushed my hand away and drew her face from mine.

"What's the matter?" I said, suddenly frightened and disappointed.

"Go into the bathroom for a minute," she told me as she slid out from under me.

"Why?" I asked.

"Trust me," she said with a smile that let me know our fun was far from over. "Go."

Doing as I was told, I climbed off the bed and walked into the master bathroom which was attached to the master bedroom. I shut the door and waited patiently for Jenny to do whatever it was she wanted to do. I heard movement from inside the room but resisted the urge to put my ear to the door. I knew Jenny wanted to surprise me.

A minute or two later, Jenny beckoned me back into the room. I opened the door and stepped into the bedroom to see my eighteen year old babysitter lying on her side, elbow cocked, head resting in her hand as she faced me. She was dressed in a black babydoll with black fur trim and a matching pair of g-string panties. The material was transparent so that I could see her nipples through the top and, through the panties, her small cock as it strained against the fabric.

"Holy God . . ." I breathed.

"I always wanted to wear something like this for you," she told me.

"But where did you get it?" I asked.

"It's your wife's," she explained. "I saw it when I came up here one time to borrow a sweater. I think she must have been saving it for a special occasion."

"Well, this is a very special occasion."

"It sure is. Now don't keep me waiting."

I jumped on top of her and at once we were passionately kissing. She put her arms around my neck, pulling my face closer to hers, kissing me with a ferocity brought on by teenage lust. I was actually a little surprised since, back when I was younger, girls her age weren't nearly so into sex. Maybe it was the change in the social climate but more likely it was simply that Jenny might be a teenage girl, but she had the sex drive of a teenage boy and that's a force that's nearly impossible to resist.

I kissed Jenny's freckled face, then worked my way down to her neck and throat. I planted hot kisses all over the tender flesh before proceeding down to her collarbone. I kissed the bare skin of her shoulders, breathing in the clean, pure scent of her skin. Before long, my hands were on her breasts, and my mouth was on her nipple. It was poking through the flimsy material of her lingerie and I licked and sucked the fabric eagerly.

Jenny wasn't satisfied with this so she unhooked the straps of the babydoll and pulled the garment down to expose her perky, teenage tits. I wanted no time and practically devoured the supple flesh. Her pale pink nipples were hard as tiny pebbles between my lips. All the while I nursed and teased Jenny's breasts, her hand was buried down between her legs as she rubbed the palm of her hand up and down the shaft of her little, girly cock.

Unless you've ever touched or sucked the breasts of a eighteen year old girl, you can only imagine how tender and soft they feel. True, Jenny wasn't like other teenagers, but in this attribute she was all girl. I kissed and licked every inch of Jenny's tits while she sighed and cooed her enjoyment of the experience. I remembered her fondling her breasts while she jerked herself off so I made sure to keep at least one hand on a breast at all times. Every time I pinched a nipple, Jenny's frame shivered and she sucked in breath.

"You really love having your nipples teased, don't you?" I asked.

"Mmm, yes," she replied.

"Maybe I could do a little more. Just let me know if it hurts."

I placed my lips over Jenny's left breast and kissed her pale, pink nipple lovingly. Then I parted my teeth and placed them gently around the tip, adding no pressure just yet. Jenny put a hand on the back of my head and caressed my hair. I closed my teeth just a millimeter and Jenny's body shook with delight and she dug her nails into my scalp.

I bit down again -- harder this time -- and Jenny's back arched, bringing her chest closer to my face. She yelped in a mix of pain and pleasure. I pressed my teeth into her nipple with a little more pressure and she was soon panting wildly.

"Does it hurt?" I asked.

"Yes," she said. "Do it harder."

Who was I to refuse? I clamped my teeth firmly around Jenny's nipple and she quickly covered her mouth with her hand to stifle a small scream. I didn't relent and Jenny didn't mind. I bit and chewed her nipple for a bit longer until Jenny's reactions seemed to be diminishing, then I moved on to the other one. The entire process began anew and Jenny loved every second of it.

After I'd tormented her nipples for a good while, I decided it was time to move on from her breasts. I was nervous, I'll admit, but Jenny had done it for me. Besides, I had come this far. It's not as if I had anything left to prove.

I kissed my way from Jenny's tit to her sternum, then down her flat tummy to her belly button. Soon only a thin layer of fabric lay between my mouth and Jenny's penis. It was clearly visible through the flimsy material and I took a moment to admire it. There was nothing intimidating about it. Even questions I felt about my own sexuality were immediately erased when I looked at the girl this dick belonged to. She was as feminine a girl as I'd ever met.

"You don't have to do anything to it if you don't want," Jenny said.

"You sound disappointed," I replied.

"I just mean that I understand if it's too gross for you."

"It's not gross at all. I think it's beautiful. Just like you. But this is so new tome."

"You don't have to."

"It's OK, honey. I want to."

I wasn't surprised at all to discover that I truly meant it. I was going to suck this girl's cock and I wanted to do it. I kissed the tip through the material of the g-string and Jenny trembled and moaned. Her cock immediately stiffened, pulling on the material. I kissed down from the tip to the bottom of her shaft and it got harder each time my lips brushed it. When I reached her nutsack, I noticed that little flaps of skin were sticking out on either side of the g-string in a way that was somehow cute and endearing.

At last, I was ready for the real thing. I hooked my finger under the g-string and pulled the material aside. Jenny's balls flopped free and her dick sprung to full attention. She held her breath, perhaps waiting to see if I would really go through with it.

She didn't have to wait long. Without a second thought, I wrapped my lips around the head of her cock and held it in my mouth. It was warm and meaty. I touched it with my tongue and tasted salty precum. My tongue explored the underside of her cock head and found it smooth and delicious.

I opened my mouth wider and took another inch into my mouth. I could feel the blood pulsing through her small prick and imagined that her heart must be pounding as hard as mine. I looked up at Jenny and saw her watching me with the tip of her pinky finger in the corner of her mouth. Her breasts were rising and falling as she breathed heavily. I reached out and took her hand in mine.

With that, I began giving the girl her first blowjob. At first, I just tried to do it fast, like I saw women doing to guys in porno movies. After a minute, though, I realized this was stupid. Like Jenny had said earlier, I had one myself so I knew what felt best. I liked it slow and deep and I hoped Jenny would to.

I took all of Jenny's cock in my mouth. It wasn't very big, so it wasn't difficult to lower my face until my chin was against her balls and my nose in her auburn pubic hair. I closed my lips tightly around her shaft and began slowly bobbing up and down.

Jenny's response was immediate. Her body began to writhe and twist beneath me, as if she were trying to find a more comfortable position, but couldn't. Her fingers tightened desperately around mine and I squeezed back hard to reassure her. I could only imagine the rush of emotions that was hitting her, not to mention the hormone overload. I remembered my first blowjob as a eighteen year old and thought she must be feeling a lot of the things I felt -- although the circumstances were quite different.

With my free hand, I cupped the side of Jenny's thigh, and rubbed it up and down. With Jenny's free hand, she toyed with her breasts. We soon fell into an easy and natural rhythm. Jenny moaned and sighed and gasped the entire time, although she was always careful to keep the volume low.

I wasn't keeping track of the time but I know it wasn't long before Jenny began to approach orgasm. After all, she'd been highly charged for hours now and hadn't had any chance for release. I didn't back down but sucked even harder and deeper. Jenny would thrust her hips up as I lowered my head. I took my hand from hers and cupped her ass with both hands. As Jenny thrust, I pushed her up until her cock was as deep in my throat was it could get.

"I'm going to cum," Jenny said. She was sweaty and her face flushed. I didn't reply but kept on sucking. "Are you sure you want to?" she asked, divining my intentions. I only nodded and kept sucking.

Moments later, the deluge came. Jenny gave a shuddering sigh and my mouth was suddenly filled with a creamy, gooey liquid. She sighed again and more pumped into my waiting mouth. I swallowed it down quickly but I could still feel the strange taste coating my tongue. A few more squirts followed as Jenny emptied the last of her seed into me. I drank every last sperm happily.

Jenny's body relaxed. Her cock went limp and slid out of my mouth. I crawled up to lay beside her. For a moment, Jenny just lay on her back, staring at the ceiling. Finally, she rolled over towards me, nuzzling her head against my shoulder.

"Thank you," she said. "That was unbelievable."

"It was unbelievable for me, too," I told her.

"Are you sure you've never done that before?" she asked.

"Beginners' luck," I said. "I guess we both have it."

Jenny laughed at that and nuzzled closer. I put my arm around her and held her tightly against me. While I lay there, holding this sexy, teenage transsexual and with the taste of her semen still fresh in my mouth, I thought about all the other sexual experiences of my life, wondering if any could compare. The only thing that came to mind was my wedding night, when I was so rapturously in love that every physical sensation felt matched by an equally powerful emotional one.

But that thought made me feel guilty, thinking about my wife. I knew I had come back too far to turn back, even if I wanted to, so I pushed the guilt away. I would have time to hate myself tomorrow but I was going to enjoy tonight no matter what cost I would have to pay in the morning.

Jenny was quiet. She hadn't stirred or said anything in a while so I thought she might have fallen asleep. I was about to wake her up, to have her move down to the couch as I knew she eventually must, when she spoke.

"I need to feel you inside me," she said.

I swallowed. "You want me to enter you, then?" I asked.

"I need you to," she emphasized. She opened her eyes and looked at me fiercely. "I need you to make me feel like a complete woman for the first time in my life."

There was no way I could refuse. "Of course, angel."

Jenny extracted her body from mine and moved into a doggy-style position. I made a vague comment about finding some condoms but Jenny stopped me before I could complete the thought. She wanted my cock in her butt with nothing in between.

I moved to a kneeling position behind Jenny. She reached back with one hand and hooked the band of her g-string and pulled it down to mid-thigh, exposing her firm, healthy ass to me in all its loveliness. I reached out and gently caressed her cheeks with my hands. Her butt was milky white with a sprinkling of freckles across it -- absolutely beautiful.

I spit a puddle of saliva into my hand and rubbed it over my dick. I did this repeatedly until I had no more saliva left. Once I felt certain I was as well-lubricated as I was going to get, I shuffled forward on my knees, bringing myself closer.

I spread Jenny's cheeks apart. Her tiny, pink butthole looked like a glorious treasure that only I could claim. I ran my slippery wet cock up and down the crack of Jenny's ass and she breathed airily as the tip brushed against her expectant opening. It almost seemed to dilate slightly, as if opening itself to me. My cock was now rock hard and I resisted every urge to simply slam it inside her.

Instead, I pressed the tip against the hole, and gently pushed. I met with resistance and didn't penetrate at all. I tried harder and Jenny cried out in pain.

"Maybe we shouldn't," I said.

"No," she replied firmly. "Don't stop no matter what."

"OK . . ." I said dubiously.

I pushed hard again. Jenny cried out but quickly buried her face in the pillow, stifling the noises she made. I suspected that it was not so much discretion about the children hearing, but fear that I would refuse if I thought I was hurting her too much.

Finally, her butthole began to yield, and the cock slipped in. With that progress made, I pushed harder. I felt Jenny's body shake as she began to cry softly, the sound still muffled. I didn't stop, though. I kept pushing until my cock was past her sphincter. At that point, all resistance ended, and my shaft slid effortlessly deeper into her body.

When I was about six inches in, I stopped. Jenny lifted her head from the pillow and looked back at me. Her face was wet but she smiled at me. "Make a woman out of me, please, Peter," she said. I pushed my cock farther in, wondering if her small body could take all of it in. To my happy surprise, the rest entered without a problem. Once I was in up to the hilt, Jenny let out a long breath.

Now it was truly time for me to turn this sweet girl into a woman. Placing my hands on Jenny's hips, I pushed her forward gently and watched as inch by inch of my dick appeared from between her tender cheeks. Once I was about half way out, I pushed back in again. Jenny grunted but I continued without hesitation.

This became our rhythm for the first ten minutes or so. I would pull her towards me, letting my rod slide slowly into her, then I would push her away, letting it slide slowly out. I could feel the tight muscles inside Jenny's bowels loosening, which was a good thing. I couldn't begin to really fuck her until I knew she was in no danger of any serious damage.

Jenny's body movement gave me the indicator I needed that it was time to proceed faster. As I pushed, she pulled herself. As I pulled, she pushed herself. Soon, she was pulling faster than I was pushing, and pushing faster than I was pulling. Effectively, she was fucking my dick with her ass, rather than the other way around. I began increasing my pace to match her. My dick was soon moving in and out effortlessly, although it was still deliciously tight in there.

As the minutes floated by, our tempo increased to a steady, rapid pace. In and out, in and out, I pushed my cock in and pulled it out. Soon, my conscious will no longer mattered, and my body was acting of its own accord. Jenny's body too seemed to be acting without instruction.

Our perfect love-making continued for an unknown amount of time. My thighs slapped against her ass and my balls bounced against hers with each successive thrust until the room was full of the smacking sounds of our frenzied passion and the air began to stink of sweat and other smells which might have been unpleasant at other times, but not at all right now. I was at last truly slamming my cock into her ass as I had been aching to do from the beginning.

I looked up and down Jenny's body. Her babydoll had bunched around her chest so I could see the smooth, white skin of her back. I leaned forward and kissed the back of her neck without breaking my stride, so to speak. Jenny turned her head and tried to kiss me, but couldn't quite reach. I knew what had to be done.

I slowed my pace until we had both stopped, then reluctantly withdrew my cock from her asshole with a sucking noise. I took Jenny by the thighs and flipped her over on to her back with one movement. She bounced on the mattress and giggled childishly.

"I want to see your face while we make love," I told her.

"We can kiss this way too," she said.

"That's right," I said. "It will be so nice to be able to . . ."

"Less talk, more cock," she said, cutting me off.

"As Her Majesty commands," I said.

Jenny was flat on her back with her knees up. I moved into a kneeling position between her legs. Placing my hands under her knees, I lifted her butt slightly off the mattress. I leaned my weight forward to keep her in that position. I peeled off Jenny's g-string and tossed it aside. She reached down to cup her balls and hold them out of the way while I renegotiated my way back into her steaming hot bowels.

It didn't take long. Her hole was plenty loose now. My dick entered without a problem and soon we were back to our old pace. The sounds of humping filled the room once again. I admired Jenny's taut body, my eyes wandering from her breasts down to her crotch. Her two little balls were bouncing up and down each time I railed her and her cock slapping against her pubic hair.

I gazed into Jenny's beautiful eyes, then leaned forward and kissed her on the mouth. Jenny put both arms around my neck and held me there tightly. Our tongues wrestled and fought inside our mouths while my cock plunged inside her ass over and over again.

Jenny lowered her head back down to the mattress and raised myself back up. She reached down and took a hold of her wildly-flapping girlcock. She began jerking herself off almost as hard as I was fucking her. The sight of this sexy nymphet stroking her dick, and the intense look of animal lust twisting her face, made my testicles begin to churn. It wouldn't be long now.

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byWannabe Chick© 29 comments/ 399482 views/ 181 favorites

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