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. asyalı porno 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.
I had to put my head back while she powdered my face. Then she did my eye makeup. I did enjoy it when she did my eye-liner. Just a black line just above my eye. It felt so cold at first.
Alison said, “Before we go for dinner, we need to name you. You shall be called ‘Sarah’.” I kind of liked the name, it suited me. It means princess in Hebrew.
We had a light dinner, her treat. The Maître d’ treated us as just two girls castajans porno out for a meal together. We sat and chatted. I admit it felt exciting and sexy being in a restaurant dressed as a girl. People passed by and took me for granted. I had an erection the whole time. I was in a dress, out with people seeing me.
I had trouble maintaining our conversation. I was so confused. I was dressed as a girl, I looked like a girl, and I was being treated like a girl. I loved it. My every sense was on fire. I could feel the dress against my legs; the lace of the panties around my cock, my bra across my chest. My senses were on fire. I had to be careful only to dab my lips and not to wipe them. I ‘didn’t want to smear my lipstick.
It was such a surrealistic experience. I got lost in my thoughts more than once. I was a girl. I was Sarah and loved it.
When I had to go to the restroom, Alison took my arm and led me to the Women’s room. We went in together. It was decorated in cool pink with real flowers beside the sinks; so different from a Men’s room. I took a stall and realized that I would have to sit down to pee or it would make too much noise.
We paid up and headed back to her place. She wanted me to model the other new clothes for her. I had to put on each pair of panties and bra right in front of her. He made me show her my cock and laughed that there was no doubt that I found being a girl very stimulating.
My wife travels a lot on business and so I started spending a lot of time with Alison. I had to bring new dresses with me and model for her. She said that there is something uniquely virile about a masculine, strong, Alpha Male in delicate lingerie. She liked me in softer pastel colors and flowery patterns.
I acquired quite a collection of panties and bras. A couple of feet in her wardrobe was taken up with my skirts and dresses. Each time I had to pick them out for myself and ask the assistant if I could try them on. It was so exciting going to a new lingerie store or dress shop that she had found, knowing what she would make me do. I become quite comfortable shopping for lingerie, dresses and skirts even if I was alone.
She even watched me masturbate. She whispered tender words of encouragement. She made me lay back to masturbate, just like a girl. I had to lift up my dress or skirt, slip my panties down and lay back to rub my cock. She loved to watch every stroke. She could always tell when I was about to cum. I would shoot cum all over my stomach.
She said that her hardest task was to re-teach me how to masturbate. She told me that, “Pretty girls do not just ‘jerk off’.” Girls do not stroke and pump savagely at their pussies. She instructed me how to touch it gently and prolong the ejaculation. An abundant flow of pre-cum does wonders. I used one finger to gently and slowly slide over and over it in smaller circles and larger circles. I slid my hand down and back up: slowly and gently, no rush, no hurry and gently. It was OK to ejaculate; it’s perfectly OK to let her watch.
She taught me to dress up really pretty in a dress with panties and a bra. Sometimes I wore a delicate bow around my penis. She taught me how to do my make-up and make my hair as girly as possible.
We had a separate email account for communicating. She called me, “My Sissy!”
One day I arrived to find her wearing a short red pleated school girl skirt and a white blouse tied in a knot on the left. My wife would never have worn anything so naughty and provocative. She told me to come upstairs with her. She had a surprise for me. I followed behind her and I am sure she let her panties show at every step.
In her bedroom, laid on the bed, was a sheer lacy red teddy nightie, she told me to strip and put it on. I did. She looked at me and smiled. She said, “I want to make love to a girl, Sarah.”
I was so excited to try on the teddy, I raced to take my clothes of. By now, it was quite normal to be naked in front of her. I felt an odd feeling putting on the teddy. It was so short and looked so naughty. I loved the feel around my thighs and it did nothing to hid my erection. I had come so far, now, I wanted bangbros porno to be a naughty sissy lover.
I moved forward and we kissed deeply and with passion for the first time; before, it had been more of a friend’s kiss. Now, I had become a girl kissing her lesbian lover. Deep passionate tongue kissing. Two naughty girls wrapped up together. I lifted up her skirt and felt her butt through her panties. A pair I had probably worn before.
She said that she loved seeing and feeling my pussy through my thin nighty. They made my cock feel so naughty; a man’s cock in a frilly girls nighty. It was such an electric feeling. It was like the first time I had regular sex. I could hardly think of anything else but that I was a girl.
We kissed as we fell back on the bed. I could feel her hands going down my back and feeling my butt. I pressed my cock against her pussy as we kissed and cuddled. It was so erotic knowing that I had previously worn those very same panties.
I didn’t feel that I was being unfaithful to my wife. It was a girl having sex with her lesbian lover. My wife was just a vague memory at that point. When I was with Alison, I became Sarah.
I pressed my cock against her pussy as we kissed. There was just a wisp of lace between us. I slid my hands inside her panties and squeezed her butt. I pulled away from her just a little and smiled at her. We both knew where we were heading and we were both happy with it but in no rush to get there. We wanted to enjoy every moment.
I moved my hand round to the front of her panties and rubbed her mound. She moaned as we kissed again and pressed together. I undid the side knot on her top and pulled her blouse off. Her bra was so thin I could see her nipples pressed against the lace. I reached behind her back and unclipped it.
She smiled at me and it was her turn to pull away. She put her arm across her crest and looked at me with a naughty grim. She let her arm drop and her bra fell away reveling her breasts. They were so cute, pert little B cup; with lovely little nipples sticking up at me.
She slid her hand around to my front and gently squeezed my cock. She whispered, “I love a hard cock in sissy girls cloths. Do you like the feel of lace against your big hard erection? You sissy girl you, I know you do.”
I did love this new found feeling. Wearing girls clothes had become part of me. When I dressed as Sarah, I became a different person. She gave me the freedom to become a whole new person; a clean start. Sarah was now part of me. She was always sleeping in the background as I went around as a guy. I would never be the same again. I am now part girl.
I so wanted to slide my hand back inside her panties and I know she knew that was what I wanted. She looked at me and waited. She moaned as a rubbed her pussy. She was already really wet. I dipped a finger inside her and then slipped it into my mouth. She took my cock in her hand and gave it a squeeze and started rubbing my erection.
We kissed again. My tongue mimicked what my cock was about to do to her. We knew what was about to happen and the anticipation made us both so hot. She held my cock as we kissed again. I pulled her panties down. I positioned the head of my cock against her pussy lips and stared at her as I slipped inside.
It felt like sliding into a warm welcoming cave as I went deep. Her pussy clenched around me and made me shake. I was a girl having sex with her lesbian lover. We shifted around and she sat up on top of me; her full weight pressing down on me; sitting on my pubic bone. She was taking my cock deep inside her. I put my hands up to fondle her breasts. I love cute little breasts with pert little nipples.
She sat on top of me clinching her pussy muscle around my cock. I put my hands on her hips and pulled her hard down on me. She threw her head back and let her hair hang down her back as we fucked together. I knew I was going to cum soon and so I moved her around and lay on top of her.
It was my turn to push deep as we both felt our climaxes coming. We came together. Her pussy gripped my cock as I filled it with my cum. I pressed down on her as the last pulses of my cock teased her pussy. We fell sideways in each other’s arms, kissed and just held each other.
I now live a double life. Every few days I become Sarah and make love with my lesbian lover. I become a new person when I become Sarah. She had become my second self. I am proud to be Sarah.