The morning started with an early phone call from my twin sister Jenny. She said she wanted to ask me a favor and if she could come over around noon. “Sure sis, come on over, I’ll make us some lunch and we can catch up.” She had recently returned from a business trip, and I had not seen her in a few weeks. Even though we were close, we didn’t have a lot of opportunities to spend quality time together. Both our jobs were demanding; she a lawyer and me an accountant. Since graduating college two years ago, we spent all our time learning the jobs and building up our reputations.
Jenny was technically older than me, by a whole six minutes. She often called me her younger brother, especially when she wanted to make a point or get me to help her. I knew when she wanted something by her pleasant tone and ‘hey little brother, can you please lend a hand to help out your big sister.” How could I ever refuse her, she was always looking out for me since birth.
Jenny was five feet four inches tall with a slim and lithe body. People always commented on how beautiful she was and she accentuated her femininity by wearing the sexiest of clothes. She loved the latest fashions and was seldom seen out of a pair of heels. She had the attention of every man, but for her, they were always a distraction. She preferred going out with her friends and spending time riding horses on our parent’s ranch just about an hour’s ride north from town.
Jenny arrived as planned and we had a nice lunch together. I said, “Okay, so what’s the favor you need from me.” Jenny paused and responded, “Well, this one’s kind of a big one, and I hope you just hear me out before saying anything.”
“Okay, are you in some trouble or something.”
“Heavens no” she blurted out. “You know I’m always goodie miss two shoes. I just know it’s something you may not want to do and despite me being in a real bind, you’re really my last hope. So, I’m hoping you can find it in your heart to say yes.”
So, there it was, she used that familiar pleading tone, and I knew it would be hard to say no, regardless of how I felt about what she wanted from me.
Jenny started off by saying, “Sarah, my BFF is getting married in one month. She and her sister have been at odds over her choice of whom she’s marrying. Brad’s his name and Megan can’t stand him. Megan thinks the marriage will be doomed from the start and that she needs to reconsider. Especially since she and Brad sprung the decision on everyone last minute.”
“Okay, so what’s the favor, I’m having a hard time seeing what my role in any of this would be.”
“Well, since Megan has pretty much bowed out of the wedding and said she won’t participate, that leaves her short one bridesmaid. She always wanted five bridesmaids in attendance and now she only has four. Brad is pleading with her to get Megan on board as he will have his five best friends as his groom’s men. They both don’t want an uneven number on the wedding party.”
“Again, how do I factor into all of this?”
Jenny looked at me slyly and responded, “Do you remember when we used to play dress-up and how you always let me go as far as I wanted in dollying you all up? If I recall correctly, you told me on several occasions how you enjoyed our play time and that you would never admit that to anyone. Well, this is your chance to play dress-up again and it would be helping Sarah and me out so much. I’d hate for her to cancel her wedding because Megan won’t be there, and I so much want to fulfill her every wish as she made me her maid of honor.”
I thought about what Jenny just asked me. It was a lot and although I did enjoy being made up as a princess when we were younger, I was a young man now. Men don’t play dress-up. And besides, how would I ever pass as a real woman in front of so many people at the wedding? No, I think this was too much of an ask on Jenny’s part.
As if sensing what I was thinking, Jenny said, “Look, Mark, I know this sounds crazy, but I have an idea. Before you say no, why don’t we do a trial run? I can have you come over tomorrow and I can give you a makeover. If after I’m done with your makeover and you aren’t convinced that we could pull this off, I’ll break the news to Sarah. She’ll be disappointed, but that is life, right?”
I thought about what Jenny had just said, what harm would it be for me to see if she could make me into a passable female. After all, I would be helping not only Jenny but more importantly, her BFF and soon husband-to-be.
“Alright,” I said, “I don’t think this will work, but if you are confident in your makeover abilities, I’m willing to give it a try. I do remember the fun we had, and even though I don’t truly understand all the mixed feelings I had, I did enjoy being made up into a pretty girl. I’m surprised we kept our playtime secret from mom and dad.”
“Thank you, little brother, you’re the best. Don’t worry about a thing. Remember, we are twins and you said it yourself, you and I look so much alike, this will be much easier than you think.”
I agreed to go over to Jenny’s place the following afternoon. I couldn’t sleep that night. I kept thinking of all those times I spent in her beautifully decorated room putting on dresses, makeup, and wigs. The repressed memories and pleasant feelings had resurfaced as if the events were just yesterday.
I arrived on time. Jenny was excited, as I was too. She had a huge smile on her face, and she said she had planned out the whole makeover the night before. Jenny was clearly not in the mood for small talk, it was down to business. She told me to follow her upstairs to her bedroom. I could tell she had been busy preparing for my makeover. Lying neatly on her bed were several articles of lingerie. Her vanity had the lamp on, and I noticed a huge assortment of makeup neatly organized across the top. There were several high-end wigs propped up on Styrofoam busts. Along the wall were at least six pairs of high heel shoes of varying height, none less than four inches tall.
Jenny saw my amazement. “So little brother, what do you think, am I not serious about helping Sarah out?”
“Yes, I can clearly see that, but I simply thought we’d just put on some light makeup and maybe a wig or two and see if I looked like a passable woman.”
Jenny frowned, “What, are you kidding me, no way, we must pull out all the stops and go for the finish line with gusto. I want to make sure you are comfortable with giving me your decision. As such, I want to give you an ultimate makeover. Only then will you truly feel comfortable in saying, hopefully, yes.”
I understood what was at stake and decided to give Jenny my full attention and commitment to possibly saying okay to becoming one of Sarah’s bridesmaids. “Okay, I’m all yours, how do you want to get started,” I asked.
Jenny instructed me to strip down naked. To get a true representation of what I could look like as a woman, she had me shave my legs, chest, and underarms. This was a bit much I thought, but she was in charge, and I couldn’t really see the point in arguing as the hair would grow back after the wedding anyway.
After shaving my body, Jenny handed me some floral-scented lotion. I spread it generously over my newly shaved skin, and I must admit, the cool feeling was amazing. Jenny said to put on the lingerie she had selected, which was carefully laid out over her canopy bed. She stepped out of the room as I put on the lace-topped stockings followed by the matching black lace bra. It was a 34B, which clearly indicated Jenny knew my exact sizes. It was obvious she had done some prior planning and shopping.
Jenny told me to put on the satin waist cincher and I followed with the matching satin gaff. She instructed me to route the garters under the gaff. She entered the room and helped secure the garters to the lace and back-seemed stockings. Jenny looked down at my crouch and told me to fix my package, so there would be a totally flat appearance. I tucked my balls and penis backward into the gaff. The effect was immediate, it appeared as if I had a vagina.
Jenny opened a small box on her nightstand and revealed two 34B silicon breast forms. She stepped alongside me and worked one at a time into each of the loose bra cups. I now felt the weight of my new breasts slightly pulling forward on my bra straps. My chest now looked surprisingly feminine and, standing there in full lingerie, I felt a warm and happy sensation throughout my body. Oh my god, what was happening to me! Jenny said we were almost done with the clothing. She had me sit on the edge of her bed. She then selected a four-inch high heel pair of black patent baby-doll pumps with an ankle strap. She secured them to my feet. Not surprisingly, they fit perfectly. Jenny then held my arm, lifted me onto my feet, and helped me walk wobbly to her vanity.
Sitting down, Jenny started working her magic. She laid the foundation, worked eye shadow, eyeliner, and mascara on my eyes, and set everything with powder. She outlined my lips with a dark red pencil and filled them in with a lighter softer color lipstick. Then she applied a generous amount of sparkly strawberry-scented lip gloss. The whole time she was applying makeup, we talked about how we really shared a unique sibling bond that many people couldn’t really appreciate or understand. I totally agreed with her. Here I was, having a total male-to-female makeover with my “older” sister, and felt absolutely no shame. Like during my childhood, I felt happy and enjoyed our special time together.
Once she was satisfied with my makeup, she carefully positioned a long brunette wig with long flowing and soft curls onto my head. As I stared into the mirror, I knew I would say yes to being one of Sarah’s bridesmaids. I was gorgeous. I had very sculptured facial features and with the makeup, I could not be mistaken for anyone other than my twin sister. We were identical in every way, this was totally unbelievable, but really, believable because we were twins.
Jenny asked, “So, what do you think?”
Thinking honestly, I said, “I love it, you did such a wonderful job, Jenny, I think I look like a beautiful Victoria's Secret model. I really think you’ve pulled off the most amazing makeover to date. Without Jenny asking me the big question on her mind, I simply blurted out "My answer is yes. I’ll help you and Sarah.” Jenny squealed in delight, “Thank you so much, Mark.” She then paused and said, “Wait, I can’t call you Mark anymore, especially not the way you are looking now. What name would you like to have for the wedding, what shall I and everyone else call you?” I responded that I always liked the name “Racheal.”
“Okay, so very nice to meet you, Miss Racheal. Since you now want to be one of Sarah’s bridesmaids next month, we have a lot of work to do in training you to walk, talk, and act like a real woman. What do you say, since you are all dolled up, we can take the rest of the day to have you practice walking in your heels and learning a few important things about what it is to be a woman? This way, you’ll not only look like a gorgeous woman but fully "be" a gorgeous woman."
“Yes, that would be great, I willingly replied” Jenny gave me a short-skirted Japanese silk kimono to wear over my lingerie. I spent the rest of the day at her house learning to perfect walking in heels. Jenny fixed us a couple of glasses of wine for dinner. I couldn’t help laughing after seeing my own lipstick left behind on the rim of my glass. It was both sexy and erotic at the same time. After dinner, Jenny had me try on some of her cocktail dresses and skirts, and blouses for fun and I commented on how good they all felt. I wore different shoes for each outfit and Jenny styled my hair differently with each new wig she had me try on.
I was sorry to see the night end as I was having so much fun playing dress-up. Jenny said I should spend the night as it was rather late and she had a spare bedroom. I sadly undressed and placed everything back neatly into a drawer she would now set aside for my new clothes. She handed me a satin and lace pink pantie and negligee set and told me to wear them to bed. She said she thought it best to have me get into a proper woman’s mindset as much as I could before the wedding. She said we would also continue to train me for the next three weeks. She said she would go shopping for a few other items and we would have a few more makeovers to perfect my bridesmaid's look.
I was so very glad I agreed to help Jenny and Sarah out. As I drifted off to sleep, I couldn’t help but think what things would be like after the wedding when I’d have to go back to being Mark. Well, that time was about a month away and I told myself that I would just concentrate on learning to become the best version of Racheal that I could. I looked forward to the work I had to accomplish in the meantime, but I welcomed the challenge. Something new, perhaps long forgotten, had hatched in my psyche today, it scared me a little, but I gave into the opportunity to reexplore those wonderful and pleasurable memories and feelings. No doubt, I was excited and reassured that with Jenny as my teacher, friend, sister, and twin, I was in great hands and well on my way to becoming the woman I had always wanted to be, even for just a short period of time.
