I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me.
I used to play gender swap cross dress role play with my ex boyfriend.
It started one afternoon when he came back from playing basketball. I had just finished painting my nails and was on the sofa letting them dry. He took off his sneakers and lay on the sofa with his feet in my lap. I took his sock off and massaged his foot and he soon fell asleep. I took his other sock- he had very pretty feet - so I painted his toenails pink like mine while he was napping. Then I moved his feet and went into the kitchen to start dinner.
When he woke up he yelled “What did you do?"
I went into the living room and he was lying there looking at his toes. I told him that he had such pretty feet, they could pass for a girl's feet; he is very competitive by nature so I added “Your feet are prettier than mine I bet in high heels people would think yours were prettier."
Seeing that he was flattered I quickly went to the bedroom and came back with some high heeled sandals and stockings. He tried to put the shoes on but they were a little too small for him, so I gave him the stockings to wear so the sandals would slide on easier.
I helped him to learn to walk in high heels; you know how it is different the first time. He walked back and forth across the living room, then went into the bedroom and was standing in front of the mirror door looking at his feet and legs and was admiring them. I told him he had better legs than most women and he laughed but seemed proud. Then I told him that if it was not for the little bit of hair on his legs, they would be prettier than most women. It was cute to see him in his basketball clothes with stockings and high heels, but I said "In for a penny, in for a pound" and took a short sundress out of my closet and coaxed him into taking off his shorts and tee shirt to wear it.
He looked very cute in it but his boxer shorts hung a little low and you could see the pattern through the white dress, so I reached under his dress and slipped them off then gave him some pretty white panties to wear. I knelt in front of him and he leaned on my shoulder as I helped him into the panties and slide them up his legs. He was getting a little erect so I kissed his cock and tucked him into the panties.
We stood in front of the mirror for quite a while and I saw that he was impressed with how he looked. I said that now that he looked like such a sexy girl he should help me with dinner, so I took his hand and led him to the kitchen. He was still a little unsteady so he had to lean on me (I have to admit I liked him being a bit vulnerable and depending on me). I need to tell you that he had never helped with cooking or house chores before that. While he was setting the table, I changed into a pair of his jeans and a shirt of his. We had a great dinner and I called him 'Wife' and he would call me 'Husband Dear'.
After dinner I said that the wife should do the dishes and was surprised when he did. We spent the rest of the evening role playing like that. When it came time for bed, he went to shower and brought his boxers and tee shirt into the bathroom, I went into the bathroom as he came out of the shower and handed him a nightgown with matching panties and told him that since he had been such a good wife all evening and made such a nice dinner I wanted to reward him. I kissed him very hard in a dominant way and played with his nipples and said "Please be my wife for the night."
I lay in the bed waiting for him and it took him a long time to come out of the bathroom, but when he did he looked so shy and sweet in his pink nightie, panties and painted toes that I got immediately turned on. He walked around to my side of the bed and lay down on his back in a female position. I leaned forward and kissed him firmly but gently and I heard him moan a little bit, so I tenderly played with his nipple as he arched his body toward me and moaned louder. He made what I could only call a whimpering sound as I slid my hand inside his panties and took his hard cock in my hand. He whimpered a little louder in a submissive way.
“You like being my girl don’t you?” I asked him.
“Uh Huh” he replied.
“You have to say that you like being my girl” I told him.
“Yes, I like being your girl” he replied.
To reward him, I slid his panties off and took his cock into my mouth. I knew that he liked to receive oral sex, so I sucked on his cock for a while and when he started to moan and squirm, I knew he was about to cum so I slowed down and worked my way to his legs and feet. I kissed each of his painted toes as we wriggled and squirmed, then I kissed his feet, ankles and calves; it was then that I noticed that he had shaved his legs while he was in the shower. They were so silky and smooth and I could smell the faint aroma of my lotion on his legs.
I was so turned on by the fact that he had shaved his legs that I immediately went back to his cock and took it in my mouth and sucked it as I played with his nipple with one hand. He was ready to cum and he was squirming while making those half moan/half whimper sounds. He tried to push me away, but I held both of his hands and pinned them to the bed as my head went up and down in his cock. I knew he was trying to hold back, but he couldn't any longer and I felt his body spasm under me while he shot his load into my mouth. He always ejaculated a good volume, but it seemed like it was 3 or 4 times as much. I gladly took all of it and swallowed his juice. He was still shaking from the orgasm while I spooned him from behind and kissed the back of his neck and told him he was my ‘good girl’
After sex, he is pretty much done for the night and falls asleep, but he surprised me by rolling over and kissing me passionately then going down on me. He had never offered to have oral on me, so I was surprised with what vigor and skill he parted my labia and found my clitoris. He was so passionate, sensitive, and sensual that night, we had always had good sex before that, but that night and ever after it was different and really great.
Later that week, he went shopping after work and bought new boxers and tee shirts on sale at Nordstrom. That night he told me that they were too small for him but he could not return them because he had opened the packages. I went into the bathroom to try them on and they fitted me perfectly. When I came out in my boxers and wife beaters, he was lying on the bed in the pink nightgown. After that, he always wore nightgowns to bed and I always wore boxers or briefs…..
Sometimes I would dress him as a girl all weekend for 24 hours a day and he would cook and clean while I washed the cars and did other things around the house. After a while he did not want me to paint his toenails anymore (he used to wear pink or red nail polish all week under his regular socks). One night after sex he started to cry and he said he did not want to dress up anymore because it was confusing. I should have listened to him better but I was selfish and got him aroused again and asked him to promise to be my girl for always. He was very horny and promised and we had great sex, then I held him while he slept in my arms and stopped crying. I thought that we were back to 'normal' then I found out that he was sleeping with other women to re assert his masculinity and he was seriously involved with one of them.
We broke up and a short time later I heard that he had married a woman who owns a local gym in town. She used to be a professional body builder and is very muscular and somewhat mannish. She usually dresses in gym clothes or men’s style clothing and is sometimes mistaken for a man from behind. I ran into my ex about a year after they were married; he was at the mall coming out of Victoria’s secret with a big bag of purchases. I hope that they are happy.
Since then I have met and feminized a few men, and can share those stories if you like.
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<a href="http://www.lushstories.com/stories/crossdressing/crossdressing-fun-from-a-womans-point-2.aspx">Crossdressing Fun From A Woman's Point of View</a>