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Sissy's first meet

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

Staring back at her computer screen Melissa stares at the "1 new message" flashing on her screen.

Taking a deep breath she opened it reading it's contents

"Hello Melissa,it's time to meet. How about at the park at 2pm tomorrow? If in public you wear boy clothes that's fine but you best wear pink panties as I'll be checking! - Owen"

Owen was in Melissa's year at school, although she went by Melvin back then. The two never got on and ended up in a fight once or twice with Owen always picking on Melvin for being smaller and weaker than him.

Melvin started dressing in his older sisters underwear back when they were at-home and continued doing so when he moved into his own apartment after buying his own.

He created an online persona called Melissa and began joining chatrooms to talk to men. He got off on this and slowly his interest changed from just chatting to wanting to meet someone and get fucked.

Sure he'd shown off his dildo skills on cam and sent pics but he'd never even considered meeting in real life.

At that moment there was another ding from her computer. "Well Sissy? I'm waiting..."

Springing to life Melissa responds "Yes sir, I'll be in boy clothes but will get some pink panties for you." With a deep breath Melissa signs off for the night to prepare herself for the day to come.

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

Good start

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

The next day Melissa pulled her pink lacey panties out of her drawer and slipped into them. Feeling their embrace she pulled up her jeans and threw on a t-shirt and headed out the door for the park.

When she got there she saw Owen just as she remembered him from school, taller than her, muscles clearly been keeping up at the gym. Melissa approached slowly in her head telling her it's not too late to back out but before she knew it she was standing in front of him.

"Can I help you... wait" Owen said looking up from his phone. "Melvin Carr? What do you want?"

Melissa struggled to say anything she realised this her chance to back out but looking at Owens face, she knew it was too late.

"You're my date aren't you sissy? Well I always knew you weren't a real man" he says throwing his arm around her neck. "I hope your wearing those panties for me" as questions as he looks Melissa up and down.

He turns and starts walking into the woods demanding Melissa follows him, until they are far from the road where no one can see them. Owen sits down on a nearby tree stump. "Okay Sissy let's see how you follow orders in real life, show me those panties. Don't worry no one can see you."

Hesitantly Melissa undoes her belt and slides her jeans down just enough to show the bright pink bow and lace trim on her panties before pulling them back up.

"Good girl" Owen says as he in does his own belt taking out his cock, slowly stroking it. "Ready for your reward?"

Melissa nods "this is what you've been practicing for" she thought to herself as she got on her knees before Owen. Reaching out to touch it, Owen slaps her hand away.

"I didn't say you were allowed to touch," he said in a rather commanding tone making Melissa shiver. He continues stroking, making sure Melissa keeps watching, watching her bitch her lip in anticipation.

"Open." He commanded standing to his feet with his cock in hand, Melissa opens her mouth welcoming his cock. He slides the tip in and out her mouth for about a minute before pulling out and putting his jeans back on.

"Until our next meet sissy, that's all you get. Next time we're meeting at yours. I expect fully dressed up like the slut you are if you actually want some of my cock."

As he turns to walk away "if you say no, Melvin I'll let everyone know what you really are. Tomorrow work for you? I'll text you." Without awaiting a response he leaves, Melissa still sitting kneeled in front of where he was sat wishing she got a proper mouthful not realising what just happened.

She gets up and exits the woods the opposite way from Owen with the taste of his cock still on her lips, wishing for more.

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By *r 007Man  over a year ago

harrogate

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By *an_buryMan  over a year ago

Birmingham

Wow

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By *asmin999jmTV/TS  over a year ago

wakefield

I am hooked and waiting x

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By *us man1957Man  over a year ago

Guildford


"Wow"

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By *harliebluestockingsCouple  over a year ago

london

Keep going

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

More

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

The next morning Mel was awoken with a loud buzz. Picking up her mobile the screen illuminated reading "2 new messages."

Opening the message she was greeted with a image of Owens erect cock. Melissa's jaw dropped, in just a few hours she'd get another chance to wrap her lips around it. Throwing her phone on the bed she jumped up and rushed into the shower to get ready.

Putting on her Lacey white bra & panties with matching garter and stockings she texts Owen her address and kneeled waiting by the front door for her master to arrive.

As time passed the seconds felt like hours, her heart racing until, half an hour had passed and the door bell rang, impatient Melissa stands up and swings open the door "hello sir come in..." It wasn't Owen, but a much older man, well into his 40s stood there.

"Don't mind if I do Sissy, pushing Melissa to one side he walks in.

" So where is this happening then" he questioned as he stripped down to his underwear.

"I'm sorry who are..." Before Melissa could finish her eyes met with a large pulsing buldge in the strangers boxers. "Dave." He replied. "Mate of Owen's, said you were a right naughty sissy.

Grabbing Melissa by the wrist gently pulls her up onto her feet, before tugging her close and putting down a kiss, his hands caressing her back, making their way down to her lace covered kiss before squeezing it hard.

Overcome, Melissa begins returning the kiss before leading him into the living room, offering a seat and kneeling in front of him as she did for Owen the following day. Freeing his cock Melissa reaches for it but hesitates, remembering what Owen told her the following day not to use her hands. Wrapping her lips around Dave's hard cock she begins to suck, it wasn't as big as Owen's so was easier to fit in her mouth, she took it deeper and deeper and deeper into her mouth until she had reached the base looking up at Dave for approval, she was greeted with the face of a man enjoying himself.

Feeling proud Melissa went to get off his cock, went his hand landed on the back of her head, "your not finished yet sissy, your man's not finished. Owen hasn't trained you very well." He began guiding her mouth up and down his cock, faster and faster until he he was fucking her mouth.

"Mmmmm yeah, what a good slut. Keep going, Daddy.is.almost...ahhhhhh" he came shooting down the back of Melissa's throat. She gagged, looking up to say thank you, when she saw Dave was holding his phone in his free hand, camera pointed at her.

"Well Sissy, shall we take it upstairs for round 2?";he said standing up not waiting for a response he left the room.

Melissa sat thinking that she should be angry at Owen for sending him and for him filming her. But all she felt was happy, she felt like the slut she was born to be...

"Hurry up sissy I've already found the bedroom!"

Scrambling to her feet Melissa calls back "coming Daddy!" As she ran after the voice.

Just then the front door swung shut pulled by the wind...

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

Loving it

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By *r 007Man  over a year ago

harrogate

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

Amazing

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By *us man1957Man  over a year ago

Guildford


"Amazing "
more please

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

Keep it going x

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By *luttyzoeTV/TS  over a year ago

Lutterworth

Like it

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By *d funMan  over a year ago

Telford

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By *imale38Man  over a year ago

Barnsley

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By *asmin999jmTV/TS  over a year ago

wakefield

Wow xx

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

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By *iceandtightMan  over a year ago

Aberdeen

WOW

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By *r 007Man  over a year ago

harrogate

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By *es for funMan  over a year ago

port talbot

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