Musings of a Switch

Unfiltered thoughts from a bisexual switch

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Masturbation thoughts

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What do you think about when you masturbate?

Cartoon image of a man lying on his back. He is wearing a butt plug with a blue jewel. There is a cock ring around his cock and balls. He has his cock in one hand, and is dripping lubricant onto his exposed cock head with his other hand.
Cocktails and cock-stroking by Girl on the Net

This is not a question that comes to mind often. Most of the time the thoughts passing through my mind during masturbation are whatever turns me on in that moment. I have not noticed a trend of thoughts where one of them sticks out more than any others.

Most recently, my thoughts have been drawn to transwomen. The idea of sucking on their girl cock/clit really gets my thoughts flowing, and often leads me to stroking my cock until it is hard and ready to ejaculate my warm, sticky cum.

Previously I have been drawn towards women who have undergone significant weight loss and have excess skin with texture, particularly around their waist and fupa. Not really sure where those thoughts originated.

Other times it is when I am feeling submissive. Times when I want a woman to take charge of my orgasms and control them, even controlling my boy pussy. Have her peg me, even with fantasy dildos.

My mind wanders to any number of things when it comes to masturbation. They are generally drawn to my thoughts of the month and what is currently turning me on, and driving my sexual desires.

I wonder where my masturbation thoughts will lead me next.

Matthew meets Jamie

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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.

In the moment

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Right now, I have been watching some amateur porn with people watching fantasy dildos. Watching this porn stirs something deep inside me. I tweeted about it of course.

Now it does not matter whether the person has a vulva or a penis, I wish it is me riding that fantasy dildo enjoying the moment.

I’m not suggesting I wish to have a vulva of my own, but in the moment I wish I have one to enjoy the sensation of being penetrated with a large fantasy dildo.

Christina and John – Part 2

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After Christina left John stunned from using his mouth and tongue to orgasm, John collapsed on the lounge with his hard, lonely cock.

John stroked his cock a few times, but even with the desire to get off, he wanted to do it with Christina present. His cock lost it’s hardness, and John just sat there reliving the last few minutes over and over in his head.

Christina on the other hand smirked as she left the lounge room and headed to their bedroom. She grabbed her phone on the way and lay down on the bed with her phone.

Christina lowered her hand to her wet cunt. She explored every part of her wet cunt with her fingers, occasionally brushing over her clit. After the orgasm from John, her senses were heightened to every touch on her skin.

She took her phone and opened the camera app. She took some photos of different parts of her body, from her face to her toes. She took her time taking photos of her cunt, from it’s natural appearance, to it stuffed with as many fingers as possible.

Christina selected a few of the photos, and sent them to John. After sending them, she pulled out some toys from the bedside drawers and lay them out on the bed.

Christina lay back, grabbing one of the vibrators. She placed it on her wet cunt and turned it on. She started working the vibrator over her cunt, taking her time when the vibrator was near her clit. Moans escaped her lips and an orgasm started building deep inside her.

Still sitting on the lounge, John looked at his phone and saw the pictures from Christina. His cock slowly hardened and he started stroking himself.

This weekend was certainly different, Christina rarely sent him naked pics of herself. John stood up, with his cock in hand, and headed to their bedroom.

Christina continued moaning as she played with her toy. She was hoping John would come in and take charge and fuck her like she desperately wanted. Her moans turned into groaning John’s name.

John could hear Christina’s moans increasing in volume & intensity as he moved closer to their bedroom. His cock tightened as he heard her moans.

John continued to the bedroom, pushed the door open and peeked inside. He saw the toys on the bed, but no sign of Christina. Her moans were coming from the ensuite.

John positioned himself on the bed, naked of course, his hard cock in one hand, stroking himself. The ensuite door opened and Christina was perched on the vanity. Her legs spread, the vibrator deep in her cunt. She was fucking herself with her vibrator.

They could see each other pleasuring themselves. The room soon filled with moaning and groaning from each of them, edging themselves, keeping themselves on the edge of an orgasm.

The moans continued, soon John couldn’t take it any longer. He touched the head of his cock causing an eruption of cum from his cock. He lost sense of control with each shot of cum. His sticky cum all over his belly and chest.

John just lay there, warm cum all over his body, Christina still fucking her cunt. She saw the cum erupting from John’s cock. She removed the vibrator and jumped onto the bed. Christina wanted John’s cum. She wanted to taste it. She kissed his body, licking up the sticky cum, savouring the taste on her tongue.

Christina licked all the cum off John’s body. Once she was done, she took John’s cock in her mouth, sucking the last few drops of cum from his now flaccid cock.

Christina lay down next to John, pushing close to his body. Her mind wandered to the recent events. She had been hoping the pics would get John hard and ready for her to ride his cock & fill her cunt with his cum, but what she got was much hotter. She enjoyed watching John make himself cum. Tasting his cum from his body, listening to his moans as he shot his load of cum all over himself.

John and Christina just lay there in each other’s presence, satisfied with their orgasms and how they unfolded this morning. The start to their weekend couldn’t get any better.

Christina & John – Part 1
Christina & John – Part 3