The Making of a Sissy Panty Boy – Part 2

It didn’t take me too long to get to Chicago, as Lake Bluff was only 45 miles away. Since I really had nowhere to go, I thought I’d try to find some of my sister’s (Christine) friends in the neighborhood near the high school she attended. There’s this place called Classic Raceways, an indoor slot car racing facility, where I figured I would most likely find anyone she knew. But I had no idea what was about to happen. When I began to enter the storefront, a girl with short black hair got up and quickly approached me. I couldn’t believe my eyes, it was Christine! She asked me what I was doing there and I told her I had just run away from the orphanage. She told me she had just run away from home two days earlier! How ironic! Here I was running away from the orphanage to go home, and she was running away from that very same home! She never really explained why she had left, but I suspected it had something to do with our father.
We sat down and started talking about where I would be able to live. Her boyfriend (Danny S.) wasn’t around, so she was not able to ask him for any help at that time. She asked a couple other friends, but they all said their parents wouldn’t permit that. She couldn’t come up with any other ideas, and I was too young to be in the raceway after 9pm. She told me to go over to a snack shop down the street a ways, that I might find Danny and his friends there. I didn’t have much time because curfew began at 10, so I ran all the way there. Fortunately, Danny was there. I told him I had run away, and that Chris had said he might have an idea where I could stay. He took me to his house and I slept on the floor, next to his bed, so his parents wouldn’t be able to see me from the doorway. That didn’t work because, the next morning, his mother asked him if I had eaten anything since yesterday. She was such a wonderful Greek woman! She seemed to understand and made sure I had breakfast before we left the house. I cry every time I think about how nice she was. Why couldn’t I have had a mother like that? (Long pause here – it still makes me cry today)
Anyway, that’s where I stayed until Danny found a friend (Jerry, everyone called him Ham because he was a large guy) with his own apartment upstairs from his parents. We always had to be very careful and quiet when we went in, so his folks wouldn’t get suspicious. I became good friends with almost everyone in my sister’s group of friends. While they were in school I would hang around the snack shop where they all hung out. (Great memories of The Cellar!) Things were ok for about a week or so, until the day a juvenile officer came in looking for us. We didn’t know if they were looking for my sister, or me and we didn’t stick around to find out. Chris and I took off out the back door and ran about ten blocks before we slowed down to a walk. We kept walking until we reached Evanston, a suburb on the north end of the city. Chris had a friend who lived a few more blocks into Evanston, so we went there and stayed until it was late. Later that night Danny came by with a car and we went to the apartment where I was staying. The next day Jerry’s mom told him he couldn’t have people spending the night, so we found ourselves back at square one. Chris had been staying at another girl’s house and went back there. Danny’s mom wasn’t going to let me live with them, mainly because Danny’s dad wouldn’t put up with it. With nowhere else to go, I ended up sleeping on the roof of another girl’s parent’s apartment for three nights. Ironically, they lived over a bar that was two blocks from the police station. It rained one night and, of course, I got real wet. After that night Danny made a concerted effort to find an apartment. For the next few days though, I stayed in hallways, back porches, and under stairwells.

Danny, Eddie Pomeroy, Tonianne LaBarbera, and I eventually moved into a one-bedroom apartment together. Tonianne had a brother that died shortly after birth, and she still had his birth certificate. She gave it to me, so I could get a job at the Balaban & Katz movie theatre around the corner from where we lived. On that day I became Michael Anthony LaBarbera, age 15 (I was only 13). Me, Italian? I was able to pull it off after Toni dyed my hair dark brown. I used that name for the entire two years I was a runaway. Two years is a long time for a runaway to go without getting caught by the police or truant officers. In the beginning I worked at the theatre nights, and stayed indoors during the weekdays. Since everyone else had day jobs, it wasn’t long before I began getting bored and lonely. And it wasn’t too long before I found myself playing around with, and wearing, Toni’s panties and other lingerie. I would walk around the apartment wearing her panties while I cleaned the house or watched TV. Although I can’t say for sure how Toni first discovered that I had been into her things, but when she came home early one day, she saw me asleep on the couch wearing a pair of her panties and one of her teddies. At first she was really upset because she knew I had been through her stuff. After she scolded me for getting into her things, she calmed down and told me to take off the teddy, but to keep her panties on. She told me to put on my clothes and come with her to the Salvation Army store a few blocks away, so we could go shopping. It was then that I learned just how mischievous Toni could be.
As Toni and I browsed around the store, she began picking up girl’s clothes and checking to see if she thought they would fit me. She didn’t embarrass me, like Mrs. Sheldon had, but she did buy a lot of little girl’s clothes, with the intent of having me wear them. And as soon as we got back to the apartment she handed me a few articles from the bag, and told me to put them on. She warned me not to tell Eddie or Danny, and told me if I did, she would tell them how she found me asleep on the couch. I guess I was pretty used to being told to put on panties by Mrs. Sheldon, so I was compliant. I did just as she told me. Toni liked to “dress me up” in some pretty frilly girl’s clothing. It was almost as if I was her Barbie doll. Most times it was just a lot of different panties and things, but sometimes she would make wear everything she could think of; panties, bras, slips, stockings, and yes, even dresses! She didn’t do it a lot, but often enough for me not to forget the threat of exposure to the others. Fortunately she never tried taking me outside (except for Halloween once), and she never said anything to anybody. This all ended when Toni found a new boyfriend, and moved in with him. I was sadly disappointed I wouldn’t be subjected to that anymore. However, I did start wearing panties all the time again. I guess I just got used to wearing them so often, it became second nature. But I always made sure Danny and Eddie never saw me in them.
Shortly after Toni moved out, Eddie did also. Because Danny and I couldn’t afford to keep the apartment, we moved into a slummy hotel. I found a new job at Liberty Records Distributing Company about a month later, and Danny and I moved into an apartment just down the street from the hotel. It was a real dump, but it was better than the hotel. We stayed there for about four months, until we found a better place. One of our friends, Regina Scott, moved in with us about two weeks later. She had run away from home because her father was making sexual advances towards her. Reggie was like a big sister to me. She would talk to me about all kinds of different things. Whenever I was sad, she would hug me and sit down next to me, so we could talk. Reggie didn’t work, so she spent most of her time at home, or out running around with some of our friends. One day Reggie decided she was going to do all the laundry. When I came home from work that night, she asked me to join her in the bedroom. She closed the door behind us, went to the closet and brought out the laundry basket that was there. On the top of all the other clothes were all the panties I had been wearing that week! She asked me why I had all those panties, and I just started crying. After she got me to calm down, she told me she didn’t care if I liked to wear girl’s panties, but that she was curious as to why I did. We sat down on the bed and, as I continued to sob, I told her about what had happened at the orphanage. She was so kind and understanding about everything. She told me I needed to be more careful about where I kept my panties, and told me to keep them in her dresser drawer, so no one else would find out. She also said I could wear any of her panties whenever I wanted, but to be careful not to ruin them. Then she promised me she wouldn’t tell anyone, so long as I was careful. Reggie never tried to dress me up, though she did buy me some panties a couple of times when we were out shopping together. I never told her about Toni. They were friends also, and I had promised both of them never to tell anyone.
*** Part 3 next week ***