I was raised by a mother who believed strongly in marriages based upon female-led-relationship (FLR) principles and who was also a strong believer in the value of petticoating and feminising growing boys. As a result, my two younger (twin) brothers spent many hours each week in "girl time".
Let me start with Alexander. He has grown into an incredibly polite and thoughtful and obedient and submissive man, fully accepting of female superiority and authority, and of course (given how much time he spent whilst growing up dressed in panties and skirts and blouses), he is also deeply effeminate and sissyish. Soon after graduating from high school, Alexander married a woman about ten years his senior - the daughter of one of my mother's best friends. In fact, it was, in a sense, an "arranged" marriage, because my (now) sister-in-law is herself quite dominant, and was looking to marry a man who would be accepting of the role of sissymaid in their relationship, and so the two mothers thought that they two of them would be a perfect match - as has turned out to be the case.
And that is how Alexander lives now - as his wife's full-time sissymaid. Alexander worships and adores his wife Eleanor, and there is nothing she could ask of him that he wouldn't do. His life is now spent in panties and stockings and lacy sissymaid uniforms, and the better he is able to serve Eleanor's desires, the happier he is and the happier she is. Like my own sweet sissy husband Chrissy, Alexander is kept in chastity by Eleanor (who, of course, feels free to indulge her own sexual desires by dating more masculine men).
Turning now to my other "brother" Samuel - whose life has followed a somewhat different path, and to describe what has become of him, I need to go back to the events of the twins' twelfth birthday.
Even though it was their birthday dinner, the boys still had to help dad with dinner preparations and had to serve the females before they were permitted to sit down. But they both were wearing a particularly nice dress that evening and a new "birthday" apron. Then, after dinner (and after they had done the dishes), it was time for the twins to open their gifts. The twins' gifts were, of course, limited to the kinds of items that would be appropriate for girls their age: makeup items, a couple of new skirts and blouses, and even a poster of their favorite boy band. After the boys had opened those gifts, mom (with a smile on her face) pulled out one final package for each of them to open.
When the boys opened that final gift, they each let out a squeal of delight. The boxes contained - their first bras! For effeminate sissy boys like them, the moment of receiving their first bra is undoubtedly a particularly exciting one and a moment they are likely to remember pretty much forever. Certainly that was the case for Alex and Sam. When they each pulled out the padded training bras that mom had given them, their eyes became as wide as saucers, and (after the initial squeals), they both started thanking mom over and over again. But when Sam asked if they could go put them on right then, mom said no - that she thought they should wait until the next day. Upon hearing that, the boys got a totally crestfallen look, and both of them knelt in front of mom and started begging her for permission to wear their new bras right away. Even dad weighed in on their behalf, pointing out to mom how thrilled they both were with the gift and how excited they were by the idea of being able to wear a bra - beseeching mom to let the boys wear their new gifts.
Usually, mom did not countenance any questioning of her decisions, but in this one instance, I could see that she was pleased with how the boys and dad were reacting, and with a laugh, she changed her mind and said OK. When the boys heard that they couldn't have been more pleased and started thanking mom over and over again as they planted one kiss after another on her high heeled shoes. Mom continued to smile as they did that, and especially now, I can look back on that moment and really appreciate why mom was so pleased - because in many ways that moment really demonstrated how effective mom's petticoating and effeminizing of the boys had been.
The boys went back to their bedroom, and then emerged about five minutes later, having changed into matching outfits consisting of navy blue pleated skirts and tight baby blue v-neck lambswool sweaters that were the perfect kind of top to show off how girlish their bodies now looked with their new bras on. Mom told them how pretty looked they looked, which made the boys beam with pleasure, and for the rest of the evening they were almost obsessed with checking out their appearance in the mirror - and sometimes rubbing their hands across their chests to feel their girlish curvatures.
At the end of the evening, the boys changed into their nighties - but mom let them keep their new bras on too. But then, about an hour after they had turned out their lights, we heard Samuel crying. Mom and I went in to see what was wrong. The poor thing was sobbing and sobbing. Mom sat on his bed and sat him on her lap and gave him a hug and asked what was wrong. What Samuel finally said was - he loved wearing the bra, but was sad because he knew he would never really NEED to wear one. Mom gave him another big hug and a kiss at that point and tried to console him, but Samuel was inconsolable and finally started saying over and over that he wanted to develop like a real girl - that he wanted to BE a girl.
When he said that, mom gave him an especially big hug and kiss and told him that if that was what he really wanted, then that's what would happen! To make a long story short - a decision was made the next day for all of us to move to another nearby town and in our new town, Samuel would live full time as a girl. And over the next few years mom also arranged for Samuel to have the medical treatments necessary for him to develop like a girl and then to have a fully feminized body. And so, today, Samuel is Samantha, and lives happily as a woman.
Thank you for your letter Sandra and how delightful to hear from you and to learn more about your amazing family. This letter is no exception and a wonderful look inside where your mother used her considerable skills to provide the gift of femineity to your brothers, well, new sister, and all turned out beautifully.
The new bras of course would be a perfect gift for young boys well on their way to becoming total sissies, their subservient genuflecting to your mother was obviously gratitude for her very thoughtful gift and being allowed to wear them immediately, another perfect training moment it seems to me.
Thank you so much for sharing, I love how well Alexander turned out, a very special wife to serve, a good friend to your sissy husband I imagine and along with Eleanor, holidays must be especially entertaining. Fascinating to learn that Samuel went on the be fully feminized, a gift your mother must have been overjoyed to provide.