tagTranssexuals & CrossdressersThe Babysitter's Secret Ch. 02

The Babysitter's Secret Ch. 02

byWannabe Chick©

Synopsis: This is the second installment of my series "The Babysitter's Secret." I wish to extend my sincere gratitude to all those who wrote to me to share how much they enjoyed the story. Any time I can make one of my readers cum, I know I've done my job. In the previous episode, a husband and father of two young children named Peter began an illicit affair with the teenage babysitter named Jenny Rove - a pretty young woman who Peter discovered was actually a transsexual. As our story begins, Peter is divided by his desire for Jenny and his devotion to his wife, Shawna.


Two months had passed since Jenny and I had first made love on that fateful, snowy night. At least once a week, occasionally many more, Jenny and I had found time to be alone and indulge in our secret affair. I had never believed any sexual experience could be greater than our first time together but Jenny consistently proved me wrong in that belief. Her body, that of a young woman, combined with the sex drive of a young man made her the most energetic and passionate lover I had ever known. She was capable of taking me to heights of desire and satisfaction that I had hardly known existed.

Strangely, I found that having sex with Jenny made my sex life with my wife Shawna better as well. As much as I loved Shawna, and as sexy as she still was to me, the our sex life had become stale before Jenny came along. Now that I had another outlet for my raw lust, the love-making between my wife and I was sweeter and more tender than it had ever been in the past. The physical ecstasy that Jenny provided was equal to the emotional ecstasy provided by my wife.

Of course, I was torn with guilt. I loved Shawna and I had made a commitment to her to be faithful until death. We had two twin babies together who were the centers of my existence. I hated myself for betraying Shawna but I simply could not stop being with Jenny. The girl was like a drug and I always wanted more.

My two lives were about to collide.

One day, Shawna called me from work and told me that she would have to stay late and wouldn't be home until 8 o' clock that night. Being a teacher, I always got out on the early side, and it was no problem for me to pick the children up from pre-school. At the same time that I was dealing with this practical issue, my heart was beginning to pound because I knew that Shawna's absence would mean Jenny and I could be together alone while the children took their afternoon nap.

When the time came, I left work, and picked up the twins. Once I was home, I called Jenny on the phone to tell her we had the house to ourselves.

"Peter, I can't come over," she said despondently. "I'm at the mall with my friends and my dad isn't picking us up for another hour."

"Can you come after that?" I asked.

"My aunt is visiting from New York and we're all having dinner together," she explained. "I'm sorry, there's no way I can get out of it."

"I'm so disappointed," I said, then added, "but not at you, sweetie. I understand if you can't make it. I'm just disappointed in general. I've been thinking about sucking your cock all day."

"Don't get me started," Jenny said with a laugh. "I had to go jerk off in the girl's room during fifth period because I couldn't concentrate in class. I kept thinking about your dick in my butt and I was afraid my boner would show through my skirt."

"It's nice to have that effect on someone," I said.

"You definitely do," Jenny replied. "Hey, my friends are coming back over. I should go."

"OK, honey, have fun." I hung up the phone and went into the living room to play with the kids.

The rest of the day passed uneventfully. I played with the kids, then put them down for their naps, and went into my office to grade some tests. Around dinner time, I made supper for the twins and myself and we ate together at the table while we waited for Shawna to return home. Around 8 o' clock, she walked in the front door. She greeted the children warmly, hugging and kissing them both, and then hugged me and gave me a quick kiss on the cheek. Everything seemed normal except for the strange look in her eyes.

The time came for the twins to go to bed. Once they were tucked in and the lights were out, Shawna and I watched television for a little while. She continued to seem distant and distracted. I wanted to ask what was wrong but I was concerned it might simply be my imagination.

Around 11 o' clock, my wife and I began getting ready for bed. I undressed and changed into my pajama pants. Shawna went into the bathroom and returned a minute later wearing her nightgown. I thought this was a bit odd since Shawna usually just changed in front of me. The feeling soon passed, however, because I was still very horny and the sight of my wife's large breasts bulging against the silk caused my dick to stifffen instantly.

Once we were in bed and the lights were off, I put my arm around her and began kissing her neck. Shawna remained rigid, shakely slightly. Again, I thought it was my imagination, so I continued. At last, Shawna pushed me away. "What's wrong, baby?" I asked. Then Shawna burst into tears.

My first thought was: "Oh God, she knows" but I soon found out otherwise. Shawna hugged me and held me tighter than she'd ever held me before. She sobbed into my chest for long, long minutes while I held her and stroked her hair. I kissed her forehead and whispered to her, telling her everything was alright, until at last she calmed down. Then I asked what was wrong."

"Sweetie, I'm so sorry," she said, still weeping.

"Sorry for what?" I asked.

"Today . . . I didn't really have to work late. I went to a hotel with someone from work and . . . we had sex."

The last three words were a barely audible whisper. Now it was my turn to go rigid. Although I knew I was cheating on her, the idea of my wife with another man still turned my blood cold. I wanted to yell and scream. I wanted to ask how she could betray me like that. I wanted to demand the guy's name so I could go to his place and break several bones. But I couldn't do any of that. That would make me a true hypocrite and I owed it to Shawna, after all I had done with Jenny, to give her the benefit of the doubt.

"Why?" I asked.

"It was a sexual thing," she said. "That's all. It was just about the sex. I still love you. I love you more than I ever have."

"But our sex life has been so great lately."

"I know it has! That's not the problem. The problem isn't the sex we've been having. It's been wonderful."

"So what was the problem? What did I do to drive you into the arms of another man?"

"That's just it," she said softly. "It wasn't another man."

For a moment, I didn't understand. Then the impact of what she had said struck me. Shawna had gone off to a hotel with a female co-worker. She had cheated on me with another woman. My mind felt like a cog spinning with no chain.

"I don't understand," I said.

"When I was in college," she said, "I used to . . . you know . . . experiment with other girls. I liked it a lot but I always liked men more. Being with another woman is nice but I guess . . . well . . ." she laughed. "I guess I just like dick too much."

"When did you stop experimenting?"

"Right when we first started dating seriously," she told me. "Remember the night you asked me to move in with you? I told you that I needed a night to think about it. The next day, I hooked up with my friend April. We'd fooled around a few times before. Then that was it. I thought I just needed to get it out of my system."

"But it never really left, I'm assuming."

"No. Over the years that we've been married, I've been thinking about it more and more often. I guess it was never just a phase. Maybe I really am bisexual."

"OK, so what happened with your coworker?"

"Remember Janey? You met her at the Christmas party? Well, she and I were talking that night after we'd had a few and she confessed she was into women. For some reason, I told her I was too. She said that if I ever felt like being with one, she'd be open to it. It took a year but finally I couldn't fight it any more. I told Janey that I wanted to have sex with her and we arranged this thing."

"And what happened?"

"We had sex. But it was like before. It was unsatisfying. There was just something missing. I liked the way she looked, smelled, felt . . . but she couldn't meet all of my needs. Does that make sense?"

"Yes," I admitted.

"I'm so sorry, Peter. Please forgive me. It'll never happen again."

"I should be asking for your forgiveness," I said, after a long moment.

"For what?" she asked. "This wasn't your fault."

"Not for that," I said. "I've been unfaithful too."

In the pale light, I could see Shawna's face twist. I knew she was struggling with the same quandry that I'd been struggling with after her initial confession. She was angry and jealous and hurt but couldn't very well blame me for doing the exact same thing she had done. Shawna took a few deep, painful breaths. I knew she wasn't ready to hear the truth yet so I kept silently. Finally, she asked me who it was.

"Jenny," I told her.

"Jenny!" she shrieked. "She's just a kid!"

"She's old enough," I reminded her.

"But . . . when? How?"

"Remember the night of the blizzard when she came over to babysit and had to stay the night?"

"Oh God," Shawna whispered, choking.

"We've done it since then too," I admitted. "But it's like you said. It's a sexual thing. I love Jenny, but like a neice or something."

"A neice you have sex with?"

"OK, bad choice of words, but my feelings for her are nothing like what I feel for you. You're my soulmate. She's just a . . . playmate."

"Well, I guess we have two choices," Shawna said. "Either we can get divorced or we can agree never to cheat ever again. We'll wipe the slate clean. We've both screwed up so they kind of cancel each other out."

"There's a third choice," I said.

"What is it?"

"Honey, there's something about Jenny that you should know . . ."


The next day, Jenny called me after she got out of school and asked if Shawna was home. She was, but I lied and told Jenny that we could have the place to ourselves. Once the call was finished, I told Shawna that one of Jenny's friends was going to bring her over, thinking we'd be alone. This was part of the plan. While I talked to Jenny, Shawna would wait upstairs until the time was right.

Ten minutes later, a silver Taurus pulled into the driveway. Jenny got out, waved to her friend, and skipped excitedly towards the house as her friend backed the car out of and drove away. Jenny knocked on the door and I was there to answer it.

Before I could say a word, Jenny threw her arms around me and kissed me fiercely on the mouth. I could do nothing but react as my body command. I put my arms around her slender waist, holding her tighly against me, feeling the hardness in her pants against my thigh. My tongue slipped into her mouth and we sucked at each other's faces voraciously.

Then Jenny pulled away and said, "Jesus, Peter, I'm so horny today. I haven't jerked off since yesterday afternoon and my balls feel like they're going to explode."

"Before you say another word and I'm forced to fuck you right here on the floor, there's something we need to talk about," I said.

"What is it?" she asked, concerned.

"It's Shawna. She knows."

Jenny's pale face went paler. Her mouth dropped open and she put a hand to her face to cover it. Her eyes immediately began to well up with tears. I took Jenny by the hand and guided her into the living room. We both sat down on the couch where I had first caught her, all those magical weeks ago, watching one of my porno movies with her girldick held tightly in her pumping fist.

"What's going to happen now?" Jenny asked. I knew instinctively that Jenny meant what would happen between Shawna and myself, not between myself and Jenny. The girl was the kind of unselfish, compassionate person you rarely meet. Her first thoughts were for my marriage.

"Well," I said, "as it turns out, Shawna had cheated on me too. I couldn't be mad at her for cheating since I'd done it to her and she couldn't be mad at me for cheating since she'd done it to me. I guess that's happened to couples before and it probably builds resentment, but I think we're going to recover."

"If we have to stop seeing each other, that's fine," Jenny said with a little choking noise. "I want you two to be happy. If there's anything I can do . . ."

"There is something you can do that would make a huge difference."

"What? I'll do absolutely anything!"

"Don't say that before you hear my offer."


"Jenny . . . have you ever thought about being with another girl?"

"You mean, like, a regular girl?" she asked. "Not a girl like me?"

"A regular girl."

Jenny looked at me for a moment, then an embarassed smile lit up her face. She blushed and I knew I had my answer right there. Jenny had been a virgin when she and I were first together, I knew that, but she had fantasized about sex with boys plenty before that. Apparently, she'd fantasized about sex with girls as well. I actually wasn't all that surprised. My recent experiences had taught me that perhaps everyone is a little bisexual.

"Yeah," she said at last. "I have."

"Would you like to try it?"

"Do you mean . . . Shawna?"

"She's bisexual, Jenny. She's been with women before. The person she slept with wasn't another man. It was a woman she works with. She told me that she likes men but that she can't help but fantasizing about being with women but, when she actually does it, she finds it unsatisfying. And there's a reason for it."

"What's the reason?"

"There's something men have that women don't," I said, "and that's what Shawna likes."

"You mean . . . a penis?" Jenny asked. "Does Shawna know about me?"

"I told her," I confessed. "I know I promised to keep it a secret, but my marriage was at stake."

"That's OK," she said. "I know I can trust her."

"I think this thing is going to keep happening to Shawna. She's going to try to ignore her bisexual side but it will keep building and building until she finally breaks down. But then she'll be disappointed and frustrated by the experience and everything will happen all over again. And I know that I simply can't force myself to stop sleeping with you. It would be like cutting out piece of my heart. What Shawna and I need is someone we can share who can give us both what we need. Shawna and I are like two-thirds of a circle. We need someone to complete it."

"You mean me, don't you?"

"I mean you, Jenny Rove."

Jenny looked at me, then looked away for a minute, then looked down at her hands. It was clear she was in deep thought about the issue. After all, there's a big step between fantasizing about being with other females and suddenly finding yourself offered the chance to have sex with an older woman you've known for years and who perhaps she'd never really thought about in a sexual way before.

"I think I need to talk to Shawna first," she said.

"She's upstairs."

"You said she was gone!"

"I'm sorry, Jenny. I wasn't entirely truthful. She's waiting upstairs so that we can talk. If you don't want to do it, I'll take you home. If you want to do it, she's here and waiting."

"Ask her to come downstairs."

I rose from the couch and up the stairs. I knocked on the door of the master bedroom. Shawna opened the door, an excited and anxious look on her face. I told her what had happened and that Jenny wanted to speak to her. Shawna came downstairs with me. We walked into the living room, hand in hand, and the two women smiled nervously at one another. We sat down on the couch, one of us on either side of the girl.

"Hi Jenny," Shawna said.

"Hi," said Jenny, a bit embarassed.

"You don't need to feel uncomfortable around me, hon," Shawna said. "I'm still your friend. Nothing has changed between us."

"Except that you want to have sex with me," Jenny remarked.

"Only if that's what you want."

"I do," said Jenny quietly.

"So why don't we all go upstairs and see where it leads us," I suggested.

"I don't think so, Peter," said Shawna. "If Jenny and I are going to make love, it's going to be between the two of us."

"What about me?" I asked, whining slightly in spite of myself.

"This is a sacred moment for a young girl," Shawna explained. "Can't you tell she's nervous? I think you being there will only make it more confusing for her. If it's just the two of us, then it'll be different."

"I think she's right," Jenny told me.

I looked from my wife to my young lover and thought about it. This wasn't exactly what I had planned on. I thought that the three of us having sex together, all at the same time, was what we needed. Now Jenny and Shawna were going to have sex together without me? The same old feelings of jealousy flared up again, not to mention the fact that I was going to miss out on this experience. I didn't know what to say.

"Besides," said Jenny, seeing my inner conflict, "if we like it, you can always join us next time."

"Exactly," said Shawna, whose expression told me that she rather liked that idea.

"Well, I guess it's ladies' choice then," I said with a smile. "What do I do now?"

"Take the kids and go see a movie. Take your time," Shawna suggested. She looked at Jenny, who beamed back at her. "I have the feeling we'll be a while."


Obviously, I wasn't there and so I can't describe what happened next in my own words. However, Shawna and Jenny told me every intimate detail of what happened, of how they were feeling, and what they were experiencing, so I was able to piece it together as if I had been there myself.


Shawna's heart pounded as she led Jenny by the hand into the master bedroom. The teenager closed the door behind her and briefly envisioned all the many times she'd explored the pleasures of her young body in this very room. Like her older friend, Jenny's heart was thundering in her chest. Shawna could sense Jenny's excitement and it stimulated her own.

Shawna invited Jenny to sit down on the bed, then she reached under the bed and removed a gift-wrapped package. She handed it to Jenny. "What's this?" the redhead asked.

"It's a gift for you," Shawna said. "Something I want you wear." She blushed, her cheeks turning a faint pink color. "I hope you won't think it's too inappropriate."

"I'm sure I won't."

Jenny unwrapped the gift and then opened the box. She looked inside at the outfit that Shawna had given her to wear. She pulled it out of the box and inspected it for a moment. Then she looked at Shawna with a devilish gleam in her eyes. She ran her tongue across her upper teeth.

"Why, Mrs. Fuller , you bad girl," she said.

"You'll look so sexy in that," Shawna replied. "I have something for myself to wear too. Something brand new."

"Mmm, I can't wait to see."

"Go into the bathroom and get changed," Shawna instructed. "I'll get changed in here."

Jenny skipped off into the bathroom to put on her new clothes. She shut the door and stood in front of the large mirror above the sink. She quickly stripped out of her dress and admired her body, clad only in black underwear. Then she undid her bra and let it fall to the floor. Next came her panties, which she eagerlt wriggled out of.

Looking at her nubile body, rapidlt maturing from girlhood to womanhood, she felt a rush of sexual desire and her small cock stiffened. She squeezed her B cup tits together, then ran her hands down her flat stomach and rubbed her package until her dick was hard. Ready at last, she donned her new outfit and admired herself once again, delighting at the thought of the fantasies, hers and Shawna's, that she would soon fulfill.

Meanwhile, in the other room, Shawna undressed and likewise took a moment to admire her body in the full lenghth mirror which hung on the back of the door. Her breasts were large, a true D-cup, and breastfeeding two babies had not done them any harm. For a moment, she closed her eyes, and imagined Jenny's face buried in them. Soon, it would be a reality.

Report Story

byWannabe Chick© 57 comments/ 516099 views/ 188 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: