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Winning a Bet. A crossdresser's journey

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By *ilmisskinkyboots OP   TV/TS 41 weeks ago

Edinburgh

Lilkinkyboots

55CD/TV cock whoreEdinburgh, City of Edinburgh, United Kingdom

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Writing by Lilkinkyboots. Nov 18, 2023

EROTICA 1 MIN READ

Winning A Bet

Regarding the picture of me nude under a leather coat wearing thighboots.

About 15 years ago I used to teach (adult) nightclasses. One of the students was another mate who my partner and I had played with a few times, along with his wife. All of us bisexual.

We had met for lunch and he asked me about the thighboots he knew I owned, the usual questions I suppose. At some point we made a bet that I could get from where the class took place to his house ( he would be giving me a lift anyway), as naked as possible without anyone knowing.

Come the night we had agreed, class as normal, at the end. I excused myself from the usual end of class groupchat and headed for the changing rooms. Stripped off except for a pair of motorbike boots that were tall enough to cover my shins to the coat hem, as it was summer and still light around 9pm, so the heels of the thighboots would've been obvious. Closed the coat completely to hide my nakedness and headed out after checking I was well covered and headed out.

Getting into his car I fished my thighboots out of my bag and switched boots. That was joint breaking, haha. I should've done it in the back seat, lesson learned.

It was a twenty minute or so drive to his house, so I occupied myself by pulling out his cock and wanking him as he drove.

Getting to his apartment block he drove into the underground parking area. We parked up and got out. Him standing there locking up with his hard cock still standing free of his zipper. I walked a little away unbuttoning my coat and did a spin, which opened it completely, exposing my nudity. Thankfully the parking area had no security camera at that time.

He came towards me, taking my cock in hand, and pulled me back to the car. Pushed me to my knees as he leant against the front wing. I began sucking him off there and then. Visible to anyone who looked down the grate above, or who drove in, or opened the door to access the parking area. It was hugely horny making and terrifying. I felt I was literally dripping precum.

After a bit he pulled me to my feet, reached into the car glove compartment and pulled out lube! The swine was prepared!

Bending me over the car's front wing he lubed my ass, and his cock copiously. Gripping my hips he freestyled his cock into me, sliding in my tight hole until he was balls deep. Leaning forward, putting his hands on my shoulders to pin me down he fucked me hard and fast, my own cock squashed against the metal of the car, still dripping precum. I was in heaven. Gasping quietly, he came, and I could feel every spurt inside me. Pulling out and zipping up he reminded me the girls were waiting to see the results of the bet. So off we toddled upstairs.

Let me know if you'd like to know what happened next

X

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By *ree diverMan 41 weeks ago

Dudley

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By *eglover62TV/TS 41 weeks ago

Ayr

I’d love to know what happened next x

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By *izcdTV/TS 41 weeks ago

Wales

I certainly would l9ve to know what happened next

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By *ameisnawtyMan 41 weeks ago

anywhere

Definitly

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By (user no longer on site) 41 weeks ago

Love to know what happened next

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By *eathersarahTV/TS 41 weeks ago

warrington

Keep going

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By *amantha_kelTV/TS 41 weeks ago

Magherafelt

Fantastic let us know what happened next

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By *hirk999Man 41 weeks ago

oswestry

wow

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By *orgotten22Woman 41 weeks ago

out in the sticks in the north east england

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By *ickylouCouple 41 weeks ago

Bi

Would love to know more

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By *harlottes ChurchTV/TS 41 weeks ago

Toy me town

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By *athytvsubTV/TS 41 weeks ago

Bulwell, Nottingham

Of course we need to know xxx

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By *erry bull1Man 41 weeks ago

doncaster

More

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By *usie pTV/TS 41 weeks ago

taunton

Yes please

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By *ucksguy2000Man 41 weeks ago

aylesbury

More please

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By *ony 529Man 41 weeks ago

coventry

Mmmmm I can’t wait for more please

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By *nly1meMan 41 weeks ago

here there n everywhere

more please

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By *akbearMan 41 weeks ago

Newbury

Mmmm

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By *issy_named_cTV/TS 41 weeks ago

Edinburgh

All the sissies straining in their cages reading this

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By *ocky 1Man 41 weeks ago

Warrington

Looking forward to reading what happened next

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By *ark_sentinelCouple 41 weeks ago

Andover

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By *oneysmithcdTV/TS 40 weeks ago

Glenrothes

More please

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By *ilmisskinkyboots OP   TV/TS 40 weeks ago

Edinburgh

Thank you for the responses. Part 2 just going up

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By *olflordMan 40 weeks ago

Exeter

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By *ilmisskinkyboots OP   TV/TS 40 weeks ago

Edinburgh

As I turn from the car and head towards the door leading upstairs W, my friend, says "give me your coat". I look at him, his cum running down my legs and into my boots. And point out that would mean I'd have to walk up the three flights, and passed the front door, naked! "And?" is his only response, and holds out his hand. I sigh and give him the coat. As we walk upstairs, me in front as he wanted to watch my ass and balls as I went up the steps, he lightly spanks my ass, and uses his fingers to wipe up some cum, which he likes off his fingers. We pass the front door, and head up to his landing with no issues though.

He opens his door and we walk in. Our partners are in the sitting room, chatting. Fully clothed. My wife is on the shorter side, 40dd tits, hair colour varies, big bum. His wife is a statuesque six foot or so, blonde and 36c. They both look at me and laugh. His wife says "oh I see", (don't think she was told there was a bet on), and asks if I'd like a coffee. Whilst these are being prepared along with dinner. W and I play some more. I kneel in front of him as he chats away and suck his cock. With the coffee's made he insists on cumming in mine. They watch me drink it as his wife strokes my cock, but still no cumming for me. Dinner is ready! During dinner the conversation is fairly mundane but hands are busy under the table. His wife had mine cumming before dessert!

After dinner we head to the sofa, (which is one of those corner affairs with a large footstool/cushion), the other three begin stripping off. W still as hard as a rock! I swear I don't think I've ever seen W without a hardon! It's like his superpower, haha. He sits on one side, stroking his cock and the ladies sit together opposite and demand I ride W's cock so they can watch as they play. As he's hard I grab some lube and wank him. He reaches round with lubed fingers and starts playing with my hole. Pulling me round, he bites my ass as I settle myself onto his cock. Feeling him fill me for the second time that night. I lean back, my booted feet euther side of his as he starts fucking me. As he fucks me, the ladies take turns coming over to suck my cock whilst watching, kissing each other, nuzzling, sucking each others tits and fingering holes. I do love seeing them suck each others tongues. Which I do for W when he pulls my face round.

He pulls out before he cums and suggests I fuck him for the ladies. So he gets on all fours on the large footstool and I get behind, he breathes out hard as I slide into him, smiling at the ladies and taking him by the hips. Pounding his ass hard and deep. The ladies again taking turns, to suck his cock. My wife stands in front of him, and he cranes his head sideways so he can lick her pussy. His wife stands behind me, reaching under to cup my balls, and push her thumb into my stretched hole. Suddenly I cum, shuddering, his wife leans against my back, her breasts hard against me as she stops me from pulling out. She lets me move eventually, and suggests my wife use a dildo on her husband as he "quite likes that". She goes to get one as I flop onto the sofa, my wife teasing her husbands sloppy hole with her fingers. His wife returns and hands off a massive purple dildo to my wife who grins at the sight. Turning to W she places one hand on his shoulder and holds tight as she slides the dildo into him. Fucking him hard enough with it to make her large tits swing.

His wife sits next to me abd we idly play with each other. She asks me to eat her out as she watches her husband, which I do, her cunt tastes wonderful, and she's soon cumming over my face. I lean back from her slit and look over, W's cock is streaming precum, until he groans and jets cum like a fountain, thick and creamy. He collapses onto his face as my wife withdraws the dildo. He rolls onto the sofa and his wife sucks his cock clean, as he gasps for air.

My wife looks at me and my hardening cock (I've been stroking it), lies back on the other end of the sofa and demands to be fucked. So without further ado I move over, get into position and drive my cock into her. As I'm fucking her, W and his wife move up so they can watch. His with puts her hand in my ass, and leans in to suck on my wife's nipples. She does ask me to say when I'm going to cum. It doesn't take long before my wife gushes and cums hard, and W's wife tells me to pull out to cum over my wife's tits. I pull out just in time and shoot ribbons of cum. Some of it gets on W's wife's face as she leans in. She begins licking my cum off my wife's tights. Then kisses her, exchanging the cum back and forth, before swallowing.

We lie there in a heap. Utterly fucked as it were. After a while coffee's are made, and we chat, still naked, until the wee hours before heading home.

We played with them many times, and in a few different places

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By *essica.tv.plymouthTV/TS 40 weeks ago

Plymouth

Mmm so hot, yes straining in my cage, how I would adore to be with a woman and another couple like this, me generally being the sub for all three, so hot xxx

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By *ndrea54TV/TS 40 weeks ago

cambridge

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By *ark_sentinelCouple 40 weeks ago

Andover

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By *ony 529Man 40 weeks ago

coventry


"Mmm so hot, yes straining in my cage, how I would adore to be with a woman and another couple like this, me generally being the sub for all three, so hot xxx"
. Mmmmmm I am exactly the same. I would love to be caged and serve a couple that’s for sure.

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By *j and c 2Couple 40 weeks ago

mullingar

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By *eathersarahTV/TS 38 weeks ago

warrington

Amazing X

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