Every since I was 4 or 5 years old, I can remember being extremely interested in girls’ and womens’ clothes. This interest continued on and off throughout my childhood, and became quite an obsession during my teenage years. At sixteen, a most exciting experience occurred that I shall now recount in detail with help from my diary. During my teenage years, I was raised by my grandmother in a suburban town in upstate New York, about twenty miles north of New York City. My grandmother owned a two-family house and often rented the upstairs apartment to young couples or students. When I was fifteen, two gorgeous young ladies named Linda and Stephanie moved in upstairs. They lead very interesting lives. By day, they sought acting, dancing, or modeling work. By night, they were exotic dancers so they could pay the bills and have some adventure, I first discovered by eavesdropping.
I eagerly became acquainted with Linda and Stephanie by doing chores and running errands for them. These girls were extremely attractive and very much into clothing, cosmetics, and lingerie. They looked stunning in whatever they wore, be it jeans, miniskirts, or evening gowns. Whenever I was in their apartment, whether to water the plants, bring up the mail, or unclog the drain, I couldn’t help but notice an occasional pair of panties, a bra, a G-string, or some nylons lying around. When they were home, they might have caught me staring at such articles on several occasions, although I tried to be as discreet as possible.
After they had been there a few months I turned sixteen. I was finding that constantly daydreaming about them and their underwear was driving me crazy. My desires were overwhelming me. I knew I couldn’t have the girls, but I felt I must at least have their clothing to touch, fondle, and wear like they did. I had never taken anything without permission in my life, but this was more temptation than I could bare. I gave in to my obsession, and decided the only way would be to take their clothes on the sly. (I well knew that I couldn’t just ask them for these personal things, their underwear and such, so I stole them whenever the opportunity arose.) I would help myself to a pair of panties here, a bra and slip there, etc. However, soon this got out of hand, and I started taking more and more of their things. I advanced from panties, bras, and nylons to slips, nightgowns, lipsticks, earrings, some shoes, several skirts and dresses, a bathing suit, etc.
I would get so scared when I would take something that my heart would pound, but after a while the fear seemed to add to the thrill. As a further turn-on, often when I would go upstairs to see the girls, I would wear their panties, bras, and even pantyhose under my clothes in their presence without them knowing it, and I would become extremely aroused. I would then return to my room and masturbate repeatedly. After some months of hoarding their clothes, I developed quite a wardrobe. I had decided the best place to hide the garments was with my assortment of girlie magazines in an old trunk in my closet, with the half-hearted idea of secretly returning the clothes to their rightful owners someday.
I kept a pile of my own old clothes and some sports equipment and such on top of the trunk for concealment as I didn’t have a key for the trunk, and my closet door did not lock. I was concerned about this lack of security, but my magazine collection had gone unnoticed and I really had nowhere else to hide the stuff. I knew my grandmother rarely entered my room, and she didn’t have reason to go in my closet. (Nevertheless, it was a bad hiding place, as I will explain.) I continued taking clothes and accessories whenever possible for some time longer. Then, on several occasions, I was nonchalantly asked by the girls if I had seen certain missing skirts or shoes, etc. I became quite nervous by this, and thought they probably suspect me by now, so I decided I must stop taking their things. I did stop for a short time. However, I suffered “withdrawal pains” from having my supply of fresh clothing cut off, and I resumed my previous ways once I thought their suspicion had waned.
My trunk became filled to capacity, and I began carefully discarding things as I found that to be easier and safer than returning them back upstairs in a used condition. After Christmas, big trouble arose. It seemed that Stephanie asked my grandmother if we had any skis she could borrow because some guys invited Linda and her to go skiing. My grandmother said she wasn’t sure, but thought there might possibly be an old pair in my closet somewhere, and that she would be welcome to use them if she wouldn’t mind looking. Later that day, when I arrived home, my grandmother mentioned that Stephanie had borrowed some old skis that she found in my closet! I almost fainted! However, I wasn’t certain if she had found my cache or not, and I spent the weekend extremely worried about it.
The girls returned a few days later. They mentioned nothing about the trunk, and I certainly wasn’t going to ask if they had discovered it. I thought I noticed an angry tone in their voices at times, but I wasn’t sure. After they had been back for a couple of days and no mention of the trunk was made, I felt better. On that Saturday afternoon, I returned home from swimming practice, and as my grandmother had left for a long-awaited trip to her sister’s house, I went straight to my room to indulge in my “treasure chest.” However, I got the surprise of my life when I opened the door and found Linda and Stephanie sorting out their clothing, shoes, and cosmetics from my trunk which lay open on my bed!
As I stood there in shock, Linda said teasingly, “Oooh, you’re in trouble. You’ve been such a naughty boy.”
Then Stephanie said that she had discovered my trunk when she borrowed the skis but decided to wait until my grandmother was away before confronting me about it. She then said something about this pile of clothes being hers and that pile being Linda’s, and a third pile being made of things they couldn’t identify or that had “dried cum” or something gross on them, so I might as well keep them to go with my magazines. Then Linda giggled and said that she bet she knew what I did with the their clothes. She said that I put them on for their feeling, looked in the mirror, and played with myself. They both thought this was very funny and mocked me. Linda went on to say that one of her friends had dated a guy who did this sort of thing. I stood there sweating, and my heart was beating a mile per second. They said that I’d better not take any more of their stuff or they would tell my grandmother what her “granddaughter” had been doing, and as it was, there was at least two hundred dollars of clothes and stuff missing or ruined, and I would certainly have to pay for them! Trembling nervously, I said I would pay, but I only had the forty dollars my grandmother left me for groceries, and I couldn’t get that much money without a job. They said not to worry, they had a “little job” for me. They told me not to dare go anywhere later, but didn’t elaborate further.
As they were leaving, Stephanie handed me the wrinkled but now neatly-folded, unclaimed pile (mostly lingerie) and laughingly said, “Here honey, be a good girl and put your undies away.”
After they left, I regained control of myself, and my nervousness became increasingly charged with arousal. I put on a remaining pair of pink silk panties, bra, and slip, and masturbated intensely. Afterwards, exhausted, I fell asleep on my bed. Some hours later, I awoke to the sound of the phone ringing. It was Stephanie calling. She said that the bathroom sink was clogged and would I come up right away as it was overflowing. I was still half asleep, but it sounded rather urgent, so I quickly pulled on my pants and shirt over the panties and bra I had fallen asleep in to save time. I added a sweater so the bra wouldn’t show through my shirt, grabbed the plunger and ran up. Upon entering, I saw another beautiful girl in their apartment. Linda and Stephanie lead me straight to the bathroom. All three girls entered with me and they shut the door behind us.
I looked at the sink and asked, “What’s wrong with it? It looks okay.”
Stephanie replied, “Nothing is wrong with it darling, we just said that to get you up here.”
I was puzzled by this and asked, “Why?”
She answered, “Because we are going to do something to you.”
“What?”, I asked, very curiously.
“We have a job for you to do tonight to pay us back, but we need to give you a new look before you can do it,” she said.
I asked her, “What kind of new look”
She said, “Don’t worry, you’ll see when we’re finished.”
I asked, “If it’s a big change please let me know because I kind of like they way I look now.”
She responded with broad grin, “Well, I guess you could say it is quite a big change. But sweetheart, we are going to do it to you whether you like it or not.”
I was taken aback by this, and just looked at them. (The girls were very feminine, but could be very tough when they wanted.)
Then she started laughing and said, “You see, honey, we need to transform you from a sixteen-year-old boy into a sexy young lady so you can go with us tonight!”
Before I could believe my own ears, Linda chimed in, “You weren’t very remorseful earlier about taking our things, so you are going to pay us back, and we’re going to have some fun while we’re at it.”
Looking over at the girl I had never seen before, Stephanie introduced her as “Chrissie” and said that she was a hairdresser and was also a dancer with them at night. She continued that they told her all about me, and that she was very eager to lend a hand.
Chrissie looked at me and said, “So you’re the little panty snatcher I’ve heard so much about. You’re really cute. I’m going to have a great time helping Linda and Stephanie turn you into a beautiful woman.”
I still couldn’t believe my ears! I thought there must be some kind of mistake or something.
“Now take off your clothes and get into the tub”, commanded Linda.
I felt both extreme terror and great excitement simultaneously. I was in a trance, and didn’t move right away. The girls thought I was defying them, so they wrestled me down and started pulling off my clothes. Suddenly, I remembered I was wearing the bra and panties underneath. I struggled, but they were very strong. They got my pants down and saw the panties. I froze and they started laughing hysterically. My sweater and shirt were removed revealing the bra. More laughter followed and they taunted me and remarked that I was, “Really asking for it.” While Chrissie and Stephanie held me, Linda quickly unhooked my bra and pulled down my panties. Stephanie twisted my arm behind my back and she and the other girls guided me into the tub of running water and made me sit down for a fragrant bubble bath.
I was sternly warned that, “We can do this the easy way or the hard way. It’s up to you, baby.”
I whimpered, “Okay, okay. The easy way”, and I knew they were serious about this.
As I sat nervously in the tub, the girls selected some of their toiletries to use on me. While Linda and Stephanie shampooed and conditioned my shoulder-length blond hair, Chrissie washed my face with a creamy cleanser and a washcloth. When finished, the girls rinsed my hair and face with the handshower and let the water drain from the tub. When all the water was gone, the girls noted that even though I had sparse leg hair, it still had to be removed. I meekly asked if I could please wrap a towel around myself, but Linda said don’t worry, they had all seen penises before, although maybe not as small as mine, she chuckled. So I stood up shaking while Stephanie rubbed Noxzema cream over my legs and shaved them with a pink razor. Silky-smooth, totally hairless legs resulted. Then she shaved my underarms as well. It felt very odd having my body shaved like a woman’s. Then Stephanie applied her lady’s deodorant to my bare underarms. It smelled nice, but it burned my shaved armpits. Chrissie giggled that I might look like an innocent little virgin now, but soon they would make me look like a really hot slut! As the girls laughed, I felt shivers going up and down my spine.
The girls said they should first style and set my long blond hair and then dress me so that my hair and makeup wouldn’t get messed up.
“What do you mean by hair and makeup?”, I asked in a very concerned tone of voice.
They all had big grins on their faces, but no one would answer me.
Finally, Stephanie said, “Honey, just relax. You’re in for a very long night. There’s nothing you can do about it, so why ask questions? Just be quiet and do what we tell you, and everything will be a lot easier.”
I felt quite intimidated, and they all laughed at this. As they were about to start on me, I pleaded with them to at least slow down and tell me what they had in mind.
Linda said, “Okay, listen. To get even with you for taking our stuff and to give you a chance to get the money to pay us back, we’re going to take you to where we work tonight so you can fill in for one of the girls who is taking the night off!”
I was shocked and immediately protested that I couldn’t possibly dance in a topless bar as a woman.
They all laughed and Linda said, “The girl I would be filling in for was a cocktail waitress not a dancer, silly and with your pretty face, girlish figure, and high-pitched voice, we’ll do the rest. You won’t have any problems.”
I couldn’t believe what I was hearing and said I didn’t know anything about being a cocktail waitress. They said all I had to do was bring drinks from the bar to tables and act friendly to get a lot of tips. I stammered that I was only sixteen and you had to be eighteen (at the time) to drink or work in a bar in New York City. They said to stop worrying, the makeup would make me look older, and anyway, they were friends with the manager, and if he says anything, Chrissie has an old ID I can use.
Then Stephanie said, “No more questions. Let’s get started.”
Chrissie stated that my long hair needed a lot of work. She toweled it dry, combed it, and cut some areas that were grown out and shaggy. She then carefully trimmed the rest of it, and I realized that she had given me a very feminine, layered cut. I whined that I didn’t want my hair styled like a woman’s, but they just ignored me. Chrissie then rinsed out the loose hairs with the handshower. I thought she was finished, but she said that my newly-styled hair needed to be set, as it was too straight and I would look really great in curls.
Chrissie began by blow drying my hair. As she did this, Linda and Stephanie started filing and painting my toenails with red nail polish! I murmured that I didn’t need that, but no one paid any attention. As the girls continued to work on me, I glanced around the vanity area. Among the numerous personal care items, I noticed an assortment of curlers heating on the counter.
I had a strange feeling they were for me.
Chrissie divided my dry hair into small sections, sprayed each section with setting lotion, twisted and wound each section around a heated pink roller, and secured it in place with a roller clip. I moaned that I didn’t want them to do this, but the girls just laughed at me. As Linda dried my toenail polish with the blowdryer to save time, Chrissie continued until my head was covered in pink rollers. A hair net was then placed over the rollers.
Chrissie said, “We’ll get back to your hair later, darling. Now let’s get you dressed.” with that, Chrissie opened a large garment bag that she had brought with her.
I sat there totally astounded as Chrissie removed a red satin Victorian-style tightlacing corset from her bag!
She saw my stunned expression, and she said, “Yes, it’s for you, honey.”
It had black lace trim, strong black stringing in back, and black garters attached to the bottom. (I had dreamed about such garments, but never imagined I would be made to wear one!) Then she produced black silk stockings with a line going down the back, a very frilly and very short petticoat, a little black silk camisole, a bright red bra with black trim and large cups, and a pair of bright red silk panties with black trim around the waistband and leg openings. From another compartment, she removed a pair of shiny patent leather, four-inch spike heels. Chrissie warned me to be very careful with these things because she borrowed them from her roommate who works at the club. Stephanie and Linda had informed Chrissie that I was a size 8, just like her roommate.