Gary GingerChapter 4
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Cat...chapter 1 free porn video
It started as an offhand comment by a friend. He'd intended it as a derogatory, but it stuck in Jason's mind, a little seed that slowly sprouted. When the tiny voice in his head became too loud, the internet searches started. Then came the porn. Eventually, more research revealed that Brazilian tranny videos didn't accurately reflect the truth. True transgender people struggled greatly, both internally and externally. Curiosity about those struggles only fueled his desires. Now, he just needed to figure out how to address those desires.
He entered the bar and looked around. He wasn't quite sure how to go about it, but the articles had stressed being honest and forthright. Well, nothing to do but dive in, he said to himself. There was a single woman seated at the bar. Jason walked up to her and cleared his throat. She glanced at him sideways but said nothing.
"Hi. Um..." He cleared his throat again. She looked at him with mild annoyance. "Um...are you...um...transgender? A transgender woman?"
She looked at him, glancing up and down, taking him in. He was clearly extremely nervous, his hands shaking slightly and a bead of sweat at his hairline.
"Oh, you're one of those. We get you guys in here from time to time. I'm gay, but if that's what you're looking for..." She looked around. "See that woman over there with the silver hair? That's Cat. Word has it she likes breaking in you newbies. Go talk to her."
Jason looked around. She was at the far end of the bar engaged in animated conversation with another woman. "Silver hair? Is she old?"
"No, it's a dye job. It's an in thing right now, but she's done it since before then. Now leave me alone so I can get drunk and forget about my girlfriend cheating on me."
"Oh, sorry."
The woman just waved him away and returned to her drink.
Jason walked over and sat on the empty stool next to the woman called 'Cat'. He ordered a drink, nursed it and waited for the women to stop talking. Eventually, the other woman got up and left.
"Are you going to keep staring at me out of the corner of your eye, or do you want something?"
"Er, um...I...that is..." Jason stammered, flustered.
"Come on. Spit it out."
"One of the other ladies said that you might be a transgender woman?"
"Yes, I am...and?"
"I, uh...was, uh...wondering if you might have sex with me?"
Cat looked at him hard, her eyes narrowing. She absorbed him, sizing him up, looking at everything about him, even his demeanor and posture. She guessed him to be early twenties, meaning he was probably inexperienced either way. Unless they'd been taken in under the wing of someone much older, they simply hadn't had enough time to get good at sex. Many didn't even have a clear idea of who they themselves were.
"Let me guess. You're gay but still in the closet. You want to dip your toe in the water, but imagining a guy's face while you're doing it freaks you out?"
Jason looked slightly confused. "No, I don't think I'm gay. I just thought...that is...I...I was curious..."
"Oh, I get it. You're a fetishist, but you're also a newb."
"Uh, I, um, I'm sorry if I offended you."
"No, no offense. Hmm..." Cat looked him over again. On one hand, she really liked breaking new people in. It was her favorite thing to do. On the other, it took time to do properly and it was already late. She preferred to start early in the day. Cat thought of herself as one of those rare teachers who took a special interest in a promising student and provided them with the knowledge, resources, and encouragement to help them reach their full potential. Quite a few others thought of her as some kind of weird freak by any standard. There were wild rumors surrounding her and stories that couldn't possibly be true. However, even her greatest detractors had to admit that no one who'd been with her ever had a single unkind word to say. In fact, they never said anything except that it had been "wonderful", "incredible", or "amazing". One had even used the word "heavenly". Cat never acknowledged the dark looks she sometimes received, though it always made her smile.
"You clean? Any diseases or stuff?"
"No, no diseases or anything."
"First time, right?"
"Yes."
Cat stared at him silently for a couple of minutes. He appeared to be about the same height as her and slightly pudgy. His skin was slightly darker than caramel, but green eyes belied a mixed race heritage. Objectively, he was mildly good looking at best, but it was the eyes that drew you in. He had very, very pretty eyes. She turned it over in her head as she studied his face. He made her think of a lost puppy. Against her better judgment, she nodded.
"Alright. Let's go. You can follow me back to my place."
Jason followed Cat to her apartment. As soon as the apartment door was shut, Cat grabbed him by the collar, slammed him into the door, then pulled him in for a kiss. She shoved her tongue into his mouth, swirling it all around, even licking his teeth. "I'm not some dainty girlie girl. I know what I like and I'm not shy about it. I also like to be in charge." She studied his face for a moment. "You sure you want this? You can leave right now. No harm, no foul."
"Uh, yes, I think I would like to stay," Jason stammered.
"Alright, some ground rules then. First, pay attention to what I say. Use the words I use. If I tell you to do something, you do it. No hesitation. If I tell you not to do it, you don't do it. Capice?"
"Uh, uh, yes, ma'am."
"Just call me Cat. If you're into pain play, bondage, diapers, or whatever, we're not doing that tonight. This just going to be basic 101 stuff. Okay?"
Jason nodded.
"I know you said you're clean, but unless you have some recent test results in your back pocket, we're both using condoms."
"Both of us?"
"Yeah, both of us. This isn't just about you. I'm going to have my fun as well."
"Uh, okay."
"Alright. Bedroom's this way." Cat turned on her heel and headed down a short hallway and disappeared through a door. Jason hurried to follow after.
The two stood face to face and Cat kissed Jason aggressively again, then stepped back.
"You're probably wondering what I look like."
Cat rapidly undressed and took another step back, letting Jason look at her. She slowly turned around giving him a 360-degree view. Cat's face was pretty, but not much more so than any other woman. There was a certain perfect symmetry to it that made your eyes linger. Her eyebrows were dyed to match her silver hair and her make-up was light. Her body was the color of Carrara marble. Her arms were slightly muscular, as were her legs. Her breasts were small, perhaps an A cup, and nicely shaped. Her stomach was smooth and slightly muscled as well from daily workouts. Her pale blonde pubic hair was neatly trimmed and an average sized penis hung down with heavy looking testicles behind it. Giving him a moment to look her over, she tilted her head, shifted her stance, put a hand on her hip, and turned slightly to present an oblique angle.
"I'm going to give you one more chance to back out."
Jason shook his head.
"Alright then. Remember that I did try to be merciful."
She smiled like a dangerous predator. A tiger stalking prey. He looked a little scared, but set his jaw and stood his ground. Potential, she thought.
"Now, your turn. Get undressed so I can see what I'm working with."
Jason didn't undress. Instead, he stared at Cat's body, looking up and down repeatedly. He took a hesitant step forward. "Can I touch it?"
"Heh," she laughed. "Go ahead."
Jason took another step forward and reached out to take her penis in his hand. He felt the silky texture and rubbed his thumb back and forth across the tip. He slid his hand up and down, fascinated. It seemed all the more beautiful for being attached to a woman. It began to stiffen in his hand. Without thinking, he stroked it gently. It firmed up fully and throbbed slightly within his grip. He felt a bit of relief that it was no bigger than his own. He'd seen some videos and was concerned that it might be very large. He tore his eyes from it and looked up to Cat's face and back down again. He reached out and touched a breast, pulling his hand back, then touching it again. Cat had seen this before and waited patiently.
After a minute, Jason spoke. "Uh...um...can I...uh...?" The tip of his tongue appeared between his lips.
She laughed. "Want some girl-cock, huh? Your mouth is watering and you're imagining what it tastes like? Alright, come over here."
Cat walked over to the bed, as graceful as a leopard, grabbed a pillow and dropped it on the floor. She sat on the edge of the bed, her legs spread wide. Leaning back slightly on one arm, she waved him over. "Kneel on the pillow." Jason was on his knees in a flash.
"You ever sucked one before? Girl-cock or boy-penis?"
"No, ma'am...er...Cat."
"Mouthed a dildo?"
Jason shook his head.
"Cucumber? Anything?"
Jason shook his head again.
"Complete virgin. Okay, here's what's going to happen. I'm going to talk you through it. Do what I tell you and you'll enjoy yourself. Certainly, more than I will. You got balls, so remember that they're sensitive when you're working them. Now, kiss it."
Jason puckered his lips and kissed the top of her glans.
"No. On the shaft, about halfway down."
Jason kissed Cat's girl-cock again, then opened his mouth.
" Ah ah." Cat smacked him lightly on the top of the head. "Remember, do what I tell you. Now, put your lips to it again, like you're going to kiss it, but leave them. Just let it rest there." Jason brushed his lips to her and remained in place.
Cat squeezed, flexing and relaxing the muscles in her pelvic floor. Her girl-cock raised sharply then dropped to bounce against his lips. Jason didn't move. She did it again, arching her eyebrows. Jason remained still.
"Good boy. First of all, don't just inhale it and gobble it down. You want to start slowly and build up. You want it to be enjoyable for both of you. Yes, it can be fun to jump in zero to sixty or be a little rough. But like I said, we're just going to stick to the basics. Now, gently take hold of it..."
Cat started Jason out with the basics giving good head. He proved eager to learn and followed her instructions exactly. He also turned out to have a pretty agile tongue. Hmm...not bad, Cat thought. She started guiding him to her specific preferences. Jason was an apt pupil.
"You're doing good, Jason. Now, I want you to improvise."
Jason continued to follow the last instruction she had given him.
"Improvise, Jason. I want you to experiment and have fun doing whatever comes to mind."
Jason sat back and looked at Cat's girl-cock with a bit of consternation. Cat flexed a couple of times, causing it to bob up and down. "Come on, Jason. Don't leave a girl hanging."
Jason took her back into his mouth and began trying different things. He quickly got into it, showing creativity, even adding flourishes. Pretty damn good, she thought. Cat relaxed back on her elbows and closed her eyes.
"Jason, I'm going to put my hand on the back of your head and fuck your mouth. Keep your lips closed firmly, but not too tight. Keep using your tongue like that."
Her eyes still closed, Cat wove her fingers in Jason's hair and pushed his head down firmly. She repeatedly humped up, sliding in and out quickly. She gave him a couple of minutes of mouth fucking. He's lying, Cat thought. She knew that there was no way a beginner had this kind of talent.
Cat opened her eyes and pushed Jason's forehead back, forcing him to release her. She bobbed freely, tapping his lips, nose, and cheeks. "You're doing great for your first time, Jason. Now, do you want me to come in your mouth?"
Jason watched her girl-cock sway, almost hypnotized.
"It's okay to say no. I can come on your face or just wherever."
"I think I would like it in my mouth."
"Good choice. As I'm sure you know, orgasms are pretty much the best things ever and your body isn't fully under your control when it happens. I'm going to want to push forward deeper into your mouth. When that happens, I'm going to poke the back of your throat, perhaps kind of hard. I might even go down into your throat a little. Since you're inexperienced, you're probably going to gag. I don't want you spitting up on me or vomiting on my lap. So, what you need to do is hold the shaft firmly and pull your head backwards as I move forward. Try to keep me in the middle of your mouth. Do you understand?"
"I think so."
"Good. Let's give you your first taste and then we'll have some fun getting you off." She flexed again and Jason took her back into his mouth. "You've got decent tongue action." She was downplaying just how good it was. "Focus on the crown and pump my shaft fast. Give it just a little twist one way at the base and the opposite way at the top. Yes, just like that. Yeah, mommy like. Mmm...nice. That...do that faster. Keep going, I'm almost there. Yes. Really good, Jason. Mmm...get ready. Shit, yeah, fuck..."
Cat's orgasm was much better than she had expected. Her hips came off the bed and she had to fight not to grab Jason's head and shove it down on her pole. Just as she had said it would, her girl-cock jammed into the back of his throat. Her hips jerked forward pushing deeper. Jason gagged, but wanting to do a good job, tried his best to suppress it. He gripped her shaft firmly and pulled back trying to keep her in his mouth as she jerked and twitched.
Cat had forgotten to warn Jason about just how much she was going to come. Cat's ejaculations were prodigious, her loads considerably larger than anyone else she had ever been with. Jason's cheeks ballooned slightly and a trickle formed at the corner of his mouth. Cat noticed through fluttering eyelids and struggled to speak. "Swallow, Jason. Just keep swallowing. It'll stop in a little bit." Jason nodded a tiny bit and swallowed continuously. Several more contractions rippled along her length, continuing to fill his mouth.
Cat's orgasm subsided and she ruffled her hand through Jason's hair. "Run your tongue around your mouth and get a good taste." She smiled broadly. "Great job, Jason. Really good." If he's really a newbie, then he's a savant, Cat thought. Jason still held her in his mouth, his eyes gazing up at her, enjoying the praise. "Put the tip of your tongue in my slit and wiggle it like you're trying to get inside. Move your hand to the base and make like an 'ok' sign. Now, squeeze a little and pull upward, so that you're milking anything left into your mouth." Jason milked the last bits out of Cat and she patted his head. Jason sat back and looked up at Cat. She stroked the side of his face gently. "Wonderful job. Really." Jason positively glowed. "Okay, let's take care of you. Get undressed and on your hands and knees on the bed."
"I...uh...never sucked a penis..."
"Girl-cock," she corrected him.
Like many people with a non-traditional view of sexuality, Cat had her preferred terms. A phallus was a girl-cock or boy-penis, depending on how its owner presented themselves. Similarly, most people presenting themselves as more male or with a masculine dominant aspect were 'boys', though they might sometimes be referred to as 'guys' or 'dudes' in third person conversation depending on their perceived maturity level. Female or feminine dominant presenters could be 'girls' or 'women', also depending on experience and perceived maturity. These latter terms applied independently of their subject's sexual organs. Some tried to present themselves neutral or a homogenization, but there was always something that steered her one way or another. If that person expressed a desire for their own terms, she would respect that and accommodate them.
"What?"
"I have a girl-cock. You have a boy-penis. Say it."
"You, uh, have a girl-cock. I have a boy-penis."
"That's right. Now, what were you going to say?"
"I never did that before."
"Well, you did a fantastic job. Did you enjoy it?"
"Yes, it was fun. And then when you...uh... I liked it. It was really thick, but it tasted good. There was so much. I can still taste it."
"Good. I promise you'll enjoy everything we do tonight."
Jason undressed slowly. There was trepidation in his voice. "Are you going to fuck me in the ass?"
Cat smiled and gave him a peck on the cheek. "Yes, Jason, I am, and when I do, you'll enjoy that too. But just because you'll like it, it doesn't make you gay, if that's what you're worried about. That has nothing to do with being gay. Try to relax and don't worry about it right now. We're going to do something else instead and I promise you'll love it. Now, get on the bed."
"I...uh...read something about safe words..."
"Those are only necessary if you're not fully committed. Are you fully committed, Jason?"
"Uh..."
Cat's voice hardened. "Leave. I don't deal with c***dren."
"No! I'm committed! Fully!"
Cat's voice softened and warmed. "Excellent, Jason. I believe that I told you to get on the bed."
Jason scrambled to get on the bed.
Cat opened the top drawer of the dresser. She grabbed a finger cot and reached for her preferred lubricant. "Are you allergic to silicone? I have water-based too."
"I don't have any allergies that I know of."
Cat moved over to the bed and put on the finger cot. "Jason, I'm going to rub your anus. I'm just going to use my finger. I'll be using a great lubricant, so it'll be nice and smooth. I want you to relax as much as you can. Just take deep breaths and focus on the sensation and how good it feels." Cat used plenty of lube, coating her finger and Jason's anus. She could see his sphincter twitching tightly. She began to rub lightly in circles. "Just relax and breathe, Jason. Focus on how nice it feels."
Cat knew that it would take him a bit to relax and give in to her. She patiently worked him, stroking his leg, buttocks and lower back, whispering soothingly. Gradually he relaxed and opened to her ministrations.
"That's good, Jason, very good. I'm going to start to insert my finger. Stay relaxed. Remember, I promise this will feel really good." Cat pushed just a tiny bit, then pulled back. A little bit further, then back again. Continuing to repeat the process, she slowly penetrated deeper and deeper, continuing to rub his body and speaking in a soothing voice. When she was able to insert her finger fully, she moved it in and out a few times making sure that it slid smoothly. "Jason, I'm going to take my finger out. It'll feel strange and a little empty now that you're used to this, but it's just for a minute. I'm going to put some lubricant on your boy-penis, then I'll put my finger back in and rub them both at the same time." Cat slowly removed her finger and Jason was surprised that he did indeed feel somehow empty.
Cat removed the finger cot and poured lubricant into her palm. She rubbed her hands back and forth rapidly. It was hard to get any friction going with something this slick, but she hoped that she had warmed it at least slightly. She slid the finger cot back on and reached under him with her other hand. He hung flaccid, but that was easily remedied. Feeling playful, she brought her palm up so that the very tip barely touched it. She closed her fingers until they touched his flesh just behind the crown. A little smile crossed her face and she closed her fingers rapidly. What might have hurt in a different situation, made Jason gasp. The super slick lubricant caused her fingers to rapidly slide over the crown and down to the very tip like a starfish bringing its arms together. A couple of more times and Jason quickly plumped up fully. She wrapped her hand around him and slowly stroked, limiting her movements to the shaft and only enough to maintain his erection.
He entered the bar and looked around. He wasn't quite sure how to go about it, but the articles had stressed being honest and forthright. Well, nothing to do but dive in, he said to himself. There was a single woman seated at the bar. Jason walked up to her and cleared his throat. She glanced at him sideways but said nothing.
"Hi. Um..." He cleared his throat again. She looked at him with mild annoyance. "Um...are you...um...transgender? A transgender woman?"
She looked at him, glancing up and down, taking him in. He was clearly extremely nervous, his hands shaking slightly and a bead of sweat at his hairline.
"Oh, you're one of those. We get you guys in here from time to time. I'm gay, but if that's what you're looking for..." She looked around. "See that woman over there with the silver hair? That's Cat. Word has it she likes breaking in you newbies. Go talk to her."
Jason looked around. She was at the far end of the bar engaged in animated conversation with another woman. "Silver hair? Is she old?"
"No, it's a dye job. It's an in thing right now, but she's done it since before then. Now leave me alone so I can get drunk and forget about my girlfriend cheating on me."
"Oh, sorry."
The woman just waved him away and returned to her drink.
Jason walked over and sat on the empty stool next to the woman called 'Cat'. He ordered a drink, nursed it and waited for the women to stop talking. Eventually, the other woman got up and left.
"Are you going to keep staring at me out of the corner of your eye, or do you want something?"
"Er, um...I...that is..." Jason stammered, flustered.
"Come on. Spit it out."
"One of the other ladies said that you might be a transgender woman?"
"Yes, I am...and?"
"I, uh...was, uh...wondering if you might have sex with me?"
Cat looked at him hard, her eyes narrowing. She absorbed him, sizing him up, looking at everything about him, even his demeanor and posture. She guessed him to be early twenties, meaning he was probably inexperienced either way. Unless they'd been taken in under the wing of someone much older, they simply hadn't had enough time to get good at sex. Many didn't even have a clear idea of who they themselves were.
"Let me guess. You're gay but still in the closet. You want to dip your toe in the water, but imagining a guy's face while you're doing it freaks you out?"
Jason looked slightly confused. "No, I don't think I'm gay. I just thought...that is...I...I was curious..."
"Oh, I get it. You're a fetishist, but you're also a newb."
"Uh, I, um, I'm sorry if I offended you."
"No, no offense. Hmm..." Cat looked him over again. On one hand, she really liked breaking new people in. It was her favorite thing to do. On the other, it took time to do properly and it was already late. She preferred to start early in the day. Cat thought of herself as one of those rare teachers who took a special interest in a promising student and provided them with the knowledge, resources, and encouragement to help them reach their full potential. Quite a few others thought of her as some kind of weird freak by any standard. There were wild rumors surrounding her and stories that couldn't possibly be true. However, even her greatest detractors had to admit that no one who'd been with her ever had a single unkind word to say. In fact, they never said anything except that it had been "wonderful", "incredible", or "amazing". One had even used the word "heavenly". Cat never acknowledged the dark looks she sometimes received, though it always made her smile.
"You clean? Any diseases or stuff?"
"No, no diseases or anything."
"First time, right?"
"Yes."
Cat stared at him silently for a couple of minutes. He appeared to be about the same height as her and slightly pudgy. His skin was slightly darker than caramel, but green eyes belied a mixed race heritage. Objectively, he was mildly good looking at best, but it was the eyes that drew you in. He had very, very pretty eyes. She turned it over in her head as she studied his face. He made her think of a lost puppy. Against her better judgment, she nodded.
"Alright. Let's go. You can follow me back to my place."
Jason followed Cat to her apartment. As soon as the apartment door was shut, Cat grabbed him by the collar, slammed him into the door, then pulled him in for a kiss. She shoved her tongue into his mouth, swirling it all around, even licking his teeth. "I'm not some dainty girlie girl. I know what I like and I'm not shy about it. I also like to be in charge." She studied his face for a moment. "You sure you want this? You can leave right now. No harm, no foul."
"Uh, yes, I think I would like to stay," Jason stammered.
"Alright, some ground rules then. First, pay attention to what I say. Use the words I use. If I tell you to do something, you do it. No hesitation. If I tell you not to do it, you don't do it. Capice?"
"Uh, uh, yes, ma'am."
"Just call me Cat. If you're into pain play, bondage, diapers, or whatever, we're not doing that tonight. This just going to be basic 101 stuff. Okay?"
Jason nodded.
"I know you said you're clean, but unless you have some recent test results in your back pocket, we're both using condoms."
"Both of us?"
"Yeah, both of us. This isn't just about you. I'm going to have my fun as well."
"Uh, okay."
"Alright. Bedroom's this way." Cat turned on her heel and headed down a short hallway and disappeared through a door. Jason hurried to follow after.
The two stood face to face and Cat kissed Jason aggressively again, then stepped back.
"You're probably wondering what I look like."
Cat rapidly undressed and took another step back, letting Jason look at her. She slowly turned around giving him a 360-degree view. Cat's face was pretty, but not much more so than any other woman. There was a certain perfect symmetry to it that made your eyes linger. Her eyebrows were dyed to match her silver hair and her make-up was light. Her body was the color of Carrara marble. Her arms were slightly muscular, as were her legs. Her breasts were small, perhaps an A cup, and nicely shaped. Her stomach was smooth and slightly muscled as well from daily workouts. Her pale blonde pubic hair was neatly trimmed and an average sized penis hung down with heavy looking testicles behind it. Giving him a moment to look her over, she tilted her head, shifted her stance, put a hand on her hip, and turned slightly to present an oblique angle.
"I'm going to give you one more chance to back out."
Jason shook his head.
"Alright then. Remember that I did try to be merciful."
She smiled like a dangerous predator. A tiger stalking prey. He looked a little scared, but set his jaw and stood his ground. Potential, she thought.
"Now, your turn. Get undressed so I can see what I'm working with."
Jason didn't undress. Instead, he stared at Cat's body, looking up and down repeatedly. He took a hesitant step forward. "Can I touch it?"
"Heh," she laughed. "Go ahead."
Jason took another step forward and reached out to take her penis in his hand. He felt the silky texture and rubbed his thumb back and forth across the tip. He slid his hand up and down, fascinated. It seemed all the more beautiful for being attached to a woman. It began to stiffen in his hand. Without thinking, he stroked it gently. It firmed up fully and throbbed slightly within his grip. He felt a bit of relief that it was no bigger than his own. He'd seen some videos and was concerned that it might be very large. He tore his eyes from it and looked up to Cat's face and back down again. He reached out and touched a breast, pulling his hand back, then touching it again. Cat had seen this before and waited patiently.
After a minute, Jason spoke. "Uh...um...can I...uh...?" The tip of his tongue appeared between his lips.
She laughed. "Want some girl-cock, huh? Your mouth is watering and you're imagining what it tastes like? Alright, come over here."
Cat walked over to the bed, as graceful as a leopard, grabbed a pillow and dropped it on the floor. She sat on the edge of the bed, her legs spread wide. Leaning back slightly on one arm, she waved him over. "Kneel on the pillow." Jason was on his knees in a flash.
"You ever sucked one before? Girl-cock or boy-penis?"
"No, ma'am...er...Cat."
"Mouthed a dildo?"
Jason shook his head.
"Cucumber? Anything?"
Jason shook his head again.
"Complete virgin. Okay, here's what's going to happen. I'm going to talk you through it. Do what I tell you and you'll enjoy yourself. Certainly, more than I will. You got balls, so remember that they're sensitive when you're working them. Now, kiss it."
Jason puckered his lips and kissed the top of her glans.
"No. On the shaft, about halfway down."
Jason kissed Cat's girl-cock again, then opened his mouth.
" Ah ah." Cat smacked him lightly on the top of the head. "Remember, do what I tell you. Now, put your lips to it again, like you're going to kiss it, but leave them. Just let it rest there." Jason brushed his lips to her and remained in place.
Cat squeezed, flexing and relaxing the muscles in her pelvic floor. Her girl-cock raised sharply then dropped to bounce against his lips. Jason didn't move. She did it again, arching her eyebrows. Jason remained still.
"Good boy. First of all, don't just inhale it and gobble it down. You want to start slowly and build up. You want it to be enjoyable for both of you. Yes, it can be fun to jump in zero to sixty or be a little rough. But like I said, we're just going to stick to the basics. Now, gently take hold of it..."
Cat started Jason out with the basics giving good head. He proved eager to learn and followed her instructions exactly. He also turned out to have a pretty agile tongue. Hmm...not bad, Cat thought. She started guiding him to her specific preferences. Jason was an apt pupil.
"You're doing good, Jason. Now, I want you to improvise."
Jason continued to follow the last instruction she had given him.
"Improvise, Jason. I want you to experiment and have fun doing whatever comes to mind."
Jason sat back and looked at Cat's girl-cock with a bit of consternation. Cat flexed a couple of times, causing it to bob up and down. "Come on, Jason. Don't leave a girl hanging."
Jason took her back into his mouth and began trying different things. He quickly got into it, showing creativity, even adding flourishes. Pretty damn good, she thought. Cat relaxed back on her elbows and closed her eyes.
"Jason, I'm going to put my hand on the back of your head and fuck your mouth. Keep your lips closed firmly, but not too tight. Keep using your tongue like that."
Her eyes still closed, Cat wove her fingers in Jason's hair and pushed his head down firmly. She repeatedly humped up, sliding in and out quickly. She gave him a couple of minutes of mouth fucking. He's lying, Cat thought. She knew that there was no way a beginner had this kind of talent.
Cat opened her eyes and pushed Jason's forehead back, forcing him to release her. She bobbed freely, tapping his lips, nose, and cheeks. "You're doing great for your first time, Jason. Now, do you want me to come in your mouth?"
Jason watched her girl-cock sway, almost hypnotized.
"It's okay to say no. I can come on your face or just wherever."
"I think I would like it in my mouth."
"Good choice. As I'm sure you know, orgasms are pretty much the best things ever and your body isn't fully under your control when it happens. I'm going to want to push forward deeper into your mouth. When that happens, I'm going to poke the back of your throat, perhaps kind of hard. I might even go down into your throat a little. Since you're inexperienced, you're probably going to gag. I don't want you spitting up on me or vomiting on my lap. So, what you need to do is hold the shaft firmly and pull your head backwards as I move forward. Try to keep me in the middle of your mouth. Do you understand?"
"I think so."
"Good. Let's give you your first taste and then we'll have some fun getting you off." She flexed again and Jason took her back into his mouth. "You've got decent tongue action." She was downplaying just how good it was. "Focus on the crown and pump my shaft fast. Give it just a little twist one way at the base and the opposite way at the top. Yes, just like that. Yeah, mommy like. Mmm...nice. That...do that faster. Keep going, I'm almost there. Yes. Really good, Jason. Mmm...get ready. Shit, yeah, fuck..."
Cat's orgasm was much better than she had expected. Her hips came off the bed and she had to fight not to grab Jason's head and shove it down on her pole. Just as she had said it would, her girl-cock jammed into the back of his throat. Her hips jerked forward pushing deeper. Jason gagged, but wanting to do a good job, tried his best to suppress it. He gripped her shaft firmly and pulled back trying to keep her in his mouth as she jerked and twitched.
Cat had forgotten to warn Jason about just how much she was going to come. Cat's ejaculations were prodigious, her loads considerably larger than anyone else she had ever been with. Jason's cheeks ballooned slightly and a trickle formed at the corner of his mouth. Cat noticed through fluttering eyelids and struggled to speak. "Swallow, Jason. Just keep swallowing. It'll stop in a little bit." Jason nodded a tiny bit and swallowed continuously. Several more contractions rippled along her length, continuing to fill his mouth.
Cat's orgasm subsided and she ruffled her hand through Jason's hair. "Run your tongue around your mouth and get a good taste." She smiled broadly. "Great job, Jason. Really good." If he's really a newbie, then he's a savant, Cat thought. Jason still held her in his mouth, his eyes gazing up at her, enjoying the praise. "Put the tip of your tongue in my slit and wiggle it like you're trying to get inside. Move your hand to the base and make like an 'ok' sign. Now, squeeze a little and pull upward, so that you're milking anything left into your mouth." Jason milked the last bits out of Cat and she patted his head. Jason sat back and looked up at Cat. She stroked the side of his face gently. "Wonderful job. Really." Jason positively glowed. "Okay, let's take care of you. Get undressed and on your hands and knees on the bed."
"I...uh...never sucked a penis..."
"Girl-cock," she corrected him.
Like many people with a non-traditional view of sexuality, Cat had her preferred terms. A phallus was a girl-cock or boy-penis, depending on how its owner presented themselves. Similarly, most people presenting themselves as more male or with a masculine dominant aspect were 'boys', though they might sometimes be referred to as 'guys' or 'dudes' in third person conversation depending on their perceived maturity level. Female or feminine dominant presenters could be 'girls' or 'women', also depending on experience and perceived maturity. These latter terms applied independently of their subject's sexual organs. Some tried to present themselves neutral or a homogenization, but there was always something that steered her one way or another. If that person expressed a desire for their own terms, she would respect that and accommodate them.
"What?"
"I have a girl-cock. You have a boy-penis. Say it."
"You, uh, have a girl-cock. I have a boy-penis."
"That's right. Now, what were you going to say?"
"I never did that before."
"Well, you did a fantastic job. Did you enjoy it?"
"Yes, it was fun. And then when you...uh... I liked it. It was really thick, but it tasted good. There was so much. I can still taste it."
"Good. I promise you'll enjoy everything we do tonight."
Jason undressed slowly. There was trepidation in his voice. "Are you going to fuck me in the ass?"
Cat smiled and gave him a peck on the cheek. "Yes, Jason, I am, and when I do, you'll enjoy that too. But just because you'll like it, it doesn't make you gay, if that's what you're worried about. That has nothing to do with being gay. Try to relax and don't worry about it right now. We're going to do something else instead and I promise you'll love it. Now, get on the bed."
"I...uh...read something about safe words..."
"Those are only necessary if you're not fully committed. Are you fully committed, Jason?"
"Uh..."
Cat's voice hardened. "Leave. I don't deal with c***dren."
"No! I'm committed! Fully!"
Cat's voice softened and warmed. "Excellent, Jason. I believe that I told you to get on the bed."
Jason scrambled to get on the bed.
Cat opened the top drawer of the dresser. She grabbed a finger cot and reached for her preferred lubricant. "Are you allergic to silicone? I have water-based too."
"I don't have any allergies that I know of."
Cat moved over to the bed and put on the finger cot. "Jason, I'm going to rub your anus. I'm just going to use my finger. I'll be using a great lubricant, so it'll be nice and smooth. I want you to relax as much as you can. Just take deep breaths and focus on the sensation and how good it feels." Cat used plenty of lube, coating her finger and Jason's anus. She could see his sphincter twitching tightly. She began to rub lightly in circles. "Just relax and breathe, Jason. Focus on how nice it feels."
Cat knew that it would take him a bit to relax and give in to her. She patiently worked him, stroking his leg, buttocks and lower back, whispering soothingly. Gradually he relaxed and opened to her ministrations.
"That's good, Jason, very good. I'm going to start to insert my finger. Stay relaxed. Remember, I promise this will feel really good." Cat pushed just a tiny bit, then pulled back. A little bit further, then back again. Continuing to repeat the process, she slowly penetrated deeper and deeper, continuing to rub his body and speaking in a soothing voice. When she was able to insert her finger fully, she moved it in and out a few times making sure that it slid smoothly. "Jason, I'm going to take my finger out. It'll feel strange and a little empty now that you're used to this, but it's just for a minute. I'm going to put some lubricant on your boy-penis, then I'll put my finger back in and rub them both at the same time." Cat slowly removed her finger and Jason was surprised that he did indeed feel somehow empty.
Cat removed the finger cot and poured lubricant into her palm. She rubbed her hands back and forth rapidly. It was hard to get any friction going with something this slick, but she hoped that she had warmed it at least slightly. She slid the finger cot back on and reached under him with her other hand. He hung flaccid, but that was easily remedied. Feeling playful, she brought her palm up so that the very tip barely touched it. She closed her fingers until they touched his flesh just behind the crown. A little smile crossed her face and she closed her fingers rapidly. What might have hurt in a different situation, made Jason gasp. The super slick lubricant caused her fingers to rapidly slide over the crown and down to the very tip like a starfish bringing its arms together. A couple of more times and Jason quickly plumped up fully. She wrapped her hand around him and slowly stroked, limiting her movements to the shaft and only enough to maintain his erection.
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