My name is Billy, and I'm twenty-six. I have black hair, and brown eyes. I have a girlfriend that I've been seeing for a few years now. I should mention, that I occasionally like to dress up. I'm not talking wearing a tux, I'm talking about wearing a dress. That's right, I'm a cross dresser.
Very few people know about it, and my girlfriend, Phebe, wasn't one of them. My mom knew, and a couple friends knew, but that was it. My friends knew, because they also had this weird fetish. We would get together every now and then, and exchange stories of what we did in dresses. That was actually how my mom found out, and she was just surprised by it. She wasn't mad though. Anyway, I frequently tried on different dresses in my room, and accessorized.
"Damn, I look good," I said to myself.
Well, I thought so anyway. I had thought of every possible way I could think of, to tell Phebe about my secret. I wasn't sure how she would take it, she could just freak out, and dump me. That not even being the worst case scenario. She could out me to a lot of people, like where I worked. I would be taking a lot of shit for that.
I knew I was going to tell her sooner or later, but I was just waiting for some magic moment. When I could tell her, and all the judgments would just not come out. I knew that was probably never gonna 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 in for a surprise.
"Billy, where are you?" Phebe called out.
I was freaked out, and moved quickly. I tried to get out of the dress, and hide it, before she got to my bedroom. I wasn't in the living room, or kitchen, so she was gonna come straight there. She heard me moving quickly, and that just made her want to come in a little quicker. So she caught me stuffing the dress in my closet. I didn't wear a bra, and panties, so I was just in my boxers.
"What are you doing?" she wondered.
"Nothing, I'm just hanging out here," I replied, casually.
"What were you putting in the closet, is it a present?" she pondered.
"Maybe, but this isn't the time I wanna give it to you. I guess you'll just have to wait," I told her.
I turned around, and started to get out some normal clothes, but she decided she wanted her surprise right then. She opened it, and saw the dress stuffed in there.
"Is this it? You got me this 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 in for a surprise, that dress was way too big for her.
"What the hell, dude? This is way too big," she said.
I didn't know what to say again, so there were only two possibilities. Either I told her the truth, or her assumptions were gonna take her in another direction.
"This is for someone else? Are you hooking up with a bigger woman?" she pondered, angrily.
I didn't want to lose her, so I took the shot in the dark.
"No, Phebe, it's mine," I said.
She gave a weird look, and was unsure what to say to that.
"What are you saying, that you wear this dress?" she wondered.
I took in a very deep breath.
"Yes," I replied.
She just grinned, it was unclear it she believed me or not. She brought it over to me, and held it right up against me.
"It's a good fit. Put it on," she ordered me.
Well, it was definitely a better choice, than the alternative. I just put on the dress in front of her. It certainly felt different then, she definitely couldn't hold in her emotions, because she just started laughing all of the sudden. She pulled out her phone, and couldn't resist, but to take a picture.
"You like wearing this dress?" she had to know.
"Yes," I replied.
She just continued to laugh for a minute, and came towards me. She put a kiss on my lips, and my cock stuck out.
"This is kinky, and I like kinky," she put on the record.
She put her arms around, and we began making out. As we were kissing each other, she began undoing her shorts. A minute later, she took off her shirt too.
"Fuck me with the dress on," she demanded.
Oddly enough, it was a weird concept. Then she took off her bra, and panties as well. So, it wasn't a fair fight. She got down on her knees, and put her hands underneath the dress. She pulled my boxers down, and grabbed onto my cock. It was still hard, but she thought I might need some help getting it up. She got underneath the dress, and gave me a blow job. I opened my mouth, and let out a big moan too.
"Oh, that's good, Phebe. I love you," I said.
She came up for a quick second.
"I love you, even if you do like wearing a dress," she replied.
She went back underneath the dress, and took my cock back into her mouth. She always gave great blow jobs, but when she did as I had a dress on, she made me wanna cum in about a second. I did my best to hold it in, but she decided to deep throat me too.
"Fuck yes, 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 told me.
She went over to the bed, and laid down. She invited me over there with her, and I got on there. I was more than amped up to fuck her, and she was really excited. All I could figure was, that she had some fetish about me fucking her in a dress. I got on top of her, and inserted my cock into her.
"Oh, why thank you, Miss Billy," she said, while snickering.
"You are funny," I replied.
I began thrusting my cock, and she really threw out the passionate moans.
"Oh, fuck yes, Billy, do it just like that," she said slowly.
I made love to her, but of course it felt weird. She put her hands under the dress, and put them onto my butt. She gently rubbed my butt cheeks, and told me loved the sight of me in a dress. I wasn't super excited about that, but it was a little nice to hear. I still enjoyed making love to the woman I loved.
"You should fuck me in this dress more often, it's hot, and kinky. I fucking love it," she moaned.
"You really think so?" I pondered.
"Fuck yes, now pound me, Billy, I want you to make my pussy sore, while you wear a dress," she replied.
I had gotten very hot, and sweaty, but I still managed to gain enough strength to pound her hard. To do so, I leaned up a little bit, and began thrusting really hard. She just got a better view from down there. She was grinning, and trying not to laugh. It seemed to be no easy task, judging by the look on her face. Even though I was pounding her, that didn't seem to distract her from what I was wearing. Then I finally got her to express her pleasurable feelings.
"Yes, even when you wear a dress, you still know how to use that cock, I fucking love you," she moaned.
"I love you too," I moaned back.
I was running out of breath, and reaching my breaking point.
"Fuck, I'm gonna cum," I said.
"Cum inside me, I want a ladies man to cum inside me," she replied.
That almost killed the mood, but I still managed to cum inside her. Soon after that, I crashed down onto her. She wrapped her arms around me, and still giggled a little bit.
"I would still love you, even if you took me out on a date in the dress," she put on the record.
"Damn, 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 had me get off her, and she got onto her knees. She didn't like to fuck doggie style, but in this case, she was gonna let me. So, I got onto my knees too, and stuck my cock right into her pussy.
I began thrusting my cock again, and she looked right back at me. She began smiling, but managed to not actually laugh though.
I put my hands onto her butt, under the dress, and caressed it. She began moaning slightly, due to me sticking in every single inch of my cock in there. We both stayed silent for the time being, and enjoyed each others company. She eventually leaned back up with me, and turned her neck. She put her lips onto mine, and put her right hand on the back of my head.
"You still wanna be a man, right?" she pondered.
"Yes," I replied, in a slight tone.
"Then cum inside me again, and get me pregnant," she demanded.
She leaned back down, and I began pounding her doggie style. That was what I liked to do, but she didn't really like it. I was gonna take advantage of this opportunity.
"Yes, pound me now, Billy, and shoot your load inside me, and give us a daughter," she demanded.
I wanted kids at some point, but she wanted them sooner than me. If she still loved me after seeing what I did when she wasn't around, then what could I say? I just wasn't going to ever mention to anyone, that we had sex when I wore a dress.
So, I put my right hand on her pussy, and the other on her left tit. We both began breathing heavily, and I knew we were going to cum together, simultaneously.
"Yes, cum with me please, Billy," she pleaded.
We both came at the same time, and it took a big toll of us. We both laid down together, and cuddled for a little while. She even held my hand, which I thought was weird.
That was at least on the top ten of best orgasms either one of us ever had. To think it happened, when I was wearing a dress. Now we fuck every now and then, when I wear it. Soon after that, she moved in with me. She doesn't like doggie style, and I don't like doing it in the dress. We both make little sacrifices now, and hope to get her pregnant soon too,.
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