The Babysitter - Part 4

The Babysitter - Part 4.
By Pentatonic

It was an ugly late January day. Gray skies, sleet, and dirty snow on the ground. Joe and I were walking to my house to study. “My church is having a Valentine’s Day party for teens,” Joe said, “You interested?”

“Maybe, depends,” I answered.

“Depends on what?” he asked.

“Like is it couples only? Do you have to pay to get in?” I replied. I didn’t want to go as a couple with Joe. I asked about an admission price, since there are not as many babysitting jobs in late January, and my funds were running low. I was sure of one thing, Joe had very little or no available cash.

“I think it’s open to any teen, but there will be couples there,” Joe said, “I think that they charge something to get in, to pay for the refreshments, and stuff like that.”

“Will there be dancing?” I asked.

“Yeah, I think so. They’ll probably have a CD player.”

“Are you going?” I wanted to know.

“If you will,” Joe said.

“You mean, like a date?” I asked.

“Yeah, well sorta,” was his evasive reply.

“Well, either it is a date or it isn’t. Which is it?” I demanded to know.

“It is a date,” he said.

“As in a boy and a girl?” I asked.

“Yeah, I guess so.” Another evasive answer.

“If we’re going as a couple, who’s the girl, or do you plan on two boys as a couple? I don’t think that would be a good idea, Rumors would be sure to follow,” I said.

“I kind of figured that you’d be the girl, since you already have some dresses, and you’re better looking than I am,” Joe posited.

“I’ll agree with you that I’m better looking than you, but why do you always want me in a dress. Isn’t it your turn?” I asked, “or is it that you have some evil intentions to have your way with my tender body?” I had to smile when I said that.

I paused for a moment. “I have to think about it,” I added, “If I get a babysitting job for the same evening, I’m taking the babysitting job over a Valentine’s Day party. Anyway, no matter what, I’m not going as a girl.”

The matter of the Valentine’s Day party was dropped when we arrived at my house and started to study. Ever since Mother had found out that Joe and I had kissed, we did our studying at the kitchen table, in plain view of everyone, as opposed going up to my room. This pleased Mother.

Just before Joe left, I penciled in the date of the Valentine’s Day party on the family calendar. My sister Emily saw me do this, and she came over to see what I had written. “OOH, Tinkerbell is going to a Valentine’s Day party,” she crowed, “are you going with Joe, like on a date?”

I just shot her a dirty look, but Emily wouldn’t let it drop.

“Hey Tink,” she continued, “I have a nice red dress which you can borrow. How does that sound to you Joe? Think that Tinkerbell would look nice in red?” Emily didn’t expect a response, so she left the room laughing.

“Mother!” I complained loudly. “Make her stop.”

“Just ignore her,” was my Mother’s useless advice.


I had a babysitting job with the Werners that weekend, so I drew an action movie from the library and looked at the rules for some card games. I wanted enough to keep the boys interested.

I had been unhappy that Mother had heard about Joe and me kissing. I didn’t mind telling the counselors; I just didn’t want Mother to know. So when I arrived at the Werner’s house, Mrs. Werner was still getting ready and I asked Dr. Werner if we could talk for a minute.

“Sure,” he said, “is this part of your counseling?

“Yes,” I answered, “When I admitted that Joe and I had kissed, it upset Mother. There are some things that I’d rather that Mother not know about, but I think that you as a counselor should know. Is there any way I could have a session without Mother in the same room?”

“I see your point,” he answered, “I can arrange that your sessions be one on one with the counselor. Don’t worry about it.”

“Thanks,” I said, “it means a lot to me.”


A week before the Valentine Day party, Joe and I were walking to his house from school. “Joe,” I said, “I’ve been thinking about the party next weekend. If I go, I’m not going as part of a couple. You and I can go, but not together. It’s that or nothing.

“I guess that means you won’t be wearing a dress,” he said.

“You’ve got that right,” I responded, “but that doesn’t mean that you can’t wear a dress,” I added with a chuckle.

So it ended up that Joe and I went as singles, not as a couple, and neither of us wearing a dress. There were a lot of kids who were there without dates, so coming as a single was not a problem. There were a fair number of girls, and it was a lot of fun mingling with them. Having an older sister who made me learn how to dance meant that I was a fair dancer, a lot better than most of the boys there, which meant that I did a lot of dancing.

My friend Tom was there, and after a while he and another boy came over to Joe and me.

“Joe, Chris, I’d like you to meet Fred, a friend of mine. He goes to a different school, so I don’t think you’ve ever met him. We shook hands and exchanged greetings. Then something unusual happened; I caught Fred ‘checking me out.’ I knew what this was since I had been checked out by boys who thought I was a girl, but this time I don’t think that I looked like a girl. Then I saw him check out Joe.

I noticed that while Joe and I danced with a lot of girls, neither Tom nor his friend Fred danced with any of the girls. I also noticed that they touched each other more than usual for two boys. I pointed this out to Joe.

“What do you think?” I asked Joe,

“They’re acting a lot like a couple.”

“Are they an item?” I asked.

“Could be,” Joe answered, “but then that’s not our concern.”

“I’m not sure,” I responded. “Did you see Fred checking you out?”

“Yeah, but he also checked you out, and you are much more checkable than I am.”

“Oh well, it’s not my concern,” I concluded, “or yours, unless you want it to be.”

“You’re the only one I’m interested in,” Joe said. “It’s a shame that we can’t dance together.”

“No, it isn’t a shame,” I declared, “if we danced, you’d probably try to have your way over me.”

“And that’s bad?” Joe said with a smile.

“You’re hopeless,” I said, and nothing more was said about Tom and his friend Fred.

Several of the girls made it plain that they would like to date me and we exchanged phone numbers. Over the next week some of them called me, much to the evil delight of Emily, who referred to them as my harem. “Hey Tinkerbell, another one of your harem called. Do you think she wanted to discuss clothes? Did you tell her about the fetching blue dress that you love to wear?” she said.


On the day before the actual Valentine’s Day, decided to make good on my intent to give Joe a pair of panties as a Valentine’s Day gift. I first dressed myself in panties, slip, bra and dress and headed off to a nearby lingerie shop. I had been sneaky getting Joe’s measurement. His waist size was easy. It was on the leather label on his jeans. His hip size, which was important, took more effort. I was able to wrap a string around his hips saying I wanted to compare my hips to his because I thought that my hips were getting bigger. I think he went along with it, not because of my weak excuse, but because I let him rub my butt when I measured him In any event, I had the measurements, and I was able to figure out that a size 5 panty should do the trick.

I found a darling pair of pink satin panties with little red hearts and with lace at the waist and leg holes. I’m smaller that Joe, so when I brought them to the register the clerk questioned the size, but I assured her that it was correct. I told her I had a big butt.

I put tissue paper around them and put them in a little box, which I decorated with a big red ribbon and a bow.

When I went to Joe’s house on Valentine’s Day to study, I brought my present with me. We were studying algebra, and during a pause, I said, “Joe, I have a Valentine’s Day present for you, and handed it to him.

“I didn’t know that we were exchanging gifts,” he said.

“We’re not, I don’t expect a gift in return,” I told him.

He carefully opened the gift, and when he saw what it was, he was surprised, and he began to blush. “I want you to wear them under your regular clothes, and feel the silky softness.”


Of all the girls which I had met at the Valentine’s Day party, one, Sue Hitchcock, kind of interested me. Not that she was a raving beauty, she was rather plain and a bit overweight, but she had a delightful personality. We talked several times on the phone, and I steeled my courage and asked her out for a date for the next Saturday, to catch a movie and pizza. When Joe found out he accused me to two-timing.

“Why do you want to go out with her?” Joe asked.

“Because I’d like to see a movie without someone pawing all over me,” I replied.

Sue wanted to see a new movie, which was definitely a ‘chick flic.” I certainly had no objection to that. When we sat down in the theatre, she took my hand in hers and smiled at me. After a time, I put my arm around her shoulders and she snuggled up to me. During one particularly romantic part of the movie she put her finger on my cheek and turned my face toward her. She leaned her head toward mine, and I felt her lips on mine. I squeezed her a bit, and kept my lips on hers.

I had no idea what to do next, if anything, since the farthest I’d ever gone was a kiss, except for Joe’s groping, and I didn’t think Sue wanted me to grope her. “You’re awfully shy,” she whispered to me, “I like that about you.”


Joe showed up at my house the next day, and boy, was he nosy. “Did you kiss her?” he demanded to know.

“A gentleman never kisses and tells,” I said smugly.

“That means you did, otherwise you would have said that you didn’t kiss her,” Joe posited, “Did she let you touch her tits?” I ignored that question. “You never let me touch your tits,” he said accusingly.

“How could I,” I said, “I don’t have any tits for you to touch.”

“That’s beside the point,” he said.

“No it isn’t,” I said, “I think that you’re more than a little jealous. Why don’t you go on a date with one of the girls you met at the party?”

“No money.”

“Lame excuse,” I said, “If you really wanted to go on a date, you’d find a way to get some cash. I think that the real reason is that girls scare you.”

“You don’t scare me,” Joe replied.

“That’s because I’m not a girl,” I responded.


St. Patrick’s Day was just around the corner. While my family didn’t do much about it, Sue’s family did. They were going to have an afternoon feast on corned beef and cabbage, and had invited a lot of their friends. Sue invited me, and I accepted. I told my mother about the invitation and asked her what I should wear.

“Green!” Emily interjected. “You know, maybe like that little green dress that Tinkerbell wears. I’m sure that your new girlfriend would love that,” she added with a laugh.

Mother and I ignored her. “You don’t know if it is casual, so you should overdress a little and wear a coat and tie. If it isn’t casual, you’re okay. If it is casual, you can take off the coat and tie. You might want to consider getting a green tie for the spirit of the occasion.”

That turned out to be good advice. I was able to find a green tie, and wore it with my only sport coat. When I arrived at Sue’s house, most of the men were wearing coats and ties. “I like your tie,” Sue’s Mother said with approval.

Sue took my hand and introduced me to everyone there. After that, I was talking with one of Sue’s cousins, “Sue has a kind of possessive look on her face. She better not catch you chatting up another girl, or there may be a cat fight.”

Sue and I were alone for a few minutes, when she said, “Do you like me?”

“I do, why do you ask?”

“Well, we’ve kissed, but you never tried anything further with me, and I wondered,” she said.

“I didn’t think you wanted me pawing and groping you.” I answered, remembering how I didn’t like Joe’s advances.

“Ever the gentleman,” she said. “I like that about you,” and she kissed me. “By the way, girls don’t send out engraved invitations when they want to go beyond just kissing.”

At that point, Sue’s Mother came into the room, saw Sue and I holding on to each other, and beat a hasty retreat. “Your Mother saw us,” I said.

“She did, but did you see how quickly she left,” Sue observed. “She must like you and want to encourage our romance, which is why she left so quickly.”

“Oh.” I said.

“You haven’t have a lot of experience with girls, have you?” she asked.

“Um, well, no,” I mumbled.

“How sweet,” she said with a big smile.

Sue and I continued to date, much to Joe’s chagrin, and I didn’t need that engraved invitation, but she let me know when I went too far.

I came to really love dating Sue, even if I wanted to be a girl. Boy, was I confused.


The weather in March can be just as miserable as it is in January, and on the last Saturday of the month Joe called. I could tell that there was something wrong, by the tone of his voice. “Is your mother home? We need her to drive us.”

“What’s wrong? What happened?” I asked.

“It’s Tom. His Dad caught him in bed with Fred, doing you know what, and he kicked Tom out of the house. Tom’s sitting on the curb with his clothes in garbage bags. We have to pick him up and bring him some place warm and dry.”

I explained to Mother what was going on. She put a complaining Emily in charge of Ann, and we headed off to Joe’s house. Immediately after Joe was in the car we drove to Tom’s house, and found him sitting on the curb, crying. Joe went over to Tom and picked him up and hugged him. Meanwhile I popped the trunk and loaded the garbage bags. We were there only a minute before Tom’s Father came outside, yelling, “I don’t care where you take that queer fagot, just get him out of my sight. I never want to see him again, and tell him to never come back here!” It was actually very frightening, with the yelling and crying.

“Okay, where to now?” my mother asked when we were all back in the car.

“Maybe my house,” Joe said, “we have a spare bedroom for Tom.”

We got Tom and his belongings into the house, and Joe sat with Tom on the couch, cradling Tom in his arms.

“You need to get a hold of your parents, Joe,” Mother said.

“I already did, before I called you. They should be here in about a half an hour.”

Mother sat on the couch with Tom between her and Joe. “Honey, your friends are here for you. Remember we are here to support you. You’re not alone,” she said.

When Joe’s parents arrived, Joe filled them in with what happened. “Should we contact the authorities?” Mother asked to no one in particular.

“Maybe I should call Tom’s mother,” Joe’s mother suggested.

Joe’s dad knelt in front of Tom. “Did anyone hit you?” Tom nodded his head, and between sobs, he said, “Yes, my dad.”

“Where did he hit you, on the face?” Joe’s dad asked.

“That should be obvious,” Joe said, “look at his black eye and swollen nose. The swelling is getting worse by the minute.”

“He needs to see a doctor,” Joe’s dad said, but first we need to call the cops. He then went to the phone, and dialed 911. He related what he knew to the dispatcher.

“The police should be here soon.” he reported.

A half an hour later a police car arrived, and Mr. Glynn, Joe’s dad told the officer what he knew. The officer squatted in front of Tom. “Is that what happened?” he asked Tom. Tom nodded his head. The officer then lifted up Tom’s head and looked at the black eye and swollen nose. The officer then stood up and keyed his radio. “I have a minor who was beaten by his father and thrown out of his house. Black eye and maybe a broken nose. I don’t know if there are any further injuries but he has a bump on his head, so he may have a concussion. He’s at a friend’s house. I think he needs medical attention.”

Two more officers and a child welfare officer arrived, followed by the fire department ambulance. One officer stayed to write up a report and the others left with the ambulance.

“What’s going to happen to the kid’s father,” Mr. Glynn asked the officer.

“Can’t say,” the officer said, “Someone else will make that decision.” When he was finished with his report, he thanked us and left. Shortly thereafter Mother and I returned home.


What happened to Tom was very unsettling. While I didn’t mind talking about it with Joe and Mother, I didn’t want to talk about it with anyone else. I felt that it was like betraying a confidence. Keeping quiet about it was a real struggle. On Monday, the whole school was buzzing about it. What I heard from some of the kids was nothing like what really happened, but I took no steps to correct any misconceptions.

On the next Saturday, I was at Sue’s house, just enjoying each other’s company, something I really liked to do. After a while, she said, “Remember the Valentine’s Day party? Do you remember a boy named Fred?”

I could hardly forget, given what happened to Tom.

“He was hanging around with your friend Tom,” she said. “You might remember that Fred goes to my school. Well, somehow word got out that Tom and Fred were fooling around with each other, if you know what I mean, and some homophobic bullies dragged Fred into the locker room and really beat him up. I heard that Fred had to go to the hospital. Fred hasn’t been back to school since, and someone said that his parents pulled him out of school.

“What happened to the bullies?” I asked.

“The haven’t been back to school either, maybe they were suspended or expelled, or maybe, I hope, they’re in jail.”

The thought of what had happened sent chills down my spine. If some one had connected Christine with Christopher, the same could have happened to me. Boy, I thought, have I been naive, and I vowed to be more cautious in the future.

I wondered what had happened to Tom. No one had seen him or heard from him since his Father beat him up and kicked him out of the house. I really began to hate his Father. Two young lives ruined.

It was some time later that I found out that Tom’s Mother had moved away, and took Tom with her. I suspected that it would be a long time, if ever, before I heard from Tom.


In mid-April I turned fifteen, although it was no big deal. I was still too young to be able to drive. For dates with Sue I had to get someone to drive me or take the bus, which wasn’t too safe at night.

One time, Mother suggested that Emily drive for my date with Sue. I didn’t like the idea, and told Mother. Emily just sneered. “If you don’t want me to drive, I guess you’ll have to use some pixie dust and fly, Tinkerbell.

To celebrate my birthday, my parents ordered pizza and bought a store made sheet cake. Both were okay, but only okay, not great.

After the traumatic events of the spring, I appeared to be less anxious to transition, a fact which was not lost on my counselor, a result of which was that nothing was done, one way or the other. In fact, I was anxious to transition, but now I was scared.

One day, Sue and I were looking at a book about movies, and she paused at the page describing the movie “Tootsie.” Can you imagine a guy wearing a dress and makeup?” she asked. “I mean, could you?”

I hadn’t planned to tell Sue about my cross dressing quite yet, but here was a question that needed me to answer. “Well, actually, yes.”

“What!” she exclaimed with surprise.

“I wore a witch’s costume for Halloween last year,” I admitted, intentionally omitting any mention of other cross dressing.

“You mean with a dress and makeup, and all that?” she questioned.

“Yes, all that,” I answered. “The Mother of some of the kids for whom I sit had put together a witch’s costume. A long black dress, with long sleeves and high neckline, along with a witch’s hat.” I left off any mention of what I wore under the dress or that it had a long slit up the left side.

This talk of cross dressing piqued Sue’s interest. “I wish I could have seen it,” she said.

Nothing was said as she examined my hair, face, and body structure. At last she said, “Yes, you could pull it off, and wear a dress and makeup.” Another pause followed as she considered what she said next, “Could I see you in a dress and makeup?”

“A bad idea, given what happened to Tom and Fred.”

“Yeah,” she agreed, “but if we could do it somewhere private.”

“Private places are in short supply,” I commented.

“Where did you put on the witch’s costume,” she asked.

“At home. I had to have Mother’s help,” I rejoined.

“Then we could do it there.” she suggested.

“Then there would be a problem, my sister Emily.” I advised her

“Why? She could help,” she said.

“Her kind of help would be more of a hinderance than help,” I responded, “she would probably have a lot of ideas, all of them bad, and some worse than others.”

She didn’t let it drop. “Still, a little mascara and lipstick . . .”

“No,” I said, trying to bring this conversation to an end.


A week later, Sue was visiting me at my house. Her visit was Mother’s idea, probably to see if Sue was suitable daughter-in-law material. Of course, Emily inserted herself in the conversation.

“Chris was telling me about his Halloween costume,” Sue mentioned to Mother.

“Oh yes, it was a great costume,” Mother said. I noticed that Emily had started to giggle.

“What’s so funny?” Sue asked, not quite understanding.

“Oh, the dress was great,” answered Emily, “It had a big slit up the left side, coming up to here,” she added, pointing to mid-thigh on her leg.

Before I could object, Emily continued, “But that’s not the best part. Ask him what he had on underneath the dress.”

“No! Enough! I’m sure that Sue doesn’t want to know,” I complained.

“I’m sure she does,” countered Emily. “Well, if he doesn’t want to tell you, I will.”

“Mother!” I complained, “tell Emily to shut up.”

“Given Chris’ objections, I’m sure that you now really want to know,” crowed Emily, “a black slip with four inches of lace at the hem, and long enough to be visible under the slit. Oh, we can’t forget the black pantyhose and high heeled boots,” Emily added with a smirk.

By now I was beet red, half from embarrassment and half from anger at my sister.

Emily was not finished. “Even if we couldn’t get the witch’s costume, Tinkerbell and I are about the same size, and I’m sure that I could find a dress which he could wear.”

“Tinkerbell?” questioned Sue, and the whole ugly story of why Emily called me Tinkerbell had to be brought out, over my strenuous objection.

I was ready to explode by the time the conversation was over.

Later, Sue told me that she would like to see me in a dress, “It would explain some things,” she said.

“Like what?” I challenged.

“My friends have said that you are a little effeminate. I’d like to see how feminine you’d look in a dress, with pantyhose, high heels and makeup.”

After this disaster of an afternoon, I was sure that my romance with Sue was over, but she assured me that it was not. “I kind of like effeminate boys,” she explained, “That was one of the things that initially attracted me to you.”


Sue and I continued to date through the end of the school year, after which he parents sent her to an art camp. While there, she fell in love with a “Hunk,” as she said. Our parting was more or less amiable, but she said that she had changed her mind and she wanted a man who was more “Manly.” I was hurt, but not to much, because I could not see where our romance was going.

My Mother wanted to console me. “There are lots of girls out there for you. You’ve just to get over your shyness a bit, and you’ll find another girl. After all, you’re only fifteen, way too young for a serious relationship.” She was right, but I wondered whether I really wanted another girl

Another positive: with the breakup Sue didn’t get to see me wearing a dress.

Joe thought the breakup wasn’t a bad idea. He reminded me of a Samuel Butler quote: “It is better to have loved and lost than never to have lost at all.”

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