Crystal's StorySite

My Mother and her Friend              by: Janet Stickney           


I was in my bedroom trying on the new skirt I had just bought when my brother walked in on me. Since I was wearing panties, pantyhose, a bra and the skirt, I could hardly say that it was a lark. After all, we don’t have any sisters, which meant that I had bought the clothes myself, for me.

"Nice skirt" he said, then, with a smile, he added, "Nice legs too."

He was right on both counts. It was a nice skirt, and I did have nice legs. We were the only ones home at the time, and I now had nothing to lose, so I asked him if he wanted to see the rest. "If it doesn’t take to long, sure." He stood there until I told him I would call him, and as soon as he left I went in the bath and did my makeup, which was just a bit of eyeshadow and some soft brown eyeliner. I already had the foundation on. I slipped on a blouse, tucked it into the skirt and ran a brush through my naturally curly hair, clipped in a barrette, and ran some pink lipstick on my lips just before I went into his room. His first reaction was to stand up, as he would for any woman, then, an unqualified gasp.

Jeff was older than I was, and was on his way to college, and after that, medical school. His aggressive class ‘A’ personality made him it a sure thing as far a medical college went. Myself, I’m 16 and still without a plan for life. I manage to fumble from class to class and get good grades, but a plan, no. Where Jeff is tall, over six foot, I’m 5’7" and weigh a fast 140 after a big meal to his 220. He has clear blue eyes that the girls liked, while mine are kind of a washed out brown. He was first and got all of the good stuff and I got what was left it seems. He was a very manly man, and I liked to dress as a girl, but not once in all of my life had he ever talked down to me about my dressing. He didn’t talk it up, and he never once asked me to do it. He merely accepted it.

"Does mom know?"

"I do all of my own laundry, so I’ll say no, but…"

"She knows Brian. Has she seen you lately?"

"Not that I know of, or could help!"

"Maybe you should let her see you, like you did for me."

"Maybe" was the best I would do, and turned to walk back to my room so I could change, and saw mom standing there!

"Hello Brenda!"

"Ummm, hi mom." Mom had not seen me dressed in almost three years, and I was sure she was going to go off on me, but she was calm, very calm! "I was just on my way to change."

"You don’t have the time to change Brenda. My date is on his way over right now, so you’ll just have to meet him as you are."


"You’re the one that got all dressed up Brenda." Then she looked me over. "I must say, you look very nice dear. Go put some perfume on and join Jeffrey and I in the familyroom."

That’s where I was when her date arrived. I was introduced as her daughter, then he and mom left. I went back to my room, took a shower and changed.

In the morning nothing at all was said about my being dressed, until Jeff left for work.

"David thinks you’re a doll, and wants to use you in one of his ads.’

"So you didn’t tell him I’m your son?"

"Of course not! He thinks I have a son and a daughter, and he wants my daughter to be in one of his ads, so how could I tell him you’re a boy?"

"What kind of ad?"

"I have no idea, but he asked me if you and I could stop by later today so he can take a few pictures to see how you photograph."

"Great! He thinks I’m a girl, your daughter, and now you want me to continue this charade!"

"Brenda, when you were 7 or 8 and wearing my clothes it was cute. When you were 14 and went out to Halloween, six times that year I might add, it was interesting and I was mildly concerned. Now you’re 16 and certainly know better, and yet there you were last night, all dressed up again. You like to dress as a girl and you and I both know it, and it looks like someone thinks you’re pretty enough to be a model of some kind. You have nothing to lose by going, so go get changed and be ready as soon as you can."

"But I haven’t been out of the house since I was 14!"

"Then it’s time isn’t it? Mom got that apprehensive look on her face and asked me what I had to wear.

"What I had on last night of course, a denim skirt, and um, a sun dress."

"That won’t do at all! I’ll find something for you to wear. Go get ready."

I quickly went to my room and jumped into the shower, shaving as close as I ever had, and washed my hair, using a conditioner to soften the hair and make it easy to style. Once out of the shower I slipped on some panties and began my makeup. I had my mothers fair skin, so I was able to use a minimum of foundation. I brushed on the translucent powder and waited a minute before I brushed away the excess. A soft green eyeshadow on the very edge of my upper lid, earth tone over that, with a softer plum under the brow, all blended together. On my eyelids I used a deep sable black liquid eyeliner, and under my eye I used a black pencil. On my cheeks I used a peach/rose blend. My hair was shoulder length, and I usually pulled it into a ponytail. Somehow I didn’t think that would get it today, and called for mom. She quickly dragged me to her room and started setting my hair in rollers, using a setting gel. I was under the dryer pretty quickly, and she filed my nails into a nice oval shape and painted them in pink while my hair dried. My hair was dry about the time my nails were, and she handed me a dress.

I went back to my room and slipped on my padded pantybrief and pantyhose, then my bra. My homemade birdseed breastforms, one in each cup gave me a small ‘B’ cup breast. The dress went over my head and as I zipped it up I felt the material closing around me until I managed to get the zipper closed. The dress was a black sheath with a round neck, sleeveless, the hem just above my knees. I went back in mom’s room and she brushed my hair out. When she was done I had a simple pageboy with the ends rolled under. Mom gave me some black earrings which I fastened to my ears, and then a small gold necklace.

"Do your lipstick and so on Brenda, I’ll be ready in a minute."

I used pink lipstick, Obsession perfume, and stepped into my black heels, then dug my black purse out of the closet. I put all of my things in it, including a lipstick and some tissue. Mom was stunning as always, wearing her pink suit with the antique white sheer blouse and gray heels. She looked me over carefully, handed me a red jacket, and announced I was ready, and we drove to the ad agency.

David Manton met us at the door and gave us both a kiss on the cheek. I walked behind them as he led us into the elevator, which took us to the top of the building.

"Mary will show you where to go Brenda, follow her."

Mary smiled and shook my hand, then we went into a studio, all set up for me.

"If they ask you to do anything you don’t want to do, just say so, and they’ll do it another way. Okay?"

"Okay Mary, thanks."

Only once did they ask me to do something that I thought about first, but finally did it. I pulled my dress up so that almost all of my legs showed. When they were done Mary took me to a small coffee room.

"You’re one of the very best boy models I’ve ever seen Brenda." I froze in place, afraid to ask her why she thought I was a boy, and she caught it. "You’re not as graceful as a girl Brenda, that’s how I knew. Other than that you are spectacular!"

"Dave is dating my mother Mary, and he thinks I’m her daughter!"

"It’ll be our secret then, okay?"

I hugged her and we finished our coffee before we rejoined mom and David.

Up to now mom had never said much about my dressing as a girl and I was able to dress, or not, as I pleased. Now, she and I were in the middle of the great lie, and she liked David. If he found out the truth about me it might ruin their relationship, and possibly mine and mom’s. If he decided that I was the girl he wanted, I would be have to be perfect, every time, all of the time, and that would be hard to do. And on top of all of that, I was still in high school! I had this jumble of thoughts running through my mind when he and mom showed up. He put all of the pictures on the table in a fan. I wanted all of them! They were perfect, showing me in the best light, the best poses, and I never looked better.

"You take a marvelous picture Brenda, you’re very photogenic, and pretty!"

Mary pointed to the ones she liked, and he told me that he had to take them to the staff. "If they like them we will probably make you an offer, maybe by the end of the week." All I had off was this week, and then I had to be back in school! "Let us know David, and thank you." He gave me all of the copies on the table as I left.

"This is very bad mother. If they like me, and make me an offer, just how do I manage things after that? I can’t just pop in after school can I? What if they want me to wear a bikini, or hot pants, or show some breast? This can get very messy very quickly mom!"

"David knows you’re a boy Brenda. I had to tell him while you were in the studio. I thought about it and told him."

"What did he say?"

"He was shocked of course, but the humor in it made him laugh, and he said it didn’t matter because you were still a knock out, and wanted you in his next promotion!"

"But what about school? I just can’t quit as Brian one day, and start as Brenda the next; Think of what would happen then? And on top of that I’ll have to manage to be as feminine as possible all of the time, meaning that the way I dress in the ads will certainly demand that I have boobs, and be able to wear whatever is called for! This is going to be very, very hard to do mother, I hope you know that."

"I’m aware of the problems Brenda. First things first however. We’ll wait until we get an answer from David. If they turn you down everything will go on as always and won’t be a problem."

Mom was right, but on the other hand, if they selected me to do this, I would be in deep stuff very quickly! I just wanted to dress up once in a while. Get pretty and maybe go to a costume party once in a while! Now all I could do was wait; I could turn down the offer of course and go on with my life, but the money would be spectacular. All I had to do was become a woman. When I was in my room I touched my birdseed breastforms and started laughing. They gave me the right shape of course, but the only thing that might nibble on them was a bird! I took the dress off and changed into the denim skirt and a blouse and went to the kitchen to get a soda. Mom was there with Jeff, explaining what had happened that morning, and showed him the pictures.

"Hi sis!"

"Hi Jeff" I said and sat at the table, watching his face as he looked at the pictures.

"Pretty good pictures Brenda!"


"Watching you pull this off is going to be interesting, especially when Janice sees you!" Janice was the girl I was currently dating. "I know you’ll disagree, but without prejudice, I think you look better than she does."

"Maybe, but she can wear whatever they want her too, and I can’t!"

"Not yet anyway" mom said, "but…maybe later."

I went back to my room, my own mothers words ringing in my psyche, …"maybe later"…, and I knew exactly what she meant. Making physical changes to my body was never in any plan I ever had, but I will admit that in my dreams I thought about having a female body, what it would be like to have breasts, no penis, and then, periods. In a way I guess I envied women, and wanted to be like them. But, to become a woman? That was entirely different, because it would change everything in my life. My relationship with Jeff, mother, my friends, and of course, the rest of the family. Looking in the mirror I carefully went about defining all of my faults, which was a long list. My beard was fairly light, and I rarely had any shadow at all even though I saved every day. My body hair was thin but existed, and grew quite fast in certain places, like under my arms. I didn’t have any hair on my back…yet, but Jeff does, and I might start growing some any day. My chest was only a bit fleshy and my waist was only an inch smaller than my chest. I did have a ‘cute’ bubble butt according to Janice, which was one of my few pluses. My hair was shoulder length only because I had let it grow out to make it easier for me to become Brenda, but the color, mouse brown, was not at all exciting and I wanted to change it but never had the nerve. I had a small nose, a rounded chin without the cleft Jeff did, my eyes were almost almond shaped and with makeup looked wide set, my general features were neutral as far as gender went I guess. I had inherited a fair complexion from my mother, which had always made it easy for me to use less makeup and look more natural whenever I was dressed as Brenda, but…I was always scared when I was dressed. Scared of the intimidation I might get, scared of being discovered if I went out, unless it was for a party, and scared that someone might find out just how much I liked being dressed as Brenda. Now…

Neither mom nor Jeff said anything that night when I showed up wearing one of mom’s nightgowns. In the morning I changed back to my boy self, half expecting some comment from them, but nothing was said and I called Janice just to talk. That’s when I found out that she had been in an accident the night before, and was in the hospital. I told Jeff and mom, and then drove over to the hospital to see her. It was supposed to be family only, but her mother let me in. Her eyes were closed, with a huge bandage on her head, IV’s stuck into her in several places, three computer monitors were attached and showed her status in a series of lights and graphs. She was unmoving, like a corpse, but breathing. She had a cast on her arm and both legs. Her mother held my arm tightly and started to cry and I found her shoulder and pulled her close to me.

"Her father and brother died Brian, she is all I have left now!" Her sobs wracked her body as I held her, but I had no words to make the pain go away, no magic to make Janice return to the way she was. Only compassion and my own ache for Janice. I liked her, and we were good friends, and seeing her this way drove a stake into my heart. As we stood there all of the monitors started to beep and a bell started ringing. I looked up and saw that the graphs had merged into a single, flat line. Nurses and doctors rushed into the room, pushing us out, and all we could do was watch as they tried to revive her.

The funeral was held three days later. Janice was buried next to her Dad and brother, with her favorite doll in her arms. The sounds of Amazing Grace floated on the wind as her casket was lowered into the ground, the sounds of sobbing punctuated the music as we, her friends and family said our final goodbye’s. With my mother and Jeff, we drove to her house for the wake, my own tears still wetting my cheeks whenever I thought of her. Her mother had gotten over the initial shock, but still held the pain of her loss in her eyes; I hugged her and we cried together, until she asked me to join her on the patio.

"I want you to have Janice’s things Brian, all of them." I looked at her, not understanding what she was telling me. "I’m selling the house and moving closer to my sister Brian; Janice told me about your…hobby. You might find something that will help you, and maybe something that you can keep forever to remember Janice with, like her locket." I had given Janice a locket on her birthday, engraved with her initials. "Come over in a few days and we can sort this all out then Brian."

On the way home the only thing I remembered the statement, "Janice told me about your…hobby", and wondered how Janice knew about it! I had been very careful, yet she knew! I waited a few days and called her, and that night mom and I went over to the house. Boxes were stacked all over the house, a for sale sign in the front yard. She let us in, and as we sat, she looked me right in the eye and told me that she wanted me to take all of Janice’s clothes, jewelry, furniture, shoes, dolls, and so on!

"Just what makes you think that Brian needs all of her things Ruth?"

It was the very same question I had!

"When he and Janice went to that last costume party I didn’t even recognize him Carol! Later, Janice told me that even some of the other kids didn’t recognize him, and two of the other boys had hit on him!" That was true, and something I had not told mom. "She also told me that no boy could look that good unless he really wanted too, and I have to agree. Janice was the only girl in the family, and I have nobody else to give them to Brian. If she was right, then use what you can and give the rest away."

Ruth, Mrs. Whiting, started to cry again and mom took her into the kitchen, leaving me alone, so I went up to Janice’s room.

Her room still held the scent of her perfume in the air, bringing back all sorts of memories. Dolls of all sorts sat on her bed and shelves, her bed was made up in pink and white, and her clothes bulged from her closet. She had a lot of very nice clothes, many of which would fit me, all I had to do was take them. Mom found me there and held my hand.

"You don’t have to take them Brian."

"Yes, I do mother. Even if I give them all away, Ruth needs me to take them, so I will."

Jeff and mom helped, and we packed up the entire room and moved it to our house, and Mrs. Whiting was gone the next day. As I unpacked the clothes, mom put them in the washer to take out the scent of Janice’s perfume, and with Jeff helping, we set up the bed in my room, stashing mine in the basement. It might seem macabre to some, but mom and I talked about it a lot, and I decided that it was just clothing and some furniture, nothing more. Her memory lingered of course, but I forged ahead, and began to try on the clothes, keeping some, and not others. All of her panties, bras and shoes were tossed, yet by the time we were done, I had an impressive wardrobe, everything from skirts and blouses to dresses of all kinds to suits and coats. When I had everything hung up, mom told me that I had a message from David.

They wanted me to do the ads! Now came the decision, the hard one I had to make. I had the will to do it, all of the clothes now, but not the body.

"Ruth said that she knew the first time she saw you Brian. If she did, why not your classmates? After all, some boys hit on you as if you were a girl, right?" I nodded my head yes, and then she dropped a bombshell on me! "Why not just go to school dressed and see what happens? Wear something extra feminine, but be yourself at the same time."

"Because I’ll be killed that’s why!"

"Maybe not. In fact I’ll bet on not!" Then she simply told me to do it. "I’ll help you find something to wear Brenda."

She emphasized ‘Brenda’ as she walked out of the room, leaving no doubt that I was going to school in the morning dressed as a girl. It was my worst nightmare come true. David called and changed all of that! He had enrolled me in a private school for girls, starting the next day!

That night was spent using a hair removal cream, took a bubblebath, and had a careful shaving of my entire body to get the last few hairs that the cream missed. Mom set my hair in rollers, and I did my nails in red. In the morning I got up early and shaved as close as possible, put my makeup on, using subdued colors, and got dressed. What I, not mom, had selected to wear was an all white, lace trimmed blouse with a sheer insert at the neck, a pink and white A Line skirt with gold accents. Clean panties, the padded pantybrief, pantyhose, my white plain Jane bra, and for luck, a waist nipper of Janice’s. The gold and pink belt matched the skirt and set it off nicely, and I wore short white heels with a white handbag. For lipstick I wore a soft red. Mom brushed out my hair, leaving curls down the back pulled away from my face with pink and gold barrettes. My bangs were swept to one side and gave me a peekaboo look with the top high and fluffy.

Mom drove me to the new school and I signed all of the papers.

"We have many girls here, some of them just like you Brenda."

That made me wonder what she meant, then it came to me. I wasn’t the only boy dressing as a girl!

"Besides all of your normal classes, you will, of course, be taking ballet and dance along with a mandatory aerobics class in the morning."

"But…but…I can’t…"

"Yes you can dear. All of the girls take the classes and you will too."

Mom was no help at all! Through her giggles, she said, "I’ll be back to get you at the end of the day Brenda. Have a nice day."

"Thanks mom." We had all stepped into Oz, and there wasn’t any way tornado to get us out, and back home!

Walking into school was easy. Going into my class room was difficult, and I almost ran out of the school, but with the administrator behind me, I went into the room, and knew that no escape possible. Every eye was on me as I walked to my desk and sat down.

"We have a new student this morning, Brenda Grant. Please stand up Brenda."

I did it, and as every eye was on me, the teacher told them that I was a new student, and went on with the lessons. It was like that all day, and by the time I was ready to leave I was exhausted from the tension.

The next day I drove myself to school, armed with a leotard and some dance shoes plus all of my books. I was told by the administrator to see the nurse instead of going to class. Mrs. Holton was an older woman, short, gray hair, and the most massive boobs I had ever seen!

"I was told that you need some special help Brenda, please disrobe and the doctor will see you in a moment."

Her voice was more like a bark, but when she handed me the thin gown and pointed at the booth I went in to change. The doctor, like Mrs. Holton, was older, but he had a crinkled smile that set me at ease right away.

"We have a procedure here that we have developed over a long period, and it’s just what you need Brenda."

He was talking as he examined me, then he asked me how soon my modeling was going to start.

"A month they told me, why?"

"We only need two weeks from start to finish Brenda, please lay back." I never felt the needle slip into my arm.

Over the next two weeks I was transformed into a female, one bit at a time. Each day he did something else, but he started with my voice. Using long thin tools he banded my vocal chords, raising my voice to a higher, more feminine pitch. After that came the laser hair removal, Liposuction to make my waist smaller, small inserts to make my bustline a full, natural looking ‘A’ cup, collagen to make my lips just a bit fuller, and finally, he used the fat from my waist to make my hips rounder, and fuller. By the time he was done I had a 34-22-34 figure. All that remained of my old self was my obvious manhood. That lasted just one more day. When he was done I had what appeared to be a normal, functional, vagina! My testicles had been removed and the sac used to create the labial folds with surgical glue. Then he put me on hormones. It was truly a new sensation to not have something between my legs, but I was able to sit, walk, and look more feminine without it, and I could wear anything. I bought a bikini one day, and waited until Jeff was home and changed into it. When I walked out of my room, he almost choked when he saw me. Nine or so square inches of material doesn’t cover much, and I was swelling out of the top while the cleft of my new sex could clearly be seen.

"Like it?"

My high, soprano voice was still new to him, and he reacted like most men would. He got a hard on! Laughing I went in and slipped on my shorts and a top.

I did the modeling for the ad campaign, then as I took the ballet classes and became more limber and graceful, I also became more aware of the effect I was having on the male members of society. I went on my first date with Hank, one of the boys that had hit on me when I was with Janice. My hormones were raging, just like his were, and I managed to get away with only a grope on the breast, but I knew it wouldn’t be to long before something more happened. I adjusted to my feminine body easily, it was the walking and the mannerisms that were so hard to learn well enough for them to be natural. Ballet gave me limber muscles, some of which I never knew I had, along with a graceful poise. I learned how to do my own hair, what to wear and when, and a myriad of things that girls seemed to learn easily. With no need for makeup, I started to use less, which made me look even more feminine, and with a higher pitch of voice, I was never taken for a male ever again.

The second ad campaign I was in, was, as I had anticipated, set on a beach. I was required to wear a bikini, which they picked out for me. It was during a shoot that Jeff showed up with a friend of his, watching me pose in a variety of sexy ways. He waved as I went to change, and later, introduced me to his friend Steve. I was wearing a pair of slacks and a sweater, something not very sexy, yet all Steve did was smile at me as his eyes roamed over my body.

"We’re going for pizza Brenda, want to go?"

Standing behind Steve a bit, I saw Jeff nod his head yes, so I agreed. "Yes, I’d like that Steve."

I grabbed my purse and went with them, careful to stay close to Jeff. Over pizza, I told them that I had been asked to do a popular swimsuit edition calendar.

"Are you going to do it?" Jeff sounded a bit shaken.

"How can I turn it down? It’s a real kick to get fan mail Jeff! Think of all of the horny men that will see that calendar! It will help my career too."

"I think I’ll be the first one in line to get a copy Brenda!"

The grin on Steve’s face said a lot more than his mouth did, but Jeff stepped in.

"This is my sister Steve, you can look, but no touch! She isn’t 18 yet!"

"Damn!" Steve said, but he was still smiling at me when Jeff took me home.

Mom insisted, so I had to sit through the mother daughter talk.


"I know that you can’t get pregnant Brenda, but there are still a lot of ways to please a man other than that, and I don’t want you to do those either!"


I was embarrassed at how graphic mom got after that. As my mother, I was surprised that she knew all of this stuff!

"Grope all you like Brenda, but no sex!"

"Right mom, no sex."

Being selected as one of the women for this calendar meant that I would be hit on like a drum as soon as it came out, which would present a lot of safety problems. As soon as the site was selected, I was given ten suits to try on, all of them tiny. They said I looked best in white, and became Miss January. The way they posed me left almost nothing to the imagination as almost everything I , had was pushed up, out, or bared to the legal limit. I asked Jeff to be with me, but he had exams, and sent Steve instead. Being close to him every day, almost naked, almost all of the time, gave us both ideas, all of them relating to what mom and I had talked about and she had banned.

At school I was a star, and two of the other girls revealed that were really boys. They did not know about me, they just wanted to tell me that I was what they wanted to become! I graduated in the summer, turned 18, then went to a private clinic to have my surgery, returning a few weeks later. It was a month before I felt like myself again. High on my list was to lose my virginity, to Steven of course, but mom insisted that was not necessary. I had nothing to prove any more. Not to her maybe, but to myself, and I let Steven take me to a motel and remove that ugly stain of virginity. Working as a model now, I no longer worry about discovery. You may even know my real name! It’s….




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