Crossdressers make better husbands
My girlfriend caught me in a dress
A guy who likes to wear a dress gets caught ...🕑 10 Minutes Crossdressing Stories
My name is Billy and I'm twenty six. I have black hair and brown eyes. I have a girlfriend who I've been seeing for a couple of years.
I should mention that I like to get dressed every now and then. I'm not talking in a tuxedo, I'm talking about wearing a dress. That's right, I am a crossdresser. Very few people know about it, and my friend Phebe was not one of them.
My mom knew and a couple of friends knew, but it was. My friends knew because they had this weird fetish too. Every now and then we would meet and share stories about what we did in clothes. My mother found out and she was just surprised. But she wasn't angry.
However, I would often try on different clothes and add accessories in my room. "Damn it, I look good," I said to myself. Well, I thought anyway.
I had thought of every possible way to tell Phebe my secret. I wasn't sure how she was going to take it, she could just freak out and let me fall. That's not even the worst case scenario. She could put me out to a lot of people, like the place where I worked.
I would take a lot of shit for that. I knew I would tell her sooner or later, but I was just waiting for a magical moment. If I could tell her and all the judgments just wouldn't come out. I knew that would probably never happen, but unfortunately the moment was chosen for me.
I was in my apartment and Phebe had a key. So she just came in and she was ready for a surprise. "Billy, where are you?" Exclaimed Phebe. I was freaking out and moving fast.
I tried to get out of the dress and hide it before she got into my bedroom. I wasn't in the living room or the kitchen, so she was about to be there. She heard me moving fast and that made her come in a little faster.
So she caught me stuffing the dress in my closet. I wasn't wearing a bra or panties so I was just in my boxer shorts. "What are you doing now?" She wondered.
"Nothing, I'm just hanging out here," I replied casually. "What did you put in the closet, is it a present?" she considered. "Maybe, but this is not the time I want to give you. I think you just have to wait," I told her.
I turned and started taking off normal clothes, but she decided she wanted her surprise right away. She opened it and saw the dress tucked into it. "Is that it? Did you get me that big dress?" She wondered. I just didn't know what to say and she assumed it was for her. She immediately took off her shirt and shorts and tried it on.
She was surprised, this dress was way too big for her. "What the hell dude? It's way too big," she said. I didn't know what to say again so there were only two options. Either I was telling her the truth or her assumptions would lead her in a different direction. "This is for someone else? Are you joining a bigger woman?" she thought angrily.
I didn't want to lose her so I shot in the dark. "No, Phebe, it's mine," I said. She gave a funny look and wasn't sure what to say about it.
"What do you say you are wearing this dress?" She wondered. I took a deep breath. "Yes," I replied. She just grinned, it was unclear whether she believed me or not. She brought it to me and held it right against me.
"It fits nicely. Put it on," she commanded me. Well it was definitely a better choice than the alternative.
I just put the dress on in front of her. It definitely felt different back then, she definitely couldn't hold onto her feelings because she suddenly started laughing. She pulled out her cell phone and couldn't resist but to snap a picture.
"Do you like wearing this dress?" she had to know. "Yes," I replied. She laughed just another minute and came up to me. She kissed me on the lips and my cock stuck out. "This is perverted and I like perverted," she put on the record.
She put her arms around her and we began to loll. While we were kissing, she began to undo her shorts. A minute later she took off her shirt too.
"Fuck me with the dress," she demanded. Oddly enough, it was a strange concept. Then she took off her bra and panties.
So it wasn't a fair fight. She knelt and put her hands under the dress. She pulled my boxers down and grabbed my cock.
It was still hard, but she thought I might need some help building it up. She got under the dress and gave me a blowjob. I opened my mouth and groaned too. "Oh, that's good, Phebe.
I love you, "I said. She came up for a brief second." I love you, even if you like to wear a dress, "she replied.
She went back under the dress and took my cock back into her mouth. She always gave great blowjobs but when she did when I was wearing a dress she made me cum in about a second. I did my best to hold onto it, but she decided to force my throat deep as well. "Shit yeah, Phebe," I muttered.
Then she came out and moved the dress. "Well your cock is pretty hard now so I think you should fuck me now," she said to me. She went to the bed and lay down. She invited me there with her and I got on there. I was more than overwhelmed to fuck her and she was really excited.
I could only imagine that if I fucked her in a dress she would have a fetish. I got on top of her and stuck my cock inside her. "Oh why thank you, Miss Billy," she said, giggling.
"You're funny," I replied. I started thrusting my cock and she really threw out the passionate moans. "Oh damn it Billy, just do it like that," she said slowly.
I slept with her, but of course it felt weird. She put her hands under the dress and put them on my bum. She gently rubbed my buttocks cheeks and told me that she loved the sight of me in a dress.
I wasn't particularly excited about it, but it was a bit nice to hear. I still loved sleeping with the woman I loved. "You should fuck me more often in this dress, it's hot and dirty. I fucking love it," she moaned. "Do you really believe?" I thought about.
"Damn it, now hit me Billy, I want you to sore my pussy while wearing a dress," she replied. I got very hot and sweaty, but I still managed to gain enough strength to hit her hard. To do this, I leaned forward a little and started thrusting really hard.
She's got a better view from down there right now. She grinned and tried not to laugh. It didn't seem like an easy task considering the look on her face. Even though I hit her, it didn't seem to distract her from what I was wearing.
Then I finally got her to express her pleasant feelings. "Yeah, even if you wear a dress you still know how to use that dick, I love you damn it," she moaned. "I love you too," I moaned back. I ran out of breath and reached my breaking point.
"Shit, I'm coming," I said. "Come inside of me, I want a woman's man to come inside of me," she replied. That almost destroyed the mood, but I still managed to cum inside her. Soon after, I pounced on her.
She wrapped her arms around me and still giggled a little. "I would still love you even if you took me on a date in my dress," she put on the record. "Damn it, you couldn't stop laughing to save your life," I told her.
"I'm sorry, but let me make it up to you," she let me know. She let me get off her and got on her knees. She didn't like fucking like a dog, but in this case she let me.
So I got on my knees too and stuck my cock straight into her pussy. I started poking my cock again and she was looking straight at me. She started smiling but couldn't really laugh. I put my hands under the dress on her bum and stroked it. She started moaning slightly as I tucked every inch of my cock into it.
We were both silent for the time being and enjoyed each other's company. She finally leaned back over to me and twisted her neck. She put her lips on mine and put her right hand on the back of my head. "You still want to be a man, don't you?" she considered. "Yes," I answered quietly.
"Then come back inside and make me pregnant," she demanded. She leaned back and I started pounding her dog style. That was what I liked to do, but she didn't really like it.
I wanted to take this opportunity. "Yeah, hit me now, Billy, and shoot your load inside me and give us a daughter," she demanded. I wanted children at some point, but she wanted them sooner than I did. If she still loved me after seeing what I did when she wasn't there, what could I say? I didn't mean to tell anyone that we had sex when I was wearing a dress.
So I put my right hand on her pussy and the other on her left tit. We both started breathing hard and I knew we were going to cum at the same time. "Yes, please come with me, Billy," she pleaded. We both came at the same time and it took a huge toll on us.
We both lay down and cuddled for a while. She even held my hand, which I found strange. That was at least one of the ten best orgasms any of us have ever had.
To think it happened when I was wearing a dress. Now we fuck every now and then when I wear it. Shortly afterwards she moved in with me. She doesn't like dog style and I don't like in dress.
We are both making small sacrifices now and hope that she will get pregnant soon too; ..
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