There are many reason why we crossdress, a desire to express our feminine side, a need to change your sexual identity, sexual inadequacy, or just the need to feel the silkiness and femininity of women's clothes against our body. In my case, I had a shoe fetish. I was really turned on by women in high heeled shoes. I could never get enough. I masturbated incessantly. As I got older, I bought my own heels, then progressed to women's clothing, lingerie, dresses, skirts blouses, then makeup and wigs. What I didn't buy, I borrowed from my sister or my mother. I was never more than 135 pounds at 20 years of age and 5'10". My build resembled that of both my sister and mother. When dressed, I was amazed at how closely I looked like them. Now for my story......
I had come home from college for the holidays and really had the urge to dress. It had been too long a period of time. Both my mother and father worked and my sister had not as yet returned home from college.
It was Friday and I knew that my father usually went out with the boys after work and wouldn't be in until around 1:00 in the morning. My mother was a nurse and was working twelve hour shifts and wouldn't be in until around 3:00 AM. This gave me plenty of time to have a great day of dressing. I could dress for nearly twelve hours.
I pulled out my suitcase containing my wardrobe and looked to see what was here. I didn't really feel like wearing the same old stuff and figured that in the three months since I had been home that my mother must have bought something sexy. Since she had a slender body, she had a tendency to buy most of her clothes a little short and tight. She almost had model quality with her long blond hair. I was not disappointed. I found a black dress that still had the tags. I t had a single strap, open back and stitched loosely on the side leaving a nice see through appearance on the left. I started to get excited when I took it out to examine it more closely. I didn't think I would have any problem fitting in to this dress. I rummaged through her lingerie draw and found a garter belt, black stockings, a black bra and black thong. I felt a throbbing in my jeans.
I quickly jumped in the shower with my razor and shaving cream. I took a very close shave, shaved my armpits, legs and pubic area. I felt smooth as a baby. I took the thong and did a great job of tucking. I put on the bra and inserted my silicone implants, and finally my garter belt. I slowly rolled the black stockings up my long clean shaven legs and fastened them in place.
Next, I sat at the dressing table and started to apply the makeup. I had seen both my mother and sister do this so many times and had done it so many times myself that the transformation started easily. First I applied foundation. It went on smoothly and creamy. Fortunately both my mother and sister bought good makeup that was easy to use. I then did my eyes with eyeliner and false eyelashes. I applied some mascara and finally a bright red lipstick followed by a gloss lip balm.
I searched the jewelry case and found a nice gold necklace, some bracelets, a few rings and put them on. I then applied the presson nails and let them dry and become secure. I followed this up with a long blond wig. Knowing how good I looked in black anyway, I found a nice pair of patent leather pumps with a 5" heel. I had practiced wearing heels for such a long time that walking around in them was no problem. With everything in place, I walked over to the full length mirror and was amazed to see both my mother and sister staring back at me. It was almost frightening, but the look was so fantastic that I started to feel some excitement in my thong.
All this took over an hour and a half, but I still had at least ten hours before anyone would come home. That gave me plenty of time to have fun and still be able to reluctantly transform myself back.
I walked around the house stopping in front of every mirror. I even ventured out when the mailman arrived. He gave me a big smile and said "Good morning Mrs. Evens, how are you today. You look so much like your daughter, but I know that she hasn't returned from college yet." I gave him a big smile and our hands touched as he gave me the mail. As I turned to walk back in to the house, I could see in the storm door glass that he continued to stare at me. There goes that bulge again. I'm sure I could have invited him in. I know he would have jumped at the chance. My mother often said that he really had an eye for her.
I felt more comfortable now and as the sun was starting to set, I felt that I might walk down to the strip mall near our house without drawing too much attention. I did feel that I better take off the high heels as they would certainly draw more attention. Who walks out looking whorey at 5:00 in the afternoon. I put on a nice pair of flats and a long coat to hide the sexy dress, but I made sure that the coat was short enough to still show off my legs.
It felt so natural walking down the street and waving a neighbors that thought I was my mother. If they wanted to talk, I indicated that I had a sore throat and could only talk in a whisper. No one ever caught on. In the strip mall, I walked in and out of the stores, getting smiles and looks from both females and males. As I left, a few younger guys came up to me thinking I was Tiffany, my sister and asked me out. I wasn't sure what to say, but I told them to call me over the weekend. That bulge was getting even harder.
Much to my surprise, I got a tap on the shoulder. I turned and saw that it was the postman. Even close up, he still thought he was my mother. He started with small talk and that quickly changed to asking me out. I know that your husband drinks and probably doesn't take care of business he said. I sure you need a real man to take care of your needs, he said. I didn't know what to do. I couldn't just run off, but I didn't want to encourage him either. What would he do or say the next time he saw my mother. In a whisper I said, "Oh Joe, things aren't that bad. But thanks for your concern, you are so sweet." I turned and left. I felt I better get home before I get in to any more trouble.
By the time I got home, I thought my cock was going to burst through my black thong. I couldn't wait to get to the mirror and see what the bulge looked like. To my surprise it wasn't that noticeable, but I pulled it out and started to stroke my cock as fast as I could. Before long I was cumming. I always wanted to taste cum, but I shot my load so quick it splattered all over the mirror. I was going to lick it off, but said I'll clean it up later instead. I was looking so hot and thinking of being hit on at the mall, I soon was hard again and repeated the process all over again.
Feeling a little spent at this time, I lay down on the couch for a few minutes to rest my eyes. Well of course, those minutes lasted for a couple of hours and I was startled by a door closing. I bolted up to see my father staggering in. I was petrified. I didn't know what to do. Before I could do anything I heard my father say, "So, Linda, you waited up for me." In his alcoholic stupor and the poor lighting, he thought I was Mom. He came over and sat at the edge of the couch. He stroked my hair and started to feel my ass. "Linda," he said, "Tonight I'm going to get what you so often deny me. I want you to suck my cock, then I'm going to stick it up that beautiful ass of yours. You look so hot tonight."
I didn't know what to do. I never sucked a cock and certainly had no experience with anal. He started to kiss me and run his hands all over my body. He put his tongue down my throat. At first I thought I would vomit, but before I felt very comfortable. His hands started to grope under my dress, but I had tucked so well, that he never knew what I was hiding even though I felt it would burst. My balls were so full and ready to explode once more. He stood up and opened his fly let his pants fall to the floor and stepped out of them. He then moved so his throbbing cock was only a few inches from my mouth. To my surprise, I was anxiously waiting to break my mouth cherry. As he moved closer, I could smell a little piss on his cock. I also saw some precum and was getting hotter. He started to rub his cock over my lips. I reached out and grabbed his balls and slowly rubbed them. I moved closer and put them in my mouth and sucked on them.. I was getting so excited that I put this huge thing in my mouth and started sucking. I felt so natural. After what seemed an eternity, he started to fuck my mouth. I kept moving my mouth up and down and felt his balls start to twinge. Suddenly he stopped. "It's time Linda, " he said. Time for what I wondered.
He told me to roll over and get on my knees. He started to grapple with my thong and pulled it down. The next thing I felt my father kissing my ass and putting his tongue up my asshole. He stopped and I felt his throbbing cock at the entrance to my asshole. Without any lubrication, he started to enter me. At first it hurt a lot, but with the precum on his cock it slid in without any trouble. He started to fuck me in a constant rhythm, in and out. The rhythm came faster and faster. Suddenly I felt a hot liquid fill my ass. He came in me just as I simultaneously shot my own load. I lay back. He went back in to the kitchen to get a beer and I just relaxed on the couch.
When he came back, his cock was rock hard again. He wasted no time in putting it back in my mouth and started fucking my mouth again. This time is seemed no time at all before he was pumping really hard. I felt the first squirts of his load shoot into my mouth and down my throat. I had never sucked a cock before or had even tasted cum. Now I was a regular cocksucker. I just blew my father. After I realized what had just happened, I got up off the couch and went up to my sister's bedroom to take off my girlie clothes. My father fell back on the couch and fell asleep.
I sat on the bed for a long time, feeling the cum ooze out my asshole. I don't know how long I sat, but was startled by a door closing. I thought it was my father coming upstairs, but when I looked up, this time it was my mother coming in the room. "Tiffany," she said, "When did you get home? You look terrific in my dress, so sexy." I couldn't believe that my own mother didn't even recognize me. "I've missed you so much since you've been away, my vibrators been working overtime."
With this, she started to stoke my hair and gave me a kiss on the cheek. What was going on here. Next, she kissed me hard on the lips her tongue working to pry into my mouth. As her tongue explored my mouth I felt my cock wanting to get out of it's prison. I couldn't break the moment and decided to play along.
My mother started to move her hands all over my body. I instinctively started my own exploration. I open her nurses uniform and put my hands on her breasts. Through her bra, I started to squeeze her nipples. She seemed to get great pleasure from this. I reached around and unhooked her bra. Her tits fell away and I could resist putting each one in my mouth. My mother seemed to be in ecstasy. She started writhing and feeling my artificial breasts and putting her hands between my legs, then probed my asshole. She then pushed me back on the bed, stood up dropped her panties and the started to straddle my face.
I put my tongue as far as I could in to her cunt. She bounced up and down on my face moaning feverishly. Before long, I knew she was cumming. After she came on my tongue, she got up and went to her room. She came back with a strap on cock. My eyes nearly bugged out of my head. She told me to roll over on my back. She indicated that she was saving my virgin pussy. She had me put my legs on her shoulders as she inserted this huge cock up my ass. After a few minutes, my hole started to get raw and sore, so I started to gyrate my self and then gave the impression that I came. She leaned over, gave me a big wet kiss, with her tongue once again going in my mouth. She said, "Goodnight sweetie."
Was it over, what was going to happen in the morning? What about when my sister came home? I couldn't worry about that. I was just flying. I had never had so much sex in one night and had never cum so much. In the words of Scarlet, I'll worry about that tomorrow!"
There will be a tomorrow and that will be Chapter II. If you have comments, email me at orchidsten@aol.com. I'll get back to all and send pictures if you like. Tell me your interest and I'll see if I posed that way.