A Very Special Boy Ch. 02

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Ella takes Nick on a shopping date.
2.7k words
4.7
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Part 2 of the 7 part series

Updated 06/14/2023
Created 09/18/2022
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This is just a quick warning about a particular part of this chapter.

NEVER EVER mix viagra and poppers. This can lead to headaches, sickness, losing consciousness and even DEATH. Be safe everyone and hope you enjoy the next chapter.

*

The next day Nick awoke to his underwear being soaked in cum, something that was becoming a regular occurrence.

For some reason an idea popped into his head and piqued his curiosity, slowly he put his hand under his covers and reached down to the mess. He had never been interested in his cum before but he touched a soaking wet patch and with some on his fingers brought it to his nose.

He inhaled it's salty smell deeply, not exactly hating it but not what he expected. He cleaned up his mess and went for a shower, it wasn't until he went to clean his ears he noticed he still had his earbuds in.

"Must be getting used to them." He mumbled.

He used the razor and hair remover again before rubbing in the soothing lotion and rinsing off.

Just as he finished getting ready his phone went off.

"Hey I'm going on a shopping trip today, I need some retail therapy lol. Care to join me?" It was her.

He quickly replied in the affirmative and went to meet her in the city centre. He spotted her going into a women's fashion store and caught up with her.

"Hey you, thanks for the invite." He said behind her.

"Oh you came, great to see you baby, ready to put a dent in this card?" She waved a bank card in front of him.

Nick nodded in agreement. "Good and one more thing, I don't want you just standing there, I want honest opinions, tell me what you like, what you don't like, kay?" She was so sweet.

"Yeah sure I promise I'll be honest but I bet you look good in everything." Nick said smoothly.

"Not just what looks good, specifically what you're into." She affirmed.

Nick nodded again.

"Great!" She said looping her arm with his and walking into the store. They headed for the "trendy" section from what Nick could tell. There were skirts, fancy tops, some dresses and shoes with another isle behind it. Ella started looking through the skirts before saying something.

"Well, what one do you like?" She quizzed.

"They're all really pretty, you cant go wrong." Nick was hesitant.

"Okay then pick me out three, any three you like and they better be good ones that you've thought about." She sounded stern, for some reason Nick really responded to it.

"Of course Ella I'm sorry, I should be more considerate and open minded." He took a minute to really examine every one of the skirts trying to decide on his three favourites. One that drew his eye was a very simple though elegant leather skirt that came to just below the knee. He took it from the rack.

"Oooh such a good choice! I love your style." Nicks face beamed with pride, he made a good start now just two more.

He found a pink, white and black tartan skirt and took it off the rack.

"Och aye laddie, that's a bonnie wee kilt." She joked sounding like Groundskeeper Willie.

Okay just one more. Ah yes this was the definitely the last one to get. A miniskirt made from a shiny, silver, spacey material.

"Yeah just gorgeous babe, those will look so good. Alright task accomplished, you did very well I'm so proud of you."

Ella praised.

"Thanks, I wasn't sure if you'd like them but I was really drawn to them." He said shyly.

"You did a great job, now for you to pick me some tops to go with these." Ella said as she marched Nick to pick out three tops that he liked. He didn't hesitate before looking for what he wanted this time. He picked out three tops.

A plain pink tank-top, a black sleeveless top and a fitted white t-shirt. He did this for jackets, trousers, shoes and even lingerie! Nick loved picking out everything especially with all the praise he was getting. After all that they grabbed a quick lunch and Ella said she wanted to go to one more shop. When they finished they're meal they walked to a back alley shop with an unusual sign, Nick had never seen an adult sex shop before but he knew this was one,

"I just want to have a look." Ella giggled and forced him inside. When they got in Ella had a look around dragged Nick along with her. She stopped in front of a wide array of dildos.

"Okay babe, same deal, pick out three you like. Go on." She urged.

Nick had been good all day and he wasn't going to ruin it now. He immediately saw a realistic 9" dildo right in front of him. He just stared at it, it felt like it was the longest time he ever looked at a cock. He noticed the veins, the colour, the perfect proportions, the juicy head... Wait no he didn't like cocks. He looked around and picked a 5" pink jelly dildo, it didn't look real and it wasn't a threatening size.

"Mhmm okay." He heard Ella say.

He then found a medium sized red butt plug, she never said anything about plugs but it did speak to him. He put it in the basket.

"Interesting choice, okay we're taking this one took, you were drooling at it for long enough." She said as she grabbed the 9" realistic dildo. Shit how could he have been so stupid, screw it if he ever saw it again it would be in Ella's pussy, what's the worst that could happen? With the three sex toys they moved onto another isle, this time it was bondage gear, everything you could need to tie someone up, cuffs, chains, rope, gags, collars, tape and more.

Straight away Ella put in a pair of leather wrist and ankle cuffs, a leather collar, metal connectors, a ball gag, a padded leather blindfold and some little padlocks.

"I've always being interested in trying bondage with someone I could trust and don't lie I know you like it too, I've seen your phone remember?" She said defensively.

"Are you kidding? This is so awesome, I never imagined I'd ever get to try this stuff let alone with a beautiful woman." He said enthusiastically.

"Glad you agree baby! You're so open-minded!" Ella praised.

Again Nick swelled with pride, he was being useful, he was learning, he was on top of his game. Ho notice Ella's hand graze what looked like a black metal chastity cage.

Suddenly she spoke "Could you imagine being locked up in this by me?"

Nick was stunned, who would ever want their dick locked up?

"Don't worry I'm just kidding." Laughed Ella.

Nick let out a sigh of relief, if Ella was serious he might not have been able to refuse. They went to the counter to pay for their items and Ella added some lube as well.

"Lube just makes everything better." She whispered seductively. The clerk rang her up and bagged her purchases.

"Okay then, shall we babe?" She set off outside the store and Nick followed.

"Oh I'm sorry Nikki dead I forgot to take my card back in that store, can you be a help and take some of these bags to the parking lot? I'll meet you there and then take you home." Nick would do anything to help Ella, he would never let her down.

"Yeah sure whatever you say Ella." Nick said lightheartedly.

Ella went back into the store and bought the chastity cage size small, it may pinch to start but his dick would be losing an inch or two soon anyway. She also bought Viagra, the 'vitamins' she had been feeding Nick would start taking effect soon and his pecker would lose some strength, to combat this she would add a new 'vitamin' to his routine, one to keep him hard and needy and a few bottles of poppers. Lastly she inquired about backroom activity, the clerk gave her some times and off she went. She met Nick and put the last bag in her car, they both got in and Ella suggested they go back to Nick's place which he eagerly agree to. They arrived at Nick's house and Ella said

"Give me a hand with the bags." Nick just looked at her.

"We got some really cool stuff today and I want to take a proper look at it." She commanded, how could Nick refuse?

They both grabbed several bags and went up to Nick's room, his Step-Mom still wasn't back from work but he closed his door anyway excited about what they'd get up to. In his room Ella sparked a hidden joint and put on that same techno trance music she had Nick listening to. Then she told him to put on porn again but this time told what to watch.

"I want something kinky, some BDSM or bondage, I know you like it so put on something good." She demanded.

Nick's heart was racing, was this really happening? It was all so insane. He found one of his favourite videos, it was a hardcore lesbian bondage scene. A tall blonde Domina was toying with a butt plug in her slaves ass while her slave ate her pussy.

"Oooh that's perfect, here have some." She handed him the joint and he took deep drags on it. It felt like every time he passed it to Ella she passed it right back.

"Oh yeah I almost forgot I got you another vitamin to take, it should really put some pep in your step, you trust me right?" Asked Ella through big, beautiful eyes, giving him the pills she put in an unmarked bottle.

"Yeah of course I do." Nick obediently replied.

"Great why don't you take another round right now? Cant have too much of a good thing." She said enthusiastically.

Nick opened the containers and took a pill from each, five pills in hand he slammed them in his mouth and swallowed hard.

"My my you just thew them down there, skills." She giggled. "Shall we open some bags?"

Between the weed and the porn Nick was horny as hell.

"Yeah let's do." He said eagerly.

The first bag was the outfits, they ranged from glamourous to slutty.

"I take it you want to watch me model them?" She asked coyly.

"Well only if you want to." He said trying not to offend.

"Thats the idea but I'm going to use this to get something I want." She sounded strange.

"Oookay what do you want?" He asked a little concerned.

"I'll make you a deal, I'll model all these outfits we got today, every one just for you if you do one little thing for me? I want you to wear the panties I've been wearing today. Don't laugh or anything it's just something I'd really like to see and I promise it'll be worth it. But you have to agree." She pulled her top to show her bra strap.

Nick was reminded of his promise to keep an open mind, plus she was going to model all that for him, fair trade.

"Yeah okay Ella, I'll do it" Ella couldn't contain her excitement and hugged Nick.

"Oh thank you, thank you baby you're so sweet!" She squealed and began to strip and Nick did the same.

His thin body was still smooth all over and starting to get some fat in the right places, his ass was bigger, hips were wider and even tiny little mounds on his breasts. Ella looked at her handiwork in progress as he slipped her panties up his leg. She put on the leather skirt and black tank top while Nick's jaw nearly hit the floor.

"You know I don't think I can wait, how would you like it if I used one of those dildos on myself?" She said almost breathless.

"Yes definitely." He jumped.

"Okay just one thing." Ella said reaching into the bag "I want to to put this in." She held out the red butt plug and the 5" pink jelly dildo.

"If you let me put this in your ass I'll let you put this one in me." God it was so hard to refuse her.

"Will it hurt?" The fear in his voice clear.

"No sweetie that's what the lube is for, I'll use plenty, go slow and talk you through every second." She reassured him.

"I couldn't ever imagine doing anything like this but you make me want to try new things." He reasoned that she was doing him a favour so he should reciprocate.

"Oh my God Nikki! Thank you so much! You're fulfilling dreams here." Her enthusiasm was infectious, Nick was actually quite excited about things now.

"Okay lie down with this pillow under your tummy and stick your ass in the air." Nick did as he was told and when he was in position Ella moved behind him. "You have such a cute ass Nikki!" She said giving it a spank. She uncorked a small bottle and put it under Nick's nose.

"This is gonna help you relax and make everything feel good, don't worry it's nothing scary just take a sniff."

Nick held one nostril closed and sniffed deeply, almost immediately his head began to spin.

"Wow that's intense." Was all he managed.

"Don't worry just relax, it'll help, when you feel discomfort take a sniff."

Nick felt her lubed up fingers circle his hole then eventually slowly enter. Nick grunted but didn't say a word.

When Ella was satisfied she pulled her fingers out.

"Alright now time for the main event." She chirped. Nick took another big sniff. Ella put the plug in about halfway, giving Nick's hole time to adjust, pulling out then pushing in deeper. She repeated this for a few minutes and then pushed it all the way into him. Nick moaned loudly but still didn't speak.

"I am so proud of you baby, you did so well, how do you feel? Is it nice? She asked eagerly.

"I feel really full, like impossibly full." He panted.

"Just give it a second, your ass just needs to adjust." She said as she stroked his cheeks.

"Now that you've fulfilled a real kink of mine it's time for your side of the deal, go grab the pink dildo."

With great difficulty moving Nick got the dildo out of the bag and went back to the bed where Ella had her legs spread and panties off. This is the best day ever. Nick got his face close to Ella's warm pussy, he could feel her heat on his face.

"Okay just go easy on me, take it slow and be gentle, just like I was with you." There was a slight laugh to her voice.

"Yeah of course, I'll use a little lube too." Trying to sound useful.

"Now you're learning baby!" Ella praised. It felt great to feel her praise, it was getting almost addictive, was this love? Nick lubed up the dildo and slowly started to slide it in.

"Oh fuck yeah... yeah just like that... a little more... little more... uuuhh." She was moaning. Nick thought this was the hottest thing ever, his dick was hard and his ass was getting used to the plug. But the good times were not to last, as her moans were getting louder Nick barely heard the sound of the front door closing.

"My Mom!" Nick screamed. "Shit she cant see us like this." He was panicking, turning off the porn but strangely forgetting about the music.

"Look at me baby." She grabbed his head. "This is nothing to be ashamed of but don't worry your Mom wont find out. Put your clothes on quickly, I'll tidy these up and you can introduce me to your Mom, I've been dying to meet her." Ella laughed. Nick did as he was told, he went to take the panties of but was stopped.

"No don't take them off or the plug out, it'd be a real turn on if you kept them in, I'd owe you one." Ella cooed.

Nick hadn't refused her yet.

"Okay but get ready quick." He hushed.

"Hey Nick, you home? I brought takeout, lets eat." Dava shouted upstairs. Ella looked at Nick, gave him a deep, passionate kiss and said "Okay babe, let's meet Mom!"

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AndyPuppyDogAndyPuppyDog11 months agoAuthor

I'm not changing the story but I will put a health warning at the top.

notveryintrestingnotveryintresting11 months ago

poppers and viagra is a very dangerous combination, because they both cause a person’s blood pressure to drop. The combination can result in fainting, stroke, heart attack, and/or death.

please change the story.

Lily PegLily Pegover 1 year ago

Yes it's going in the right direction and it'll be interesting to see how she controls him and introduces more kinky activities. It must get darker and more intense as she turns the boy into a fully trained sissy.

AnonymousAnonymousover 1 year ago

This guy is awfully dumb. He meets a strange slut online, she pushes him to take pills from unlabeled bottles, wear women's clothes and does everything she says without so much as a blowjob. I just can't see a straight teenager doing that overnight like the story suggests.

orzysorzysover 1 year ago
God damn

I really like where this is going! Written very well and builds very smartly.

Just wish it won't feature any male on male or male on sissy... Just my preference.

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