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Ashley's Femside (A NSFW Commission)
🕑 Added 2025-09-23 13:42:44 +0000 UTCHere's Ashley's femside - Written from the Girlfriends POV she allows her BF to transfor into a woman and experiance his first female Orgasm
( I don't do NSFW naughty stuff much these days... so enjoy this naughty one)
Ashley's Femside
My thoughts are running in circles about what I found last night. I’ve been thinking about it all day, and that’s why I find myself staring at the cafeteria floor.
Then a shadow cut across my feet. I look up, and there’s Gina, my best friend at work, staring down at me like I’m a lost puppy.
“What?” I ask, looking away as she thrusts a coffee cup at my chest
I take hold of the warm coffee, and she sits opposite me. I can tell she wants to know what’s bothering me, but I’m just not sure it’s my place to share.
“So, Brittany…” She sips her drink and leans forward with interest. “What’s going on with you today. You’ve been in a world of your own.”
“It’s nothing….” I stare off into the distance as I sip my coffee.
“My girl’s been silent all day and hasn’t even complained once…” Gina chuckles, flicking a sugar packet at me to get my attention. “Something’s up, and you’re going to tell me. I can’t stand you being so… so… mopey.”
“Oh shut up….?” I throw her a dirty glare. “I haven’t been ‘mopey!’”
I can actually hear Gina rolling her eyes.
“Someone’s on their—”
“I am not on my period!” I shout, louder than I actually wanted to, drawing everyone’s attention my way.
I can’t believe that just came out of my mouth. Heat rushes to my cheeks as I catch my boss’s stare. I jerk my gaze to Gina instead, praying the ground will swallow me before anyone else notices.
“Girl….” Gina giggles to herself as we both go red in the face. “Come on. Tell me. Is it something to do with Ashley? Is he being weird again?”
“Y-yeah….kinda about Ashley,” I admit, making myself smaller as I curl hunch down. “I shouldn’t tell you, Gina. It’s kinda personal.”
“Don’t tell me you found his special sock.” Gina gags theatrically, her lip curling. “Boys are so gross.”
“No…not that,” I shake my head.
I scan the cafeteria, making sure no one’s close enough to hear. When I’m certain, I lean in toward Gina and lower my voice.
“I find some….. pictures…..”
“Pictures?” Gina hides a gasp behind her hand. “He’s cheating….?”
“Noo….” I check once again that no one is listening. “I found pictures of him….dressed in my underwear and my clothes. I-I…I think he might be a….. crossdresser.”
I brace myself, eyes squeezed shut, waiting for Gina’s laugh to shatter our little secret. But the silence stretches. When I finally open my eyes, she’s watching me with a cheeky grin instead.
“Y-You’re not going to make fun?”
Gina tilts her head before reaching across to pat me on the head.
“No, sweetheart.”
She then starts to rummage through her purse, looking for something.
“Y’know….the whole crossdressing thing is pretty normal…” she looks at me with a soft smile. “I’ve been with a few guys now that are like that. They tend to be very soft and gentle lovers….and very loyal.”
Then, from her bag, she produces a small card and slides it across the table toward me. She holds her hands over the face of it, hiding the majority of it from view.
“Now, before I show you this, are you interested in exploring that side of Ashley, or is his crossdressing a deal breaker?”
I can’t help switching my glance between the card she conceals and the sharp seriousness in her eyes.
“I….um…” I shrug with indifference. “It’s not his crossdressing that bothers me. I’m Bisexual anyway, it’s just the fact he’s kept it secret from me all this time. We’re supposed to trust each other.”
Gina looks at me like I’ve shared too much.
“Girl,” she sighs, rolling her eyes. “I’m not asking for your whole life story. I just wanna know if you’ll like him…..as a woman.”
My eyes widen, and I give it a moment's thought
“I guess….I guess so, yeah. Why?”
“Here….” She takes her hand off the card to reveal it to me. “Take this home tonight. Thank me later, yeah?”
Later that evening, after I get home….
Card still clutched in my hand, I close the front door behind me.
My stomach twists.
What if Ashley hates what I’m about to say? Still, I want him to know I see this part of him. If that means admitting I'm aware of his crossdressing, then so be it.
“Ashley….” I call out, sliding off my heels and hanging up my coat. “I’m home.”
He calls from the living room, and I step inside. He’s on the sofa, eyes on the TV. I notice right away that he’s shaved off his beard. He looks years younger, and, somehow, a little slimmer too.
I wonder if he’s shaved because he dressed up today?
My curious gaze leads him to smile awkwardly at me. “Brittany?” he says, looking worried. “Are you okay?”
“Y-Yeah…” I forced a smile, hiding the card Gina gave me behind my back. “H-H…Have you had a nice day?”
I can barely hear his words in reply. My heart hammers so hard it feels like someone’s drumming inside my skull. I just nod as he talks, my mind racing with how I’ll even begin to bring up his crossdressing.
Gina seems to think it’s not a big deal, yet he’s hiding it from me. Why?
“Brit?” he says, snapping me out of thought.
“T-That’s nice…” I nod, just standing awkwardly in the middle of the room.
“Nice?” he looks at me, confused. “My friend's cat just died. How is that nice?”
“Oh….” frazzled, I go bright red. “I…I…. It’s nice because…”
I can’t think of a single thing to say. And now he looks like an innocent schoolboy, all clean-shaven, his big, doughy eyes making everything even harder!
I let out a long sigh and lower my head. “Sorry, Ash. I wasn’t listening. I… have something I want to ask you.”
I feel Ashley’s worried, yet curious eyes burning through me. I can’t bring myself to say it. Suddenly, the words in my mouth feel like lead!
“Brit?” Ashley reaches for my hand. “Are you okay. Did something happen at work?”
I look down at him, biting my bottom lip with tears misting my eyes. I love this dofus, so why can’t I bring it up? We’ll be closer as a couple if I get him to talk about his crossdressing…I know it!”
“No… not exactly,” I say, still hiding my hands.
“Are you hiding something?”
“Ashley!” I shake my head harder, and my hair flicks in my eyes. “Just listen!”
“S-Sure…” he sits back waiting for me to speak, but I can see he’s also starting to panic.
He’s fiddling with his thumbs and going bright red!
Wait, does he think I’ve found out and I’m about to tell him off? No…. I’m not mad at him! Not mad at all!
Actually, I think this makes him more interesting, so why does he look so worried? Does he think I’m going to leave him because of it!?
“Y-Y….You’re going to break up with me, aren’t you?” Ashley asks, his voice barely a whisper as I watch him cover his face with his hands.
“What?”
“I’m sorry, Brit.” He grips his hair, frustrated. “I-I’m not a weirdo, I promise. I… I don’t know why I like girls’ clothes. I’m really sorry you saw those pictures. I… totally forgot to turn the PC off after dressing, and I didn’t mean for you to see them!”
I’m stunned. I can’t believe he actually thinks I’d leave him for that.
“Ashley…” I gasp, my breath uneven.
“Sorry, Brit!” He interrupts me. “I’ll pack my things and go back to my Dad’s. S-S..Sorry again.”
“Will you fuck…” I blurt in a moment of pure honesty. “I’m not mad. I don’t think any differently of you. Actually, I’m curious to find out more… so you can drop this whole ‘I’m going back to my dad’s’ crap, okay?”
Flabbergasted, Ashley looks up at me from the sofa, his face drowning with tears. The look on his face is one of utter disbelief. I’m actually a little offended he didn’t trust me.
“Don’t look at me like that,” I chuckle, brushing the hair from my eyes. “I’m honestly a little sad you felt you couldn’t share this with me. I wasn’t joking when I said I love you, Ashley. I want to know everything about you!”
“R-R….Really!?” he replies, wiping away his tears.
I nod, and sensing the moment is right, I thrust the card Gina gave me toward him. I hold it steady, showing him the face of the card, but I can’t help shivering with worry that he’ll think I’m taking this too far.
Furrowing his brow and sniffing back the tears, he glances at the card and then up at me, confused.
“A Uno card?” he asks.
I nod
“Why?” he looks closer at it. “It’s got the transgender flag colors. Did you get this for me?”
“Well, kinda…” I answer, nervous. “Gina gave it to me. Apparently, it’s all the rage on TikTok. The person holding this card… they can reverse their opponent’s gender…”
Ashley leans back slightly; his eyebrows show skepticism. “Are you serious. I’ve seen posts about these on my crossdressing forums.”
“Gina seems to think it’ll work,” I answer with breathing a sigh of relief that he isn’t getting angry at me for sharing his crossdressing with Gina.
Still shaking, I get to my knees in front of him and lean on his legs, looking up at his big blue eyes. I smile and gently touch his cheeks. “Do you want to know how it feels to be a girl, Ashley? Is that something you want to know?”
He holds my hand that touches his cheek, but he bites his lip.
“I’m sorry I never told you about her.”
“Her?”
“My female side.” Ashley clarifies, still holding my hand. “Until recently, I always just assumed I’m broken goods. It’s not normal for a boy to want to be a girl, right?”
“What is normal…?” I answer flippantly, before moving my face closer to give him a gentle kiss. “I want to meet her, and with this card, we can meet her together, for real.”
Ashley is hesitant to kiss me back. He turns his face slightly away, making me stop.
“What's wrong?”
He only manages to glance in my direction before looking away.
“It’s real sweet you're doing this for me, Brittany…but what if my being a girl freaks you out. You're with me because I’m a boy and you're straight, right? Do you really wanna kiss a girl?”
I wait for him to look at me, and when he does, I steal a kiss.
“If that girl is you….” I say, pulling back just enough to talk. “Then yes, I want to kiss her.”
Almost as if I’ve said exactly the right thing, Ashley presses a flurry of passionate kisses against my lips. When we finally part, I find her grinning at me like a Cheshire cat.
I then open out my hand and hold the Uno card in front of him. We both look at it as if it’s diamonds on a hardcore Minecraft world.
“Here….” I place it into one of his hands before standing. I flick back my hair and smile. “I’m going to go get changed out of my work stuff. If you wanna have….. a little fun. Use the card on yourself.”
I'm super curious to know if he’s going to use it, so I fight the urge to just stand and watch him transform. However, I do give him the courtesy of some privacy to think about it. I leave the room, head down the hallway to our bedroom, and start undressing.
I strip down to my underwear, ready to slip into my comfys, when a burst of commotion and high-pitched laughter echoes from the other room. The bedroom door swings open, and I’m still clutching the long denim skirt I was about to put on.
Standing in the doorway, a girl with bright pink hair and the biggest smile.
At first, I recoil, half-naked in front of what feels like a stranger. Then I meet her eyes, Ashley’s eyes, and my breath catches as I realize what a beauty he has become.
“A-Ashley?”
She flings out her hands and stares at herself. The fabric pinches in some places and hangs loose in others, struggling to contain the fuller curves of her new body.
“Y-Y….You did the switch!” I drop my skirt and rush toward her. “How do you feel!?”
Touching her new body, Ashley doesn’t say anything to me. I can see the buffering plastered across her face. It’s all new to her, and it’s happening all at once.
“I like this hair….” I reach up and touch her soft pink hair. “How come it’s pink?”
Ashley reaches up and pulls from the stands in front of her eyes. She tries hard to see the color before letting out a soft laugh. “This is amazing!” she declares. “I always thought that if I were a girl, I’d have pink hair!”
“It’s really cute.”
Still standing in the doorway, Ashley begins to frantically strip off her clothing. I just stand and watch as my boyfriends, soft, supple, and curvaceous body presents itself to me.
First, I notice her cute, toned stomach. Then her perky, bouncy breasts. I can’t tear my eyes away as more and more pale, smooth skin is revealed before me.
Before I know it, I’m standing face to face with my boyfriend's erect nipples pointing directly at me. I gasp with embarrassment as I sneak a quick look down to see his flat between her legs.
My boyfriend has a vagina….it’s nearly hairless and everything!
“Brittany!” Ashley squeaks out, grabbing his tits and squeezing them. “Look! I’m a girl! I’m a real-life girl! Holy shit!”
Incredibly aroused by the cute girl in front of me touching herself, I bite my bottom lip.
“My cock!” Ashley exclaims, reaching down to investigate, “It's gone and I’ve got a—”
She freezes, and I watch her face glow bright red.
“A vagina?” I ask, finishing the sentence. “How's it feel?”
“Kinda….” he begins to smirk. “Kinda gross, honestly. It’s all wet and flappy and stuff.”
I narrow my gaze, unimpressed.
“I’m just being honest!” she says, looking up at me from her bent-over position, having just sneaked a glance at herself. “It’s freaky, that’s for sure… but I’m really excited by this! Thank you, Brittany. How can I ever repay you for giving me this?”
My expression softens, and I shrug.
“You don’t need to pay me back, Ashley. I can see how much this means to you.” I hold my hand out for her to shake it. “Hello,” I say playfully. “I’m Brittany. It’s nice to finally meet you, Ashley’s fem side.”
Ashley takes my hand, gives it a shy little shake, and gently pulls me toward her. We’re the same height now, so our boobs press together as she hugs me softly. I loose in the battle of boob. Hers dominate in size and weight!
I giggle at the battle of our chests pressing together as Ashley gently lifts my chin and kisses me again and again, each one more passionate than the last.
“Well, hello…” I smile when she finally lets me catch my breath, though it feels like she was trying to eat my face.
“S-Sorry… I just really wanted to touch you and kiss you.” She giggles, fumbling to waft hair from out of her face.
Watching her struggle, I gently tuck the strands behind both her ears. Then I steal a quick kiss before resting my hands on her hips.
“Are you feeling….” I feel myself become excited. “…feeling….warm…down there, Ashley? Like an itch you really want me to scratch?”
“Exactly that!” she replies, wide-eyed and desperate. “How did you know!?”
“You’ve a lady boner.”
Ashley looks at me, puzzled, “How can I have a boner I don’t have a—”
“Ashley, I’m telling you you're ready for sex. Your vagina is all moist because it wants to be penetrated!”
“Urgh gross…” Ashley then blushes. “But yeah. I do want that. I want you.”
“Oh…. do you now?” I reply sarcastically. “Well, little missy…” I click my fingers and point at our bed. “You best lie on your back and spread those legs of yours.”
For a moment, Ashley just stares at me. I guess, for her, this is like playing a video game with all the wrong settings. She doesn’t know what to do with herself. Usually, when we’re about to have sex, Ashley pins me to the wall, but this time, it’s me demanding she give herself to me.
“You heard me!” I command with presence, reaching to her plump backside to give it a firm squeeze. “Get that on that bed and spread 'em, sexy girl…”
A flurry of expressions crosses Ashley’s face, a strange blend of terror and excitement I can’t quite untangle. I watch as she awkwardly straddles our bed, then eases onto her back. Her eyes find mine, and she gives me the sweetest, most innocent smile as she slowly parts her legs before me.
“Ash….” I can’t help but stare. “Your pussy is super cute.”
“Cute…” she asks, flinching a little as I get between her legs and kneel over her.
“Yeah,” I lean forward, grabbing her parted legs with my hand to steady myself as I give her a kiss. “I want to play with it. Is that okay?”
“Erm……”
I place a finger on her lips.
“I promise I’ll go slow, and if you want to stop, just let me know.”
Ashley’s cute eyes bulge, and she nods.
“Good girl.” I steal another kiss from her quivering lips, before kissing her neck, her shoulder, her nipples, her stomach, and then finally, I kiss her left inner thigh, working my way towards the heat emanating from her pussy.
I stop just short of kissing around her vagina lips.
I hold my mouth there, purposefully breathing on it as I talk.
“Ashley,” I say with purpose, holding her legs as she shivers from the feeling. “I’m going to touch you now. Are you ready?”
“I…I think so.”
She’s nervous, and that's understandable. So, I very gently kiss around her clitoris without touching it. I wait for her reaction before softly kissing again.
I never heard my boyfriend moan so much before. He’s usually so quiet. It spurs me on to be more adventurous, and as I work my way around his pussy lips, I stop for a moment before giving his clit a firm lick.
His body reacts with a judder and then a shiver. His girly voice moaning out as I give it a second, longer lick
“Like that, baby girl?” I tease, sitting up between his legs with my fingers playfully exploring.
“It’s sooo sensitive!” Ashley moans, throwing her head back onto he pillow in pleasure. “K-Keep going! I…I-I need more!”
Forming two fingers, I start rubbing his pussy from the clit down.
“Feels good, doesn’t it?” I ask, watching him squirm from my touch. “Now you know why I’m so desperate for you to touch me down there, Ashley.”
I keep going, faster and faster with my fingers.
“Feels good to be a woman, doesn’t it, Ash?”
“F-F…Fucking hell yeah!” Ashley bites her bottom lip hard, and her hands grab at the duvet. “I…I feel so… so like pent up. I feel like I want something to give me deep release. Is…Is that normal?”
I stop rubbing her clit, letting her calm down. I watch Ashley’s face tense up as I stop and just hold my fingers on her clit.
“Totally normal. Do you want me to continue?”
Ashley nods vigorously, and before she can say anything, I slowly glide my two fingers down into her pussy, sliding them inside her to feel how wet and warm she is. She jolts at the sensation of me penetrating her with my finger, but slowly begins to relax.
“You okay, babe? Should I have warned you I was going to do that?”
“I like it.” She responds, moving her hips in an attempt to thrust my fingers deeper inside. “It’s very different from what I’m used to, but it feels great!”
“Good…” I slide my fingers out from her pussy and glide them across her opening towards her clit. Now moist from her juices, I tickle her bean.
She moans louder, making me blush a little as I continue to massage her nubbin.
Spurred on by her vocal enthusiasm for what I’m doing, I keep going, enjoying how, for once in our relationship, I’m in control. She’s submissive to my every move!
Moan after moan, I keep going. I rub Ashley’s clit until she’s edging. I want to tease her more, but I also want Ashley to experience her first orgasm as a newly transformed woman.
“AHHHHH!” Ashley whines out in pleasure, her back arching as juices spurt from within.
“Hehehe…” I giggle, slowly sliding my fingers in deep as I feel her warm juices coat my finger. “Did you enjoy that?”
Breathing heavy, Ashley doesn’t answer.
I take my fingers from her vagina and lie next to her with my head on her arm. She turns to look at me and smiles as I look into her stunned, but thankful-looking eyes.
We kiss once, but it’s deep and passionate, like she understands me on a much higher level.
“You….” I poke her nose with my juiced fingers. “Just became a real woman.”
“I did?” she replies with a bashful grin.
“Yup!” I lick my fingers to tease her. “I like you as a woman. You’re tasty in so many ways.”
“Maybe….” Ashley kisses me before looking me deep in the eye. “Maybe I should stay this way?”
I stare back with the utmost curiosity
“You…. wanna stay a girl?” I ask.
Ashley turns away, head on the pillow, and looks up at the ceiling. A smile tugs at her lips as she reaches for her chest and squeezes her breasts.
“I think I do…” she admits and then turns her head to look at me. “Even this small taste of being a woman has convinced me. This is who I really am. I’m not a boy. I never have been, really.”
I watch as her smile fades into worry.
“I’m sorry, Brit.” She says with as I watch her sink into despair before my very eyes. “If you don’t want a girlfriend, I’d understand. But I don’t want to go back to being a boy. Now I’m a woman, all my dreams can come true.”
A single tear dribbles from her eye
“I still love you, Brit, but….” She wipes away her tears. “Would you still want me like this? Would you still want me as your girlfriend?”
I give it a moment’s thought.
“Ashley….?”
“Yeah?” she replies, looking at me
“Is that still you in that sexy woman’s body?”
She looks at me, bemused. “Y-Y…Yeah….”
“Then I still love you…..”
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Annah Rourke
In an ideal world The ending would never be different
