Jayme's Emasculation Pt. 02

Here is part 2 of Jayme's ongoing story! I hope everyone is enjoying themselves and be sure to leave a comment if you have any feedback.

Chapter 3

Jayme sat next to his mom drinking his wine in silence for a few moments before she broke the silence again "so, tell me about your night hun! I hear it was quite the evening for you and Cassie!" She giggles. "Come on, you can tell me all about it."

Jayme is at a loss for words, he is blushing furiously thinking about the nights events and for some reason is more turned on than he has ever been in the past. Thinking that his mom not only knows about what happened but might have even played a part in it. "Yea, our date went well I think." He says.

"Just well?" She asks with a mischievous smile. "I hear it was a lot of fun for both of you."

"So Cass told you about it?" He asks, secretly hopeful that Cassie left out some details.

She breaks out in a fit of laughter "Yea she told me all about it! Honestly hun, I'm really glad you decided to go through with it. I have always thought you would go that route in life with you always being more effeminate, but I honestly was not fully sure until you decided to go back to her house tonight."

Tara leans back on the couch and downs the rest of her glass of wine and Jayme does the same. Jayme is full of conflicting emotions, on one hand it was the hottest experience of his life and his newly shrunken clit is more sensitive than he thought possible, every time he moved around it rubbed against the soft material of his thong sending shivers up his spine. On the other hand he was not happy about having to give up his balls for it and having his penis shrunk down to a fraction of its previous size. 'I guess its not like it was too big to start with' he thought to himself.

"Here" Tara hands him a refilled wine glass, he was so lost in thought he didn't even notice her grab a fresh bottle. "What are you thinking hun?" She asked, looking into his eyes for answers.

"I don't know, I really did not expect tonight to go the way it did." He admitted. "I thought she just wanted me to come over so we could hook up." He said sheepishly.

"Well I thought you two did hook up, didn't she take your virginity?" She responded with a wry smile. "After all you did go back after your first night with her ended a little... fast."

"Yea I know that, I just thought I would be the one fucking her, not the other way around" Jayme said, looking down at his wine glass.

"Oh sweetie, I know that's what you were expecting but you have to admit that would just not have worked out for either of you. Honestly me and Cass really thought you knew what those condoms were for." She said looking a little sympathetic. "I really think its better this way anyway." She added.

"Yea it was a lot of fun for sure." Jayme responded, "I was just surprised I guess."

"Well if what Cass said is true, you really enjoyed the way things went anyway." She said with a wink.

"Yea it was amazing." Jayme admitted

They both sat in silence for a few minutes enjoying their wine. Jayme was coming to terms with his new situation, thinking to himself 'maybe Cass and my mom are right, I would never had been able to please a woman with my tiny penis and now its more like an oversensitive clit. Not to mention how amazing it felt when Cass fucked me with that strapon..'

"I wanna see it!" Tara blurted out interrupting his thoughts. "I have never seen one in person and I have always wanted to see what it looks like after a femboy uses a gelding condom." She said with enthusiasm.

"I-I don't know." Jayme said, not wanting to show his new clit to his mother. "Its kinda embarrassing and I dunno, it feels weird to undress in front of you."

"Oh come on, its not like I have not seen you naked before! Besides I always wanted to see one up close and Cass said yours shrank a lot and is really cute! Pleeaasssee" She begged. "Ill let you borrow one of my toys for the night if you show me."

He was not sure why he was even considering her request but it was tempting. He had been giving some real thought to buying a dildo to experiment with since it had felt soo good when Cass fucked him and for some reason he just felt compelled to do what he was told since she had used that condom on him. 'She really did take my balls' he thought to himself 'not just physically'.

"What kind of toy?" He asked, wanting to at least get something out of this.

"Ill show you!" She said excitedly, jumping up and dashing to her room upstairs. Jayme could hear her opening a drawer and rummaging around for a moment before coming back downstairs. Her offer in her hand. It was huge, around the same size as the dildo Cass has fucked him with. It had to be almost a foot long and as thick as his wrist, with a large bulbous head and veins running down the side of the shaft to the base where a huge set of black balls were hanging above the suction cup base.

She sat beside him again and stood the dildo up on the table using the suction cup to stick it to the tabletop. It just sat there, standing straight up like an obscene monument to the masculinity he never had. He just stared at it, 'why is my mouth watering' he wondered to himself.

"So?" She asked, snapping him out of his daze "Ill let you borrow that for the night and a bottle of lube to keep if you show me what you got left in your jeans." She giggled at the last part.

Jayme could not believe what he was about to do and as if in some kind of trance, he stood up and started to unbutton his jeans before realizing he was still wearing the yellow thong that Cassie had given him earlier as a trade for his masculinity. He stood there frozen for a couple seconds, unsure of what to do.

"I know she gave you something nice to wear under your jeans, I even suggested yellow." His mother said.

Giving into the situation completely he unzipped his jeans with a small sigh. 'They really did plan this out together' Jayme thought to himself. Dropping his jeans and revealing his cute yellow thong and the tiny bulge it contained. Tara leaned back and tried to suppress a laugh by putting her hand over her mouth.

"Oh my god its so cute!! I love it!" She exclaimed. "That's even better than I had pictured. You know, originally when Cass saw your tiny penis last night she knew she had to get a smaller gelding condom for your date tonight, but was going to get one that didn't shrink you penis, I convinced her to stick with one that shrinks your penis after using it."

Jayme was having a hard time processing what he was hearing form his mother. "I figured since you could never please a woman with that tiny thing it would be best if it was as small as possible, since they get a lot more sensitive when they shrink. This way you can have a lot of fun playing with it like a girls clit." Tara added. "Now lets see it!"

Jayme grasped the waistband of his thong and slipped it down over his thighs revealing his shrunken nub and Tara gasped with delight. "So is it super sensitive? How big does it get when its hard now?" She asked.

"Yea its super sensitive now, its always rubbing on my jeans." Jayme admitted, blushing furiously. He looked down at his crotch, seeing his little nub sticking out. He felt as hard as he ever had in his life and it only stuck out an inch if he was being generous to himself. 'why am I so turned on right now?' he wondered to himself. 'Am I excited by being humiliated by my mom and Cass?'

"That's as hard as it gets? Isn't it?" His mom asked, prying for an answer. Jayme nodded a yes. "I love it! It fits you perfectly!" Tara proclaimed.

Jayme quickly pulled his thong and jeans back up and grabbed his wine glass, finishing it quickly wanting to run away from this confusing situation as fast as possible. As he turned away from the living room his mom reminded him to take his reward upstairs with him. When he turned back to the table she told him to make sure he used lots of lube and to take it slow. He snatched the massive dildo from the table and the bottle of lube and dashed upstairs with his prize in his hands.

Jayme got to his bedroom and quickly closed the door breathing heavily as he took a moment to compose himself. He was tossed the huge toy onto his bed and turned on his computer, his mind swirling with the events of the night. From Cassie taking his masculinity and fucking him senseless with her strapon, to finding out that it was all partially his moms plan. To make things worse his little clit was leaking into his thong and he had an burning need for a release of his pent up excitement. He quickly took his shirt and jeans off and went to his favourite website looking for something to watch while he played with his prize for the night. He scrolled down through a few videos and there she was, that same pornstar he had been watching for the last few days. He randomly chose one of her videos and went over to sit on his bed.

The video started playing and it was a scene with her on all fours with her hair in a ponytail. She was enthusiastically getting fucked from both ends by men with huge cocks with her small soft cock swinging with every thrust. Jayme could not help but feel a bit jealous of her and all the attention she was getting.

He reached over and grabbed the massive dildo and looked at it for a moment, comparing it to the cocks on screen sliding in and out of that lucky girl, he started to rub his new clit through the soft material of his thong, feeling how damp they were with his arousal. He quickly decided that he needed the dildo inside of him, it was like a newfound desire and he could not resist it. He took off the thong and tossed them aside and poured a bit of lube onto his fingers, laying on his side facing his computer he reached back and gently rubbed his tight asshole sending tingles up his back. He slowly worked one lubed finger into himself and then two, quickly deciding he was ready he poured a generous amount of lube onto the bulbous head of the rubber cock and started to push it against his tight hole. His heart started to race as he felt it pushing its way inside, sliding past any meager resistance deep inside his ass. Giving him that fell feeling he has felt earlier when Cassie had fucked him. He let out a soft whimper as his little clit started leaking down his thigh.

He worked the first 6 inches into his tight hole before pulling out and starting to push the rubber cock back into his ass. It was stretching him out and hitting sensitive spots he never knew he had, sending waves of pleasure all over his body. He was falling in love with the feeling of something thick in his tight little hole. After a few thrusts he had most of the huge toy inside himself. 'that seemed to go in faster and easier than earlier when Cass was working her huge cock into me' he thought to himself. He looked up at the computer screen, watching that beautiful woman get fucked by two studs, wishing he was in her place. He started to thrust the huge toy in a matching rhythm with the men on screen, moaning in pure pleasure at the feeling. The woman in the video reached down and started to stroke her little cock and Jayme reached down with his spare hand to play with his little clit, sending him over the edge into orgasmic bliss. Burying the massive dildo inside of himself he stroked his clit in circles as it dribbled out a tiny bit of clear fluid, he spasmed with pleasure moaning and thrusting into his hand with the cock that was no longer there.

After a few moments he came back to reality, realizing how loud he had been he sheepishly pulled the massive dildo from his ass. It slid out with a little pop leaving his hole gaping and feeling empty, almost begging for him to slide it back in. Jayme got up and wobbled over to his desk and grabbed a hand towel to clean himself up. His mind was swirling with a mixture of confusing thoughts as he wiped himself up and put his thong back on, enjoying the feeling of the soft fabric sliding up his legs and cupping the remains of his manhood. 'was I always turned on by the idea of getting fucked or did the condom do something to change what I'm attracted to?' He wondered while washing the dildo in the bathroom before heading to bed.

Chapter 4

The following morning had been a little awkward and uneventful with Tara making them breakfast and coffee in the morning and when Jayme was in the shower that morning she had gone into his room to retrieve her toy and grab his laundry. After Jayme got out of the shower he realized she had also taken all of his underwear and left a pair of lacy pink panties on his bed for him to wear today with a note that read: "Get yourself dressed and ready, we are going shopping today!"

The day was a blur of his mom dragging him from shop to shop, buying him a few new sets of androgynous clothing that he had to admit looked great on his feminine frame. Jayme swears she also tossed a skirt in the basket when he was not looking but he did not give it much thought. The most embarrassing part was Victoria's Secret. He had never been inside one before and never even really looked inside one of those stores, yet here he was being dragged into one by his mother. The girl working there, a beautiful woman with long brown hair and an hourglass figure named Becky, seemed to know his mom already. Looking at Jayme with a knowing look she winked and said they have plenty of things in store that would fit him perfectly.

Jayme has never blushed quite that hard before but he went along with it. Picking out a dozen pairs of panties and thongs. From lacey and sexy to plain and comfy pairs, he was set up with an all-new wardrobe as far as his underwear was concerned.

"Just one more stop to make before we head home." Tara said as they drove out of the mall parking lot. "Since you have been such a good sport and it sounded like you really enjoyed yourself last night I'm gonna treat you to something special!"

Jayme immediately gets suspicious of his mom but resigned himself to being a puppet of hers for the day. "What do you mean something special?" Jayme asked.

"Oh you will see." She said with a wink.

They drove for about 15 minutes just listening to the radio until arriving in the parking lot of a sex shop on the outskirts of town. The building looked to be well taken care of with all the signs lit up, advertising different toys, videos, outfits and booths. 'Wonder what the booths are for? Do they mean changing booths to try on the outfits?' Jayme wondered.

"Come on let's head in! I figured since you had so much fun with my dildo last night that I would get you one of your own." Tara said as they walked up to the front door. All the windows of the store were fogged up to obscure the people and contents inside from anyone passing by.

Upon entering the store it was like walking into another world. The inside of the shop was well lit and had a friendly atmosphere to it. There was row after row of all the things you would expect from a sex store, but Jayme had never seen any of it in person.

"Take a look around and see if anything catches your eye." Tara said before walking over to the person working the till at front of the store, a cute goth girl with short black hair that had a green streak running through her bangs.

Jayme walked in noticing there was only a few people inside and mostly everyone was minding their own business. He walked up one aisle that was full of leather bondage gear, from outfits that were mostly straps and buckles to riding crops, on the next aisle there were shelves full of every kind of dildo he could imagine. Big to small, every colour of the rainbow. Even some that were replicas of famous porn stars. Along one side of the store there were racks of sexy outfits, from see through teddys to crotchless panties. He was busy admiring a cute black outfit that had stockings, a garter belt, tiny G-string panties and a sheer teddy to top it off when he mom walked over to him with the girl from the front.

"I think you would look cute in that one." The girl remarked with a smile. Her name tag read 'Sarah'.

"I agree, how much is that altogether?" Tara responded, reaching for the price tag. Jayme was flushed with embarrassment at being caught admiring the cute outfit but deep down he felt himself agreeing with them. This outfit would look good on him.

"Oh don't worry about the tag, I can get you a friends discount." Sarah said. "And if you want to see how it fits you can go try it all on in the back before you buy it." She gave Tara a wink when he said that last part.

"I would like that." Jayme said, finally finding his voice.

His mom gave Sarah a knowing smile.

Sarah led them to the back of the building to a hallway behind some curtains and told him to use the last booth to try on the outfit. "Usually people just use the booths to watch movies here, but don't worry about that."

Jayme walked into the last booth, clutching the outfit in his hands, locking the door behind himself. There was a few hangers on the door and a bench along one of the walls, with a tv on the backwall. While he was undressing he noticed that there was a coin slot on the TV. 'I guess its coin operated, I suppose there is no harm in seeing what's on there...' He wondered to himself. Grabbing a couple coins out of his pocket and putting them into the slot. The TV turns on and there are a few options on screen. He scrolled the titles for a moment before picking one with a cute blonde girl on her knees in front of a well-built man with a thick cock. She happily sucked and jerked his cock, moaning like it was the most amazing thing she has ever tasted. 'lucky her' Jayme thought.

Putting on the outfit was a little challenging but Jayme managed to workout how it all fit together. He was in love with how the silky fabric brushed against his skin and how the tiny G-string was just big enough to cover his little nub but left nothing to imagination. Looking down it was clear that he was not born a woman but had nothing that could be considered "masculine" between his legs. The thought made Jayme smile and his little nub throbbed in agreement. He looked around and realized that there was no mirror in the booth. 'How am I supposed to get a proper view if there is no mirror?' Jayme wondered for a moment. Then he remembered his cell phone! 'Ill just snap a few selfies and see how it looks!'

He grabbed his phone and snapped a couple pics in a couple different poses, making sure to get a good pic of his ass. 'I really look amazing in this, almost like a girl...' His thoughts were interrupted by a gentle knock on the wall of his booth. He was confused for a moment when he saw a cock sticking through a hole in the wall. He had been so wrapped up in his sexy outfit and the porn playing on the TV that he had missed a hole in the wall between his booth and the one beside it! Caught like a deer in the headlights he just stared at it for a few moments, taking in the sight. He had never seen another cock before in person and this one was at least twice as big as his used to be, long and thick. He could see it bobbing a little, throbbing with its owners heartbeat getting bigger with every throb. Almost sticking straight out from the wall, it had to be at least 8 inches and uncut.

There was another gentle knock that snapped him out of his thoughts, he realized his mouth was watering at the sight of it and his clit was dribbling into his panties. He felt compelled to touch it, reaching out with his hand and gently wrapping his fingers around the thick shaft, it jumped when he touched it and started getting firmer. He could feel it throb in his hand. 'I'm really turning this guy on.' He thought with a smile as he started to slowly stroke the cock, admiring how warm it felt in his hand. Soft to the touch but hard as iron at the same time. A little drop of precum oozed out of the tip and Jayme decided he just had to know how it tasted.