FabGuys.com mobile

Already registered?
Login here

Back to forum list
Back to Stories and Fantasies

How I started dressing (and more) Part 2

Jump to newest
 

By *ekyllChris OP   Man
1 week ago

Lincoln

I’ll set the background first

So I’d been seeing Pam for about 6 months, she was a nurse and I was a fitter, we both worked shifts so when we had time off together we always made the most of it.

With us both having fairly well paying jobs we would go out quite a bit, mainly with her work colleagues as they went out mainly as couples, with my work mates it was more a lads night out type of thing!

We would often go out have a great time, have a few too many to drink, get a kebab on the way home and end up having sex.

She was quite vanilla to be honest

We moved jn together and one night she got a little more adventurous, both quite d*unk she told me I could have anal but only with her riding me, it was really good, but she had this thing telling me how good it was of her and did I enjoy fucking her arse and did I realise how special it was etc etc

To be fair it was quite good as she had never had anything up there before lol

Reply privatelyReply in forumReply +quote
 

By *umslut7Man
1 week ago

dunfermline

Nice start

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
1 week ago

Lincoln

So we get an invite from one the lads at work (Jim but for some reason he was always known as Jamie!?)

Jamie and his misses (really can’t remember her name so I’ll call her Sally! lol) had just moved into there new house and we’re having a house warming party, he’d warned his neighbors lol

On the invite it says “fancy dress” more details to follow, so ask Jamie what they were thinking, Sally has some mad ideas (she was a bit off the wall at times) and everything she had suggested Jaime didn’t think many people would like it

About a week before I get a text from Jamie (god knows why we were at work together!) basically Sally wants a Crossdressing party! I’m sort 50/50 on this, love dressing and secretly still did but at that sort of party it would all be hgv fitters dressed as woman! She wanted the women dressed as men too.

I just reply “oh ok”

Jamie reply’s “that’s why I text you, not said anything to anyone else at the moment, what do you think?”

I reply “well it could be a laugh, plus we really don’t want to upset Sally 😉”

We agree to talk about it at dinner

Reply privatelyReply in forumReply +quote
 

By *erry55Man
1 week ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *ndstorm45Man
1 week ago

Wakefield

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
1 week ago

Lincoln

Me and Jamie chat it over over dinner, Simon walks in “what’s up with you 2???” (Simon’s one of those that just loves his job and the company, says he’s coming out with us all but never turns up and then there’s some bull shit excuse!)

“Where just talking about Jamie’s house warming party” I reply

“Oh yeah, what about it?” Replies Simon

I just say “well Sally wants a dressing up party, blokes as women, women as blokes”

“Oh right” Simon replies not batting an eye lid at it

“See” I said to Jamie, “no one’s bothered it just a a bit of a laugh at a party”

“Ah yeah your probably right”

With that he texts everyone and lets them know

Reply privatelyReply in forumReply +quote
 

By *erry55Man
1 week ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *harlotte39cdTV/TS
1 week ago

rochester

More please xxx

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
1 week ago

Lincoln

The Saturday of the party has arrived, plan is for everyone to go round to Jamie’s and get changed there (makes sense lol)

My misses has sorted out all the clothes but she won’t show me anything or even give me an idea of what she’s got!

We get to Jamie’s about 7pm, got our bags and some beers/wine, Sally opens the door, we’re the first ones there. Grab a seat and Jamie gets us a drink, couple of minutes later the door goes again and the Chris (yes 2 of us at work!) and his misses, loads of chatting and taking the piss etc

About half an hour goes by and we’re thinking it’s just the 6 of us, door bell goes again, it’s Katie, the one girl that works with us (well she worked up stairs doing all the admin) we don’t really have much to do with her in all honesty, she’s about 5’6” tall quite sort of plain but nice.

She comes in with her partner, Katie looks stunning, one peice dress, stockings , heels etc really pert looking breasts too.

Her partner walks in, turns out she’s a lesbian, her misses comes in dressed as a man, she’s tall (about 6 foot) not as slim as Katie but not fat.

We all go back to chatting, then Sally says “well looks like this is it, let’s get changed boys and girls) we then go up stairs and get shown our rooms to get changed in. We get the larger 2nd bedroom as we’re staying the night.

Reply privatelyReply in forumReply +quote
 

By *unwithuMan
1 week ago

Manchester

Reply privatelyReply in forumReply +quote
 

By *erry55Man
1 week ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *ashtoolMan
1 week ago

belfast

Reply privatelyReply in forumReply +quote
 

By *ubdomtvTV/TS
1 week ago

Wolverhampton

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
1 week ago

Lincoln

Pam starts going through her bag, looks round at me and says “well strip then”

I strip down to my boxers, she pulls out a bag a just looks at me “those too!”

“Feels a bit weird being naked on my own” I reply

“For fucks sake” and with that Pam strips naked, “better?” She asks

“Oh ok”

She then pulls out a lacey pair of thong panties, you know the ones where you can basically see through them! Then a suspender belt, stockings and lacey bra to match the thong

“Get them on and we’ll see how you look” she says

I slide the thing on, put the bra on and start with the suspender belt and stockings

“Come here” she says, I walk over

“The suspended belt goes under the panties” she says as she pushes them through

I sit on the bed and put the stockings on (very feel so so lovey) clip the front clip on them but I’m struggling with the back one

Pam moves over and clips them on for me

While I’m doing all this she has put a pair of my jeans on and a t-shirt, well in a fashion she was slightly bigger than me

“Let’s have a look” she says

“Not bad at all”

She then puts a blonde wig on my head, looks more sort of jokish than real

“Right” she pulls a skirt and blouse out and some socks

“What the hell are they for” I ask pointing at the socks

She walks over and puts them in my bra “that’s what there for”

I slide the skirt on, it’s a little tight but it fits, it’s sitting about half way up my thighs but I feels ok

Blouse on next again maybe a little tight but it’s ok

She then pulls out some heels, there not massive but I’m just like “what the hell??”

They fit perfect but I can’t really walk in them.

You can put them on downstairs for effect she says

Pam is really enjoying this, we end up in the bed having a crazy kissing and cuddling session before we both realise we need to go down stairs

Reply privatelyReply in forumReply +quote
 

By *erry55Man
1 week ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *harlotte39cdTV/TS
1 week ago

rochester

Omg i absolutely love this

Reply privatelyReply in forumReply +quote
 

By *usan 749ukTV/TS
1 week ago

Bangor

Nice

Reply privatelyReply in forumReply +quote
 

By *ayboy57Man
1 week ago

Stoke on trent

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
1 week ago

Lincoln

Should say all the underwear is black, the skirt is shiny Lycra slightly tight but stretchy, blouse is white with buttons up the front.

On the way down the stairs I realise I’m quite turned on by all this and my cock is quite hard, i tried to sort of “tuck” it into my panties but there quite small and as I look down I can see the bulge trying to push through my skirt!

I wanted to turn round and try to adjust myself but Pam was right behind me with my heels and Jamie just shouted “about bloody time!”

I get to the bottom of the stairs and Pam hands me my heels, I pop them on and nearly break my neck getting in the front room, but it was worth it

The other Chris is stood there in what I can only describe as a ball gown, full length in black his misses was stood there in a pair of work overalls (I had absolutely no idea then and I still don’t now!)

I hear Sally say “oh sexy babe” I turn and look at her, she looks great, black trousers, white shirt, black tie and brown boots (almost Sargent major sort of thing?) I make some comment about she scrubs up well

I turn further and see Jamie, wow Jamie has heels on (bigger than mine) in pink, black stockings or maybe tights, silver shiney skirt and a gold string strap top (you could see his bra top strap too) finished off with a brown wig and a little make up

I stood and just looked at him, wow this was a guy I had worked with for some years now, he looked so good, “you want a drink the “ Jamie says “yeah I’ll have a beer” I reply

Sally pipes up “girls drink wine or cocktails”

Jamie pops open a bottle of Prosecco, as he goes off towards the kitchen I notice how at ease he is walking in those heels, to me it’s very much like he’s don’t it before and a lot!

He comes back with a try full of drinks for everyone, Sally comment “that’s my little waitress” we all giggle but to me the look on her face tells a different story, but maybe I was reading too much into it all??

Reply privatelyReply in forumReply +quote
 

By *erry55Man
1 week ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *harlotte39cdTV/TS
1 week ago

rochester

Ooh i think hes done it before !

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
1 week ago

Lincoln

The nights going great and we’ve all having a laugh and few drinks, about 9pm Katie and her misses have to go (double booked apparently!)

They go of course once they’ve gone all the comments (where the cucumber gone, which wears the trousers really etc)

There’s the 6 of us and Sally suggests a game, the men ring a good delivery place and have to take the food from the driver

Ok so Jamie starts and rings the local Chinese, 30 minutes later knock on the door, off Jamie totters, answers the door gets the Chinese and off they go, we’re all pissing ourselfs laughing but it’s not like anything happened, Jamie says “the bloke just wasn’t bothered at all”

Next my turn so I ring the pizza place, delivery was about 40 minutes, door goes and I’m thinking “what the fuck!” But I’m fairly pissed and off I go, stumbling all over in these heels, open the door and the bloke starts to say “delivery …” and stops and just stands there looking me up and down “think there are’s” I say to him

“Oh yeah” “some party your having” he says and winks, I close the door and again the same laughing and piss taking

Next up the other Chris, he rings the kebab house, there here in about 10 minutes (there very close and the kebab is _errible to!) Chris goes to the door, opens it all we hear is “what the bloody hell” from the delivery driver, apparently Chris just grabbed the bag and slammed the door shut

Again we all fell about laughing and started taking the piss!

More drink flowed and we eat what we had ordered, I wondered when the girls would have to do it but no one seamed bothered by that plus we had loads of food and who would be bothered by a woman dress in jeans etc

Gets to about 2am and the other Chris and his misses are leaving, they literally live a five minute walk away (found out Monday it took them about 20 minutes lol) so off they went, couldn’t even be bothered to change

Reply privatelyReply in forumReply +quote
 

By *ornishfetMan
1 week ago

St Ives

Reply privatelyReply in forumReply +quote
 

By *kblokeMan
1 week ago

milton keynes

Reply privatelyReply in forumReply +quote
 

By *erry55Man
1 week ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
7 days ago

Lincoln

We all decide it’s late so yeah let’s go to bed, somehow and for for reason we decide 1 more drink before we go up (like we’re not pissed enough!) we get another a drink and Sally starts telling Pam about the size of Jamie’s cock

“It’s big enough for me to have an orgasm to two” she jokes

“Go on Darling so them” she says to Jamie

With that he lifts his skirt and slides his cock put the side of his thong

It’s semi hard at this point about 7inch but quite girthy

“See I told you” says Sally

“Yeah it’s not bad at all is it” says Pam

Then Jamie starts messing around laughing saying “see iv got a great big cock” and starts shaking it round and pushing his hips forwards towards me

Have to admit it did look good (at this point I’d never watched gay porn but plenty of tranny porn)

He trust forward and his cock was about an inch from my face, fuck it, I opened my mouth and took this cock in and started sucking

I heard the 2 girls giggling and I felt Jamie getting bigger

I started to try and take more but as it grew I realised I wouldn’t be about to so I got my hand round the base and started wanking him and sucking at the same time

Suddenly with out any warning Jamie let’s put a massive moan and his load is shouting in my mouth

I pull back a bit but I mange to take it all!

Sally is clapping and says “good boy”

I look at Pam and she is just smiling but seams ok with it (hopefully)

Reply privatelyReply in forumReply +quote
 

By *erry55Man
7 days ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *ornishfetMan
7 days ago

St Ives

Looking forward to hearing more !!

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
5 days ago

Lincoln

I need to pee bad so Pam says we may as well go to bed

We go upstairs and I go for a pee, I open the toilet door and Pam is stood there “you wait there!” She says

I’m thinking maybe she’s not happy about what’s just happened!

She comes out and tells me to follow her, we go to the bedroom, I close the door behind me, turn round and Pam’s tongue is straight down my throat

“Taking it easy” I say

“That was so so horny” Pam says

We start stripping off, I’m told to leave my bra, thong and stockings on, we come close again and start kissing, Pam’s rubbing my cock through my thong I start rubbing her pussy, it’s so so wet, iv never felt it like this before!

Pam gets on the bed, opens her legs and tells me to eat her, I do as I’m told

After a bit of licking my face is covered, I slowly make my way up her body, kissing her stomach, sucking her nipples and then kissing, think she likes the taste of her own pussy.

I try to slide my cock into her and all I get is “no not yet”

She gets up and pushes me on my back on the bed, she starts to wank and suck my cock

Then without warning she gets on top of me and starts to try and push my cock in her arse, it’s fairly dry and tight it’s really not going in!

Pam gets off me and starts going through her bag, she pulls another bag out of her main bag, opens it and gets a bottle of baby oil, she pours it over my cock, wanks it a couple of times and gets back on, she just slides me in her arse balls deep straight in, fuck it feels so so good, it must have been good as Pam lets out a “fuck yeah”

She puts her hands on my bra covered chest and starts sliding up and down slow and steady, I’m loving it, she’s moaning and and just continually saying “fuck yeah”

Reply privatelyReply in forumReply +quote
 

By *ohnny 52TV/TS
5 days ago

Middlewich

Reply privatelyReply in forumReply +quote
 

By *kblokeMan
5 days ago

milton keynes

Reply privatelyReply in forumReply +quote
 

By *erry55Man
5 days ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *eadar123Man
5 days ago

dublin

More please

Reply privatelyReply in forumReply +quote
 

By *oxy4youTV/TS
5 days ago

Henfield

Reply privatelyReply in forumReply +quote
 

By *andy PearsTV/TS
5 days ago

Walsall

Wow love it

Reply privatelyReply in forumReply +quote
 

By *annasuckcockMan
5 days ago

ibstock

Love it

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
4 days ago

Lincoln

Suddenly there’s a groaning sort of sound next door swiftly followed by “fuck yeah take it bitch!”

We’ve been so wrapped up in one another we hadn’t heard a thing until this point.

Pam stops and looks at me as if to say “WTF?”

“Oh fuck” followed by “you’re going to have it!”

It goes on “it’s to big, please I’m trying” we realise it’s Jamie and Sally

Sally replies “you’re trying hard enough!”

By this point me and Pam are totally engrossed in this, it carriers on Jamie moaning in a sort of painful ish way and Sally basically telling to take it in varies different harsh ways!

Reply privatelyReply in forumReply +quote
 

By *erry55Man
4 days ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
3 days ago

Lincoln

Pam continues to ride me slowly while having one ear on what’s happening next door, suddenly Pam shouts out “yeah make him have it!” Well

I’m in total shock Pam just isn’t normally like this, maybe it’s the situation maybe it’s the alcohol who knows?

With that the voices stop next door, Pam looks at me like what have I done? She’s still riding me and never missed a beat during all this.

Suddenly the door burst open, Jamie stumbles through dressed in a basque, stockings and heels, closely followed by Sally.

The room was only light by a small table lamp but you could quite clearly see Sally had a large strap on (when I say large I don’t mean like the horse size things in movies but it must have 12 to 14 inch’s!)

She tells Jamie “get on all fours bitch” she then puts a foot on his arse and stands proudly shanking her strap on about, she looks across at Pam and say “he really should be able to it” more of a statement than a question!

I’m looking at the thing thinking blood hell he really shouldn’t be able too but just smiles back and replies “hell yeah”! WTF Pam’s turning into a right dirty bitch!

With that Sally gets behind Jamie and just push’s this monster up his arse, Jamie’s moaning, groaning, nearly screaming all at once, Pam and I are in shock but we realise it’s probably only just over half way in!

Reply privatelyReply in forumReply +quote
 

By *erriTV/TS
3 days ago

Hastings St Leonards

Reply privatelyReply in forumReply +quote
 

By *ethro65Man
3 days ago

Sutton-in-Ashfield

Reply privatelyReply in forumReply +quote
 

By *axludlowMan
3 days ago

ludlow

:

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
3 days ago

Lincoln

Sally keeps trying to get it in, Jamie continues to complain!

Pam is still riding me and she must be getting turned on by it all as she’s going faster and faster, I can’t hold on anymore and cum inside her, she looks at me sort of frustrated but annoyed at the same time “oops” she says

Sally’s had enough, she smacks Jamie’s arse, he makes a bit of a squeal, she pulls the strap on out and just say “Right!” gets and goes off only stopping to tell Jamie to “stay there bitch!”

She comes back shortly after with a bottle of lube and a smaller dildo, “well you can normally manage this” she tells Jamie, she pours some lube on his asshole and just pushes the dildo straight in (I’m going to guess about 10”) it goes straight in to the hilt! Jamie just lets out a groan, “see wasn’t that hard was it?” Sally says to Jamie, he just nodded and moaned

Sally continues to use the dildo on Jamie, Pam’s got off me at this point and is just staring at Jamie and Sally

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
3 days ago

Lincoln

Sallys proper going for it in Jamie, she’s pulling the dildo right out and then straight back in balls deep in his ass! Jamie’s making so many noises I’m not sure if he’s loving it or hating it!

From where myself and Pam are positioned on the bed we can just see Jamie’s arse but with the way Sally is facing the opposite way to Jamie we can’t clearly see the mid riff section

Sally suddenly shouts out “you dirty bastard, I can’t fucking believe you’ve just done that!” And starts proper smacking and punching Jamie’s arse (turns out Jamie has cum from it all), Sallys pissed off well and truly, as she’s smacking Jamie’s arse he goes to move away from her “don’t you fucking dare you little shit!”

Jamie gets back on all fours, Sally smiles at Pam and says “want to try?” Offering her the dildo, Pam’s there pushing it straight in deep as it will go! Sally turns to me “shut the bitch up!” Having seen how she was with Jamie is wasn’t arguing, I got off the bed and put my semi hard cock in Jamie’s mouth “that’s better much better “ says Sally

Reply privatelyReply in forumReply +quote
 

By *erry55Man
3 days ago

Portlaoise

Reply privatelyReply in forumReply +quote
 

By *ohnny 52TV/TS
3 days ago

Middlewich

Reply privatelyReply in forumReply +quote
 

By *ashtoolMan
3 days ago

belfast

Reply privatelyReply in forumReply +quote
 

By *axludlowMan
3 days ago

ludlow

Reply privatelyReply in forumReply +quote
 

By *ekyllChris OP   Man
2 days ago

Lincoln

We’re all having some great fun (not sure Jamie’s is lol!) he’s great at sucking cock and taking a dildo deep.

Sally stops Pam and the dildo is taken out, Sally and Pam swap places, Sally tells Pam to “hold him open” pours some lube on her strap on and on Jamie’s arse, places the head of the strap on against his used hole and starts pushing it in, I’m watching it slowly disappear into Jamie like some magic trip but I’m also feeling it too as Jamie’s sucking is slower but harder

It’s going, going, and just like that it’s buried in his arse, Jamie releases my cock and let’s out a cry “push your cock in his mouth and hold it there” shouts Sally. Jamie isn’t going to get away from it this time, Pam’s holding his asshole open and Sally is now sliding in and out full depth each time, Jamie’s sucking me to a point where it’s nearly painful, I feel like I’m going to cum, “I’m so so close” I say out loud, “let him have a treat then” says Sally, I shout my load not long after

Sallys now in full swing, my cocks going limp and no longer any good as a gag, without a word Pam gestures to me to move out the way and she opens her legs in front of Jamie, pushes his head down on her pussy, you can still hear Jamie’s moans, groans and noises but there a lot more muffled

I move to where Pam was, holding Jamie’s arse open, Sally looks at me “loving it isn’t he?” “Looks like it” I reply “I think you’d love it too” “way too much for me” I reply we kiss and start sucking her nipples (didn’t know at the time but playing with her nipples can make her orgasam apparently!) she’s now full on pounding Jamie’s arse, the strap on isn’t coming out as much at all, she’s going for it and he’s taking it like a champ

I take one hand of his arse and start wanking his semi hard cock, he’s proper moaning now, Sally is going for it, Pam is moaning from Jamie’s tongue, Jamie’s cock suddenly explodes in my hand, what have I done? I just look at Sally and show her my hand, she laughs and pushes it to my mouth, I lick off the cum, she looks at me and we kiss, I put my hand on her sexy ass and I can feel something’s going on, she just looks at me smiles and pulls the strap on of Jamie’s arse, she’s cum from it all

She smacks Jamie’s arse and tells him to “work that tongue hard in Pam’s clit” then puts her hand on top of Pam’s that’s on the back of Jamie’s head and really pushes his head onto Pam “yeah bitch make her cum” Pam’s breathing a lot faster and in no time has an orgasam (Pam has never squirted but the taste always changes once he’s cum) they both let of Jamie’s head, he just falls on the floor, laying there gasping for air

Sally puts a finger in Pam’s pussy, pops in her mouth and says “not bad” sticks it back in and then into my mouth, I nod and agree, she then pops it back in and then into Pam’s mouth. Pam just smiles they both kiss and Sally says we better get to sleep, she nudges Jamie’s with her foot and says “bed time bitch” Jamie just looks at her half a sleep half exhausted “oh the poor darling is worn out” she then stands up, grabs Jamie’s hair and starts to go, Jamie’s stumbles to his feet and follows Sally out the room

I close the door, Pam and I get in bed, Pam says “what a night” “yeah your not joking” I reply and we both nod off

Reply privatelyReply in forumReply +quote
 
 

By *erry55Man
2 days ago

Portlaoise

Reply privatelyReply in forumReply +quote
Post new Message to Thread
back to top