(A word from Rita: This is Monica's story. From stories she told me about her growing up I decided to piece together as much as I could in a coherent fashion. She will be speaking in the first person. Enjoy and please comment! Kisses......Rita!)
I was an only child. Maybe things would have worked out different for me had I other siblings especially an older brother. I did, however, have really great parents. Both of them were born and grew up near the Italian Alps. My father is a sweetheart and very loving. There was nothing he wouldn't do for me. Especially after my mother died. I was eight years old when it happened. She was working somewhere in France when the accident happened. She was a part time model and had been doing a photo layout for some French fashion magazine when the car she was riding in was hit by a truck. We were devastated. She was a very beautiful woman and a very loving mother. My memories of her are all good. She was the most feminine person I ever met. She always dressed in the height of fashion and would never dream of being seen without her hair done just so and her face perfectly made up. Growing up I remember she had her own dressing room apart from the bedroom she shared with my father. I often kept her company while she dressed or applied her makeup. She would often let me into her things so I could play at dressup games. As a result I became very enamoured of feminine things. After she left us I refused to let my father touch any of her things. They were my only link to her. I spent much of my free time in that room wearing this or that. Mostly I cried.
My father was away on business a lot when I was young. He spent about two weeks every other month or so in Italy. My grandmother moved in with us so I wouldn't be alone. We call her Nona and she is the head of the family. She's a wonderful person and knows everything about Italian culture including food. She had opened her first restaurant when she was barely in her twenties. For the most part life was good. I had friends in the neighborhood but I mostly associated with the girls. I thought the boys were too rough and dirty. The girls were more interested in the thing I liked to do most. Play dressup! We would spend hours playing with all the costume jewelry my mother had accumulated over the years as well as some of her clothing and makeup. One afternoon my friend Julie came over with her little brother David. She had to take care of him that day because all the schools were closed for some reason and her parents were both at work. I didn't mind. He was a nice boy. We played some board games for a bit and Julie suggested playing dressup. I told her that boys were not allowed in the dressing room. She told me that David would behave so I reluctantly gave in and we went up to play. We did the usual things with various hats, scarves and jewelery. David just sat quietly on a settee' as we did our thing. Julie took an oversize faux pearl necklace and draped it around David's neck. He looked down at it and gave the cutest giggle. In no time at all we ganged up on him and had him wearing various girly things. We put ribbons in his hair, dusted his face with powder and had him wearing a short satin slip over his clothes. We had the greatest time teasing him and dressing him up. It was the most fun we ever had in our dressup games because we both knew we were doing it to a boy! After that we included David in our fun. We told him he was an official girl and named him Deena. He loved playing with us as Deena. It wasn't long before we had him totally dressed in one of my old dresses with a short hair piece we found in my mother's closet. I was loving every minute of it. I realized that under the right conditions that boys could be fun to play with as well. It was the beginning of my obsession with feminine boys. Well, after a few months Julie and David moved away and my fun came to an end but I never forgot about it. I remember watching some sitcom one night when one of the teenage boys had to, for some reason, dress up like a girl. He looked so gorgeous to me. I began getting a weird tingly sensation in the pit of my stomach looking at him. I was attracted to him. I wanted to be with him as long as he looked like a girl. When I played dressup after that I tried pretending that I was a boy dressing up in girly things but it just didn't feel right. I was too much of a girl for it to work. I needed another David to play with but had no idea where to find one. All the other boys I knew would have died rather than wear something pretty. Then one summer the opportunity presented it self.
Although my immediate family is very close I knew very little about my father's sister, Marie. I knew she was married to a doctor and had a son named Larry but that was about it. I remember it was right after school let out that I was told that cousin Larry would be coming to stay with us for a bit while his parents went to Europe. He was a shy boy when we first met and I would normally just take charge on what games we would play or TV shows we would watch. At this time I was also drawing a lot. I would spend hours in the dressing room with my drawing pad and pencils copying pictures from fashion magazines. In most of the pictures I would draw the models with short hair pretending they were really boys all dressed up. Larry once commented on it and I told him flat out that they were boys. They just preferred dresses and high heels to boys clothes. One hot afternoon I decided that we would go swimming in the backyard pool. Larry said he didn't bring anything to swim in so I offered him an old swimsuit of mine to wear. It was a pink and white two piece suit. At first he balked at the idea but after assuring him that no one would see he reluctantly wore it. At first just the bottoms but I dared him to wear the top too, just for fun. He did. After he put it on my brain went into overdrive. It wasn't long before I had him in a matching wrap, sandals and a cute femmy pair of sunglasses. After we both applied a scented sunblock we went out to swim. He looked so adorable in my swim suit! I was getting those tingly feelings again! We swam around and died off in the sun for a few hours having a great time. When we went in to change I was shocked at the tan lines on his smooth chest. "Larry, you have girly tan lines from wearing the top of my swim suit"! He looked in the mirror turning back and forth with a shocked look on his face. We were both soon laughing about it. I decided then and there that the next day I would get him in a dress!
I showed him all around the dressing room. The closets filled with all sorts of dresses and shoes. The drawers filled with lacy, silky lingerie. The vanity covered with cosmetics. I told him about all the time I spent in that room sometimes with friends but more often alone playing my dressup games. He just nodded his head as I spoke. I gave him a sly grin. "Wanna play?", I coyly asked. At first he didn't want to but I reminded him that the day before he was totally dressed like a girl in my swim wear. I heard him softly sigh. "Oh....okay....but don't tell anybody, Monica". I assured him I wouldn't. I began picking out an outfit for him. I decided to dress him in some of my things so the fit would be better. He was very thin in those days and I thought even my things would be to big for him. I selected a dress I wore when I was a flower girl for another cousin's wedding the previous summer. It was a very pretty pink ruffled dress that I just adored wearing. I chose the appropriate lingerie and told him to strip. I let out a giggle when he took his shirt off reveling his girly tan lines! He giggled too! I had him put on a silky pair of panties along with a matching bra that I took delight in hooking for him. Some sheer pantyhose and a long satin slip followed. All the while he remained silent but I could feel him trembling. I had him step into some shoes with only a two inch heel. I told him to walk around to get used to them. I watched with utter delight as he slowly made his way around the room. "Put a little sway in your step, missy!", I told him. Giggling like a little school girl he did just that. He was getting into it! I motioned towards the vanity. "Okay, sit! Let's pretty you up a bit". He looked like a deer caught in the headlights. "You didn't say anything about makeup!", he stammered. I told him I'd use just a little bit and he plopped down on the padded seat. "That's not the way a girl sits down!", I said and proceded to coach him on the fine art of sitting in a dress or skirt. After that I went to work on his face. Just a little powder, eyeshadow, mascara, blusher and lipstick in a soft magenta shade. He looked like a living doll! His hair was short so I fitted him with a shoulder length blond wig. On impulse I spritzed him with a little perfume. He was quiet all during this. I added earrings and a pearl necklace. When he saw himself in the mirror he was silent for a long time. I just sat and stared at him. After what seemed an hour he started turning his head this way and that. His hands spread out his dress. I saw a smile playing on his freshly painted lips. "I look like a real girl", he said in a small voice. His fingers came up to his face as if to confirm the fact that he was really that pretty girl in the mirror. He held his hands in front of him and frowned just for a second. I got up and stood behind him. Putting a hand on his shoulder I asked him if he'd like to have his nails polished to match his lipstick. He looked at me and just nodded. While I shaped and polished his nails I asked him how he felt. "It feels really kind of strange...but it feels nice too", he shyly said. "Would you do it again, Larry?" He frowned at the mention of his name. I quickly jumped in. "Oh, well you really don't look like a Larry in that pretty dress. What should I call you"? He told me he really didn't know as he watched me paint his nails a shimmery magenta. "Well, what women do you admire?", I asked. "I like Madonna", he said with a smile on his lips. For some reason the name Laura came flooding into my mind. The weird thing about it was I heard my mother say the name in my head. "Laura, your name is Laura", I stated, leaving no room for debate. "Laura", he whispered. "Yes....I like that a lot". She became Laura at that very moment as she waited for her nails to dry.
She spent the rest of the day trying on different outfits and was really having a ball. So was I. Nona was out visiting some friends so we had the run of the house. It took some convincing to get Laura to step outside but when she did and felt her first breeze blow up her skirt she was overjoyed! We sat outside sipping lemonade and chatted. "Like being a girl?", I coyly asked her. "I do. I didn't think I would but I love it. Do you think I'm weird"? I told her I didn't think that at all. We talked about a lot of things and she really opened up. I was liking my new girl cousin. As it was starting to get late we realized that all good things have to come to an end. For now anyway. She reluctantly took off her dress and after showering and removing her pretty nail polish she was back looking like Larry again. I never called her that again. She was Laura now and that's the way we both wanted it. She wore panties under her jeans like any girl would. That night as she was getting ready for bed I snuck into her room and handed her a pretty black lacy babydoll nightie to wear. She squealed with delight after she put it on. We sat and talked and I surprised her by giving her a pedicure. She didn't object at all. Actually she giggled wiggling her now bright magenta toenails in the soft light. We both got into bed together and cuddled and talked about all things girly. I gave her a crash course on being a girl that night. She, for her part, asked tons of questions. The rest of her stay was spent as a girl. Even if others were around she'd be decked out in the frilliest of lingerie under her boy things. It was a sad moment when she went home but we talked on the phone every day and saw each other most weekends. I knew she wasn't really happy at home and I also knew she was secretly dressing up and putting on makeup there as well. Eventually she got caught but I'll let Laura tell you about all of that at another time.
I tried liking boys but it didn't give me the satisfaction and inner peace I felt when I had a boy in panties. I tried with some others but it would never work out and some even handled it hostilely. I thought I might be a lesbian and even had a few flings in that direction when I started college. It was fun and I enjoyed it but after losing my virginity I realized that I also liked cock as well. I decided what I really needed to make my life complete was a feminine man who would dress like a woman but still function sexually as a man. I never thought that would happen and then I met Rita working in the library. Well you know how that turned out! We became best of friends and soul mates on an entirely different level. She already had the love of her life and I wouldn't jeopardize that for all the world. I eventually found the perfect person but, if you have been following this saga, you already know that. Well, that's my story.