anal

Matthew & Jamie matched through an online dating app. Neither knew exactly what they were looking for on the app, but they each had ideas of what they were looking for.

Matthew is a masculine presenting guy, looking to finally settle down with someone, but willing to hookup if there is some sexual chemistry but not enough to consider settling down with someone.

Jamie is a transwoman who has been undergoing transition for quite some time. She has had top surgery & is saving up for additional surgery. She is looking to settle down herself.

After chatting for a few days over the phone, they agreed that there was enough chemistry for a date or two to see if there was more than just messaging & phone call chemistry.

They agreed to drinks & dinner at a harbourside pub on a Thursday evening after work. Matthew arrived first, grabbed himself a drink, and found a fairly quiet corner overlooking the harbour. Jamie arrived about 10 minutes later as Matthew was about to finish his drink.

Jamie sat down and Matthew offers to grab a round of drinks for them. He leaves Jamie alone while he gets some drinks & brings them back to the table.

Matthew & Jamie chat their way through a number of topics through the early evening as the sun sets. There is certainly some in-person chemistry as the flirting between the two of them escalates to touching and kissing.

Jamie’s stomach rumbles in hunger and she suggests they grab some food. Matthew’s place is a 10 minute walk away, and he knows a nice little restaurant they can pick up some food, and take it back to his place.

Jamie agrees, and something stirs deep inside her.

They walk to Matthew’s place and continue flirting with each other. As much as Jamie was hungry for food, her desire to eat Matthew was growing. They pick up the food and they head to Matthew’s apartment on the 34th floor.

Matthew drops the food on the table, Jamie takes off her heels and wanders over to the window to see the view from Matthew’s apartment. The night skyline looks amazing as naughty thoughts cross her mind.

She turns to see Matthew right behind her, she grabs his face and kisses him. Throws of lust engulf them.

Their hands explore each others bodies, pushing each others clothes to the side and casting them across the room. Soon Matthew is just in boxers, and Jamie in her bra and panties.

Matthew looks down and can see Jamie’s girlcock bulging in her panties. He has never been intimate with a transwoman, however things felt right with Jamie.

The strong masculine Matthew kneels before Jamie. He helps Jamie remove her panties, and he takes her girlcock into his mouth. He licks and sucks on her girlcock just as he does with any clitoris has has before. Jamie moans in pleasure as her girlcock hardens.

Jamie grabs Matthew’s head and helps guide him to lick and suck her girlcock just as she wants. She takes a step towards the lounge and Matthew follows on his knees. Jamie sits down and spreads her legs. Matthew continues sucking enthusiastically on her girlcock.

Sitting down, Jamie can relax and lets the waves of pleasure flow over her body. Her moans grow louder the longer Matthew continues sucking on her girlcock.

Jamie feels an orgasm building deep inside her. She is unsure how Matthew will handle a mouthful of cum. She lifts his head and kisses him deeply. She pulls back and tells Matthew she is close to cumming. Matthew does not care, he is enjoying his first time with Jamie. Her moans are like hypnosis to him.

Matthew takes Jamie’s girlcock back in his mouth and wants to make Jamie cum for him. Matthew has never made another cock cum, so he was determined to make Jamie’s girlcock cum. He puts all his attention onto her girlcock.

Her moans intensify and they drive Matthew wild. Jamie lets him know she is about to cum and Matthew eagerly continues sucking. Jamie shoots a load of cum into Matthew’s mouth. He doesn’t even flinch. He swallows Jamie’s cum as if he has sucked lots of cock before. (It helps that Jamie’s load is reduced by her Testosterone suppressor)

Jamie lays back panting, catching her breath. She hasn’t had an orgasm like that in quite sometime, much less from a masculine guy like Matthew. Most guys like Matthew she has met are turned off when they find out she is a transwoman.

Matthew looks up at Jamie, a small drop of her cum leaks from his lips. He smiles proudly, full of joy from giving his first blowjob on a girlcock.

Matthew is eager to go again. But he suspects Jamie’s orgasm would be similar to him requiring a break between them. Jamie confirms this is the case.