That Saturday will always be a fond memory. In just one day, my fantasies and dreams merged into reality. Two days before, I was a boy who wore his mother’s lingerie and pretended to be a girl. After that day, I was transforming into a girl. It reached deep inside of me. As I fell asleep that night, wearing a pink nightie, I felt at peace with myself.
When I awoke on Sunday, I lay there. I thought about what had happened. As I did, I felt tingly and my “clit” began to harden. I remembered that mom had said that clits could have erections. I reached down and stroked it, imagining I was a girl masturbating. I soon released a stream of warm juice.
After I ejaculated, I felt confused. “Was that okay?” I thought to myself. I got up and took off the negligee and slipped on a clean pair of panties. I put on one of my new bras. I decided to put on the wig I wore the day before and my robe. I went downstairs and found mom having coffee. “Well, good morning, young lady."
“Good morning, mom. How are you?”
“I’m great. Yesterday was exhilarating and fun. But I was thinking; I hope you don’t think I pushed you into doing anything you didn’t want to.”
“Mom, you didn’t push me into anything. I loved what we did together. I’m just so grateful for your support. I don’t think most moms would support their son wanting to be a girl.”
“I don’t care what most moms would do. I support you, no matter what. To be honest, I'm enjoying having a girl around.” No offense to the son you have been, but I think I prefer you this way.” Mom looked at me and said that I needed to get a new robe. “Something more feminine.”
“We should talk about where you are, and where we go from here,” mom said. “I assume you want to continue being a girl, given that you just got up and already have on your bra and panties.”
“Yes, I do, mom. But can ask you something?”
“Of course sweetie. Anything.”
“When I woke up this morning, I loved being in a pink nightie. I started thinking about yesterday. But as I did, my clitoris got very hard.”
“I think that that is normal honey,” mom replied. “That's going to happen. Did you masturbate?" she asked matter-of-factly.
“I did, mom. I wanted to make it go away. I was confused though. Is this what a girl should do?”
“Girls and boys both masturbate. I understand it is a little different for you, but it's just fine. And you don't want your clit poking out of your panties, so it's the right thing to do.”
“I want to explore my femininity and see where it takes me,” I told her. “I feel like it’s me.”
“Oh yes, dear. I see how it makes you so happy. And I want to help and explore it with you.”
Mom made breakfast and told me to get dressed in the skirt and sweater we had bought. “We’ll talk about what we can do to make you more feminine.”
That excited me. I went back upstairs and put on the sweater and skirt. I applied lipstick and put on the new sandals. When I came down, mom told me she had some ideas she wanted to talk to me about.
“I want you to be able to be yourself whenever you want. So I’m wondering what we do when your dad comes home. I'm not sure he’d understand.”
“I know, mom. I thought about that. I’ll just be Rob when he’s here. As much as I prefer being a girl, I can be a boy if I want to. Anyway, he seems to be traveling more than ever.”
Mom agreed. “He is making really good money, but he’s hardly ever home. He will be back tomorrow for two days and then gone for two weeks. But today I think we should shop some more. There are still things you need. I must admit, it’s really fun having a daughter to shop with.”
“Do you want another makeup lesson?" mom inquired.
“Oh, yes, mom,” I enthusiastically responded.
We went over everything and this time I did more of it myself. I loved putting mascara on my long lashes. I also learned about putting blush on. I still couldn’t get over how I looked.
“Let’s do your nails,” she said excitedly.
Mom got out some red nail polish. First, she used a file to shape them. Then she had me hold my hands out as she adeptly applied the polish.
“Let them dry for a few minutes. Oh, and one other thing. While you don't have much body hair, you should start shaving your legs.”
“Yes, mom, I will.”
She also instructed me on some finer points of being feminine. “You have to remember to keep your shoulders back when you walk. Also, move your arms more daintily.” I practiced a bit and mom told me I was making great progress. “And keep working on your voice and how you speak.”
“You are starting to sound like a girl, even when you’re in boy mode.” Mom giggled like she always did.
“I guess I better watch that,” but then I giggled like a girl.
Mom said she thought I should get some everyday clothes. “You can’t always be wearing pretty dresses. Think about what the girls at school wear and we’ll get things like that.”
“As much as you might like wearing dresses and skirts, girls also wear slacks, Capri pants, and simple shirts. But we’ll make sure it’s all girly stuff.”
After my makeup was done, we left to shop. Mom was happy to help me, and I was happy to be her daughter. It was so much fun trying things on in the stores. No one gave me a second look. We bought a few skirts, tops, some slacks, and a pair of dark pink Capris. We even went to the shoe section and mom introduced me to the same sales lady who had helped me the day before.
She was thrilled. “Oh, my goodness. You are darling.” We purchased a pair of pink gym shoes and told her we’d be back.
Mom insisted on getting me two nightgowns and a satin robe. We also bought two simple non-underwire bras. She explained that these were good for two reasons: to wear under my clothes when I had to be a boy because they wouldn’t show, and to sleep in if I wanted.
“Those are great ideas, mom. I would like to wear a bra to school and to sleep. A bra makes me feel like a girl.”
She thought I should get some pantyhose as well. Again, better to wear it in boy mode.
As we were about to leave, we walked past a jewelry store. “I’ve got an idea. Why don’t you get your ears pierced so you can wear earrings?
“I don’t know, mom,” I responded. “Won’t the pierces show when I’m in boy mode?”
She thought about it but told me she was seeing lots of boys wearing earrings. So off we went. It was quick and painless. We picked out a few pairs of earrings, from simple studs to dangly things. We also picked out a couple of necklaces. It was so much fun being a girl.
Dad was home for a couple of days and while we got along, he seemed distant. We went out to dinner and had a nice time. I did wear a bra and panties under my boy clothes. During dinner, dad told me that mom had suggested I receive a larger allowance. "She said you need nicer clothes for school," he explained. He told me he was going to give me a very nice allowance. Mom winked at me. Of course, he was off on another business trip.
Dad seemed to be gone more and longer. Of course, this allowed me to be the girl I wanted to be. I was dressing almost daily and mom just took it for granted. We’d go shopping together. That was always fun. Over time I developed a full wardrobe. At some point, I realized I owned more feminine clothing than male. 'Why not?'I thought. I preferred it.
One day, mom told me she had a surprise for me.
“Wear a blouse today.”
I was nervous. What was this about and why a blouse? We drove to a small building not far away and we went to an office on the second floor. A small sign said, “Sherry Wehr, Certified Prosthetist.” I had no idea.
When we entered, an attractive woman, probably in her fifties, greeted us. “Hello Elizabeth, and you must be Robin. Welcome. First of all, let me tell you you are a very pretty girl. Your mom has shared your secret with me. But I understand your mom hasn’t told you why you are here.”
I looked at mom and she told me not to worry. Sherry told me that she had dealt with lots of girls like me. “The reason you’re here is so I can fit you with prosthetic breast forms.”
I had read about these and I was immediately excited. Sherry brought out a box and opened it to show me the breast forms. She handed me one. It was amazing. It had the shape of a breast and had a soft feel, much more natural than the stuffed nylons I currently used.
“Let’s get you fitted. Robin, if you don’t mind, take off your blouse.” I did as told. “Oh, that bra is perfect.”
I was wearing a white lace underwire bra. She took out the bunched-up nylons stuffing each cup. Then she carefully slipped a form into each cup. A little adjustment and she said she thought they were perfect.
“Go ahead and feel them.” I did and it was amazing. Sherry told me to walk around the office. They jiggled slightly just like real breasts.
“Oh, mom what a great surprise.” I put on my blouse and looked in the mirror. The forms had nipples that showed subtly through the blouse. I was in heaven.
“Your mom told me that you are usually a girl so you may need a second set. Just let me know.” Sherry told me how to care for them and to feel free to call her with any questions.
“Oh Elizabeth, I almost forgot. I was able to get a few pairs of the special padded gaff panties. Do you want Robin to try one on?”
Mom explained that these were special panties that would hide my male part and give the appearance of a vagina, as well as give me more feminine hips. “Wow” was all I could say.
Sherry handed me a pair and sent me to another room. I took off my pantyhose and my panties. But I wasn’t sure how to put them on. They were very tight and seemed to have a firmer, thicker part in the crotch that looked like a mound with a slit in it.
I opened the door and told Sherry I was having trouble. She asked if she could come in. I said "okay." She came in and looked at my clit. “I have to say, Robin, you are bigger than most girls I see.” She just smiled. She helped me pull up the gaff and to tuck my “clitoris” (as she called it) into it.
“There you go. Look in the mirror.” I did and there was no bulge. Just a mound that looked like what I saw when I saw mom in her panties.
Sherry said, “Can we show your mom?” I nodded yes. She opened the door and asked her to come in. Mom looked at my crotch.
“Oh honey, isn’t that wonderful? It looks like you have a vagina.”
We all giggled. Sherry explained that this particular style had padded hips to give me a more feminine shape. Mom thought they looked great. I got dressed and thanked Sherry.
As we walked to the car I could feel the difference. My breasts jiggled and swayed. “Oh mom, what a wonderful surprise.” I couldn’t believe the difference. I was in heaven.
“Just another step in your feminization,” she said.
I was finishing my junior year in high school and was a top student. Everything came easy, even in the advanced classes. While I went to school as a boy, I almost always wore a bra, panties, and pantyhose now. It allowed me to feel like a girl even though I didn’t look like one. I had a couple of male friends, but we didn’t hang out together much. As. I indicated earlier, the jocks thought we were all gay. Maybe some were. I didn’t think I was because I had no interest in other males while I was in boy mode. However, I did seem to have different feelings when I was dressed. I seems to enjoy guys looking at me when I went to the mall with mom.
The majority of my friends were girls. They seemed to like me and I related to them. Probably my best friend was Linda. We were in several advanced classes and got along well. She was very attractive and always wore nice outfits and had perfect makeup, which of course I admired. She also had an incredible body and from my experience probably also wore a C-cup bra like me.
We would study together and I would help her. We’d meet at the library a lot. She had a nice boyfriend. Linda told me he didn’t mind her hanging with me because he thought I was gay. I didn’t care. It just made it easier to see her. She was always telling me how smart I was and she was so thankful for my help. We had started a study club that included three girls who were also in our advanced classes - Sharon, Lisa, and Nancy. Some of the guys referred to us as the “girls club.” I didn’t mind.
One day after school, Linda and I met to go over some lessons. We had been going over things for a when she guided me over to an empty corner of the library. Linda asked me if she could ask me something personal.
I said, "Sure! We’re friends.“
“Okay Rob, but please don’t be embarrassed. Are you wearing a bra?” she said with a sly smile on her face.
Oh god, I thought. I’m caught. Before I could say anything, she said, “I noticed when you bent over to pick up a pencil your sweater tightened across your back and, to be honest, I could make out bra straps. Please don’t be embarrassed. I’m not judging you.”