It Started On A Rainy Afternoon - Part 1
By Pentatonic

It started on a rainy summer afternoon when I was seven. My sister Emma is two years older than I am and she and I get along. After lunch we had started playing board games, as we often did when we could not play outside. It was about two in the afternoon when my sister stood up and declared, “I’ve had enough of these board games. Let’s do something fun and different.”

“Like what?” I asked.

“You know, people say we look alike. Let’s see if that is true. Come on up to my room. I’ve got an idea.” I knew that I had a ‘pretty’ face, and had been mistaken for a girl on numerous occasions.

Mother had left to run some errands shortly after lunch. “Can I trust you two to stay out of trouble? I’ll be back in a few hours,” she declared. We assured her that we would be ‘model’ children, but, as it turned out one of us would be a ‘model’ in a different way.

Even though I am younger than my sister, we are close in size. I wear my hair a bit on the long side, mainly as an expression of independence, or so I thought.

When we were in Emma’s room, she went to her closet and took out a dress. “I’ve grown since this was bought, but it might fit you.” The dress was a maroon taffeta party dress with a full skirt which was gathered at the waist. It had a big bow in the back, a fitted bodice and puffed short sleeves. It positively shimmered.

I was surprised. Not that I would be wearing a dress, because I had snuck into her room in the past and had tried on that very same dress, but because she had suggested it. I gave her a funny expression, indicating that I did not like the idea. In truth I did like the idea, but I just didn’t want her to know it.

“Oh, come on,” she said, “I know that you have tried on this dress before. I just want to see how you look.”

I just made a few incomprehensible noises and wondered how she knew.

“Come on, it won’t hurt you. It’s only a dress,” she said as she held it out in front of me. “Take off your clothes,” she commanded. I shook my head in disapproval.

“It’s not like I haven’t seen you naked before. It was only a few years ago that we stopped taking baths together.” She had me there, and I took off my shirt and shorts. “Take off your underpants,”she added, “I have a pair of panties for you to wear.” With that she opened a drawer in her dresser and handed me a pair of pink panties. Reluctantly I took off my underpants, sat on the bed and pulled on the panties, during which time she appeared to focus on my private parts.

“Can you do something about that bulge?” she asked, pointing to my crotch. I reached into the front of the panties and pushed everything back. “Better,” she said.

She appeared to study me for a minute. “I think that you’ll need to wear a slip,” she commented, and retrieved a slip from her dresser. “I’ll bet you’ll like it,” she said. “Hold up your arms,” she added and she let the slip slide down my body. She was right, I did like the way it felt.

She then picked up the dress and slid it over my head. I loved the feeling. “Turn around and I’ll zip you up.”

“You ready for some shoes?” she suggested. I nodded my head. She handed me some short white socks, with flowers embroidered on them, which I put on. She then handed me a pair of black Mary Janes, which I also put on. She helped me with the strap.

“Walk around, and let me see how it looks,” she said. After I walked around a bit, she said, “give it a twirl.” When I did, the skirt of the dress flared out. The feeling when it came back down was very pleasant.

“Very good,” she said, “now let me do something with your hair.” I sat on a chair, and she brushed and gathered my hair into a feminine style. When she was finished, she suggested, “Stand next to me in front of the mirror, and admire yourself,”

When I did, I was astounded. I actually thought that I looked very pretty; a lot like Emma had looked a few years before. “From the smile on your face, I can see that you like the way you look,” she said.

“Do you like being a girl?” she then asked. I paused before answering.

“Yes,” I said softly.

“In that case, you need some girl lessons, like how to walk, how to stand, how to sit, hand gestures, and very importantly, to remember to sit when you pee,” she said. The last part brought smiles to our faces.

After a few lessons, Emma said, “Mom should be home soon. Let’s show her how you look.”

“I don’t think so; she might not like it and get mad at us,” I responded.

“But she might like it,” replied Emma. “We won’t know if we don’t try it,” she replied. The question became moot, because at that instant we heard Mom open the front door.

“Emma, Jason, I’m home,” Mom announced. “Come down and help me get the car unloaded.”

There was nothing to do but for me to go downstairs as I was. I went first.

“Emma, why are you wearing a dress?” Mother asked. Then she paused when she saw Emma follow me down the stairs. She had a confused expression on her face, and paused for a few moments while she took in what she saw. “I imagine that you have a reasonable explanation for all of this?” she questioned.

“We wanted to see what Jason would look like as a girl,” Emma answered.

“Emma, what’s this ‘we’ business? This has all the earmarks of something you would come up with,” Mom said. “Jason, was any of this your idea?” I could have said ‘No’ and got Emma in trouble, but I didn’t want to do that.

“Emma may have suggested it, but I went along with it,” I confessed.

“I see,” Mom continued, “I leave you two alone for a brief time, and come home to find my son in a dress.” She paused as she looked at me. “However, I must say, you look very pretty,” she added with a smile.

After a minute of silence, Mom asked me, “Do you like wearing a dress?”

“Yes,” I said softly.

“I see,” Mom added, not convincingly. “Do you like being a girl?”

“Yes.”

At that point, Emma suggested that I give Mom a twirl, which I did. Mom had to smile at this. “I see you decided to put on a slip and panties. Very nice.”

“You’re not mad at us, are you?” Emma ventured.

“Not mad,” Mom answered. “Surprised? Yes; mad? No.” Both Emma and I smiled in relief.

* * *

A few weeks later, Mom surprised Emma and me when she came home with a dress, two skirts, two tops, shorts, capri pants, a full slip, a half slip, tights, socks and panties, all for me. “We need to buy you shoes, but you have to be there to make sure they fit,” she explained.

I now had my own wardrobe, which I hid in the back of my closet, in case a friend came over to the house.

A week later, Mom took us shopping. I wore shorts and a top and Emma’s Mary Janes. Of course I wore one of my new panties. In fact, ever since Mom had bought them for me I wore panties pretty much all the time, no matter how I was outwardly dressed. I acquired three pairs of shoes that day, trainers, mocs, and a pair of dressy patent leather pumps. As we were ready to head back home, we passed an earring kiosk. “Would you like to get your ears pierced?” Mom asked. I did.

Because I was dressed as a girl when shopping, Mom noted that she could not call me ‘Jason.’ “Have you picked out a girl’s name?” she asked.

“What would you have named me if I was born a girl?” I asked in return.

“Margaret,” she answered.

“I like Margaret,” I said. That’ll be my girl name. Maybe Peggy, for short.” So thereafter, when dressed, I used Margaret or Peggy, but only when dressed. Sometimes I was called Peggy when dressed in my boy mode, but nothing came of it.

Over the next months, I dressed whenever I could, sometimes with Emma, and sometimes by myself. This did not go unnoticed by Mom. “Jason,” she asked, “I need an answer. Do you think of yourself as a girl in a boy’s body?”

“Sometimes I do, and sometimes I don’t,” I answered.

Mom, Emma and I knew that sooner or later we had to let Dad in on my dressing. While Mom was okay about it, and appeared to approve, the same was not true with Dad. He made it very clear that he didn’t like it at all. After that, I didn’t dress when Dad was around, except that I wore panties nearly all the time except when I was at school.

* * *

When Emma was twelve, her body began to change. One Saturday, when Dad was off playing golf, Mom called to both Emma and me. “Girls,” she said, “I think that it’s time for Emma to get a bra. Peggy, you might as well come along, because buying a first bra is an important time in a mother’s and girl’s life, and unfortunately it is an experience you will never have, so the best you can do is experience it second hand.” Mom did not realize that I had been researching bras and breast forms on the internet, and I expected that I would be buying my own bra in the near future.

As it turned out, I got a training bra the same day as Emma got her first bra. We were in the lingerie store with Emma being fitted for her bra. The sales clerk looked at me, and said to Mom, “How old is your other daughter?”

“Eleven,” mom replied.

“You know, you might as well buy her a training bra now, even if she doesn’t need it at this time. That way she will be used to wearing a bra when the time comes when she will need it.” Emma chuckled at this comment.

Both Emma and I went home from the store wearing bras. When we were home, we compared them. “I’m sorry for horning in on your experience of buying your first bra,” I told Emma.

“That’s all right,” she said, “It was a neat ‘sister’ event. At least now that you have your own bra, you won’t think of snapping my bra straps” She paused and a wicked smile appeared on her face. “You going to wear it to school?” she asked.

“Hardly,” I said.

Over the next few years, Emma and I became more and more like sisters. We were able to share the development of her breasts and her first period. “You should be happy that you’ll never have to experience this,” she commented. However, I learned a lot, and knew how to act when I had a ‘pretend’ period.

* * *

Because of my close relationship with my sister, I did not have a lot of male friends. One of my few friends was Steve, who I had known since grade school. While some of my male acquaintances commented that I was acting ‘girly’ at times, Steve and I had a close friendship and when I slowly became more ‘girly’ he didn’t notice because the change was gradual.

While I didn’t have a lot of male friends, I did have a number of female friends. None of these acquaintances were of a romantic nature, but because I was in touch with my feminine side, I was almost treated as one of the girls.

Steve and I entered the same high school at the same time, and shared many of the same courses. I had always been a good student and Steve and I would study together. As a result of helping Steve, I gained a greater understanding of the course material, which did good things to my grade point average.

Our high school hosted several dances over the year: Homecoming, Halloween, Winter, and Valentine’s day. All students were encouraged to attend, but since freshmen were at the bottom of the ‘pecking order’ most were unable to find a date. Because I was friends with a lot of girls, I was able to arrange dates for quite a few of my male acquaintances, but, unfortunately, not for myself. “You’re a great guy,” one said, “but not macho enough.”

While Steve may have been macho enough, it became readily apparent that he was deathly afraid of girls. Even with my intervention, he was unable to get a date for the Homecoming dance. Both Steve and I attended, since it was permitted to go ‘stag.’ I enjoyed myself. Over the years my sister had taught me to dance. When this was discovered, I had no shortage of dancing partners. Steve, on the other hand, was not a good dancer and was too afraid to ask a girl to dance.

On the Monday afternoon after the Halloween dance, Steve and I were studying together. “You seem to have had more than your fair share of dancing,” he commented with a trace of bitterness.

“You’ve got to get over your fear of girls,” I suggested.

“How am I going to do that?” he asked.

“Let’s pretend that I’m a girl. Now try out a pickup line,” I suggested.

“Okay, he said. “Here it goes.”

“I don’t suppose that you’d want to dance with me?” he tried as a pickup line.

“Way too negative. It sounds like you want the girl to refuse and you’re leaving them an out. A girl might say that she’s guarding the purses for the other girls who are dancing. She might say that her boyfriend is in the washroom. She might say that she doesn’t like the song the DJ is playing. That won’t work.”

“Then what could I say?”

“How about: ‘I could see your aura from across the room, and I just have to dance with you’.”

“I could never say that,” he responded.

“Okay, then pick out a girl who is less attractive. Approach her and say: ‘I’d like to dance with you.’ and hold out your hand to her. Don’t look for the prettiest girl, look for a girl who hasn’t been asked a lot. Of course, she might be as afraid of boys as you are afraid of girls and shoot you down.” I explained.

“Well, anyway, I’m a lousy dancer,” he said.

“Then you need to practice,” I responded.

“Who will I get to practice with?” he asked.

I didn’t answer him. I would love to dance with him as a girl, but I wasn’t ready to reveal that secret to him. We spent the rest of the afternoon grinding through algebra.

Later that week I asked Emma if she would teach Steve to dance. “Why don’t you do it?” she asked, “you’re a better dancer that I am, and you know the girl steps.”

“You know why I can’t do that,” I answered, “my secret might come out.”

“How?” she said, “Does your feminine side have a crush on Steve?”

“Not just my feminine side,” I admitted.

“Your crush is going to go nowhere until you tell him.”

“Maybe, but not just right now,” I said as an excuse.

* * *

That week I suggested to Steve that I teach him how to dance. “But you’re not a girl,” he complained.

“I don’t see how that makes a difference. It’s not like we’re going to kiss or have sex with each other,” I responded icily. The idea of kissing Steve pleased me, but I couldn’t let him know that.

We cleared an area in the rec room, and I plugged in a boom box. From dancing with my sister, I had a fair collection of CDs appropriate for teaching dancing. Steve and I started with fast dances, everything from classic swing to acid rock.

After quite a few dance lessons, I decided that Steve needed to learn how to dance slow dances. “Slow dances are more than hugging on to each other and aimlessly shuffling around the floor. There is a proper way to hold on to each other, and there are definite steps you have to learn,” I explained as I put a CD of waltzes in the boom box. “Now here’s how we do this. Come over and face me. I’ll put my left hand on top of your right shoulder, and you put your right hand around me on my back. Now you put your left arm out to the side, and I’ll do the same with my right, and we clasp our hands. Got it?”

“You’re supposed to lead, which means that when you want to go forward, I can feel it with my left hand. When you want to go backwards you pull me with your right hand on my back. You indicate turns with your other arm,” I added.

“This is too complex,” he complained.

“No, it’s not. Think of all the people you’ve seen dancing slow dances. They learned,” I responded.

“Now for the footwork for a waltz. It is in 3/4 time, and you count one, two and three, with emphasis on ‘one’ when you step forward with your left foot, and I step back with my right. On ‘two’ you move your right foot forward and to the right. On ‘three’ you bring your left foot next to your right. You then reverse the process. This is a box step, and you pretty much stay in the same place when dancing. I think that we’ll save the more complex stuff for later, after you’ve mastered the box step,” I explained. “Before we try it to music, I’ll count it out slowly until you get the hang of it.” Steve took me in his arms and we went through the drill. Being held by Steve was one of my long standing fantasies, and I enjoyed every second of it.

I then put on some music, and we danced. “You smell kind of nice; a little girly, but nice,” he commented as we were close to each other.

“Yeah, I grabbed my sister’s body wash by mistake this morning,” I said. It wasn’t by mistake. I wanted to smell girly for Steve.

As we continued to waltz the box step, Steve and I moved closer to each other. Whether by mistake or intent was not clear, but I liked it. After a while our bodies were touching, and at that point I could feel Steve getting an erection. A few minutes later, Steve suggested we take a break, and he sat down on the sofa. I joined him there, sitting as close as I could to him. I could see his trousers ‘tenting’ over his erection. He noticed my interest.

“I don’t know why that happened,” he said as an explanation, “it just did.” I was glad that I had ‘tucked’ and my penis was held firmly by my panties, so I didn’t have a visible tent. That didn’t mean that I didn’t have an erection. I did, but it was concealed and a little painful.

“Did I turn you on?” I asked coyly, knowing full well that was exactly what happened. “Do other boys make you hard?”

“No, it’s never happened before,” he said, “it’s just that sometimes you seem to be a lot like a girl.”

“But I’m not. We can sit here until it goes down, or you can go into the bathroom and deal with it,” I suggested.

“Or you could do it for me,” he said with a foolish smile on his face.

“Not a chance,” I responded, even though I really wanted to do so.

Over the next weeks, every time we danced a waltz, Steve got an erection. I finally decided to do something about it. Before Steve came over I did my hair up in an androgynous style, put on my sexiest panties, which were brief and made of nylon. I borrowed some of Emma’s perfume and put on a tight pair of girls’ jeans. This time I didn’t tuck.

True to form, when we danced the waltz, Steve got hard. We sat down on the couch, next to each other.

I turned to face Steve and said, “Steve, I need a truthful answer from you. Remember that you said that I turn you on? Do you think you’re gay?”

Steve paused to contemplate an answer. “I’m not sure. I’m not attracted to any other boys, and sometimes you seem to be more a girl than a boy. You look like you’re wearing girls’ clothes and you sure smell like a girl, not that I’m complaining.” With this last part he smiled. “If you put on a dress and some makeup, you’d be a pretty girl.”

Steve looked at the bulge in the crotch of my jeans. “Looks like I’m not the only one who’s turned on.” With that I blushed. “You even blush like a girl,” he added.

“If I was a girl, would you try to kiss me right now?” I asked him. He didn’t verbally reply, but rather put his hand behind my head, pulled me toward him, and kissed me.

“Does that answer your question?” he said.

“It certainly does!” I said, and with that I kissed him back. “Steve, I have to confess that I wish that I had been born a girl, and one of these days I just may do something about it. By the way, I think what we said and did today should remain a secret from everyone else.”

“Does that include me?” came a voice from the doorway. It was Emma. “Am I interrupting anything, I hope?” she said, “because it certainly looks that way. Not that I’m sorry, of course,” she added with a snicker. “Margaret, we need to talk, and soon,” she added.

“Who’s Margaret?” Steve asked.

“I am. That’s my girl name when I’m dressed as a girl,” I answered.

“Does Mom know that you and Steve have been kissing?” interjected Emma.

“It’s our first kiss!” I said as an answer to her question.

“Awwww,” responded Emma, her voice dripping with insincerity, “I interrupted a first kiss. Isn’t that so sad?” and with that she chuckled. “Mom should be home soon, so you two lovebirds better clean up your act,” she added as she left the room.

“I think that you’d better go,” I told Steve.

“Before I go, answer me one question, are you wearing any girl’s clothes now?” asked Steve.

“Yes,” I responded, “These jeans, for a start, and the panties under them,” I answered.

“Could I see them?”

“My panties?” I replied.

“Yes.”

“I guess so,” and with that I unzipped my jeans and slid them down my legs, exposing my panties.

“Wow!” Steve said, “you did this just for me?”

“Yes, but I didn’t expect for you to see them. I just feel sexier when I wear panties, and these are my sexiest.”

“I’m impressed,” he said as he picked up his jacket. “Why are you doing this for me?”

“Because I think I might be falling in love with you.”

He blushed. “Maybe I’d better go,” he stammered. He gave me a gentle smile and left.

* * *

Emma was waiting for me after Steve left. “In my room,” she commanded. “You want to tell me what’s going on?”

“Well, I was teaching Steve how to dance. . .” I started to say.

“I know that!” Emma interrupted, “cut to the chase.”

“I was teaching Steve the waltz, and when we were dancing he got an erection.”

“Just once, or every time?” Emma asked.

“Just about every time,” I answered.

“And what did you do about it?”

“We sat down on the couch until his erection went away.” I said.

“Nothing more? You didn’t jerk him off or give him a blow job?”

“Of course not!” I responded indignantly.

“That’s too bad,” commented Emma.

“You mean that I should have?”

“I bet that Steve would have liked that,” answered Emma, “but of course it probably would have been better if you were wearing a skirt at the time.”

Between Emma and me, we decided that I would dress completely for the next dance lesson. I wore a royal blue dress with a mid-thigh hem. It had a full skirt which was gathered at the waist, and a loose bodice with shoulder straps. At Emma’s insistence, I wore nylons and a garter belt, a bra stuffed with socks, a slip with a lace hem, and my black patent leather pumps.

When Steve arrived, he was astounded. “Wow, you look great. Even prettier than I imagined.”

We started dancing, and almost immediately he began to get aroused. I was almost certain that his reaction was partly due to the way I was dressed. “You got dressed up, just for me?” he asked.

“A girl wants to look good for her special guy,” I responded. We sat next to each other on the couch, our bodies touching. I intentionally let the skirt of my dress ride up, exposing the top of my nylons and the tips of the suspenders from my garter belt. This really caught his attention.

“Remember the first time it happened, and you asked me if I wanted to do something about your arousal?” I asked.

“Yes,” he replied.

“Is that offer still open?” It was, and this time I did something about it.

* * *

With Halloween just around the corner, Steve’s dancing lessons were over, and the topic of discussion became the Halloween dance. “You wanna go to the dance?” Steve asked.

“I might,” I answered, “but the big question is what to do for a costume.”

“How about Snow White or something like that?” he asked.

“No dress,” I exclaimed, “Remember I have to show up at school on the Monday after the dance, and I don’t want anyone having seen me in a dress.”

“But if you don’t look like a girl, I can’t take you as my date,” he complained.

“Then we’ll have to go stag,” I concluded, which is what we did. There were a fair number of girls there without dates, so neither Steve nor I were wanting for dance partners.

That pretty much set the tone for the remainder of my freshman year and all of my sophomore year. What changed at the beginning of my junior year was that I had a driver’s license. Not only a license, but also my own car. It came from my Mom’s Aunt Beth. Aunt Beth failed her renewal driver’s license test, but she had a car, which she gave to me under the proviso that I would chauffeur her around on Saturdays and two evenings a week. This was a small price to pay for having a car. What was even better was that Aunt Beth kept title to the car, which meant that she paid for the insurance and repairs, and she gave me money for gas. My Aunt had first made the offer to Emma, but Emma turned it down.

Aunt Beth liked to go to ladies events, such as bridge parties, all of which were all female. On one of the Saturdays I drove Aunt Beth to my house to visit with Mom. During the visit she mentioned these all female events.

“It’s a shame that Jason isn’t a girl. If he were, he could participate with all of the ladies,” Aunt Beth commented.

“That shouldn’t be a problem,” my Mother said, and she explained my cross dressing in detail. “Not only that, but Jason sometimes wishes he was born a girl,” my Mother added. With that, my Mother asked me to join her and Aunt Beth in the living room.

“As you know, your Aunt goes to a lot of affairs which are for ladies. It might make sense if you dressed as a girl when you took your Aunt to them. Why don’t you go upstairs and come back down as a refined young lady?” Mom asked. I couldn’t very well refuse, given that the car was in the balance. Actually, I didn’t want to refuse, because it would give me more opportunities to dress. Therefore, I did as I was asked.

One can imagine the surprise on Aunt Beth’s face when I came back down. I was wearing a knee length pleated dark blue skirt, a white blouse with a ruffled front, pantyhose, and black pumps. Naturally, I was also wearing panties, a half slip and a bra. I had brushed my hair in a girl’s style, put on some mascara and lipstick, and wore some simple jewelry.

“Oh dear,” my Aunt exclaimed, “you look absolutely darling, much better than I imagined.”

“Give your Aunt Beth a twirl,” suggested my mother. Since I liked the feeling when I twirled, I immediately complied. Mom explained that I used the name Margaret or Peggy when dressed as a girl, much to Aunt Beth’s approval.

Aunt Beth suggested that I spend weekends at her house, as Margaret, and only arrive and leave as Jason. This was not a problem, because I liked being Margaret as much as possible. Then there was an additional benefit. I could go out on dates with Steve while dressed as Margaret. Some Fridays, when Dad wasn’t around, I would dress at home for a date, and arrive at Aunt Beth’s house already dressed. I could also go out on Saturday evenings when Aunt Beth did not have plans for the evening.

Living at Aunt Beth’s house improved my femininity. Aunt Beth would gently correct any of my mistakes in poise and deportment.

I only had a few chores, because Aunt Betty had a housekeeper who came over on the week days. Usually the housekeeper had left by the time I arrived on Friday evening. Not only did the housekeeper take care of the cleaning, but she also did the laundry, including my laundry.

Because I changed back to Jason before I left on Sunday, I had some of my boys’ clothes in my room. On one Friday afternoon I arrived earlier than usual, and the housekeeper, Mrs. Benson, was still there. Since I was dressed as Jason, she wanted to know who I was.

“Your Aunt didn’t say anything about a Jason, so who are you?” she demanded.

“When I’m here, I’m Margaret,” I replied. “Now I have to change into Margaret,” I added and went up the stairs.

Mrs. Benson followed me upstairs and into my room. “This I’ve got to see,” she said. I couldn’t see any harm in it so I took off the clothes I had worn to school. As was usual, I wore panties under my school clothes, so these stayed on. I put on a bra, pantyhose and a half slip. This I followed with a cream colored blouse and a tan skirt. For footwear, I selected a pair of loafers. I then applied makeup and did my hair up in a feminine style. All the time, Mrs. Benson studied my progress from a teenage boy to a girl.

I must note that Mrs. Benson was in her forties, and rather nice looking.

When I was finished dressing, Mrs. Benson came over and rearranged a stray hair. “Better,” she said, “so tell me, do you like dressing as a girl, or is all of this your Aunt’s idea/”

“I like being a girl. It just so happens that living here allows me to satisfy that desire,” I said.

After Mrs. Benson had left, I asked my Aunt about her. “It seems that she was married some time ago,” my Aunt said, “I’m not sure what happened to Mr. Benson, but he appears to be totally out of the picture at this time. She had great references, and she has made my life a lot better and easier. I really don’t know much about her personal life or what she does on weekends, and I really don’t care. By the way, if she causes you any problems, just tell me and I will take care of them.” I accepted her story at face value at the time, only to find out otherwise a short time later.

One Friday afternoon, I again arrived at the house before Mrs. Benson had left. As before, she followed me to my room to supposedly ‘help me dress.’ While I was standing there wearing only my panties and bra, Mrs. Benson went to the closet and picked out a dark blue dress. “Why don’t you wear this?” she suggested. Since I liked that dress, I had no objection to her suggestion. She stared at my light pink panties and white bra. “You can’t wear those panties and bra with this dress, you need a darker color. I noticed that you have some nice black panties and a black bra. Let me get them for you,” and with that she went over to the dresser.

She handed me the panties and bra ans said, “Here, put these on.” Having lost most of my modesty around other women, I complied with what she said. I sat on the bed to remove my pink panties, and while doing so, I noticed Mrs. Benson staring at my private parts. Although she said nothing, I did hear her making a humming sound, as if a sound of approval.

Before she left, Mrs. Benson told my Aunt that there were some things she hadn’t finished doing, and said that she wanted to come over on Saturday to take care of these loose ends. My Aunt would be at a church function all day on Saturday. “Maybe Margaret could drop you off at the church and then come back to give me a hand,” Mrs. Benson suggested, “there are some things I want to do that are a lot easier if two people do them.”

My Aunt had no objection as long as I was at the church by three o’clock to pick her up. Mrs. Benson assured her that we would be done long before three.

That Saturday I put on a plaid miniskirt, with a pink cashmere sweater over a camisole, and thus clad, took my Aunt to the church. When I returned to the house, Mrs. Benson was already there, wearing a pair of black slacks and a white blouse. I silently wondered if she was wearing black panties and a white bra, given how she had told me to wear dark panties under dark clothes, and a white bra under a white blouse.

We immediately got to work, and by eleven we were finished. “Let me fix us some lunch,” Mrs. Benson suggested. Naturally, this was fine with me. I sat at the kitchen table while Mrs. Benson made a casserole for lunch. “I’ll just pop this in the oven and we can relax until it’s ready,” she said. After the casserole was in the oven she walked behind me and began to massage my shoulders. “We did some heavy lifting today, and this will prevent any cramps in your shoulders,” she said. I just sat back there and enjoyed the massage.

“You’re sixteen, aren’t you?” she asked.

“I turn seventeen on April 20th,” I responded.

“I have seen with my own eyes that you are a boy, yet you like dressing as a girl. In fact, if I didn’t know I would swear that you are a girl. Do you want to become a girl?, she asked.

“I’m not sure,” I answered. “I’ve dressed as a girl since I was seven, but only occasionally. You see, while my Mother doesn’t mind it, my Dad is strongly against it, so I’ve had to hide it from him. If I decided to become a girl, I know that I would disappoint him. I love my Dad, and I’m not sure that I want to do that to him.”

“One thing I’ve learned is to consider my feelings first, and not let another person control my life.” Mrs. Benson said, “Maybe as a teenager, you need parental control, but when you are older and on your own you have to consider your feelings.”

“I really don’t want to make up my mind right now,” I responded.

“I can see that, and I understand. Just remember what I said when you are older,” she said.

“Well, what would you do?” I wanted to know.

“I know what I would do, because I did it,” she replied. You see, I was born a boy. I’m really George Benson. I got married, but my wife hated my cross dressing and she left me. Not long thereafter she was killed in a car crash, and I just sort of adopted her identity. You have to promise that you will keep my secret. I really like this job.” So much for the story that my Aunt had fed me about Mrs. Benson. There just had to be more to this.

“Okay,” I responded. “But how did you get references as a housekeeper?”

“By the old fashioned way, I earned them. You see, I was in my mid twenties when my wife left, and shortly thereafter I had my first job as a housekeeper. Those people didn’t need references, but at each job thereafter I accumulated quite a few references.”

“Did you take hormones or have a sex change?” I asked.

“Hormones, yes, sex change, no.”

“So, if I might ask, you still have a dick?”

“Yes, and it’s functional.”

“That must get in the way of relationships,” I mused.

“Yes and no,” she replied, “there are a fair number of people who like a woman like myself. One final thing before we drop this topic; I’m a member of the Dalton Gender Society, a transgender group, where there are people who are going through or have gone through what you are going through now. If you’d like, I can take you to a meeting sometime.”

“I just might want to do that,” I said.

* * *

My arrangement with Aunt Beth worked out well with me. She had re-taken the driving test and passed, but she still let me have exclusive use of the car, I was able to dress, and life went on. It was mid December when my Aunt talked to me about Christmas. “You Mother has invited me to spend Christmas at your house, which should work out well for both you and me. I’d like to go to the midnight service at my church, and, if you don’t mind, I’d like you there with me as my niece Margaret. All of the ladies at All Saints seem to like you and have asked if you would go with me. Please think about it.”

“Then there is the matter of Christmas presents,” she added. “I’ve enjoyed your time with me, and I’d like to give you some money in appreciation. However, there is more. Mrs. Benson and I agree that you need some new clothes and maybe a new coat. We know that your Dad doesn’t approve, so we were thinking about taking you on a shopping trip before Christmas, and leaving all of the new clothes here. Naturally, there will be other presents for you to open up on Christmas morning, but nothing too girly.”

I was overwhelmed, and gave my Aunt and Mrs. Benson big hugs.

* * *

I didn’t know that shopping for clothes could be so much fun, except for a visit to the corset shop. Frankly, I didn’t know that there were any left in business.

“My I help you ladies?” the clerk asked.

“Yes, my niece has a delayed development, so she needs some help,” my Aunt said.

Mrs. Benson jumped right in. “She needs some padded panty girdles and a corset to bring down her waist. Maybe with bra cups on top for some breast forms.”

What followed was a procession of foundation garments, with my Aunt and Mrs. Benson commenting on each. I did have a little surprise when the clerk and I were in the fitting room. “You’re really a boy, aren’t you?” she asked.

When I blushed she had her answer. “Don’t be offended. A lot of my customers are like you, and I value their business, so I want to do a great job on you, not that you need that much help. By the way, when you walked into my shop I commented to myself that you are a very pretty girl. I was sure that the stop was for one or both of the other ladies. I see now that I was wrong. Those two ladies obviously approve of what you are doing, and I assume that they know that you are a boy.”

“They do, and I am thankful of their approval,” I said.

“By the way, no one mentioned a gaff. Do you know what that is?”

“I’ve heard about them, but I don’t have one,” I responded.

“You should have at least two. I’ll see that you get them.”

When we were finished with the purchases, my Aunt said, “keep that corset on, because we are going to buy you clothes to fit your new shape.” And buy we did. I never had so many clothes.