I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some grammatical mistakes.
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I went over to my sister-in-law, Alison, for a casual chat and a drink. We had always got along really well. She was my wife, minus my wife's attitude towards some of my 'interests'. We sat in the living room and chatted over a glass or two of wine. Then the buzzer on her clothes dryer went off. She said, "I need to fold my clothes while they're still warm."
I followed her into the laundry room and watched while she unloaded the dryer and separated her clothes into categories and started folding them. We just chatted on. My eyes kept going to the pile of her panties waiting to be folded. They were in bright colors with lace trim and lots of bows. My wife would never have worn anything that sexy and skimpy. I started to get a strange fascination in them and realized that I was getting an erection.
I think she glanced at my crotch and had noticed where my gaze kept going. She moved to start folding her panties. She picked up a nice frilly black pair and suddenly held them out to me and said, "There, these should fit you, try them on. I can see how excited you are by sissy girls panties." She looked straight at my crutch and smiled.
I stammered and blushed but she said, "I know you want to feel how they feel against your cock. Go on and put them on." I was so embarrassed but she was right, I did want to put them on and feel my cock through them.
I took them and held the soft lace between my fingers. I was so excited but scared at the same time. I was holding a pair of frilly girls panties and my sister-in-law wanted me to put them on. I was so confused and excited at the same time. Was I really going to put them on? I went to leave but she said, "No, change here, in front of me, I want to watch you."
I was so excited about wearing her panties that I didn't care if she watched. I undid my belt and took my jeans off. I pulled down my shorts. I was very aware that she was staring at my very erect cock. I quickly slipped on her panties and put my jeans back on.
It was a wonderful feeling. Girls lace panties around my cock. It was electric. I was actually wearing a real girls panties under my jeans. I could have cum just by thinking about it. It took me a while to fully accept what was happening. I was wearing sissy panties and she knew it.
She continued to fold her clothes and we did not mention panties again. It was as if nothing special had happened. When she was done, we went back to the living room for another glass of wine. It was hard for me to maintain our conversation knowing what I had on. It was so erotic. I was wearing her panties under my jeans and pretending it was quite normal.
She said, "I need to go shopping later, can you come with me to help carry things?"
I relied with just, "Sure."
She added, "If you ever don't do what I tell you too, I'll tell my sister all about this." My sister will love to hear all about her sissy crossdressing husband. My blood froze; I realized that I was totally under her control. Somehow it was kind of exciting. I wondered what more she would make me do.
After another glass of wine, she said, "Let's go shopping."
I was still wearing her panties under my jeans and it was hard to keep my erection hidden. I was actually wearing a pair of girls panties out to the mall. I imagined that everyone could see them even though I had jeans on. It was as if everyone was staring at me.
By now, it was Saturday afternoon and the stores were full with customers. She took me into a lingerie store and started looking around. A saleslady came up to us, "May I help you, ma'am?"
Alison turned and smile sweetly, "Yes please, that would be nice. It's for him. He needs some new lingerie."
I turned beet red and started to shake and mumble and turn away. Alison put her hand on my arm to keep me in place. The saleslady was flustered. She noticed two things: the credit card in Alison's hand and that I was a guy. I guess that a sales commission trumped over social norms.
She found some nice things for me. Alison said, "Why is it that men have no idea about colors and patterns; how to select lingerie to match and complement clothes? I will have to spend time teaching you how to create matching sets, bras and panties with camisoles and dresses. It will be so much fun!! We can work on accessorizing, getting the right purse and belt for a particular outfit. Then we come to jewelry and makeup, more lessons for you. What color eye shadow works with the color of your dress and there's so much more to learn. "
She whispered to me, "If you ever disobey me, my sister will love to see your new wardrobe."
We paid up with all of the items laid out on the counter in front of us. It only added to my embarrassment but also a strange sense of excitement. I loved my new clothes. The colors and textures looked so sexy. I wanted to try them all on, my cock was hard just thinking about wearing them. Would she make me model them for her? Even more interesting, would she make me put them on right in front of her?
I let my fingers feel the lace and satin, such soft thin girls lingerie and they were mine. I knew that I would be putting them on later.
Alison said it was her treat for being a good girl. I kind of liked being called a 'girl'. It had my cock jump.
She asked the assistant where the changing room was and handed me a bra and gave me a shove. I had to carry it into the changing room and put it on.
Then, she took me to Dress Barn and made me pick-out a dress. I chose one with short puffy little sleeves in white and pink. The puffy sleeves hid some of my male shoulders. It had a straight bodice and a floral skirt that poofed out. It had petticoats underneath to make it spread out more. She made me go and try it on. I had to get the assistant to unlock the changing room door for me.
It was a wonderful feeling when I slipped it on. A girls dress just felt so electric against my skin. My panties were free to the outside under the petticoats. I was so excited and scared at the same time. I was getting electric feelings wearing a girls dress. Even the words shook me; I was wearing girls panties and bra under a girls dress.
After she paid for my new dress, she said, "Go and put it on." I had to take it back into the changing room and slipped it back on. I was surprised; it felt wonderful. The dress slipped down my body as I pulled it on and I loved the way the skirt swished against my legs. I tried sitting down and it was wonderful to feel the petticoat against my thighs. At least it hid my erection.
Later, as we walked around the mall, the petticoats brushed against my legs. I admit it was a wonderful feeling. I could feel the air conditioning blowing under my dress against her panties.
Before we went for dinner, she looked at me and said, "We had better do something about your face." She took me to a makeover section in a store. If you bought $60 worth of their make-up, they would give you a free make-over. I had to sit there on the high salon chair while my makeup was done. Shoppers were walking by and glanced at me but no one seemed to care. Not only was I wearing a dress but getting my makeup done too. I still love getting my make-up done in stores.
I asked the make-up artist is she had ever done a guy before? She said that doing a male-to-female make-up is a lesson in 'beauty school'. Since then, I've had my make-up done professionally several times.