Erotic fiction and short sex stories

New stories daily




Kylie Wakes Up Ch. 01

I want to tell you all how I became the Cross-dressing slut I am today. My name is Kylie, and these stories are all true.

I could tell you the same stuff all cross dressers seem to say, how I dressed in my mothers lingerie when I was young. How I hid it even from myself throughout high school. How Kylie's voice grew in my head till I couldn't take it anymore and had to try getting fucked. The first time a man took me I was 20. I met him on a website and went to a dirty hotel and had his cock fuck my tight virgin hole. It freaked me out after and I swore off cock forever.

"You liked it though" I heard in my head.

"You want more." The voice was so like my own but slower and softer. It would grow quiet for weeks then come back loud and demanding, "Go online...find more cock. I need it, you need it."

I fought and fought. I tried to convince myself that it was from watching too much porn. I didn't really have these desires, I was confused is all. That all changed when I met Joe.

Joe was my age. He responded to an ad I had placed on a cruising site. I told him like I'm about to tell you that I am fat. I'm 5'8 and over 300 pounds. My ass is huge. He liked that, he told me he wanted to see me bent over in his bed with my fat ass in his face. He wanted to rim me and fuck me till I came.

Since that is exactly what I was looking for, I agreed to meet. I still wasn't ready for someone to see me in my lady clothes. I went to his place as my normal self. On the way there I switched the radio in my car to pop music, something I never listened to normally. As I drove, I began to feel like someone else, something other than who I am 9-5 during the week.

I felt a shaking in my stomach. It had been two years since that disgusting hotel, where a man I hadn't really liked had deflowered my hole. Two years since I had really given in to that voice, the one that sounded like me but didn't.

She was back now, whispering about great it will be when he's inside me. How the taste of his cock will finally set her free. An old Britney tune came on the radio and I heard her say to me, "let me take over tonight, I know what you need more than you do. I can make this night great."

After driving for half an hour with voices arguing in my head, I pulled up to the building that Joe lived in. It was a standard bungalow with a buzzer on the front door. I paused before hitting the button. I knew this was my last chance to back out. If I hit the buzzer I was committed to becoming his bottom for the night.

"Push IT" I heard.

"You want this; it's why you drove here. If you leave you'll be back cruising sites for dirty talk. Sitting alone reading stories instead of living them". My hand stayed at my side. "Push IT NOW" the voice now demanding I take the final step.

Slowly my hand rose to the list of names next to the small round buttons that seemed so much larger than they had before. I pushed Joe's buzzer. A minute later a voice with that speaker twinge said "Kyle?"

I tried to speak but instead my voice caught in my throat and I coughed to get it back. With a mighty effort I replied "Yes".

"2A" The voice said back.

I grabbed the door handle as it buzzed and took a fatal step inside. The Door slammed behind me as I let it go. Chicago doors tend to be heavy to keep out the cold and this one did not disappoint. What sounded like a bomb went off behind me and I jumped, realizing what had happened I made my way up the stairs to door 2A. I didn't have to knock; he must have been standing right behind the door because it opened as I reached his mat.

The man standing there was gorgeous; there is no other way to say it. Even now as experienced as I am as bottom slut, I don't often find men overtly attractive. I find women beautiful and sexy. With most men all I want to know is how well they can fuck. Joe is one of the few that I have looked at thought about how good the look. His body was lean and cut, his biceps had a nice definition but not in an overworked way. His face was sweet and honest with a pair of small glasses that made me think college student right away.

I immediately expected him to throw me out. Here I am a fat little troll and there is this Greek statue of a man who clearly could have any one he wanted, Man or woman. Waving me in without speaking he glanced around the stairway and shut the apartment behind me.

The main room was sparsely decorated with a small tube TV and a black love seat. It looked a lot like many of my friend's places throughout the city. The familiar setting both relaxed and unnerved me. I hadn't really thought much about it, but I think a small part of me was expecting this guy to be a serial killer. The familiar layout seemed to relieve me of that concern. I was also feeling a little strange because I had come here to do a secret thing, but couldn't help but think of my friends and what they were up to. This was the last thing I wanted in my head. I already felt dirty and guilty enough without having to think of my real life.

"Would like a drink?" Joe asked. I had been in my head so deep in thought his question startled me.

"I'll take a beer if you've got it"

"One minute, please sit down."

I sat on his black IKEA love seat. Still expecting to be thrown out on my fat ass by this hot man who clearly shouldn't have a problem getting laid, and wouldn't want a slob like me.

"Relax" she whispered. "He smiled when you came in. He's as nervous as you are. Look at his hands trying to open that bottle."

She was right; His hands were shaking slightly as he returned from the kitchen. He handed me the beer and sat down. We were next to each other like that for a long time watching some realty show on TV not speaking or moving, except when my arm brought the cold beer to my lips.

"So..This is awkward" I said.

"I know." Joe returned. "I've never done this before, Have you?"

"Once, a couple years ago."

"What was that like?"

"He was a little older so he kind of took control." I was speaking softly now, trying to calm myself down.

"Ah."

He looked at me in the eyes for a few seconds then grabbed my hand and pulled me in to a kiss. I know story tellers like to talk about fireworks and lightning when two people kiss, that didn't happen to me then. When he first pressed his lips to mine I was so shocked by the intimacy of it I didn't feel anything. When I felt his hand on the back of my head I swooned. When his fingers played with the little hairs on the small of my neck I felt a wave of pleasure roll through me and I pressed myself to him.

His hands found the bottom of my shirt and pulled it over my head. I tried to cover my belly with my hands and he very sweetly moved them and kissed my stomach just under my belly button. When that happened I became an animal, I pulled his shirt off and wrapped my arms around him. I kissed and sucked his neck moved my way up his ears then around to his cheek, he turned and jammed his tongue down my throat. I sucked on it like it held the antidote to poison that was turning my body loose.

'Go to his bed' She said. 'Suck his cock'

Joe was kissing my neck as I began to stand up. At first I think he thought I was running out because the look on his face was one of total confusion. I smiled at him as demurely as I could, and slowly slid my jeans off in one move. Once I kicked them off I grabbed his hand brought him to his feet. We kissed as we walked to bedroom. Almost falling over twice, but we couldn't stop.

I felt the bed before I saw it. It bumped against my legs and I sank down. I used my hands to tell Joe to keep standing and undid his belt. All these years later and that is still my favorite moment of foreplay. Sissies Sluts like me I'm sure understand this, when you begin to undo a belt it gives you feeling of both control and submission that is unequaled. You are making this happen. You are the one who wants it. He may take control later but here and now you are the one who is really imitating the submission to your man.

When his cock came out that's when I really lost control. It was amazing. 8 inches long, half a beer can thick, with a birthmark that ran along the side making it seem twice the size. I made to look into his eyes and smile but slowed as I gazed at his stomach, He didn't have a true six pack but he had a tight stomach that made my fatness even more pronounced in my head. I now knew why he was nervous. I long and wide birthmark started from just under his nipple on his right side. It trailed down his body growing wider till it passed his waist then narrowed to run along his cock and thigh. I looked to his eyes but could see he had turned away. I knew instantly what I had to do.

Stealing his earlier Idea of turning my insecurity into a moment I kissed his right nipple then made my way down his body never leaving the mark. When I reached his waist he pulled back saying "It's ok if you don't want to."

"Are you kidding" I laughed. "You are the sexiest thing I've ever seen. I figured someone who looked like you wouldn't want to touch me."

"You're wrong. I love your body; it's so sexy and big."

I took him at his word as he did I. We stared into each other's eyes for a minute or more. Then he leaned down and kissed me tenderly. For the first time I really kissed him back. He fell next to me and we ran our hands over the others biggest fears and began to make love. I took him in my mouth, and I felt reborn.

'You see' she almost sang 'This is why I'm here' and for the first time I let Kylie out to play.

It was like nothing I've ever experienced before or sense. That first time I let her out, it was like a thunderbolt. Like a plane breaking the sound barrio. She slammed in to my conciseness, and moaned loudly onto Joe's cock. Her/my tongue bathed the head and swallowed him down our throat. I felt myself pulling back and just going off an instinct that I had never felt. She was now running the show. Kylie, the girl I wished I could be. Kylie the little ignored whore who never got to play, but didn't resent it. Instead she took her time, patiently nudging me to her side. Slowly preparing me for this moment of acceptance, A Jekyll and Hyde moment where both sides realize the need for the other.

Kyle has to exist because there is no way a body and face like his could ever be confused for a woman's. That also meant that Kyle didn't really have to ever change. He could still be the straight guy, the sports fan, the main stay.

Kylie had to exist because she was who Kyle wished he could really be. The Whore who loves cock. The slut who dresses like one. The one who got what both really needed. A hard cock in their mouths and ass.

In the fraction of a second that happened I became a slut possessed. I swallowed his whole length. I felt his head hit my tonsils and I gagged on his cock. I was now Kylie, no more split. I was a filthy cock whore who wanted no needed to please this god before me.

I felt his hand on my chin he pulled me back from his cock, but I couldn't help licking it one more time as he popped from my mouth. He kneeled next to me and flipped me on to all fours. HE grabbed my mammoth cheeks and pulled them apart. I didn't know what to expect when he slid in his cock but I braced myself for the invasion when I felt his tongue bathe my hole. He rimmed me so long and hard I was a quivering mess after. My knees were week, my face buried in the comforter as I melted and opened more. Only after my ass felt a velvet pussy did I notice my cock was rock hard. All Four inches of me was like stone. Joe's hand grabbed my cock and began to stroke it. Only for a minute or so, then moving his hand to my pussy hole, and slipping in a finger. Then two. Then three.

He leaned over me sliding a lubed latex cover cock in to my slit and kissed the very back of my neck and whispered "are you ok"

"Fuck Me" Kylie said, "Oh please Fuck ME."

He kissed my neck again and lined his cock up. It slid into Kylie's pussy so slow and she loved every second of it. I realized then that my language was changing now, not my ass but Kylie's pussy. Normally I would have thought about this a long time but decided fuck it, and go with it.

Kylie moaned for her lover as he bottomed out. His Balls resting on her ass, He pulled out slow and she squealed in delight. He slid back in and she moaned like a slut.

"Please Joe, I have to know. Fuck me, fuck me hard and fast and cum in me.

Joe did just that. He warmed up to it, starting with a nice steady rhythm that opened me/her up. I felt pleasure like I've never known. The moment he hit my prostate I cried out in joy. I began to fuck him back with my pussy. Meeting his thrusts with my own and twisting my hips to rock him deeper into me. I felt his cock grow with his speed. Every moment was bliss, every second was heaven. All I wanted from that point on was to exist at this feeling, giving myself to man as he took me, feeling his cock take my body as his own. His cock swelled in me. Splitting me open. I felt this need in my stomach to keep going then it popped, that's the only way to describe it. Something popped and cum began to shoot from my clit. His cock Exploded into me. I could feel something hot and slippery inside of me grow and realized the condom was broken and didn't care. At this point it was done. He began to pull out but kissed my back with every inch he took. I melted in to the bed as he did it. He stood up and picked up a towel. Wiped his glorious pleasure machine and resumed his position on the bed and kissed me.

'Kiss him back' she whispered. 'Thank him for both of us'

I did.

He stroked my back and shoulders, ran his hands on my face, kissed me on my lips and cheeks. I being the whore I now was grabbed his stick and began to stroke it.

'Good Girl' Kylie said 'Get him going again.

His cock showed some signs of life, and I decided it was time to see what sex in a shower is all about.

Continued in Kylie gets her first uniform.I want to tell you all how I became the Cross-dressing slut I am today. My name is Kylie, and these stories are all true.

I could tell you the same stuff all cross dressers seem to say, how I dressed in my mothers lingerie when I was young. How I hid it even from myself throughout high school. How Kylie's voice grew in my head till I couldn't take it anymore and had to try getting fucked. The first time a man took me I was 20. I met him on a website and went to a dirty hotel and had his cock fuck my tight virgin hole. It freaked me out after and I swore off cock forever.

"You liked it though" I heard in my head.

"You want more." The voice was so like my own but slower and softer. It would grow quiet for weeks then come back loud and demanding, "Go online...find more cock. I need it, you need it."

I fought and fought. I tried to convince myself that it was from watching too much porn. I didn't really have these desires, I was confused is all. That all changed when I met Joe.

Joe was my age. He responded to an ad I had placed on a cruising site. I told him like I'm about to tell you that I am fat. I'm 5'8 and over 300 pounds. My ass is huge. He liked that, he told me he wanted to see me bent over in his bed with my fat ass in his face. He wanted to rim me and fuck me till I came.

Since that is exactly what I was looking for, I agreed to meet. I still wasn't ready for someone to see me in my lady clothes. I went to his place as my normal self. On the way there I switched the radio in my car to pop music, something I never listened to normally. As I drove, I began to feel like someone else, something other than who I am 9-5 during the week.

I felt a shaking in my stomach. It had been two years since that disgusting hotel, where a man I hadn't really liked had deflowered my hole. Two years since I had really given in to that voice, the one that sounded like me but didn't.

She was back now, whispering about great it will be when he's inside me. How the taste of his cock will finally set her free. An old Britney tune came on the radio and I heard her say to me, "let me take over tonight, I know what you need more than you do. I can make this night great."

After driving for half an hour with voices arguing in my head, I pulled up to the building that Joe lived in. It was a standard bungalow with a buzzer on the front door. I paused before hitting the button. I knew this was my last chance to back out. If I hit the buzzer I was committed to becoming his bottom for the night.

"Push IT" I heard.

"You want this; it's why you drove here. If you leave you'll be back cruising sites for dirty talk. Sitting alone reading stories instead of living them". My hand stayed at my side. "Push IT NOW" the voice now demanding I take the final step.

Slowly my hand rose to the list of names next to the small round buttons that seemed so much larger than they had before. I pushed Joe's buzzer. A minute later a voice with that speaker twinge said "Kyle?"

I tried to speak but instead my voice caught in my throat and I coughed to get it back. With a mighty effort I replied "Yes".

"2A" The voice said back.

I grabbed the door handle as it buzzed and took a fatal step inside. The Door slammed behind me as I let it go. Chicago doors tend to be heavy to keep out the cold and this one did not disappoint. What sounded like a bomb went off behind me and I jumped, realizing what had happened I made my way up the stairs to door 2A. I didn't have to knock; he must have been standing right behind the door because it opened as I reached his mat.

The man standing there was gorgeous; there is no other way to say it. Even now as experienced as I am as bottom slut, I don't often find men overtly attractive. I find women beautiful and sexy. With most men all I want to know is how well they can fuck. Joe is one of the few that I have looked at thought about how good the look. His body was lean and cut, his biceps had a nice definition but not in an overworked way. His face was sweet and honest with a pair of small glasses that made me think college student right away.

I immediately expected him to throw me out. Here I am a fat little troll and there is this Greek statue of a man who clearly could have any one he wanted, Man or woman. Waving me in without speaking he glanced around the stairway and shut the apartment behind me.

The main room was sparsely decorated with a small tube TV and a black love seat. It looked a lot like many of my friend's places throughout the city. The familiar setting both relaxed and unnerved me. I hadn't really thought much about it, but I think a small part of me was expecting this guy to be a serial killer. The familiar layout seemed to relieve me of that concern. I was also feeling a little strange because I had come here to do a secret thing, but couldn't help but think of my friends and what they were up to. This was the last thing I wanted in my head. I already felt dirty and guilty enough without having to think of my real life.

"Would like a drink?" Joe asked. I had been in my head so deep in thought his question startled me.

"I'll take a beer if you've got it"

"One minute, please sit down."

I sat on his black IKEA love seat. Still expecting to be thrown out on my fat ass by this hot man who clearly shouldn't have a problem getting laid, and wouldn't want a slob like me.

"Relax" she whispered. "He smiled when you came in. He's as nervous as you are. Look at his hands trying to open that bottle."

She was right; His hands were shaking slightly as he returned from the kitchen. He handed me the beer and sat down. We were next to each other like that for a long time watching some realty show on TV not speaking or moving, except when my arm brought the cold beer to my lips.

"So..This is awkward" I said.

"I know." Joe returned. "I've never done this before, Have you?"

"Once, a couple years ago."

"What was that like?"

"He was a little older so he kind of took control." I was speaking softly now, trying to calm myself down.

"Ah."

He looked at me in the eyes for a few seconds then grabbed my hand and pulled me in to a kiss. I know story tellers like to talk about fireworks and lightning when two people kiss, that didn't happen to me then. When he first pressed his lips to mine I was so shocked by the intimacy of it I didn't feel anything. When I felt his hand on the back of my head I swooned. When his fingers played with the little hairs on the small of my neck I felt a wave of pleasure roll through me and I pressed myself to him.

His hands found the bottom of my shirt and pulled it over my head. I tried to cover my belly with my hands and he very sweetly moved them and kissed my stomach just under my belly button. When that happened I became an animal, I pulled his shirt off and wrapped my arms around him. I kissed and sucked his neck moved my way up his ears then around to his cheek, he turned and jammed his tongue down my throat. I sucked on it like it held the antidote to poison that was turning my body loose.

'Go to his bed' She said. 'Suck his cock'

Joe was kissing my neck as I began to stand up. At first I think he thought I was running out because the look on his face was one of total confusion. I smiled at him as demurely as I could, and slowly slid my jeans off in one move. Once I kicked them off I grabbed his hand brought him to his feet. We kissed as we walked to bedroom. Almost falling over twice, but we couldn't stop.

I felt the bed before I saw it. It bumped against my legs and I sank down. I used my hands to tell Joe to keep standing and undid his belt. All these years later and that is still my favorite moment of foreplay. Sissies Sluts like me I'm sure understand this, when you begin to undo a belt it gives you feeling of both control and submission that is unequaled. You are making this happen. You are the one who wants it. He may take control later but here and now you are the one who is really imitating the submission to your man.

When his cock came out that's when I really lost control. It was amazing. 8 inches long, half a beer can thick, with a birthmark that ran along the side making it seem twice the size. I made to look into his eyes and smile but slowed as I gazed at his stomach, He didn't have a true six pack but he had a tight stomach that made my fatness even more pronounced in my head. I now knew why he was nervous. I long and wide birthmark started from just under his nipple on his right side. It trailed down his body growing wider till it passed his waist then narrowed to run along his cock and thigh. I looked to his eyes but could see he had turned away. I knew instantly what I had to do.

Stealing his earlier Idea of turning my insecurity into a moment I kissed his right nipple then made my way down his body never leaving the mark. When I reached his waist he pulled back saying "It's ok if you don't want to."

"Are you kidding" I laughed. "You are the sexiest thing I've ever seen. I figured someone who looked like you wouldn't want to touch me."

"You're wrong. I love your body; it's so sexy and big."

I took him at his word as he did I. We stared into each other's eyes for a minute or more. Then he leaned down and kissed me tenderly. For the first time I really kissed him back. He fell next to me and we ran our hands over the others biggest fears and began to make love. I took him in my mouth, and I felt reborn.

'You see' she almost sang 'This is why I'm here' and for the first time I let Kylie out to play.

It was like nothing I've ever experienced before or sense. That first time I let her out, it was like a thunderbolt. Like a plane breaking the sound barrio. She slammed in to my conciseness, and moaned loudly onto Joe's cock. Her/my tongue bathed the head and swallowed him down our throat. I felt myself pulling back and just going off an instinct that I had never felt. She was now running the show. Kylie, the girl I wished I could be. Kylie the little ignored whore who never got to play, but didn't resent it. Instead she took her time, patiently nudging me to her side. Slowly preparing me for this moment of acceptance, A Jekyll and Hyde moment where both sides realize the need for the other.

Kyle has to exist because there is no way a body and face like his could ever be confused for a woman's. That also meant that Kyle didn't really have to ever change. He could still be the straight guy, the sports fan, the main stay.

Kylie had to exist because she was who Kyle wished he could really be. The Whore who loves cock. The slut who dresses like one. The one who got what both really needed. A hard cock in their mouths and ass.

In the fraction of a second that happened I became a slut possessed. I swallowed his whole length. I felt his head hit my tonsils and I gagged on his cock. I was now Kylie, no more split. I was a filthy cock whore who wanted no needed to please this god before me.

I felt his hand on my chin he pulled me back from his cock, but I couldn't help licking it one more time as he popped from my mouth. He kneeled next to me and flipped me on to all fours. HE grabbed my mammoth cheeks and pulled them apart. I didn't know what to expect when he slid in his cock but I braced myself for the invasion when I felt his tongue bathe my hole. He rimmed me so long and hard I was a quivering mess after. My knees were week, my face buried in the comforter as I melted and opened more. Only after my ass felt a velvet pussy did I notice my cock was rock hard. All Four inches of me was like stone. Joe's hand grabbed my cock and began to stroke it. Only for a minute or so, then moving his hand to my pussy hole, and slipping in a finger. Then two. Then three.

He leaned over me sliding a lubed latex cover cock in to my slit and kissed the very back of my neck and whispered "are you ok"

"Fuck Me" Kylie said, "Oh please Fuck ME."

He kissed my neck again and lined his cock up. It slid into Kylie's pussy so slow and she loved every second of it. I realized then that my language was changing now, not my ass but Kylie's pussy. Normally I would have thought about this a long time but decided fuck it, and go with it.

Kylie moaned for her lover as he bottomed out. His Balls resting on her ass, He pulled out slow and she squealed in delight. He slid back in and she moaned like a slut.

"Please Joe, I have to know. Fuck me, fuck me hard and fast and cum in me.

Joe did just that. He warmed up to it, starting with a nice steady rhythm that opened me/her up. I felt pleasure like I've never known. The moment he hit my prostate I cried out in joy. I began to fuck him back with my pussy. Meeting his thrusts with my own and twisting my hips to rock him deeper into me. I felt his cock grow with his speed. Every moment was bliss, every second was heaven. All I wanted from that point on was to exist at this feeling, giving myself to man as he took me, feeling his cock take my body as his own. His cock swelled in me. Splitting me open. I felt this need in my stomach to keep going then it popped, that's the only way to describe it. Something popped and cum began to shoot from my clit. His cock Exploded into me. I could feel something hot and slippery inside of me grow and realized the condom was broken and didn't care. At this point it was done. He began to pull out but kissed my back with every inch he took. I melted in to the bed as he did it. He stood up and picked up a towel. Wiped his glorious pleasure machine and resumed his position on the bed and kissed me.

'Kiss him back' she whispered. 'Thank him for both of us'

I did.

He stroked my back and shoulders, ran his hands on my face, kissed me on my lips and cheeks. I being the whore I now was grabbed his stick and began to stroke it.

'Good Girl' Kylie said 'Get him going again.

His cock showed some signs of life, and I decided it was time to see what sex in a shower is all about.

Continued in Kylie gets her first uniform.

wakes   kylie  

Nov 26, 2017 in anal

Tags

Search