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From Kyle to Kyla

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Kyle gets caught by an angry girlfriend.
1.7k words
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It was Sunday afternoon, and I was staying at my girlfriend's apartment. She had asked me to stay there to spend the week-end to take care of her fishes while she was away. We've only been dating for about 3 months at the time and she had no idea of my crossdressing ways.

Of course I went through her clothes. I had on a black thong and a matching bra. I was taking a nap in her bed when I got woken up by a screaming girlfriend.

"WHAT ARE YOU DOING?"

I jumped out of bed and realized I had just been caught. There I was, in my bra and panty. She was supposed to be back Monday morning. I was about to ask her why she was home early but she cut me off.

"Get out, get out, get out!"

"Let me explain." I pleaded.

She left the room and I chased after her. We were at the entrance when I told her "I'm really sorry, let's talk about it please."

"There's nothing to talk about...now get out" She opened the door holding it open.

"Let me get my clothes"

She went in her room, grab my clothes and tossed them out the window. Her apartment was on the 12th floor. She came back with a sense of satisfaction. "Go find your clothes, now GET OUT! As she physically pushed me out and slammed the door.

I didn't know what to do. I was in the hallway in a bra and thong and just stood there. I had always fantasized about getting caught but not like this. In my fantasies I would be all done up with makeup, wig and a nice dress. I would get caught by my girlfriend or a good looking guy: and they would definitely not be upset.

I heard the elevator door opened. My heart stopped and I froze. A beautiful brunette walked out and was walking towards me looking in her purse for her keys; I suppose. She stopped abruptly when she saw me.

"Fun night?" She said jokingly.

I told her what had just happened. I felt so stupid saying it. She was listening attentively and I didn't feel like she was judging me.

"Why don't you come over, my boyfriend could lend you some clothes."

I felt so relieved that I didn't have to go down 12 flights of stairs dressed like this. Her apartment was only 3 doors down from my girlfriend's.

"I'm Natalie by the way" and shook my hand.

"I'm kyle." I said as she opened the door.

Sitting on the couch, were three guys watching the football game with their jerseys on. They all turned their heads at the same time towards us.

It was an open concept apartment. As you walk in you can see the kitchen and living room on the left. On the right was a storage closet followed by a bathroom then the bedroom.

"Billy, can he borrow some clothes?" Natalie said pointing towards me.

"What? No...Why? Who is this?" Billy said confused.

Billy was a big man, about 6 foot 4, big shoulders and athletic. He had a deep voice that commanded attention.

"Well, you see...long story short, he got caught wearing his gf's underwear and got kicked out." Natalie said casually.

"There's no way I'm giving my clothes to this sissy. Tell him to get out."

His friend whispered something in his ear and they laughed.

"Wait, I'll sell you my clothes sissy boi." He said grinning.

"Uhhh...I don't really have money." I said lifting my arms as in saying look at me, where would I have money

"You do what I tell you to do until the game is over. Then I'll give you some clothes.

"Babe, stop it. Let him be and his name is Kyle." It felt nice that Natalie was defending me. Not that it worked.

"Great, Kyla: get me a beer in the fridge." As I'm bending over to grab a beer I hear Natalie say to Billy and his friends.

"You guys are totally checking out his ass."

I smiled to myself. I was bent over and my backside was exposed. I took my time to grab the beers and slightly arched my back. I brought them their beers in the living room. Billy gave me a slap on the ass as I walked by, making me jump a little. Natalie saw my smile and smiled back. She realized I was enjoying it.

"Hey guys, I bet Kyle would like this..." Natalie said going in her room.

After 2 minutes she came back with a long blond wig, some black thigh highs and a miniskirt. She placed the wig on me and handed me the rest. I really enjoyed the attention I was getting and gladly went in the bathroom to get dressed. It was a really short skirt that you could see my lower but cheeks. I was looking in the mirror when Billy and Natalie walked in. He eyed me from head to toe then unzipped his jeans. He took out his cock and started peeing in the toilet. I couldn't help but look at his massive cock from the corner of my eye.

"Like what you see dear?" Natalie said as she noticed me looking

"Umm...I guess"

"You guess? Take a closer look." Billy said pointing his cock towards me when he finished peing. I just smiled at him.

"Well...what are you waiting for? Get down on your knees. Get a closer look." Natalie said.

I did as commanded and was now on my knees in front of this tower of a man. Natalie grabbed his cock in her hand and started stroking it. She grabbed the back of my head with her other hand and pushed me on his cock.

"Come on baby, open up" She said slapping his dick across my face.

I opened my mouth and let her guide his cock inside. He got rock hard almost instantly. He started thrusting in my mouth as Natalie was pushing me deeper and deeper at the same time. I had to push him off briefly to catch a breath before he shoved it back in. I happily sucked him off. Saliva started dripping at the side of my mouth and I could tell he was about to cum.

"Oh fuck...your such a good little cocksucking bitch" Billy pulled out and started stroking his cock fast. Natalie held my head with both hands from behind me.

"Open your mouth." Billy commanded as he started cumming.

The first and second stream hit my forehead. The next two hit both my cheeks then he finished off in my mouth. I think he wanted to make sure my face was covered in cum and boy was it ever.

Billy zipped up his jeans and told me to stay put and not to wipe my face. He and Natalie both left the bathroom. I heard Billy say in a loud voice.

"Hey guys go check out the sissy in the bathroom. She's all yours."

I was standing in front of the mirror looking at my cum covered face. The two guys came in and laughed.

"You're a cum slut aren't you."

They both stripped naked and started groping my ass and sliding their hands on my thighs. I looked very sexy in a skirt and by the hard cocks they had, they felt the same way.

One of the guy pulled my panty down to my ankles. He spit in his hand and rubbed it over my asshole. He inserted a finger and then two. He fingered me for a bit then I felt the head of his cock push at my entrance. I let out a soft "Ouch" as his cock was stretching my ass.

"Shut up slut...you know you want it." He kept pushing it in until all 7 inches were inside me. I turned my head around to look.

"Don't look at me slut. Turn around" I turned back around and looked in the mirror again.

I had my elbows on the counter looking at my face dripping cum from my chin. I could see the guy fucking my ass from behind. The other one was watching and stroking himself. From time to time he would slap my ass saying naughty things to me.

After a while he finally came filling my ass with his cum. It felt amazing, I didn't want it to stop. He pulled out and I felt the emptiness in my ass. I wanted more. He sat down on the toilet seat and ordered me to clean his cock.

I got on all fours and licked him clean as the other guy mounted me doggy style. I could feel the cum dripping down my thigh and the cum on my face was starting to dry. After I cleaned off the guy on the toilet he left

"It's just you and me now slut." said the guy pounding my ass.

He was fucking me so hard I had to hold down on the toilet seat to hold myself. I was now rock hard and pre cum was dripping out of my cock. I was about to have my first hands free orgasm when he pulled out. A feeling of disappointment came over me. I wanted to be fucked.

"Quick turn around" He said.

So I quickly turned on back and laid on the bathroom floor. He stood up on top of me and stroked his cock till he came. I felt his cum hit my face first, then it landed on my bra and chest and the rest hit my stomach.

"Thanks slut" He said leaving satisfied.

I just laid on the bathroom floor, my whole body covered in cum. I grabbed a bit of cum on my stomach and started stroking my cock with it. Within minutes I was cumming all over myself.

Natalie came by and smiled at me. She took out her phone and took a picture of me laying there. I couldn't care less. That was the best sex I ever had and knew that my life was about to change. I wanted to become Kyla. Natalie handed me her hand and helped me up.

"You really enjoyed that it seems. I know a lot of guys that would pay too fuck a pretty girl like you. I could help you become the girl you want to be, interested?"

"Yes of course" I eagerly said with a big smile. And that was the beginning of my transformation from Kyle to Kyla.

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AnonymousAnonymousover 4 years ago

I liked it. It was pretty hot to picture myself in Kyla's positions

cdCindy1cdCindy1over 5 years ago
great first story

This is an excellent first story. Please continue and tell us all what happens with Kyla and Natalie. I'm a sissy faggot cocksucking CD and this story is exactly what I wish would happen to me. Please tell us more adventures. I can't wait.

mumblegooseeggmumblegooseeggalmost 8 years ago
Give justsomefantasies a break, guys

Who has read a story on here that isn't full of clichés? If you think you have, it's only because one person's turn-on is another's banality. I kind of liked it and would gladly read more. But then I get turned on by guys getting all sissified when they meet a hunk while they are in lingerie. Cliché? Love it!

aboychickaboychickalmost 8 years ago
Same old same old

Doesn't sound like anything new -- not that it was bad, but it wasn't quite original.

AnonymousAnonymousalmost 8 years ago
Please continue

I want to see Kyla turn out to be a trophy girl imo with Billy.

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