Dressed For ****** -- Part 1

Being raised by a single mother, my twin sister and I spent a lot of time together. We had few secrets except, for a while, that I was a budding crossdresser. I managed to keep it from her for a while but when we were 13 she began to wonder because of my carelessness in replacing her things that I borrowed. Mother never noticed but then her things really didn't fit as well as Carol's did. And I had a few items of my own snitched from laundry rooms.
One day after school Carol asked me straight away if I'd been rooting through her dresser and closet and I couldn't keep it in any longer. I told her how I was attracted to girls' clothes and girls in general but not in a wholly sexual way but rather that I wanted to be like them and look like them. Surprisingly she understood and said she thought I'd make a pretty girl. We were both slight of build and rather fair and she naturally looked feminine but I did also, to a lesser degree. I told her about the clothes I'd been collecting and took them out of their hiding place for her to see. I had several bras, about half a dozen panties, a few slips, both half and full, two girdles and a number of pairs of stockings, as well as a skirt and a couple of blouses. She was impressed and after checking the time asked if I'd get dressed for her. I was thrilled beyond description and when I removed my shirt and pants she saw I was wearing a pair of panties, white as I recall, and that I had an erection. At thirteen it wasn't that big but all the same it was noticeable and she noticed. I put on a bra and wiggled into a girdle and attached the stockings. She was impressed that i knew how to roll them up onto my legs. I got that from watching our mother get dressed all the time. Then I followed with a half slip and a blouse and the skirt. Carol had a pair of "falsies" for me to slip into the bra and tried fixing my hair but decreed that either it grows a lot more of we'd need a wig. She got a pair of Mother's clip on earrings and tried a little make up which didn't go too well because she wasn't all that astute with it at our young age. She said we'd learn as we went along.
That was the beginning of a lifelong affair that defined who we were and forged a relationship deeper that any married couple could ever envision.
Our mother was a lawyer and being one of the few women in the field back then she put in grueling hours and so we were left on our own much of the time. We were top students and both were ultimately admitted to  great colleges. The time we had to ourselves was put to good use.
Carol was a wonderful mentor and taught me a lot, As she matured from girlhood to womanhood so did I. As she learned, I learned. We shared a lot of "our"  clothes because I was assembling a respectable wardrobe of my own, largely chosen by Carol but our tastes ran along the same lines. Lingerie we generally kept to ourselves except for the occasional slip or stockings being shared. My hair did grow but I still needed a wig and our deftness with makeup made me look exactly like the girl I longed to be. We lived in Manhattan and had access to all NYC had to offer. And everyone will attest to this, there comes a time when girls like us have to step out for the rush it gives. We're drawn to the outside world like lemmings to the sea. When we were not quite sixteen Carol felt I was ready so our baby steps began with quick jaunts around the block after dark. Building confidence we ventured farther and farther until we felt out universe was limitless. Soon the darkness was followed by the light of day and off we went. No one really saw anything but but two attractive teenagers, twins, on the street heading somewhere and like most New Yorkers, they couldn't care less. We were seen but not really looked at.
Mother was spending more and more time away, even taking overnight trips but we covered our tracks sufficiently to give her no pause. Our grades were in the top five percent and she was happy, and if she had the slightest inkling of the sub-rosa life her twins were leading she gave no hint of it. Our forays began including sitting in coffee shops, going to restaurants and movies, riding buses and subways all over town, and strolling the streets of Greenwich Village which in those days was another world. Even shopping presented no problems: We were just a pair of twins with money in their pocket to spend. In no time going into dressing rooms was as natural as sitting to pee.
Carol and I did have our own lives and were not actually joined at the hip. She had her friends and I had mine which also lent the air of normalcy to our formative years.Our sexualities were forming and I became drawn to boys as she sometimes would spend a lot of time with her girlfriends. With me sex came naturally with boys and I had a couple of awkward affairs with schoolmates which involved the usual homosexual activities, which I enjoyed. But at the same time I was noticing Carol as a girl more and more. One afternoon she walked in on me ************ and as she stood there I continued stroking myself to ******. She asked if it felt good and I naturally admitted it did. She came to my bed and took my **** into her hand and squeezed it as she sat down on the edge. I reached up and took her breast in my hand and we kissed. We were seventeen and the die was cast.
. We continued kissing and fondling and my hand found its way from her breast to under her skirt and I began rubbing her. Her hand soon lay atop mine and we both rubbed between her legs furiously until she gave out a moan and her whole body shuddered. We both agreed Mother would be home soon and we'd better get things back to normal. Actually we knew it would be more than a little while but I think we simply needed time to sort things out. She changed out of her school things and I into my accursed male togs and we puttered around the apartment not really knowing what to say to each other.
Mother came home and a light dinner Carol and I prepared was enjoyed while we discussed the events of the day. After dinner she and I repaired to our respective rooms to finish homework or to get ahead on whatever we though would give us a leg up on our peers. Typical nerds. 
The next day walking to school the subject was broached by I forget which of us but it was agreed we both knew of its inevitability and that we both enjoyed it. But, we wholeheartedly agreed, we must be careful: me playing at being a girl and her pretending to have a sister were one thing, but getting involved in an incestuous affair was taking a risk. That afternoon we detoured into Central Park and talked more. To my amazement we both owned up to admitting the feelings we had for each other were far more than on a purely sibling level, and if we took our time we could make it work. That afternoon Carol gave me the first of what seems to have been over the years,a million ********, and I was able to get three fingers far enough into her to produce a mind blowing ******. We were still on vastly uncharted ground and were timid about moving onto more in depth activities but after several days she convinced me to go down on her and I loved it, as did she. It was then that she sheepishly admitted that I wasn't the first: she'd been involved with another girl at camp and was introduced to oral sex then. So I decided, what's good for the goose . . . , and admitted giving and receiving oral sex from a couple of boys as well and being taken anally.
All the while my crossdressing was moving along at full tilt and I was beginning to feel more like a girl than as a boy. About a month later, sometime in December, Mother had to go away for a weekend and we were home alone. Hey, we were 17.  On Friday night we slept in Carol's bed and actually did the deed for the first time, and it was fantastic. Her cherry was long gone, ruptured while riding in the park one Saturday, so that obstacle was a non-issue. We both wore nylon and lace nightgowns and once they were raised what followed was almost as natural as a couple who'd been doing it for years. We each had three ******* and literally passed out afterwards. We awoke early on Saturday and chalked up two more fantastic couplings. Not that it didn't enter our minds, but the matter of her getting pregnant wasn't seriously considered, and after having sex on a regular basis for six months, didn't give it a thought. Turns out, we learned later, Carol couldn't conceive, due to some inherited trait. Mother was vaguely aware but chose to keep it from her until the right moment.
The right moment came when we were 21. Mother was still totally clueless about our, by now, intense affair, and totally wrapped up in her career. We went to college locally and after graduation went onto grad school to which we each got scholarships and life went on. Mother was asked to move to Chicago to open a new office and we stayed behind in the CPW apartment, living virtually as two women, and continuing our studies at the same schools. They were single sex in those days and it killed me to have to attend the male side. UGH! 
Our lives continued to be intertwined for a long time and we cherished every minute of it. Our careers diverged but mine morphed in such a way that much of my work became freelance and home based negating the need to show up at an office but rarely, and I was able to become a 95% woman. 
josilv josilv
5 Responses Sep 25, 2011


Wish I had a sister who would help me crossdress.I would love it

And sister, mother, lover, friend, confidant, and everything rolled into one, as you were to her. It was good you two had each other with mom gone so much, and absorbed in other things. I often look at twins that are fraternal boy-girl and wonder, especially two that are very close.

Fabulous enthralling story josilv. It struck a cord with me because i share openly my cross dressing life with my sister who not only accepts it, but supports it in every way imaginable. We share precious moments together while i am femininely dressed. She is very encouraging and has given me terrific hints and ideas to enhance my femininity. She is a superb role model for femininity and sensuality. We go for outings together discreetly while i am dressed. She has sacrificed much of her life to support me through the years since my cross dressing began. She has been a blessing. So many of our kindred spirits have to confront all cross dressing issues on their own and in isolation. So i am eternally grateful to my sister. Thank you for sharing your fascinating story. Fontana

Lovely. Thanks for sharing. Do you still live together?