Pride before a Fall - Entanglement Perspectives : Part 14 - Andy 16:35 Saturday afternoon

Part 14 of "Pride before a Fall - Entanglement Perspectives".   Part 1 can be found at https://amandablogtest.blogspot.com/2019/06/pride-before-fall-entanglement_25.html .   Andy's inspirational original artwork can be found at http://smoothslicknshiny.blogspot.com/2018/04/new-art-pride-before-fall.html .   Please leave comments.

Two and half hours later Andy walked out of Maison Celeste and his mother would scarcely have recognised him.  In fact his mother did not recognise him.   The heavily tattooed blonde female trainee was just setting his new long red locks with layers of hair spray when his mother came in for her weekly wash and blow.   She’d seated herself in her regular place barely noticing the pretty girl in ripped jeans a couple of chairs away.   The girl was probably going to a Prom that evening: some lucky boy was going to be very pleased by his date.   An hour later, Andy’s mother was engrossed in a magazine and seemed not to notice the girl totter out in a tight red latex dress on 5” heels behind a somewhat taller, older lady in a white dress and light coat when they emerged from the back of the shop. 

Out on the street, Andy breathed more easily.   “Oh Andy, you are silly,” said Jane.  “She’ll have to know some time.  In fact, from some of the things she’s said, I think she already suspects.”

“I already have a problem, Aunt Jane.  How can I explain this to Nicola?   She saw me having extensions.”

“Just say you wanted to try extensions.”

“After only a couple weeks with short hair!”

“You were tired of the pixie look.”

“But red!  Red extensions with a permanent wave.”

“And what about when the manicure started?”

“Mmmm that may be a little more difficult.   How about I was taking you to a showing of ‘The Rocky Horror Picture Show’?”

“With bright red acrylics?”  A quick dab of black varnish possibly, but red acrylics?  And then when the beautician came out to do my make-up.   Everyone was looking at me.”

“OK, well maybe we were going to that new musical ‘Everybody’s Talking About Jamie’.”

“What?!  To audition?  What will Nicola think.    The looks she was giving me.”

“Is Nicola your girlfriend?” asked Jane.

“No, Auntie.  She has a boyfriend.   A fitness instructor.”

“Oooh!  Is he nice?”

“Really Auntie!”

“Well is he?”

“Yes, actually he is rather.   He’s dark haired, about six foot and got a stubbly face and big chest.”

“Which of them do you prefer?”

“Please stop it, Auntie.   I’m not going out with either of them.  Well I was going out with Nicola tonight but that’s another matter.  I just didn’t want people seeing me like this.”

“So you’re ashamed of being seen with me.”  By now they’d reached the Mercedes in the car park up the road.   They’d both attracted quite a lot of looks along: the pretty lady with her gorgeous daughter.  Or was it her young lover given how they were holding hands?  It was hard to be sure.   Both looked like they were off for a night on the town. 

“That isn’t what I said, Auntie.”

When they were inside the car, Jane spoke: “If you don’t stop complaining, I’ll take you straight home.  You don’t want that, do you?   You don’t want any more embarrassments.”

Andy knew ‘home’ didn't mean his home.  “No, Auntie.”   Andy still felt the shame of when Jane had left him at her home the last time he’d objected to going out.   She’d trussed and tied him to the foot of her bed with a ball gag so he could breath but not cry for help.   When Jane came home in the early hours of the following morning with a giggly young girl, they’d laughed at his predicament and the puddles of leakage.   At least Jane turned off his vibrator when they finally settled down to sleep for the night.   She’d left it softly humming while she was out but had changed the batteries and then turned up the butt plug to full intensity while she and her new friend made love in the darkness.  Andy had eventually fallen asleep on his moist patch of Jane’s bedroom carpet weeping tears of exhaustion and regret.   He did not want that again.

“Quite.   Plug secure?”

“Yes, Auntie,” Andy said slightly doefully.   Nicola might know about his hair and make-up but at least she needn’t know about that little embellishment.  He just hoped Celeste and Madison were discrete.  He could sure about Celeste.  But Madison?

After his hair, manicure and make-up.  Andy had gone to the back of Maison Celeste to change.    Aunt Jane was already changed.   The blouse and leather trousers had gone and she was dressed in a long white gown with grey details, a pearl choker and earrings and white Louboutins.  Andy thought she looked lovely.   She held up what looked like a flimsy length of red latex. 

“What’s that?” Andy had asked.

“Your dress, of course.”

“Where’s my dinner jacket?” 

“You haven’t got one.  This is what you’ll be wearing tonight.”

“I can’t wear that.”

  

“You can, and will, my pretty boy.  Won’t he look nice in this, Madison?  It is Madison, isn’t it?”

“Yes, Lady Jane.   That's sick.  He already looks lovely.  I’m just glad my boyfriend can’t see him.”

“Let’s get his clothes off.  You can put them in the shopping bag the dress came in.” 

“No!” Andy called out.

“Please Andy.”  His Aunt smiled.  Andy could not resist her.  A simple smile from his Aunt was all it took.   And a ‘please’ with a look of tenderness and affection.    Andy’s heart melted every time she did that.

“Yes, Auntie.”   He took off his trainers and then his jeans.   He paused.

“It all has to come off,” said Jane.   He removed his socks.  “And the rest.”

More than a little reluctantly, Andy removed his long white shirt.  Madison gasped.  The tail on Andy’s shirt had hidden a pair of black lace panties ornamented with small bows.   But the inked hairdresser was shocked for another reason.   Andy was wearing a matching black lace training bra.  Even Aunt Jane seemed surprised.

“Oh darling.  That is so sweet.  I didn’t buy you those.  Did you buy them yourself?”

“Yes, Auntie.”  Andy hung his head in embarrassment.  He’d bought them last week from Victoria’s Secret in the Mall and wanted them to be a surprise for his Auntie.  He’d claimed they were going to be a part of a present for his girlfriend which in a way they were except he was going to be the present.

“You deserve a kiss for that.”   Jane came across and gave him a long lingering kiss.  As Jane pulled away, Madison couldn’t help notice not just the tongue contact but also some stirrings down below in Andy.  The creation in front of her might look like a girl but he still had some very specific masculine tendencies.  It seemed Lady Jane liked the best of both worlds.   “It’s a shame they have to come off.   Now go to the toilet, take off your lovely lingerie, and put this in.   I’ve put some lube by the sink.”   To Madison’s astonishment, Jane handed him a shiny object with a large red ruby at its base.   Madison knew what it was.  She’d once worn one a rubber one herself when her boyfriend had asked for something extra.  But she’d not seen one as large or metallic before. 

“Do I have to, Auntie?”

“Yes.   Please.   We haven’t got long.”

Andy went to the toilet in back room.   As he closed the door, he heard the assistant ask Jane: “Is he one of them fembois?”

“Well dear, you could call him that but I can assure you he’s all boy when he needs to be,” Jane said with a knowing twinkle in her eye.    Hearing that made Andy smile and swell with pride.   He decided not to lock the door and leave it partially ajar so he could hear more of their conversation.   He reached behind him and unclipped his bra, then eased down his flimsy panties.  He was quite pleased to be out of them since they did have a tendency to itch.  A little cord hung against his thigh.  Lady Jane continued:  “But he much prefers to be a girl.   And he does make a very pretty girl, doesn’t he?” It was a shame Auntie wouldn’t see how thoughtful he’d been.  Andy smeared a little lube around his anus to ease the passage then pulled on a little cord dangling from his bottom.  There was a clacking sound as first one then a second ball emerged from the darkness.  He wiped the little love balls and put them to one side and stared at the plug.  Compared to the Ben-Wa balls, its diameter looked enormous.   The balls weren’t much more than an inch or so in diameter but this had to be an inch and three-quarters or more at its widest.

He squeezed lube from the tube and worked the slimy substance with a couple of fingers into his anus, something else began to swell.  He heard Madison reply: “Yeah, he is pretty. “ Andy started to apply lube over the head, bulb and shank of the plug.  It needed to be properly lubed since he realised it was likely to be in for a long time.     “But you’ve just given him a butt plug?” queried the young hairdresser.  “Is that what he likes?”

“Oh, never you mind about that. Just because he’s a boy, we don’t want him to be limited anatomically.    He is very feminine and I like to keep him reminded of that.  I’m sure you understand.    Anyway that’s enough questions for today,” advised Jane. Gently Andy worked the head of the plug in and out of his little ring.   His cock continued to stiffen.  It was a larger plug than he’d ever tried before and even after several partial insertions he still couldn’t take the widest part.  This was embarrassing.  He tried again and emitted slow grunts at each push.   He couldn’t see Madison and Jane exchanging knowing glances.   “How’s it going, honey?” Jane called out.

“It won’t go,” gasped Andy after another failed attempt to push the wide bulbous head through his tight ring.  His cock had started to shrivel.   Any arousal was vanishing as he struggled to take his Auntie’s large jewelled plug.

“Of course it will.   Lie down on your back, raise your knees and go at it slowly.   We’ve always found that worked in the past.”   Aunt Jane winked at Madison who smiled and giggled.

“OK, Auntie.  I’ll try.”   Andy spread out a towel and laid down.  He shivered on the hard, cold tiled floor.   With his knees raised, his bottom was not as taut.  He thought fondly of lying like that on his Aunt’s bed with his legs splayed ready to receive her ministrations when he submitted fully and truly became her girl.

“Just relax and exhale slowly, darling.   I’m sure you can take it.”  Andy closed his eyes and started to dream about his Aunt above him and the ecstasy she’d driven him to last weekend.   He tickled the tip of the plug against his perineum exactly like Auntie did.    Then Jane called again: “Just think of William.”  It was fortunate that Andy couldn’t see how Jane gave Madison another knowing wink.   Madison was getting increasingly drawn to this strong, dominant lady.

“Does he have a boyfriend, then?” asked Madison.

“No, not yet.  Not properly.  But there’s someone he goes all shy about.   Andy blushes and gets embarrassed when he’s around,” Jane said.  

Andy was still worried that he was going to be stretched and torn.   But hearing the conversation next door, his thoughts turned to William.  He thought of cuddling William.   Cuddling William naked.  Feeling  William’s cock soft against his belly. If William was above him, he wouldn’t want to disappoint his friend.  As he dreamt about William’s cock stiffening against him, his own started to tense as if to rise and greet William’s. Aunt Jane always said his cock was ‘Cute’ and ‘Nice’ but he was sure William would be larger.   He wanted his cock to stiffen against William’s.   Rather than snuggling against William in the cinema, he wanted their cocks to snuggle together.

“Is that helping, darling? I don’t hear much action.   Get those legs apart.  Open for your boyfriend.”

“He’s not my boyfriend!” yelled Andy back towards the ajar door, though every inch of his growing erection and his dilating anus told a different story.” 

“Very well, as you will, darling,” returned Jane.   “He still doesn’t want to accept his true desire,” she said to Madison.

 

Andy wanted to make William happy.    He wanted to give William pleasure.   He wanted William.  Reluctantly Andy had to admit to himself: he wanted to feel William inside him.    As he breathed out slowly, he pressed hard and the widest point of the plug passed through his tight ring.  William was in.  As soon as it passed, his bottom eagerly drew the slippery tapered  lower section of the plug inside, and his little ring closed tightly round the neck.  He let out a loud sigh.   He couldn’t see that next door Jane and Madison were smiling at each other.

“Was that nice, darling? Perhaps I should call that plug, ‘William’.  That will confuse him.” 

The wide jewelled base clamped against his bottom felt cold rather than warm like he imagined his friend would feel.     Andy hoped the disc wouldn’t chafe.  He tried to extract the plug largely to reassure himself that it would come out.  It took a bit of effort given the narrowness of the neck but after a slow steady pull his sphincter eventually widened and released the wide bulbous head. He breathed a sigh of relief.  “Everything OK in there?” Jane called through.

“Yes, Auntie.”  He looked at the plug more closely.   He should have realised that Jane would have bought the most expensive. It was perfect.  The base was chamfered with rounded edges: ‘William’ wouldn’t chafe however long he wore it.   Hastily he pushed the plug back in: it was still a struggle but it was much easier the second time. William was inside again. Secretly he was proud that he’d taken the plug.   He tried to look over his shoulder but struggled to catch a glimpse of the large red jewel covering his ‘little temple of delight’ as Jane referred to it. Part of him wanted to show off that he had taken it.  Auntie had never given him jewellery before.   It was something he wanted to wear with pride although he recognised that it might signify ownership. Aunt Jane’s ownership.   But she owned so many aspects of him: it was Auntie who had nurtured him and given him the freedom to release the inner Andy and to be what she wanted him to be.   A thought struck him that made him pause:  if Auntie owned his bottom, what would that mean for William?  He shook himself back to reality: he was being silly.   He didn’t need to worry.   Auntie had always encouraged him about William.  And she’d said that he ought to contact that nice man he’d met at Miss Rebecca’s.   It was a shame he’d lost Mr.V’s number. Part of him wanted to show off his plug to William (or maybe even Mr.V).  To show what he wanted and that he was ready.  She was happy for him to have a boyfriend though he would always be Auntie’s:  Auntie’s boy, Auntie’s girl.   Auntie’s lover?  He could always hope.    And Auntie knew that.

Andy returned to the back room holding his panties, bra and the Ben-Wa balls.   Jane looked at him   and smiled  as he entered: “Well done, honey.  Let me see.”   Andy turned.   “Bend forward slightly.   Oh, that looks lovely, doesn’t it, Madison?”

“Yes, luvverly,” murmured the assistant in awe.  “Girl, you is sick.”  Although her eyes were more focused on the delightful little erection that preceded Andy into the room standing out proudly from an entirely bald pubis.   Definitely ‘all boy’ but in the nicest possible way.   She couldn’t help also noting the shiny wisps of fluid glistening at tip of his cock   The femboi clearly liked things in his bum. 

“Did thinking about William do the trick?” Jane asked.

The assistant put her hand to her mouth and gave an exaggerated giggle.

“Please!” pleaded Andy.

“Give me your undies to put in the bag.  Oh what are these?”  Jane held up the Ben-Wa balls.   “Were you wearing these for me?  Oh that’s so thoughtful,” she said jingling the balls in her hand and making the inner weights rattle.   She gave him another big kiss.   “But you look far prettier plugged and all that clicking and clacking would get you far too excited when we’re dancing.   Now since that plug seems to remind you of William, we need to stop you getting all excited.   You don’t want to embarrass Madison with any silly bulges.”

“Oh, Auntie!” exclaimed Andy, desperate not to catch Madison’s eye. It was all very well his Aunt guessing at his true feelings, but he didn’t want everyone else knowing.  It was demeaning enough having her know that he voluntarily wore love beads and that his Aunt liked to have him plugged.   He was sure she’d already guessed what else his Aunt might be doing, without her knowing that he wanted a boyfriend.   And worse, that he was the submissive.   He might choose to think of Auntie as his girlfriend but Madison would know that he was her ‘wife’ and maybe one day would be the same to a boyfriend of his own.   Maybe to William?  William’s wife.    Would that be so bad?

Andy’s thoughts shifted and gave him pause.  Who else in the town had a girlfriend as pretty as Aunt Jane?   He would be the envy of most men.  And William was a handsome guy.   He wanted to have those friends and he would be very happy with the benefits that friends provided.  Did he really care what Madison thought?  Looked at like that, being a wife seemed rather a good option.

“We just need the finishing touch before you get into your dress and heels,” said Jane, holding up a long length of red ribbon.

end of Part 14