Bobby's daddy, desparate for work, takes a job with Ms. Meisterfrau, whose family is a bit "different."

Hi, my name is Bobby Coleman and this is my story. Dad had been out of work since the museum had its budget cut. He was worried. Final demands from the landlord, the electric company and the water company lay on our kitchen table. We ate pan cakes without butter or syrup for breakfast, ramen noodles with dandelions for lunch and the cheapest hot dogs and beans for dinner. He’d set aside a little money for a tent because we’d soon be homeless. I wanted to pitch in, but wasn’t even 11, so there was little I could do beyond helping at home.

Everyday he walked to the library to use the computer to look for work. Three days before we were to be evicted, he came back looking hopeful. He had a job if he passed the background check. There was no reason he shouldn’t pass it, so maybe our worries were over. I asked him what kind of job it was. It was helping a rich lady with two boys my age. If he got the job, she’d provide room and board, so we could save most of his pay to get back on our feet.

The next morning a lady detective came by. She poked around our apartment (which didn’t take long – it was just one room with a kitchen area and a bath). Then, she sent me into the hall while she questioned dad. Finally, she asked me how I got along with the boys and girls at school and the kinds of things I liked to do. She didn’t make any faces when I answered, so I thought I did OK.

When she left, dad told me the rich lady would call later to say if he was hired. He looked nervous, even embarrassed. I hugged him and told him not to worry. I loved him no matter what and knew he loved me the same. He was doing his best, and that was all that mattered. About 4:00 his cell rang. It was the rich lady. He’d gotten the job. A Lyft would come for us at 9:00 the next morning. After packing our stuff in a couple of boxes and two suitcases from the Goodwill, we went to Wendy’s to celebrate.

The next morning we were at the curb by 8:45. Ten minutes later we were on our way in my first Lyft. I felt like Indiana Jones getting in the plane to Mongolia. On the way, dad talked to me about his job.

“You should know that this lady and her boys are ‘different.’ I want you to be very polite to everyone as this job is important to us. No matter what, you shouldn’t worry. No one will make you do anything you don’t want to do. Besides, it will only be until we’ve saved enough money to make a fresh start.”

I wasn’t sure what he was taking about, but promised to be nice to everyone and not worry if things were “different.”

The Lyft drove into the hills and up a narrow canyon to a large, 1920s Spanish style house on top of a hill. Clearly, the lady dad would be working for was rich. Her name was Martha Meisterfrau, a lawyer I’d seen on the news. She’d sued a chemical company for poisoning people or something. Anyway, she met us at the door with a warm smile.

Ms. Meisterfrau was full-breasted and tall, towering over dad and me. She wore a power blue pants suit, and had short, but feminine, auburn hair. Behind her, holding the door open, was Inez, her Hispanic housekeeper. Inez wore a black dress with a white lace apron and was a bit shorter than dad. She had a nice smile as well. I was sure this would be a nice place for dad to work and me to live.

“Hello, Billy,” she said extending her hand to my dad. “You must call me Martha. A governess is part of the family. … and you must be little Bobby. I hope you’ll be very happy here.”

“Governess?” I thought. It must have been a slip of the tongue. “Thank you, Ms. Meisterfrau. You have a beautiful home.”

“You’re very polite, my dear. ‘Ms. Meisterfrau’ sounds very formal. You may call me ‘auntie’ if you wish.”

“Thank you, ah, auntie.”

“Which bag is yours, Billy, and which Bobby’s?”

Dad pointed them out.

“Inez, would you take their bags to their rooms? … Now let me show you around.” She showed us the ground floor and pool. There was a huge living room, a library with books and computers, an audio-visual room that used to be a projection room for the silent film star who built the house, a large office and a kitchen big enough for a restaurant. The floors were Spanish tile covered with occasional area rugs. Behind the kitchen were rooms for servants. Two of the rooms would be ours.

Outside was a patio and pool. The pool had a cabana and was surrounded by lounges, tables and an enormous barbecue.

“The house is much larger than I need, but the view is magnificent, and I got a real bargain on it. Mission architecture is out of vogue, and the house can’t be torn down because its on the Historical Register.”

We took in the view of the city. You could see the ocean and barely make out Catalina in the distance.

“Do you swim, Bobby? If so you can use use the pool, but never alone.”

“I know how to swim, ah, auntie, but I don’t have a bathing suit.”

“Then we must get you one. In the mean time, you may borrow one from Sandy or Randy. You look their size. I’m sure they’ll share, if you ask. … In fact, Billy, ah, your father, needs to prepare himself, so why don’t you introduce yourself to the boys. Their room is upstairs, the second on the right. You can play together until your father is ready. … Billy, if you’ll follow me …”

I climbed the stairs, heard voices coming from the boy’s room, and knocked on the door.

“Come in!”

I opened door to a pink room with a king sized canape bed and white furniture. Two girls were sitting on the floor in front of a doll house almost as tall as me. The girl on the right had red hair and wore lime shortalls and a white blouse with matching sneakers. The one on the left was dressed the same except her hair was blond, and her shortalls and sneakers pink. Both had pigtails tied with bows the color of their shortalls.

“Hi,” I said, uncertainly.

“Hi,” said the blond, “I’m Randi. You must be Bobby.”

“Yes.”

She came over and gave me a hug and a peck on the lips.

“And I’m Sandy,” said the red head. Following her sister’s lead, she also gave me a hug and a quick kiss.

“Oh, excuse me, but Auntie Martha – your mother – said you were boys.”

“We are!” they said in unison.

“Are you a boy, Bobbie?” said Randy.

“Yes, I think so.”

“Good! … We were just rearranging furniture in our doll house. Sally’s pregnant,” he said holding up a Barbie with a bulge under her skirt. “So, we’re setting up a nursery.”

“What do you think?” chimed in Sandy.

I looked at the nursery. None of the furniture was plastic. It was all miniatures made of fine wood and fabrics. “Wow!” I said, impressed by the workmanship. I compared it to Mrs. Barnham’s nursery. She used to be our neighbor before dad lost his job. “Ah, it looks like you need a changing table for Sally’s baby.”

“You’re right. We have one, but we can’t figure out where to put it.”

“I’m good at fitting things.” It always seemed like I could get more into a space than my dad. I moved the crib, dresser and vanity, and soon there was space for the changing table.

“That’s great, Bobby!”

“Yes, thanks! You should be a decorator!”

“You think?” I said with a bit of surprise.

“Sure!”

People didn’t usually appreciate me, so I started liking these strange boys.

“What would you like to do, Bobby?”

“I’d like to try your pool, Sandy. Your mother said you’d loan me a suit, but it’s kind of cool yet.”

“Yes, later is better.”

“How about a tea party?” suggested Randy.

“My mother used to have tea parties with me sometimes – when I was little, before she died.”

“That’s sad – that your mother died. Would you like to have one with us?”

I remembered my dad telling me to be polite. “Yes, it might be fun.”

Sandy asked, “Do you have anything to wear?”

“Well, these are my best jeans – the ones I wear to church.”

“No, I mean to play dress up in. Like a party dress?”

I was about to say I wasn’t a sissy, but that would’ve been very rude, so I just said, “I don’t have any kind of dress.”

“That’s too bad. We only have one party dress each.”

They both thought for a while. Then Randy said, “I know! He can dress like mommy. We can lend him a pants suit!”

“Well, he doesn’t have the complexion to wear green, so, he’ll have to wear yours, Randy.”

Randy laid out a peach dress for himself, and a pink pants suit and white turtleneck for me. Sandy got a silk green dress from his closet. As we changed, I saw that Randy and Sandy both wore panties matching their shortalls. Seeing them in panties gave me a funny feeling that wasn’t like the one I had when they were just wearing girls’ clothes.

I was starting to put my sneakers back on when Sandy said, “Those don’t go. You need heels.” He and Randy had already put on black patent Mary Janes with lace ankle socks. They gave me pink pumps with kitten heels. Finally, Randy put my hair in a high ponytail and tied it with a ribbon matching my outfit.

Feelings I’d never had and can’t describe filled me as I walked to the boys’ play table. By the time I sat down, Inez came in with a tray of tea and little cakes called “petit fours.” I was very embarrassed to have her see me in girls’ clothes, but she just smiled as though it were the most natural thing in the world.

“Since you’re dressed like mother, you be mother.”

“What does that mean?”

“It means you’re the hostess, so you serve.” They coached me through being mother at a tea party. I was so intent on doing it right, I forgot that we were three boys dressed like girls.

When we’d finished the cakes and tea, Randy said, “You wanted to try the pool. I think it’s warm enough now. Let’s change into our suits. Which do you want.” He’d opened the closet to reveal several bikinis ranging form black to pink polkadot.

“Black, I guess.”

Randy picked a silky blue one and Sandy a rose print on a pale green background. It didn’t take them long to change and hang up their dresses. When they turned back toward me, I was surprised to see that they were flat in front. I wondered how they did that.

I just put on the bottom of mine.

“You can’t just wear the bottom, Bobby. If anyone sees they’ll think you’re going topless. Also it’s rude to have a bulge in front.”

“Who’ll see? And, most boys have a bulge in front when they wear trunks.”

“We have nosey neighbors. They’re not very nice.” Sandy pointed out the window to a house on a higher hill. “Also, mommy thinks it’s rude for boys to show bumps in their pants. Take your bottoms down and tuck it back between your legs like this.” He showed me. I copied what he did. It wasn’t as uncomfortable as I expected. Reluctantly, I put on the top, which was slightly padded. Finally, Randy handed me a bathing cap to protect my hair from the chlorine. I looked as much like a girl as my two new friends.

Sandy passed around the sunscreen. It felt strange to help the boys put it on – like I was putting it on a girl. I was glad I was tucked away, otherwise my reaction would have been very embarrassing. When we finished, we ran down the stairs in a very unladylike way and cannon-balled into the pool. We swam, splashed each other, tossed a volleyball and had a great time. I completely forgot that I was wearing a bikini.

Eventually, Inez came out to say it was time to get out of the pool. We lay on lounges and drank lemonade. Suddenly, Randy was shaking me awake and we went back up to change. Once my top was off, I noticed that I had a bikini tan – like a bra painted on my chest. The boys had them too, but their tans were deeper, so the bra impression was more obvious. I wondered what dad would think of my girlish tan.

“Thanks for the loan, boys,” I said as I handed the bikini back.

“It was new. We never wore it, and black is too dull for us. So you can have it.”

I wasn’t sure I wanted my own bikini, but I wanted to be polite. “Thanks, Sandy … Randy. … I better go and unpack. See you at dinner?”

“Yes, we eat at 7:00.”

As I put my stuff away, I couldn’t help but compare my clothes to the boys’. As opposed to the dark jeans and dull shirts in my closet, theirs were filled with colorful tops, shorts, slacks, skirts and even dresses. Instead of drab jockies, they had pretty panties. I knew they’d be called sissies and worse at my old school, but here, no one minded. I’d worn girls clothes most of the day and my only regret was a tan no one would see unless I took off my shirt.

I’d just finished unpacking when I heard my dad’s door open, followed by his floor creaking. I knocked. A woman opened the door.

The woman who opened my dad’s door had short sandy hair with blond highlights, thin brows, dangle earrings and a ruffle front silk blouse. Modest breasts met me at eye level. Looking down I saw teal slacks and pumps with 3” heels. She was too tall to be my dad, but I slowly realized that her heels would explain that. I looked up into her eyes and saw the embarrassment in them. It was my dad.

“Dad?”

“Yes, it's me, Bob.”

“Why?”

“Come in and I’ll explain. Martha, Ms. Meisterfrau, wants to raise her boys in a way that will prevent them from ever becoming ‘macho asses,’ as she put it. So, she doesn’t want them exposed to macho males. I took this job – being their ‘governess’ – on the condition that I would present, that I would dress, in a feminine manner. I'm so ashamed! I really don’t want to look like a woman, but it’s the only job I could find.” Tears were running down his cheeks, streaking his mascara.

“It’s OK dad,” I said hugging him tightly. “I know you’re doing your best – what’s best for us and I love you even more.”

“Thanks.”

“By the way, you make a beautiful woman, he he.”

“And you make a cute girl,” he said, flipping my ponytail. I’d forgotten to take the ribbon out of my hair.

“Oh! It’s a long story.”

“I’m sure it is. … So, now that we both know, what do you think? Should we call it quits?”

“No. You need – we need – this job. Everyone seems nice enough – don’t you think?”

“Yeah, I haven’t picked up on anything sinister. … Do the boys seem happy?”

“Yes, they love being sissies. … I guess I shouldn’t use that word. They love wearing girls' things and acting like girls.”

“Do they feel they’re really girls, but in the wrong bodies?”

“Not that I could tell. They told me they were boys. So, I don’t think they feel like girls inside.”

“But, they’re happy. Interesting.”

“How long are you going to keep this job, dad?”

“I committed to a year, minimum.”

“Will we have enough saved by then?”

“I think so. It depends on the job market.” He looked as the woman’s watch on his arm. “It’s almost time for dinner.”

Dad went to Ms. M’s office. I went to the dinning room, where Inez showed me my place on one side of the table. The boys came in next, wearing pleated skirts and blouses. They sat opposite me. Finally, dad and “auntie” came in, sitting at either end of the table.

“Boys, this is Mr. Coleman, who’ll be your governess for at least the next year. I want you to obey him as you would me or Inez. In addition to what you’ve been studying, he’ll be teaching you French, drawing and art history. You’ll continue to study ballet and music at the Academy. Please introduce yourselves.”

“Hello, Mr. Coleman, I’m Randy Meisterfrau.” He smiled, dipped a curtsy and sat down.

“Hello, Mr. Coleman, I’m Sandy Meisterfrau,” he said in similar fashion.

“Hello, boys, it's a pleasure to meet you. I hope we’ll have a fruitful year.”

“Now, Bobby, as I am sure your father's told you, you’ll be studying with Randy and Sandy, but you need not dress as they do – unless you wish. I do see that you’ve chosen to wear you hair in a ponytail. I think it's very becoming that way.”

Damn! I’d forgotten to take the ribbon out of my hair. “Ah, thank you, auntie.”

She led us in grace, then we all tucked in. The dinner was the best I could remember: hot fresh bread, Caesar salad, chicken Cordon Bleu, roasted potatoes, snow peas and strawberry shortcake. Inez certainly knew how to cook. I made a mental note to see what I could learn from her.

At 7:30 the boys were told to get ready for bed. Ms. M followed them up. They came down in baby dolls and lay on the floor as we watched Matilda. I was on the sofa. Sandy’s panties got twisted and a diaper showed at their leg. Randy, had a diaper peeking out at his waist. When they got up after the movie, Sandy’s baby dolls had a small damp spot.

When we got back to our rooms I told dad what I saw. He said Ms M didn’t want the boys growing up too fast.

The next day was Sunday and we all went to Church – the boys in dresses and me in my good shirt and jeans. After church, Ms. M said that she didn’t think jeans and sneakers were suitable for church and gave dad money to buy me something dressier. He was wearing a skirt and blouse, so I was afraid I'd wind up with the same. I needn’t have worried as he bought me blue boys’ slacks and black Oxfords.

When we got back to the house, everyone was out by the pool. Dad changed into a maroon one-piece bathing suit. As he did, I saw his breasts. They seemed to be part of him. All I could do was stare with my mouth open.

“Oh, my breasts,” he said. “Don’t they look real?”

“Yeah!” I continued to stare.

“They’re made of silicone and glued on. The edges are blended in with waterproof makeup. Want to feel them?”

I did. “They feel warm, like they’re real.”

“Yeah, they warm up after you wear them a while. I’d let you try them, but they wouldn’t fit your chest.”

“Ah, no thanks, dad. I’m not ready for tits!”

“Well, you seem to be ready for bras,” he said – looking at my bra tan and grinning.

“It’s from this dumb bikini! The boys said I wasn’t supposed to wear it without the top – it would shock the neighbors.”

“Well, you should have told me when we were shopping. I would have gotten you a boys’ suit. … By the way, you look as cute in a bikini as any girl your age. … You want me to put that ribbon in your hair?”

“No! I told you, I forgot it was there.”

“OK. OK! I was just pulling your chain.”

That didn’t stop me from remembering how cute I looked with a ponytail. … Anyway, we swam, had a good time and my bikini tan got deeper. When I got out of the shower the next morning, the boy in the steamy mirror seemed to be wearing a bra.

Each day we had class in the library: academic subjects in the morning, drawing and art history in the afternoon, and swimming for PE at the end of the day. Instead of feeling normal in my pants and shirt, I felt out of place. I was the only male without a skirt. It was weird: how could a boy, dressing as a boy, be out of place? Worse, once I had my bikini on I felt part of the group.

One morning, while I was combing my hair, I decided to tie my hair in a high ponytail like Randy had the first day. Everyone, including dad, said how nice I looked. It made me feel more like I belonged.

It didn’t help that dad went to the salon every Saturday and came back more beautiful each time. He started wearing makeup all the time, and his nails became more feminine: first shaped, then sporting clear polish, then a deep red gloss and finally extensions. His hair style evolved until he came home with a perm. I still loved him, but he felt more like a mom than a dad.

Then, one Saturday evening, he went out alone. He came back a little tipsy with his makeup smeared and a funny smile. After that, he got larger breast forms and a revealing cocktail dress. Many Saturdays he didn’t come home until late Sunday morning.

Ms. M didn’t seem to mind. When I told her I was worried about him, she said, “Every girl needs a little fun. Don’t worry, he won’t get pregnant.”

Meanwhile, I’d worn out my underpants, which weren’t new when we’d arrived. I asked Inez to buy me new ones. She said she would, but not till next week. She did have some panties in her cupboard, as she’d mistakenly bought too many. I could have them immediately if wearing them didn’t bother me. This was all matter of fact, without questioning my masculinity.

I didn’t see the harm, so I said “Thank you.”

“Let me know if they fit.”

I told her the panties were comfortable, and soon panties replaced my jockies.

One Saturday night, when dad had gone out, I was feeling lonely and went up to play with the boys. They wanted to play family, with them being the mother and auntie, and me the baby. It was late, so they wanted to get me ready for bed. They had their own baby bottles they took to bed. I laid down. They gave me a bottle of chocolate milk to nurse while they diapered me. I thought they were just pretending, but they actually powdered and diapered me. They were about to put a baby doll set on me when Ms. M came in to get them ready for bed.

When she saw me diapered and nursing the bottle, she asked “Would you like to sleep with the other babies tonight?”

I was lonely, so I said “Yes, please.”

She checked my diaper and tightened the fit. Then she put us all in baby dolls and had us get in the bed -- which was more than big enough for three. She said a prayer with us, gave us new bottles and kisses, turned off the light and left.

“I need to go to the bathroom before I go to sleep.”

“Were not supposed to get out of bed till morning. Why do you think you're wearing a diaper?” asked Randy.

“And why do you think she gave us bottles to nurse?” asked Sandy.

“You mean she wants us to use our diapers?”

“Well, duh!” they both said.

“That’s gross.”

“Babies aren’t gross, and this is our baby time. We have baby time every night from bedtime to breakfast.”

“Doesn’t it bother you to wet?”

“No, its nice. You’ll see,” said Sandy.

I didn’t want to see, but I couldn’t stay awake. I started wetting during in the night and woke up. It wasn’t as bad as I expected. In fact, Sandy was right, it felt nice. When I got more awake I felt Randy curled against my back with with his arm around me. Sandy was facing me with his thumb in his mouth. I didn’t feel lonely. I relaxed and wet a bit more. Then I fell asleep again.

In the morning, Ms, M came in and woke us up. She removed our diapers and cleaned us with baby wipes. Then we were sent, one by one, for showers. My turn was last. When I came back, Sandy and Randy were in big girl dresses, ready for church.

“I see that you’re wearing panties now, Bobby. Would you like to wear a dress to church like the other boys?”

I wanted to belong, so I said, “Yes, please, if I may.”

“Of course you may, dear. It’s entirely up to you.”

She brushed out my hair and got out a couple of ribbons. “Do you want your usual ponytail, or pig tails like Sandy and Randy?”

“Pig tails please.”

Ms. M put pink lipstick on each of us and we all went down to the car. As I passed the mirror I knew that I was a perfect sissy.