Get your tongue out of my mouth, I’m trying to kiss you goodbye!

Annie walked into the coffee shop several doors down from the bank where David worked. She caught sight of Dave sitting in the corner furthest from the door. He glanced furtively at Annie, and pointed to the latte he’d bought her.

She walked to the table and leaned over him to kiss him. He shifted uneasily away, checking around the room to see if he was being watched by anyone.

“Not here,” he said.

“Hello, Dave,” said Annie, affronted that he’d not greeted her politely.

“I’m sorry,” he replied, embarrassed by his lack of manners.

“Would you rather come to my car,” said Annie with a smirk. She was aware how he disliked public displays of affection, but old habits die hard. She’d always been a little bit of an exhibitionist. And really, who could blame her. Anyone who had spent this much time trying to look good had a right to enjoy being looked at.

“Your car? Good God, no! That’s what got me into this mess!” said Dave.

“Yes,” said Annie a little awkwardly. “I had no idea anyone would see that. I mean, it could happen to anyone, right?”

“It wasn’t just ‘anyone’ that saw us. It was Shannon, my wife’s sister,” said Dave.

Annie sipped her latte, a thin trace of frothy milk lining her top lip above the scarlet lipstick she liked to use. Dave looked at it. A milk moustache. How awkwardly appropriate.

“You can hardly blame me for that, Dave,” said Annie politely. Even in disgrace she embodied poise and dignity. She sat very straight, her shoulders back and her chin held high. She brushed a lock of her chestnut hair from her face, and looked coyly at Dave. Sitting there, in her blue blazer, high necked blouse and pencil skirt she looked the picture of propriety.

“Besides,” she continued, “it didn’t exactly stop you. As I remember it, you were quite absorbed in things as she knocked on the window.”

Dave cringed as he remembered the moment, Annie’s head between his legs and the slow tap, tap, tap on the car window. His sister in law had been with the local police detachment for a little over five years. The torch, the tone of voice. Everything compounded to form an overwhelming swamp of nightmare soup, and he felt himself drowning in it.

“I thought that was you,” his sister in law had said, the reflections of her torch playing over the shiny badge on her uniform. And Annie, looking up in surprise as his convulsions ceased, a drop of semen falling from her lips.

“At least she doesn’t know you’re,” he paused as he awkwardly searched for the words, “you know.”

Annie stared at him. There is a look only a transgendered person can give, and she gave it on high beam.

“You mean, ‘she doesn’t know I’m a trannie’?” said Annie slowly.

“Oh God,” said Dave.  “I don’t mean…”

“It’s ok,” said Annie. It wasn’t as if she hadn’t heard it before.

“No. Really,” protested Dave. “You know I’m not like that. I’m a compassionate person.  I didn’t mean to be like that.” Dave’s words hung there, but his face silently added, ‘Thank god she doesn’t know.’

“What’s the matter Dave?” said Annie. “The thought of you getting nailed by a trans girl’s worse than you doing one of your co-workers?”

“No,” he said squirming inside. “It’s not that.”

“So, it would be better if I had a vagina?” said Annie mockingly. She checked herself. It was easy to be unkind. Too easy.

“Don’t,” said Dave.

“I suppose it’s as good a reason for vaginoplasty as any,” she murmured as she looked across the tables and chairs and noticed a disabled young man was trying to negotiate the door of the café. His wheelchair was getting stuck and blocking people trying to enter the place.

Dave groaned. He didn’t want to hurt Annie’s feelings any more than he had to.

“At least Shannon hasn’t told Debbie,” said Dave.

“No,” replied Annie. “She won’t just yet.”

“What do you mean,” said Dave.

“She’ll make you sweat for a bit first. Maybe she’ll see what she can get out of you first.” Annie paused and then added, “She’s bound to. She’s a cop.”

Annie slid her hand onto Dave’s leg beneath the table and stroked it. She noticed his hand tremble on his coffee cup. She smiled to herself.

“You’re in a real pickle, aren’t you, Dave.”

Annie got up and walked across the room.  She held the heavy door open and the young man in the wheel chair moved through quickly, a flurry of apologies.

She returned to her seat, several of the people in the café looking at her for the first time. She was tall, a little oversized, probably an athlete. An unusual woman.

As she sat down she returned her hand to Dave’s thigh, a little higher up this time. She continued the gentle pressure.

“Please don’t,” said Dave.

“But Davie,” said Annie, “You said something about, what was it now?” The words hung there for a moment, and then she continued, “Oh yes, I remember now.  You’d do anything for a night with – how did you phrase it – ‘someone like me’. Yes, that was it.”

“Annie, please. We have to stop this,” said Dave pulling himself backward in his chair.

“Oh, don’t worry,” said Annie. “We’ll just be a little more discrete.”

Her hand slid between his legs and he glanced nervously around the coffee shop.

“Tomorrow night then?” asked Annie.

“Tomorrow night,” assented Dave.

The End

A jailbird in the hand is worth two in the bush.

“There is no way,” I said to Amanda, my wife’s awful friend.

“Oh, please,” she begged. “Just pretend.  I mean, really, you can pull it off.”

“And I’m not ‘pulling him off’, either!” I protested.

“Look,” she insisted, “all I’m asking is that you hang out with us. I promised!”

“You set him up on a date with some… some… some floozy, and she’s now dropped out. And you’re asking me to step in. And let’s face it, your brother isn’t exactly a catch. This is going to be the first time he’s visited you since he was in jail. That’s not what I think of as a good catch. Besides, I’m married,” I stammered. “You’re a friend of my wife’s. How can you even suggest this!”

Continue reading “A jailbird in the hand is worth two in the bush.”

Kinky Christmas – Mollie Blake.

David — occasionally known as Diana — is preparing for a rather quiet Christmas. The best laid plans…

‘So you’re seriously not going to see your dad this year?’

For a moment David didn’t reply. This would be the first year in a long time not to go home to spend Christmas with his dad. The phone call from the old man, telling him he needn’t bother because of Covid and the Omicron variant, had been a kick in the teeth. All these years, David endured a festive period suppressing his need to be who he really was because he thought his father needed him. Even last year, amid the UK lockdown, David had to steal his way down South to make sure the man wasn’t alone. Now there is no lockdown, yet the words ‘I’m safer without you,’ conveyed his dad’s true feeling—he would rather be alone at Christmas than have his “queer” son spend the holiday with him. The bastard wasn’t even concerned about the safety of his only son. Just his bigoted self!

‘Yes, I’m serious. I’ll have a happy Christmas for a change. I’ve got whisky, gin, mince pies and chocolate.’ He ran his hand over his left breast, the smooth silk of his lilac cami-top teasing him. ‘And I’ll have all the company I need.’

‘You’re kidding, right.’ From Lucy’s lips this was more command than question. ‘My plan’s just been rewritten. I’m coming over.’

David was about to protest but he didn’t get chance to open his mouth.

‘And I want to spend Christmas with Diana, not know-it-all David.’ Her grin bounced down the phone and slapped David on the cheek as only Lucy’s could. ‘Have you got room in your freezer?’

‘Why?’

‘I’m bringing Haagen-dazs – a new duo, Belgian chocolate and vanilla crunch. And you can let Diana know, that will be the only vanilla delight she’ll experience on Christmas day. I’ve got a super-kinky pressie.’

David’s hand moved lower. ‘Ok, see you later.’

It was Christmas Eve and David opened the door to Lucy and her purple mane of thick waves falling over her shoulders.

‘Quick, let me through before this melts and we have to wait for it to go stiff again.’ She fled to David’s kitchen but not before passing her free hand over his crotch and laughing.

From her bag she pulled out the ice cream and popped it straight into the freezer. Then she withdrew a turkey crown big enough to feed them for a week! a bottle of prosecco and another gift bag bulging with gifts wrapped in shiny Christmas paper. She turned to David and beamed.

Now it was his turn. ‘As this is our first Christmas together, I got you a Christmas Eve gift.’

He dipped his hand into his trouser pocket and handed Lucy a small box wrapped in paper decorated with holly and berries.

Shredding the paper with the excitement of a toddler, Lucy discovered exquisite snowflake earrings carved in sterling silver.

‘They’re antique,’ David said.

‘They’re beautiful.’ Lucy proceeded to replace her bling Christmas tree ones with the snowflakes. ‘We’ve got a theme going here.’

David’s curiosity would have to wait until Christmas day.

‘Open this one first.’ It was Christmas morning and Lucy picked the larger present from her gift bag.

They were sitting up in bed, naked after a very “demanding” evening.

David held up a cotton vest top, the fabric imprinted with large snowflakes. In lilac, of course. He slipped it over his head. ‘I need some makeup on,’ he exclaimed after peering at his reflection in the dressing table mirror.

‘Here, you’ll want this.’ Lucy handed over another present.

The wrapping paper ripped off, David rolled up a lipstick to reveal a deep purple colour. It would be a new shade for Diana. He licked his lips with an alluring glint in his eye. ‘Let me see if it suits you.’

He leaned forward and placed his lips over Lucy’s left nipple, leaving a perfect purple “kiss” surrounding her darkened nipple.

With blush and mascara to complete her attire, Diana blew a kiss to her own reflection. ‘I’ll put the turkey in the oven and then you can open your gift.’

‘You knew I had my eye on these in Harvey Nicks!’ Lucy declared, stepping into Jimmy Choo 4 inch stilettos which had been way beyond her budget.

Diana watched with admiration tinged with a touch of jealousy – there was no way David could walk on those. But it didn’t matter. They would have hidden her Christmas-red toenails anyway.

Delving into the gift bag once more, Lucy pulled out parcels containing Terry’s chocolate orange, a bottle of Drambuie and a candle in the shape of a reindeer – soon to come to a fiery end this evening. One box remained. ‘This is to wait until after dinner.’

After preparing the meal to Christmas pop blaring in the background, and eating to Carols from St Paul’s Cathedral, the couple finally retired to the lounge armed with Bollinger and the board game, Risk. Lucy may have been short on stature but she packed a punch and was one tough cookie when it came to world domination, or at least David and Diana’s.

As evening descended and the bedroom beckoned once more, Lucy handed Diana the final gift. Diana fondled the lilac silicone love ring, her fingers tracing the raised snowflakes on the outer ring. She licked her lips and grabbed Lucy’s hand.

‘Wait a sec,’ Lucy yelled, slipping away into the kitchen to return with the erotically delectable Haagen-dazs. The large tub contained far too much for them to eat, but none of it would go to waste.

This was the best Christmas ever.

Wishing Fiona and all her gurls a wonderful, safe and happy Christmas and a New Year free from fear.

Get more Mollie Blake HERE.

The Apartment. A Halloween ghost story for crossdressers.

Going back to places in our past can stir up emotions, don’t you think? Perhaps it’s the same for you. Settle down and enjoy this story, as Jeff returns to his old apartment to find more than a few old cobwebs.

You can find more stories HERE.

🙂

Fiona

  • http://FionaDobson.com

I’m sorry, Gerald’s not home right now.

Ivy showed the Metropolitan police inspector to what she called ‘the drawing room’. It was in fact the living room, but since she and her husband had inherited the place in 1971 they’d always called it that.

“Your husband’s family seemed most concerned,” said the inspector as he sat down in a love seat that had seen better days, and less weary lovers.

“Oh, don’t mind Mildred,” said Ivy, seeing the inspector looking at the sleeping form of a woman in her mid sixties, dozing beneath a brightly colored blanket. A soft snoring sound emanated from the form of the sleeper.

“She has her good days, and she has her bad days,” continued Ivy. “Alzheimer’s. Can you believe she’s barely four years my senior?”

Continue reading “I’m sorry, Gerald’s not home right now.”

The Crossdresser’s Guide To Marital Bliss.

The Crossdresser’s Guide To Marital Bliss is a series of episodes taking a hilarious look at how one crossdresser brought his wife to a place of understanding and acceptance. It’s also instructive and full of good advice to those of us who wish to introduce our dressing to the principal relationship in our life. I hope you enjoy it. Get Part 1 here. Fiona.

Sitting in the garden, just by where Ali had completed a rather unusual example of topiary depicting Cleopatra’s Needle and two of the Elgin Marbles, not to scale, I poured my wife a glass of wine.

“Darling,” I said. “have you ever had a boyfriend who liked to crossdress?”

“Well, I really don’t know,” she replied nonchalantly. “What they get up to in their spare time is a mystery to me.”

Get all episodes here.

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When it comes to feminine hygiene products, I’m your man.

It’s going to be a very long weekend. Before I get into the ‘why’ let me first wish you the happiest of Thanksgiving weekends, if you are in the US, and if not, you know my thoughts are with you anyway.

I would also ask you to share this as widely as you dare, as I am trying to build followers. I appreciate your help. Let me adjust my skirt and tell you what this is all about. Being a crossdressing advertising executive does give me something of a unique perspective on things.

Now, the weekend. It all started when I overheard Joe, at the advertising agency, saying very intensely into his phone, “when it comes to feminine hygiene products, I’m your man!”

Continue reading “When it comes to feminine hygiene products, I’m your man.”

Exposed At The Summer Party.

“I told you before,” said Samantha, “You’re going to wear this lovely hoodie I just got from Amazon. Look, it’s the perfect size!”

“But I don’t want to wear it,” replied Darren.

“Yes, you do,” retorted his wife, as she looked for a summer dress in the bedroom closet. A nice pink one might be just the ticket.

“It’s a company function, I can’t possibly wear that!” he said in frustration.

Samantha adopted her most patient demeanor, and repeated, “You’re going to wear it. Think of it like this, you can pretend to be the wife. You’ll like that.”

With that she slipped her jeans off, and started to go through some of the summer dresses in her wardrobe. The heat of the summer was dissipating, but she could still get away with something revealing her perfectly tanned shoulders. She also like the soft materials, and gentle colors.

Trying a slightly different tack she added, “Besides, look how well these colors go with my dress?”

“Darling, it makes me look soft. It’s not manly,” said Darren. “Everyone is going to be wearing the tee shirts with pictures of cars, or motorcycles. Did you see that thing Steve wore last year? It had the picture of an F22 jet on it. He said something about it being ‘power dressing’.”

“No self-respecting teenager would wear that, as you well know,” responded his wife. “Think of it as just being your true self. Gurly dressing. After all, that’s what you like, isn’t it? Besides, they’ll just assume you’re striking a blow for trans rights.”

“I don’t want to blow anything,” said Darren, an air of dejection in his voice. He knew there was little point arguing with his wife when she had set her mind to something.

Samantha sat on the bed thinking about which summer dress would be best, her full breasts gently rising and falling with her breath. The summer afternoon light caught her beautiful honey colored hair just perfectly and her beauty almost made Darren catch his breath.

At length she said, “That’s not what you said last night.”

Darren shuddered. He hated it when she brought up things like this outside of their sexual activities.

“Don’t say that, darling,” he muttered awkwardly.

“Oh, come on. Own it, Darren. You told me you wanted to suck cock, and at the time you were wearing the panties I’d bought you. Do I really have to remind you?”

“That was different.,” he replied feeling embarrassed.

“Oh? And you seemed quite happy to wear my robe, and those heels,” said Samantha. “No, missy, you’ll wear what you’re told to wear. Besides, you practically begged me for anal last night.  I’m likely to be more forthcoming if you do me the favor of wearing something appropriate. Who knows, perhaps tonight is your lucky night.”

“You’re going to make me wear this… this… flaming gay hoodie to a company function?” protested Darren.

“Yes, darling,” said Samantha, pulling on a summer dress that complimented the hoodie. “If you want me to accept your dressing up then I expect you to dress in a nice way.  Besides I picked this one out specially. I think it’s very feminine, without being too obvious.”

“Look at those colors! It makes me look like I am some sort of dick hungry whore!” said Darren.

“But darling, when you were inside me last night, and I told you to say ‘I need to suck dick!’ that’s precisely what you were. I only want you to dress the part.  Is that really so bad?”

Samantha would not be moved, and eventually Darren did pull on the hoodie. It was just the company picnic, after all. No one would be wearing work clothes. All the same, he felt he was taking a terrible risk.

“There you are!” said Samantha. “Now, if you are really good I may let you be naughty tonight. I’ll even call you Darlene while I take you.”

Darren smiled. He knew that every cloud had a silver lining. And he really liked the hoodie.

As he walked to the car he forced his ass out a little, and swayed his hips. Yes, he had the best wife ever!

Jensen And The Lady Of The Manor – Part 5.

Jensen and Mrs. Sinclair are getting in deep.

Get all the Jensen episodes HERE.

Jensen And The Lady Of The Manor – Part 2.

The second part of this series finds Jensen slipping deeper into Mrs Sinclair’s intrigue. Jensen’s unusual punishment becomes evident. Ms. Katia Thornwood’s list is available in it’s entirety here: https://www.patreon.com/posts/ten-tasks-for-of-37281389

You can find the first episode here – https://fionadobson.com/jensen-and-the-lady-of-the-manor/

You can find all the Jensen episodes HERE.

The Travelogue Of Katia Thornwood – Part 1

All work and no play does make a person dull. And in my work, I need to always have an edge, or many, preferably sharp, pointed or at the very least, hard.

So I’m travelling to South East Asia for research, and of course a little respite. First stop, Cambodia, a little resort just outside of Seam Reap. Then Thailand – that heady mix of dirt, excitement, and mystery that I’ve always found so intoxicating a prospect.

Siem Reap is a harsh Mistress in herself. The heat is hard to explain, inescapable, it invades every pore and the only way to survive it is to surrender to it. My dewy skin breathes in temporary relief as the tuk tuk turns and the mildest hint of a breeze ripples through my cotton shirt, over my bare décolletage, sensually brushing bare skin and bringing me to life in a way I haven’t felt in a long while.

The road is an ordered chaos of interweaving tuk tuks, mopeds and cattle. The smell is a heady mix of boiling refuse and floral fragrance from the vegetation of the fields and forests beyond.

I contemplate being a stranger in a foreign land must be somewhat similar to how my submissives feel at times. At the mercy of many things that are beyond their control, trusting that things will work out because they have to, yet knowing around every turn is something that may just push them completely out of their comfort zone, at best, or completely destroy them, at worse.

Continue reading “”

Clothes Maketh The Man – Part 51 is out!

I sat in the ships dark store room space with my head in my hands. The dull throb of the engine filled the air and became the background music of the dark drama playing out before me. Here I was, shunned by Devina, on a cargo vessel moving through the dark night, on a black river headed who knows where.

Read Part 51.

Go to Clothes Maketh The Man Chapter list.

I guess he didn’t know what sort of gurl I am.

I cut across the square and walked into the bar after work. I usually only come here at lunchtimes, the fish always being fresh and the salad light. I can come in here, have a quick lunch and be back at my desk within an hour easily.

In the evenings there’s a lot of people in from out of town, there being a large hotel next door. And there’s a fair crop of locals too. It’s quite busy after six. It’s surprising how crowded this lonely city can be when all the commuters go home.

I don’t think I’d seen this one before. Maybe I had but it didn’t matter anyway. It’s not like I go out looking for romance. But he looked interesting. He told me a name, and I just let him freestyle his way into my evening.

He bought me a few drinks, and started to get a little touchy feely. Well, it was ok. The bar was closing soon anyway.

I decided I’d walk home with him, his place wasn’t far from mine, and we’d part and he’d never know how different I am.

But that’s not quite how it went down. Sometimes it doesn’t. Sometimes it just gets more interesting.

We decided stopping at my place for a nightcap might be ok.  Why not? He leaned close as I fumbled for my keys, his breath heavy against my cheek. By the time I found my keys he was running his hands inside my jacket searching for my breasts

Continue reading “I guess he didn’t know what sort of gurl I am.”