Daddy's Little Sissy Slut

Daddy's Little Sissy Slut

 

Oh, God, his cock is so big, and I think it's all the way inside me. I can't believe this is happening to me. I can't believe I love it so much. I'd touch myself, but the chastity device prevents that. I still feel like I could cum. It feels good, but I want to cum now. Oh, God.

 

Did he have to invite his buddy Steve? He's making me gag on his big cock. I can taste him. Not bad. I hope he cums soon. Is this really happening to me?

 

It happened so quickly, I still can't believe it. I've known Jim for a while. I walk by his place in the neighborhood all the time. He seemed nice. He always complimented me on the things I wore. I like to wear my black skirts and heels and a cute blouse. I know I'm not passable to those who like to judge. I'm just me.

 

Jim's wife passed away not long ago, and one day we talked for at least an hour. The way he was looking at me made me a bit uncomfortable, and I could swear he had an erection in his shorts. Let’s be honest. He wasn't hiding it so well. So, we were talking, and he hugged me at the end. Yeah, he had an erection. He was big down there too. I could tell.

 

Then a couple weeks later, it happened. I was sleeping naked in my bedroom. It had been a long day. I woke up in the dead of night to a weird feeling in my crotch area. I touched it, and there was something on my clitty. What the...

 

I got up and looked in the full-length mirror. There was a pink chastity cage on me. Who did this to me? I threw on a robe and went to my garage to get some tools. It took some doing, but I got that damned cage off of me. I know some girls like me who love them, but I don't. I've never had an interest in that sort of stuff. It seems stupid to me.

 

I returned to the room and noticed a package with a note on it. I opened the package to see this cute pink skirt and top outfit. A bit young for me, but I'll prance around the house in this sort of thing from time to time. Was that a bra and panties set in the package too? Pink. I love pink.

 

I started feeling sexy, so I drew a bubble bath. I did some body maintenance to make sure I was still smooth and started painting my toe and finger nails a shade of hot pink. The outfit was basically a pastel pink with some hot pink and glitter. On the top it said, "Sexy Girl". And, on the back of the panties, it said, "Naughty girl."

 

I let my nails dry and contemplated putting on the outfit. I put a pink nightie on and looked at the note. In my excitement, I never even bothered to read it. It read simply, "Becky, I hope you like all of my gifts. I want you wearing them when I come over in the morning. Then, I'll have a real gift for you" It was signed, Jim.

 

I wondered what he had in mind. He had locked me in chastity, but I got out of that. Oh well. Surely that wouldn't be a big deal? If he wanted to play in the bedroom, I would rock his world. I have some experience, but it's been a while.

 

In the morning, I grabbed a bite and slipped into the outfit. The knock came soon after, and it was Jim. He grinned at me. "I see you wore the special outfit I got you."

 

I smiled, "It's a little young for me, but I like it. Thank you."

 

"You look like a naughty little girl in need of a man to make a woman out of her."

 

I blushed. "Jim, I..."

 

"Slip out of that skirt and top. Let me see your lingerie. Let daddy have a look."

 

I complied, and he stared down at my crotch, grabbing it. "What's this?"

 

I giggled, "Jim, don't tell me you didn't know..."

 

"No, I mean, where is my chastity device? I thought I told you to be wearing what I asked you to wear."

 

I protested. "Look, Jim, I don't go in for that chastity nonsense..."

 

"If you want to be with me, you will wear what I tell you to wear."

 

I shook my head. "Look, Jim..."

 

He sat down on a chair and beckoned to me. "Bend over on my lap, young lady. Right now."

 

"Jim."

 

"Call me Daddy, and do as I tell you."

 

"But... Daddy, " I caught myself saying before I realized it. "I..."

 

"Right now, " he demanded.

 

I don't know why I did it, but I bent over his lap and felt the hard swats of his hand on my pantied bottom. It started to sting. I tried not to cry, but I couldn't help it. I apologized. "I'm sorry, Daddy."

 

"Are you gonna do what I say from now on, " he asked, knowing what I would say?

 

"Yes Daddy, I'm sorry."

 

He stood up. "Stay right there. I will be right back."

 

He left as I stood there, wondering where he had gone. It was maybe ten minutes before he returned with a brown paper bag. "Pull down your panties, young lady."

 

"What are you gonna do, " I asked?

 

"Take down your panties, " he ordered as he reached into the bag for another pink chastity device. He showed me a tag in the shape of a heart. It was pink with black writing. "You see this. It says, 'Daddy's Little Sissy Slut.' Just in case you are wondering, you are mine."

 

I felt my clitty twitch, and he quickly got the chastity device on me before I got hard. He grinned. "You don't cum unless I give you permission or I fuck that sissy hole of yours so well that you start leaking cum out of your caged clitty. Understand?"

 

I looked down at the ground, ashamed of my answer. "Yes, Daddy."

 

He stood up and took down his shorts. He was wearing no underwear over his neatly groomed cock. "Take a good look, " he ordered. "This is the cock you will be servicing whenever I need it."

 

My jaw dropped at the size of his massive cock. It was only semi hard and looked to be seven inches. He was big down there, truly gifted. "Oh my God, " I heard myself say.

 

He had told me that he and his wife had been married for about 20 years. My mind started to go there, thinking that I'm sure the big cock she was taking had her happily by his side. Jim could actually sense what I was thinking.

 

He smiled proudly. "Yeah, Emily knew how to take care of it, and I think you will too. She was a regular cum slut for me, though you never would have known that by looking at her."

 

I thought back at the conservative way in which she dressed and how she carried herself. "No, I never would have guessed."

 

"Exactly. That's how she wanted it, and I loved her. We didn't need everybody knowing our business, " He pointed to the floor. "You, on the other hand, will be a regular slut for me, and I don't care who knows."

 

"But... Jim, I..."

 

"You know, " he continued as he motioned to the floor, " I was gonna take that ass of yours today. I have a feeling it's good and tight, just as I like them." I got on my knees as he stuck his massive cock in my face, "But you had to disobey me, didn't you?"

 

I opened my mouth to answer and he shoved his cock inside as he laughed. "Don't talk with your mouth full, Missy. It's not polite."

 

I started sucking his cock like a girl possessed, but his shoving it into the back of my throat had me testing my gag reflex. "You're a naughty little cock sucker, aren't you?"

 

I looked up at him with tears in my eyes from the gagging and I kept sucking him. "My Emily was a cock slut too. She loved it when I took control in the bedroom, and I just knew you would too."

 

I could taste his precum. It had a strong, but pleasant taste to it. "Better get used to my cum, young lady. Unless you are taking it up that tight hole of yours, I want you swallowing it all like a good girl."

 

I just kept sucking, trying to get that cum out of him. I imagined there would be a lot. I would not be disappointed. "Think about my cock penetrating you for the first time. Maybe you'll earn that right. If you want to cum, you better get used to me inside you. I guarantee I'll make you cum like the horny little slut you are.

 

I kept sucking as he started to breath heavily. He was about there. I tried to position myself to take it all, but the amount was more than I anticipated. The first shot I swallowed, but there was so much it started dribbling down my chin a little. He laughed, "Such a messy little slut. Clean me up, bitch"

 

After a few moments, he pulled up his shorts. "What do you say, young lady?"

 

I blushed. "Thank you, Daddy."

 

He smiled. "Good girl. Now, I've got to go, but I want you to think about how you are gonna take my big cock inside of you for the first time. Trust me, it won't be the last time. I love fucking a tight hole like yours."

 

I sat there on my knees watching him leave. What just happened? This was insane. I cleaned myself up and got dressed for work. I had a rather boring job at the public library, but it paid the bills. I tried not to think about his cock, but that was futile. Plus, he was sending me texts. Then came pictures of his cock deep inside the ass of his wife with the words, "You're next" in the text.

 

After a couple days of this, I needed release. He was toying with me, and I couldn't take it. I wanted to suck his cock, but the next time he came over we just talked. The next day, I begged him to let me suck his cock. He just laughed and said I hadn't earned the right yet and to think about it some more.

 

So, I pulled out my trusty vibrator a few nights later. I needed to cum, and I had to work hard with that chastity device. I tried several positions, from sitting on top of it, to laying on my stomach. On my back with my legs in the air was the best. About 30 minutes later, I slowly came. It was intense, but I still needed more.

 

Later that night, I got a text. "You naughty little slut. I know what you did. I'd be mad, but you came the way a little sissy girl like you should cum. I'll be there tomorrow. Make me dinner. I'll provide the desert."

 

Wait. Did he have cameras in my house? The idea should have bothered me, but I didn't even care.

 

I made a meatloaf meal the next night, and he enjoyed it. I was happy to hear that. Maybe he would finally make an honest woman of me, or so I hoped. I didn't have to wait long. As I was clearing the table, be pushed me face down on the table and pulled down my panties.

 

He pulled my long brown hair and forced me to turn my head. "Beg me for it, Becky."

 

I hated the name Becky. I prefer Rebecca, but I knew he'd call me whatever he wanted. It was better than slut, or was it? I didn't know. I only knew I wanted his cock inside my sissy hole right then and there.

 

"Please, fuck me. Fuck me, daddy. I need it, badly." I spread my cheeks. "Fuck me."

 

He laughed. "See, I told you that you would be my sissy slut. I'm gonna enjoy this, and I haven't cum since you sucked me off. You're gonna be leaking when I'm done with you, and that's fine."

 

"Why's that, " I asked as I felt him push his head inside me? I winced.

 

He smiled. "Oh, you lubed up for me. Good girl. I like my girl to be prepared."

 

He shoved it in deep, and I screamed. "Oh God, that hurts. You’re so big."

 

He laughed. "That's it. tell the neighborhood you're being fucked in that sissy pussy of yours. Let them know you're my sissy slut."

 

I whimpered, but I pushed back against him. I wanted it all inside me. Once he felt I had relaxed, he started slowly fucking me. "When we're done here, I'm taking my sissy out for ice cream."

 

I looked back at him with his cock penetrating me deeply. "In my pink outfit?"

 

He laughed. "Why not? You're my sissy slut aren't you?"

 

I said nothing and he pulled my hair. "Yes, I'm your sissy slut."

 

He knew how to control the situation. In my encounters with men, I had never met a man who was so in control. I loved it. I was his sex toy. He was enjoying it just as much as I was. "I knew we'd be good together when we met."

 

After a few minutes, he had me on my back with my legs in the air as he went deep again. It wasn't long before I was leaking, and he noticed it. "You feel like you're gonna cum, don't you?"

 

"Yes Daddy, " I moaned.

 

He laughed. "You have my permission to cum like this anytime you feel it." He shoved it in deep. "Not that you have any choice in the matter.

 

I could feel the pleasure build and it wasn't long before I could feel him hitting me in just the right spot. I let loose and my body started to quiver. My clitty was leaking steadily and my bottom was clenching. "Hmm, " he said. "I love it when I make a girl cum, especially a sissy girl like you."

 

I was delirious with pleasure and could barely hear his words. "You know, my wife would have loved to have you in the bedroom with us. She talked about it, you now?"

 

The last comment shocked me. "What?"

 

That's when he tensed up and began to release his seed deep inside me. I've had a man cum inside me a couple times before, but it was nothing like this. I could feel my bottom being filled by him.

 

When he was done, he leaned down and planted the most passionate kiss on me with his cock still inside me. "You're mine now, you know that?"

 

I reached around his shoulders to hug him. "Fine with me."

 

He was serious about going to the ice cream parlor. I was not expecting that and I had a big wet spot on the back of my panties. I tried to keep it from getting on the back of my skirt, but I don't know how successful I was. I tried to fix my makeup, but I know I was still a sight based on some of the stares I got. Jim's lack of concern about the people around us set my mind at ease.

 

The next few nights, I prepared dinner for him at my house, and the fourth night, I did it at his house. That's where he surprised me by inviting his best friend Steve. Jim made it plain to me that I was to please Steve in any way he asked me to, and Steve had me sitting on his lap at one point after I brought him a beer.

 

Jim had bought me a sexy red lingerie corset outfit, complete with five-inch stiletto heels. The heels took some getting used to, but I managed. I could feel Steve's cock pressing against me. When we adjourned to the living room, Steve had his pants off. The next thing I knew, I was sucking his big cock with my ass in the air.

 

Jim took that as an invitation, and soon his cock was deep inside my sissy love hole. The sensation of taking two cocks inside of me is unlike anything I've ever felt before. I feel all at once like I'm doing something dirty and slutty, but I also feel the power. I love this sensation. I'm in charge of making these men cum, and I have to do it in such a way where I get off too. I love to cum with something inside me. Many times it has been with my toys, but Jim's cock is so much better.

 

I can taste Steve's cum, and I know he's close. I am too, for that matter. Jim has only taken my ass the one time, but he knows where to hit me. This is so hot, and Jim's talk makes it even hotter. "What do you think of my sissy slut, Steve?"

 

"She's good, bro. I'm about ready to cum inside that sweet little mouth of hers."

 

Jim laughed. "She likes that, don't you Becky?"

 

I take Steve's cock out of my mouth long enough to answer him. "Yes, I do, daddy."

 

Steve laughs and holds the back of my head on his cock. "In that case..."

 

The next few moments are intense. Steve starts shooting his cum inside my mouth. There's a lot of it too, but I'm doing a good job of swallowing. I'm close to cumming in my cage when Jim tenses up and shoves it in deep. Just as he starts to cum, I start leaking. The feeling is amazing. We're all cumming. The perfect scenario.

 

I'm cleaning Steve's cock when Jim pulls out. "Becky, go clean up the dishes and bring us some beers would you?"

 

I stand up and smile as I feel Jim's seed inside me. I kiss him. "Okay, baby."

 

I have no idea what's next, but a girl can get used to this. The last words I hear startle me again. It's Steve with a comparison comment. "She's almost as good a cock sucker as Emily, if you don't mind me saying so. God, I miss her. She was a special woman."

 

"Wasn't she, though, " I hear Jim reply. "I'll never forget the day you introduced us. Remember that?"

 

I guess some best friends really do share everything. Go figure. I guess that means Steve will be taking my bottom soon. Well, a girl can hope anyway.




If you enjoyed this story, check out Tales Of Daddy & Sissy Love HERE

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."

Advice For The Sissy Who Wants A Domme Wife

A sissy asks me the other day, "How do I get my wife to be more dominant?"

Um, lets see, how about you start by OBEYING HER.  That's at the core of the sissy handbook, you silly sissy.  Obey your Mistress.  She tells you to do something, don't argue with Her, do it.  She starts yelling at you, sit and take it.  This isn't rocket science.

Don't sit around there telling her to order you, you fool.  That's topping from below.  You want to please her, listen to what she is saying, and do what she asks.  Not, "I'll do this if you do that for me."

First, she must know that you accept that She is the one in control and get used to the idea.  So, you have to commit to it down to every detail, not just when it's convenient for you.  You're watching TV and she comes in and wants to watch something other than the game, give her the remote and sit there and watch whatever it is with her.

She starts talking about her feet being sore.  Offer her a foot massage.  She needs the dishes done, do them.  In the bedroom, do things Her way and put Her needs first.  Ask about Her day.  And listen to Her.  If she asks for your opinion or seems stuck, give her some advice in a friendly and non judgmental way, not like you know everything.  Be supportive of her.

She's going to see the change in you, and conversations may begin.  Tell her that you feel it is important that she be happy   Tell her sometimes you feel so unworthy of her and lucky to have her.  Tell her that her happiness is important to you, and that doing what it takes to please her makes you happy.

If the subject turns to the idea of dominant women, point her to web sites for Female Led Relationships.  Those generally show the merits of Her running things without hitting her over the head with kink she may not be ready for.  You can also suggest that if she wants to be more dominant in a D/s sort of way, you are ready to commit to that.  Suggest a few sites that explain what is it to be a Mistress.  But, let her look it all up and think about it.

If this rings a bell with her, She will let you know after her research.  At that point, she may want to have THE conversation, and that's when you get it in the open, agreeing NOT to judge each other for being honest.  You may hear things from her that shock you.  She may, for instance, like the idea of cuckolding, but that's not something you are comfortable with.

You may like the idea of sissification, and she's not crazy about that.  Can you see why a woman who accepts that her husband is a sissy and indulges that side of him may want to bring in a lover and cuck the little sissy?  No judgements.  If it gets to this point, there will be compromises before a commitment is made, or things may be thrown out or agreed to that aren't your preferences.

Can you handle all of that?  If you can, good for you.  Submit to Her and prove to Her you are worthy.  If you can't handle it, then why don't you just spank your little thingy to feminization porn and keep it a fantasy?  Because, if it gets to this point, chances are pretty good that your little thing is gonna be locked in chastity with the key on a chain around her neck.  Are you sissy enough to handle that ;)

Sissy Gina's new Job

 Sissy Gina's New Job

Sissy Gina looked at herself in the full-length mirror is her cute red top and black skirt.  Her smooth legs covered by panty hose and her feet in size ten, three-inch red stiletto heels.  "Tell me again why I'm working at a coffee shop, dear?"

Her wife smiled as she brushed the hair from Gina's blonde wig out of her eyes.  "Because you need a job, and I won't have you moping here like you've been doing."

Gina pouted, making her red lips look adorable to her wife.  "Okay, but why in these clothes?"

Darlene kissed her sissy on the cheek.  "Because, you are my sissy, and you are representing me.  I expect you to make me look good and bring home lots of money."

She grabbed Gina's name tag off of the dresser.  "See.  It says so right here, Miss Darlene's sissy Gina."

The sissy turned red.  "Honey, I can't wear that, and I don't think..."

Darlene glared at the sissy.  "Don't even try it, Missy, or I'll paddle your ass good.  You know better than that."

"I'm sorry, but do I have to wear the chastity cage?"

Darlene shook her head. "Sweetie, we've been over this.  That little clitty belongs to me.  I'm not letting it free any time soon.  Only real cocks can be free in my home, and I'm the one paying the bills now since your sissy ass got fired."

Gina sat down on the bed, “I know, but it wasn't my fault.  Mr. Davis saw my panties under the bathroom stall and..."

"I'm still disappointed with you over that, " she interrupted.  "If you'd have sucked his cock, you'd still have a good paying job right now.  You blew it."

Gina was shocked by the comment.  "Sweetie, he wanted to fuck my ass right there in the bathroom.  He said I would be his bitch if I wanted to keep the job and that nobody would hire me."

Darlene was condescending.  "Aww, poor baby.  You should have given it up, you stupid bitch.  You cost us a lot of money, and now that new house is on hold because you didn't want to do what a good sissy does."

The sissy looked at her wife desperately.  "Do you hate me?"

She laughed.  "What kind of silly question is that.  I don't hate you, but sometimes you can be such a stupid sissy.  You should have been more careful, and yes, you should have put out.  I just think you can be so ignorant sometimes.""

"But, I didn't want to be unfaithful to you..."

"Sweetie if you can get some cock, go get it.  You know how I feel about that."

Gina a knew well that Darlene had a few different boyfriends since she accepted her dressing up, and it still bothered her a little.  Being locked in chastity when in the room watching men fuck Darlene was even worse.  "I just don't know."

"Well, you'd better figure it out, because we need you earning your keep around here sweetie.  Now, you do exactly as Lexi says.  She is doing me a big favor by hiring you, and I will not be made to look foolish."


Lexi was a tall woman with short black hair.  If her look screamed Mistress, it's because she was a Lifestyle/Pro Domme.  She ran a chain of coffee houses, ten in all.  The businesses pretty much ran themselves, but she liked to stay occupied.  At night, she really let loose on the scene.

But, she was keeping a not too subtle secret.  Her coffee house in the city was visited by her clients and others looking for a good time.  Some of them had a penchant for sissies, and she thought an older 40 something sissy like Gina would fit in perfectly.

Gina barely set a foot through the door when Lexi greeted her.  "Gina, you're right on time.  Good girl.  Take this coffee to the black Cadillac out there in the parking lot and I'll punch you in.  Take your time, " she said with a wink.

Gina would soon learn what was expected of her as a black man sat behind the wheel of the car with his cock in his hand.  "Here you go, sir."

He smiled, “Leave it on the roof of the car, baby, and hop in the other side."

"Sir, I don't..."

He flashed a $100 bill.  "You're a pretty lady, and I just want to get to know you better.  Lexi knows I'm down for it."

He handed her the $100.  "Come on baby, don't be like that."

Gina's clitty was straining against the cage as she put the money in her bra and sat down next to the man.  "Put your lips on it baby.  I'm kind of in a hurry."

Gina was mixed about doing this, but Darlene made it clear she had better not disappoint her.  She put her mouth around his cock as he pushed her head down, causing her to gag.  ""There ya go baby, just like that."

Gina had no choice.  Every time she pulled her head back, he shoved it forward.  His taste was strong, and it didn't take long before he popped a big load in her mouth.  Unsure of what to do, Gina swallowed it all before her mouth even left his cock.

When she lifted her head up, he was shocked.  "Damn, baby, you swallowed it?"

She blushed.  "I...  Um ..."

He handed her another $20.  "I bet you have a nice tight ass too.  I'd love to have a shot at it sometime.  Maybe when I come back tomorrow."

Gina got out of the car with a strong taste of the black man's sperm in her mouth.  Then she saw the police officer out of the corner of her eye.  "Excuse me miss, I need you to step over here."

Blood rushed to her head quickly.  "Is there a problem officer?"

It was Officer Johnson, a regular of Lexi's.  He got certain favors from her to look the other way.  "Prostitution is a big problem in this city, miss, especially tranny hookers like you."

He cuffed her hands behind her back and led her to the dumpsters.  "Aren't you going to take me in, officer?"

He pulled his pants down, showing a nice six-inch cock.  "Maybe that won't be necessary, miss.  If you do what's right."

He helped her to her knees and soon she was sucking her second cock of the day.  "Damn.  If I had more time, I'd love a shot at that ass."

She tried to keep her balance as she bobbed on his cock with her hands cuffed behind her back.  He held a hand on top of her head and stroked his cock with the other.  "Yeah, like that.  I think a nasty little slut like you deserves a facial."

"But, it's broad daylight and I'm gonna look..."

He laughed.  "Not my problem.  Besides, every girl needs a facial now and then.  Good for your skin."  He started cumming.  "Yes.  Oh, take it baby.  All over that pretty face.  Oh."  He shot a big, dripping load, getting a shot in her eye and some on her chin.  She tried catching some with her mouth before he shoved his cock into her mouth again.  "Clean me up, slut."

He finished and uncuffed Gina while she was still on her knees.  "You better go back in and get your face cleaned.  You look like a dirty little slut."

Gina barely walked through the door before she was greeted by Lexi.  "What happened to you, dear?"

Gina frowned.  "A police officer took me behind the..."

"Oh, that's Officer Johnson.  Thanks for taking care of him.  It's one of the prices we have to pay to stay in business, unfortunately.  Did Tyrone take care of you?"

Gina handed her the $100, and Lexi smiled.  "Good girl.  We'll settle up at the end of the day.  I don't ask for any of my girl's tips, but I get my cut of the fee.  Go clean up and I'll show you around the counter."

Gina was about in tears as she washed her face and reapplied her makeup.  The bathroom door opened.  She thought it had been locked.  It was a tall, bald headed guy named Scott.  He locked the door.  "Gina told me you'd be in here."  He handed her two $100 bills.  "I want a shot at that ass.  Just bend over the sink.  That will do."

"I can't do..."

He grinned.  "Oh yes you can, darling.  And you have no choice.  You're on the clock."

She slowly assumed the position.  He laughed.  "Never been fucked before?"

She shook her head.  "I'll let you in on a little secret.  I've been fucking your wife, and she loves this cock."

Gina turned her head. "You what?"

She felt his cock penetrate her ass in one push, and she screamed.  He held it there for a moment.  "Yeah, I thought it would be hot to fuck the little sissy who can't satisfy a beautiful woman like Darlene."

He smiled as he felt her tight ass around his cock.  "That's what I thought.  It's about all you're good for."  He started steadily fucking the sissy from behind as her pain gave way to pleasure and she pushed back.  "Oh, you like it don't you?"

"Yes, " was all she could manage as she pushed back.  Part of Gina was disgusted with herself, and the other part didn't care.  What happened next was another first.

"Oh, " was all Scott managed as he began to shoot his load deep inside her ass.  "Yeah, that's it, baby.  Take my load, just like your wife."

When he was done, he pulled out.  "You didn't use a condom, " She said as she felt some of his cum leaking out."

He smiled.  "Yeah, sorry about that.  Here, " he threw another $100 bill at her and kissed her.  "For your troubles.  It was worth it, darling."

Lexi came to the bathroom to get Gina.  "What's wrong?"

"That man...  He...  He raped me and came in..."  she sobbed.

Lexi grabbed the money and hugged her.  "Sweetie, no, he paid you for all of it.  That makes you a sissy whore, not a rape victim.  I think you did great."

Gina learned the ropes at the shop and was a quick study.  She actually came home with over $400 for her first day, not counting another $60 in tips.


When Gina walked through the door, Darlene was waiting for her.  She walked past her after handing her the money.  Darlene didn't count it.  "Sweetie, what's wrong?"

"I met your boyfriend today, " she said as she entered the bedroom.

Darlene followed her. She giggled.  "Which one. dear?"

Gina sat down on the bed.  "Scott."

Darlene smiled.  "Oh yeah, Scott.  He's a bit of a perv, but a real good time.  How is he?"

Gina could barely look at her wife.  "He fucked my ass and came inside me."

Darlene gasped.  "Oh my God.  He said would love to do it, but..."

"He's an asshole, but I see what you see in him."

Darlene sat next to her sissy.   "Oh?  What's that?"

"He's got a big cock, and he definitely knows how to use it."

The hot wife laughed as she hugged Gina.  "Isn't that the truth?  My God, he can hit me in just the right spot."  She stopped and looked at her sissy.  "Sissy, what's wrong?  If you don't want to go back..."

"No, " said Gina as she stood up and looked at herself in the mirror, realizing there was still a cum stain near the top of her blouse.  "It's not that.  You were right.  It's just..."

Darlene was trying to figure out what was wrong.  "I was right?  About what?"

Gina removed her blouse and skirt and was down to bra, panties and panty hose.  The spot on the back of her panties was noticeable.  "I'm a sissy, and I need to accept what that means"

Darlene slapped her sissy's ass.  "The wet spot on the back of a girl's panties never lies."

"Yeah, " said Gina as she kissed her wife.  "But I should have given it up to my boss right then and there."

Darlene hugged her.  "I'm so glad to hear you say that, because I've been talking with him, and he's coming over here tonight in about three hours."

"What?"

She grinned at her sissy.  "Sweetie, I said I have boyfriends, as in more than one.  I've been fucking him for a while now.  He wants a shot at your pussy, and I told him I'd see what I could do.  If he were willing to hire you back, full time female this time..."

"Oh shoot, " said Gina as she rushed to the bathroom to draw a bath.  "Only a few hours to get ready, and I'm a disgusting mess."

Darlene proudly looked at her sissy.  "That's my girl.  I'm gonna turn you into a proper slut yet."

Gina laughed.  "Well, it takes one to know one.  I have the best teacher."

A Sissy's Encounter With The TSA

 A Sissy's Encounter With The TSA

Sissy Jillian finally got a look at the lower back tattoo Mistress had her get and was starting to cry. It had the words Insert Sperm Here on it with an arrow pointing down to her pussy hole. "How could you do this to me, Mistress?"

Mistress Abigail shook her head. "I did it for you, my pet. You've been doing so well in your training and have accepted your new role here. I thought that this was better than some boring butterfly tattoo. We can get one of those for your arm maybe."

"But, I'm not gay. " The sissy protested. "Now, if somebody sees this, they're gonna think I want to be fucked."

Mistress laughed. "First of all, if somebody sees it, chances are that you are about to get fucked. Secondly, whose pussy are you gonna get? Not mine, unless you're eating it. Furthermore, your locked up clitty won't be fucking anybody, not that it was ever good enough to begin with."

The sissy put her head in her hands and cried. "How could you?"

Abigail finally had enough. She reached for her paddle. "You know what? That's it. Assume the position, right now."

"But..."

"I said right now, " Mistress knew she had to be assertive. "You heed to learn your place."

The sissy reluctantly got on her hands and knees after lifting up her skirt. She felt the sting of the paddle five times and started crying. "I'm sorry Mistress."

"Damn right you're sorry, you ungrateful little bitch." She swatted her three more times. "I decide to give you the gift of a pretty tattoo in pink and black like you wanted, and you act so ungrateful."

"I'm sorry Mistress, " the sissy sobbed.

"That tattoo is gonna make the guys so horny when I have you serving them drinks at my party next month, and I thought you'd love it. But do I hear any gratitude?"

She paddled her ass hard another five times. "I'm sorry. Thank you, Mistress. I don't deserve you."

"That's right, you don't, " she replied, and she dropped the paddle on the bed. "Sometimes I don't know why I even bother with you. So ungrateful after all I do for you."


Jillian wept on the floor. "I'm sorry Mistress. I'll do better, I promise. I love you."

Abigail laughed. "Of course, you do. You'd better love me, you bitch!"

Abigail did love her sissy sub, but she got a big thrill out of the punishment aspect of their relationship. She knew her sissy craved all of it, but she didn't know how much she would enjoy it. She had invested a lot of money in stuff to put her sissy in her place.

Jillian actually made pretty good money as a free-lance writer and had written a successful romance novel with two more on the way. All of that money went to Abigail. It was agreed that all financial decisions would be made by Abigail.

The sissy was getting used to dressing full time, but she was very nervous about the flight she had booked for a special romance novelist convention that her publisher expected her to attend. He knew about her dressing, but she had never dressed in his presence. This would be the first time.

Mistress took her sissy by the hand. "Come here. I think it's time you went to bed."

"Yes Mistress."

She led her sissy to her bedroom, which was almost like a little girl's room with lots of pink and pictures of princesses on the walls. She made sure her sissy dressed in her pink nightie and panties. Then, she proceeded to restrain her to the bed and blindfold her.

She smiled and kissed her sissy on the cheek. "There. All safe and secure. I'll check on you in about six hours to make sure you're not in pain from the tattoo. You may need more meds."

She walked to the door and turned around. "Oh, I've decided you will remain in chastity for your flight. You need to be taught another lesson."

Jillian panicked. "But I can't. What about the TSA?"

Mistress laughed. "The TSA will be okay with you. You just need to explain things. You may need to go to the private screening room, but that's okay."

"But..."

Abigail took the ball gag from the stand and placed in on her sissy. "That's about enough out of you, Missy. Now go to sleep."

Jillian was nervous. Mistress not only forced her to remain in chastity, but she also ordered her to wear a pink butt plug on the flight. She could have just broken out of the chastity and removed the plug, but she didn't want to risk it. Mistress would punish her good for her disobedience.

She wore a short sleeve baby blue dress over a smooth figure shaping corset. The dress came down to her knees, and the black boots she wore came just up to her knee. Fully made up with her medium length black hair in a page boy style, she walked through the airport.

She had checked in her one bag, while dragging a pink carry-on bag behind her. She knew everything about her screamed sissy, and she dreaded trying to go through security.

The female agent looked at her ticket and laughed. "Jack Johnson?"

The sissy blushed. "I'm Jillian, " she replied in her best female voice. "Jack is my male name. I'm transgender."

She didn't look all passable to the agent, but she had been given sensitivity training on the matter. "Okay, go on through."

Another hurdle cleared, but now came the scanners. This was the part she dreaded. She removed all of her jewelry and opened her purse up before setting it in a container. Her boots were next. Then, she removed the laptop from her bag and placed it in a container with her smart phone.

She nervously entered the x-ray scanner with her arms over her head. As anticipated, a warning sound went off. A female African American TSA agent spoke to her her. "I'm gonna have to ask you to come to the security room."

Jillian blushed. "It's a chastity device. My Mistress made me wear it, and... um... a plug too."

The agent stifled a laugh. "Plug?"

Jillian couldn't remove the red from her face, even with the best makeup. "Butt... Butt plug ma'am."

"Oh, " she said with a grin. "In any case, I'm gonna have you ask you to follow me."

There was a little room not far from there, and the agent led the sissy in before turning around. "Joe, could you get those three containers and bring them here sweetie? Thanks."

She shut the door behind her. "Am I in trouble, ma'am, " Jillian asked nervously.

"Maybe, " she said with a grin. In reality, the agent had experience in the BDSM lifestyle. "What's your name?"

"I'm Jillian ma'am, " she replied, extending her hand to shake hers.

The agent shook her head in amusement. "Cute name. I'm Renee. You may call me Miss Bailey."

Joe entered the room with the containers. "This one has a smart phone and a laptop. Let me take a look at that laptop."

Miss Bailey grabbed the smart phone. "You do that. We can't be too careful in this day and age." She turned to the sissy. "I'm gonna have to ask you to strip down to your panties and bra..."

She paused for a moment. "You are wearing a bra and panties, right? What am I saying, I bet you're in a sexy pink lace bra and panties. You know, on second thought, strip naked."

"Miss Bailey, I don't think I have to do all of that. It's just a chastity..."

The female agent was starting to feel her dominant side coming to the forefront. "I didn't ask you what you thought, Missy. I said strip down now, or you will be in bigger trouble."

Jillian slipped out of her dress to reveal the pink bra and panties and corset. "What did I tell you? She's in cute sissy lingerie."

Joe laughed along with her at the revelation. "Um, Renee, take a look at these pictures."

Renee glanced over at the computer to see photos of sissies being put through their paces by a Mistress. "Oh my. What have we here?"

"It's just porn, " Jillian explained as she removed her corset. "It's all legal stuff."

Renee laughed. "Yeah, I'm sure. Who is Abigail?"

The sissy couldn't hide her embarrassment, but her chastity device kept her excitement from showing too much. "She's my wife.... I mean Mistress."

Joe was laughing. "Oh, I gotta tell Darnell about this."

Miss Bailey shook her head. "Only Darnell Joe, let's not create a scene here. Well, a bigger scene than we already have."

She typed a text to Mistress Abigail. "This is Miss Bailey. You have a pretty sissy here Miss Abigail, but she triggered our alarms with her chastity device and butt plug. What do you suggest we do about her?"

Jillian stood naked in front of Miss Bailey. "What do you want now?"

Renee walked around the sissy and touched the steel chastity device with her white latex glove. "All snug and secure I see."

The smart phone buzzed with a message from Abigail. "This is Miss Abigail. Do whatever you think needs to be done to my naughty little sissy, you have my permission."

Renee laughed. "Oh my God. You are in trouble now sissy."

Jillian started to get frightened. "What? What happened? What did I do?"

The female agent walked to the sissy's carry-on bag. "If I open this, I'm not gonna find any naughty toys, am I?"

Jillian blushed, and Abigail had her answer. Joe returned to the room. "Darnell will be here in a minute."

Jillian pulled out a six-inch blue dildo. "Perfect. Lock the door. He'll knock when he's here."

Joe locked the door and Miss Bailey stuck the dildo in the sissy's face. "Wanna explain this to me?"

"I... Um.... My Mistress made me bring it so I could practice, ma'am."

She grinned. "I told you, you may call me Miss Bailey. It seems your Mistress has given me permission to do whatever I need to do, and I think you need to show me what you do with this toy."

"But, ma'am, I..."

She slapped the sissy in the face and sat down in her chair, holding the dildo between her legs. "Show me what you do with this toy, sissy."

Jillian stood there and Miss Bailey ordered her again. "Show me what you do with this toy, or you will be punished."

Jillian knelt between her legs and started sucking on the dildo. "That's what I thought, " said Renee. "We have a sissy cock sucker on our hands."

Joe noticed the bandages on Jillian's back. "Hey, what's that? Did you get hurt?"

"It’s probably nothing Joe, " said Renee. "Just relax. Maybe I'll have the sissy give a demonstration on you next."

Jillian was relieved that the tattoo was not revealed to anybody. Then, she heard the phone buzz again.

"Be careful with the bandages on my sissy's lower back. I just got her a tattoo, and I don't want it getting infected, " read the text from Abigail.

Renee laughed as the sissy kept sucking her dildo. "What kind of tattoo did you get sissy?"

Jillian blushed, but her head being impaled on the dildo hid her expression. "Oh, it's nothing."

Joe stood up. "I want to see."

Renee grinned. "Go ahead and look, just be careful with the bandages."

Joe slowly peeled it off to reveal its slutty message. "Oh my God."

Jillian stopped and was admonished by Miss Bailey. "Did I tell you to stop sucking, Missy? Keep going before I spank that ass good."

Joe laughed. "From the looks of it, she's been spanked pretty good already."

"So, what's it say, Joe?"

He was still chuckling. "Get this, it says insert sperm here and points to her ass."

Renee grinned. "I like a sissy that cones with instructions."

She stood up and motioned to Joe. "Take your pants down Joe and give this sissy a nice cock to suck on."

"But, " Jillian tried to protest, only to get spanked on her still sensitive butt cheeks by Renee's hand.

"I didn't say you had a choice sissy, " Miss Bailey asserted. "Suck his cock now. You're about ready to show me what else you do with your toy."

Joe willingly sat on the chair. "Okay sissy, suck my dick."

Jillian reluctantly began sucking his cock. She had never sucked a cock before, only her Mistress's strap on. However, she understood what needed to be done."

Renee pulled the pink plug from the sissy's pussy hole and then inserted the vibrating dildo at medium pulse. "This is the advantage of plugging a sissy right here."

Joe laughed. "You've done this before, Renee?"

"Damn right I have, " she proudly proclaimed. "In fact, this little sissy right here is making me want to get a sissy of my own again. From the looks of things, Joe, you're not well endowed. I could train you if you want."

He was enjoying the way Jillian took his cock deep down her throat, gagging a little. "Fuck no." Jillian continued sucking.

"Come on, what's not to love? Plugged all the time, locked in chastity so you can't cum unless I milk you."

Joe said nothing. Renee worked the dildo inside Jillian's pussy, being careful to hit her in just the right spot. She was quite efficient at giving sissies orgasms this way in the past, and she used to make pretty good money as a Pro Domme doing this sort of thing. "How does that feel sissy?"

There was a knock on the door, and Renee shoved the dildo in deep before going to unlock it. It was Darnell. She opened the door and let him in before locking it. "Hey baby, I found us a sissy."

The bulge in his pants told the story. "I know, I had to shut off the camera in the other room and delete the recording. Girl, you got to be more careful."

"She's loosened up for you and she comes with instructions."

Darnell looked at the tattoo. "Oh fuck. I can do that, " he looked at Joe. "She any good at sucking cock?"

Joe grinned. "Oh yeah."

He looked over at the table. "Lay that bitch on the edge of the table. I have an idea."

Joe helped Jillian up and led her to the corner of the table with her back on the table. Her ass was at one end and her head hung over the other. "Perfect, " said Darnell as he stuck his hardening eight-inch black cock in her mouth. "Suck it baby."

Joe stood on the other end. "Mind if I have a go at her ass?"

"Fuck the sissy's pussy and lube her up for me, She gon' get stretched in a minute, " Darnell laughed.

Renee looked at the plane ticket. "You're gonna miss your flight, but we can put you on a later one. Will that hurt your plans at all sissy?"

"Nuh uh, " was all Jillian managed with a mouth full of Renee's boyfriend's cock.

"Good, " I'll set that up from here. "I think you need to learn a valuable lesson about trying to be sneaky with airport security."

Joe shoved his cock into Jillian's virgin pussy and began steadily fucking her. She was lost in a wave of emotion. How could Mistress let this happen to her? This was so cruel, even for her, but why did she like being in this vulnerable position so much?

Mistress had always talked about pimping her out to guys, but it was bedroom talk, or so the sissy thought. When she had that tattoo put on her, she began to realize that Mistress had other plans for her. This moment, lying on the table taking cocks at both ends, drove the point home.

Joe was fucking her steadily, and she found herself squeezing ever so gently when he pushed in. It wasn't long before he released his seed inside her formerly virgin pussy. "Oh, fuck yeah, " Joe proudly proclaimed.

Jillian was starting to taste hints of Darnell's cum when he pulled his rock-hard cock out of her mouth. "My turn, sissy."

His cock slid right in, though it was a tight fit for his girth and a good two inches longer than Joe's as well. "Yah see, Joe, this is why I like seconds. Gets a sissy's pussy ready for my big cock. Then I can pound that pussy good.”

Renee brought the dildo back to Jillian's face. "Suck it, sissy. Taste your pussy on it."

Jillian sucked as instructed. She knew this might not be right, but she had surrendered to the moment. She was now a full-fledged sissy slut, and her life would never be the same.

Miss Bailey looked at the sissy's face. "You like that big cock inside you, don't you?"
"Uh huh, " she moaned.

"Gonna let you in on a little secret. Darnell knows how to make a sissy like you cum, even if they're locked up."

"Oh God, " was all she managed as she was lost in a wave of pleasure."

Renee shoved the dildo back in her mouth. "I didn't tell you to stop sucking, bitch. Damn, I wish I had my strap on."

"Damn, baby, we need you go back to storage and get your stuff out. I think we need another sissy for our own. This bitch is tight, " Darnell was fucking her hard and deep, and she was talking it like a pro.

She smiled "I think your right."

As Jillian felt an orgasm build up, she was encouraged by Miss Bailey, "Let go, sissy. Cum for us. You know you want to."

"I can't, " Jillian replied.

"Yes, you can, " the female agent in insisted. "Stop thinking like a man and think like the sissy you are. A big cock in your pussy makes you cum. Don't fight it."

This talk drove the sissy over the edge. She started feeling her orgasm build and cum started leaking from her caged clitty. The feelings went on for a while as she enjoyed her first anal orgasm from being fucked by a guy. Mistress had given this to her with a strap on before.

"Here come the waves sissy, take it, " Darnell proclaimed as he erupted inside Jillian's pussy. When he was done, he moved back to her mouth. "Clean me off slut."

Renee put the plug back inside the sissy's hole. "Don't want to let any of Darnell's cum leak out of you now, do we?"

Jillian felt like she was in another world, "No ma'am."

"I gotta go back to my station. Get this bitch dressed and get her out of here, " Darnell said as he kissed Renee. He and Joe excited the room with the door still locked behind them.

"Get dressed. " Miss Bailey instructed as she texted Mistress Abigail once more. They exchanged texts the whole time the sissy got dressed.

"Okay, here's the deal sissy. You are on flight 108, which will leave in a couple hours. Your Mistress said you already have a motel room and the convention isn't starting until tomorrow morning."

Jillian looked down, still ashamed of herself. "Thank you, Miss Bailey."

Renee smiled. "No need to be ashamed of what you just did, honey. Lots of sissies are proud of doing this, and you were great. In fact, your Mistress says you will be flying quite a bit and locked up like the sissy you are. I told her to send you to us and we'll take care of you."

Jillian blushed. "Thank you, Miss Bailey."

"Fix your lipstick, Missy"

Jillian grabbed her lipstick and compact mirror and reapplied the shade of red she wore. She felt so dirty, but still turned on.

Renee handed the sissy her smart phone. "You now have contact information. Darnell and I would love to have you over some time, and your Mistress has invited us for a visit in a few weeks. I think we may just take her up in it."

Jillian left the room feeling violated, used and abused, but still turned on. She would make it to her destination on time, but this encounter had changed her. If she didn't understand where she stood with her Mistress before, she did now. She was her Mistress's sissy slut.

"I'm a sissy slut for Miss Abigail, " she thought to herself. "I can never be her man again. I am just a little sissy in chastity." She realized she was smiling at that thought. "I am so lucky."