Meg Saunders

Meg Saunders

Explanations: This story was written because of an email exchange between the author Meg S and myself. Meg read my series 'To My Gorgeous T-Girl Fuck-Buddy' and wrote to say she enjoyed those stories. I offered to write some of her fantasies into some kind of coherent tale. Numerous emails bounced back and forth, as Meg explained, and then enhanced her fantasy to meet, date, fuck, and then marry a transwoman.

The appearance and physical characteristics of the main character, Meg, are directly from Meg herself. Meg assures me she is completely bisexual but prefers effeminate men (she likes being fucked with a flesh cock). Denise exists, and some of the events in Denise's studio actually occurred. Those events are the source of Meg's fascination with transvestites and transgirls. The rest of the story is my imagining of how things would have progressed.

Unfortunately, I seem to have lost contact with Meg S. Her email address now bounces back to me as 'undeliverable'. Plus, Meg hasn't responded directly to any of the emails I've sent her through this site's internal mail system.

I hope Meg reads this story and likes what I've written. She seemed very pleased with the snippets I sent her when we corresponded.

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Meg leaned closer to the mirror to draw her brows a little higher and fill them slightly thicker than they really were. Then, she outlined her lusciously full lips and painted them with her favourite dark mahogany lipstick.

Satisfied with the result, Meg looked at her reflection, blew it a kiss, and said, "Damn, you're a sexy bitch!" before laughing and turning away.

Although Meg didn't really believe it, she was one 'sexy bitch'! With her dirty blonde hair, full lips, and big brown eyes, Meg turned heads wherever she was. Plus, she stood a tiny 5-foot 4-inch (163 cm) tall, weighed a petite 123 pounds (56 kg), and had an hourglass 36-27-39 figure with full C-cup breasts.

Meg thought her hips and bottom were perhaps a little too big, but she knew both boys and women loved her 'big round booty'. The thing was, Meg's 'bootay' was tightly toned and shapely because she loved going to the gym.

Meg was in a weirdly joyous mood tonight because she was going out to pick up.

'Far out,' Meg thought. 'How long has it been? Two years? Three?'

More than two, but definitely less than three, she thought. Nevertheless, she was determined to throw off the funk that had plagued her since she had thrown her girlfriend out.

'But where to go?' She wondered. 'Into Hartford and one of the dance bars where I'm sure to meet boys? Or into New Haven's gay area, where I might meet a woman?

She wasn't sure. Meg's last boyfriend tried to bash her during the argument that ended their relationship. A frying pan to his already flat face fixed that. Then, as a rebound from that experience, Meg kind of fell into the arms of her workmate and friend, Beth. Her time with Beth was fantastic at first, though.

"Best sex I've ever had," Meg told her closest friends. "That girl knows how to use a strap-on, if you know what I mean! And what she can do with her fingers and tongue! I'm telling you, who needs the trouble attached to a dick when you have that?"

But then Beth turned clingy and possessive. It had gotten so bad that Meg had found a tracking app added to her phone. The argument over that faux pas led to Meg kicking Beth out.

"No one will ever love you as much as I do," Beth wailed as Meg pushed her and her bags into an Uber.

Thinking about her previous relationships, Meg thought, 'Damn, Girl. Pick a gender! You can't keep swapping back and forth like this.'

But that little voice Meg heard when she felt frisky whispered, "Why not? You're young, girl. Plenty of time to choose someone to settle with when you're old."

When in control of herself, Meg called that voice her inner demon. But on nights like tonight, if she was being candid, she knew it was really her inner slut.

'Hmm,' Meg mused as she briefly fantasised she could meet, date and then seduce a transgirl. 'Womanly softness, care and understanding combined with a nice hard dick to fuck me with. Why can't I have that?'

Still undecided about her destination, Meg opened her closet, 'Oh shit!' she thought. 'I was supposed to pick up my new dress from the seamstress on my way home.'

Knowing Denise, her seamstress, often worked late on a Friday, Meg found her phone and dialled Denise's number.

It rang only twice before Denise picked up, "Denise Matthews Alterations, Denise talking. How may I help you?"

"It's Meg, Denise," Meg said. "Don't you ever look at the caller ID?"

"Meg, my dear, I have a mouth full of pins, hands full of dresses and my phone tucked under my chin, so you're lucky I chose to answer. Now, where the hell are you? You were supposed to be an hour ago."

"I forgot, Denise," Meg apologised. "How long will you be there for? Do I have time to get over and pick it up?"

"You can come over anytime in the next three to four hours, darling. But you have to promise me you won't freak out at my clients when you get here."

'Why on earth would I freak out about your customers?' Meg thought. But she dutifully promised she wouldn't and hung up.

Selecting her sexiest matching push-up bra and panty set, Meg then adjusted her bra until her generous breasts were displayed to their best advantage. Next, Meg threw on a pair of sweats before putting on her sexiest pair of strappy stiletto heels. Then, grabbing her purse, credit cards and keys, she headed to Denise's to pick up her newly-altered dress.

Denise was a genius at subtly altering clothes to hug her client's figures. Meg loved how, after Denise had worked her magic, her dresses emphasised her breasts, clung to her narrow waist, and then flared wider to hug her toned ass. The skirt part of every dress clung to Meg's shapely thighs and moved sexily with her swinging hips as she walked. And Meg loved how many men's eyes were drawn to her ass as she strode by. But when these gawping men walked into a light pole staring at her, it was hilarious.

Pulling up at Denise's workshop, Meg slid out of the car, ripped open the unlocked door, and loudly announced her presence.

"In the back, my dear," Denise's voice came.

Striding into Denise's alteration workshop, Meg stumbled to a stop and stared. No less than three men stood or sat in various stages of undress. All the men wore makeup thick and vibrant enough to shame the loudest of Drag Queens in the shows in the drag clubs in New Haven. In addition, these men had heels higher and gaudier than anything Meg had seen worn before. Plus, they had breast forms larger than any breasts she'd kissed or fondled, and wore panties so small their balls should have hung out the side. What they'd done with them, Meg couldn't fathom.

What she did notice was that the prettiest of these femmeboys was studying her as intently as she studied them. Meg especially noticed when his thick and hardening cock popped out from between his thighs and began straining against his panties.

Embarrassed, the poor boy quickly sat on a couch and placed a cushion over his swelling member. But not before Meg overtly stared at his tented panties as she licked her suddenly dry lips.

Denis did the introductions, "Meg, this is Veronica, Vicky and Sissy-Anna. Girls, this is my friend Meg. Now show your best manners and greet her as young women should."

Each of the 'women' took the time to try to strut sexily across to Meg before lifting a heel off the ground behind them and exchanging air kisses.

All gave versions of "Hello, darling. Pleased to meet you." All except Sissy-Anna. Sissy-Anna grabbed Meg's forearms and squeezed maybe a tad too tightly before sultrily singing, "You are my dream girl, Miss Meg."

Sissy-Anna's panty front still obscenely bulged as she pulled a surprised Meg in for a quick kiss. Sissy-Anna's tautly erect penis touched Meg's tummy as she did.

"Enough, Sissy!" Denise snapped. "The poor woman doesn't need to see or feel that. Now go sit down and cover yourself."

Meg wanted to protest that she didn't mind one little bit but thought discretion should hold the day. So, instead, she coughed and quickly stepped back before Sissy could feel the sudden heat in her nether regions and swiftly hardening nipples.

Though Sissy-Anna immediately obeyed Denise's order, Meg felt Sissy give her forearms one last quick squeeze before almost throwing Meg's arms down. Sissy doing this caused Meg's hands to brush across Sissy's throbbing cock, and Meg felt her arousal almost peak.

Once the other girls had retaken their seats, Denise turned her piercing blue eyes on Meg, "What on earth do you have on, Meg? Sweatpants and a top? You dare come into my workshop in that? My goodness, girl, I thought I taught you better than that. Come on, off with them. If you get to ogle the other girls in their lingerie, it's only fair they get to ogle you!"

"Oh, Gawd," Meg thought as she peeled off her top and sweatpants. "Dark red satin panties. I hope my arousal hasn't soaked through them."

It may have been because she'd had her brief fantasy about dating a transgirl before leaving home. But, whatever the reason, Sissy-Anna, and the other two, what were their names again? Had her imagination running wild and her juices flowing. Strutting across to the couch, Meg sat beside Veronica. She'd purposefully kept away from Sissy because she knew Sissy's presence close to her would precipitate her impending orgasm.

Sighing, Denise said, "Meg, it's a little difficult to test the fit of your new dress when you're sitting on a couch. Baby girl, get up on the table and put it on so I can see if it fits as it should."

'Oh, no,' Meg thought. 'My knickers will be at eyesight. If my panties are as wet as I feel, my arousal will be obvious to everyone.'

But, even so, she did as her seamstress requested.

A few moments later, Meg stood two feet in the air, wearing nothing but silk stockings, suspenders, and 5-inch strappy stiletto heels. Her only other nod to modesty was a tiny thong that barely covered her slit, let alone her pubic area. Moreover, the thong covered no part of her sexy ass. Somehow or other, Meg had let Denise talk her out of her bra because Denise thought her new dress would look better without it.

'I should be embarrassed,' Meg thought. 'Why aren't I? And why do I feel so comfortable with these 'gals'?'

Even Sissy-Anna's erect penis poking salaciously against Sissy's panties didn't bother her. In fact, if Meg wasn't careful, her eyes sought out Sissy's panties, and she touched her top lip with her tongue.

The 'girls' discussed Meg's figure blatantly as they sipped wine and openly ogled her. "Tits to die for," Veronica said. "Gawd, I wish I could have her shapely bottom," Vicky added.

"It's the whole package," Sissy-Anna chimed in. "The wide shoulders, generous breasts and hips and tiny waist all make a divine combination. I wish I could develop her hourglass figure. Look," Sissy stood up. "Eight hours a day in my damned corset, and I'm still as square as a damned cardboard box!"

Sissy-Anna's rock-hard penis still throbbed against her panties. Watching it jump, Meg offered a quick prayer to the Gods she believed in that her arousal wouldn't become too obvious. If these 'gals' knew anything about a woman, they would tell from her hard nipples that Meg was aroused. But she hoped she could blame their hardness on a chill or cold breeze. Wet panties were more difficult to explain away.

Denise finished tacking the dress into the folds she thought were needed to enhance Meg's perfect hourglass figure. Then, handing the dress to Meg, she said, "Here. Put this on. Let me see how that looks."

Grateful for the extra modesty, Meg quickly donned the garment.

"Almost," Denise said. "Come down off there for a sec, Meg. I need to adjust the cleavage line."

Getting down, Meg waited patiently as Denise carefully tucked the inner sewn line of Meg's cleavage further under, exposing more of Meg's generous breasts. Unwittingly, the back of Denise's fingers dragged across Meg's inner breast mounds and occasionally across Meg's nipples.

Biting her lip to prevent the sensual moan she felt brewing, Meg tried thinking about anything other than her arousal.

"Up on the table, Meg," Denise demanded.

Once Meg was on the table, Denise walked around with a critical eye on her creation.

"May I offer a suggestion?" Veronica asked.

"Sure," Denise answered.

Standing and walking over to Meg, Veronica cupped Meg's firm, shapely buttocks. Then lightly touching just below Meg's rosebud, Veronica said, "If you cut a little v-slit here, then tack the material at the top of the v tighter together, the dress will cling to and emphasise Meg's gorgeously sexy ass. Plus, as Meg bends over, anybody behind her will almost see nirvana without actually seeing a damned thing."

"Good idea," Denise said as the other two girls crowded around.

Each took their turn cupping Meg's bottom and stretching her dress tighter over her ass. Instead of being offended, as she would have been if any man had done the same, it was all Meg could do not to moan out her arousal and desire.

"Drop the dress, Meg," Denise instructed.

Fearful of what was about to be revealed, Meg reluctantly complied. Fortunately, only Sissy-Anna was in front of her as the dress hit the table. Unfortunately, Sissy openly ogled Meg's breasts as they bounced delectably into sight. But when Meg saw his eyebrow raise as he took in her wet patch stained thong, she thought she might actually die from embarrassment.

Sissy merely grinned as he offered Meg his hands to help her step down. But, as Meg's feet hit the floor, Sissy stood closer, and Meg's warm pussy dragged across his throbbingly erect member.

"Enough, Sissy!" Denise reiterated, "Any more of that rubbish and you can get your clothes on and head home."

But Denise's eyes twinkled, and a smile played around her lips. Even if these woman-blind men didn't, Denise knew that Meg was incredibly turned on. Denise almost seemed to encourage Sissy to flirt more, despite her admonishment.

Sissy-Anna needed no further encouragement. She pulled Meg's hands down as she pulled Meg closer. Then, as Sissy leaned in to give Meg a chaste kiss on her cheek, Sissy guided Meg's hands onto her todger. Sissy only let Meg's hand touch her for a moment before quickly stepping back.

Now, Veronica and Vicky may have been deaf and blind to a woman's arousal, but they knew what a male seducing a willing female looked like. Several gasps were quickly followed by 'women' sitting down swiftly and pulling cushions onto their laps.

Nonplussed, Meg turned to Denise to find her smiling whilst holding a silk robe open, "Here you go, Meg, honey. Hide yourself in this until the girls settle down."

"But I didn't do anything," Meg whispered.

"You being you is enough to raise an erection in the dead, Meg. I've always thought how beautiful your naivety about your sensuality was, but now you're beginning to realise just how hot you are."

Stunned, Meg moved to sit on a sofa chair away from the others. But the girls were having none of that, and Meg was almost dragged across to the couch. Suddenly, she was sitting surrounded by very feminine ladyboys, all sporting large erections.

'Why do I find this arousing and not disgusting?' She wondered. 'If these were men, I'd be slapping faces and storming off, threatening to sue Denise for every penny she has. Wait, they are men, so why aren't I knocking heads together?'

She didn't know, but she thought if just one more hand 'accidentally' brushed her aching nipples, she would orgasm on the spot!

A seeming age of denied orgasms later, Denise finally said, "Up on the table, Meg. One more quick check before I sew everything permanently into place."

Meg gratefully donned her dress again before climbing onto the table. A quick scan and Denise was happy with how everything sat. Five minutes later, Meg did a slow pirouette on the table as the girls all stood to clap.

"Beautiful," Vicky said. "Divine," Veronica added. "Perfect," Sissy-Anna chimed in.

Blushing, Meg thanked the girls before hugging Denise, paying her and leaving before she did what her sexually frustrated body demanded of her. For the last five agonising minutes, Meg's lustful mind, her raging inner slut, flashed images of ripping panties aside and gobbling the knobs revealed.

"It would have been perfect," that no longer little demon wailed. "A cock for each hand and one for your mouth. Then, later, one for all three of your aching holes."

Starting the car, Meg instinctively turned in the opposite direction to downtown, 'I need to find a hot transvestite to fuck tonight,' she thought as she drove for New Haven's queer district. 'And boy, is she going to get a fucking!'

"So why didn't you take what was on offer?" That only slightly smaller demon asked.

'If Denise wasn't there, I would have,' Denise answered defensively.

"Chicken," her inner demon whispered before Meg shut him off.

Trolling through some of the gay bars, Meg searched for what she needed. Plenty of boys and more than a few women hit on her, but she couldn't find what she looked for. Oh, there were many cross-dressed males out that night, but they more resembled truck drivers in a sack than a sexy woman with an added package.

Despairing, Meg took a seat at the bar in 168 York St Café and ordered a house white. Sipping her drink, Meg contemplated what was next, 'I should just go home and get old faithful out,' she groused to herself. 'At least I won't have to bother trying to converse with it.' But her usual stubborn intransigence kicked in, 'No, Gawddammit! I'm getting fucked tonight, no matter what!'

Meg barely noticed the man who slid onto the barstool beside her until, in a smoothly cultured voice, he almost sang, "White wine, please, barkeep. Sauvignon Blanc, if you have it."

The voice, though much deeper than the tinkling in her mind remembered, seemed somehow familiar. 'It's the cadence,' she thought. 'Almost singing. But I've never met this person before, so why does it seem familiar?'

Shifting slightly, Meg ran a surreptitious eye over the newcomer. 'Hmm,' she thought. 'Only a little taller than me, slim, but toned and lithe. Quite effeminate, really, but dressed very masculine. Meg was about to dismiss him from her mind, but her subconscious caught something, and that old familiar tingle started between her thighs.

Turning briefly away, so the guy remained unaware of her study, Meg then turned her head a little to study him again, 'What was it?' She implored her subconscious. 'What did you see?' But, as usual, that little inner observer, having given its prompt, remained silent.

'Okay,' Meg thought. 'Let me see. Manicured hands, but that's not uncommon these days. Long sleeves in summer, hiding tatts, maybe? Shirt buttoned to the chin, with only the very top button undone. Definitely hiding tatts,' she thought. 'Meg didn't really care for tattoos either way. If her partner had them, she didn't mind. Nor did she care if they were clean-skinned.

The man stood and turned before smoothing his trousers over his ass and sitting back down.

'Hmm, nice ass,' Meg thought. 'Narrow hips and an even narrower waist. Narrow hips but an even narrower waist on a male? Not sure I remember that combination before.'

Meg leaned forwards to get the bartender's attention. Ordering another glass of wine, Meg tried to steal a glance at the man's package. She couldn't be sure because there wasn't a massive bulge, but she thought the guy sported a fairly decent wang.