A Very Special Boy Ch. 03

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Ella meets Nick's Step-Mom Dava.
4.8k words
4.65
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Part 3 of the 7 part series

Updated 06/14/2023
Created 09/18/2022
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Chapter 3

Dava was in the kitchen laying out the food when Nick entered followed by Ella.

"Finally dinner's ready, oh hello I didn't know Nickolas had company, you must be Ella?" Dava asked while obviously noticing the strong smell of weed.

"Yeah that's me, so nice to meet you, Nick has told me so many good things about you." Ella beamed.

"It's great to meet you too, you've made quite the impression on Nick who reeks like a hippie by the way." Dava said looking at Nick. "It's fine." She giggled. "I was young once too, I've tried ganja."

"No one call's it ganja anymore." Nick joked, relieved he wasn't in trouble.

Dava dished out the Chinese food between the three of them while swapping compliments with Ella.

"I really love that skirt you're wearing, so stylish." Dava said.

"Well Nick actually picked this one for me today, we were shopping for hours and he picked out ALL of my clothes, he has such good tase!" Ella said to Nick's surprise.

"Really? I didn't know he had such a good eye for fashion, you should be dressing our models dear." Dava said proudly.

"What's that about models?" Ella quizzed.

"Oh I run a small modelling firm, I only manage nine women but they are all naturals." It was clear Dava was proud of her work.

"Thats so exciting! Have you ever considered Nick as a model?" Ella asked.

Nick was shocked, what did she mean by that? He obviously wasn't model material, he was short, thin with no muscles.

"Oh we only use women but he's been with me to a few shoots and I think the girls made him a little nervous. He's always been a sensitive kind of soul." Dava said rubbing Nick's arm.

Ella smiled and said "He really is, thats what I love about him, he listens to what a woman wants with an open mind, almost like he gets what it's like being a woman." Ella touched his other arm.

Nick should have felt emasculated but instead he felt proud in a way, here were two women telling him that all the things he thought were his weaknesses were actually strength's. He didn't have a big dick, he didn't have muscles but he was respectful to women and tried so hard to please them. Please them in ways men would't even think about. As they ate dinner Nick gradually got used to having the plug in, he only noticed it when he shifted in his seat, it started to feel quite pleasant and he found himself rocking back and forth slightly, almost like he was trying to fuck himself.

"Would you mind if I used the bathroom?" Ella asked.

"Yes of course, do you know where it is?"

"I do, thanks." Ella went upstairs but instead of the bathroom she found her way into Dava's room and went to her dresser. She opened the top drawer and found what she was looking for, she grabbed a few pairs of Dava's panties, not enough to be immediately noticeable. Panties in hand she made for Nick's room and his underwear drawer, she emptied all his underwear into one of her bags and put in all the lingerie Nick had picked out that day as well as Dava's panties and a few bottles of poppers. She took the smaller pink dildo and the big realistic dildo and put them under Nick's pillow then hung the remaining outfits up in his closet before going downstairs. They finished their meal with Dava really liking her Step-Son's new girlfriend. Ella grabbed her bags and changed into her own clothes, said her goodbyes and went home.

"I REALLY like her, I think she'll be so good for you." Said Dava happily.

"Thanks Mom so do I, she's already taught me so much."

They talked a little more before Nick went to his room where he received a text from Ella.

"It was great meeting your Mom, I love her so much! Today was a lot of fun, sorry we got cut short but I'll make it up to you soon. How's you juicy ass doing babe?"

Nick realized he still had the plug in and replied

"I forgot I had it in, I feel it when I walk though."

"I knew your ass could take it babe but I want to know how it feels in you." Nick wasn't sure what to say, he had to admit now it was in it felt alright.

"It hurt at first but it's getting kinda nice." He typed.

"Well duh... guys have something called a p-spot, it's like your g-spot, when it get's stimulated it gives you a mind blowing orgasm."

That last part really interested Nick, he never thought anything in his ass could make him cum but he couldn't deny this felt good and a mind blowing orgasm was too tempting to turn down.

"Here watch this." Ella sent a link to a porn video, it was the redhead dominatrix fucking a slave up the ass.

He had seen it before but always felt uncomfortable watching a guy get fucked, especially if the guy had a big dick. This time he looked at the guys ass, taking a huge black strap-on dildo, then looked at his face, in pure ecstacy then his ass again and so on. Nick stripped off all but his panties, he was starting to like them too and got into bed. As he did he felt something next to him, under his pillow were the two dildos her picked out for Ella. Had she forgotten them?

He remembered that the smaller one had been in her pussy if only for a moment. He brought it up to his nose and took a sniff, it was so sweet, he was so horny he couldn't think. He kept taking deep breaths as he watched the video, the redhead pulled out of her slave and he immediately dropped to his knees and opened his mouth. She grabbed the back of his head and started to fuck his mouth, Nick was transfixed, before he knew it he was mindlessly sucking on the dildo and playing with his nipples, god his nipples felt so good lately. After sucking it clean of any remaining juices his mind wandered to the other dildo, the 9" realistic one. Weirdly he wasn't intimidated by it anymore, he remembered seeing it in the store and being lost looking at it.

As he put it in his mouth he couldn't get it very far down but the feeling of having something to suck on was so enthralling, he felt like he could do this forever, it was so natural going in and out of his mouth. He felt an orgasm build up as he played with his nipples, his dick started to leak without even being touched and he slammed the dildo into his mouth as far as he could while he convulsed from cumming so hard. When he had calmed down he reached into his panties and bought out a big drop of his cum, new thoughts started swirling in his mind,what did it taste like? Why did he want to know? He brought it up to his nose and took a sniff. It smelled a little better than last time, he brought the finger to his mouth and stuck out his tongue, he just barely touched the cum on his finger then took it away. It wasn't bad, strangely nice actually. He'd always hated the mess, hated accidentally getting it on his leg or stomach while masturbating, how could he possibly go from that to almost sticking a finger dipped in it in his mouth? Where were these idea's coming from and why did they turn him on so much? He couldn't be gay, he liked girl's, he worshipped them really, Sure he was wearing pantie's and had a butt plug in his ass but this was all in order to have some kinky sex with a beautiful woman, someone like him could never be with a woman like Ella without jumping through a few hoop's

He cleaned himself off and took off his cum stained panties, he would have to wash them himself to keep from being caught. He went to his dresser and opened the top drawer and was shocked to find not his underwear but three full lingerie sets and some other loose panties. Did Ella do this? Why? Did she leave them for herself? But then where was his underwear? Too tired to think he grabbed a pair of the ones he didn't recognize, they were white cotton, soft and plain, he didn't pick those ones in the store but if he had to wear panties then these were the best choice, though the others did look incredibly sexy. Nick thought about how they would feel on his smooth skin. He also noticed the little bottles that Ella had him sniff to get the plug in, maybe they were to help him get it back out? He inhaled one a few times and gradually eased the plug out, it wasn't easy but felt strangely good being pulled out. With a pop Nick pulled it free and was overcome by a sense of emptiness, missing the reassuring feeling of being filled up. He compared it's size to the pink dildo Ella used. The plug wasn't as long but it was wider than the dildo.

"I could probably fit that in me." Nick muttered without thinking before snapping to his sense's and hiding it in his top drawer.

Ella was furiously masturbating as she watched the show from his webcam, she watched as he came sucking on not the small, pink dildo with her pussy juice's on it but the big, realistic dildo, she watched as he mindlessly brought a drop of his cum to his lip's and she moaned loudly as he could only bring himself to taste a miniscule amount but the thought was in his head and it wouldn't leave so easy. His training was going faster than she expected, maybe he was always meant to be a sissy? He wasn't putting up much of a fight, in fact it barely took much effort to wrap him completely around her finger. He certainly was never going to be a man, not a real one. She fell asleep thinking of everything she had in store for him, satisfied with her work so far.

Nick awoke to the familiar feeling of his panties coated with cum. His dreams were getting more vivid, he remembered being fucked by Ella who was using the 9" realistic dildo as a strap-on. It felt amazing, he was so happy someone found him worthwhile enough to fuck, someone wanted him enough to bend him over like a bitch and passionately fuck him as he moaned in ecstacy. As he came from being fucked Ella pulled out of him and he knew exactly what to do, on his knees in front of her he sucked and sucked on the cock in front of him. He forgot all about Ella, there was just this cock. This magnificent, meaty, warm, tasty cock. He sucked for what seemed like an eternity, loving the shape and flavour of this cock until he heard a grunt, it wasn't a woman's grunt, it was a man's though Nick couldn't focus on that, he was busy trying to swallow every last drop of his delicious, warm cum flowing from this prime specimen of manhood.

He got out of bed and went for a shower, after getting dried he took out his earbuds and swallowed his first dose of vitamins for the day then went to get dressed. Without really thinking about it he grabbed a pair of panties and slipped them up his smooth, hairless legs. He was definitely getting used to them, admiring himself in the mirror. His butt looked amazing in the panties and he only had a slight bulge in the front which he was strangely happy about. He ran his hands up to his chest and felt lightning as he grazed his nipples, they were so puffy and sensitive. He had to tear himself away from playing with them all day and decided to get dressed. He opened his closet, relieved he still had clothes, more clothes actually, these were the outfits he picked out with Ella yesterday. He stopped to admire them, every item was just so sexy. Nick wasn't thinking about what the clothes would look like on other women, he was just thinking about how sexy the clothes themselves were. No one would know if he just tried them on once, maybe he just needed to get it out of his system? Beside's modern girl's really liked the guy's with a feminine side, they made them feel safe. He picked the black tanktop and the pink, white and black tartan skirt and held them in front of himself in the mirror. Fuck he actually looked pretty hot from the neck down.

"Longer hair and make-up would complete the look." He muttered not realising that was just what his earbuds were pumping into his head while he slept and exercised.

Snapping out of it he put them back and picked out his usual jeans and t-shirt look.

"Man these are so boring, you can't even see my butt properly in these." Maybe Ella would take him shopping and help him show off his assets? He spent the afternoon looking at clothes online, always ending up looking at the women's sections. The men's clothes were all so boring and unappealing but the women's were so sexy and stylish. He found himself being a little jealous of girls getting to wear such beautiful clothes.

Ella walked into the sex store and went straight to the clerk.

"Hey Frank, hows business?" She asked the tall dark haired clerk.

"Hey Ella, you alone today? Where's that lost little lamb who was with you last time?" Frank asked with a slight chuckle.

"That little beauty is why I'm here, I need your help with something. I have some up and coming talent that's looking for her big break." She said coyly.

"He was pretty, sure, but I don't know if he is the kinda she we're looking for." Said Frank sceptically.

"Maybe not now but he's got all the raw material, by the time I'm done she'll be an absolute bombshell." Ella said confidently.

"He's far from what you'd call a man but he could be something else. He's young, naive and eager to please. With the right training, the right instruction's, he could be turned into a very lucrative asset. I have big plan's for him." Ella said handing Frank her phone and played some of the footage of Nick wearing panties, sucking dildos and having wet dreams.

"Shit is this real?" Frank asked shocked.

"Yup I've got him on hormones, subliminal programming, the work's and preparing the groundwork for him 'coming out'." Ella said taking back the phone.

"I made a website looking for a certain type of person, there were quite a few bite's and I was considering some but then he messaged me. He was perfect, not much of a man, no chance of a girlfriend, no self confidence and horny as hell. I honestly felt kinda sorry for him, I could give him a life, I could give him a body to die for and all the sex in the world, I could give him the thing he want's most, to be wanted, I'll make sure he's wanted by everyone who see's him."

"Okay so what do you need from me?" Frank asked now very interested.

"I need a few thing's, more toys like butt plug's, dildo's, a collar, lot's of bondage equipment, some slutty outfit's and most importantly an underground plastic surgeon." She said as though it was a shopping list.

"Well I can help with most of that but the plastic surgeon wont come cheap." He said knowing what she was getting at.

"I'll have him sucking cock soon, craving it too and when I do he'll be in the back rooms sucking off paying customers all night." Said Ella in a matter of fact tone.

"It'll take a while to earn the kind of money you need." He said.

"I know, so we'll also sell the videos online and I've started a website documenting all his changes, people who subscribe and donate will have a small say in his development, like hair colour, outfits to wear etc. Maybe even auction off his ass too, who wouldn't want to be the first guy to christen that ass?" She was very confident about her plan.

"Well okay then, I'll contact who I need to and set things up and can give you most of the stuff right now, just one more thing." He asked. "Whats his name?"

Ella turned around and started to leave the store.

"HER name is Nicola."

Ella got back to her car putting the bags in the back. She pulled out her phone and started watching Nick's livestream. He was doing the exercises Ella made him do, listening to the hypno-workout track.

When Nick was done he had worked up a good sweat and went for a shower, after making sure he was absolutely hairless below his head he dried off and went to get changed. Nick opened his closet and stared at the sexy outfits Ella had left for him. He just couldn't resist anymore, he had to know what it felt like to wear them. He put on a pair of purple satin panties and matching bra then rolled a pair of stockings up his smooth legs. It felt amazing, he had never felt this sexy before in his life. The black tank top and pink, white and black skirt were next, followed by a pair of silver heels he had picked on their shopping trip.

Nick stared at himself in the mirror, lost in his own reflection, lost at the beautiful femboy that stared back at him. His hands mindlessly explored his body, feeling his legs, his ass, his stomach and then his breasts. These were definitely beginning to be breasts, he was almost disappointed that they weren't bigger.

"Fuck I look so hot. Have I really looked like this all this time? I wonder what Ella would think?" He said in a trance.

He was getting so horny looking at this slut in front of him when a thought popped into his head, the 5" pink jelly dildo, his reflection was that of a sultry sex vixen, she wouldn't be doing the fucking, she'd be getting fucked. He went to his dresser and grabbed the lube, poppers and dildos and dropped then on his bed.

"Okay I can do this, I want this." He reassured himself lubing up his fingers and sticking them in his ass. Fuck that felt good. He then lay on his back and put his earbuds in playing more of the hypnotic techno track. He took several deep whiffs of the poppers and lubed up the dildo he began to slide it into his tight ass, breathing deeply as he took more and more. He went slowly at first but due to the poppers quickly began to take it deeper. He was almost mindless, unable to focus on anything except this cock filling his ass, his mouth began to water, he knew exactly what was missing, grabbing the bigger dildo he rammed it into his mouth, taking cock deep from both ends. Before long he was cumming, the most intense and longest lasting orgasm of his life before lying exhausted on his bed. His belly was coated in several loads of cum, it looked delicious, glistening and inviting. He scooped a little up and licked his lips then he dropped it into his waiting mouth. It was the most amazing flavour Nick ever experienced, why didn't everything taste like this? He took the lifelike dildo he was sucking on and dipped it into the pool of cum and then began sucking it off. He did this for another half an hour, savouring every drop he could, all while Ella watched on through his webcam.

"What a little slut!" She screamed, cumming so hard she was shaking. "You are gonna drive the guy's wild and make me a lot of money."

Ella used the backdoor app that she put in Nick's phone to look at the messages between him and Dava. It looked like they didn't text much but she saw her name come up a few times, Dava was definitely happy that Nick was with Ella. Ella took a note of Dava's number and sent her a text.

"Hey Dava it was so nice finally meeting you! It's a shame we didn't have more time, how would you like a day out together? I was thinking hair and nails? Let me know! XOXO Ella" It was time to tell Dava what a sissy her Step-Son is.

After a while her phone chirped

"I'd love to, it would be so nice to get to know you more. See you tomorrow." Ella looked at the message and smiled, everything was going so smoothly, he'd be sucking and fucking real cock in no time at all.

Ella and Dava met up the next day and went to a salon, they both got manicures and pedicures while they spoke about Nick, how sweet he was, how Dava worried he would never find a girlfriend, how he seemed so much happier lately.

When they were done Ella suggested a coffee and Dava agreed, they got their drinks and sat at a table outside.

"So there's something I think I need to tell you about Nick, it's nothing to worry about or anything I just thought you should know." Ella said seriously.

"What is it? Is he okay?" The panic was obvious in Dava's voice.

"Yeah he's fine don't worry. He's better than fine actually, he's finally starting to accept who he really is."

"Who he really is?" Dava was confused.

"That's right, you know we met online right? It was a site for guy's who wanted to explore their feminine side, you know, clothes, make-up that kind of thing but they're scared to try it on their own. They can find women on there to guide them on their feminine journey and support them through it." Ella lied.

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