Being Sister's Dolly

Growing up, my sister always sewed all the clothes she had for her dolls. My sister Diane is a year and a half older than me. I have always looked up to her and done whatever she asked me to do. My name is Troy and Diane always liked to dress me as her "Dolly" and it is where my love of wearing pretty girl's lingerie began.

I was about five months past my 18^th birthday when Diane asked me if I would be comfortable taking off all my clothes while she took my measurements so she could sew up a complete wardrobe of lingerie and pretty nighties for me. We were both still living at home and she said if I agreed, we could do it when our parents were out of the house. My sister had seen me naked many times, but the least amount of clothing I had seen her in was just her bra and panties.

"You want to sew lingerie for me?" I asked.

"I do. I can use it as a project in my college sewing class and you and I can use it to have a little fun." Said Diane.

"I guess it would be okay. You know how tiny my penis is; wearing panties would probably be more comfortable for me." I replied.

"I know it will. I'll make you several pairs and they will be really pretty and sexy. You're going to love them." Smiled Diane.

It was just a few days later that Diane and I found ourselves alone in the house as both our parents were out.

"Dad's at work and Mom won't be back for a couple of hours. Now is a good time for me to get your measurements. Come here into my room." Said Diane.

I had my shorts and a T-shirt on as I entered her room. Diane was in just her bra and panties.

"Okay, take off those clothes and let me get your measurements." She said excitedly.

I unzipped my shorts and stepped out of them then I pulled off my T-shirt and lastly I pulled down my jockey underwear. My penis was fully limp and barely stuck out from my body.

"Oh, your little penis is so tiny and cute!" Said Diane smiling.

"It has always been this small. I suppose I'm much more like a girl than I am a boy." I sighed.

Our parents had spent a lot of money to send Diane to an all-girls school and me to an all-boys school. Neither of us had any kind of experience with the opposite sex. I knew for a fact that Diane was a virgin at 20 years old and I was most definitely a virgin at 18 and a half years old.

"Does your penis ever get bigger when you are excited?" Asked Diane.

"Sometimes, but usually not." I answered.

"And what about the small amount of pubic hair? At your age you should have a lot more." Said Diane touching my penis and pushing it from side to side.

"It has just never grown in. What about you? Do you have a lot of hair between your legs?" I asked.

"Well, I'm not going to show you, but what I do have I'm going to shave off completely so I'm nice and clean down there. You need to do the same thing, and while you're at it, shave your chest and legs too, it will make the panties and slips I'm going to sew for you feel so good when you slide them on." Directed Diane.

My little penis did not get the least bit hard nor did it even feel plump as my sister took my body measurements. She touched my penis several times and I enjoyed looking at her in just her bra and panties. My nipples really engorged themselves however and grew to a rather large size.

"Look how big your nipples are getting! That's what happens to me when I get turned on. You have a lot of traits that women have, don't you think?" Said Diane.

"I guess so. I've never been with a girl before in a sexual way." I replied.

"And I've never been with a boy before in a sexual way, but that doesn't mean we both don't get turned on now and then." Smiled Diane.

What I did not know was that Diane had been planning a girl's sleep over in a few months when our parents were going to be gone for a 3 day weekend. She had gotten approval from our Mom for the sleep over and her plan was to have me model the lingerie she was sewing for me in front of her girlfriends.

"Before Mom or Dad get home, why don't you let me help you shave off your body hair? You're naked now anyway, I'll get a razor and we'll shave you smooth." Said Diane with glee.

Before I could really object Diane had me lying naked on her bed on a large towel. She spread ladies shaving cream over a small area on my chest and also covered my legs, and then she put lots of lather between my legs. Thankfully I had no hint at all of an erection. Quickly she began to shave off all my body hair until there was none left at all anywhere on my body. She quickly applied baby oil to avoid any razor burn and my skin felt very smooth and soft.

"Let's go get a pair of Mom's panties so you can try them on and feel the difference." Said Diane as she went into our parent's room and came back with a full cut pink and lace pair.

"Here, try these on and tell me how they feel." She said as she thrust the panties toward me.

"Won't Mom know?" I said a little nervous.

"Not if you don't leave them on so long. Just try them for the feeling and let me know how you like them. Besides, when I put them back you'll have the fun of knowing Mom will be wearing panties against her pussy lips that you had your penis in just hours before." Smiled Diane.

The feeling of the nylon and lace panties was wonderful. I loved how my skin felt against them.

"I love how this feels! Are these the kind of panties you're going to sew for me?" I asked.

"Of course, and when we put nylons, a bra, and a slip on you it will feel even better. Now take them off so I can put them back in Mom's lingerie drawer." Directed Diane.

"What about the hair between your legs? Can I watch you shave yourself?" I asked.

"No. I'll shave myself when I'm alone. I don't feel comfortable showing you my pussy lips."

It was about three months later that our parents were going out of town for a three day weekend. My sister Diane had invited three of her girlfriends from her all-girls school to spend the weekend with us. Diane's plan was for her to give me the box of lingerie she had been sewing for me on the first night of the sleep over. She also had some other plans for me.

It was just about an hour after our parents left when the three girls showed up for the sleep over. Amy, Kathy, and Marlene all drove over in the same car. My sister was planning on all the girls sleeping in our family room in the back of the house. I was to stay in my room. My sister had let me know all three of the girls were virgins. Only Kathy had been on a date once with a boy and all they did was French kiss. Kathy did not want her date to touch any other part of her body.

It wasn't until after dinner that my sister called me into the family room where she was with all the girls.

"Troy, come in here, the girls want to see you and say hello." Called Diane to me from the family room.

I was only wearing a t-shirt, jeans, and jockey underpants. I was barefoot. As I walked into the family room all of the girls were wearing baby doll pajamas, each in a different color. They had lots of lace on each one and a couple of the girls had chiffon baby dolls. All of the girls were wearing large bloomer panties as part of the baby dolls. Because the girls were in their early 20's all of their breasts were very perky and there was no hiding the fact that their nipples were erect under their nighties. I could see through a couple of the nighties and had a clear view of the excited girl's breasts.

"Ladies, this is my brother Troy I have told you about, Troy, this is Amy, Kathy, and Marlene." Said my sister introducing her friends.

"Oh, he's cute." Said Amy.

"Yes, where have you been hiding him?" Said Marlene.

"I've been working very hard to prepare him for tonight." Said my sister.

"You ladies are all very beautiful. Diane tells me only one of you has ever been on a date with a boy." I said looking at the girls.

"Yes, that's true, but it doesn't mean we're not curious." Smiled Kathy.

"That's why I called you in here Troy. I told the girls you would not have a problem taking all your clothes off and letting us look you over." Said my sister smiling.

"You mean right here, right now?" I asked.

"Yes, right now. Take off your t-shirt and pants and drop your underwear so I can show the girls what I've been seeing." Directed Diane.

The thought of getting naked in front of the girls was exciting and I did not need to be asked again to do it. I first took off my t-shirt exposing my hairless chest. Then I lowered my jeans and stepped out of them exposing my hairless legs.

"Oh my gosh! You don't have any body hair." Said Marlene.

"Wait 'till you see what I have had him do for me." Said Diane. "Go on Troy, take off your jockey shorts and show the girls."

I did as my sister asked and there was a tiny gasp among the girls.

"He's totally hairless!" Said Amy.

"Isn't that sweet." Said my sister.

As I stepped out of my underwear I was fully nude in front of the girls. What surprised me as the girls looked me over was I did not have any hint of an erection between my hairless legs. My tiny penis was fully limp and slightly pulled back inside my body.

"Oh my God! I've changed a baby boy's diapers when I was babysitting who had a bigger dick than your brother has." Said Kathy.

"I've never seen a naked penis in real life before. I have sisters, and I've never seen my dad without his pants on. But Troy's penis does look kinda small from pictures I've seen." Said Amy.

"How would you ever get something so small into a vagina?" Asked Marlene.

"Well, I have never tried and I don't think I can do it." I replied.

The girls asked me if they could reach out and touch my limp little penis and I told them they could. It was interesting for me to watch their reaction to touching and lifting up my little cock. At no time during this did I have even the slightest urge between my legs or even the faint sensation of becoming hard. I remained completely non-sexual through the entire time.

"Go on Troy, tell them what you really feel is going on down there between your legs." Said my sister.

I looked down and said; "I think I would much rather be a girl. I've never been on a date with a girl, I can only remember having an erection a couple of times, and I really enjoy wearing my sister's and my mother's panties and slips. When Diane asked me to shave off my body hair and then try on a pair of panties, it felt so natural and normal for me it made me wonder why I have a penis between my legs at all." There, I had said it.

"That's what I have planned for us tonight ladies; we're going to take my hairless little brother and turn him into my beautiful little sister, and she's going to remain a girl the rest of this long weekend. It's what you want, isn't it Troy?" Asked my sister.

"I'm very ready to be as pretty as you girls are. And I would love for you to tell me how girls dream about being with sexy guys. I want to know what you do to attract men to you. If I can look as pretty as you are then I will naturally want to try to attract a man to me." I smiled.

My sister had me remain naked and sit in a chair in front of a mirror. The girls began to apply make-up to my face giving me a true "girl-next-door" look which was what I wanted.

"Ohhhh, Troy, you are looking so pretty and so natural as a girl! It's no wonder your penis is so little, and look, your nipples are getting really big and round. That happens to me when I think sexy thoughts." Said Marlene.

When my sister applied false eyelashes to my eyelids followed by subdued lip gloss in just the right shade, and then slowly pulled a shoulder length wig into place getting the hair to fall perfectly, the girls showed me the mirror and I was stunned! There was no trace of any type of male features. I could not believe my eyes. I looked genuinely female, so much so, that my slightly flat chest looked out of place. I looked much more natural as a girl than I had ever looked as a boy. I knew right then, my desires to experience life as a girl were real.

"Let's put Troy in a pretty baby doll nighty! I brought an extra one and I'm sure it will look great on her." Said Amy.

It was a very feminine pink baby doll nighty with chiffon over nylon and lots of lace. Big bloomer panties had lace around the leg openings. When they helped me into the baby doll I looked exactly like one of the girls.

"My goodness, you are so naturally pretty!" Said my sister. "Now it's time for you to get ready for bed."

My sister had me remove all of the make-up except for the false eyelashes and lip gloss. The girls walked with me into my bedroom and helped me into bed, then I was told to get a good night's sleep as in the morning they were going to fully dress me and we were all going shopping.

I had never slept as soundly as I did that night in my pretty baby doll nighty. At no time during the night did I have any hint of an involuntary erection and when my sister came into my room in the morning, my little penis was pulled back almost completely into my body.

"Wake up Troy honey. We want to get you showered and dressed." Said my sister.

The girls watched me take off my nighty and they told me to keep my wig on as they gave me a shower cap to put over my hair. I was given delicate soap to use that had just a hint of a sweet smell to it. As I got out of the shower the girls helped me dry off, again touching my tiny cock, but it had no reaction.

"Come over here Troy, I want you to wear the lingerie I made for you and top it off with a pretty dress today. We're going to take you out with us." Said my sister.

After I took of my shower cap the girls reapplied my make-up. Then my sister went to the box and pulled out a satin and lace, six strap garter belt. She had me step into it and pull it into position. Next I was told to sit down and long, lace top white stockings were handed to me and I pulled them slowly up to the clasps on the garter belt. With both stockings in place and tightly attached to my garter belt I was told to stand up and given a pair of nylon and lace full cut panties. I pulled them on over my stockings and garter belt. Again, my tiny penis pulled itself back inside my body. My panties had a perfectly flat front to them.

"You are going to make a very pretty girl, Troy." Said my sister.

Next my sister gave me a satin and lace white bra that had cups much larger than my flat chest. She followed this with two teardrop shaped breast forms and told me to put on the bra and insert the breast forms. The weight of the forms gave me my first feeling of having female sized breasts. The feeling was very natural for me almost at once. Next, I was handed a pink petticoat and told to pull it up to my waist. Then I was given a nylon and lace camisole that was also a matching shade of pink. With both of these items in place I looked like a princess. There was zero trace of anything male in my appearance.

"Sweetheart you are beautiful!" Said the girls who were still in their baby doll pajamas from the night before. I asked if I could watch them dress for the day and was told very quickly that I would not be allowed to watch them as they changed into their daytime dresses. I was told to go to my room and wait for them to come get me and give me the dress they had planned for me to wear that day.

As I sat alone in my room dressed in the beautiful lingerie my sister had given me I felt sexually excited deep inside my body and was relieved that none of my sexy thoughts were male induced in any way. My tiny penis was fully contracted into my body and not at all plump. My nipples were big and getting bigger under the breast forms in my bra. I truly felt as if I were another person; a very female person; and I loved the feeling of being a girl.

"Come on Troy, we're ready to go out now." Said my sister as she poked her head into my room.

All of the girls looked very pretty in their dresses and I fit right in wearing my dress and full make-up. We drove to a local shopping mall and the plan was to walk around and shop and have lunch at a restaurant in the mall. I was instructed if I needed to use the bathroom to use only the women's room and act very natural.

As we walked around the mall as a group of girls we attracted the attention of more than one male and I got a bit of a thrill as I saw men looking me up and down and smiling in my direction. The other girls openly flirted with guys they thought were cute and I just smiled back at men who smiled at me.

At lunchtime we went into a restaurant and we were seated in a booth. A few of the guys who had seen us shopping came into the restaurant and made a beeline for our table to start a conversation.

"Well hello Diane, who is your gorgeous friend you have here?" Said a guy to my sister as he looked in my direction. I felt a bit like his gaze was undressing me and I liked the feeling.

"Hi Jake...This is my cousin Troy, she's visiting from out of town." Answered my sister.

"Hello Troy." Said Jake as he slid into our booth right next to me. Our legs touched and I felt a shot of adrenaline go through my body.

"Nice to meet you Jake." I replied in a higher than normal voice.

"It's really nice to meet you baby, I don't mind telling you, you are one good looking babe, and you are making me hot." Said Jake with a sly smile on his face.

I was stunned at his forwardness and I could clearly see he was building an erection in his pants as he slowly spread his legs open in the booth.

"Alright Jake, that's enough, let Troy alone, she's only here for the weekend and we want to get our lunch without your naughty comments." Said my sister in my defense.

"It's cool baby, I'm just admiring the goods that's all." Said Jake as he got up from the booth with no desire to hide the fact he had a hard-on in his pants.

"Beat it Jake, it's a girl's day out and you're not invited." Said Amy.

The very idea that a boy could get an erection just by looking at me I found really exciting. Knowing I had on a full outfit of very feminine lingerie under my dress made me want to see where things could go with this boy as I wanted to show him my sexy outfit. But, it was not to be this afternoon as the girls and I went back to our house for the rest of the weekend.

When we got back to the house all of the girls and I spent the rest of the day talking about the boys we saw at the mall and who we thought was handsome and who was not. I stayed fully clothed in my dress as we sat around and talked and I was especially happy with the fact I had no sexual thoughts as a male. I only had sexual thoughts as a female. I experienced no physical sexual sensations as a male as my tiny penis remained flaccid in my panties and barely poking out of my body. My nipples, on the other hand, grew larger and larger under my breast forms the more the girls and I talked about what we would like to do with the boys.

It was my second full day dressed completely as a girl and it felt so normal and natural I was dreading the thought of having to put male clothing back on. I began thinking about ways I could continue to at least wear panties, bra, and slip under my male clothes when my parents returned. But that was in the future and right now it was time for all of us to go to bed.

My sister, Diane, came to me and gave me a long light blue nightgown with a beautiful lace hem and lace around the breast area. It was long sleeved and came with a chiffon see through robe over it.

"Here Troy honey. I want you to sleep in this tonight. Think of it as a wedding night gown. You can pretend you're dressing for bed with your man." Smiled Diane as she handed it to me.

"Thanks, it's really pretty. This may sound like a silly question, but do I keep my bra and panties on underneath it when I'm in bed?" I asked.

"Oh no baby. Take off all your clothes. You'll be totally naked under your pretty nightgown." Said Diane.