1 - My first kiss
I lean my chin on my hand as I look out of the cafe window. Thinking back about the past year. Maybe I should give my dad a call? Visit him? See if he’s still an asshole? Meh… That doesn’t need checking, he’ll never change.
Almost a year has passed since he kicked me out of the house. When he found the one skirt I owned back then he called me a crossdressing homo and told me I wasn’t his son anymore. That came as quite a shock at first. In the following fight he kicked me out of the house. For 3 days I was homeless with nowhere to go. Fortunately I have since been able to find a place to stay. I’m renting some guys' basement apartment. Nobody came looking for me either so I guess I got a fresh start at life.
I couldn’t find a job, so I’ve created an Onlyfans. I had my first follower within a day and every day more would sign up. At first I believed I was making a smart choice, but really I don’t enjoy the attention. However, the money it brings in enables my life and it allows me to indulge myself with my feminine side. I have a couple of outfits and consider myself to be a femboy.
Quite naturally so, too. I have a feminine waistline. I barely have any body hair. My slender body fits most medium sized women's clothing without it looking weird. And my pixie cut hair is very ‘gender neutral’. If I were to leave my home wearing a female outfit, I’m sure most people would think I’m actually a girl. I don’t do that though, that’s too scary.
Instead I take pictures of myself posing in women's clothes and sometimes dress up in simple anime outfits, cosplay I guess. It’s kinda cute, I like cute. In every photo I post I blur my face or wear a mask.
I’m on Reddit and Onlyfans every day, posting photos of myself. Nobody in real life knows what I do though. Likewise, nobody online knows who I really am. Seemingly overnight I gathered thousands of horny fans but I try really hard to stay anonymous.
I stare across the street at a young woman taking a picture of the cafe. She stares in my direction, I feel like we’re making eye contact. She then takes another photo and walks away. Oh how my life has changed, I went from a military regime to wearing girly outfits on the internet. I used to live with my dad on the air force base in Anchorage, Alaska. He is one of those hardliner military types. Salute the goddamn flag son! Be a man, boy! Sir, yes sir! I don’t think he ever wears anything else but his uniform. You know the type. I hated it there. My mom hated it too, she left years ago. I think she lives in Montana somewhere, we never talk though.
Without a real plan for the future I intend to quietly sit out my life in lonely peace. Well, maybe not lonely, I would love to find a likeminded person to be weird with. But I have no real hope of that ever happening. I’m not at all a social person.
So, back to the here and now. I glance at my phone, it’s time to go home. Lunch was good, I had tea and a cream cheese bagel. I like coming here to look at people. I often imagine someone would pay attention to me. Maybe one day I can finally meet someone fun and make a friend.
Yeah, uh-huh, like I know how to talk to people.
Anyway, while I gather my things a man walks up to my table. He has been sitting across the room with some other guys. I saw him look over several times but paid him no mind.
"Hi, what's your name?"
"Ehh, Fabian. Why?" I answer, looking awkwardly at him looking down on me. He looks like he’s not from around here.
"Oh, you’re a dude?” He looks surprised. Then louder so his friends can hear he continues, “Ehh, so I just thought I recognized you from somewhere."
"Oh… OK. Hi!" I reply with an awkward cutesy wave. I look up at him again and think he's in his mid-twenties. Kinda cute too. He has friendly, curious eyes. I think he’s taller than me. Not very muscular, but definitely someone who can take charge in an office.
"Yeah… I definitely saw you somewhere. Something about your hair." The man continues.
"Oh, OK… Maybe in town?" I feel like running away. I’m so socially awkward that I feel nervous and scared!
"No, not there. You're on Reddit, right?" He grins knowingly while he gestures at the empty seat next to me.
"Everyone is! So what if I am?" I'm on the defense now. He has a really keen eye for detail if he recognizes me by my hair.
The guy 'hmms' and sits next to me and bends over, whispering at me, “You look familiar to someone I follow there, a girl… For a moment I thought you’re her, so that’s what I told my friends. I still think you’re cute though.”
“I’m not her, obviously…” I hush back. Unless… Maybe he follows me on Reddit and thinks I’m that woman. I nervously glance at his cohorts who are all staring at us.
“Yeah, well. Hmm…” With a frown he looks the other way. Clearly some sort of impasse has been reached in his head.
“I’m going now… Because, I have to go.” I quietly say.
“Yeah…ok.” The guy looks disappointed at his introduction going all wrong and I continue leaving.
I get up and flinch, my chastity cage pinches me. I grimace and quickly sit back down. Looking around I see the man look at me with a vague curious smile.
“Yes?”
I ignore him and push on my skin around the chastity device to ease my burden. When I get up again there is no pain and I quickly head for the exit.
"Hey! You’re OK?"
I hear the man's voice behind me and laughter comes from his friends. Too embarrassed to respond, I focus on the door and say nothing as I make my escape. Assholes! I know they’re just having a bit of fun, but I'm so awkward around people that I can't deal with it. Maybe I'm the asshole. My penis stirs in the chastity cage and I glance down to make sure it's not showing. A slight bulge gives away that something is there, but I hope that no-one will notice it’s not just a penis down there.
When I’m halfway down the block I hear running footsteps and my left arm is grabbed from behind. I spin around on the spot and jerk to a halt and come face to face with the guy from the cafe.
“I’m Max, we should go out some time.”
“What!? Why?” I stare at him, then my arm, and back at him. He quickly lets go of me.
“I dunno… You look friendly, Fabian, right?”
“Yeah, but I’m still not a girl…” I counter. God this is so awkward.
“I know. It’s OK, I think. I just want to talk. Why did you sit back down?”
“What? I ehh, a cramp.” I blush at him.
“Right, here, hold up your phone?”
We bump our iPhones together and exchange contacts.
“Call me OK? I want to know about you.”
“Yeah, ehh… I live there…” I point down the street. Gosh, what am I doing? Why did I just do that? What does he want from me?
“Ok…” He looks uncertain.
“Sooo, yea!” I hush at him and turn and continue towards home. My head feels like it’s stuck in a pillow. Max confuses me. He’s gay or what? Does he think I am? Arriving home, I throw the door shut behind me and land on my bed with a giggle. Not all is lost for stupid me. Someone actually is attracted to me. A guy, mind you, but it’s something.
“Hey…” a voice from nearby.
I abruptly become quiet and look over my shoulder. There’s Max, on my doorstep. He holds the door open.
“Sorry, I followed you… You said to follow you, right?”
I shake my head no. Crawling off my bed I look into his nervous eyes, my own filled with fear.
“What do you want?”
“I don’t know. To talk to you, I guess. Is your girlfriend home?”
“My what?”
“There’s a skirt… There.” Max points at my couch.
‘Crap, now he will discover everything. Ridicule me, and…’ I interrupt my thoughts and look at him.
“No, she’s erm…” I start to say, “I’m single.”
“Oh, OK. So? Do you think uhm, we can eh, maybe we can have a chat?”
Our eyes meet and suddenly he lurches forward. He reaches up and holds my head in both hands and he presses his lips on mine. I step back and we fall onto the couch. Max crushes me under his weight. This time the door falls in its lock.
I struggle and fidget under him, turning my head away from his assault. “Help, what!? What are you doing?”
Max quickly gets off from me and sits on the floor, he stares at the big catgirl anime poster on the wall as if he recognizes it.
“I’m sorry… I don’t know what came over me.”
“Well figure it out! I’m not gay… I think.”
“You’re not sure?”
“Are you!? Geez!”
“Don’t tell anybody that.” Max hesitates. “Actually, I’m not gay, I just like guys that look feminine. Femboys, do you know what that is? I would love to meet one.”
“That’s gay!” I gasp. But I totally know what he means, I feel like that too sometimes. Worse, I am what he wants! Fuck! Am I gay too? Like actually? I turn my back to him to hide my embarrassment.
“I’ll leave, sorry about this!”
“Yeah, OK.” I whisper. My penis is so hard, it almost bursts from my cage, it hurts.
“Bye… Sorry again.” Max says. His hand gently brushes over my shoulder and he makes his escape. I hear the door shut and I’m alone.
What the fuck just happened!? I should go after him, right? But I don’t move. Home invasion, sexual assault, maybe? I should probably call the cops, but I don’t. Instead I smile at his stupid attempt to court me and kinda wish for more. Except he should be a woman. For over an hour I lie still on the couch, curled up and clinging to my pillow.
Days turn into weeks and I never see Max again. Every day the insane event becomes a more and more distant memory. I’m too scared to contact him. And he never calls me either. We’re such fools.
2 - Dating profile
When I’m done unpacking my groceries I sit down in front of my computer and log in to my dating profile. I’ve created it many months ago and regularly stare at the nearly empty profile.
Over the last year I've been telling myself that I either need the coolest girlfriend in the world, or a femboy friend. Even though I don't consider myself to be gay I think it would be fun to have a friend like that. Unfortunately I’m not at all confident enough to make either happen. But imagine, we could play Minecraft together, or watch anime all day or something. Maybe dress up and just understand each other like that, it’ll be so cool!
In the profile I’ve uploaded two pictures, one where I’m wearing a regular wintery outfit, jeans, coat, and a scarf covering the lower half of my face. Just looking at my outfit and you can easily know that I’m a guy. In the other photo I’m kneeling on my carpet, sitting on my knees. I'm wearing a white spaghetti top and jeans shorts. I've hidden my face behind a cat emoji. Much less manly, but it’s cute.
I've entered the bare minimum of information. I'm 20 years old. That I’m a guy. My height, 5ft 4. For my occupation, I'm a model. And that I live in Alaska, but that I’m actually from a small town in Virginia. I left all other fields empty. The title and description were required, so I entered 'Looking for a super friend' in the title and for the description I entered ‘I’m looking for someone who likes to be weird and watch anime with me.’ And that's it, that's my hopeless profile.
I see the big 0 screaming at me. No messages. It basically means that nobody cares about me. However, just as I start to wonder if I should just delete the whole thing a message pops into my inbox.
'I like cute bois' is all it reads.
I look at the dating profile and the picture in it. A manly man stares back at me. One of those ‘bro’ types with broad shoulders and a perpetual two day beard. His profile is just as bare as mine, not even his age is in there. But I guess he is like 35?
Finally! Someone is taking an interest in me outside of Onlyfans! That's cool! On some days I'm quite lonely. I often want to curl up against someone very badly and that someone should stroke my hair. We'd make little jokes and just enjoy our time.
Anyway, when I come back to reality I have sent a short message back, “What does that mean?”
Ehh, what? I look disturbed at my stupid response. I didn't mean to reply! What the fuck?! I sigh and quickly move the cursor to the close button, but his reply already arrives.
“Brunette. Preferably petite/short. Playful but decent. If available, I would love to meet you. K.”
That’s very business-like, and 'K', I stare at the letter. Probably his initials. Kyle, maybe? It's the first name that comes to mind. Karl perhaps? And a meet? What does that involve? It sounds like a date! My nerves get the better of me and I quickly close the website and try to focus on my 'work'.
I tell people that I'm a model. Except, my entire modeling career is through Onlyfans. Yes, I'm one of those.
My justification for it is that I'm only doing it temporarily, and because it's easy money. But also because I can look girly and cute all I want while hiding my face. It helps me justify owning female clothes and cute outfits. And, probably most importantly, I don't have to leave my home for it.
But, my followers demand attention every day. I sigh as I put on a skirt and wag my butt for the camera, pretending that’s a dance. Add on a trendy EDM track that’s hip today and done. I upload the 23 second clip and money starts rolling in. It’s such low effort.
Ka-Ching! $20 Dollars 'earned'. Yes, I know I’m pathetic. I think very lowly of my activities, in case you didn’t notice.
Maybe the mysterious 'K' is one of my followers? Wouldn't that be embarrassing? I don't want to think about it and spend the next hour sending the obligatory chats and responses to my stupid fans and I collect more tips. That's groceries covered for the month.
I wonder how many of them realize that I’m actually a guy. I’m not hiding my gender, or chastity, but since I don’t do nudes it’s not very obvious either. Grinning at the thought, my mind wanders back to the dating site. What if he is nice? Mr. K. What did he mean by liking cute boys? Is he gay? He looked way too manly to be gay. Maybe he thinks that I want to be a girl? I nervously grin and before I can stop myself I'm logged into the dating site again.
There are 2 more messages. The first one reads, 'Hello?' and the second one is a real message, “You'll understand if I want to keep things simple for now, but this is a serious inquiry. I'm not a stalker or a freak, just fascinated and curious. Let me know if you're interested. Kyle.”
Well, that answers that. He read my mind, his name is Kyle. Everyone is a freak though. Sometimes I think I am too, for wanting to dress and look like a woman. But it comes too naturally to be the habit of a freak, right? Why else do I barely have any body hair and a slender waist at 20? I stare at his message for many minutes before making a decision.
The lonely person in me decides I should take a risk today. I’m going to make a friend! I’m going to talk to Kyle. But I'm not kissing him if we ever end up going on a date though, or ever! I’m not gay. In fact, why am I even thinking about touching and kissing a man? Damn! Chill, dude!
“How do I know you'll be good for me?”
Another stupid response, but I have to be careful, right? My cursor hovers over the send button for 20 long seconds before I click it. Five tedious minutes later his response comes, “I’d like to have someone like you. Someone cute and sweet. If it works out, enter a proper relationship. I'll spoil you, be with you and treat you right, as long as you're the right girl for me.”
"Oh I see… You’re super gay!" I say to my computer. I’m not a girl, either. I just dress up as one.
My phone pings and another follower wants something. “Show me your naked butt.” And he offers a tip of $100US. My thumb hovers over the 'delete' button. I don’t do porn! I always promised myself to not do nudes and sex. But damn, $100 for a photo? I dig through my closet and find a pair of panties that covers half of my butt. I spend the next 5 minutes trying to be modest while doing what I consider to be porn. When I'm finally satisfied that my ass is sufficiently hidden, I take the photo and send it.
A new low for me. I'm so embarrassed that I forget all about Kyle and everything else. I shut down my computer and watch the grey sky through my small front window.
I stare at the clouds for a while, tomorrow there will probably be snow. I hate snow! Kyle enters my thoughts once more and I curiously start my computer again. The guy from the last photo isn't happy. He expected nude photos, more than one too. Instead of addressing his complaint I just report him for being a nuisance so I can keep his $100 and ignore him. Get a girlfriend you moron! I don’t think too highly of my followers.
Kyle also sent another message. His text reads a bit more happy, or hopeful, “I have a good feeling about you.”
“You don't know me…” I reply back feeling upset. What the hell? What does he know about me to have a good feeling? Does he even realize how creepy his messages read!?
2 minutes later his response reads, “Quick analysis; You're alone, or lonely. A young, petite girly boy without friends. You want recognition for who you are and you want someone to take care of you. That’s why you'll keep responding.”
Ehm… Creepy! How does he know all that? My hand moves the mouse to the delete button, but I'm too curious to ignore him. Fuck, he's right! Suddenly I realize that I am maybe more lonely than I care to admit, and I read the rest of his message.
“You think that you want to be a girl sometimes. And with me you will be. I prefer it that way. K.”
I nervously stare at the screen, then look around my apartment. I fully expect Kyle to be peeking around the room divider that’s between the sleeping and living area. How can he possibly know all that? This is too close for comfort and I shut the computer down and make dinner. Yes, let's call it that… A cheese sandwich with ketchup on plain bread and a glass of chocolate milk.
2 - Coffee with Kyle
I squat in the bathroom after relieving myself and push the buttplug back inside. It’s only small and I don’t particularly like wearing it, but sometimes I just feel like I should. I’m not sure why. Maybe I just like the idea of having something up my butt. It never really sits right though.
I read on Reddit that silicone plugs are more comfortable, and someone even wrote that a bigger, more bulbous, shape is easier to hold in. But I don’t know.
"Meow!" I growl at the mirror and head into the living room.
After Kyle’s message I’ve been thinking. I'm not sure why I keep reading his stupid messages. I’m not into guys and never really fantasized about it either. But I am fascinated with Kyle for some reason. Maybe just because he is the first to send me a message through the dating site. But if he is what he promises I finally have my weirdo friend.
He wants me to be a girl though. That’s what he wrote in his message anyway. That’s so not me. I sigh at his persistence, but I can't shake the idea of meeting him. In a flash I see us together, I’d be his boyfriend, or girlfriend rather. He'd be my boyfriend. What am I thinking? Am I that lonely? Or that desperate? I don't even know if he's real.
“Where are you?” I reply to him.
“I live in London, UK.”
"Oh…" I grumble at the screen. Instantly a feeling of loss comes over me. I thought he’d be in Anchorage.
“I'm in Alaska, United States of America.” I reply back.
There is no response after that and I busy myself with my Onlyfans. Mister 100 bucks, from yesterday, filed a dispute and is not happy. My mind is elsewhere and I don't pay attention to his bullshit. I don't properly read all the prompts and menus other than the ones that let me keep the hundred bucks and accidentally agree to the resolution he wants, a better set of pictures. I reluctantly send him his nudes, trying my hardest to not be naked while being naked.
What the fuck am I doing with myself? This is so far removed from what I set out to do. But money… Yeah, like I need it so badly. I feel like an idiot!
That evening Kyle finally sends his next message. He dares me to meet him in New York. Meet in the middle so to speak.
“Like that’s so easy…” I reply back. I can’t just take a plane, right? How does that even work? I’ve never travelled alone. After I click 'Send' I immediately regret my reply. Now he's probably coming to Anchorage.
I guessed right again, and he dares me to meet in Kincaid Park in 6 days. He’ll be there and we can enjoy the park and get to know each other. I stare at the screen, his decisive manner is actually quite attractive to me. But Kincaid park? What the fuck kind of choice is that. A weird curiosity pushes my reservations aside and I agree. If he wants to meet me that badly, maybe he really likes me? Or he can at least accept me for who I am?
“Yeah ok… But just come to the city center. Kincaid Park is not exactly the park you think it is, I’m sure.”
I’ve been there once, I don’t feel like going on a hike. Besides, it’s too cold anyway. Over the course of the next few messages we set up our meeting. NO! It’s not a date! Really, it’s not! It totally is though. After some back-and-forth we decide to meet in the 5th Avenue shopping mall. Then we move to Apple Messages and chat the night away.
Kyle is kinda nice I guess, he tells me he is an investment broker. He works for some bank in London that I’ve never heard of. He brags that he earns loads of money with it too. While he’s in town he’ll look at some business to invest in Alaska, like that should impress me. And finally he also tells me that transgirls fascinate him, but that he isn’t gay.
I think he’s weird, but kind, honest too. And him taking an interest in boring me is cool. I naïvely believe everything he tells me.
Other than a few short messages and ‘good mornings,’ he goes mostly silent after that. He told me he would prepare some things at his office so he can travel. In the early morning of his supposed arrival he sends another message, I stare at it filled with anxiety.
“Layover in New York! Super looking forward to meeting you!” Along with the message is a misaligned selfie of him at the airport.
Realization sets in, we’re actually doing it. He’s insane enough to fly across the world for me!
“Hey! Can’t wait!” I send back, and I consider offering to pick him up from the airport. But I’m too nervous and can’t bring myself to do so. I’m starting to think I’m making a mistake by meeting him at all. I've been on edge ever since I agreed to the meeting. Call it a sense of foreboding if you will. But I tell myself it’s because I’m just socially awkward.
What the hell am I doing with myself?
With Kyle arriving in a few hours, I start to prepare for our meeting. First things first, I squat in my bathroom and unlock my chastity. I’ve been wearing the thing for 3 weeks and 5 days, non-stop. A new record. My previous best was 2 weeks and 4 days before it got uncomfortable. I'm only removing it now because I don't want to think about it while I’m with Kyle.
I think about him and how long he would keep me locked up if he has the chance. Maybe forever? I get hard at the thought and feel embarrassed that a guy I never met can have this effect on me.
“FUCK!” I call out into the tiled room while leaning back against the toilet bowl. I furiously masturbate while thinking about us falling in love. I shoot my load through the bathroom with such force, it splatters against the shower curtain and I sink to my butt catching my breath while I slowly squeeze and pull on my balls and penis. Weirdest orgasm ever!
That afternoon I take a taxi to the 5th avenue shopping mall. It’s a typical sunny day, but it’s chilly out. The grey cloud cover disappeared and no snow fell. I’m wearing my casual jeans and a grey T-shirt covered with a purple hoodie for a jacket. My unrestrained penis is constantly hard. It’s weird to not feel the plastic around it. An arousing sense of freedom. And… Stop it! Focus! You’re meeting a man today. Totally not a date, either!
Inside I wait in front of the department store. It’s so awkward loitering around like this. I suppress the urge to re-arrange my genitals. How will Kyle know I'm here? I keep staring at the entrance but he’s not coming from that direction since suddenly I sense a presence to my left.
"Gotcha!" His English accent from behind me.
I flinch at hearing his voice and look startled at handsome Kyle. He’s wearing jeans, a white shirt and a casual jacket. Like he came straight from a business meeting. His face looks just like his picture. Chiseled cheekbones, with a 2 day beard. As expected he's older than me too. He's nearing 40 I guess, about a head taller than me. His grey eyes look down on me. He has broad shoulders and strong arms. Not a bad catch I suppose.
“Hi…” I mutter, but can't think of anything else to say. Kyle looks very intimidating. He pets my head and ruffles my hair and I relax a little.
"Nervous? I like your hair, it's cute! No skirt? I figured you for a skirt person." He says with a grin.
I dumbly nod and look at his big chest to avoid making eye contact.
“I don’t dress like that in public,” I mumble.
"Hmm… Come, let's have coffee." He invites me along.
Two minutes later we're in a nearby cafe. I stare at my smelly cup of coffee. I hate coffee. Why didn’t I ask for tea? What’s worse is that I can't seem to come up with anything useful to say.
I flinch as he points his finger at me, "What's your name?" His eyes bore into my being.
I quietly answer, "Fabian…"
"I saw that, but that's a boy's name, what's your female name?"
"Oh, I ehh, I like Sia." I shrug. Nobody knows that about me.
He looks at me and nods. "That’s girly enough I suppose."
"Ehh, yea, short for Sophia…" I hesitate.
"Why did you pick it?"
"I ehh, I don't really know. I just like it."
"Hmm ok, and where are you from?"
"Uhm, Scottsville, in Virginia."
Kyle nods, clearly having no idea where that is.
"Do you have any family there?"
I nod, "Yes, I don’t really keep in touch though. I left home a year ago, my dad kicked me out. He lives on the air force base here."
“And friends?”
“Here? No, not really. I chat with people on iMessage.”
"Hmm, ok. Good. You look like you're like 15… You’re sure that you’re 20?"
"I'm 20," I assure him, and smile at the questionable compliment.
"I see, wait here, I’ll get muffins. Enjoy your coffee. I'll be right back."
I hate coffee! I want to tell him. I want to talk to him. He's so normal. I know I should talk more, ask him a million questions and become his friend or something. I should want to know everything about him. But I can't think of anything to say. I quickly switch my coffee with his nearly empty cup. God I'm so awkward and stupid. Maybe I should just go home and forget about this.
I do a quick look-around to see if I can leave, but Kyle is already on his way back. He returns with 2 chocolate muffins and we eat in silence while stealing glances at each other. We’re super awkward and I don’t think we click at all, not even as friends. Kyle looks weird at ‘his’ coffee but drinks it without comment. Finally he signals to a waiter for the bill.
“Shall we go?” And he motions for me to follow him. I nod and we stroll through the shopping center. We don’t talk much. He has his ‘getting to know you’ questions and I reply, but don’t ask him anything. I feel too awkward to take the initiative.
“Ok, so, I came here to meet you Sia,” Kyle starts. “I expected you to be kind of shy… But damn, you’re like a super introvert or something.”
I nod, “Sorry… I’m ehh, I’m just nervous.”
“First time dating a man?”
I nod again. We’re not on a date though, right?
“I see. Well, lucky for you I think I like you. So if you’re not too scared of me, follow me if you want this to continue…”
He gives me a smile and a wink and walks to the traffic light where he waits to cross the road. I stare after him. A dare, huh? This is my chance, I should leave now. But before the light changes my curiosity has me follow him. He grins at me and we walk hand in hand to his hotel which is a block away. On the top floor we step into the most luxurious room I’ve ever been in.
Kyle sees me look, “First time at the Hilton?”
“First time in a hotel…” I admit.
Kyle laughs, “Well, this place is alright I suppose.” And then more seriously he says, “Here is your last choice for now, we can play together or you can leave."
“Play?”
“Yes, if you’re up for it I’ll play with you as if you’re a cat, for an hour or so.”
“Like with, eh, a ball?” I stare at Kyle being a weirdo, but I don’t refuse him. Actually, the attention he gives me is kinda enjoyable. You know, being near someone who actually pays attention to me, that’s nice.
3 - Playdate
Kyle explains that he likes to role play from time to time. And today he feels like playing with a cat. He calmly explains that he wants to test my obedience and what game he wants and what we’ll do. And I let him.
I stare at my hands as he tapes them up. He just finished my left hand, which is now a useless stump, covered in skin colored sports tape. Below my knuckles is a folded sock, as a sort of pad.
I'm getting super scared now. He told me I'd be his cat for the afternoon and that he’ll play with me. But I'm not sure what that means. I didn’t expect him to do bondage on me. He’s so intimidating and I’m just being the stupid introvert. Next he ties the belt from a bathrobe around my neck as a collar and leash. I feel the slight pressure of the belt all around. That’s somehow arousing.
“I have better stuff for this at home. But for now this’ll be fine. Are you OK?” He sort of apologizes.
Unsure of how his home is relevant I just nod my agreement.
"You're a cat now Sia. No more talking!”
"Yes sir…" I nervously croak.
A firm tap on my forehead, "No talking Sia!"
"Oh, yes. Sorry."
Another tap on my forehead and he gives me a stern look. I look shyly away. His eyes make me feel small and insignificant and my stomach twists into a nervous knot.
"Sit on your heels and balance on your toes."
I look questioningly at Kyle and he quickly demonstrates from his squatting position. I see what he means and balance on my toes. Before I can protest my left thigh has 3 windings of tape around it and my ankle. He does the same with my other leg, making sure my shirt is not caught in the tape. He then wraps down each of my legs about halfway down. When he’s finally done he pushes me on my nose and with a squeal I roll backwards onto the floor.
I squirm on my back with my stumpy legs in the air and my arms overhead, flailing like a cat getting a bellyrub.
"Now… Let's see what kind of cat you are." Kyle announces.
And for the next hour he plays with me. He has a feather on a string dangling from a stick and I paw at it from my vulnerable position. I giggle and squirm when he tickles me with it. He makes me follow him all over the room on my knees and hands. To my surprise I can keep up with him just fine, albeit super awkward.
Every time I want to say something he scolds me, saying something like, "Cats can't talk Sia!" And I quickly shut up.
He belittles me. He babies me and I think it’s cute and playful. We’re actually having fun like this. We’re being so weird, but I don’t care. On second thought Kyle is actually nice. Maybe we can ‘click’ after-all. But in the back of my mind I keep wondering if he remembers that I'm a guy. And if he does, he sure doesn't seem to care. Ever since I mentioned the name Sia he called me Sia as if that’s my legal name. In a way it kind of validates my feminine side.
He again leads me around the room by the bathrobe belt and I waddle after him on my tied legs. I’m starting to get tired, walking on my knees is actually hard work. I roll on my side when he abruptly turns around. Kyle sits next to me on the floor and pulls me on his lap. He then gently strokes my hair and fingers my ears. I make content noises and my body turns to jelly. Oh my god this is exactly what I imagined should happen with a lover. I’m so aroused by all this. Are we lovers? I don’t think so. I look up at him and he smiles at me.
"You're a good pet, Sia. I think I’ll keep you." He quietly informs me.
I look back at him with big eyes.
"Yes, you're so much nicer compared to my previous cat. She ran away, you see."
"Why?" I dare to ask.
“She didn’t like to be this way every weekend…” He vaguely explains.
“The whole weekend?”
“Yeah, why not?”
I can think of many reasons why someone would object to that. But I say nothing.
"But remember, cats don't ask things, Sia." He pets my head. "If you talk again I'll punish you."
I look at him with fear in my eyes as he tells me this. He makes it sound like a promise. I'm ready to stop now, I don’t want to be his cat girl anymore. My fun is completely ruined by the simple threat. But I have no control for now and I'm literally stuck in his grasp. We sit there for a while, he just strokes my face and hair. Whispering sweet words and little compliments to me. And all I can do is make little 'mmph'ing sounds and look nervously around. I don’t want to upset Kyle and risk a punishment.
Then he seems to make up his mind about something and asks me, "Ready for the next part Sia?"
I shake my head no, unsure what 'the next part' is. But I'm sure I'll find out soon, whether I want to or not.
Kyle isn’t really asking, he looks at me with a vague smile on his face, slowly stroking my body. I make, what I think is, a purring sound and wiggle on his lap. I’m trying to get up so I can leave.
"Excited huh? Sia?" He talks like we're about to do something fun. I squirm again while looking up at him, but I instantly freeze and my eyes go wide when I feel his hand near my crotch. I push my legs together but it's no use. He effortlessly pushes them apart again and cups my genitals.
"Oh…" Kyle sounds surprised.
I immediately start with damage control, "Kyle, no… I was going to tell you."
"Tell me what?!" He demands.
"I'm really a guy… I’m sorry." I look away ashamed.
Kyle 'hmms' and reaches down again, he rubs his hand over my crotch. My penis bulges against my jeans. "I already knew that… Obviously. With a dick like that I’ll have to lock you up when we get home." He whispers in my ear. My penis twitches when I hear this.
“What?!” I sound alarmed, but my eyes betray my growing excitement.
Kyle sees this and smirks. He then bends down and kisses me on my forehead. With his hand he keeps rubbing my genitals through my pants. Reaching further he presses on my butt, right where my sphincter is.
I moan at first, but then squirm and protest, “Don't push there!”
Ohhh, that feels so awkward. But Kyle just laughs at my reaction and seems to really really enjoy the power he has over me.
"Oh yes, I'm going to have lots of fun with you." He grins and he fidgets with the button of my pants. When it’s loose he slips his hand inside and cups my butt. His hand on my skin is warm, scary, more awkward than anything that came before. He stares into my eyes as he does this and enjoys seeing my nervous reaction.
I think I know what he's going to do. And I’m sure we didn't agree on that at all. I think he wants to have sex with me. And I really don't want that. In a flash I realize how incredibly stupid I am, how my curiosity put me in this situation. How my socially inept brain didn't think to tell anyone where I was going today. And maybe more importantly, how I let him tie me up and render me defenseless without setting any boundaries.
“Kyle no…” I refuse him.
“You don’t have a choice remember, choosing to stay was your last choice.”
“What?!”
“Don’t worry about a thing, with me I’ll take care of everything you’ll ever need or want.” Kyle informs me.
“But…”
“Yes, your smooth butt. All mine!” He interrupts me.
I don’t want to be his property and I struggle to get away, but it's no use. Kyle pulls on my jeans and moments later my ass is exposed in his lap. My chest is heaving and my shallow breathing betrays how scared I am. But at the same time my penis is rock hard.
Kyle, without a word, grabs my dick and holds it like a handle, he then presses a soft kiss on my nose, then on my lips and he pushes his tongue into my mouth. We only briefly kiss, but it feels like an eternity.
I give in to his advances and kiss him back. Which is surprisingly easy and arousing. It’s like the room is filled with fog. I’m unable to see where but surely there is a cliffside somewhere and I’m stumbling right at it. I’ve lost my initial fears though, the kiss felt safe, comforting. I guess I’m more gay than I thought.
I'm a man, of sorts. But really I'm his plaything. He said I'm good. I guess we'll do this and I'll go home after. Or maybe I should stay with him? I'm going to have gay sex! I don't want to have sex, do I? I’m a virgin, it shouldn’t be like this! Maybe as an experiment though.
So many confusing thoughts. Turmoil, that’s the appropriate term for what’s going on in my head.
He pushes me aside and gets up, beckoning for me to climb up on the bed. It’s a struggle, but I manage to wiggle onto the foot of the bed. When I raise my leg to try and shimmy fully onto it he stops me, my stumpy legs hanging down over the edge. Damn I'm so exposed, he's going to fuck me for sure. I just know it.
“What are you going to do?”
“You know what. You're so wonderfully submissive Sia. I love it."
“I’m not…” I weakly refuse him, but I don’t sound at all convincing. I try to look at him but can't really see what he's doing now. Suddenly his hand caresses my left butt cheek and from behind his voice sounds.
"You're a virgin are you?"
An invisible force squeezes my throat shut and my stomach churns at the thought of being fucked by this man.
"Well? Are you?"
I nod vigorously.
I keep quiet and don't even dare breathe. I hold my breath for as long as I can while my mind races and I think back to the past hour. The playing was kinda fun. Role play is fun, I enjoyed getting all the attention as I waddled around on my tied legs. And when we played with his feather and him touching me like you would a cat was kinda arousing. Kyle is a nice man, right? Aside from his threat to hurt me he has actually been kind and charming.
My thoughts are interrupted when his finger rubs against my sphincter. I let out my breath in an elongated gasp, here he comes! His finger slips in and he slowly pumps in and out. It’s slippery and goes in easily enough. But I dislike the sensation all the same.
"Mmmmmnoooodont…" I moan, god it feels awkward to have someone finger me. I squirm and struggle, but he just rests his other hand on the small of my back to hold me in place. An immense sense of loss of control comes over me. The finger disappears and a moment later his penis presses against my sensitive sphincter. It too feels wet and slippery. I twist my head to try and see what he’s doing but it’s impossible. Without another word he enters my ass.
"Ohmnooooononononoooooo!" I groan. Damn he's big. What the fuck! I feel like I’ll split in two.
He slowly pushes in until his crotch rests against my butt. I feel like bursting. Then he slowly pulls out until just his tip is still inside and he thrusts in forcefully again. In this moment I discover I can squeal like a girl. With a wet splat his crotch slaps against my butt.
“Kyle pleaseeee…” I moan at him, but can’t think of more words.
He starts fucking me and I’m mortified. I’m too embarrassed to even acknowledge what I’m doing. What HE is doing. We’re being super gay. But I guess I have no choice but to just let it happen and escape when he's done. Yeah, right, LET this happen, as if I have a choice! I promise myself to erase this day from my memory and forget I was ever here.
It turns out that Kyle is not a kind or nice man after all, without consideration he roughly fucks my virgin ass. We both moan and groan, mostly me moaning like a girl when his crotch hits my butt, and him grunting when he thrusts in. His balls slap against mine over and over.
"Oh my god, ohmygod! Owowow! NO! ohmigoooooood! Stop, please! Ouch!” I finally refuse him. But it’s too late. I’m pawing at his hands that hold me down. But as our sex continues my protesting moans turn into some twisted kind of pleasure. His penis pistons in and out with ease and at a steady pace. My refusal turns into encouragement, “YES! Oh, more! Oh so gooohoooood!" I yammer and squeal into the mattress as Kyle pounds away into me, his hands firmly holding on to my helpless body. My penis is erect and bent down awkwardly because of the mattress. It hurts a little. I'm not very big, but as any man knows, bending an erect penis down is not all that comfortable.
“Oh fuck! YES, UHN NO. More, stop! Oh, uhf, more!” I grunt and squeal along with Kyle's thrusts.
For a moment I consider how it must hurt if I had worn my chastity. My cage is very small and any hint of a hard-on will cause discomfort. It's part of the challenge of wearing it, someone told me on Reddit. I feel lucky to not have to deal with it today.
Kyle then thrusts in extra hard and I squeal and struggle to get away as he crushes me under his body. Actually on some level I really enjoy the sex. But honestly, I don’t want it. Kyle doesn’t seem aware of my objections. He grunts in tune with his thrusts, his hand smacks my butt several times, leaving a red mark. And I'm shaken to my core when he cums inside of me with an elongated moan. When he pulls out he shoves me forward into the mattress. I’m discarded as he leaves me so he can clean up in the bathroom.
I lie there panting, cum dribbling from my butt. What the fuck just happened? What did I do!?! I hang over the edge of the bed. I can’t even stand up and clean myself up, I’m so useless in my bondage. I hate it! But fucking hell I love it!
4 - Not a virgin anymore
We're awkwardly walking hand in hand towards Elderberry park, on the seaside. I’ve actually never been here, so I’m not sure what to do. I dumbly follow Kyle. He had insisted on treating me for a hotdog, an early dinner. I don’t know why, but maybe he never has had a hotdog before. I hinted at going home, but he wouldn’t let me. Instead we're looking for a hotdog stand or someplace that sells them. Like before, we don't say much to each other. I feel super awkward walking hand in hand with a man. It makes me feel like I’m his boyfriend. Luckily the few people that are on the street are not paying attention to us I think. Yet I feel that everyone stares at me, I can feel their eyes burning on my back.
Kyle doesn't seem to care at all what people think of us, he's looking around like a tourist and navigates the city with his phone. I just answer his simple questions or nod. I'm still stunned from him fucking me and shudder the thought.
You know how they say ‘she couldn’t walk straight for a week’? That’s how I’m feeling right now. I keep clenching my butt, because if I don’t, I feel like it’s gaping wide open.
"There?" I point at a little take-out place that has a hotdog sign.
"Yeah, if they have nice stuff…" Kyle agrees.
I have no idea, other than the shopping mall I never come to this part of the city. A couple of minutes later we both have a hotdog. I just added ketchup and mustard, but he went for the complete thing, with onions and everything. It's good, and we look at each other as we eat.
"So about…" I start to inquire about what we’re doing, and if we’re a thing now. He seems to think so.
"Yeah, uhm… I dunno," Kyle interrupts me. "I like you, always wanted to fuck a tranny… And now I have you."
He smirks to himself, but I just look shyly away but say nothing. I don’t want to be his girlfriend, nor am I transgender! Geez, he’s changing my ‘me’ already? Or doesn’t he get it?
“I’m not trans…” I finally say.
“Trans, crossdressers, ladyboys, same thing…” Kyle casually generalizes people.
I say nothing but don’t agree with that at all. But I don’t want to start that argument. So I just sit there feeling insulted while I wait for this ‘date’ to finally end.
"You're very quiet, am I still intimidating you?" Kyle wants to know.
"No, well… Kinda, but I'm just stupid with people."
Kyle 'hmms' gives me a shove with his shoulder like we’re close friends. I flinch and scoot away from him. He smirks at me and scoots closer.
"So uhm, are we done?" I ask.
"We’ll go out a few more times and when I go home I want you to come with me.”
“Uhm…” I’m lost for words, go where? To his country? That’s not how that works, right? What the hell is wrong with this guy?
“Alright, listen. Here’s the deal,” He sees my confusion but sounds upbeat. “I want a special girlfriend. Someone adorable and lovable who I can parade around at parties. Be that guy with the cutie that everybody wonders about. And I want it to be you!”
“What? Why? No… I’m not a girl!” I refuse him.
“I kinda sense you’re not really into me,” he charges on without listening. “And that’s fine, you’ll learn to like me once we’re in the UK!"
"Eh, I don’t know about that."
Then it hits me! He only came to Alaska because he can be a hundred percent sure nobody in his social circle will know me. That way I can be the mysterious lover from a place that his friends don’t know. It’ll explain why I’m different, yet I’m mysterious enough so that nobody will question why I’m not feminine like they expect. It’ll explain my quirks, and it will probably mean he’ll never admit to his friends that he’s actually dating a guy.
I sit there fuming for a moment and ball my fists in powerless anger and want to tell him to fuck off and leave me alone.
Kyle sees the anger in my eyes and course-corrects, "Or, maybe not…"
"Yes!" I tell him again, agreeing with his ‘maybe not’ but he interprets it differently.
He sounds surprised, "Oh? So you'll come with me and be my girl then?"
I stupidly nod, barely visible, I can’t refuse. "If you want…" My voice trembles as I say this. I immediately regret my agreement and course-correct. I bundle all the willpower I can muster, "Actually, I can’t. We don't know each-other at all."
"I've been in your ass…" He states, "Surely that counts for something.”
My face turns red from embarrassment and I stay quiet. We finish our hotdog in silence and I fidget around. I felt my phone vibrate several times. Surely that’s Onlyfans wanting my attention.
“Oh, and don’t worry about money, or relocating to the UK. I’ll handle everything, you’ll want for nothing," He promises.
I stare at my knees and don’t say a word, an invisible force prevents me from speaking again.
"So uh, you always wear girls clothes?" Kyle tries.
I shake my head, "Only at home."
Kyle looks puzzled, "But this outfit…"
"It’s a guy's outfit," I interrupt him.
"Hmm?"
I stare over the water, thinking of a way to end this. I feel like crying. This guy only sees what he wants to see! He fetishizes me. And he’s in such a state of denial that he won’t even acknowledge who I am, or who he is.
"Well, let’s head back. We’ll watch a movie." Kyle ignores my sad look.
With great difficulty I pull my mind together and I refuse him again, "Like I said, I don’t know you. Maybe another time."
Kyle 'hmms' once again, "Today doesn’t count then?"
"I eh…" I stammer, not sure what he’s doing, but I feel like I’m walking into a trap, no matter what I say next. He’s totally ignoring reality or something.
"Tell you what, I'm coming with you to your home. We’ll spend the evening together, maybe you’ll open up then."
I stare at him, "And then?"
"Then, you can see that I mean you no harm and you’re going to get comfortable with me."
Now I 'hmm' and I feel my penis swell in my pants. I get so hard that it hurts. The thought of this possessive guy forcing himself into my life sort of excites me. But it’s also super scary, and common sense kicks in at the last second.
"I can't, no… I have to get home. Alone…"
Kyle is quiet for a moment, but then makes his next insane decision.
"Fine, forget it. But you'll suck me off before I leave."
I stare at him and wonder what he's thinking, deciding all these things. First he wants me, now he doesn’t… What the hell!? But I’m also glad, the end is in sight.
He pulls me along and makes me suck his dick in the park’s public restroom. I refuse at first, but just as he raises his hand as if to slap me I decide to just get it over with. I’m such a fucking loser, but it’ll probably be faster than trying to fight him. Without much enthusiasm I open my mouth and do the dirty deed. Like I know how to do a blowjob. He just stands there looking down on me with a stupid knowing grin on his face.
Just as I gag on his penis for the 3rd time he tenses up and ejaculates in my mouth. He uses both hands to push my face into his crotch. I can’t breathe for a moment and I feel completely helpless again. I try to get free by pushing against his legs, but I may as well be pushing against a brick wall. His semen tastes disgusting but I have no choice but to swallow. His penis is pressing in the back of my mouth. Horrible!
When he finally lets go of me I cough and splutter my disagreement. I spit on the floor in disgust while trying to get rid of the taste in my mouth. Fucking hell, how do women do this?! I wipe my face and when I finally look up Kyle is gone. He didn’t even say goodbye. What an absolute asshole!
My sense of relief is greater than my upset though, and I quickly go home to wash my mouth and promise myself to forget this day.
I’ve deleted my dating profile too. Never again!
5 - Spotted
It’s been several months, Kyle is a distant memory. But the effect he had on me is not. I sigh as I upload yet another video of me humping my dildo. Yes, I know! My sad existence has sunk to a new low. For I am doing porn now. Against my better judgement, mind you.
In a moment of weakness I bought an even smaller chastity cage, to punish myself for meeting Kyle. I’ve been wearing it 24/7 for the last 5 weeks. Every day is a new record!
This one is made of metal and originally had a little short tube fixed to the tip that goes inside my penis. Unfortunately I couldn’t get used to it so I took that out. Without it, I adjusted to the restrictions well enough that I figured I would just wear it for locktober. Only 4 days until it’s November, no-nut-november apparently. And if I can manage it I guess I’ll wear it through November as well. Or forever… I don’t really care at this point.
All throughout the last few weeks my follower count has steadily grown. And in another moment of weakness I uploaded a picture of me inserting my butt plug. I was immediately ashamed of myself for earning almost 25 dollars in twenty minutes for it. I spent that money immediately on cookies. When I got back home loaded with Oreos and saw it still doing well, that post alone paid for a week of groceries.
Something has to change! After some thinking I figured I’d do something so ridiculous that its failure would deter me from ever uploading nudes again. After some deliberation I came up with a challenge. That being, I announced the ‘event’ in a post and wrote that if I could fit my deodorant can in my butt and collect $3000 in tips within a weekend, I’d buy a real dildo and upload content of me using it. I choose $3000 because that’s usually what I earn in a month.
I spent an hour trying to fit the can in my behind, bottom first. It hurt at first, but once it was in it slid in and out easily. The sliding sensation was pure bliss. Like nothing I’d ever felt before. I then pushed the can in as deep as I could and took a few photos. Then filmed it sliding out from a squatted position.
That Friday I uploaded 3 photos and a 19 second video clip and bam! I was officially a pornstar! Especially since two minutes later I had already ‘earned’ several hundred dollars from my stupid fans. Every time I refreshed the page my income number grew and grew. By midnight I had earned $1805. When the weekend was over, I had over $9000 dollars. Safe to say, my idea backfired terribly.
I should just back out and ignore the inevitable complaints. But money… EASY money! The temptation was too great, or so I told myself. Imagine the amount of high quality clothes I could now afford. And the new iPhone. And, and, and… Yes, I know, I’m a terrible person.
I ride my dildo daily and upload little clips of it regularly. Every time I do, I feel like such a moron, but I earn more money than ever. Eventually I figured that since nobody sees my face anyway, I may as well exploit my kinks for money. Kyle broke me and I crave to have cock in my ass more and more every day. I guess I’m a little gay because of him after-all.
Just as I squat down to record my next porno there is a knock on my door. I look startled at the door but decide to ignore it since I’m not expecting anyone. But there is another knock, more insistent this time.
“Oh, fuck off!” I mutter under my breath and quickly slip into some jeans and a shirt.
“Yes?” Before I can finish my greeting a phone is shoved into my face and I see a butt hovering over a dildo.
“Busted!”
I stare at the photo and then the cute girl holding it. I’ve seen her around, she lives down the street I think. but we never talked to each other.
“Ehh…”
I look more closely at her screen and think that it’s me squatting down over my dildo, seen through my back window.
“I saw you! That’s so hot!” She informs me. She steps forward and I step back, before I realize it the door falls shut behind her.
“I’m Maddie!”
“Ehm, OK… Sia, ehh Fabian.” I stutter.
She giggles and looks around, “You’re so cute! I have a huge crush on you!”
“I’m, ehh, not who you think, I think…” I mumble. Her beaming smile exudes an intense energy. It’s wildly attractive, but a complete opposite of me. I’m not sure what to think of that.
“Sure I do, you’re the cute-boy-who-wants-to-be-a-girl.”
What?! People think that of me? “Yeah? I guess…” I half agree.
“Why do you want to be a girl?” She rises to her tiptoes while leaning towards me like a nosy child.
“I ehh… don’t want that,” I finally find my wits, “Who are you? Why are you here?”
“I’m Maddie! I told you! And I’m here to meet you, consider this your audition!”
“Audition?”
“For being my girlfriend!” Maddie calls out. She shakes her phone suggestively, as if to say ‘or else…’
“Your… girlfriend?” I freeze and just stare at her. My mind wanders for a moment. I guess she could be my girlfriend, yes. We’re about the same age I think. She’s cute and energetic. I kinda like that. I always thought that a person like her would pull me out of my shell.
“Yeah, you’ll be my girlfriend!” She decides for us, “I’m so into you, I’ve been watching you for months. Every time you walk past, or in that cafe. You’re so cute!”
Oh it’s like that, stalker type. I guess I’ll need to move. Far away from her if she won’t see reason. Wait, why is my first instinct to run away?
“How did you get that picture?” I ask.
“From the alley.”
I just stare at her. For some reason I never considered people looking into my window. In fact, I never even saw anyone in that dirty alleyway.
“I’m sorry, who are you?” I stutter.
“I’m still Maddie, can we sit down? Let’s get to know each other!”
“Yes, Ehm, there…” I point at my couch.
She steps to the side and plops down on the couch.
“Whoa, there it is.” She giggles at the dildo that’s stuck on the floor.
6 - Downward spiral
We talked for a bit and after the first introductions she declared we’d be perfect for each other. She’s not here to blackmail me with the photos either. She has a bunch of photos of me. Me just walking in the street, sitting in the cafe sipping my tea, waiting to cross the street. It’s super weird, who does that right? She must be crazy, but at the same time she sincerely seems to like me.
Because she he has been looking into me, she knows a few things about me already. My favorite cafe, what I do there. My dress style. Stuff like that. Yet I know nothing about her other than that she’s kinda cute. I like her smile, it vaguely reminds me of a childhood friend, some friendly guy from high school I lost touch with. It’s familiar and nice.
When she’s done talking about herself she completes the insanity unfolding on my couch by lifting her skirt. I stare at the bulge of her penis straining inside a pair of panties. I instantly recognize the lines and pattern pressing against the fabric as a chastity device.
“Whoa! What the fuck!?” I call out.
Maddie giggles, “You didn’t know did you!?”
I shake my head no, unable to avert my eyes from her crotch. Maddie is a guy? I quietly sigh. My disappointment is immense, just as I started to get into her… But I compose myself and ignore my feelings for now.
“Your voice… It’s so, ehh…”
“Feminine?” Maddie laughs. “Yeah, I’ve had surgery… These too,” She squeezes her boobs between her upper arms.
“Ehh…” I’m lost for words. I never ever considered going that far myself. But Maddie clearly did and she looks amazingly feminine and cute and cool. I must be gay after-all. But I always thought Maddie was a girl. That doesn’t make me gay! Maybe? But really, she is? Actually, she’s transgender, so that makes it not gay for her too. Right? Argh! It’s so confusing!
I remain calm on the outside, I’m stunned really, but in my head I’m going more and more insane by the second.
“How? Why? Ehh, what?” I stammer, sitting across from her. I still can’t believe my eyes.
“After my accident I needed corrective surgery to my face. Also my thigh and lower leg. So I took that chance to become the real me. Look!”
Maddie shows me a long vague scar on the side of her calf. And a smaller one on her wrist. They’re almost invisible.
“I have 5 pins in my leg, but otherwise I’m fine!” She adds.
Somehow I get the impression she's not fine with it. Maybe she has pain from it? But I could be wrong, instead I ask,“The real you? What accident?”
“Yeah, I changed my nose, my voice and my hips to become the woman I am.” Maddie looks all serious now. “And uhm, I crashed my motorcycle into a moose, the stupid monster just stepped in front of me!”
“Ok, but… Wow!”
“Yeah! I totally freaked out too at first, whenever I looked in a mirror! But later I also got implants, last year actually, and I’ve been doing hormone therapy. A whole new me.” Maddie laughs, ignoring the seriousness of what she’s telling me.
“You look really nice though. I would’ve never guessed…” My voice trails away as my eyes fixate on her chest while thinking about the moose she ran into.
“Thanks!” Maddie glimmers proudly at my approval.
I stare at her chest. She has the perfect cleavage, suggesting a firm cup-size, maybe a handful? I have no idea, I never saw breasts from this close-up on a young girl, man… WOMAN! Maddie is a woman I decide. My eyes slowly head down and end on her crotch again.
“Why the, ehh, that?” I dare ask.
She sees where I look and explains, “Women don’t have one… But I can’t get rid of it. It doesn’t feel right.”
“Uh-huh…”
“So I lock myself up until the right person finds me. Then we can decide together what I’ll do with it.”
That does it for me, she’s absolutely nuts! So shameless and open about who she is. So confident. So very much unlike me. But I really admire her confidence.
We fall quiet and Maddie straightens her skirt, covering her legs again. She looks at me with questioning eyes for a few moments.
“So what’s your story?” She then wants to know.
“Me? I, ehh, I’m just boring…”
“C’mon, tell me!” She encourages me.
“I like dressing up as a woman.” I explain and hastily add “But I’m not gay.”
“Sure you aren’t…” Maddie smiles deviously, “That’s why you have that!” She points at the dildo across the rug.
“Yeah, eh, about that. I met a guy a while ago. And ehh, something happened. And then, well, uhm, since then I’ve been wanting to try things like that.” I shyly elaborate.
Maddie snorts, “So you’re gay then.”
“I’M NOT GAY!” I call out, “Geez!”
“Ok, ok… Sorry!” Maddie apologizes, “You’re into trans girls then? Me?”
“Sure… Yeah, uh, maybe?” I timidly admit. I really like how Maddie looks actually. And it solves the ‘not being gay, but wanting cock’ problem for me too.
Fuck! I’m such an asshat in denial, just like Kyle.
“See? We’re perfect for each other!” She leans forward and puts her hand on my knee. “Let’s go out some time. Yes? Just like friends, and we’ll see what happens.”
And so we do. Several times in fact. Maddie is kinda cool. But she’s also crazy. Well, not really. But she has zero shame about herself. I can’t help but admire that. Unfortunately it highlights my own awkwardness and I don’t know what to do with that.
Today is our seventh date. We’ve been going out two or three times a week for about a month. We’re becoming good friends I guess. We hung out in the shopping plaza, and we had tea a few times. We watched anime together. It’s fun. She takes a lot of selfies of herself, and us.
“Can you put your phone away? Please?” Maddie looks frustrated when I once again swipe up through a dozen Onlyfans notifications on my phone.
“It’s uh, an app…”
“Yeah, duh!” She calls out. “What are you doing that’s more important than me?”
She grabs my phone and scrolls through dozens of tips and requests.
“What’s this?”
“Work, I guess…” My voice trails away, I suspect I’ll be single again soon.
“Ohmygod… 16237 followers?” Maddie quietly says with a startled look. Her hand covers her mouth in shock.
“Sorry, I should have told you sooner…” I start to apologize and make excuses, “It’s just because I couldn’t find a job!”
“You do this for money?”
My head turns red with embarrassment and I whisper, “Yes…”
Maddie then smirks without looking up and furiously types something on my phone and hands it back, I stare at the browser as the Reddit page loads. A beautiful naked girl appears, seductively swaying her hips left and right.
“What’s this?” I wonder, “That’s you?”
“Eh, no, kinda. I use AI to make that. That way I don’t need to be naked myself.”
“It looks like you…” I look closer, there are freckles on her face and arms. Same as Maddie has.
“Yeah, but look at the light, and no penis… it’s fake.” Maddie looks smug at me.
I notice the differences now and wonder why I never thought of using AI to make porn. Half the world probably knows what I look like by now. I could’ve just done this instead of degrading myself.
“And you do this for money?”
Maddie smirks, “No, it’s just a silly hobby.”
Maddie sees my look of wonder, “Oh Sia, I have so much to teach you…” And she laughs at my goofy face.
“Fabian…”
“What?”
“My name is Fabian,” I quietly say.
“Nah, you look like a Sia to me. Fabian is a boy's name…” Maddie laughs, she pushes a strand of hair behind my ear from across the table with a wanton look in her eyes.
I say nothing and wonder why everyone I date insists on me being a girl. She knows that I only do that at home. But she walks right over me.
“You don’t mind do you?” Maddie asks with an intense gaze.
“No, well. It’s just for at home, you know that.”
“Yeah, but then just be a girl all the time… Easier!” She grins, “And it’s what you secretly want, no?”
No, that’s what you want… I think. But I say nothing. I wonder if dating someone will always be this awkward. Actually, Max, the guy from last year, was the only one I ever met who thought femboys were real. After dinner we head home and Maddie sort of just walks in with me and doesn’t leave. We watch a movie and I fall asleep on the couch midway through with Maddie leaning into me.
The next day I wake up on my couch with a pounding headache. When I sit up I feel my pants around my ankles, when I look down I yelp. I’m in my plastic chastity device. How did that happen?
“Maddie?” I call out. But there is no answer.
I call out again, “Hey Maddie? Did you add eh, did you, put ehm…”
There is a note with a key on the coffee table. I immediately try to unlock myself, but the key doesn’t even fit the lock. Reading the note it says, ‘You have my key, I have yours’ She signed it with a smiley.
What the fuck? She undressed me in my sleep? Put the chastity on and stole my key? That’s a massive intrusion, but it also excites me and my penis swells until it hurts.
Fine, I’ll play her game!
7 - Blissful escape
“Goddammit Maddie! Please, it’s been so long!” I curse at her over Messenger.
“Not long enough!”
“But I gave you your key weeks ago! Why can’t I have mine?”
“I’m still upset with you!” Maddie informs me. “And if you don’t stop asking I’ll never give it back!”
“I told you it was a mistake! I’ve deleted the post! Please, it hurts!” I am getting frustrated now.
I accidentally uploaded a photo from us, with her in the background. You can’t tell it’s Maddie, but she knew it was her and naturally saw that as a problem. And I exposed enough of my face that people can recognize me, which is even worse.
Maddie immediately broke up with me and hasn't talked to me since. She only sometimes replies to me because I keep begging to get my key back. It’s been 4 months, 3 weeks and 6 days. At first I didn’t think much about it, just more chastity. Easy! But since about a week ago my balls constantly chafe and pinch. It hurts and I desperately want out.
“Please please! PLEASE! It hurts me. I’ll do anything!” I write my desperate attempt, but the conversation locks up and I stare at the disabled chat. She blocked me. Didn’t I say she was insane? Fucking hell, shes being so inconsiderate!
Ten minutes later I pound on her door, but she won’t open it. Maybe she isn’t even home. After a while I give up and sit on the curb thinking about my next move.
Fine, fuck her! Emergency plan time. I’ll mutilate myself if it means that I can get out of this thing today! I can’t stand it any longer. I hail a cab and have it take me to the nearest hardware store.
At the store I stare at the electric hacksaw that’s supposedly my rescue. The saw blade is long and sharp and pointy. Not at all what I need. I didn’t think this through… Maybe something smaller? Bolt-cutters or something. Surely that’ll work better.
When I get home I’m armed with a pair of wire cutters. I immediately undress, skip into the bathroom and squat down and attack the cock ring. The tool bites down on the plastic and I try to cut through it with all my strength. Of-course I don’t have the upper body strength to just cut through the ring and the awkward angle is not helping either. Only a tiny indentation shows in the plastic ring.
“Fuhuuuuuck!” I groan.
I spend the next hour attacking my chastity cage, little cuts and scratches are all around the ring but it won’t budge.
With a defeated sigh I sit on my toilet and think of my next move. Can’t I just pick the lock? Yeah!
I sit on the couch fidgeting with a paperclip and just as I turn the little piece of iron it breaks and a piece of it is stuck inside the lock. Staring at the broken paperclip in disbelief for a moment. I give up, even if I had the key I can’t get out anymore.
I weep and cry for a good while before I come to my senses, back to the wire cutters I guess. I roll on my stomach on the couch so my knees can land on the floor and the cage catches on the edge of the couch as I slide down. With a quiet snap the piece that connects the sleeve to the ring breaks right off.
The plastic sleeve drops to the floor and the fresh air caressing my penis feels so good that I shudder and almost cum right there and then.
I stare at it for a moment, too stunned to comprehend that the shitty plastic chastity cage I used was never a secure prison. But then realization sets in.
“HAH!” I call out, an elated sense of euphoria comes over me and I grab my penis and hold on to it. I feel so relieved that it’s laughable. “HAHAA!” I call out again.
I frantically work my penis and balls through the ring and throw it aside. I’m so happy to be free that my dick gets incredibly hard, I could flip the coffee table upside down with it if I wanted to.
Holding on to my penis, I masturbate so roughly that I hurt myself more than the chastity cage did. But I don’t care, after almost five months the insane urge to cum is too strong for me to care. I tense up and four, five, seven dollops of thick semen shoot through my apartment, landing god knows where. But I don’t pay attention to that and let out a guttural moan. I sit on the carpet, my red, chafed penis in my hand.
I’m free!
Then my phone buzzes and Onlyfans demands my attention. A few seconds later another notification pops in, Max is in town and wants to meet.
“Hi Fabian. How have you been? I know this is stupid but I can’t put you out of my mind. I know it’s you from Reddit. I recognized the cat-anime poster on your wall. If you can, please come to the cafe in an hour. I really must see you.”
Oh crap… In a flash I remember our stupid kiss. I also half remember what he said to me. He’s not gay, but likes femboys? Or what was it? Something like that. Totally gay though…
I forget about Onlyfans and think about what to do while I clean up my mess and 30 minutes later I still can’t tell him ‘no’. In no small part because I’m just too curious about what he wants. So I decide that I’ll meet him. And if we click, he can have his femboy.
End
The boys meet shortly after and hit it off really well. Fabian is even brave enough to ask for tea this time.
After some introductory chit-chat Fabian insists on just being a Femboy from time to time and not wanting to be a woman. It is important that Max understands and accepts that.
Max is totally fine with that, as he mentioned the year before already, he is into femboys. He even admits to being gay this time.
3 hours later Fabian is lying face-down on his stomach on his bed, grinning from ear to ear. 3 streaks of semen are splattered over his back.
“Max?”
“Yes?” Max’s voice echoes from the bathroom. He’s trying to get the shower to a nice temperature.
“You’re welcome to stay with me, OK?” I invite him into my life.
“I didn’t book a hotel…”
“Yeah, you said, but I mean after.”
“Oh, like so… Then why don’t you come to Florida with me?”
“Just like that?”
“Yeah, why not? We’ll just see what happens right?”
I giggle and roll on my back and instantly regret it, now my bedsheets are covered in cum too! Crap!
“What’s it like in Tallahassee?”
“Come with me and find out. I have a spare room…” Max invites me back.
Yeah, right. Like we’re going to use a spare room. But he’s probably right, I should go with him! Screw Alaska and the cold climate, and screw being alone all the time. Hell, I’ll go find a real job this time. So screw Onlyfans, too!
Actually I’ve made a ton of money, maybe I don’t need a job? I don’t know how long that will last, but surely Max can help me with that.
I call out, “Hey Max?”
“Yes?”
“Know of any jobs I can do over there?”
“No need, I have money…”
“Yeah, but… Shouldn’t I do something?”
“Fabian, I am next in line to take over my dad’s company. Don’t worry about that for now. Come shower…”
My stupid grin widens even further.
“What does your dad do?”
“He owns a construction business. I’ll tell you all about it if you join me.”
“Oh? And you’re not going to pretend I’m a girl to your friends and stuff right?”
“Ehm… No? We’ll tell everyone once I get used to the idea myself.”
Hmm… That doesn’t sound good.
“You’re coming?” Max peeks around the bathroom door.
I crawl off the bed and join him.
“I’m scared…” I nestle my face against his chest and he embraces me.
“Me too, but my parents are usually pretty cool. We’ll just have to make it work. Do you trust me?”
I nod my head in agreement. Fine, I decide, I’ll be his boyfriend.
~~ The end ~~