Author's Note: The following is purely fiction and the property of the author. Any feedback would be greatly appreciated.
It was the first week of June and school was out for the summer, I was 18 and had just finished my Senior year. One night while we were eating dinner, My Mom and Step dad informed me that they were going away for a week. When they got married they did not go on a honeymoon so they wanted to take one now.
Curt, my step dad told me they were going to Jamaica for a week and asked me if I could keep out of trouble while they were gone. Of course I told them I would be fine. Mom seemed like she did not want to leave me alone and I knew Curt did not want me to go with them on the trip. Now I would love a week in Jamaica but I had my reasons for wanting to be left alone for a week.
I had been dressing up in my Moms clothes for almost two years and the idea of being able to dress for a week sent all sorts of ideas through my mind.
Mom reluctantly agreed that I could stay by myself, but she said she would call me every day and that my Aunt and uncle might drop by from time to time to check on me.
We lived in a very upscale neighborhood. Curt worked for a software company and he loved to restore vintage cars. I had to drive an old beat up VW bug. It was a piece of junk but it got me where I needed to go.
Early Friday morning I helped Curt pack their luggage into his car and watched them drive away. I wanted to run back into the house and change. It was all I could do to resist the urge, but I knew I would have plenty of time to dress up.
I am 5'9" 160 pounds, blonde hair and blue eyes. My name is Robert, but when I am dressed I call myself Vicki. Mom was not fat but she did wear clothes that were lose fitting. Lose fitting on her meant tight on me. Some are tighter than others on me but I could wear almost all of her stuff even her heels and boots.
I had plans to dress completely later that night but for now I went to my Mom's bedroom and picked out a sexy pink bra and a matching pair of pink satin panties to wear. I went back to my room and undressed. I hooked the bra in front of me and slide it around to where the cups were in front and slide my arms through the straps. I then slide the panties up my legs. Mom wears a 34B size bra so I had to pad the cups with some old pantyhose.
I was already rock hard and dripping pre cum. I have a small cock, only 4 inches at most when I was hard. I laid down on the bed and started running my hand over my crotch. The material felt so good.
I was squeezing and rubbing my cock through the material and soon I felt that wonderful feeling start to go through my body. Not wanting to make a mess in my panties, I slide them down my thighs and started stroking my cock with my left hand. I knew I was going to cum soon but I tried to hold off as long as I could. I could not hold back any longer and I came. I tried to catch it all in my right hand and when I stopped shooting I brought my hand to my lips and licked it clean, savoring the tasty juices as I swallowed.
It was still early so I pulled my panties up, got under the covers and went back to sleep. I woke up around 11 and was hard again. I was tempted to jack off again but decided to wait.
I put on an oversized T-shirt and went to get something to eat. Usually I have to lock myself in my bedroom and hurry to get off so I can put the clothes back before Mom notices that they are missing. It felt exciting sitting at the table wearing a bra and panties, just eating breakfast.
After I finished eating I decided to watch some TV, nothing good was on so I went to my parents bedroom again and got a video out of the closet. Curt had a big collection of porn. The one I chose was a collection of three sums and gang bangs.
The first few scenes were kind of boring, then it got to a scene where a cute blonde was used roughly by two men. I was already hard and imagining I was the hot blonde being used just turned me on even more. I quickly removed my T-shirt and laid down on the couch in just my bra and panties.
While the blonde on the screen was sucking one guys long hard cock another guy got behind her and shoved his cock into her pussy. I could not help but imagine myself in her place. The guy getting his cock sucked reached down and started roughly pinching and twisting the nipples of the blonde.
I instinctively moved one hand up and started pinching my own nipples. I am not sure who was moaning louder, me or the blonde on TV. I wondered what it would be like to be fucked like a woman.
As my right hand pinched my nipples I slipped my left hand into the back of my panties. I started running my finger between my ass cheeks. I started to push a finger into my ass but chickened out and went back to rubbing my cock with my left hand. I knew I could not hold out much longer and I was not able to pull my panties down in time so I shot my second load of the day making a sticky mess in my pink panties.
I laid there for a few minutes catching my breath and then I went to change. My best friend Gary was coming over soon to hang out and since no one knew about my dressing, I did not want him to find out.
I washed out the panties and hung them up to dry. I hung the bra in the bathroom with the panties and went to put my "guy" clothes back on.
When Gary got there he kept telling me that we needed to throw a party, I kept telling him I had promised Mom and Curt that I would not have one. I did not make that promise but my desire to dress up was bigger than a desire to have a party. We played video games, ordered pizza and just hung out.
Around 7 PM when Gary finally realized there would not be a party tonight he decided to head home, he said he would call me tomorrow and try to talk me into having a party.
I waited a little while just to make sure Gary was not coming back for some reason then I went around and locked the doors and closed the blinds. I went to my Moms bathroom and got a razor and shaving cream.
I took my time and shaved my legs, my underarms and I trimmed my pubic hair into a neat triangle. I had very light blonde hair on my body anyway and I hoped that no one would notice that I have shaved my body.
After I shaved I started a bubble bath. I added some vanilla and jasmine to the water and decided I needed a drink, I went to the kitchen and got a bottle of wine and a glass and brought it back to the tub.
I lowered myself into the water and enjoyed the warm relaxing bath. I poured myself a glass of wine and started sipping it. I felt so feminine and grown up while I pampered myself. I imagined myself getting ready for a hot date with my boyfriend.
By the time I finished the second glass of wine the bath water was getting cold. I finally forced myself to get out of the tub. My body was tingling as I dried off and then wrapped myself in a fluffy towel and headed to the bedroom.
I was glad to see that Mom had packed light for their trip and most of her sexier clothes were still here. I knew exactly what outfit I wanted to wear and started laying it out on the bed. First was the matching black lace bra and panties. Then the short tight black skirt and I chose to go with the skirt a silk white blouse.
My legs looked great and was silky smooth after I shaved them but I decided that my legs would look even hotter clad in a pair of black pantyhose. I started to put the panties on but decided to put the hose on first then the panties.
I tried to ignore my growing cock as I dressed. Good thing I was so small because even hard the pantyhose and panties kept it hid for the most part. by the time I was buttoning up my blouse and tucking it into my skirt I was on a third glass of wine and feeling a slight buzz.
My hand was a little shaky as I sat at my mom's vanity table and applied makeup. While I had been dressing for a couple of years I did not get many chances to practice putting on makeup. I applied a little blush, some blue eye shadow and dark red lipstick. I looked a little slutty but not to bad. My mom had some big clip on hoop earrings and I attached them to my ears. I used my Mom's hair gel to spike my hair like some teen bad girls like to do.
I sat on the bed and stepped into a pair of black pumps with a modest 2 inch heel. Eve though they were not to high I still stumbled a little and almost feel until I got use to the shoes. I am sure the wine had something to do with it.
I was now ready to look at myself in the mirror. Looking back at me was a somewhat pretty tomboyish looking girl with a decent set of breasts andnice legs. I decided to get online and maybe go into some chat room and flirt with some guys.
While I was online I looked at one of my favorite adult erotica sights and read some stories about cross dressers and transvestites. One story caught my eye, it was about a CD who decided to take a chance and go out driving late at night.
I read a few more stories but went back to that particular story. I started thinking how exciting it would be to go for a drive while dressed up. I could do that, maybe just a drive around the block. It was almost midnight by then and I had convinced myself they would not be any traffic out this late.
I knew I should stay in but I could not get the idea out of my head. I finally decided to do it. I got my keys and went to the garage. I turned the key but all I got was a grinding noise. My car would not start.
Disappointed I got out and had almost decided to try and get a new battery tomorrow and maybe go out driving tomorrow night. Then I seen my Step dad's latest project setting there.
It was a classic candy apple red mustang convertible. he had been working on it for months and just recently finished it. I couldn't take it for a drive could I? I mean it was just going to be a quick trip around the block and I would be back in a few minutes. No one would have to know.
I went to Curt's study and got the keys. Did I really want to do this? My heart was pounding as I put the top down. I felt naughty as my skirt rode up my thigh as I slid under the wheel. This time when I turned the key the mustang purred to life.
I backed out into the driveway closing the garage door behind me. I pulled out onto a deserted steet and started to drive slowly getting use to the mustang. By the time I circled the block a few times I was feeling comfortable and picking up speed.
I was imagining how I looked, A sexy blonde in a hot convertible. I bet I would be driving the guys wild if they could see me now.
That is when it happened. I rounded a curve and there was a SUV stopped in front of me waiting for another car to turn into a driveway. I tried to stop but I was still not use to driving in heels and my foot slipped off the brake. I ran into the back of the SUV.
OH SHIT!!!!! What am I going to do, I thought about backing up and driving off but the car stalled. I sat in the drivers seat crying, praying that this was just a vivid dream and I would wake up soon.
The knock on the window brought me back to the present. It was Mr. James, A man that live up the street and he was saying something.
I rolled the window down to hear him asking if I was ok. I shook my head yes but could not stop crying. Mr. James put his hand on my shoulder and said,"It will be ok pretty girl, as long as you are alright. I just need to call 9-1-1 and get the police out here."
I screamed Please!!!!! NO!!!!
"But we need the cops out here to file a report for the insurance companies, you do have insurance don't you?"
That is when he recognized the car. "Hey this is Curt's car, I seen him working on it from time to time, They are out of town on vacation. No wonder you do not want the police, you are driving a stolen car."
"I did not steal it I borrowed it. please can I just go home?"
"Where do you live young lady?"
Without thinking I gave him my address, that is when he shone a flash light into my face. he stopped dead as he realized who I was. By now his wife came back to see what was taking so long.
Mr. James opened the door and ordered me to get out. I did not move. He reached in and took my arm pulling me from the car. His wife asked him why he was so rough. Why was he being mean to a girl who was obviously scared.
He Started laughing as he told his wife that I was no girl then told her who I really was. She did not believe him. "That is no boy, let her go."
Mr. James was still holding my arm. "The guys at the police station are going to love you. You better hope they put you in a cell all by yourself."
"Please no, can't we work this out ourselves? I promise I will pay to get your car fixed. Just don't call the police."
He had quit laughing and was looking me up and down, "I think my car is the least of your problems, I smell alcohol on your breath. Plus I have a feeling Curt will go ballistic if the police calls him and tells him you have wrecked his mustang while driving drunk."
Oh God I was not even thinking of Curt. "Please Mr. James I will do anything, lets just work it out without the police."
"You will do anything?"
I nodded without thinking, "Yes anything just don't tell Curt of call the police."
Smiling, Mr. James told his wife to get into the mustang and to follow us home. She asked him what he was up to but he ordered her to just do as she was told.
He led me to the passenger side of the SUV and opened the door and told me to get in. He went around and got behind the wheel. Mr. James reached over and pulled the seatbelt down, buckling me in. As he did he put a hand on my thigh, he slowly worked it up until he felt the edge of my panties.
"I was hoping you were wearing stockings, but pantyhose can be sexy also."
I was still shaking in fear because I had no idea what I was going to have to do to get out of this. His comment sent another shiver up my spine and made me blush.
It was just a few minute until we pulled into the driveway at The James's Home, It was a huge, very expensive home with a four car garage. After he had parked the car he got out and motioned for his wife to pull the car into the spot beside the SUV.
He told his wife to take me inside and that he would be inside in a minute. Mrs. James took me by the arm and said "come on honey."
Mrs. James is a very pretty older woman, they are both in their mid 40's. She looked to be around 5'5" she was not fat but had nice curves and 36D breasts, and had long brown hair. She was wearing a very sexy expensive dress. It was green and the hem came to mid thigh.
Mr. James was taller, over 6' and in decent shape, he had black hair but it was started to turn gray around the temples. And he was very intimidating when he joined us in their living room. He was wearing a tuxedo.
He started by asking me, "Now Robert, you want to work this out between ourselves do you?"
I was still shaking but I managed to whisper "Yes Sir."
Mr. James smiled at me and asked, "Well what do you think you can do for me to make me forget what happened to my SUV?"
"Uh, I could do any odd jobs you need me to do around the yard and house. I can get a job and pay you back a little at a time."
"Do you really think a little yard work will get you out of this? And how are you going to hide the damage you did to Curt's mustang?"
"Oh God I never thought about that." I started crying again, "What am I going to do?"
Mrs. James put her hand on my arm, "It's ok sweetie, don't cry, I think Mark has some ideas don't you Mark?"
I looked at him expectantly, "You do?"
Mark was smiling, "Stand up Robert, let me look at you. Wait, I can't call you Robert, do you have a feminine name you go by?"
I got to my feet and whispered, "It's...I like Vicki."
Well Vicki you are a pretty girl and if you were serious about doing anything, I am sure we can work something out that will benefit both of us."
Mark took off his jacket and sat on the couch beside his wife. "Now Vicki I want you to walk back and forth for us."
I walked from the couch to the fire place and back.
Mrs. James spoke up, "Now do it again, but take smaller steps, put a little sway into your hips."
I did as I was told.
"Much better, now tell us sweetie, how long have you been dressing up?"
"Uh, just a couple of years, I am not hurting anyone."
Mark reached out and put his hand on my arm, "No one said you were doing anything wrong. Does Vicki have a boyfriend?"
I blushed a deep red,"No sir, you two are the first people to ever see me dressed. No one knows. well until now."
His wife told me, "well you did a good job on your makeup, and you make a convincing girl Vicki." Then she laughed and reached over to squeeze Marks cock through his pants. "Here is your proof right here."
She unbuttoned his pants and pulled down the zipper. She reached her hand under the waist band of his boxers and I caught my breath as his cock came into view. It was just semi hard and still almost 6 inches long. I have only seen other cocks on the Internet. This one was real and it looked huge.
I heard Mark let out a sigh, "Oh Susan that feels good."
Susan told me to slide my skirt up a little, to give Mark a glimpse of my panties.
I slowly edged my skirt up. She commented on what sexy panties I had on and for me to turn around and show them my ass.
Mark had started unbuttoning Susan's blouse and I could see she was not wearing a bra. As I completed my turn, Mark had sucked the right nipple into his mouth and was sucking hard as she continued to stroke his cock, it was hard now and had to be over 8 inches long. I could not take my eyes off of it.
Susan seen the way I was looking at it and laughed, "It looks tasty doesn't it?" I couldn't help it and licked my lips.
Susan stood up and let her dress fall to the floor. underneath the dress she had on a white garter belt, white stocking and green lacy panties. She slide her panties down and off exposing her shaved smoothed pussy.
She pulled Mark to his feet and kissed him passionately. I was having trouble deciding which I wanted to look at more, Susan's Sexy ass or Mark's hard cock.
Susan took my hand and pulled me to them. She leaned in and whispered to me to start unbuttoning Mark's shirt. As I nervously started undoing the buttons with shaky hands, Susan slide to her knees and helped him take his shoes off.
Mark pulled me to him and kissed me. Oh My God, my first kiss from a man, I had thought about kissing a man for over two years now it was happening. I was uncertain what to do so I just let Mark kiss me. He was kissing me hard and I instinctively opened my lips to let his tongue enter and explore my mouth. As Mark kissed me his hands were on my ass squeezing it through my clothes.
I know I did not have anything to compare it to but At that moment I knew Mark was a great kisser. When Susan told her husband to step out of his pants and boxers, Mark broke the kiss and I finished unbuttoning his shirt.
As I slide the shirt off his shoulders and down I couldn't resist and I planted a couple of wet kisses on Mark's muscular chest. When he hugged me tight I could feel his hard cock pressed into my tummy.
I heard Mark moan and looked down to see Susan licking the entire length of his cock. She then stood up and pulled me away from her husband. Susan pushed Mark back down onto the couch.
She turned to me and said she thought I was over dressed. It was her turn to kiss me. Susan's kisses were softer but just as exciting. As we kissed she pulled the hem of my blouse our of my skirt and started to undo the buttons.
Mark was sitting on the couch and slowly stroking his cock as he watched us kissing and Susan undressing me. When she had my shirt undone and off she reached behind me and unhooked my bra. As she removed my bra the hose I was using for padding fell to the floor.