Musings of a Switch

Unfiltered thoughts from a bisexual switch

Writing

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.

Christina and John – Part 3

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After Christina had devoured John’s cum from his body, she knew that it would be a little while until his cock was ready for her to ride. So as they were curled up on the bed, she plotted the next part of their weekend.

As all the events so far this morning had Christina leading the way, she wondered how far she could push John.

Christina fell asleep after the morning events. John hugs her for a few minutes as she drifts off to sleep. He got up, and does a few things around the house while Christina has a late morning nap.

About an hour later or so, Christina stirs. She can hear John doing some yard work outside. While John iss outside, she gets up and grabs a few toys & accessories from around the bedroom and lays them out on the bed.

Christina sets out her leather flogger, a glass butt plug, some faux leather cuffs and a small bottle of lube.

Christina lays down on the bed again. She hears John finishing up with the yard work, and starts touching herself again. Her mind wanders as she lets her fingers explore her body.

She imagines taking charge of her husband, owning him temporarily, making him her personal sex toy for the rest of the day. She tells herself that she will make it happen today.

Christina hears John come back inside, she continues touching herself as his footsteps get closer to their bedroom. John opens the bedroom door to see Christina touching her glistening pussy.

He quickly undresses and rushes over to the bed. Christina closes her legs, and wags her finger at John telling him ‘no’. John stands up with a perplexing look on his face.

Christina points her finger at the ensuite. John knows he needs to shower before the fun can continue. He has a shower to remove the grim & grit clinging to his sweaty body.

Christina goes back to touching herself. She moans with pleasure loudly so John can hear over the running water. John quickly washes himself as he listens to her moans. He jumps out of the shower and stands in the doorway watching and listening to Christina as she continues touching herself.

Once dry, John walks over to the bed and sees the toys laid out for the first time. He imagines he will get to use these on Christina, but does not know her plans.

Christina motions for him to join her on the bed. He crawls across the bed between her legs as she parts them further inviting John to eat her pussy.

As he gets closer, she pushes his head back away. He tries to lean in closer and Christina pushes his face away from her moist cunt. She pushes his face into the bed and stands over John.

She walks over the bed, leans down and grabs the flogger. She drags the straps along John’s back. He turns his head to look back at her. She smiles wryly at him, as her plan is starting to come together.

Christina stands on the floor next to the bed, she grabs John’s hair and pulls him to the floor at the foot of the bed. She holds the flogger close to John’s arse, the tails resting in his butt crack.

John’s cock starts growing as it dangles between his legs. Christina sees this and knows they will both enjoy her plans as John will be a willing participant.

Christina grabs the lube and butt plug. She rests the plug in the small of John’s back. The coolness sends a shiver along his spine. Christina drops the flogger to the floor, she opens the lube bottle lid and drips some into John’s butt crack.

Christina uses her fingers to spread the lube and warm it up. Her fingertip press against his asshole. John clenches as he has not been touched there in some time. Christina takes her time, adding a few more drops every minute or so.

She presses her finger against John, and the tip slips inside. John moans. He clenches around her finger, but wants more inside him.

John pushes back against Christina’s finger, begging for more without saying a word. Christina knows he is ready for her entire finger. She pushes her finger inside him slowly stretching his asshole. She rotates her hand so she can touch his prostate.

John shivers as she touches his P-spot. She strokes it a couple of times, and John groans loudly. She moves her finger in and out a couple of times finger fucking his ass. She feels his asshole loosen around her, she knows he is ready.

She withdraws her finger and grabs the plug. She slathers the plug in lube, and adds some more to John’s but crack. She then presses the tip of the plug against John and lets him guide how much he can handle.

He pushes back, then stops, slowly stretching himself to the size of the plug. Lube is everywhere but neither Christina nor John care. John wants that full feeling, and Christina wants a submissive anal slut of her own in John.

After a few minutes, the plug pops inside John and he moans in pleasure as the plug presses against his P-spot. Christina lets the plus find its resting place before pressing against the plug a few times causing the plug to move around inside John.

Christina has succeeded with part one of her afternoon plan. Christina grabs their play towel & wipes the excess lube off her hands and John’s butt crack.

She stands up and grabs the flogger again. She drags the flogger tails all over John’s bottom and back. Shivers run along his spine.

Christina is new to the flogger, so she starts slow. One stroke on John’s behind, then she drags the trails along his back. She strikes John again, over and over, each one slightly stronger than the last. John’s moans grow in intensity.

The flogging goes on for a good 10 minutes or so, with a couple of seconds between each stroke. Christina works up and down John’s thighs, over his arse and along his back. John moans loudly with each stroke.

Christina drops the flogger, and climbs onto the bed. She lays back, and props herself up on some pillows. She spreads her legs, and touches her wet cunt. She wants John to give her an orgasm using his mouth alone. She motions for John to join her on the bed, the but plug still in place.

She invites John to lick her wet pussy. She is already on edge and ready to cum hard. She pushes John’s face against her cunt. He runs his tongue along her pussy lips. John wants to give Christina exactly what she wants. He eagerly laps at her pussy and her legs tremble every time his tongue brushes her clit.

Christina pinches her nipples as John continues feasting on her cunt. She moans in pleasure with each pinch of her nipples. John places his hands on her thighs pushing them as wide as he can. He wants to get his tongue as deep as possible and gets her juices all over his face.

John senses Christina is on edge, he continues working his tongue and lips all over Christina’s vulva. Her leg trembling increases in intensity, her breathing gets shallower and faster, her orgasm builds deep inside her. John eagerly continues lapping at her cunt.

An orgasm erupts from deep inside Christina. She squirts all over John’s face. He savours the moment and enjoys the taste of Christina’s cum. Christina pants as her orgasm subsides. She has not had an orgasm from oral alone for some time. She looks forward to being serviced some more maybe later this evening.

John gets exactly what he wants, a face full of Christina’s cum. Christina gets her submissive anal slut, her husband, plugged and eager to please.

Christina & John – Part 2

Sarah & William

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Sarah arrives home from work. She heads to the bedroom, and kicks off her heels as she flops on the bed after a long day at work. William is in the shower himself, and does not notice Sarah arrive home. He turns off the shower, and as he opens the door, Sarah is standing in the doorway, naked.

Seeing Sarah standing there, William turns on the shower, and motions for Sarah to join him. She slowly moves towards the shower, swaying her body teasingly.

Sarah and William shower together. William takes his time, soaping up Sarah’s body, washing every curve and crevice of her body. He pays special attention to Sarah’s nipples, and her clit. She moans with each touch and tease from William.

Soon the teasing finishes, and they both get out of the shower and dry off.

As they enter the bedroom, William grabs Sarah’s ass, kisses her neck. He whispers into her ear, “pick a pair of sexy heels, I want to show you who your daddy is.”

Sarah grabs her favourite pair of playtime heels. She sits on the bed, then slowly pulls them on seductively in front of William. He watches on, his cock getting hard. He wants to ravish Sarah, he knows the time will arrive, but he continues to enjoy the show from Sarah.

Sarah spreads her legs, her hands covering her pussy. She flashes William before hiding her pussy again. Williams eyes grow, and he watches Sarah intently.

The sexual tension builds in the room, William takes control of the bedroom. He orders Sarah to kneel on the bed, her arse high in the air. William drags his fingers all over Sarah’s back. From her shoulders, over her arse, and down the back of her thighs. She wiggles and jiggles her arse.

William continues, leaning forward, kissing along her spine. He kisses all around Sarah’s arse, making sure to occasionally leave a little bite mark on her meaty areas. He kneels behind Sarah, spreads her arse cheeks exposing her pussy lips. He leans forward, taking a deep breath before leaning in and kissing Sarah’s pussy lips.

His tongue slips through his lips, and licks along Sarah’s moist pussy lips. A moan escapes from Sarah’s lips. William takes his time, licking and kissing, His fingers dragging along Sarah’s legs from her heels to her arse. Sarah continues to moan and groan.

William stands and goes to the bedside table. He pulls out a butt plug and lube. He kneels behind Sarah again, he rubs some lube over Sarah’s anus and the plug. He places the plug against her anus, and slowly pushes on the plug. He takes his time working the plug inside Sarah. She groans as she is slowly stretched open. Sarah squeezes against the plug, and they push against each other until it finally pops inside Sarah’s anus.

William admires the crystal plug glistening in the afternoon light. He slaps Sarah’s ass. She squeals in delight at the playful nature of William.

William tells Sarah to lay on her back and spread her legs. William positions himself between Sarah’s legs. He leans forward again and kisses Sarah’s pussy lips. He takes his time licking along her lips from back to front. Then focuses on her clit. His hands press the plug as he feasts on her pussy. Sarah’s moans get louder and louder.

She rests her heels on Williams back. The pressure from the heels triggers William to work his tongue and fingers harder and faster on her pussy. William continues licking, and sucking on her pussy. When William hits one of Sarah’s sensitive areas, she groans and presses her heels deeper into William’s back. This goes on for quite some time. The masochist in William desires to feel the pain, which drives him to eat Sarah’s pussy harder and faster.

William stops feasting, he looks up at Sarah. Sarah looks down at William with a look on her face that says, “why did you stop?” They look at each other in silence.

William rises to his knees. He grabs his hard, pierced cock, and starts stroking himself. Slowly at first, slowly exposing and hiding his piercing from Sarah’s eyes. Sarah’s eyes widen. She loves playing with William’s piercing. She sits up and reaches out to grab his cock, but he brushes her hand away.

Sarah pouts, she wants to hold William’s hard cock & piercing. She loves to lick along his shaft, teasing the pierced head with her tongue, but William stops her. He continues stroking his hard cock. The head glistens with precum.

As William continues stroking himself, Sarah feels the need to touch herself, but as her fingers get close to touching herself, William swats them away. William does not want Sarah to orgasm now.

Sarah continues trying to touch herself, but William always swats her hand away just as she gets close. Sarah looks at William with a look of disapproval. William just looks back with a wry smile on his face.

William stands & grabs Sarah’s wand from the dresser. He joins her on the bed again, but kneels near her head. Sarah tries to lick his cock but it is just out of reach.

William drags the wand from Sarah’s breasts down to her thighs and over her body, skipping her vulva. He continues all over her belly & thighs.

William spreads Sarah’s legs wide open. Her vulva glistening with his saliva and her juices mixed together. He places the wand on her labia & Sarah groans ecstatically. After William licked her close to many orgasms, she needs to cum. The wand would send her over the edge, but William wants her whimpering, wants to hear her beg to orgasm.

William lowers the intensity of the wand. He knows Sarah is close to cumming, but he wants to tease our a long orgasm from her. However William knows how to draw an orgasm from deep within Sarah.

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

Kissing date

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TW: The following story may contain topics that some readers find sensitive. All persons mentioned are of legal age and are able to give informed consent.

Sometimes the best stories come from real life scenarios and the possibilities that may develop from the situation. This is one of those events.

I am a prolific poster on Reddit & some of the more NSFW Subreddits where people, mostly women share their bodies with many subscribers from around the world. I am using Reddit at the moment to look for a little girl as part of a Daddy Dom Little girl (DDlg) dynamic, online or in real life.

At least once per week, I post up a personals ad offering to be a Daddy for Littles online or IRL. Most people who reply are from overseas. Now and then I come across someone from the land of Australia, mostly from states other than my home state.

Today, a lovely lady who goes by the name Olivia, asked if I could answer a few questions for her about DDlg. We had a good conversation via Reddit chat, and I cleared up some of her confusions and I answered questions to the best of my continually learning knowledge-bank.

After a few more days of chatting, we agreed to meet in person. This first meeting would involve a picnic and to eliminate any expectations of how the date would end, we agreed to partake in a ‘kissing date‘.

We organised to meet at the botanic gardens for a lovely picnic of sandwiches and champagne. I made some sandwiches that morning to bring with me. I packed a picnic blanket ready for our date, as well as champagne flutes. Olivia agreed to bring her favourite champagne for us to drink.

We travelled separately to our date. I arrived first and setup the blanket for us under the shade of a large tree. I pulled out the plates, sandwiches and champagne flutes ready for the date. Olivia arrived a few minutes later and brought over the champagne for us.

We did the polite thing with a cheek kiss and sat down on the blanket. We chatted for a few minutes, we were already comfortable chatting, but being in person made things a little awkward at first, but we soon found our chatting rhythm.

I offered to open the champagne. I took the bottle, and slowly worked out the cork with the familiar pop. I poured out two glasses of champagne for us. I set the bottle down, and we celebrated our first meeting.

It was time for some food, I offered Olivia the sandwiches, and she took a few to nibble on, but I sensed the food would only be the appetiser.

Olivia put her sandwiches to the side, and she jumped on top of me pushing me to the ground. She leaned in and kissed me passionately. I returned the kiss, we just lay there for a few minutes continually kissing. I hugged Olivia and pulled her body close to mine.

We rolled over so I was on top. The kissing continued of course, and the tension was slowly building. Olivia’s hands started to wander all over my body.

Olivia reached down between us & rubbed my cock through my jeans. I ignored her advances & continued the kissing.

We positioned ourselves side by side to continue kissing each other. Our hands were enthusiastically exploring each other’s curves & crevices.

Olivia mentioned she wanted to see my pierced cock in person as she had never seen one up close. She reached down and tried to slide her hand inside my jeans. I grabbed her wrist playfully and pulled her hand out. She tried again and I pulled her wrist back out again.

We continued kissing enjoying the taste of each other’s lips. Olivia reached down again & rubbed my hardening cock through my jeans again. I moaned at her touch. I wanted her to touch it but we agreed to a kissing only date.

I rubbed her cunt through her dress and panties. I could feel her warmth and knew she was wet, but I resisted lifting her dress for a closer inspection. I really wanted to touch her cunt and taste her juices, just as she wanted to taste & feel my cock in her mouth.

The kissing subsided for a bit to catch our breath. We were both hot and horny for each other, but knew we agreed to limits. We could have changed those limits, but what would we do next time?

We finished up the last of the champagne and sandwiches sitting on the blanket just talking.

Soon the time allocated came to the close, we still wanted each other, & knew this relationship could go further than we initially thought back during those first few messages on Reddit.

We packed up & wandered back to the cars, hand in hand, giddy with excitement over what just happened and what may happen in the future.