His Aunt Nicole

[RibbonBound]

Excited to see another chapter!  Poor little Tim, squirming in his outfit pretending he doesn't love all the attention.  So thoughtful that a gag was provided to save him from having to answer awkward questions!  Can't wait to see where the adventures head next! 
Thanks again for such a lovely story!

[Simonssister]

Chapter 398.

Maria closed an hour early that day.  It meant she missed the after school trade, but she had a reason.
“Gwen?  Can you tidy up for me?  I need to have a chat with Tim here.  Tim, follow me.”
She led him into what appeared to be the stockroom.  She sat down in a chair and beckoned him to stand before her.
“I want to talk to you about something Tim.  Something you may not think about enough yourself.  Your future.”  Tim looked puzzled.  He made a questioning “mm?”
“It wasn’t a whim that Connie brought you here today.  I asked her to.  We go back a long way.  I used to work for ESDS, and then the teashop became available, and I had to make a decision.  In the end I plumped for the teashop.  I’d always fancied running a place like this – I started off in catering – and much as I regretted leaving Cassandra and the others, I think it was the right thing to do.  When I first saw your photos I knew I had to get to meet you.  You see, I had a particular role at ESDS.  I was the femboy trainer.  Do you know what that is?  I mean, do you know what a femboy is?  A real femboy, not just a pretty guy in a dress?”
Tim shook his head.
“I’ll explain.  A real femboy is a boy who most people would immediately take to be a girl – not just any girl, but an eye-catchingly, head-turningly pretty girl.  When I saw you, I wished I could be back at ESDS, helping you, training you, to be a femboy.  Because believe me, you would make a great one.  And I’m pretty sure you would love it.”
Tim frowned, and shook his head doubtfully.
“Hear me out.  I know all about your pageboy antics.  You wouldn’t have to abandon that project.  But if you had the training to be a femboy I believe you could find true satisfaction.  A good femboy – and you would be a good one – appeals to everyone.  Not only do women find them fascinating, but men as well.  For women, especially the young generation, who find the traditional macho types simply boring, the idea of a young man confident enough to present as a girl, sensitive enough to understand the allure of female clothing, and sensual enough to enjoy the amalgam of male and female sexuality, is exciting and incredibly sexy.  For men, physical attractiveness is the immediate turn-on.  But when they realise that the object of their desire is actually male, well…  There may be a moment or two of confusion, but once aroused, a man’s sexual attraction cannot easily be suppressed.  Moreover most men have in their psyches an element of homosexuality.  Most will deny this, but it remains true, whether from the love of male comradeship or the underlying fear of women.  So chuck that into the mix and they’re hooked!  The very reason a femboy is so devastatingly attractive is that element of maleness in his looks which adds a spice to the female allure.  For a male it is incredibly powerful.  The femboy’s looks allow them the perfect excuse to flirt, the male element, when subtly present, breaks down all psychological and social barriers.  But it also acts as a protection, since the man is still slightly hesitant, still daunted, still embarrassed.  That why the femboy is the most powerful of all sexual beings.”
Tim was staring at Maria now, though his eyes were unfocussed, as the possibilities began to take shape in his imagination.  To be the fantasy of both sexes!  Women and men…  Would Bobby like him as a femboy?  He liked him as a boy, but…  But how could he be more feminine than, say, he was at the present?
Maria must have been reading his mind.
“Just wearing a pretty latex dress doesn’t make you a femboy.  Here, let me show you.” 
She picked up her phone, scrolled through the gallery, and finally found what she was looking for. 
“For example, this boy, Carl, was one of my first projects.  This is what he looked like after I’d finished with him.  We named him Caroline.  I was so excited.  So was he…”
She held up her phone for him to see.  His eyes widened.  If he hadn’t been firmly ball-gagged, he would have gaped as well.
“That’s a boy?” he thought.  He experienced an involuntary thrill of excitement.  Really?  He’s so fuc-king beautiful…
“Like to see some others?”
He nodded – a little too eagerly – and immediately blushed.

[Simonssister]

Chapter 399.

Maria smiled knowingly.  “Okay.  This me with Rochelle, aka Rory.  That isn’t his real hair.  God knows how long it would have taken to grow it that long – he always wore it cropped.  You can see how happy she is as a femboy.  Rory was a bit of a tearaway when he was a boy.  You can still see the mischief in her face, right?  Tim?”
Tim was staring.  His mind was in a ferment.  That girl – that guy – was drop-dead gorgeous.  Just looking at her picture he felt attracted to her in a weirdly intense way.  But she was really a boy!  Maybe…  Could that be the reason?  It was very disconcerting…
“Are you all right?  You look pale.  Here, let’s get that gag off so you can breathe.”
She unbuckled one side of his ball-gag.  What a relief!  His jaw ached, but he could speak and breathe.
“Th-thanks, Maria…”
“Connie made me promise not to, but in any case I need to know what you think.  Does that feel better?”
“Yeah…  Much.  Thanks.”  He exercised his jaw.  “Can I…  Can I see, er, Rochelle again?”
“Here…”
He couldn’t get over it.  He swallowed, and bit his lip.  He pretended to be unaffected.
“Yeah, he’s really very good-looking.  I ‘spect he was already pretty cute.  It’s not something I could ever achieve…”
Maria had a knowing smile on her face.  She knew he was really gobsmacked – turned upside-down in fact.
“No, he was very ordinary.  He had some minor facial surgery, purely to slim out his nose a little.  But you have a lovely cute nose, Tim.  All you’d need is a really good makeover by someone who really knows their stuff.  The figure we shaped using a very fine light corset, and then enhanced it with these pretty cinched dresses.  Here. let me show you another I’m particularly proud of.  Paul.  He was such a sulky boy.  He took loads of persuading.  But in the end he went for it.  He even had some minor breast enhancement, at his own request.  But he definitely preferred boys, and once he was finished he really came into his element.  From that moment on he was happy and carefree.  Yes.  Pauline.  Here he is.”
She held up the phone.  Tim did a double-take.
“That’s a…  That’s…Paul?  Pauline, I mean?”
“Yes.  So cute, don’t you think?”
Tim was speechless.  “Paul” looked like the sort of girl he turn somersaults for.  His mouth was dry and his heart fluttering.  This was crazy…  Why did these boys affect him so much?  And why did he…if he couldn’t have them…then, want to be like them?  He felt slightly faint.  Maria perceived this, stood up, and helped him into the chair.  She had no idea he was going to be so deeply affected.  But she was delighted he was.
“S-sorry, Maria…  I’ve been standing for so long…”
“Of course, dear.  I apologise.  I should have realised.  Just rest there as long as you like.”
“Thank you.”  He paused.  “Are there, er…any more…?”

[Simonssister]

Chapter 400.

“Oh, let me see…  Somewhere I have a hard drive with all of them on.  But there’s just a few on my phone…  They’re all together in this one album.  There’s three you haven’t seen – Adrian, Nicholas and Samuel.  They’re under their femboy names, of course.  You can look at it, but don’t look at anything else, okay?  I’m just going to see how Gwen’s getting on.  Connie and the others will be back in…let me see… about an hour or so.  Just sit there quietly, all right?  I’ll bring you tea and a couple of cakes.”
“Thanks, Maria…”

Tim was left alone to goggle at the photos.  There were six in all.  The ones he hadn’t seen were entitled “Adriana”, “Nikki”, and “Sammi”.  Adriana was wearing school uniform, Nikki a leather miniskirt, and Sammi a very short yellow creation with a sort of little tutu skirt.  She looked as though she was at a party – maybe a wedding!  You could even see her panties.  Was it her panties?  Something…  Tim went hot and cold.  Was that…?  It couldn’t be…

He studied all the photos again, carefully.  The “boys” all looked so great.  And pretty comfortable in their outfits.  Maria returned carrying a tray with a mug of tea and a plate with a selection of cakes.  She pulled up a box and set it down, then went and fetched another chair for herself.  She sat down.
“Well?  Like them?”
“They’re all…gorgeous…” 
“Yes…they are.  Adriana…  He went to a boys’ boarding school.  He was always jealous of schoolgirls in their pretty uniforms.  That’s his favourite outfit now.  Amazing how popular he is with the guys.  And Nicholas…  Very traditional upbringing.  Now as a girl he can dress as cool as he likes.  He wears the tiniest of tops, or nothing at all, just a jacket.  After all, he’s got nothing to hide…”
“This one…Sammi.  Her skirt is so short…”
“Ah.  Yes.  You noticed.  That's rather naughty.  We thought we’d get away with it, but when she started moving about her dress rode up and oops, there is was, peeping out.  Her chastity device.”
“Is that…?”
“Yes.  Her little thing all tucked up neatly in its little cage.  It’s de rigueur for every femboy, of course.  If you’re going to present as a girl you accept it gladly.”
“Isn’t it…uncomfortable?”
“For some, but only at first.  In that interim period when you’re getting loads of attention and you can’t help getting over-excited.  But you quickly learn to control yourself - it's a matter of necessity - and several of them have told me that the constraint is actually the source of a sort of sexual high, a sustained sexual excitement that’s almost like being on drugs!  Especially in social situations like parties or clubs.  It becomes addictive.  There’s no pressure to perform.  The pleasure just fills your whole body.”
Tim shivered.  He could almost imagine it.  But he wanted desperately to see what it really felt like.
“So, Tim…  Do you think it’s something you might want to experience one day?”
“I…  Maybe…  I would like to look as attractive as them…”
“Hmm.  Suppose they were girls and not boys…”
“No…  I like the fact they’re boys…  It’s somehow sexier…”
“Aha…interesting…”  She patted his cheek.  “I think you should try…  You may surprise yourself…”
Tim didn’t reply, but bit his lower lip again.  He was aware he had an erection which wouldn’t subside.  Maria could see it out of the corner of her eye, stretching the latex panties she had given him.  But she said nothing.
“I wonder if…  These photos…”
“I’ll send them to you, Tim.  No probs.  They may help you to decide.  If you do, tell me or Connie or Cassandra.  I’m sure they’ll be able to accommodate you.  In my opinion you’d make a perfect femboy.
Tim nodded.
Someone was knocking at the teashop window.
“I bet that’s them.  They’re early.  Stay here.  I’ll go see.”

[Simonssister]

Chapter 401.

Maria went out into the teashop.  But it was only Gwen.  She’d cleared up everything and left.  She’d knocked on the window just to wave goodbye, not wanting to disturb them in the back room.  Gwen was very diplomatic.
And she had good reason.  Maria, for all her homely appearance, was quite a wild one on the sly.  Reminiscing about her work at ESDS had brought back memories.  Training the femboys had been a labour of love – often literally.  And now she had a new prospective volunteer, and she was determined to keep him sweet.
She checked the time.  “I reckon I’ve got at least half an hour,” she murmured.
She returned to the stockroom, locking the door behind her.  Tim was still staring at her phone, one hand suspiciously high up on his thigh.  She noticed it was the photo of Sammi.
“So you like my babies,” she smiled, taking her phone from him and slipping it into her pocket.  “I’ll send them to you this evening, and any more I can find.  But for now we’d better get that gag back on in case Connie turns up early.  No, don’t get up.  Stay where you are.  I’ll fix it.”
She bucked up the ball-gag, if anything tighter than before.  She needed to make sure he didn’t make too much noise.
“Now, Tim…  Just relax.  I’m going to give you some much-needed therapy.”
Tim looked at her questioningly.  She took a pair of surgical gloves from a box on a shelf, and pulled them on.  She knelt down.  His eyes widened in surprise, and he went to rise, but she gently but firmly pushed him back into his seat. 
She contemplated his stretched panties.  “Dear me, you are in a state, aren’t you?  Let Maria see…  Open your legs just a little…  That’s my good boy…”
She hooked a finger in one leg of his panties, pulled, and drew it to one side, freeing his tumescent boyhood.
“Gosh…  If you do decide to become a femboy, you're going to need a good robust device to keep this under control…  However did you get through that wedding without one?  Never mind.  Relief is at hand.” 
Tim stared.  Was she going to...?  He really hoped so...

He wasn’t disappointed.  It was even better than he was hoping.  Maria played with it for a while, pushing the foreskin back and tickling the gleaming head with the tip of one finger.  Then, taking a breath, she pushed her lips over the tip, and conducted a thorough exploration of the glans with the tip of her tongue, sending waves of pleasure flooding through his body, making him squirm and groan.  She briefly drew back.
“Take it easy, darling…  There's no hurry.  No-one can disturb us.  Just relax and enjoy…”

She guessed he had probably never had a really good blow-job in his life, so she was determined to make this first time a memorable occasion.  She proceeded with experienced restraint, keeping him on the edge as long as possible.  Tim himself tried to make as little fuss as possible, but he was soon trembling with arousal. 
“Such a sweet guy – in every sense,” thought Maria, as she rocked gently back and forth, stopping every few seconds to allow him to compose himself.  She took her time, revelling in his responsiveness.  She had quite a small mouth, and her lips were stretched tight around the circ-umference of the shaft, heightening Tim’s sensitivity.  She worked slowly and gently, intent upon making his pleasure last as long as possible.  But at last he could hold back no longer.  She felt him harden again, and knew he had gone over the edge.  He came, gripping the seat of the chair, shaking violently and emitting a series of muffled but unconstrained sobs, like an animal in distress.  Maria, despite her best intentions, was unable to cope with the bursts of c-um that filled her mouth over and over, and ended up smothered from her nose to her lap.

They both took a minute or so to recover.  Tim looked down at her, and his expression was so apologetic that Maria had to laugh out loud.
“Silly boy!  I enjoyed that as much as I hope you did!”
Tim tried to smile and nodded vigorously.  He now had a quite different view of Maria than he had a few minutes before.
But for the second time they were interrupted by a knocking at the window.
“Shit!  That must be them!  Tim, sort yourself out.  Tissues on the shelf.”
The knocking was repeated.
“Damn, Connie!  Give us a minute!”
She hurriedly wiped her face.  “Oh my god, my coat!  Where’s my clean coat?  Damn, under the counter!”  She ripped off the slimy garment.  Underneath her top and skirt were also sticky.  The knocking was repeated.  “For fuc-k’s sake, Connie…” 
Tim had risen to his feet, trying to make himself respectable, but looking slightly dazed.
“I’ll stall them.  Sort yourself out as quick as you can!”
She ran to the door, composed herself, assumed a bland smile, and walked into the shop.  Yes, there they were, all three, peering through the window.  She waved, and casually searched for her other housecoat.  It took a few minutes, but she couldn’t go to the door like this.  Connie was calling.
“Come on, Maria…  We’ve been waiting out here and we need some coffee pronto…”
“Just coming…”
She struggled into her blue housecoat, and fumbled with the buttons as she made her way to the shop door.  She unlocked it.
“Come in…”
“Why so long?  What were you up to?  Where’s Tim?”
“H-he’s out the back…”  She added, weakly,  “we were…er, I was showing him how we organise the stock…”
Connie looked a her with a cynical raise of the eyebrows.  She knew something of Maria’s reputation. 
“Really.  That must have been exciting for him.  Do you know you have some tissue stuck to your lip?”
“Oh, have I?”
She rubbed her lips nervously.  If she’d tried she couldn’t have looked at more guilty.
“Can we have coffee?  We’re parched.”
They sat down, and Maria went behind the counter.
“So…  Where’s the boy?”
The stockroom door opened slowly, and Tim emerged, also looking guilty, and red-faced into the bargain.
“Did you have fun in the stockroom, Tim?”
“W-what?”  He looked from Connie to Maria, and back again, terrified.
“Maria tells me she was showing you how they organise the stock.”
“She was?”  Relief.   A pause.  “Oh!  Yes, that’s right…”
For some reason, all three women burst out laughing.
“Come and have coffee with us.  And you, Maria, yeah?”