And so, it was decided. I was to go on a search and rescue mission to find Fiona's son Ritchie, and bring him home to Mummy.

Ritchie was all of 36 years old. He became a father whilst still in his teens. Married and divorced the mother before he was 22. More recently, he'd been living with his pregnant fiancée for the last couple of years. His choice of partner always struck me as strange, in that every one of the ones that I'd met was clinically obese.

Ritchie looked a lot like his dad Bob did at the same age. Not so well sculpted physically, but facially almost identical. The last time I'd seen him was at his engagement party, eighteen months ago.

Oh! And another piece of info that might interest the reader. On Ritchie's 18th birthday, there was a small house celebration to which Linda and I had been invited. I worked away from home in those days, so I couldn't go, ergo, Linda went on her own. She told me later that during the party she needed to wee. The downstairs toilet was engaged, and she had to use the bathroom upstairs. On exiting, she met Ritchie at the bathroom threshold.

Now, ever since Ritchie was a young teenager, it was obvious that he had a crush on his mum's chum.

(As you do! Coincidentally, I fucked my mum's chum on my 18th birthday. Anywaaaay...)

After a few seconds of awkwardness, Linda pointed out to the Birthday boy how disappointed she was that she hadn't given him a birthday kiss. She then grabbed his arms and pulled him into the bathroom. She closed and locked the door before giving him the biggest and best kiss he'd ever had... including tongues. Her story, as she had told me, was that after a proper long kiss, she left the young fella to do whatever it was he came to the bathroom to do. I remember saying to her, "Yeh a wank about his aunty Linda!"

Meanwhile, back in Fiona's boudoir...

"OK. I'd better give myself a quick tidy up." I picked up my pants and shoes, grabbed my bag, and hurried through to Fiona's en-suite.

"Thanks, babe." Fiona's appreciation was genuine. She held her phone to her ear, waiting for her call to be answered.

I could hear her muffled conversation from behind the bathroom door. The bathroom mirror revealed that my lips and hair needed some attention. I noticed a small compact by the sink, opened it, and dusted the translucent powder over my face and neck. I pulled up my bra straps, buttoned up my blouse, and straightened my stockings before slipping into my shoes. One more look in the mirror and I was good to go.

I walked back into the bedroom. Fiona was texting on her phone. "I've sent you a message with Ritchie's whereabouts and his number."

My phone indicated an incoming message as if to confirm Fiona's info. "OK then. I'll be off. I'll give you a call once I find him."

I exited the bedroom to more of Fiona's gratitude. I heard Mathew shout, "Good luck! as I descended the stairs. "Your coat's hanging in the cloakroom cupboard."

I fed Fiona's info into the car's sat-nav before reversing back into the street. According to the small display, it would take fifteen minutes to reach my destination. 'Sade's Greatest Hits' was the soundtrack during my short journey.

The drive itself was uneventful. I relish the dark afternoons at this time of year, when the headlights of oncoming traffic light up your face in the rear-view mirror. Naturally, I had the sun visor down, allowing the appropriately named vanity mirror to do exactly what its name suggests.

"In 100 yards, you have reached your destination on the right." The voice on my Sat-Nav is set to male. I'm not confident with a female giving me directions. (insert smiley emoji)

I turned into the busy hotel car park. I could see no sign of Ritchie as I carefully navigated the rows of parked cars. My circuit took me past the hotel entrance. I crawled past and glanced inside, on the off chance that Ritchie might still be on the premises.

I spotted a vacant space at the edge of the car park, accelerated towards it, and reversed into the bay so I could observe the area from inside my vehicle. I had no sooner switched off the engine when I caught sight of a young man who was clearly intoxicated, sitting on a bench, in the hotel's garden. He was drinking what appeared to be a tin of lager.

"There's ma boy!" I picked up my phone to call him.

"The number you have dialled is unavailable." I keyed his number again, only to receive the same automated message.

Getting out of the car and shouting across the car park was not an option. I looked for a free space closer to my target. There wasn't one.

"Fuck! I'm going to have to go and get him." I placed my phone back inside my bag and rummaged for my lippy and lip gloss. I switched on the vanity mirror light and slowly traced another layer of lipstick over my lips before sealing it with the lip gloss.
"Yeh! You'll do." I afforded myself a cheeky wee smile, picked up my bag and exited the vehicle. I was able to pull up my stockings discreetly before setting off in Ritchie's direction. My walk brought me to the entrance of the car park, where I paused to let a couple of cars pass. A third came to a stop. The driver, a man who looked to be in his late forties, flashed me a broad smile and gestured for me to cross. I acknowledged his courtesy with a raised hand and a smile of my own. We held each other's gaze as I strolled casually in front of his car, allowing my open coat to reveal both of my best features.

I skipped up onto the pavement and looked back over my shoulder. "Oh, if you only knew!" I thought to myself, as another macho guy had succumbed to my wily guise. Buoyed by a surge of confidence, I continued my sashay onto a footpath that cut through the well-kempt lawn.

Ritchie raised his bowed head to slurp another mouthful of lager. He could see a woman approaching through the late afternoon darkness. As I closed the distance between us, he ogled my slow strut. By the time I reached him, I had his full attention.

"May I?" I didn't wait for an answer and sat down beside him on the bench.

Ritchie looked puzzled as he scrutinised the stranger sitting cross-legged beside him. I could almost hear the rusty cogs in his head grinding into motion. We were only a foot apart, yet it appeared that he had no idea who I was.

"Alright?" He was a man of few words, but it was a start.

"Yes. You?" My voice was soft and clear.

"Do you come here often?" His smile was so like his dad’s. I couldn't help but smile at his cheeky sense of humour.

"You have a lovely smile." Wow! My best friend's son, more than thirty years my junior, was flirting with me.

"Thanks." I held out my hand. "I'm Michelle." Our hands met in a gentle, delicate handshake.

It was obvious up to this point that Ritchie hadn't 'made' me. The Cougar in me was tempted to seduce him, but I couldn't bring myself to take advantage of his vulnerability.

“Your mum sent me,” I said quietly, revealing only what was necessary.

"Oh! OK." He sounded surprised. "So you're Mum's friend?"

I gave a confirming nod.

A look of sudden realisation crossed his face. "I... eh... em... Oh fuck!" He was having difficulty finding the words.

"What is it?"

"Em... I've seen photos of you in Mum's Facebook." He paused briefly. "Oh, my God!"

"Oh my God, indeed," I thought to myself. I had to know if he'd seen any of me posing with cock in hand.

"Oh! Really!" I knew he'd seen some of the many that I had sent to his mum. But which ones? There were only a couple of me holding my man-clit! So I asked. "Which ones?"

Our conversation was interrupted by a few spots of rain.

"C'mon. You can tell me in the car." I stood up, straightened my skirt, and buttoned my coat.

I took his arm as we walked the short distance to my vehicle. We looked like any other couple to the unsuspecting people milling about in the car park. Or at least we would have, if not for the fact that I was in my sixties and he was in his thirties.

We hurried on as the rain came down harder, attracting a few curious glances from those making their way to the wedding celebration from which Ritchie had been ejected.

There was little conversation as we fast-walked our way to the car. I pulled the key fob from my coat pocket and pressed the unlock button. The indicators flashed, and the car gave a sharp bleep, drawing Ritchie's attention to the black BMW stationed in a quiet corner of the car park.

"Nice car!"

A few seconds later, we were sitting inside the 'nice car'. And like a dog with a bone, I wasted no time in resuming our conversation where we had left off.

"So which ones?" I forced an innocent smile.

"What?" He knew fine well, 'What'. He was reluctant to tell.

I responded with a tilt of the head and a tight-lipped smirk. "Which photos?"

I was implementing the 'silent close'. (IYKYK) waiting for a reply to my gentle interrogation.

Ritchie remained mute. There was a look of embarrassment on his face, and after a couple of seconds of awkward silence, he put his hand in his pocket and pulled out his phone.

"Oh fuck! Four missed calls from Mother. And five messages." He pressed the 'Gallery' icon on his screen and scrolled through some photos.

"Ahha! That's why I didn't recognise you!"

"What? Why?" I couldn't see the photo that he was scrutinising.

"Your hair's different!" He paused before turning his phone around, allowing me to view the photo. "And you have a cock!"

"!!!" I was speechless. There I was. Adorned in Linda's navy blue polka-dot frock. I was wearing my long-haired auburn wig, sitting on our bed and smiling, whilst holding my stiff cock.

The tables had turned. I was now the vulnerable one. I took the phone from Ritchie's hand and gazed down at my photograph.

"Oh! That one." I looked up to see a grin that spread across his face. An awkward lull settled over the car once again.
After a short interlude, I broke the silence.

"How come I'm in YOUR phone?" The best form of defence...

"I copied it from Mum's laptop." His reply was unashamed. After all, he wasn't the one wearing the frock.

"Why?" My curiosity knew no bounds.

"Because... It turned me on." Even in the dim light inside the car, I could see the colour rise in Ritchie's cheeks.

"Oh!" I returned the phone and leaned over the handbrake to kiss him. He met me halfway. The sexual tension inside the vehicle was palpable. Our lips collided and our tongues intertwined. I casually pressed the recline button, easing the seat back until it was halfway reclined.

I placed my hand on his groin, slowly encouraging the beginnings of his semi. I continued to rub and squeeze the lump that was manifesting under his suit trousers, while continuing to exchange oral drool.

A quick look around the vicinity confirmed we were quite alone. The rain had cleared the car park of any nosy observers who may have been lurking in the shadows.

I unbuckled his belt and pulled down his zip to reveal his underpants. Ritchie lifted his backside to assist me in slipping his trousers and pants from under his ass. His cock sprang up, exposed and granting me the first look of his manhood.

My first thought was "Wow!" It resembled a cock... only smaller. Once I got over the surprise of someone having a dick smaller than mine, my second thought was, "I could take that..." Every cloud!

I took a firm grip and began wanking him, slowly at first. His breathing became erratic and audible. He began groaning in my ear as I quickened my stroke.

"Fuck! Oh fuck!".

"Tell me when you're going to cum." I whispered in his ear. He nodded his assent.

I could tell by his feral outbursts that an orgasm was imminent,

"Ohhh fuck! I... I..."

I positioned my head over his purple button mushroom, ready to swoop. There was no room for my hand and my mouth to work together, so I cupped and caressed his balls and wrapped my mouth around his cock.

And not a moment too soon! A stream of cum skimmed over the surface of my tongue. I closed my mouth around his cock, sealing any of his spunk from spilling out, and began to bob my head for all I was worth.

"Fuuuuck!" As Ritchie kept spurting, I kept swallowing.

"Mmmmm" Was all I could contribute to the lustful dialogue. "Mmmmmm."

Ritchie's torso contorted and jerked. His verbal contribution consisted of inaudible grunts and expletives.

The whole encounter lasted about a minute. Not only was he cursed with a small cock, it appeared that he was also a premature ejaculator!

He sat back in his seat, panting heavily. "Woooh hooo!" He released a high-pitched howl.

I sat back up in my seat, licking my lips, delighted with my mouth-work. After a few seconds, I composed myself and adjusted the rear-view mirror to check the state of my lips. Nothing a fresh coat of lippy couldn't put right. I rummaged inside my bag to find my lipstick.

My reflection looked pleased with herself. Nay! Smug even. Sucked off father and son, and fucked and sucked by Mum.

I finished my lips with a layer of gloss and gave my hair a quick finger flick. I hadn't been 'down' long enough to displace my wig.

I turned to look at my unconventional date. "You alright?"

"Fuck yeh! That was hot!" He appeared pleased with himself. Nay, smug.

I sensed a smugness in his expression. "What is it?" My head assumed an inquisitive tilt. "What are you thinking?"

"I was just thinking... That's now two of my Mum's pals that have sucked me off."

Surely not. Not an 18th birthday present bonus from my Linda. According to her, it was just a heavy kiss. Before I had a chance to dig deeper, my phone signalled an incoming call.

"Yeah, I've got him... Yes, five minutes ago... Yes, he's fine... I know... I know... What about our... our eh friend?" I assumed Ritchie had no knowledge of his mother's Saturday companion. I was looking at my passenger, still sitting back with his pants and trousers at his knees. His breathing had calmed down to almost normal. "Say hi to your mum." I pointed the phone in his direction.

"Hi Mum." He held his cock between his thumb and two fingers and wobbled his floppy semi in the air.

"OK honey, see you soon." I made double sure that Fiona had ended the call before slapping Ritchie's shoulder. "It's just as well that wasn't a video call!" We both imagined the scenario and laughed. "You had better sort yourself," alluding to his half-discarded clothing.

A certain Tina Turner song entered my head, prompting me to start the engine to clear the windows. Ritchie returned his seat to a more dignified position, but made no attempt to pull his pants and trousers up! I made no comment.

While waiting for the windows to clear, I continued our conversation prior to Fiona's call. "Oh yeh!" You were telling me about another of your mum's chums." My delivery was matter-of-fact.

"Oh yeah! So I was." I couldn't believe it. He began stroking himself.

Another of my sexual scourges is post-climax syndrome, and I was impressed that Ritchie was able to reassume his hard-on so soon after cumming. I'm more of a 'Thank you and Goodnight' kinda guy.

"Does speaking to your mum always have that effect on you?" I know it did me! I thought to myself.

"No, but her friends do." He took hold of my hand and placed it on his dick. For a guy with a smaller-than-average appendage, he wasn't at all shy. I took a gentle grip and slowly, slowly, slid his foreskin back and forth.

"Well?" ... Who was she?"
All through our encounter, I was surprised Ritchie hadn't made me. Sure, he now knew I was a bloke in a skirt, but didn't recognise me as the guy who used to babysit him and his three sisters.

"It was a long time ago. On my 18th birthday." Ritchie had my undivided attention. I sat in silence, slowly wanking him off.

"Her name was Linda." He looked down at my hand as it worked on his stiff cock. "Do you know her?"

"No, I don't think so." The little minx gave the Birthday boy a BJ.

"She's still hot!" He looked straight at me.

"Did you fuck her?" I could feel my own cock stiffening at the thought, causing some discomfort inside my tight Lycra pants.

"Yes."

That did it. I pulled my hand from his cock and put the car into gear.

"What's wrong? What did I say?" He sounded upset.

"No. Nothing! Buckle up. We'll continue this somewhere quieter." I drove the car back onto the street and headed for a place I knew would be ideal for what I had in mind. "So... What happened?"

As I drove, Ritchie filled me in with a detailed account of his sexual encounter with my wife.

She was leaving the upstairs bathroom when, on opening the door, she was confronted at the threshold by Ritchie.

"What was she wearing?" (It's a tranny thing.)

"I can remember. She had on a black mini-dress, and she was tanned. She looked amazing!"

I recalled that it was just after we had returned from holiday. Linda would have been in her early forties. I also remember the dress. I've worn it countless times.

Ritchie was in full flow, delighted to be sharing his experience.

"I was thrilled to see her. She said, 'Hey! Birthday-boy!' and pulled me into the bathroom. She closed and snibbed the door, pushed me against the wall and told me... 'I've not given you your Birthday kiss."

The following account is paraphrased and is based on Ritchie's detailed and vivid memory of the events.

The young Ritchie was gobsmacked. Unable to put a sentence together. The next thing he knew, his 'Aunty' Linda had a grip around his neck. She drew his head towards hers. Her open lips met his as they locked mouths. Linda's tongue teased its way inside Ritchie's mouth. He had never experienced a French kiss, and it blew his mind. He'd jerked off countless times and fantasised about this very scenario. She pulled his trousers' zip down and fondled his cock. He was already brick-hard. She then proceeded to pull his cock from under his pants before dropping to her knees and sucking him off.

His first blow-job. He came almost immediately. "There was no surprise there!" I thought, given our recent occurrence.

I was approaching the spot where I used to dress in my early days, when I was with my first wife, when it wasn't convenient to be 'Michelle' at home. I drove between two stone pillars onto a dirt track that led to an old ruin. Ritchie had remained hard, still stroking himself when I pulled up halfway along the track. I switched off the lights, unbuckled my seat belt, and lifted my ass to remove my pants.

"Tilt your seat back." Ritchie unbuckled himself before following my instruction.

I pulled the lever that adjusts the seat to allow more legroom, and put my hand on his free-standing hard-on.

"When did you fuck her?" I whispered into his ear.

"Just after she blew me."

I felt his cock jerk as he reminisced about the incident. "OK. Hold that thought."

The rain was still heavy as I got out of the car. I removed my coat and threw it into the back seat.

"What the fuck!" Ritchie was perplexed. He watched me run in little girly steps around the front of the car to his side of the vehicle.

I opened the passenger door and climbed in on top of him. We kissed in a frenzy, I felt his cock rub against my bare thigh.

From the moment I saw the length and girth of Ritchie's pecker, I knew he was the perfect one to take my virginity. His dad always told me that he'd love to fuck me... but I always declined. I always considered Bob's cock to be big... until I saw the specimen on his wife's fuck-buddy.

"So, then, what happened?" My interrogation continued.

"We kissed for a couple of minutes. I could taste my spunk on her tongue... And then I was hard again."

I know my wife doesn't like seeing a hard-on go to waste, no matter what size, so I kinda guessed what was coming next.
(pun intended)

She walked over to the sink and checked herself in the mirror. Over her shoulder, she could see Ritchie still standing where she left him, holding his cock. She beckoned him over.

At this point, I got up from my position where I was facing Ritchie. I turned around and lifted my skirt, giving him a front-row seat to view my ass.

"Fuck me, Ritchie." Words I never dreamt I'd say in the real world. "Fuck me... Like you did Linda."

I tried to summon up some saliva to spit on my hand, to give my hole some lubrication. But I had a mouth like Mother Theresa's chuff.

"Wet your fingers and finger me."

Ritchie obeyed my commands, to my enormous delight! "Oh fuck! Yes! Deeper!"

He had two fingers sliding inside me when I positioned my ass over his cock. Ritchie took a grip of my hips to guide me down, until I felt the tip of his cock touch my asshole.

My beating heart was palpable. I could see the newspaper headline. "Pillar of Society Dies Of Heart Attack While Dressed As A Woman, Fucking His Best Friend's Son."

I slowly lowered myself to the point where Ritchie's cock pressed against my entrance. I was euphoric as I felt his cock slide inside me. I tried to speak. "What... happened next?" My breathing was sporadic. "What did... you do?" I gasped as I lowered further and took another inch of his shaft.

"She lifted her dress. I could see she wasn't wearing pants. It was the hottest thing I'd ever seen. I walked over to her, and she bent over the sink."

While Ritchie talked, I took more of him inside my man-cunt. He passed the point where his Dad's long fingers had boldly gone, and I knew his cock wasn't much bigger than that.

Ritchie was in full spate. "She opened her legs and told me to fuck her. She was soaking wet, and it slid up easily."

I felt a sharp pain briefly. It quickly became a dull pain until there was very little pain to contend with. I slowly rose until I felt his cock close to popping out and gently lowered myself again. I repeated this action until it felt 'pleasurable' with his cock inside me. "What did she say to you?"

"She kept saying fuck me."

I started to jerk up and down his short shaft with relative ease. He was bucking in rhythm.

"She said, 'Fuck my cunt' a couple of times. I remember that vividly." Ritchie's jerks were becoming stronger. I felt him in deeper than before. My adrenaline extinguished any discomfort. I put my hand under my skirt and began to jerk off. There were no signs of erectile dysfunction. My man-clit was solid.

"Fuck me, Ritchie! Fuck my cunt." I used Linda's words. "You fucker! Fuck me!" and some words of my own.

Ritchie grunted with every inward stroke. "Oh! Ohhhhh Fuuuck!"

"Not yet, Ritchie. Don't you dare come yet." I bounced on his cock and wanked myself hard.

"Fuck! Fuck!" I was about to cum. "I going to cum." I thought I'd let Ritchie know. "Fuuuuck my cunt, Ritchie!" I shot my spunk all over the windscreen. I could hear Ritchie behind me as I felt his pubic hair tickle my ass. I had taken his full length.

"Me too. Fuck! Fuck! I'm cumming!" Ritchie's thrusts became more powerful. He growled like a feral beast as he shot his load inside me. "Fuck Michelle! Oh fuu...Oh fuuuuck!" That was the first time he used my name. "Fuuuuuuuuuck!"

My first fuck.

I sat in his lap, with his cock still fully inside me. My legs felt like jelly, not surprisingly, considering my age. My thighs felt like I'd run a marathon. "Fuck Ritchie. That was amazing." What was also amazing was that there was no sign of any post-climax remorse that I had always experienced immediately following my orgasm.

Ritchie lay back in his seat. He eventually managed a few words. "Yeah! Fuck... it was." And gave a slight moan when I lifted my ass to liberate his spent cock. "So does this mean I'm gay?"

Funny that! His Dad asked me the same question after he'd emptied his balls down my throat. I gave Ritchie a similar reply while reaching for my pants.

"What were your thoughts when you first saw me?"

Ritchie was recollecting his thoughts as I clambered unladylike over the centre console.

"Honestly! When I saw you walking up the path, I thought, Wow!"

"Becaaauuuse?" I encouraged him to expand.

"I thought, that's someone I'd fuck! When you sat down beside me... I thought that you might be... a hooker."

A biological woman would have slapped him. Me? I took it as a compliment. All the same, I would have preferred a High Class Escort.

"OK. So you thought, you'd like to fuck HER?" It was rhetorical. "Well, you just did."

After a little trouble getting the tight Lycra over my shoes and a bit of tucking, my pants were back in place.

Ritchie returned his seat back to its normal position. "You're fucking amazing."

I responded with a coy smile. "Better get you back to Mummy." I started the engine. "Can you imagine what she would say if she knew about this?"

"Oh, fuck." He grinned widely.

We were still laughing as I drove back to the main road. My thoughts drifted to my cock-loving wife, Linda. And what she had got up to on her day/night out. Fiona was in no doubt. She was fucking the guy who picked her up.

It occurred to me that Ritchie hadn't quite finished his story. "So, what happened with Linda? I assume you came."

"Fuck! Yeah!"

"Did she?" I like to know these details.

"Yeah, she came at the same time as me. I saw her in the mirror."

Wow! It was my turn to be gobsmacked. We've both been fucked by the same guy decades apart.

"Did you ever meet again?"

"No. Not like that. I've seen her at Mum's a few times over the years. Still wank thinking about her." Ritchie sniggered at his confession.

I couldn't blame him for having a crush on Linda. She has that effect on most of the guys that she flutters her eyelashes at.

The conversation got round to Ritchie and his fiancée, Dianne. I asked him about his break-up.

Apparently, she found explicit photos on his phone from a middle-aged woman that he met online. I surmised that this boy has a thing for middle-aged women.

As we approached Fiona's house, Ritchie asked if he could see me again.

"Emmm... possibly." His request caught me unawares. "I'll contact you."

Fiona saw us turn into her street. She waved from her lounge window.

"Oh God!" I had a sudden attack of guilt.

"Yeah. I know." Ritchie heard my short outburst.

When I pulled up at her door, Fiona was already standing at the threshold.

She mouthed, "You coming in?"

I shook my head and tapped my wrist, alluding to a watch that I wasn't wearing.

Ritchie got out of the car, turned and popped his head back in. "Thanks."

I smiled in response. "Remember, babe."

"What?"

"Mum's the word." I couldn't resist it. We both had the chuckle it deserved.

Fiona waved me off and mouthed, "Thanks."

As I set off for home, my head was doing cartwheels. I thought it insane what I'd done. I'd seen the biggest AND the smallest cock, both on the same day. And I was yet to hear all about Linda's day...

And that's worthy of a story in itself.