Forced To Be Feminine By My Sister

I grew up with just my mum and my older sister, Amy. My father had run away when I was very young and didn't remember him. We grew up having macho things banned from the house, so no soldiers and army stuff like most little boys.

I wasn't forced to do all girlie things, but when we went shopping, which seemed to be every week, it seemed to be a dash around to get the odd thing for me, before spending hours and hours in clothes shops for my mum and sister. Amy was only two years older than me, but my mum treated her so differently to me. I would spend a long time waiting outside changing rooms while Amy got to try on one dress after the next, different skirts and just all different clothes. Then we'd be off to the women's shops where my mum would do the same, trying on all different sorts of clothes, before browsing so many different types of lingerie and hosiery - tights, pantyhose, stockings. Once upon a time I didn't know what any of these things were; well why would I, as boys didn't wear any of that kind of thing, but of course, now I know them all. From basques, merrywidows, bras, panties, silk and lace, to lace tops, hold-ups, different deniers. I wonder how many other 14 year old boys have such intimate knowledge of women's lingerie and clothing? So I would sit there, watching Mum and Amy go back and forth with all their clothes. Mum would seem to be buying her so many clothes than I was ever bought, because, "girls need more clothes than boys, silly! And anyway, boys clothes are so.... yawn," Mum would say to me. Perhaps this was indoctrination of sorts, although I'm not sure either of us realized this at the time.

I only tell you all this to try and explain what happened one summer's day when I was 14. I'm trying to say that this wasn't a one-off thing, but that it had built up for many years. Mum was out shopping with a friend when Amy came bursting into the house from her tennis game. I'd not long come in from tennis too, but had been messing about and hadn't got in the shower yet. Amy jumped in before me, showered, dressed and was out again, shouting goodbye as she went out the door, before I'd even got round to going to the bathroom.

Anyway, I ******** and walked to the bathroom naked, as there was no one else about. I couldn't help but notice that Amy must have undressed in a hurry, as her white panties and bra were strewn across the bathroom floor, and her sleeveless tennis top and pleated white skirt were abandoned too. I closed the door and looked at the items on the floor. I could even remember when Mum had bought the top and skirt for Amy, as I'd sat there whilst she had tried on three different tennis skirts; this pleated one, a straight one, and one with a flat front panel with one pleat at either side. The thought had crossed my mind, questioning why I could remember them in such detail and also that I could remember subconsciously approving of the pleated one that Amy had eventually chosen. Almost without thinking, I picked up the skirt and passed it around my slim waist, fastening it at the side. Looking at myself in the mirror, it looked silly on its own, so I made the decision to put on the top too, but as I reached for it, I saw her underwear too and before I knew it, I'd slipped on her bra and panties and was sliding on her top over my head. As I teased it into placed and took another look at myself in the mirror, I was shocked at how feminine it made me look. I had what could only be described as a 'mop' of longish blonde hair and as I teased it into a less boyish style, a strange butterfly sensation hit my tummy and I blushed bright red. I took off all of Amy's clothes, threw them back on the floor and jumped in the shower.

Halfway through my hot shower, the bathroom door burst open. "Sorreee Rich, I promise I'm not looking, but Mum will kill me if I left my tennis gear...." Amy stopped in mid-sentence. "Hey I didn't leave it like that! I know I didn't. Have you moved it?" she asked, now looking up at me, standing behind the glass screen, covering my privates, blushing profusely.

"Hey, get out Amy," I shouted. "I will when you answer my question, brother dear," she answered.

I stood there trying to formulate a reply, but the delay was too long. "Oh my god, you've worn them," Amy gasped, her hand reaching up and covering her gaping open mouth. "I'll wait for you outside Rich. Come and see me in my room." It was definitely more of an order than a request.

Amy's room was directly down the hall from the bathroom and as I peeked out of the bathroom door, I knew I couldn't make it to my room without her seeing me naked. 'Damn her for taking the last fresh towel this morning,' I thought. Amy realised my predicament and called out, "If there are no towels, put on my tennis outfit - ALL of it." Again, there was no wriggle room in her demand. It was so embarrassing as I walked towards where she was sitting on her bed, waiting for me. She patted the bed next to her and as I sat, I subconsciously smoothed down the pleated skirt under my bottom, a point that did not go unnoticed by by sister. There we were, brother and sister, sitting on the pink duvet, both in short skirts and sleeveless tops, albeit Amy's were more suited to going into town and mine for the tennis court. After a good minute looking at me up and down Amy said, "You look cute Rach." I opened my mouth to correct her, but she put a finger to my mouth. "I think Rach suits you better dressed like that, don't you?" I knew it wasn't really a question, so stayed quiet.

I don't know how much else to tell you really. That wasn't the last time that I was dressed as a girl in front of my sister, a fact she insisted upon. For a good while, she only dressed me up when Mum was out. She would dress me in a variety of her clothes, but only ever that first pair of panties and bra. They became mine, albeit stored in Amy's underwear drawer. After a while, Amy would sometimes make me wear the panties and bra when Mum was in and it was a challenge not to let them show. Mum would sometimes shake her head when I'd walk in to the kitchen wearing a thick sweater on what was not a particularly cold day. Thank goodness it was only Amy I 'had' to dress in front of.

Now when we went shopping, I have to be honest, that I did pay more attention to the clothes and lingerie that Mum and Amy tried on and bought. Sometimes I would imagine how some of them would look on me and occasionally Amy would catch me staring and I would blush bright red and look away. I didn't really understand it, but I knew I had grown to love wearing Amy's clothes, although I never said that to her, of course. I wondered if she secretly knew.

One day when we all returned from the mall (with my one new t-shirt and their bags and bags of clothes), Mum was unpacking some of the bags with Amy, when she passed two to me and asked me if I could help unpack them too. It was an odd request, but they had so many to get out, that I complied without a word. In the first bag was a lovely baby pink lingerie set, with two pairs of silky panties, a bra and garter belt, together with several pairs of stockings and pantyhose. I blushed as I took out the soft garments and placed them hastily on the side. What I didn't realise was that Mum and Amy were looking at me out of the corners of their eyes, smiling gently. The second, larger, bag had two skirts, one a short, pleated mini kilt, the second a light, airy polka dot one; light beige with large white spots, plus what I think is described as a 'skater' dress in black, with 3/4 sleeves and ballet wrap around the bust area. There were also a couple of pretty tops in the bag too. I secretly thought how lucky Amy was, until I looked up and saw both Amy and Mum looking straight at me. Mum was holding out a pair of black, patent Mary Jane strappy shoes with a 1" kitten heel. "I think these might go with one or more of those Rachel," Mum said, smiling kindly. Of course, I blushed madly and began to cry. She came over to me and was joined by Amy as they both gave me a big hug. I was so happy.
AnnaliseB AnnaliseB
31-35, T
26 Responses Sep 21, 2012

freeking hot!!! and lucky

Oh my God it is such a touching and...exciting story! You are blessed to have such a family! :-)

My name is Anna. I'm 28 now. My younger bro/sister is 26. This all started when I was 12 and he was 10. Our father had molested me since I was 8. So I I a revenge. 1 morning i found that my younger brother has an erection and doesn't know what to do with it. So I wanked him. I told him that i can help him with that but all summer he must spend in my old clothes as my younger sister. He didn't want to agree but I sucked his little dickie to the edge of ******* and then stopped so he would promise me everything just to continue. We told our parents that we took a deal that if he won't have all "A" degree at the end of school year hell spend all holidays as a girl. Parents agreed and i knew he won't because my bro was only a satisfactory student. So when we got home from the last day celebration, he had to wear my old skirt, with panties, bra, etc. He had hard-on almost always. I used to ********** him, suck or anal play with him. He begged me for my **** but i didn't want without a gum. Mum agreed that we could take a trip to a Girl Scout Camp. She also agreed that i could punish my bro for everything in the way i waned. I loved to cbt him. Offcourse I didn't know what cbt mean that time. I loved to humiliate him, to squeeze or kick or punch his ballsack. He cried and screened so sweet. I liked to make him ****** 10-20times in a row so he begged to sop;). I loved to push a different objects inside his utherus so he couldn't pee without pain. When we were back home i showed our father that his son turned into a girl with a girly feminine voice. After i pleased dad orally i made him **** my bro in ***. Oh, he cried so much:-P. I was so happy. Don't know why but i was. After vacations I made him wear my clothes every weekend and holiday. Yes I still pleased him as promised but don't know if he was happy about that. Every summer he was a girl now. When I got bf I told him he can use my bro/sisster every time I won't be able to please his needs. When my bro turned 18 dad boughed him a breast surgery. Parents died in a car accident 6months ago. So now my sissy brother is my personal slave. He earns money for me as my **** every evening . But best money he earns at Friday and Saturday nights. I love to whip him after he gets home from his work. I'll auction him when I'll get bored with him. Still making him **** but punishing for every ***** drop:P. He **** a lot when I squeeze his balls. Want to know how to castrate him to do that to his balls. But want to do that with no anesthetics. :-P

I wish I would of been your broher.My brother forced me and I secretly loved it.It did not last for very long and I did not get permission to always wear women's clothes.
I would of loved to have been your slave.I am a real sex **** and I would of served all you wishes glady.
Louise CD

sweet story, i'd have loved to have an understanding, encouraging mom and sis like that.

So nice to hear such a great true story.As Crossdressers we are very emotionnal girls.We have the emotions and feelings of girl and truly want to be accepted as girl.
Love you girl
Louise CD

wow thats a awsum story they realy loved u so much!

Luv your story! It's sad all of us couldn't have been treated this way !!

You were truly fortunate to have a sister and mother who helped you emerge from your cocoon. What a wonderful story.

Wonderful uplifting story, thanks for sharing XX

I would so gladly let your sister make me wear all girly clothing and make me total girly including makeup and nail polish...:)

She's a bit older now, but I could ask the question ;)

I know that I would totally cave in and melt right before her...:)

Beautiful story Annalise *sigh*

That is the most wonderful story. I lover hearing that more and more people like us have been accepted fully and lovingly by those closest to us. I have that kind of acceptance from wife and I am pretty sure at least my one daughter realizes and she doesn't have any problem with it. The other one is young enough that she doesn't care yet. She just loves her daddy.

How nice to have a sister and Mum who were so understanding and supportive to an emerging sister and daughter! You had to be in heaven when you realized all of that was for you.

I was Kim, yes.


Such a wonderful story! I had a sister to dress with and loved it.

never had a sister but when I was 9 my mother in the early morn about 8 would dress me in her panties and nighty and have me go to bed with her.Nothing ever happened but she let me see her ***** when she got into bed.I was her little girl and always played house and she gave me a doll which I still had when I went in the army.Still wear panties 24/7 365 and a nighty to bed. Since then I have had quite a few lovers that spread my cheeks and made their woman.I loved it and still do.Thanks mom for giving me the nudge to be my feminine self.

well my sister dressed me for a contest which i won a first place but i was to young to under stand now know why i dress now

Fabulous sweetie

Yes I'm jealous also never had any sisters sometimes wish i did instead of slightly older girl neighbours.

what a wonderful story. your mom and sister were so nice to you

Great story, lucky you were to have such sister and mum

What a great story! I'm so jealous of those of you with older sisters that were accepting of their brother and their crossdressing. And then when mom gets onboard, what more could a gurl possibly want? Loved the story. Would love to hear more about them dressing you!

Nice story

How I would love for that to happen with me, my daughter and adult grand daughter!
I never had a sister..............

Good story on the basis of getting girly.

It' a nice story of being introduced to wear girl-clothes for your Mum and sis.