Caught Crossdressing

This happened to me when I was 26 years old. I had been going out with Susan for about 1 1/2 years at the time. I will remember this forever. "Oh what do I do now?!" was all I could think. There I was in front of my mirror adjusting the mini skirt that I had just put on when I saw Susan, my girlfriend, coming thru my bedroom door. I was fully dressed in womens lingerie, wig, a sheer blouse, and pantyhose. I saw Susan looking me as I turned around. "What have we here?" she asked. "A little ***** all dressed up?" she asked in a mocking tone. "Do you like being a girl?" I could tell that she was confused and also upset. I was blushing terribly and could barely talk. A thousand thoughts went through my mind as I stammered "Yes, I do like dressing as a girl." My mind was racing as I did not know what to do or say! Susan was about to take care of that. "Come let me see what you done with yourself," she ordered me. I walked over to her as she sat down on a chair in the bedroom. "Um I see you have on a pair of my red silk panties, and I am guessing these are a pair of my black pantyhose," she stated as she pushed up my skirt. "Where did you get the nice bra," she asked. "It pushes up your little breasts quite nicely" she noted. "You really do look like a little ****" she mused. I mumbled that I had bought the bra, mini skirt, and blouse thru a J.C. Penneys catalog. "Oh we are afraid of going out and shopping?" she said laughing. "Afraid of being caught?" she said. "Yes" I said. I was indeed afraid of being caught, like I was now. But now, I was almost feeling relieved that I had been caught and it was not longer a secret. "Well, I am shocked at this" Susan said. "What am I to do with you?" she said, "call your mother and let her know?" "No, please do not do that, I will do anything you want, but do not tell her" I begged. She knows that if my mother ever found out about this, I would never be able to live it down! Susan knew she had control of me now. "Well than, show me your clothes and other things you have in your collection." I did not know what she was getting at, but I went to my closet and pulled out 3 blouses and 2 mini skirts that I had bought. She than instructed me to show her the lingerie that I had. I pulled out the panties, bras, slips, pantyhose, and thigh high stockings that I had. "What a nice collection you have here" she smirked. "I want you to change your clothes and put on the outfit that I chose." She went over to the bed and held up a blue jean mini skirt that have the zippers on both sides. She selected a white sheer blouse and told me to leave on the bra I had. She than laid out a pair of black silk panties with dark tan pantyhose. As I undid my mini skirt and slid it down my legs, I could not help but realize that my clitty was very hard and causing my panties and hose to bulge out. I slid out of my panties and hose letting my hard clitty free. Susan told me to put on the other panties and pantyhose and try to control myself. I pulled the hose on and than the panties, tucking my hard clitty into my panties. I took off my blouse and put on the white sheer blouse. "I like the way I can see your bra and nipples thru the blouse" Susan said. "I think that looks good, now put on the skirt." I pulled the jean skirt on and zipped the zippers down to the bottom of the skirt. Susan said "Come over here so I can adjust the zippers." I moved over to her and she took the zippers and slid them up almost halfway. This was more than I wanted but as I tried to slide them down a little, she slapped my hands and said "you do not want me to go to your mother." She told me to get some shoes on and asked if I had a purse. I went and got a pair of short heels and a small purse that I had gotten. Susan looked me over and said that she thought I could pass for a woman as long as I did not get overly excited. I did not understand until she shocked me with what was next. "Make sure you have money or a credit card cause we are going shopping" Susan exclaimed. I about died. I had been out but only in a care or park where there were not really any people. I tried to talk her out of it but she told me we could drive to my mothers if I would prefer. Off to the stores we went. As we parked at the mall, I was petrified to get out of the car. With the zippers half way up my already short skirt, one could see the top part of my pantyhose and almost my panties! I tried to pull the zippers down but was told if I did this again, she was going to unzip them more! Walking towards the mall, I was accutely aware of anybody in the area that was looking at me. I noticed a couple of guys eyeing me up. This caused my clitty to have some feelings. Entering the mall, we went to a lingerie store. "You are going to get some things and also buy me some panties to replace the ones you took" Susan said with a smile. Going in the store, Susan picked out various panties and several sets of bras and panties for me. I was squirming as I was again getting extremely excited. Susan noticed this and directed me to the fitting rooms. As we went into the fitting room, Susan walked up and pushed my mini skirt up and started rubbing my clitty thru my pantyhose and panties. "You want to *** baby, you want to get your panties all wet?" Susan asked. My clitty was so hard it was hard for me to answer. I nodded as she continued to rub me. Moving behind me, she ordered me to pull my panties and hose down over my ***. "Lean over the chair" she ordered. As I did this, I did not notice Susan go to her purse and pull out a 8" ***** with a harness. Putting on the strap on, she moved up behind me. She told me to play with my clitty as she rubbed the tip of the ***** on my ***. I felt shocked but terribly excited as she started pushing the tip of it into my ***. "No lubricant for you ****" she said. She continued to work it in and out as i freed my clitty and started ******* it. Susan had over half of the ***** into me as she pushed in and out. "I want you to *** in your panties when you are ready. I want you to feel the wetness and have to wear them wet!" Susan ordered. I continued ******* and moaning. I told Susan I was going to shoot soon. She pounded my *** with the ***** pushing in and out. "Shoot in you panties, I want to see the *** in them" she cried. Tucking my clitty into my panties, I rubbed it from the outside and soon shot gobs of *** into my panties. "Ooohhhh I am shooting" was all I could say as I exploded into my panties. As I rubbed the *** it ran into my panties and pantyhose. Pulling out of me, Susan asked "Now how was that ****?" I whispered that I had never *** so hard in my life. Susan told me to pull my self together and than meet her at the register. I straightened my wet panties and hose than my skirt. Checking my hair, I went to the check-out and paid for the items we bought. As we rode back from the mall, Susan told me that there would be many fun experiences as long as I obeyed her and did everything she said. I told her I would. We stayed together about 2 more years and had all kinds of adventures with men and women. I enjoyed it all and became even more feminine over time. Christy
nolinchris nolinchris
36-40, M
2 Responses Jul 27, 2010

I wet myself just imaging I was you!

Hey Helena,
Wish I was there to help!!


Glad you enjoyed! It was quite a time!!