FabSwingers.com > Forums > Stories and Fantasies > Introduction to crossdressing

Introduction to crossdressing

By (user no longer on site) OP over a year ago

This story goes back to pre-internet days.

I fit young carpenter, tall dark and good looking I worked away from home, as it was a good way to get girls, having your own hotel room.

I was sent to a remote Scottish research centre to build some offices, miles from nowhere!

Usually two of us, I was on my own, as my mate was expecting a kid, as it was so remote, we were expected to stay until finished.

After unloading and setting up site, I asked the lady in charge where the hotel was?

Sorry love, no hotels here, we’ve arranged for you to stay with Mark, the manager here, as he’s single and had the space, what’s more, one small pub and one chippy!

Finishing up I went and found mark, a tall slim man in his forties, bald on top with a boarder of hair, looing like they all did in the 50’s

Mark didn’t seem to keen on having me to stay, and the feeling was mutual.

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

We went back to his house, a large, detached house next to the church, and very secluded.

I was shown to my room, and the bathroom, opting to jump in the shower right after unpacking.

As I got out of the shower, no large towels, so I looked in the laundry basket, and saw some sexy black undies, seamed stockings, hey, looks like Mark has some old boiler coming around I thought.

Reply privately (closed, thread got too big)

By *ang999Man over a year ago

oldham

Mmm more please

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Thank you x

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Monday and Tuesday I avoided Mark by working late and going to the pub, but the pub was deadly quiet, Wednesday Mark told me he was going away for the day for a meeting and may not be home.

Back at the house, I went for the Escort and fiesta magazine for a nice wank, noticing that Mark had been seen them, and not put them back the same.

After a good read and wank, I walking around in my boxers and t shirt, I sill felt like more, “he must have some porn here” I thought, and started to search the downstairs.

“Jackpot, hidden in a serial box at the back of a cupboard two VHS tapes, “HPF Films Amsterdam” on the label, New Secretary was one, Teachers Pet the other, Mark you sly old dog.

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Mmm shaping up nicely.. more please!

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

"Mmm shaping up nicely.. more please!"

can't resist a man who says Please! x

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

New Secretary it is, as I always liked the secretary look (and still do)

I went the tape, which was always at the point where the last person left it, bent over an office desk, skirt pulled up, black stockings and high heels, some lovely young girl was getting well and truly fucked from behind by some bloke with his suit trousers around his ankles. My cock sprang to life, and I had soon come as some other gut joined the fun and presented his cock to her mouth.

When I cleaned up I rewound the tape and started from the beginning, Oh my, what the fuck, it started with some bloke dressing up in stockings and suspenders!

My mind raced, I’d never seen TV porn before, and despite slipping into my mums corset style knickers for a wank as a young teenager, I wasn’t sure as this was GAY, and I’m not gay.

But as the wig went on I realised this was the girl I was wanking over before, and with a bulge appearing in my boxers, I watched on. More and more into this I had my cock out and enjoying a slow wank, trying not to come, and not hearing the car pull up the drive!

Reply privately (closed, thread got too big)

By *ay and K888Man over a year ago

Manchester

Naughty

Reply privately (closed, thread got too big)

By *lljambarMan over a year ago

Manchester

Great story so far would love to hear more x

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Wanking away to the film, I didn’t here Mark walk in, he stood there for a minute, and said “what the hell’s going on”

I jumped up, my cock standing to attention, there wasn’t much I could say, except sorry mate, just enjoying your film, both of us feeling very silly.

Mark raced to the Video player, and stopped the film, red with rage or embarrassment he said “no one can find out about this, this could ruin me”

I said calm down, nothing to get upset about, just two single men who like porn, like you looking at my wank mags.

Mark was looking away, I poured two stiff drinks and handed him one, “I was very young, I knew this would come back and haunt me” he said

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

More please. Shaping up nicely.

Reply privately (closed, thread got too big)

By *urabriteMan over a year ago

stafford

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

As I d*unk my drink, I thought he was taking this badly, I wasn’t about to talk behind his back, I didn’t want anyone to know I had been wanking to TV porn, the first penny dropped, I said “the stockings in the laundry basket, their yours?” he looked at me like I had missed the point. “I work for the government, if they found out I did this…”

Then the second penny dropped, fuck fuck fuck fuck! That beautiful girl I had wanked my self silly watching was Mark in an earlier life,

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

This is good, and we haven't even got to the naughty bit yet

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

"Naughty"

Ohhhh Yes

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Oh My god! That’s you… You’re beautiful…as a girl I mean

Mark looked at me as if to say finally, you have caught up

“This will ruin me” he repated, It’s OK, your secret is safe with me.

“like some Sword of Damocles hanging over me, I could never trust you”

My mind raced, she was gorgeous, to the point my cock twinged just thinking about her.

I poured two more drinks, I’ll do something to show you can trust me “like What?”

Err, a picture, I’ll put on a pair of panties and you could take a picture, so I’ll never talk.

“You’d do this? Have you done this before?” Just my mums I said, and my girlfriends once.

“Ok, but not just knickers” he said, stockings and heels too, so there is no getting out of it”

My cock swelling, I said, yes, ok, but now while the drink has taken effect, and I’m not dressing alone!

Reply privately (closed, thread got too big)

By *ay and K888Man over a year ago

Manchester

nice, keep going

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Mark said “OK, it’ll take me at least half an hour to look half decent, you should go and have a bath, and shave those legs, he said looking down, if you really want to feel the joy of nylon.

In the bathroom was a towel with stockings, suspenders, panties, a full length silk slip and a razor, a pair of strappy high heels next to them.

Bath, and shaved as quick as I could, my cock already at half mast, I slid on the black stockings, they felt good, but looked mazing on shaved legs, next the belt, took some time, then panties, and my cock was standing out like a flag pole. As I stepped into the heels I felt a transformation, so feminine, and slutty, I knew this was for me, I stepped into the slip, and caught a glimpse of me in the mirror, Blimey I quiet fancy myself!

Reply privately (closed, thread got too big)

By *ang999Man over a year ago

oldham

Please more

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

I walled down the hall, a natural in heels, i felt my bum wiggle, the draft around my legs, every step becoming more feminine, a thought flashed through my mind of me in the film bent over a desk servicing two men, i quickly dispelled the thought, I'm not gay i told myself.

I went to the lounge and poured another drink, Mark walked in 10 minutes later, WOW! i said out loud, he/she looked gorgeous, short black pencil skirt with a slight spit, white see-through blouse showing a slip like mine below, black stockings and patent black court shoes with a very high heel.

Mark you " Stephine, Stephie when I'm dressed. Mark is straight, but Stephie is all girl" she said. She took a camera out, and said "I don't know where I'd get these developed, but thank you, it helps"

I stood as manly as possible given the circumstances, my cock still standing out through my slip.

She took the pic, then I one of her, and she said, you seem to be enjoining yourself, would you like to try a wig and make up?

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Feedback on here very welcome,

thanks to those who already have x

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Fuck this has made me soaked..

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Never had an intro like that

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Reminds of when….

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

My pleasure…

Xxx

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Reminds of when…."

Sounds Interesting…

Reply privately (closed, thread got too big)

By *imshardMan over a year ago

kirkcaldy

So horny mmmmm

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

sounds like heaven

Reply privately (closed, thread got too big)

By *agical HandsTV/TS over a year ago

wellingborough

Ooh I can't wait to hear more. I'd of loved something like this happen to me years ago. So hot.

Reply privately (closed, thread got too big)

By *iona38ddTV/TS over a year ago

north east fife

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Yes of course I would, although a little male in my head screamed no, I was intoxicated. Stephie reruns with wig and make up, “Sit in a dining chair” she sits opposite, “open your legs so I can get closer”

I part them and even the feeling of my suspender-belt pulling at my waistline is a turn on, not that my cock could get any bigger, Stephe pulled her chair in and our nylon clad legs touch, OH! That’s nice I said, there was a hint of her stocking showing

She spent the next 10 minutes applying foundation, blusher, eyeshadow and lipstick, her hand or elbow often brushing my rampant cock, but she never flinched.

Finished off with a shoulder length wig, she tenderly pecked my lips so as to not mess up either lipstick,

“Go and look in the mirror.”

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

"Feedback on here very welcome,

thanks to those who already have x"

ccccan't give feed bbbback too busy wanking as I read this lovely story xx

Reply privately (closed, thread got too big)

By *oventry4biTV/TS over a year ago

coventry

Wow, this is fantastic. More please

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

"Feedback on here very welcome,

thanks to those who already have x"

I'm absolutely loving this, what an incredible intro and I sense that the even better bit is yet to come.

Reply privately (closed, thread got too big)

By *lare_thomas38TV/TS over a year ago

my town

Really enjoyed this so far x

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

I stood up, still reeling from the spark I felt when Stephie kissed me, the voice in my he screaming he’s a bloke drowned out by feeling so sexy.

I looked in the mirror over the fireplace and drew a deep breath, wow, I look gorgeous, I recognised someone, but felt strangely good looking at my reflection and being turned on.

“What now?” Said Stephie My cock was still holding out my slip like a tent, and now hurt, as I was so turned on, and never had an erection for that long without relief, we could watch your video together?Stephie smiled, we took our drinks and headed for the sofa, Stephie went to sit on a single chair, but I sat on the sofa and patted the seat next to me,

I had no idea what to do, but I wanted this woman next to me

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Hot

Reply privately (closed, thread got too big)

By *anabecdTV/TS over a year ago

Limerick/ tipp

Fantastic story

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

I sat looking at our nylon clad legs, in the distance a young Stephie was on the TV flirting with two guys in an office, flashing the odd stocking top, it felt even more sexy to be with a porn star,

I turned to look at Stephie, and leaned in for a kiss, she pulled back, are you sure, I nodded to the erection still standing up under silk, and we kissed.

It was strange, Like I could taste it was a man, not the sweet taste of a woman, but I’m so turned on, there’s no going back.

Stephie slides on her knees, and parts mine.

She slowly runs her hands up and down my stockings each time moving the slip a little higher, then up over my panties, she leans forward, and kisses my cock through the nylon material then nibbles it too.

She looks up, I smile, there’s no turning back now. She lifts the panties over and down, releasing the beast.

Her hand gently touches my cock, and I flinch, she looks up, I say It’s because I’m so turned on, please don’t stop.

Her tongue runs up the length of my shaft and her mouth covers my helmet, so warn, her head bobs up and down, I glance over her shoulder and young Stephie is doing the same on film and my

Cock twitches

Reply privately (closed, thread got too big)

By *onsi69Man over a year ago

llanfairpg

Excellent

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

I feel my cum rising, so stand up to stop Stephie, helping her to her feet, we kiss, no we snog, hands everywhere as I rock on my heels, I feel her hardness press against me.

I reach around and undo her skirt, and drop to my knees and lower her skirt to reveal lilac cami knickers, a white suspender belt and matching top, I wank her cock through the material and look up, Stephie smiles and I lower her knickers and come face to face with the only cock I've seen outside a porn film.

It's about 6inches, cut with a distinct bend to the left, I move my head forward, gulp, and part my lips.

It slips in my mouth, and I think it's so hard, so hot and I can taste precum.

I close my lips and Bob my head "No teeth please" and I push my lips over my teeth and try again, it must have been good, as I feel her hands on my head and she starts to pump.

I feel like a cheap whore on my knees, stockings and suspenders, high heels and my mouth being used, and I've never been so turned on.

Reply privately (closed, thread got too big)

By *ini1275Man over a year ago

stoke on trent

Omg I'm loving this xx

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

"Omg I'm loving this xx"

Thank you so much

There's nothing Mini about you, I've seen the pics x

Reply privately (closed, thread got too big)

By *aughty sex50Couple over a year ago

Berks

Yes please id love to be in that situation

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

I'm loving every moment of this, on my knees, sucking my first ever cock dressed so sexily, I glance at the video, young Stephie is on a sofa, legs spayed with one of the business men probing her bum with his cock, as it slides in, I feel a twinge in my tummy, I break of sucking her cock, and say I'd like to try that,

Stephie looks at the screen, "are you sure, it's a big step"

I don't know what I'm doing now, I don't know if I'll ever do this again, but right now, I want to feel like a woman and be fucked.

"OK" she said, and went to her make up bag, while I returned to the sofa, "You need a female name, if you're about to become a woman"

I think for a moment, it's Wednesday, Wednesdays child is full of something, I'm about to be full of Stephie. Call me Wednesday.

"Well Wednesday, pleased to meet you, spread your legs"

She kneeled down, played with my cock and sucked it once more, then her tongue started licking my balls, she pulled me closer to her, and now she was at the gap between my balls and bum, and it feels nice, I moan, and a tongue flits across my bum, I flinch, and she pulls back, I look at her, and she says "it's ok, it's the start of getting you ready" She goes back to her work and OMG this feels so fucking good, I relax and spread my legs further, then the tongue is replaced by a finger, probing, and then in me,

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Hot

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Wednesday

This is incredibly horny and very well written. My cock is like iron. Please continue x

Reply privately (closed, thread got too big)

By *oventry4biTV/TS over a year ago

coventry

Keeps getting better

Reply privately (closed, thread got too big)

By *agical HandsTV/TS over a year ago

wellingborough

Omg this is getting hotter and hotter. I'm so turned on.

Reply privately (closed, thread got too big)

By *icurious69jockMan over a year ago

north east lincs

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Wednesday I'm loving this. You have my full attention...can't wait for more.

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Great story,so horny

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

This is a great story. More please!

Pretty please!

Xxx

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Wow!! So good,sexy,and well written,has got me so hard!.xxx

Reply privately (closed, thread got too big)

By *rishman30Man over a year ago

belfast

Amazing

Reply privately (closed, thread got too big)

By *bzsissyTV/TS over a year ago

Aberdeen

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Stephie reaches for her makeup bag, brings out a tube and a small brown bottle. "This is to help you relax" she said, and shows me how to sniff, as the first sniff goes in I feel my face flush red, I'm feeling good, and ready, I look down and see Stephie placing the contents of the tube on her fingers, then on my pussy, oh it feels cold but straight away fingers massage it in, and two fingers easily slide in, the 3, then 4, as she starts to suck my cock again. "I think you're as ready as you can be" she said, reaching for her bag and pulling out a condom.

As she opens it, and starts to roll it on, the male voice in my head shouts no, I wear the condom, I do the fucking, but Wednesday is in control of me, and I want to feel like a woman.

More lube and I feel the hard wide end of her cock at my door, pushing slowly"relax, and sniff" but my sphincter panics and I feel pain, she pulls out, and more lube and fingers, "relax and sniff" she repeats as I feel her push at my pussy, "push out slightly" and then she's in past the tight first few inches, and I now have a cock inside me, I feel strangely full and so sexy, slowly Stephie moves back and forward, she looks so beautiful between my legs as I lose my virginity for the second time

Reply privately (closed, thread got too big)

By *anabecdTV/TS over a year ago

Limerick/ tipp

Can't wait for more

Reply privately (closed, thread got too big)

By *ddie04Man over a year ago

Very hot and horny

Reply privately (closed, thread got too big)

By *ewtothis2219Couple over a year ago

Telford

Beautiful story

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Brilliant story

Reply privately (closed, thread got too big)

By *omenameTV/TS over a year ago

GALWAY

Wow, this is so hot

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Stephie builds up a steady rythm, I'm in some place I've never been, loving someone taking me, instinctively I wrap my legs around Stephie, the feel of nylon and strched suspenders, feet encased in high heels all adds to the feeling

Stephie leans forward and we kiss, from the moment I stood in high heels I knew I was a slut, and now the feeling was complete.

On your knees she said, we disengage, and she has me on all fours looking at young Stephie on the screen.

Once again my bum feels the steel hard cock probe, and slip in, much easier, and as Stephie grabs my hips I feel in her control.

On Screen we have got to the bit where Stephie is over a desk, and a Cock placed at her mouth, mmmm I said, as Stephie increases the pace, I'd like to try that one day, this sends Stephie over the top, she is now banging into me, he balls slapping against me, now I'm here for her pleasure, as she uses me, it feels good.

Stephie is now taking long hard strokes, I know she is near cuming, I shout out fuck me, use your bitch, and one hard pump later I feel her flex, I feel her cock pumping inside of me, and now I really feel like a woman.

At this moment something unexpected happens, my cock, on fire all this time starts to cum, my bum contracts against Stephie as my cock squirts more spunk further than I have ever known.

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

"This is a great story. More please!

Pretty please!

Xxx"

Can't resist a "Pretty Please" x

Reply privately (closed, thread got too big)

By *aughty sex50Couple over a year ago

Berks

Amazing im oozing precum in my sheer pink panties now

May have to get a dildo out and slide up my arse

That feeling is amazing

I need a real cock in me

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

The naughty bits didn't disappoint, loving every drop.

Reply privately (closed, thread got too big)

By *oventry4biTV/TS over a year ago

coventry

Superb

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

"Amazing im oozing precum in my sheer pink panties now

May have to get a dildo out and slide up my arse

That feeling is amazing

I need a real cock in me

Wish I were nearby x

Reply privately (closed, thread got too big)

By *aughty sex50Couple over a year ago

Berks

[Removed by poster at 12/10/21 13:07:26]

Reply privately (closed, thread got too big)

By *aughty sex50Couple over a year ago

Berks

Love the story

My exact type of scenario

I’m lucky as Mrs would love that sex with me and a sexy TV

Reply privately (closed, thread got too big)

By *icurious69jockMan over a year ago

north east lincs

Reply privately (closed, thread got too big)

By *ippythunderMan over a year ago

brighton

Love this story. My cock is stiff rock hard and very wet I just need it pumping dry

Reply privately (closed, thread got too big)

By *idlothian manMan over a year ago

midlothian

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Wow

What an amazing story

Wish it was true

Reply privately (closed, thread got too big)

By *ammyTV/TS over a year ago

manchester

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

A wave of guilt rushes over me, Stephie says"you'll feel guilty after, but I can see the slut in you, so don't stop now, stand up"

She starts cleaning my cock, standing in heels, the guilt subsides.

"Come with me" Stephie takes me to my bedroom and lies on the bed, "straddle me, no the other way" and we're in a 69 position with me above.

Stephie sucks at the tip of my cock, it hasn't gone soft despite cuming

Stephie's has, I lower her Cami knickers and see her cock lying in front of me, I take the full length in my mouth and start to suck, I'm pleased as some life returns to it, I let it slip out of my mouth and lick her balls next.

There is some movement below, I feel my bum cheeks part and a tongue flick my ring, then dive in, why does this feel so good, why do I feel like a slut who will do anything when she does it.

Despite this, I don't feel I'm ready to replay the compliment just yet, so go back to sucking a now hard cock, taking as much in as I can, occasionally gagging, but I feel proud of myself.

Stephie slaps my bum and says move over.

"time for my fun" she says.

She lies me down, wanking my cock then produces a condom and places it on me.

She swings a leg over me and squeezes my middle with her stocking clad legs, I want her and smile, she backs back and I feel my cock pushing at her enterence, she reaches around and grabs me, pushes back and I'm in.

She rides my cock and looks beautiful doing it

Her pace picks up, and her cock is slapping my tummy on the down strokes, I feel in love, I know I'm not, it's sensory overload, guilt is gone and now I'd do anything with this beautiful creature.

She leans forward and we kiss, "wank me" my hand grabs her, wanting to please her. her pace picks up, she reaches behind her and plays with my balls, and I feel my sap rising, I spit on my hand and wank faster, Oh Oh I'm coming I say, she pounds me, and as I feel my spunk release she comes over my hands and tummy, I jump as I've never had this before.

She slowly grinds to a halt and lifts off me with a plop, as she moves forward I crane my head forward and take her cock in my mouth, my first taste of spunk that's not mine!

She says "that's some introduction to cross dressing, you seem a natural slut.

Reply privately (closed, thread got too big)

By *aughty sex50Couple over a year ago

Berks

Fab story

I need a slutty sexy guy like that for regular anal and oral sex

Reply privately (closed, thread got too big)

By *vhazelMan over a year ago

Ely

Reply privately (closed, thread got too big)

By *agical HandsTV/TS over a year ago

wellingborough

I'm ready to burst. I hope there's more to cum.

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

I awake the next morning, still in stockings and supenders, wig off, dry spunk stiff on my body.My bum hurts in a nice way,and my cock is already stiff as memories flood back from the night before.

Mark is sitting in the kitchen "Good morning, no urge to run away to the church and confess all?"

No Stephie, I feel good, strange, sore in places but good.

"Some ground rules, When I'm Like this, I'm Mark, I'm straight, and despite what happened last night, it wasn't us.

If you want to talk about dressing, talk about Stephie and Wednesday like people we know, for example, Would you like Stephie and Wednesday to meet up again? "

Yes I'd love it if we... no they met tonight.

" Good, I'm sure Stephie will be glad, and answer any if Wednesdays questions"

The day went quickly, I went back to the house, but there was no sign of Mark or Stephie.

In my room was a pile of clothes, White stockings, white lace matching suspenders, bra and panties. The wig onna stand, a beautiful blue dress hanging up and red patent court shoes, very high, like Stephie's black ones last night.

There was a note from Stephie, " Bath and shave your chest and pubes please, then dress and come down for dinner"

Stephie was clean shaven all over and I was happy to comply.

Getting dressed was exciting, and once again, stepping in to heels made me instantly femanine and slutty.

These heels were hard to walk in, but I loved the way they made you walk like a woman.

I walked in the dining room, and Stephie was there.

Sit down and I'll do your make up, you need to learn to try yourself.

I kissed her cheek, and she smiled and kissed me fully, along with a squeeze of my bum.

We resumed the position of her between my legs as she applied my makeup, my erection obvious, and this time she was brushing it often, even a little play through the dress.

We talked over dinner, how she started, how she lived in Brighton before this and lived full time as Stephie, but it was so quiet up here, Stephie usually only came out once a month.

We talked about her making the films when she was young, a regret now, but it was fun.

I repeated how sexy it looked over the desk, a cock at either end, and she smiled "Good things come to those who wait"

We put on the same VHS, she said Teacher's Pet was for tomorrow night, Friday night if Wednesday was around?", Hell yes I said.

The night was a repeat of the previous, but this time with more instructions, I was her pupil, but the sex was just as good

I managed to deep throat all her cock with instructions, and this time she was on all fours as I pounded from behind. I rode my first cock and it was beautiful, being in control of speed and depth, we kissed and fucked all night falling asleep in each other's arms.

I awoke alone, dressed, sore and stiff with dry spunk.

On the bed side table was a strange rubber ball shapped bottle and some instructions.

Use this a couple of times today, and we will continue Wednesday's education tonight.

Reply privately (closed, thread got too big)

By *agical HandsTV/TS over a year ago

wellingborough

Omg I'm so excited for the next part. I almost feel as if I'm there.

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Wish this had happened to me! Xx

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

the ball thingy turned out to be a Douche, reading the instructions was an eyeopener, "every days a school day" I thought, little did I know.

There was a message for me to eat before I got home, and not before 7pm.

Fish and Chips and a pint in the only pub in town restored my macho side, but inside all I wanted to do was slip into nylon stockings.

I arrived home, to a quiet house, I realized Stephie didn't want to see me before I was dressed.

In my room was today's outfit, this was starting to feel a little like MrBen I thought.

I bathed, shaved and moisturized as requested.

See through black nylon panties and bra, my cock looking beautiful through the material.

A deep black suspender belt and sheer black seamed nylon stockings and one again my cock is standing out like a flag pole.

Next a tight white cotton blouse, short netball style skirt, and a school tie.

I loved my girlfriends dressing up as StTrinnians, now I was even happier dressed like this myself.

Very high stappy heels, and again, as soon as I stand up in them, I am a woman and a slut ready for action.

My wig is different, blonde and in pigtails.

I look in the mirror and love what I see, the skirt showing the dark tops of the stockings.

I walk, or wiggle down stairs, Stephie is there dressed identically, and I say Wow out loud.

Make up as before plus freckles, and the occasional play with each other.

She hands me a glass of white wine and suggests photos which I love.

Stephie looks at the clock "nearly eight" she says,"tonight I'm stepping up the pace of your education, you have asked for this but if you are not comfortable at any point, say Banana and we will stop and talk"

WTF I think, I've asked for this, my head trying to sort out all this.

Stephie comes over and kisses me on the lips, one hand rubs my cock through the nylon panties, so easily accessible in this tiny skirt.

My legs feel like buckling, I'm so in love, or lust or...

The doorbell rings...

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Still wishing this happened to me!

Xxxx

Reply privately (closed, thread got too big)

By *agical HandsTV/TS over a year ago

wellingborough

Reply privately (closed, thread got too big)

By *ay and K888Man over a year ago

Manchester

nice

Reply privately (closed, thread got too big)

By *imshardMan over a year ago

kirkcaldy

So good im very hard for this x

Reply privately (closed, thread got too big)

By *oventry4biTV/TS over a year ago

coventry

Going to be fantastic

Reply privately (closed, thread got too big)

By *eterpervisMan over a year ago

back where i came from

Reply privately (closed, thread got too big)

By *iona38ddTV/TS over a year ago

north east fife

This is sooooo good

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Reply privately (closed, thread got too big)

By *lare_thomas38TV/TS over a year ago

my town

Ooh this is getting better and better xx

Reply privately (closed, thread got too big)

By *eet or funMan over a year ago

peterborough

Reply privately (closed, thread got too big)

By *evilmademedoitMan over a year ago

Glasgow

OMG!! Wednesday, this is such an incredible read. Thank you for sharing this story with us all. I’m sooooo horny and can’t wait for the next part. Xx

Reply privately (closed, thread got too big)

By *onsi69Man over a year ago

llanfairpg

Oh my days…..

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

The door bell rings, I jump visibly, Stephie takes my hand and walks to the mirror and touches up our lipstick preventing me from talking, I look in the mirror, we both look so hot, can my heart beat any faster?

She takes my hand and leads me to the hall.

Stand here, follow my lead and let that inner slut out.

She turns and opens the door, and then stands besides me against the hall wall

A man walks in, WTF! in his 50's greyish hair, quiet fit looking, dressed in a suit.

"Hello Stephanie, my naughty little girl, you look devine" he goes to her and kisses her, I see his hand slide under her skirt and squeeze her cock hard.

"And this must be Wednesday, your naughty friend you told me about" he leans in to kiss me but I turn away, "it's ok Wednesday, I'm here for fun, we'll take it easy to start"

he gestures to the living room and as I turn I feel his hand on my bum, half of me annoyed, half of me turned on, an interesting feeling, I thought, maybe go with the turned on and see where it goes.

The man walks in with his hand on Stephie's bum, my Stephie, again half jealous she's my girl, half jealous it's not my bum his hand is on

he removes his jacket and hands it to Stephie to hang up.

"Glass of red wine Wednesday, and top up your drinks" I feel strangely compelled to follow his instructions

Stephie returns and puts in the Teachers Pet video, and the man sits on the sofa, in the middle.

I serve him his drink and he pats the sofa either side of him.

We squeeze in either side and the video springs into life.

Young Stephie is one of two schoolgirls dressed exactly as we are in a fake school set.

They start to kiss and caress and the Man puts a hand on each of our legs, I'm frozen, his hand starts rubbing the nylon clad legs, I can't move, except my cock stats to spring into life, NO, stop I say in my head, but as his hand moves higher my cock gets harder, until his hand is on my panties

"Thought you might like it Wednesday girl" he says, massaging my stiffness through my panties

"Why don't you two girls kiss" Stephie leans across the man, and I lean in to meet her.

It's a relief to kiss my friend, but his hand is now wanking me, and it feels good.

Stephie breks off kissing me, and Kisses him, she stops and he leans forward and kisses me. It feels all wrong, he tastes metallic, I know I'm kissing a man, but my cock twinges harder and he can feel it.

Reply privately (closed, thread got too big)

By *ust 58Man over a year ago

london

A delight to read . Looking forward to more

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

God this is hot

Reply privately (closed, thread got too big)

By *j and c 2Couple over a year ago

mullingar

Reply privately (closed, thread got too big)

By *idlothian manMan over a year ago

midlothian

Hell yes. So sexy

Reply privately (closed, thread got too big)

By *enn 53Man over a year ago

belfast

Wow this is brilliant ??

Reply privately (closed, thread got too big)

By *hythmic DriverMan over a year ago

Croydon

I'm loving this and am rock solid too

Reply privately (closed, thread got too big)

By *heryl SatinTV/TS over a year ago

Glasgow

Ohh my, this is a hot sexy tale xxx

Reply privately (closed, thread got too big)

By *agical HandsTV/TS over a year ago

wellingborough

Yes yes yes

Reply privately (closed, thread got too big)

By *ark_sentinelCouple over a year ago

Andover

Reply privately (closed, thread got too big)

By *iggeroo69Man over a year ago

Newcastle

Omg this is fucking amazing

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Inside my head a voice tells me this is wrong, two days ago I felt uncomfortable watching TV Porn, now I'm kissing a man who's wanking my cock while I'm dressed in an outfit that turns me on.

He breaks off and says "Uniform Inspection"

Stephie jumps up and stands to attention facing the tele, I remember she says follow my lead, so stand next to her.

The Man walks around admiring us, "Skirts UP" Stephie lifts her Skirt and I follow.

"Nice, very nice" and he kisses Stephie, agains squeezing her cock hard

"Miss Stephanie, are you wearing make up?" "Yes Sir, sorry Sir"

He says "my office after playtime"

He walks behind me, my legs are trembling, I feel his hand on my bottom, then from behind he reaches around and slips his hand inside my panties and plays with my cock.

" Miss Wednesday, your seams are not straight"

I'm not normally compliant, but the inner slut says " Sorry Sir"

" My Office after playtime"

He sits back down and says "Playtime"

Stephie turns to me and kisses me, we hug and caress, her hands on my bum, she drops to her knees, and releases my throbbing cock and starts to wank and suck it. Young Stephie is doing this on screen and I'm very aware we are putting on a show for Sir, there's butterflies in the pit of my stomach and I love it.

I break off and lie on the floor, Stephie straddles over me for 69, her skirt so short it doesn't stop access, I pull her panties to oneside and out pops her cock and I devour it, as she takes mine,

I deep throat and gag, turned on at the thought of being watched.

I lick her balls, then adjust place slightly, and pull her cheeks apart, I didn't think I'd ever do this, but my love for this girl and my inner slut made me run my tongue across her bud, it tasted of soap, and now back again, and as inhibitions dropped U rimmed my first bum like it was a pussy, forcing my tongue inide.

I hear Sir say "you dirty sluts, very good"

Then he shouts "Playtime Over, my office!"

Reply privately (closed, thread got too big)

By *idlothian manMan over a year ago

midlothian

Oh yes. Love it

Reply privately (closed, thread got too big)

By *eet or funMan over a year ago

peterborough

Great story loving it

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Stephie jumps up and rearranges her clothes, goes to the mirror and touches up her lipstick and make up, and in the refection nods for me to join her, she kisses me and then touches up my lipstick. She whispers in my ear "I'm so proud of you" and my knees nearly buckle I'm so happy. "Listen to your inner slut, and remember you asked for this"

I'm confused, I never asked for this.

Stephie walks over to the dining table and bends over, pats the table next to her and I assume the position.

Sir walks back in the room, didn't see him leave, "Right, who have we here?" "Stephanie Sir" and she looks at me, her face flat on the table "Wednesday... Sir"

"Ah, my naughty girls, right, Stephanie, make up at school, six of the best, Wednesday, your new, uniform incorrect, 3 of the best!"

I'm not sure what's next, but I'm not sub and I don't think I'll like it, but I look in Stephie's eyes and so want to please her.

Sir walks behind Stephie, raises her little skirt and lowers her panties, THWACK! the sound of a Cain, and Stephie flinches, 2,3,4 is that a tear in her eye, what's that word, I can stop this, but my inner slut says she's enjoying it... 5,6 "What do you say girl" sir says, "Thank you Sir"

next I feel my skirt rise, panties gently lowered, THWACK! fuck that hurt, 2 Ow! Stephie looks in my eyes as we are both flat face down on the table and mouths "I love You" My heart jumps before 3, fuck it doesn't get easier " What do you say" Sir says, my head is spinning, I can't think Thwack, Thank you Sir comes out automatically,

"Good Girl, Don't make me wait next time"

I feel Sir stand between us and a cool cream on my bum, he gently massages my bottom, then my crack and a finger slips inside me, I imagine Stephie is on his other hand. My cock is bone hard pressed against the table, I notice it didn't go away with the spanking,

more cream, my balls massaged then two fingers work their way in and out of me

Reply privately (closed, thread got too big)

By *oodburnerswMan over a year ago

Ktown

Blown something. Lush read. Thank you

Reply privately (closed, thread got too big)

By *rishman30Man over a year ago

belfast

beautiful

Reply privately (closed, thread got too big)

By *agical HandsTV/TS over a year ago

wellingborough

This is so hot and my ultimate fantasy ??

Reply privately (closed, thread got too big)

By *aughty sex50Couple over a year ago

Berks

Think there are a few on here who would love this scenario

Me for sure

Reply privately (closed, thread got too big)

By *vhazelMan over a year ago

Ely

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Wow

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

WOW this is AMAZING, I'm so jealous, would love this kind of scenario!!

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Great story

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

I hear the sound of trousers undone and dropping to the floor, the table rocks and I'm guessing Stephie is getting Sirs cock from behind, a rhythm slowly building up, I want to look, but I want to please Stephie and we look into each other other's eyes as she's pumped from behind.

The rhythm stops, and a thumb appears at my bum, cold lube worked in.

I'm prone across the table, what's left of my male side says run, you didn't sign up for this, but my inner slut makes my hands pull my bum cheeks apart... a cock nudges the enterence, "A real pleasure this, breaking in a new girl" says Sir, he's gentle, at first, but once in, he slaps my bum and picks up the speed and force. Stephie and I made love, but here I am being fucked, used, like the slut I am. Much to my surprise Stephie moves away, I am moved so I am now over the corner of the table, my head leaning over, Sir is fucking deep and hard, I see Stephie's skirt walk up to my face, and look up, she smiles and says "you did ask" she raises her skirt and pulls her cock out and offers it up to my mouth, the penny drops for a third time, Young Stephie bent over a desk being spit roast in the film, I had said I wanted that.

I opened my mouth and a new feeling of completeness as two cocks pumped away, using this cheap whore for their pleasure and I love it. Days earlier I was a straight bloke who occasionally wanked in a pair of panties, now I craved stockings and heels and cock, Stephie cum first, the first time she had come in my mouth, I coughed and sputtered but happily drank her down, next I feel Sir's hands pressing down and he starts to spunk inside me, It's warm and I realise he has no condom on, but by now I trust Stephie and enjoy the feeling.

" What do you say? "

Stephie and I say " Thank you Sir" in unison

Reply privately (closed, thread got too big)

By *idlothian manMan over a year ago

midlothian

I’d love to be you in that situation

I’d love to get spit roasted as a sexy school girl

Reply privately (closed, thread got too big)

By *agical HandsTV/TS over a year ago

wellingborough

Beautiful story ?

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

We returned to the lounge and out drinks and Video.

We spent the night fucking and sucking and playing, I remember at one point being tied down over a chair while Stephie inserted various fruit and veg in me while Sir took pictures (His thing apparently) and when Sir left we linned up to kiss, hug and thank Sir as he left.

We went to bed for some gentle cuddles, and fell asleep.

I was working Saturday, I woke alone, when I went to the Kitchen there was a note.

"I think Wednesday and Stephie need a rest tonight, but Stephie said you can dress all day Sunday and your education will continue!"

Hope you have enjoyed this so far.

Shall we leave it here or shall we find out what Stephanie has planned for Sunday?

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Please tell us Sunday's story. Xx

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

More please.

Reply privately (closed, thread got too big)

By *eterpervisMan over a year ago

back where i came from

Love to find out what happens on Sunday.

Reply privately (closed, thread got too big)

By *agical HandsTV/TS over a year ago

wellingborough

Pretty please can we find out what happened on Sunday x

Reply privately (closed, thread got too big)

By *imshardMan over a year ago

kirkcaldy

Sunday please

Reply privately (closed, thread got too big)

By *UCKER56Man over a year ago

Walsall

Fantastic ..

Reply privately (closed, thread got too big)

By *usie pTV/TS over a year ago

taunton

OMG a lot of this seems very familiar, so good xxxx

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Sunday please

Reply privately (closed, thread got too big)

By *eeker of pleasureMan over a year ago

manchester

Crack on

Reply privately (closed, thread got too big)

By *ndyrTV/TS over a year ago

southport

Absolutely fantastic xx

Reply privately (closed, thread got too big)

By *takerMan over a year ago

gosport

This is very good

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Absolutely fucking incredible....

Reply privately (closed, thread got too big)

By *lare_thomas38TV/TS over a year ago

my town

Absolutely loving this Wednesday, keep up the good work hun x

Reply privately (closed, thread got too big)

By *evilmademedoitMan over a year ago

Glasgow

Please continue this, such an incredible tale, can’t wait to read more. Xx

Reply privately (closed, thread got too big)

By *vhazelMan over a year ago

Ely

Roll on to Sunday please

Reply privately (closed, thread got too big)

By *vanabeusedTV/TS over a year ago

somewhere

Wish this happened to me years and years ago xxx

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Thanks for all the kind compliments and comments.

Wednesday will return on Sunday, so to speak...

I'll start a new post Thursday Wx

Reply privately (closed, thread got too big)

By *ark_sentinelCouple over a year ago

Andover

Reply privately (closed, thread got too big)

By *etasubTV/TS over a year ago

West London

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

OK, Part II has started in a new thread.

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

First Class

I’m off to find part2

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

"This is a great story. More please!

Pretty please!

Xxx

Can't resist a "Pretty Please" x"

OMFG I think I'm in love. This is amazing x

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

"This is a great story. More please!

Pretty please!

Xxx

Can't resist a "Pretty Please" x

OMFG I think I'm in love. This is amazing x"

Thank you,

Think I'm in love after seeing your profile pics x

Reply privately (closed, thread got too big)

By *ewtothis2219Couple over a year ago

Telford

Wow this is amazing

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

Thanks for all the comments.

My fist time writing, and you have all made it worth while

Wednesday xxx

Reply privately (closed, thread got too big)

By *acabiscuitsMan over a year ago

exeter

Amazing story

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

re-reading my favorite story,

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Wonderful story xx

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

New chapter available

What Wednesday did next x

Reply privately (closed, thread got too big)

By *es for funMan over a year ago

port talbot

27 weeks ref

Reply privately (closed, thread got too big)

By *ane08TV/TS over a year ago

redruth/ camborne

I am so wet with pre cum xx

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

So hot I'm on edge reading this so hot. Definitely time to release

Reply privately (closed, thread got too big)

By *iM4kinkMan over a year ago

San Antonio

i want to be Wednessday.

Reply privately (closed, thread got too big)

By *ini1275Man over a year ago

stoke on trent

So so sexy story got me so turned on x

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Brilliant story, more please.

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

"Brilliant story, more please."

Thanks for all your kind comments,

There is a part 2,

What Wednesday did next.

https://m.fabswingers.com/forum/stories/1230186

Reply privately (closed, thread got too big)

By (user no longer on site) OP over a year ago

I should have said part 2 is

Introduced to Crossdressing PartII

and part 3 is "What Wednesday did next..."

Which I've just updated

Wednesday xxx

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

great story, love it

Reply privately (closed, thread got too big)

By *ressed4fun03TV/TS over a year ago

Midlands

Id love this to be me

Reply privately (closed, thread got too big)

By *av501TV/TS over a year ago

Mancetter?

Great story pity OP has gone off

Reply privately (closed, thread got too big)

By (user no longer on site) over a year ago

Reply privately (closed, thread got too big)

By *hisismeXXXMan over a year ago

Welsh Wales

Many years ago when I was 19/20 I had a relationship with an older lady (early 30s) who taught me an awful lot about sex!

One night when we played she suggested I wear her stockings for some fun which I was up for and it went from there.

We started having sex with both wearing her stockings and suspenders, then she bought me my own set.

Before long we'd go out together to buy matching lingerie, sets, basques etc and we'd do photo shoots etc, sending the film off to PO boxes in the back of magzined to be developed!

Eventually we'd be going out for nights out, regular vanilla nights to normal clubs, dressed normal but with matching lingerie on, knowing each others secret.

Once or twice she went as far as making me up fully for a night of fun at home and styling my hair. I can't say I ever loved dressing and I certainly was never convincing but she found it incredibly horny and it drove her wild. That I did love!

Up to that point I’d only ever considered myself 100% straight.

It was on holidays in PdI that we first met a few genuine beautiful dressers on a night out and that really intrigued us both - and made us fuck like crazy back at the hotel. One of the last nights on holiday, a visit to the old yumbo centre saw one thing lead to another and ended with the most gorgeous TV masturbating in front of us until they came over my partners feet in her sandals.

That was the night I discovered I was attracted to dressers. Also, it was the night that led to our adventures involving others.

I’ve never dressed with any other partners but, I wouldn’t hesitate if asked again given how much she enjoyed it.

Reply privately (closed, thread got too big)

By *N72TV/TS over a year ago

Cork

This story is so hot, it describes the emotions perfectly. This is why I love being a tranny

Reply privately (closed, thread got too big)

By *vanabeusedTV/TS over a year ago

somewhere

Many years ago when I was 19/20 I had a relationship with an older lady (early 30s) who taught me an awful lot about sex!

One night when we played she suggested I wear her stockings for some fun which I was up for and it went from there.

We started having sex with both wearing her stockings and suspenders, then she bought me my own set.

Before long we'd go out together to buy matching lingerie, sets, basques etc and we'd do photo shoots etc, sending the film off to PO boxes in the back of magzined to be developed!

Eventually we'd be going out for nights out, regular vanilla nights to normal clubs, dressed normal but with matching lingerie on, knowing each others secret.

Up to that point I’d only ever considered myself 100% straight.

That was the night I discovered I was attracted to dressers. Also, it was the night that led to our adventures involving others.

I’ve never dressed with any other partners but, I wouldn’t hesitate if asked again given how much she enjoyed it."

The holy grail . We all wanted a fabulous lady like that when we were younger x