The Confessions of a Sex-Crazy Cross Dresser

Book I: The incredible first few weeks

Chapter 1: Panties Thief and the Late Night Swim

My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used to describe people like me can make you confused. I prefer to be called a cross dresser and yes you can call me Sandy (short for Cassandra) so at least that is not confusing.

There are so many thoughts running through my head as I being this story, I am not sure where to begin…I think I will go back to around 1989. I was in my late 20’s and living in an apartment in Pasadena California. I was single and went out drinking almost every night. My usual hangout was a local bar (“Da’ Place”) about three miles from my apartment. Life was good; I made good money as a salesman, liked to drink, occasionally did drugs (cocaine was my first choice), picked up girls regularly and just enjoyed my party lifestyle.

A standard evening for me was drinking at my local bar and then on my way home (if I didn’t get lucky at the bar), I would look for a hooker in a couple of neighborhoods around my apartment. If I didn’t pick up a girl, or pick up a whore, I would go home and put on a porno and masturbate (I had lots of XXX rated videos). I also had a blow up doll that I would use on occasion, I love getting drunk and “lubing” up a doll and fucking her everywhere (ass, mouth and pussy). If my inflatable whores would break or spring a leak, I would simply buy another doll. Every bachelor should have an inflatable fuck toy.

I always considered myself “straight as an arrow” and I have never really been interested in guys in any sexual way. I have been approached on numerous occasions by gay guys and always said “no”, there was no attraction and I had no desire to be with another man. I was mistaken for being gay sometimes by girls, as I am not the most masculine guy in the world, but I would not call myself feminine. I have a “young” face (especially back then) and kind of a high pitched voice, so that is probably why sometimes this they would make this mistake. Usually when a girl told me she “I thought you were gay when I met you”, she was usually already making out with me or was telling me this after a fuck session.

Going back to `89, I was renting a one bedroom apartment (nothing fancy) in an older three story apartment building complex. It included a laundry room on each floor with one washer and one dryer in each laundry room. One late night, I had fallen asleep on the couch and woke up startled. I realized I had left my laundry in the dryer a few hours earlier, so I strolled down the hall and into the small laundry room on the first floor. Upon arriving I discovered my clothes had been removed from the dryer and placed in my laundry basket that I had left on top of the dryer. Obviously, someone else had needed the dryer, so they had removed my clothes and placed them in my basket. This happened all the time, since there was only one set of machines and people were very courteous.

Upon this occasion, my clothes were neatly put in my basket, which sat immediately next to the other tenant’s empty laundry basket. Since it was past midnight (we were not supposed to run the washer or dryer past 10 PM, as a courtesy for the neighbors), I realized that whoever had done this, probably had fallen asleep and would pick up their clothes in the morning.

As I was getting ready to leave the laundry room, I thought since the person would not be returning soon, I would empty the dryer and put their clothes into their basket. I am not sure if I was doing this to be nice or I wanted to see the clothes in the dryer, but for some reason I wanted to do it. Well, little did I know this decision completely changed my life.

I opened the door and started placing the clothes in the basket; I saw several pairs of women’s panties. There were five or six pair of panties and they were nothing fancy, just a variety of cotton and silk panties. As I finished emptying the dryer, I took a pair of the panties and placed them in my basket, I remember saying to myself “Whoever this girl is, she won’t miss one pair of panties.”

Over the next few weeks, I must have gone to all the laundry rooms in my building twenty times and probably “stole” around fifteen pair of panties. I never took more than one pair at a time and never would grab a pair when the “load” only had one or two pair. I collected all of these treasures and kept them in one of my bedroom dresser drawers and would occasionally try a pair on and it would get me aroused. I didn’t know what I was going to do with my collection, but I loved having them in my drawer.

I had only been living in my apartment for about six months when I started my collection. I had recently moved back to Southern California after spending three years working in Arizona. I had received a job offer to become a sales representative (with lots of travel) requiring me to move back to Southern California. I accepted immediately due to the great money; and that is how I ended up in this apartment in Pasadena. I had a girl friend, Beth, in Arizona, and when I moved away we decided to try and keep in contact and see if she eventually wanted to move to Southern California also. But, as I told you in the beginning, my lifestyle was a little wild upon my return to SC and it was not conducive to maintaining a long distance relationship.

When I first moved back I made several trips to Arizona (it was part of my territory for work) and visited with Beth. In addition she made two trips out to visit me in Pasadena. On her second visit, she actually left a couple of swimsuits to have available when she visited, but she never did visit again. I had forgotten about these bathing suits until one day when I decided to re-arrange my drawers (to organize my collection of panties) and discovered the two suits in the bottom of my drawer that contained my own swim trunks.

I pulled the two bathing suits out of the drawer and looked them over. The first one was a one-piece white suit with a matching white belt and bright gold buckle. It had two straps to go over the shoulders and a nice plunging neck line and was very form fitting. Beth had a very slender body and this particular suit was not her favorite, but it fit her very well. The other suit was a zebra print two piece bikini, the top did not interest me, but the bottom was very thin and “high riding” on the sides. I immediately took all my clothes off and put the bikini bottom on.

Wow, I am already this far along and have not told you what I look like (except for the “baby face”). I am about 5 ‘9 tall and in those days I weighed around 165 pounds. I had really been doing a lot of sit ups, so I had a nice flat belly. Not skinny, not fat, just normal. I have a baby face, not much body or facial hair (a full head of black hair on top) and unfortunately a small four inch penis (maybe a little longer when hard). No, it is not very thick either.

When I slipped these bikini bottoms on, they felt great on my body. I immediately became hard when I looked in the mirror…they felt amazing, they were so much stronger than a pair of panties and felt like they were massaging my balls. My cock stood up and came out the top of the suit and yet my balls felt so secure yet strained in my bikini. It was an incredible feeling.

At first I had no thought of trying on the one-piece, but now I had to know how it would feel on my body…I stepped out of the bikini and stepped into the one-piece swimsuit one leg at a time. I pulled the shoulder straps up and slipped my arms through the holes and straightened my shoulders so that the suit became very taut and I looked in the mirror. Oh my God, I had never felt a sensation like this, it was so amazing. I felt the tight fitting suit everywhere it made contact with my skin. Beth was thin and short so the suit was stretched very tight on me, it made me tingle. I couldn’t believe that I was wearing my ex-girlfriends’ swim suit and I was getting aroused! Immediately a plan rushed through my head for later that night.

That night around 7 PM, I grabbed some fast food at Del Taco (a fast food chain) and ate a quesadilla and taco in my car as I drove to my favorite bar. At the bar I had a typical visit; I played some pool, watched sports on the TV, drank a few cocktails and chatted with my friends. Around 11 PM I drove home to my apartment and poured myself another drink. I stepped out of my clothes and went into my bedroom and slipped on the white one piece bathing suit. It felt so good; the nylon stretch fabric felt like it was attached to my body. I loved the sensation of inserting my arms through the suit and stretching the shoulder straps over my shoulders.

I looked in the mirror and loved the way I looked in the suit, but mostly how good it felt on me. I refreshed my drink and put on a robe, grabbed my fresh drink and stepped out of my apartment and took the short walk to my apartment swimming pool. The apartment was old and I think the pool was built at the same time the building was constructed. The pool was not big, only about 40 feet long and 20 feet wide. The pool did not get a lot of sunlight; therefore, there was not a lot of room around the pool for sunbathing. It was surrounded on three sides by the apartment complex itself and the fourth side by a six foot adobe brick wall. It was a very private location. You could access it from three directions and at this time of night the only risk of anyone seeing me in my women’s bathing suit was an entrance to the parking garage next to the pool.

If someone coming home and was returning to their apartment using this entrance would see me in my feminine attire, but I wasn’t too concerned. I slipped out of the robe and placed it on the back of one of the chairs at a table. I took a sip of my drink and then I dove into the pool. I started to swim across the pool in my women’s bathing suit. I was nervous, excited, exhilarated, and probably scared! I swam a couple of laps, as a hundred thoughts rand through my mind….”What am I doing?” “What if someone sees me?” “What will I do if someone sees me?”…Thank goodness no one showed up and when I finished my laps, I jumped out of the pool.

Not bothering to dry off, I slipped on my robe, grabbed my drink and returned to my apartment. I was so aroused upon my return that I immediately slipped off my robe and pulled my cock out the side of my bathing suit. I started playing with myself and I stroked my cock until I shot my load all over my hands and my soaking wet suit.

OK, this was getting weird, why did I like wearing a women’s bathing suit? Why did I get so turned on about being in public wearing it? A more troubling part was I wanted to take it a step further, but was unsure what to do next.

The next day I was traveling for work and was selling some product to a small store in a strip mall. When I left the appointment, I saw a Salvation Army store next door in the same shopping center. I am not sure why I decided to go into the thrift store, but I went in and started browsing and went to the women’s lingerie section. They had several bras, panties, night gowns and slips. I was getting very excited looking them over. I picked out the sexiest bra they had (a red lacey one) and went over to an area where they had leotards tops. I saw how these leotards snapped around your crotch and thought they would feel great on my body. It would be like the one piece swimsuit, but with more coverage. I selected a black leotard with long sleeves and a scoop neckline. Then I went back to the bras and picked out a second bra, this one black.

I was starting to lose control of this whole situation, I was holding two bras, a black leotard and wanted to look and buy more. I went to the clothing racks and was really fascinated by the skirts. Wow, I could pick out a whole outfit at this thrift shop and dress up. Everything was so cheap! I did not know how to size anything (I hoped the bras were ok), so I selected a short black skirt with an elastic waist line, hoping it would fit me. I spent only about $20 and had the beginning of a women’s wardrobe.

I could hardly wait to get home and try them all on. I sped down the street, hopped on the freeway and thirty minutes later I was in my apartment ready to try on my purchases. It was difficult, I was so nervous to be trying all this clothing on, even though I was by myself in the privacy of my own apartment. I slipped the leotard on and it felt great and so did the skirt. But I realized at that moment, that this was not complete. I needed to fully dress like a woman. Only dressing from head to toe would bring me to an excited level even greater than the time I went swimming in Beth’s suit.

Over the next few weeks, I went to a variety of clothing stores to expand my women’s clothing collection. I bought a lot of items. Some of the items did not work, because I was unsure of what sizes to buy and what would look right on my body. Other items felt and fit great! Finally I had a collection of about 30 panties (from the laundry and from shopping), three or four bras, several pair of tights, a dress, three skirts, about six tops (three leotard/body shirts), a jacket and two sweaters. I bought most of these items in second hand stores (Goodwill, Salvation Army, Thrift Shops, etc) and some cheap clothing stores. I had almost enough things to completely dress up, but was still missing some key elements that I was having difficult obtaining.

By now I had a pretty good idea of what would fit me in clothing and lingerie, so the shopping was easier. One day I was driving to an appointment and came across a part of Southern California that I had never been to. I was in a small suburb named El Monte in East Los Angeles (it is a “rough part of town”), and it featured a small shopping area of independent stores catering to Latinas. I couldn’t believe how many women’s clothing stores were here and how inexpensive everything was priced. I shopped about five stores and picked up some additional items including some sexy nylon thigh highs, a nylon/mesh “body suit”, lots of cheap jewelry (bracelets, earrings, rings, necklaces, anklets, etc) two handbags and a pair of size 11 black high heel pumps. The pumps were great, as shoes have been the most difficult item to find that would fit. I also found a great black girdle that I hopefully could wear to help me look slimmer when I wore my outfits.

As I drove home from El Monte, I thought there was no turning back. But if I was going to fully dress as a woman. I needed to get a few more items to finish the project and decided to do it right now as I was headed home, before I “chickened out”. The last steps were maybe the most difficult…cosmetics and a wig! I had tried to find a wig in thrift stores, but they never had any.

I didn’t like spending a lot of money on my “toys”, but the only place I was going to find a wig was at a wig store. I had done research and decided on my way home to go to the only wig store in Pasadena. I arrived at the store and explained to the woman at the store I was going to dress up for a costume party and needed an inexpensive wig.

She was very helpful and sold me a beautiful hair piece in dark brown with a hint of red (I think she called it henna coloring) that was almost shoulder length. The next stop was the drug store for cosmetics. I really had to guess on these purchases and bought way too much as I bought a little bit of everything. I had made a check list before I went shopping and it included a brush, head bands, mascara, eye shadow, make up, rouge, powder, lipstick, cold cream, perfume, nail polish and nail polish remover. I had a lot of bags in my car and was on my way home!

Chapter 2: All Dressed Up for Pizza

I was home later that evening and had drank about three or four cocktails (by the way scotch is my drink of choice, but I also like beer, vodka, tequila, champagne and rum) and was feeling pretty good. I stripped off all of my clothes and placed them in my laundry basket and now I was ready for my first full wardrobe and cosmetic dress up. I went to my bathroom and decided the first step was a shave. I pulled out my electric razor and shaved my face thoroughly.

I pulled out my Noxzema shaving cream can and squirted out a generous portion of the shaving cream in my hand. I spread the cream over my chest and also dabbed some on parts of my underarms. I pulled out a disposable razor and shaved my chest down to my nipples and then carefully shaved about half of my underarms. I pulled out a pair of scissors and clipped my remaining underarm hair to a very short length. I stepped into my girdle and slid it up my body until the bottom of it was above my waist. It was about six inches from top to bottom and when I looked into the mirror, it made me look ten to fifteen pounds lighter.

I slipped on a pair of black thong silk panties and a black lacey bra. Next I slid on a pair of nude colored thigh high stockings and then put on a pair of black mesh (fishnets) thigh highs over the nude colored thigh highs. This covered my legs, so that you could not see any of the hair on my legs and it still looked very natural. I slipped on the black skirt (from my first shopping experience); it was very short and clung to me because of the stretch material it was made from. Next I slipped on a clingy stretch long sleeve v-neck black blouse and tucked it in my skirt. I put on a wide black patent belt and cinched it very tight.

I then applied my make up in the bathroom, which took forever, as I had to experiment. I ended up using a lot of mascara, a little eye shadow (blue), liquid make up and lots of rouge on my cheeks. I cleaned up the bathroom and went back to my bedroom where I slipped on my black pumps and grabbed my wig. Back in the bathroom I put on the wig, I selected a black head band to slip around my head to make my hair (wig) look better. I ran a brush through the wig to style it a little bit.

Then I slipped on a silver bracelet on each arm, a long silver chain around my neck, a silver choker necklace, two big clip-on hoop earrings and a silver anklet around my left ankle. Next I slipped on my black high heel pumps. I decided to pass on nail polish, as it would have taken me forever after the make up marathon. Lastly I applied a healthy amount of fire engine red lipstick, sprayed some perfume around the back of my neck and the transformation was complete.

I studied myself in the mirror and thought not bad, not bad. I stepped into my bedroom and slipped on a long sleeve short red jacket. It was very cute, I liked the black fake fur collar on the jacket and it looked great with my black outfit. I looked in the mirror again and decided to put a sock in each side of my bra to fill it up a little bit to give the appearance of a modest set of breasts.

I did a couple of spins in front of my dresser mirror and I really felt like the old saying…”all dressed up and no where to go” was very appropriate. I had not given a lot of thought of what to do when I finished dressing, but there was no way I was going drive anywhere. I had now consumed at least six drinks (I was drinking the entire time I was getting ready) and felt mildly drunk.

I practiced walking in the heels around my apartment and even though they were at least three inches high, I was pretty good and very well balanced. I felt like a girl and I think I looked like a girl. I know I am not the pickiest guy in the world when it comes to women, but I know if I saw a girl like me in a bar, I would certainly try to pick her up, especially if she were as drunk as I was now!

I took one more look in the mirror, slipped a black handbag around my shoulder, and then I opened up my door and went for a stroll down the hall of my apartment complex. I didn’t see anyone on the first floor, so I took the stairs down to the garage. I strolled across the garage and walked out the front gate and was now standing in front of my building.

I was glad that I had packed my handbag with some key items. I had a set of keys to my apartment, my drivers’ license, some money, lipstick, hair brush, a pack of cigarettes and a lighter. It was a beautiful evening around 9 PM, the weather was cool for Southern California around 65 degrees and I decided to have a cigarette.

I was standing on the sidewalk, near the driveway entrance to the parking garage of my apartment complex fully dressed as a woman and loving the feeling. I had been outside about ten minutes and a couple people walked by and said “hello” another person ignored me and one guy gave me a very long look and said “good evening”.

I think I looked kind of slutty in my outfit, but not like a whore. It was an outfit you could wear out to a bar and the guys would know that you were probably available for a drink or two if not something more. I spent about fifteen minutes more outside and walked around the block. I probably passed about a half dozen people that were also walking, but just a common “hello” was all that was said. Several cars passed by and I received a lot of looks from guys in cars, even one guy whistled at me.

When I got back to my apartment complex, I saw a car with a Domino’s pizza sign parked near a house across the street from my apartment. This gave me an idea; I would call for a pizza to be delivered to my house and see what reaction I received from the delivery boy. I walked down the hall towards my apartment and even passed my landlady on the way, she said hello and kind of looked at me strangely, but she did not say anything more.

In my apartment I looked up my pizza delivery options in the phone book and decided to order from a place that I have never used before. I called the pizzeria and ordered my food in my most feminine voice. They asked for my name and the first name that came to mind was Sandy. I was told it would take about 30 – 40 minutes, so I refreshed my drink and waited for my pie.

I was so nervous that I decided to go out on my balcony and smoke another cigarette. My balcony was mostly private; however there was one house next door that was clearly visible. I rarely saw people looking in my direction from this house and tonight was no exception. The house was about 50 feet from my balcony and I could see in their kitchen window.

I was hoping that someone might see me, so I turned on my outdoor patio light and lit up my cigarette. The smoke calmed my nerves and eventually I did see someone enter the kitchen and approach the sink that was located below their kitchen window. It was an older man around 50 or 60 in the window and after a couple of seconds he looked up and we made eye contact.

He smiled and I smiled back, I pretended that I needed to adjust my shoe, so I placed my foot on the balcony wall so that he could see my long left leg. I have to admit, my legs looked very good in my mesh thigh highs. When I looked up at the window again, he was clearly staring at the little show I was putting on. He smiled again and I winked at him and smacked my lips like a kiss. He smiled back and gave me a wink, and then I put out my cigarette and walked back in my apartment.

I went into the bathroom and gave myself a little freshen up with the hair brush, mascara and lipstick. I sprayed myself again with my new perfume while I was thinking my pizza will arrive any minute. The buzzer to my intercom went off a few minutes later. My apartment complex required you to “buzz” any visitors in and the intercom was a voice system that allowed you to verify who was trying to enter. I held the speak button and said, “Yes?”

“Pizza Delivery for Sandy,” a voice replied.

“Come on in, my apartment is down the hallway to the right,” I said in the most feminine voice I could muster.

He knocked on my door in no time and I opened the door. He was a young Latino man around 20 wearing blue jeans and a long sleeve blue (chambray) button down collar shirt. He was not tall only about 5’ 7” and was wearing white tennis shoes and was carrying a cardboard pizza box with a small white bag balanced on top of the box. I said, “Come in, you can put the pizza on the dining room table. How much do I owe you?”

“Twelve dollars and seventy five cents,” he replied in a very strong Latin accented voice.

“Ok, let me get my purse.” I walked away from him towards my bedroom and glanced in the mirror on the wall to see if he was watching me. He was! I could see in my brief glance that he was checking out my ass and legs as I strolled away.

I was getting so hot that he was watching me, probably thinking he would like to fuck my brains out! I was back in a second and I pulled out a $20 bill from my handbag. I handed the money to him, but I dropped the $20 on the floor (pretending it was an accident). We both bent down to pick it up and when we were both near the floor; I brushed my hand down his arm, but made it appear that this skin contact was an accident.

“Just give me back two dollars change,” I said.

He placed the $20 in wallet that was attached to his jeans by a chain attached to a belt loop. He pulled out two one dollar bills and when he handed them to me, I made sure that our hands touched each other.

“Thank you Senorita,” he said. “That is a very nice tip!”

“My pleasure,” I replied. “Too bad you can’t stay for a while and have a drink, I hate drinking alone.” At this point I picked up my glass and took a very seductive sip of my scotch.

“I have to go back to work, do you live here alone?” he asked.

“No, this is my brother’s apartment, he is gone for a few days and I am house sitting.” I had thought of this little white lie in advance of such a question.

“Well maybe I could come back later, I get off around 10:30 or 11:00." He came up right next to me and put his right hand on my left hip. I couldn’t believe this! I felt so much like a woman and here I was flirting with a delivery boy. I knew this was the time to do something, so I decided to make an aggressive move.

“I know what you want; you don’t want a drink, do you? You want me to suck your cock!” I moved my hand to his crotch and gently squeezed his package. He didn’t quite know what to do, so I leaned down and kissed the side of his mouth, he gently started to kiss me back and slid his hand all the way around my waist. I opened my mouth and felt his tongue slide inside my mouth. I closed my eyes and it felt just like kissing a girl, I was drunk and I was loving the feel of it.

“Do you have five minutes to have a little fun before you have to go?” I managed to say in between kisses.

“Sure,” he groaned.

I grabbed his hand and sat him down on my couch. I unbuttoned his jeans at his waist and unzipped his fly; then I slid down the jeans all the way to his ankles. He was wearing navy blue boxer shorts and his cock was already hard, because it was poking out of the front of the boxers. I slid his boxers down to his ankles with his jeans and looked at his cock. It was not circumcised and it looked to be about five or six inches long and not too thick. Other than being uncircumcised, it appeared to be an average dick, but it would be the first one (other than my own), I had ever touched.

I had never done anything like this, but I had seen enough porno movies and had received enough blow jobs to know “what” and “what not” to do. I gently started stroking his cock and it became even harder. It was now a full six inches long as it grew when I played with him. I peeled back the foreskin and saw the head of his cock before slipping the trophy into my mouth. He moaned and I went down as far as I could on his dick.

I opened my mouth as wide as I could and finally closed my lips around the shaft of his cock. I gently raised my head letting my lips run along the full length of his dick while I sucked in. Then I licked his ball sack and licked the entire length of his dick. I pulled back the excess skin and licked his entire head. Then my mouth went back down on his cock again, I could feel it starting to gag me so I slowed down and went down farther and farther until I had almost his entire cock in my mouth. He was now rubbing my back as I sucked his cock.

“God! That feels so fucking good! Suck my cock bitch!” He was talking dirty and loud and I loved it.

I stroked the base of his cock while I went down on it again, being careful not to touch his cock with my teeth, I started going up and down on his cock with my mouth, tongue and lips while also stroking the base. Faster and faster I went, and he was pumping his ass up in the air to fuck my mouth….he pushed the back of my head down on his cock and I took his full length in my mouth. If he only knew how fucking hard I was in my panties while I was sucking his beautiful cock. I don’t know how, but I knew he was about to shoot his load…I continued to suck his cock, but I slowed down the pace, he was starting to breathe hard and said, “I am cumming!”

True to his word I felt the first shot of cum hit my tongue and inside of my mouth. I thought it would be hard to swallow, but it was easy, it actually tasted great and I was sucking and stroking every drop out of his cock so I could swallow it all. The whole blow job took about five minutes; it reminded me of those quick blow jobs I received in my car from hookers.

“Hey baby, did you like that?” I asked as I stood up and went to the table to get my drink.

“Oh yea baby! Fucking great.” He was pulling up his pants and underwear.

“OK, well you better get going, your boss will be wondering what you were doing. Now this is our secret right? You can brag about it, but don’t tell them who I am and where I am staying. My brother would be pissed if he knew what I was doing in his apartment,” I told him.

“No problem, but if you want another pizza the next couple of days, I am working nights, my name is Carlos.”

Let me know if you like the beginning of this book, more chapters will be published if you like the story.