Jamie's Desire

Charles arrived at Jason's house for a sleepover.  Tonight was the night Jason was going to show him his sissy side.  His mother Pamela dressed him up for years.  Mommy and the daughter she never had.  Around the house, Jamie preferred to wear women's clothes and makeup, and his mother encouraged him.  His older brother Steve, who was now off in college was indifferent to it.  His father had divorced his mother and moved away.

With her ex husband gone, Pamela was more emboldened to sissify Jason, who she started calling Jamie. She taught her sissy son how to do make up, cook and clean, and Jamie was a real help around the house.  Since Pamela was well liked around the town, she didn't have to worry how the ladies at the salon or at her favorite store would react.  She just brought Jamie in, usually near closing time.

Jamie wore a pink skirt and top as the sissy paced the floor in the living room.  "Are my nails okay mom, " he asked?  "Maybe I should touch up my lipstick."

"Relax, sweetie.  It's only a sleep over isn't it, " she arched her eyebrow?  "Only video games and action movies?  Or, are you looking for something else?"

Jamie blushed.  "Mother, it's not like that, " he replied as he played with his shoulder length brown hair.  "Charles is my best friend, and I've told him about my dress up at home."

Mother nodded, with a hint of skepticism in her voice.  "Uh huh, and he wants to come stay the night with you?"

Jamie stomped his feet.  "Mother, it's not like that."  There was a knock on the door.  "Oh my God, he's here."

"Well, don't just stand there sweetie, answer it."

Jamie answered the door with a nervous smile.  It was Charles, dressed casually in gym shorts and a t-shirt.  He was a good six inches taller than the slender sissy with dark hair and a tone body. "Hi Charles, come on in."

He looked at his sissy friend for a moment but gave no sign in his expression what he thought.  "Sup Jason."  He looked over at the blond woman with the DD breasts.  She was wearing a tight, bust flattering blue dress.  "Hi Miss Bryant.  Nice to see you again."

Jamie reached out and touched his arm.  "So, I have both of the latest releases, Winds Of War or Journey Through Greshlock's Dungeon.  Whatever you wanna play."

"I'm cool either way, " he replied.  "I'm down for a dungeon crawl."

"I was hoping you'd say that."

"Aren't you gonna offer your guest a drink, " his mother shouted down the hallway.  She shook her head and went to the kitchen.

They sat down in front of Jamie's TV.  "Dude, you're mother's fucking hot."

The sissy nodded in agreement.  "She is pretty.  She taught me a lot."

"Cool, so this is how you prefer to dress at home?"  Charles picked up the game controller and selected a warrior.

"Yeah, for as long as I can remember."  Jamie selected a female Elven Wizard.

"You look good.  I mean, you look convincing."  He casually glanced over at his sissy friend.  "Do you ever go outside like this?  Oh, let's go buy some equipment first."

Jamie nodded.  "Sometimes mom takes me to the mall or the salon at night, and I've gone to a few of her and her friend's get togethers."

"Cool."

The door was open and Jamie's mother came in with a couple of sodas on ice.  "Hey you two.  I thought I'd bring you some drinks since somebody forgot to offer.  Very unlady like, Jamie."

Charles smiled at her as he accepted his drink.  He caught himself staring at her.  Between her ruby red lipstick and her breasts and sexy curves, it was hard not to stare.  "Thank you Miss Burris."

"None of this Miss Burris nonsense sweetie.  Call me Pam.  If you need anything at all, just ask, " she said with a wink and a grin.

"Okay mom, thanks.  Close the door on your way out."  Jamie knew his mom could be a flirt, and she might tempt his best friend.

She giggled as she walked out the door, shutting it behind her.  "Okay.  You two behave now."

The two friends enjoyed their game.  They seemed to play in synch.  Charles took out many of the monsters with his blade, but Jamie saved him a few times with his spells.  "Oh, that was a close one.  Nice save bud."

"That's what I'm here for, " the sissy replied as he glanced over and noticed Charles had a bulge in his shorts.  He already knew his friend was well endowed, and seeing him aroused made Jamie tingle all through his body.  "Thinking about my mom?"

Charles rubbed his shorts almost mindlessly.  "Huh?  Yeah, I guess."

"You know, you can take it out and play with it, if you want.  I don't mind."  Jamie couldn't believe he said that as he blushed.

Charles looked over at the blonde sissy.  "You don't mind?"

Jamie shrugged.  "No.  Why should I?"

Charles pulled out his seven inch cock, which was still not all the way hard.  He slowly stroked it.  "Do you ever wonder what it's like to, um, give a blowjob?"

Though he was staring at his friend's cock, Jamie was startled by the question.  "Huh?  Um, I don't know."

"I'm sorry.  I just wondered since you like dressing up and..."  Charles stopped his line of thought.  "Forget I said anything."

"Do you want me to suck your cock?"

Charles liked the idea.  "Only if you want to.  I don't want to..."

Jamie practically dove face first into his lap and had his mouth around his bigger friend's cock in no time."

"Oh my God.  Shit, this is awesome.  Nobody's ever done this for me."  Charles leaned back and let his friend do what he was doing.

In reality, Jamie had never sucked a cock before, but he fantasized about it a lot.  He listened to his mother and her friends talk about it, and recently his mother and he had a talk.  His mother had started it by saying it was okay if he wanted to date guys.

Jamie was working his tongue around the head of Charles' cock as he gently sucked it.  He tasted cum for the first time, but he wasn't prepared when his friend shot his load into his mouth.  "Oh, fuck.  I'm sorry.  I should have told you I was cumming."

Jamie sucked every last drop.  As he rose back up, he giggled and wiped some cum that leaked out of the side of his mouth.  "That's okay.  Don't worry about it."

Charles had a surprised look on his face.  "Did you just swallow it?"

"I couldn't just spit it on my floor, " the sissy replied as he touched up his lipstick.  "Why, was I not supposed to?"

"No, it's just, " he smiled back at his feminine friend.  "Thank you."

Charles had no sooner pulled up his shorts than the door opened.  It was Pamela.  She looked at the two with suspicion in her eyes.  "What have you two been up to?"

"Just playing a game mom, " Jamie replied.

"Uh huh, " I bet you were, " she chuckled.

"Yeah, Miss Barnes, um, Pam.  It's an RPG.  I'm playing a warrior, and Jason is an Eleven Enchantress."

"I see, " she looked at both of them with a mischievous grin.  "Is the warrior protecting his lady?"

"Mother please."

"Okay you two.  Pizza is here.  I figured I'd order out.  Just go help yourselves."

"Awesome, " Charles stood up and went out the door to the kitchen.  "I'm starved.  Thanks Pam."

"Don't mention it sweetie, " she replied as she watched him walk down the hall.  She turned her head to her sissy son.  "He is a cutie dear.  Make sure you use protection."

Jamie was standing face to face with her.  "Mother, stop it."

Pamela sniffed the air around her son's mouth.  "Uh huh."  She shook her head.  Somebody's been naughty here."

Jamie blushed.  "Mother, please.  Not now.  You're the one who said I could have him over and show him how I dressed."

"Dressed dear, " she smirked.  "I didn't say behave like a little slut."

"Mother."

"I'm teasing.  I know you're getting to be a young woman now."

Charles returned with a plate of pizza.  "Whatcha standing around here for.  Pizza is gonna get cold."

"We can't eat too much dear, " Pamela replied.  "We want to keep our girlish figures.  Don't we sweetie?"

"Oh my God, " Jamie rolled his eyes.

"Hey, " if you want to watch a movie with me, there's that new action picture on pay per view everyone has been raving about."  Pamela walked down the hall.

"Everything okay, " Charles asked.  "I didn't get you in trouble or anything, did I?"

Jamie laughed.  "No, nothing like that."

"Hey, are we okay.  I don't want anything to get weird between us."

Jamie touched his hand.  "No.  Everything is fine.  I'm gonna go get some pizza."


The movie was entertaining, and they were all laughing.  Pamela opened a bottle of wine and the three drank and had a good time.  By then, Charles was only wearing his shorts, and both Jamie and his mother were in matching pink babydoll nighties that they bought on a recent shopping trip.

Pamela couldn't resist getting a few playful innuendos in there.  She was feeling a bit horny from the wine and seeing Charles without his shirt.  When the movie was over, Charles remarked about the lead actress.  "She's a total hottie."

"Yeah, but her breasts are fake, " Pamela retorted.

"Mother."

"These, " she touched her own DD breasts.  "These are real."  She smiled proudly.  "Wanna see?"

Charles stared but said nothing, hoping he'd get a peak.  Jamie stood up.  "Okay mother.  We're gonna go back to my room and play more video games."

"Well, he can sleep on the hideaway bed in the sofa when he's ready, " Pamela replied.

"He's gonna sleep in my room with me."

His mother arched an eye brow.  "Oh, is he now?"

"Yeah, I can crash there.  I don't mind sleeping on the floor."

Pamela stood up.  "Okay then.  I'm gonna turn in early."  She grabbed the bottle and went to her room where she would have an extended session with her vibrator.  "Good night you two."

"Good night Pam."

Charles and Jamie played for a few more hours before they were ready for bed.  "Um, Charles.  You don't have to sleep on the floor.  My bed is plenty big."

"Are you sure, because, I like to sleep in the nude?"

Jamie giggled.  "It's nothing I haven't seen before."

"In that case, " he stood up and pulled off his shorts.  Jamie couldn't help but look.  It was half erect again.

"Jamie, " he said as he walked up to the sissy.  He surprised him by planting a kiss on his pretty pink lips.  "I'm sorry.  I just had to."

Jamie blushed.  "Don't be sorry.  I liked it."

"You did?"

Jamie nodded.

"It's weird, because I don't think of you as a boy right now, even though I've known you most of my life."

There was a hint of vulnerability in the sissy's voice.  "You don't?"

He shook his head.  "No.  I think of you as a pretty girl."  He leaned in and kissed his smaller friend again.  He was clearly getting hard.

He sat on the bed.  "Have you ever, I mean, did you ever wonder what it would be like if a guy..."

"Fucked me, " Jamie finished his sentence.  "Yes, I have, but not just any guy."

"Who?"

Jamie fell to his knees in front of Charles.  "You, " he started sucking his cock for the second time.  He had a feeling this would beome an ongoing experience.

Charles started running his hands through he sissy's hair.  "Hope this doesn't change our friendship."

Jamie looked up at him.  "It won't."

Jamie was enjoying the experience of sucking his best friend's cock, but Charles stopped him.  "Do you have any lube?"

The sissy went to his night stand.  "Right here."

"Okay, get on your hands and knees right here on the bed."  Charles pulled the thong out of the way and started applying the lube with one finger, then two and finally a third finger inside Jamie's virgin sissy hole.  He was squirming in anticipation and delight.

"Are you ready?"

Jamie looked back.  "I've been looking forward to this for a long time."

Charles started pressing against the sissy's tight sphincter and soon gained access as Jamie let out a whimper.  "You okay?"

Jamie reached back one of his hands to touch his lover.  "Keep going baby."

Charles kept pushing inside, inch by inch.  The tightness was an incredible feeling to him.  He'd had vaginal sex with two of his old girlfriends, but this was his first anal experience.  "It's all the way in Jamie."

"He looked back with lust in his eyes.  "Fuck me."

The thrusts started off slowly, and both of their grunts and moans were a little loud.  Pamela was awakened by the sounds and she started fingering herself as she lay in bed.  Other mothers might have interrupted this moment, but she wanted it for his son.  She wanted him to figure out who he was, and she was going to love him no mater what.

"God, you're so tight, " Charles moaned.  "This is incredible."

Jamie was pushing back to take him deep on each re entry.  This was the moment he realized that this was what he wanted from sex, but more than that, it was further validation that he was meant to be a girl.  "Keep fucking me baby."

Charles started picking up his pace.  "I love this."

"Good, " came the sissy's reply.  "We're doing it again."

Charles grabbed his hips and started thrusting faster.  "Damn right we are."  He could feel Jamie squeezing his cock just a little with his ass muscles as he continued to plow him.

Charles collapsed on top of his effeminate friend.  Jamie was pinned by his bigger best friend as the thrusts continued.  The sissy felt desired and owned by him.  He felt complete.  His biggest desire now was to mike him cum.  Charles started to slow down his pace as he wanted to make it last.  Jamie got an idea.  "Baby, lay on the bed for me."


Charles did as asked.  The sissy, with his nightie still on and the front of his thing still covering his clitty, proceeded to mount him with ease.  When he was all the way inside of him, Jamie leaned down and kissed him.  "Now who's on top, " he giggled?

Charles wrapped his arms around the sissy and kissed him in a loving embrace as he thrust upward.  "You know, this makes you my girl."

He kissed him back.  "This makes you my man."

Jamie started riding up and down on Charles' hard cock as the two were locked in eye contact with expressions of love and raw passion.  When he was deep inside of him, Jamie would wiggle his ass and send a tingle throughout Charles' body.

This continued for several more minutes before Charles announced, "I'm gonna cum."

"Do it, " Jamie replied.

"I don't have a condom on, " replied.

"Does it look like I care.  Come inside me baby."  The sissy left him little choice as she finally drove him over the edge.  Jamie himself felt like cumming and was leaking, but the full orgasm never came as his lover came deep inside him.  That was all he really wanted from the moment.  He felt complete.  Jamie leaned down and kissed him.  "God, I think I love you."

Charles kissed him back, but didn't reply.  The two slept peacefully together and awoke the next morning to he smell of breakfast.  Pam was in the kitchen. She knew what happened, but she said nothing and didn't even tease them.  After eating, Charles had to go.  Jamie stood on the porch in her nightie and kissed him.  Neither cared if they were seen, though if anybody was watching, it didn't appear to be the case.

Jamie walked into the house to the stare of his mother.  "What?"

Mother smiled and shook her head.  "Don't give me that.  You got laid last night, didn't you?"

Jamie blushed.  "How did you know?"

Mother rolled her eyes.  "Oh please.  You two made enough noise to wake the dead."

"I'm sorry mom."

Mother playfully slapped her sissy's son's arm.  "Don't be sorry.  Just be warned that I may have a man here some time and you'll get to hear us all night."

Jamie laughed.  "Oh my God."  He got silent.  "I don't think I'm gay mom."

She looked at her son skeptically.  "You don't?"

Jamie shook his head.  "No, I don't.  Remember those web sites we were looking at the other day?  I think I may be transgender.  I feel more like a woman than a man.

"Well, I should think so the way he was giving it to you last night."

"Mother!"

Pamela put her arm around Jamie.  "I'm just teasing you dear.  We'll get you a therapist on Monday and help you sort this out.  If it turns out you're transgender, we'll make you the prettiest girl on the block."

Jamie hugged his mother.  Her love and acceptance meant everything to him.  "Thanks.  I love you mom."

"I love you too baby.  No matter what."Jamie's Desire

Charles arrived at Jason's house for a sleepover.  Tonight was the night Jason was going to show him his sissy side.  His mother Pamela dressed him up for years.  Mommy and the daughter she never had.  Around the house, Jamie preferred to wear women's clothes and makeup, and his mother encouraged him.  His older brother Steve, who was now off in college was indifferent to it.  His father had divorced his mother and moved away.

With her ex husband gone, Pamela was more emboldened to sissify Jason, who she started calling Jamie. She taught her sissy son how to do make up, cook and clean, and Jamie was a real help around the house.  Since Pamela was well liked around the town, she didn't have to worry how the ladies at the salon or at her favorite store would react.  She just brought Jamie in, usually near closing time.

Jamie wore a pink skirt and top as the sissy paced the floor in the living room.  "Are my nails okay mom, " he asked?  "Maybe I should touch up my lipstick."

"Relax, sweetie.  It's only a sleep over isn't it, " she arched her eyebrow?  "Only video games and action movies?  Or, are you looking for something else?"

Jamie blushed.  "Mother, it's not like that, " he replied as he played with his shoulder length brown hair.  "Charles is my best friend, and I've told him about my dress up at home."

Mother nodded, with a hint of skepticism in her voice.  "Uh huh, and he wants to come stay the night with you?"

Jamie stomped his feet.  "Mother, it's not like that."  There was a knock on the door.  "Oh my God, he's here."

"Well, don't just stand there sweetie, answer it."

Jamie answered the door with a nervous smile.  It was Charles, dressed casually in gym shorts and a t-shirt.  He was a good six inches taller than the slender sissy with dark hair and a tone body. "Hi Charles, come on in."

He looked at his sissy friend for a moment but gave no sign in his expression what he thought.  "Sup Jason."  He looked over at the blond woman with the DD breasts.  She was wearing a tight, bust flattering blue dress.  "Hi Miss Bryant.  Nice to see you again."

Jamie reached out and touched his arm.  "So, I have both of the latest releases, Winds Of War or Journey Through Greshlock's Dungeon.  Whatever you wanna play."

"I'm cool either way, " he replied.  "I'm down for a dungeon crawl."

"I was hoping you'd say that."

"Aren't you gonna offer your guest a drink, " his mother shouted down the hallway.  She shook her head and went to the kitchen.

They sat down in front of Jamie's TV.  "Dude, you're mother's fucking hot."

The sissy nodded in agreement.  "She is pretty.  She taught me a lot."

"Cool, so this is how you prefer to dress at home?"  Charles picked up the game controller and selected a warrior.

"Yeah, for as long as I can remember."  Jamie selected a female Elven Wizard.

"You look good.  I mean, you look convincing."  He casually glanced over at his sissy friend.  "Do you ever go outside like this?  Oh, let's go buy some equipment first."

Jamie nodded.  "Sometimes mom takes me to the mall or the salon at night, and I've gone to a few of her and her friend's get togethers."

"Cool."

The door was open and Jamie's mother came in with a couple of sodas on ice.  "Hey you two.  I thought I'd bring you some drinks since somebody forgot to offer.  Very unlady like, Jamie."

Charles smiled at her as he accepted his drink.  He caught himself staring at her.  Between her ruby red lipstick and her breasts and sexy curves, it was hard not to stare.  "Thank you Miss Burris."

"None of this Miss Burris nonsense sweetie.  Call me Pam.  If you need anything at all, just ask, " she said with a wink and a grin.

"Okay mom, thanks.  Close the door on your way out."  Jamie knew his mom could be a flirt, and she might tempt his best friend.

She giggled as she walked out the door, shutting it behind her.  "Okay.  You two behave now."

The two friends enjoyed their game.  They seemed to play in synch.  Charles took out many of the monsters with his blade, but Jamie saved him a few times with his spells.  "Oh, that was a close one.  Nice save bud."

"That's what I'm here for, " the sissy replied as he glanced over and noticed Charles had a bulge in his shorts.  He already knew his friend was well endowed, and seeing him aroused made Jamie tingle all through his body.  "Thinking about my mom?"

Charles rubbed his shorts almost mindlessly.  "Huh?  Yeah, I guess."

"You know, you can take it out and play with it, if you want.  I don't mind."  Jamie couldn't believe he said that as he blushed.

Charles looked over at the blonde sissy.  "You don't mind?"

Jamie shrugged.  "No.  Why should I?"

Charles pulled out his seven inch cock, which was still not all the way hard.  He slowly stroked it.  "Do you ever wonder what it's like to, um, give a blowjob?"

Though he was staring at his friend's cock, Jamie was startled by the question.  "Huh?  Um, I don't know."

"I'm sorry.  I just wondered since you like dressing up and..."  Charles stopped his line of thought.  "Forget I said anything."

"Do you want me to suck your cock?"

Charles liked the idea.  "Only if you want to.  I don't want to..."

Jamie practically dove face first into his lap and had his mouth around his bigger friend's cock in no time."

"Oh my God.  Shit, this is awesome.  Nobody's ever done this for me."  Charles leaned back and let his friend do what he was doing.

In reality, Jamie had never sucked a cock before, but he fantasized about it a lot.  He listened to his mother and her friends talk about it, and recently his mother and he had a talk.  His mother had started it by saying it was okay if he wanted to date guys.

Jamie was working his tongue around the head of Charles' cock as he gently sucked it.  He tasted cum for the first time, but he wasn't prepared when his friend shot his load into his mouth.  "Oh, fuck.  I'm sorry.  I should have told you I was cumming."

Jamie sucked every last drop.  As he rose back up, he giggled and wiped some cum that leaked out of the side of his mouth.  "That's okay.  Don't worry about it."

Charles had a surprised look on his face.  "Did you just swallow it?"

"I couldn't just spit it on my floor, " the sissy replied as he touched up his lipstick.  "Why, was I not supposed to?"

"No, it's just, " he smiled back at his feminine friend.  "Thank you."

Charles had no sooner pulled up his shorts than the door opened.  It was Pamela.  She looked at the two with suspicion in her eyes.  "What have you two been up to?"

"Just playing a game mom, " Jamie replied.

"Uh huh, " I bet you were, " she chuckled.

"Yeah, Miss Barnes, um, Pam.  It's an RPG.  I'm playing a warrior, and Jason is an Eleven Enchantress."

"I see, " she looked at both of them with a mischievous grin.  "Is the warrior protecting his lady?"

"Mother please."

"Okay you two.  Pizza is here.  I figured I'd order out.  Just go help yourselves."

"Awesome, " Charles stood up and went out the door to the kitchen.  "I'm starved.  Thanks Pam."

"Don't mention it sweetie, " she replied as she watched him walk down the hall.  She turned her head to her sissy son.  "He is a cutie dear.  Make sure you use protection."

Jamie was standing face to face with her.  "Mother, stop it."

Pamela sniffed the air around her son's mouth.  "Uh huh."  She shook her head.  Somebody's been naughty here."

Jamie blushed.  "Mother, please.  Not now.  You're the one who said I could have him over and show him how I dressed."

"Dressed dear, " she smirked.  "I didn't say behave like a little slut."

"Mother."

"I'm teasing.  I know you're getting to be a young woman now."

Charles returned with a plate of pizza.  "Whatcha standing around here for.  Pizza is gonna get cold."

"We can't eat too much dear, " Pamela replied.  "We want to keep our girlish figures.  Don't we sweetie?"

"Oh my God, " Jamie rolled his eyes.

"Hey, " if you want to watch a movie with me, there's that new action picture on pay per view everyone has been raving about."  Pamela walked down the hall.

"Everything okay, " Charles asked.  "I didn't get you in trouble or anything, did I?"

Jamie laughed.  "No, nothing like that."

"Hey, are we okay.  I don't want anything to get weird between us."

Jamie touched his hand.  "No.  Everything is fine.  I'm gonna go get some pizza."


The movie was entertaining, and they were all laughing.  Pamela opened a bottle of wine and the three drank and had a good time.  By then, Charles was only wearing his shorts, and both Jamie and his mother were in matching pink babydoll nighties that they bought on a recent shopping trip.

Pamela couldn't resist getting a few playful innuendos in there.  She was feeling a bit horny from the wine and seeing Charles without his shirt.  When the movie was over, Charles remarked about the lead actress.  "She's a total hottie."

"Yeah, but her breasts are fake, " Pamela retorted.

"Mother."

"These, " she touched her own DD breasts.  "These are real."  She smiled proudly.  "Wanna see?"

Charles stared but said nothing, hoping he'd get a peak.  Jamie stood up.  "Okay mother.  We're gonna go back to my room and play more video games."

"Well, he can sleep on the hideaway bed in the sofa when he's ready, " Pamela replied.

"He's gonna sleep in my room with me."

His mother arched an eye brow.  "Oh, is he now?"

"Yeah, I can crash there.  I don't mind sleeping on the floor."

Pamela stood up.  "Okay then.  I'm gonna turn in early."  She grabbed the bottle and went to her room where she would have an extended session with her vibrator.  "Good night you two."

"Good night Pam."

Charles and Jamie played for a few more hours before they were ready for bed.  "Um, Charles.  You don't have to sleep on the floor.  My bed is plenty big."

"Are you sure, because, I like to sleep in the nude?"

Jamie giggled.  "It's nothing I haven't seen before."

"In that case, " he stood up and pulled off his shorts.  Jamie couldn't help but look.  It was half erect again.

"Jamie, " he said as he walked up to the sissy.  He surprised him by planting a kiss on his pretty pink lips.  "I'm sorry.  I just had to."

Jamie blushed.  "Don't be sorry.  I liked it."

"You did?"

Jamie nodded.

"It's weird, because I don't think of you as a boy right now, even though I've known you most of my life."

There was a hint of vulnerability in the sissy's voice.  "You don't?"

He shook his head.  "No.  I think of you as a pretty girl."  He leaned in and kissed his smaller friend again.  He was clearly getting hard.

He sat on the bed.  "Have you ever, I mean, did you ever wonder what it would be like if a guy..."

"Fucked me, " Jamie finished his sentence.  "Yes, I have, but not just any guy."

"Who?"

Jamie fell to his knees in front of Charles.  "You, " he started sucking his cock for the second time.  He had a feeling this would beome an ongoing experience.

Charles started running his hands through he sissy's hair.  "Hope this doesn't change our friendship."

Jamie looked up at him.  "It won't."

Jamie was enjoying the experience of sucking his best friend's cock, but Charles stopped him.  "Do you have any lube?"

The sissy went to his night stand.  "Right here."

"Okay, get on your hands and knees right here on the bed."  Charles pulled the thong out of the way and started applying the lube with one finger, then two and finally a third finger inside Jamie's virgin sissy hole.  He was squirming in anticipation and delight.

"Are you ready?"

Jamie looked back.  "I've been looking forward to this for a long time."

Charles started pressing against the sissy's tight sphincter and soon gained access as Jamie let out a whimper.  "You okay?"

Jamie reached back one of his hands to touch his lover.  "Keep going baby."

Charles kept pushing inside, inch by inch.  The tightness was an incredible feeling to him.  He'd had vaginal sex with two of his old girlfriends, but this was his first anal experience.  "It's all the way in Jamie."

"He looked back with lust in his eyes.  "Fuck me."

The thrusts started off slowly, and both of their grunts and moans were a little loud.  Pamela was awakened by the sounds and she started fingering herself as she lay in bed.  Other mothers might have interrupted this moment, but she wanted it for his son.  She wanted him to figure out who he was, and she was going to love him no mater what.

"God, you're so tight, " Charles moaned.  "This is incredible."

Jamie was pushing back to take him deep on each re entry.  This was the moment he realized that this was what he wanted from sex, but more than that, it was further validation that he was meant to be a girl.  "Keep fucking me baby."

Charles started picking up his pace.  "I love this."

"Good, " came the sissy's reply.  "We're doing it again."

Charles grabbed his hips and started thrusting faster.  "Damn right we are."  He could feel Jamie squeezing his cock just a little with his ass muscles as he continued to plow him.

Charles collapsed on top of his effeminate friend.  Jamie was pinned by his bigger best friend as the thrusts continued.  The sissy felt desired and owned by him.  He felt complete.  His biggest desire now was to mike him cum.  Charles started to slow down his pace as he wanted to make it last.  Jamie got an idea.  "Baby, lay on the bed for me."


Charles did as asked.  The sissy, with his nightie still on and the front of his thing still covering his clitty, proceeded to mount him with ease.  When he was all the way inside of him, Jamie leaned down and kissed him.  "Now who's on top, " he giggled?

Charles wrapped his arms around the sissy and kissed him in a loving embrace as he thrust upward.  "You know, this makes you my girl."

He kissed him back.  "This makes you my man."

Jamie started riding up and down on Charles' hard cock as the two were locked in eye contact with expressions of love and raw passion.  When he was deep inside of him, Jamie would wiggle his ass and send a tingle throughout Charles' body.

This continued for several more minutes before Charles announced, "I'm gonna cum."

"Do it, " Jamie replied.

"I don't have a condom on, " replied.

"Does it look like I care.  Come inside me baby."  The sissy left him little choice as she finally drove him over the edge.  Jamie himself felt like cumming and was leaking, but the full orgasm never came as his lover came deep inside him.  That was all he really wanted from the moment.  He felt complete.  Jamie leaned down and kissed him.  "God, I think I love you."

Charles kissed him back, but didn't reply.  The two slept peacefully together and awoke the next morning to he smell of breakfast.  Pam was in the kitchen. She knew what happened, but she said nothing and didn't even tease them.  After eating, Charles had to go.  Jamie stood on the porch in her nightie and kissed him.  Neither cared if they were seen, though if anybody was watching, it didn't appear to be the case.

Jamie walked into the house to the stare of his mother.  "What?"

Mother smiled and shook her head.  "Don't give me that.  You got laid last night, didn't you?"

Jamie blushed.  "How did you know?"

Mother rolled her eyes.  "Oh please.  You two made enough noise to wake the dead."

"I'm sorry mom."

Mother playfully slapped her sissy's son's arm.  "Don't be sorry.  Just be warned that I may have a man here some time and you'll get to hear us all night."

Jamie laughed.  "Oh my God."  He got silent.  "I don't think I'm gay mom."

She looked at her son skeptically.  "You don't?"

Jamie shook his head.  "No, I don't.  Remember those web sites we were looking at the other day?  I think I may be transgender.  I feel more like a woman than a man.

"Well, I should think so the way he was giving it to you last night."

"Mother!"

Pamela put her arm around Jamie.  "I'm just teasing you dear.  We'll get you a therapist on Monday and help you sort this out.  If it turns out you're transgender, we'll make you the prettiest girl on the block."

Jamie hugged his mother.  Her love and acceptance meant everything to him.  "Thanks.  I love you mom."

"I love you too baby.  No matter what."