Jaymes Emasculation

This is my first story so I would love to hear any feedback. I plan on adding to this story and starting a few other storylines as I have time to do so.

Enjoy!

Chapter 1

Jayme was having a good day, well the best day in a long time to be more precise. He was walking over to see his long time friend and crush Cassie. She had invited him over for a date night. He was honestly surprised when she extended the invitation. Even though he has had a crush on her for years, since grade school, she has never given him any signs that the feelings were mutual. Leaving him in the 'friend-zone' for as long as he can remember. She did not live that far away so it was a short, maybe 10 minute, walk from his house to hers.

He was almost there and nervous as could be. Usually Cassie dates more masculine men compared to him, her last boyfriend was over 6ft tall, muscular and confident. Jayme on the other hand was 5ft 5 and had a slim build. He went running often to stay in shape but never lifted weights so he wound up with a well developed bottom half and a slim, almost feminine upper body. But he was trying not to think too much into it, she had texted him out of the blue yesterday and asked if he wanted to come over for a 'date night' with a 😉 in a following text. He eagerly took her up on it and she said she would give him something he has been wanting for along time but is too shy to go for.

His heart started to beat a little faster as he got to her front door and it took all of his courage to knock and not run away, writing the whole thing off as a fever dream. When she answered the door his fears just melted away. There she was in all her beauty. Standing a couple inches taller than him, with lovely curves that fit her petite frame perfectly. He knew she took a yoga class regularly and it showed. She was wearing white tennis socks, capri cut jeans that were skin tight and a cute white top that hugged her body just enough to show off, but not tight enough that it still left something to the imagination. Her cute face was framed by her long ginger hair that flowed a few inches past her shoulders. She has the cutest freckles he thought to himself. He looked into her beautiful blue eyes and realized he was just standing there. She had caught him staring and giggled, making him twitch a little in his pants.

"Come on in" She said, stepping to the side.

"Uhh, thanks" He stammers out awkwardly, walking in.

She led him upstairs while making small talk, catching up on some gossip about old friends from school, who wound up dating who and all that. It had been a while since they had hung out. In her room he sat on the edge of her bed and she walked over to her desk on the other side of the room and leaned against it.

"No need to be soo nervous Jayme. I know its something you have wanted for a long time" She smiled and winked while saying that. He could not help but let out a nervous laugh when she said that.

"Yea you are right, everyone has their first time right?"

"Of course they do. Although its something you really only need to do once if you do it right." She says. "Get naked and sit on the end of my bed." She suddenly orders.

Nervous and not really sure what she means by that, he just does what she tells him to do in the hope that he does not mess things up and make her change her mind. At this point Jayme is already harder than he ever has been in his life, his little penis standing at its full 4 inches. He takes off his shirt first revealing a hairless chest. He never really did grow much body hair always figuring it would come in some day. Taking off his pants, socks and boxers he kept one hand in front of his small penis while he sat down, trying to keep his little secret for a few seconds longer. She was rummaging around her drawers, looking for something in particular before turning around. She was still fully clothed.

"You don't have to hide from me, I do have to see what I'm working with." She said with a wink.

He moved his hand away and leaned back, displaying himself for her to see.

"Aww its soo cute!" She said with excitement! "I can't wait to see it after we are done!"

He is really starting to wonder what she means by that, but as a virgin maybe there are a few things he does not know about what people do after sex. His little penis was throbbing at this point and he could barely think straight, so he focused on her. Looking at her sexy body and beautiful face, he could barely believe where he was and what he was about to do. He noticed in her hand she was holding a condom package with a large "G" on it. It looked a little big for someone of his size, but he was not going to say anything and he was trying everything he could to just avoid blowing his load right then and there.

She approaches him and stands in front of him, still fully clothed. He is confused but just goes with it. His penis is starting to tingle as it continues to throb. She kneels in front of him and puts a hand on his thigh to steady herself as the gets on her knees, sending a wave of pleasure up his leg. He struggles to hold back but its no good. She lifts the condom up to her mouth to use her teeth to tear open the package and seeing that was what put him over the edge.

"Hhnnggg" he leans back as he loses control of his tiny penis, shooting his load, well more like dribbling his load. Running down his small shaft and over his balls. She starts to giggle watching him lose control and cum prematurely.

"Oh my!" She remarks, covering her mouth to hide her laughter. "I don't think anyone has ever done that before!" She stands up and walks back to her dresser, tossing the condom inside and turning around. She grabs a hand towel from her desk and tosses it over to Jayme so he can wipe up his small load. "Don't get any on my bed sheets please."

"I-I'm sorry, I don't know what happened." He stammers out grabbing the cloth and wiping his softening penis and trying to cover himself up with his one hand while grabbing his boxers and pants with the other. He could not believe it! He finally gets the chance of a lifetime and he blew it. Literally. The strange part is that she does not seem disappointed, looking at her he wonders why that is. She seems amused but not upset.

"Don't worry, I know how exciting this must be for you." She says, giving him a knowing smile. "We can always try again tomorrow? Maybe have a little.... Fun at home before you come here and you might be able to hold off until we get the condom on you next time."

"That would awesome. I know I can do better next time." He could not believe it, she was going to give him a second chance after what had just happened.

He got dressed quickly and she just watched him, almost like a predator watching its next meal, not saying anything. Once he was dressed he got up to leave and she gave him a big hug and led him to the door. Saying good night and heading out to walk home he could feel his cheeks burning as the embarrassment was overwhelming his mind. He barely remembered the walk home, his mind replaying the nights events over and over. He found himself getting aroused again as he walked in the door to his home. His tiny penis barely making a tent in the front of his jeans.

His mother was sitting on the couch watching TV when he walked in. She looked surprised to see him coming in the door.

"Back soo soon?" His mom Tara asked, "I thought you had a date tonight with Cassie."

"Yea we just rescheduled for tomorrow, something came up." He said, lying to cover for his premature ending of their night.

"Oh ok, that's alright. I'm gonna head to the gym right away hun, dinner is in the fridge if you want to heat it back up." She stands up from the couch and grabs her phone, sending a quick text. She towers over him as he walks by heading for the stairs, at almost 6ft tall and fairly well built, Tara is a bit of a gym rat.

"Thanks mom, I'm not hungry right now, I'm actually pretty tired. I'm just gonna go read for a bit before bed." Jayme responds as he heads up the stars. Tara's phone buzzes as she gets a response to her text, she reads it and starts to giggle, trying to hold back her laughter. Jayme begins to wonder who she was texting, he knows that her and Cassie work in the same office and they are good friends. But he is sure that's not who she is texting, right? Cassie would not share those details with his mom.... Would she?

He closes his bedroom door and sits in front of his computer, booting up his favourite porn website while taking his pants and boxers off. Still needing to work out some pent-up energy from the evening. He browses the videos, scrolling until he finds one with a beautiful woman being fucked by some big muscular dude. She is bent over and being fucked in the ass, he starts to stroke himself to the scene, really getting into it. Then the girl on screen is turned over and he is shocked to see that she has a penis! A small one but its there, soft and flopping around as she(?) Is fucked by her partner's huge cock. At first Jayme tells himself he is not interested in that kind of thing but quickly realizes his is still stroking his little penis and almost as soon as he realizes that, he starts to cum from a mixture of surprise and excitement. "I can't be into this sort of thing." He says to himself, thinking he is into normal girls like Cassie.

Chapter 2

Jayme was in a little haze all day at work, going from not being able to believe that he prematurely shot his load yesterday to the fact that she wanted him to come over and try again tonight! He was the luckiest man alive in his mind right now. After work he went home and ran up to his room, barely stopping to say hi to his mom who was busy getting ready for a jog. He went straight to his computer, closing his bedroom door. His phone buzzed a couple times, once his mom was saying that she would be out for a bit jogging with friends and the other was Cassie saying he could come over whenever he was ready with a 😉 at the end of the message. Remembering what she said the night before he went straight to his favourite website and started scrolling through the video section. He quickly found a video with the same model from last night, he clicks on it right away.

Wondering what drew him to that model and her video, he starts watching it. "I'm not into traps, am I?" he wonders out loud as the video starts playing. This time it's a clip that has her on her knees in front of some stud with a massive cock. It must be at least 3 times the size of mine, he thinks to himself as he starts to stroke his tiny penis. Getting himself rock hard he looks down and sees that he can hide his entire penis in his hand, and for some reason that makes him even harder. He feels a large amount of confusion as he watches the video, the beautiful girl in the video with her long black hair, obviously implanted breasts and tiny cock, sucking on a massive cock and enjoying every moment of it. She is playing with her own as she sucks on his. Jayme is drawn to watching her pump her tiny cock for pleasure while she pleasures the man in the video. It takes Jayme barely 3 minutes to pump out his small load into a wad of tissues. He gets cleaned up and tossed the tissues out, his mind swirling in confusing thoughts of arousal.

I'm going to go have sex with a woman I have wanted for years and I'm watching porn where everyone has a cock. What's wrong with me? He does not give it too much thought as he heads downstairs, texting Cassie to let her know he is on the way over. She responds right away with a smiley face.

He got to her house in record time, knocking with more confidence. Telling his little penis to relax as it is trying to get hard again, already. She greets him at the door, wearing black leggings and another lose fitting green shirt. She reaches out and grabs his hand, pulling him upstairs.

"Don't want to wait too long this time!" She remarks excitedly as she pulls him into her room. "If we let you get too worked up you might not make it again." She winks at him pointing to the foot of her bed.

"Get naked and sit! I went out today and grabbed another condom, after seeing you yesterday I was worried the others I have would not fit snugly, so it got one a few sizes smaller!" Her words should have stung but Jayme was not thinking clearly at all. He reassured himself that she chose to have him there so obviously his small size was something she wanted... Right?

He sat on the foot of her bed naked just like yesterday, not covering his little penis with his hand this time. She grabs the condom off the dresser, this time it looks like a smaller package and it still had the "G" on the front. Maybe it's a brand name? He barely wondered to himself. She looks him up and down and lets out a little giggle.

"It really is cute, totally suits you." Gesturing to his crotch, his tiny penis standing straight up, as hard as can be. "I think this is gonna be awesome and I can wait to see how it turns out." He thinks she must be talking about how she thinks he will preform in bed or something like that. She better hurry, he can feel his penis start to throb and tingle. Not as bad as yesterday but its getting there.

"Lean back." She tells him and he does, reaching behind himself and resting on his hands with his arms straight. She kneels between his legs, not touching his thigh this time and opening the condom package quickly. He notices its not like any other condom he has seen before. It reminded him of a balloon that was half rolled up. He thought condoms are always rolled up and you roll them down the shaft? But this one seemed half unrolled and the tip was huge. "You are gonna love this!" She said as she put it on the tip of his penis and rolled the other half down his thin shaft. She condom was tight at the base and loose towards the tip, with about 4 inches extra hanging off the tip of his penis. She leans back on her heels and looks at his crotch excitedly.

"Isn't it supposed to be a snug fi-" He starts to ask but is overwhelmed by a jolt of pleasure running down his shaft into his groin. He closes his eyes and leans back onto his elbows as the pleasure ramps up, spreading into his balls and sending pulses down his legs and up his back. He can't believe what he is feeling, for a moment he is upset that he is about to prematurely shoot his load before he gets to have sex with Cassie but that thought is quickly pushed aside by the overwhelming feeling of pleasure. His entire penis feels like it is tingling and throbbing, almost tightening at the same time, his balls feel like they are pulling up into his body. Its indescribable. Somewhat like when your foot falls asleep and is waking back up but at the same time it's the most amazing feeling of his life. Before Jayme can get a grasp on how good it feels he starts to cum harder than he ever has before. His body wracked by pulse after pulse of pure pleasure, it feels like his penis has become a firehose. He has never felt anything like it. His balls and scrotum feel like they are tightening up and pulling towards his body, his penis even feels like its shrinking with every pulse and he has not a care in the world other than the amazing orgasm his is currently riding though.

After what felt like an eternity he finally comes back to reality, it could not have been more than a minute but for him it was the longest and best minute of his life. He starts to feel a little confusion as Cassie reaches in-between his legs and grabs the condom, taking it off. It felt like it was barely covering the tip of his penis.. That cant be right. He sits up and looks down and is shocked to see there is barely anything between his legs. Maybe it takes a moment to come back after cumming like that he thought.

A few moments later he realizes that his balls and sack are missing, his penis still looks hard, but its barely an inch long and about half as thick as it was before. This cant be right, it looks like all I have left is the tip and maybe a quarter of an inch of shaft left. But there it was, standing proudly like a large clit above a smooth patch of skin where his balls should be hanging.

He looks over at Cassie and she is just tying a knot at the base of the condom, sealing it off with its contents inside. She catches his gaze and giggles again. "Its soooo cute! I love it." She says as she points to his little nub. "It fits you soo much better now." She then holds up the sealed condom and he gets a good look at it. Inside the condom there are two small balls and a lot of cum. He blinks for a moment and looks down and back up. There can be no other explanation, those are his balls and that's the last load he will ever shoot out of his penis.

She hops up to her feet gleefully. "I'm soo glad you chose me to share this moment with, most femboys usually just do this at home!" She walks over to one of her closets. Jayme is speechless, he had no idea that this was going to happen or what gave her the impression that he wanted this. "Honestly yours will be a favourite in my collection!" She says as she opens her closet revealing several clotheslines with about a dozen other condoms hanging from them. She looks over her shoulder and smiles while she hangs my contribution up. I realize with a pang of embarrassment that my condom is by far the smallest and that my balls are about half the size of the one hanging next to it. She closes the closet and turns around looking gleeful.

"I- wait- what- I didn't know that you were going to do that." Jayme stammered.

"Oh don't be silly, we both know you have always been effeminate and plus yesterday you saw the gelding condom and wanted to come back to use one with me today." She responded. "You can't believe that I would want to ride your little premature clit, did you?"

Her words stung his pride. "I don't- gelding condom? I don't know what to say right now."

"Yea, they are all the rage with femboys right now and some girls like me use them to get back at mean ex's, or just because we love doing it!" She laughs at the last part. "Usually when someone has a man sized cock it just shrinks down to half its size, usually as big as yours was to begin with, but with femboys like you they really shrink down to nothing. I have never seen anything like that before but I'm really happy you came over to share this experience with me."

Jayme's head was swimming right now and for some reason he kept thinking of the woman from the vid he was watching earlier. He was snapped out of his thoughts by Cassie tossing him a pink thong. "Put it on, it will fit you better now that you don't have anything in-between your legs anymore." He was about to protest but then he looks down at the remains of his penis, no it's a clit now, and realized she was right. He should be protesting more but something compelled to do everything she said, so he stands up and slides the pink frilly thong up his legs and pull it into place. His clit was rock hard and feeling it rub against the soft fabric sent shivers up his spine. There was a cute little white bow on the waistband, and it really did seem to fit him well, he hiked up the waistband over his hips and noticed that his legs looked really feminine. Must be all the running, he thought to himself.

"Love your new look?" She asked. He was about to answer when he realized she had put on a harness over her leggings with a massive strapon sticking out of the crotch!

"Umm what's that for?"

"I wanted to be your first, remember?" she smirked. "I thought you wanted me to take your virginity."

He could not believe the sight before him. There she was, the most beautiful woman in his world, the woman he had grown up with and had a crush on for as long as he could remember. The woman that just took his balls and most of his penis, standing there looking perfect with a massive strapon cock dangling from her crotch. He would have done anything she asked at that point.