tagTransgender & CrossdressersThe Babysitter's Secret

The Babysitter's Secret

byWannabe Chick©

Note: I just want to thank everyone for the kind responses I've received for my most recent story, "The Sisters' Secret". I was truly touched by how much I've been missed. Don't worry, I will continue that series and the Tina series and, yes, Mom's series as well. Thanks for your patience and support.

Synopsis: Peter is a loving husband and father and a pillar of the local community. Jenny is the girl next door - his best friend's daughter and the girl who babysits his children. He's always known she had a crush on him but there's a lot more about this teenager he doesn't know . . .

* * *

The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated on my wife, I had never lied to a friend, and I had certainly never slept with a girl that young before. All of that changed within a matter of hours. But you know what? I wouldn't change what happened for the world.

Years ago, I moved to the small town of Emberton, Rhode Island to take a job teaching biology and psychology at Emberton High School. I was twenty-seven years old at the time. My wife Shawna had recently given birth to our twin children, Nathan and Johanna, and I thought the job would at least provide a stable source of income. Little did I realize how much I would enjoy teaching. It really became my calling and, for the last eight years, it had been the single greatest joy in my life besides my family.

We had been in Emberton for some years when I first met Jenny Rove. She was the daughter of an old friend of mine from high school named Mike Rove with whom I'd lost touch over the years. Mike and his family had moved to South Haven, the town that bordered Emberton. He had seen my name in the paper and gotten in touch. Our old friendship had been rekindled and now we were closer than we'd ever been. Mike and his wife, Cassandra, had three children. Jenny was the eldest. She was a shy, boyish-looking kid who I always suspected of having a little crush on me.

It wasn't until later that she first babysat the twins. Shawna and I had been wanting a night out alone but we needed someone to watch the children while we were gone. None of our regular babysitters were available so Shawna suggested we call Mike and Cassandra to see if Jenny would be available to sit for us. As it turned out, Jenny had so much experience watching her own siblings that she was a natural for the job. My kids loved her and she loved them. Everything worked out so well that Jenny became our first choice every time we needed a babysitter.

I never suspected where it would one day lead.

It was a particularly threatening Thursday night in early December when I called on Jenny for the visit that would change my life forever. Shawna's mother was performing in a musical put on by a local theater group and my wife had decided to drive the two hours to watch and support her mother. The kids and I would have gone under normal circumstances but the performance was being given two hours away and the next day was a school day. I would have to be at work in the morning and the kids would have to be at school. There simply wouldn't be enough time. Shawna decided to stay overnight to avoid a late-night drive home so it would be just me and the kids.

Then I received a last-minute call inviting me to an emergency meeting of the Teachers' Union to discuss a possible strike. Despite the forbidding skies, I couldn't just refuse such an important meeting. I couldn't leave the kids alone, either. I called Mike and told him the situation.

"Do you think Jenny could come and watch the kids for a few hours?" I asked. "I know it's a school night but I'm really in a bind."

"I'm not sure . . ." he said hesitantly.

"Please, Mike," I pleaded. "I don't have any other option."

"Alright," he said after another moment. "Let me go ask her."

I waited nervously. A minute or two later, someone returned to the phone. It wasn't Mike, though. It was my favorite babysitter. "Hey, Mr. Fuller!" Jenny said in her bubbly voice.

"Hey kiddo," I replied. "So what's the final report?"

"My dad is just getting his boots on and then he's gonna bring me over," she explained.

"That's great, Jenny," I said. "Thanks so much. You're really helping me out."

"No problem! Oh wait, here he comes. See you in a few!"

"OK! Bye!"

I hung up the phone, then told the kids what was happening tonight. They were both thrilled that Jenny was coming over and could barely contain their excitement. Twenty minutes later, the doorbell rang and I opened the door to find Jenny on the steps outside my house. Her adorable, cherubic face was haloed by copper red hair and freckles dotted her cheeks and nose. Her green eyes seemed to dance.

I invited her inside and took her coat. Jenny was wearing a sky blue angora sweater and a tight pair of blue jeans, both of which seemed form-fitting to her lithe body. Although Jenny had been boyish when she was younger, she was downright sexy now. I tried not to think about it, but I couldn't help but notice how her breasts had grown from non-existent to a medium C cup in just a few short years. Her face had become more pretty and feminine. Her hips now had a lady-like curve. Her butt had formed into a round, heart shape that I couldn't help but stare at as she walked into the living room to greet the kids.

"Hey there, you little munchkins!" she cried. The twins threw their arms around her and Jenny hugged them tightly. She then launched into an immediate tickle attack that saw Nathan and Johanna rolling on their backs, laughing madly. I had to smile.

"I'm going now, Jenny," I told her.

"OK, Mr. Fuller!" she called. "Drive safe!"

"Thanks, Jenny," I replied. "Remember, if anything happens, call 9-1-1. Or if it's not an emergency, just call me or your dad."

"I will. Bye bye!"

"Bye, Jenny. Bye guys."

"Bye, Daddy!" the twins called back in unison.

I cast one last, lingering gaze at Jenny. I was amazed at how she had transformed from an awkward tomboy into a sexy nymphet who seemed to virtually ooze hormones. She was on her hands and knees, tickling the kids again, and my eyes fixated at her bubble butt. My cock immediately grew hard in my pants and, for a brief moment, I felt a kind of animal lust rip through my body. I suddenly wanted this eighteen year old girl more than I'd wanted any woman in my life. But the moment passed. I walked out the door, thankful for the cold, and climbed into my car to begin the drive to the meeting.

It was already snowing when I arrived at the appointed location for the meeting. By the time I left, about two hours later (we decided not to strike, if you really want to know), it was coming down pretty heavily. The roads were treacherous as I drove home. In fact, by the time I reached my street, I was slipping and sliding so badly that I decided not to risk going down the driveway because of its steep incline. Instead, I parked on the street, and gingerly walked down the front lawn to the door.

I opened the door quietly because I knew the kids were probably asleep by now and didn't want to disturb them since their room was right above the front door. I stepped inside and immediately heard strange noises coming from the living room. Curious, I walked into the hall and towards the living room door. When I peeked inside, I got the shock of a lifetime.

On the big screen television was one of the adult DVD's I kept hidden in my study/office. It was pretty standard fare -- a buff man nailing a woman with fake breasts -- and I rarely ever watched it. On the couch on the opposite side of the room, I caught Jenny with her eyes glued to the screen. With her left hand, she was fondling her breasts, which were clearly visible since she had pushed up her sweater and bra. With her right hand, she was masturbating furiously to the action on screen. That wasn't the big shock, though.

Instead of her fingers digging eagerly into her pussy, they were wrapped around a hard, pink cock that was sticking out of her panties.

Suddenly, things seemed to fit into place. I now knew why Jenny had been such a tomboy when she was younger. I now knew why the Rove family had made such an unexplained move from the other side of the country when Jenny was 12. The only thing I didn't know was what to do next. In a split second, I decided to sneak back out of the house without Jenny noticing me, and then come back inside. This time, I would make a lot of noise and take my time so that Jenny would know I was back and could cover herself up. I didn't want to humiliate her if I could avoid it. But it was already too late.

"Mr. Fuller!" Jenny shrieked. "Jenny, I'm so sorry!" I cried. "I just walked in a split second ago! I had no idea what you were doing!"

"Please don't be mad!" she replied, now sobbing. She was desperately trying to stuff her erect penis back into her jeans. Meanwhile, she was apologizing for what she was doing and pleading with me not to tell her parents. "I just found it and I didn't think you'd be home so early and . . . and . . ."

"It's OK," I told her. "I'm not mad at you."

"I'm so sorry, Mr. Fuller . . ."

"It's alright, kiddo," I said, trying to calm her. "Just relax. I won't tell your parents anything, I promise."

At last, Jenny got her dick back into her pants and pulled her sweater back down to cover her chest. Hesitantly, I walked across the room and sat down on the couch beside her. I picked up the remote and turned off the porno movie. Jenny was no longer sobbing, but tears were still running down her cheeks. Her eyes were red and her face was puffy. She wiped at her nose constantly.

"I'm not mad at you, Jenny," I told her. "There's nothing wrong with what you did."

"Did you . . ." she began. "Did you see . . . that I have . . . that I'm . . ."

"Yes," I admitted.

"This is so embarrassing," she said, sniffling.

"Don't be embarrassed," I said. "It's normal for teenagers to masturbate, I suppose."

"But most teenage girls don't have dicks!" she exclaimed.

"That's true," I said. "Do you mind if I ask why you have one?"

Jenny hesitated for a moment, then began her story:

So I sat beside Jenny on the couch and listened attentively as she told me the story of her life, how she had come into this world as a boy but quickly realized that had been meant to live as a girl all along. As she described the difficult times she endured as she came to this self-discovery, she began to cry softly, and I unconsciously put my arm around her shoulders to comfort her. She leaned against me and I couldn't avoid noticing how soft and warm her body felt.

Jenny continued with her story, recalling how she had managed to come to terms with her identity, and how her parents dealt with it. To their credit, both of them were extremely understanding and concerned for their soon-to-be daughter. Neither hesitated in making the decision to move to a new town so that she could begin a new life as a girl without anyone knowing her past.

"You're an amazing person," I told her with sincerity. "I can't imagine the kind of courage it took to change your life like that."

"I knew I'd die if I tried to pretend I was a boy at heart any longer," she said, sniffling away the last of her earlier crying. "This was who I was meant to be."

"I hope you don't mind me saying this," I said, "but I never would have suspected you were anything but a gen- . . . what was the word?"

"Genetic girl."

"Right. I never would have suspected you were anything but a genetic girl in a million years. You honestly look like any other girl. No, not just any other girl. You're even more beautiful and more sexy than most girls who were born that way."

"Thanks, that's really sweet," she said as she turned her face up towards mine. Her whole face seemed lit up by the compliment. "I think you're really sexy, too."

"Jenny . . ."

"I know you're married and you have kids and stuff, but sometimes I wish you didn't so that you and I could be together." I was speechless and unable to respond. "Do you ever think about me that way? I mean, what it would be like to be with me?"

"Yes," I finally admitted. "I do sometimes."

Jenny closed her eyes and lifted her face closer to mine. I knew I should push her away, tell her no, take her home and forget all of this had ever happened. But feeling this nubile teenager so close to me, knowing how badly she wanted me, I was powerless to do anything except close my eyes and lower my face to meet hers. Our lips met in a tender kiss.

Jenny pulled her face away from mine and her eyes flitted open. I smiled at her and she blushed. Then she reached a hand towards my face and gently stroked my cheek. Her hand descended down my chest and torso until there was no question in my mind about where it was going to end up. Her hand came to rest right on the bulging mass inside my pants, already rock hard from the feel of Jenny's body and the kiss we had shared.

She began rubbing me through the fabric of my pants until my cock, which I thought couldn't possibly get harder, felt like it was about to burst through the zipper. I groaned slightly and Jenny laughed softly. She was a born tease, I thought.

Well, she wasn't the only one who could tease.

I stretched my arm out over Jenny's and let my fingers rest on her crotch. Like mine, her erection was straining mightily against the denim of her jeans. It was a strange thing to be touching another person's penis, I think now in retrospect, but at the time it seemed totally natural to do. Jenny wasn't a boy who happened to look like a girl; she was a girl who happened to have the same equipment as a boy down there -- equipment that suddenly aroused my desire like I never thought it could.

For a while, Jenny and I rubbed each other in silence. Neither of us wanted to speak, it seemed, for fear of breaking the atmosphere. At last, I knew we would have to take a step further or else stop entirely and I was not prepared to finish this yet.

With one hand, I popped the button on Jenny's jeans and unzipped her fly. My fingers slid under the elastic waistband over her pants and the reddish-gold pubic hair felt soft and silky against my skin. My hand continued its expedition until I found her swollen cock. At my first touch, Jenny's entire body began to tremble and a moan escaped her lips. I wrapped my fingers around her shaft and began to stroke her gently. Meanwhile, Jenny's hand had found its way into my underwear as well. At the touch of her supple fingers, I closed my eyes and allowed the sensation to overwhelm me.

Again, it seems like a strange thing in retrospect, but at the time I did not suffer any earth-shaking notions of: "I can't believe this, I'm jerking someone else off!" or "I can't believe I'm doing this with a eighteen year old!" It just seemed to fit together so perfectly.

However, it soon reached that point once again where we had to stop or take a step further. This time, it was Jenny who took the giant leap for the two of us. She pulled my hand out of her pants and rose gracefully to her feet.

She turned to face me, smiling mischievously, then in one smooth motion pulled her sweater off over her head. She was now topless except for a black bra. She reached behind her back, unclasped the bra, and allowed it to fall away, revealing the most perfectly pair of breasts I had ever seen in my life. They were lovely, round b-cups with pink nipples the size of a half-dollar in the center.

She leaned over, grabbed the waist of my pants, and yanked them down to my ankles. I compliantly lifted my feet so she could pull my pants and boxer shorts off entirely. Then Jenny knelt down between my legs and pushed my knees apart.

At first, I thought she was going to give me a blowjob right then but, like I said, Jenny was a natural tease. She wanted to warm me up a bit more first. She leaned forward and blew warm breath on the tip of my cock, causing it to twitch erratically. Then she took a hold of my dick once again and began to slowly stroke me up and down. She did it so deliberately that it almost felt painful. I wanted so bad to shoot my load but I couldn't at this slow pace.

Jenny leaned forward, placing her chest against my crotch, so that my shaft was directly in between her breasts. She rubbed herself up and down against my dick, pushing her breasts together on either side of it. This again she did with deliberate care and slowness.

Finally, after an unknown amount of this exquisite agony, Jenny lowered her mouth towards my cock. She opened her delicate lips wide and took the head inside. Her lips sealed around it, then began to gently massage the flesh as her head bobbed ever so slightly up and down. She worked for a while just on the head, sucking it and wetting it with her saliva until her spit was running down my shaft. She paused to lick it up by running her tongue from the base of my shaft to the very tip, where my precum would form a tiny, translucent line between my dick and her tongue.

Jenny increased her pace. Soon, she was sucking harder and faster, taking more of my cock into her mouth each time her head bobbed down. I thought she might have trouble with all of my eight and a half inches, but Jenny sucked cock like a pro. She gobbled it voraciously while stroking the lower part of my shaft with one hand and fondling her own left breasts with the other.

"I'm going to cum," I whispered raggedly. I could barely breathe.

Jenny didn't remove her mouth from my cock, as I thought she might, but instead looked me dead in the eye. Our gazes locked and held fast while she continues to suck and stroke me for the final few seconds. At last, I erupted. Jenny continued to beat furiously with her hand as I pumped shot after shot of semen into her mouth. Jenny guzzled it all down without any show of disgust or distaste at all. In fact, she seemed to become hungrier and hungrier for it with each dose I gave her. By the end, she was sucking futilely at the head of my cock, trying to coax more from me.

Finally, I began to go limp. Jenny pulled her face away from my crotch and wiped a tiny spot of her cum off the corner of her mouth.

"Thank you for letting me do that," she said.

"Thank me?" I replied incredulously. "Honey, that was the greatest blowjob I've ever received. I should be thanking you!"

"It wasn't the best," she said, blushing and looking away.

"It was," I replied. "You're amazing. I get the feeling you've done this before . . ."

"No," she said plainly.

"Really? How did you get so good?"

"I spent a lot of time imagining what it would be like to suck you off," she told me. "Plus I have one myself so I know what feels best."

"That must be it," I said with a laugh.

"It's getting really late," Jenny said. "I wish I could stay longer but my parents will be expecting me home soon."

"Wow, you're right," I said. "We'd better get dressed and get you home."

I stood up and helped Jenny to her feet. I picked up my boxer shorts and pulled them over my legs, then picked up my pants and pulled them on as well. As I searched for my socks, I watched Jenny as she dressed. She buttoned her jeans first, then found her bra and sweater. Rather than put the bra on, she stuffed it into her pocket, and pulled the sweater over her head. She pulled her hair back, tugging it out of the shirt collar, and let it fall over her shoulders.

Once Jenny and I were both fully dressed and ready to go, we made our way towards the door. I stepped outside and was immediately hit in the face with a blast of cold, snowy air. One look into the night told me what the conditions on the roads would be like. It was suicidal for me to take Jenny home tonight. She would have to stay over.

Report Story

byWannabe Chick© 43 comments/ 522080 views/ 349 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: