Chapter 32 - A Night to Remember

Masquerades 101 by Emily

Posted on 16 Views / 1113 Hits Word Count: 5724 (25 minutes)

Synopsis: Friday Date Night is finally here. What does Tyler and Madison have in store for Vic and Nic?


Content Warning: Chapter has Sexually Explicit Content.

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“Get up.” Madison said, poking me. 

I had fallen asleep on her couch last night watching movies with her. I grabbed my phone and looked at the time. It was 9 something. “It’s Friday, I don’t have class,” I groaned.

“Me neither,” she replied. “I was going to go out to the store so I can get some food for the weekend. I do have a guest to feed.”

“You want me to go with you?” I asked, still groggy.

“Yes I do.” she said with a smile.

I stretched and sat up on the couch. My overnight bag was sitting on the floor beside the couch. I pulled out a clean shirt and exchanged the one I was sleeping in with it. “There. I’m ready.”

“Wait, I still need to put a bra on.” she said. “If I didn’t know better, I’d say you enjoy being a guy so it takes you 5 seconds to get ready.”

I groaned again. “I’d trade that to get my body back.”

“I know.” she said walking to her room.

I slid my still-tied sneakers on. “Where to?” I asked.

“Grocery store.” she said from her bedroom. “Liquor store to restock our wine collection. Maybe a clothing store or two.”

I nodded as she came out of her room. “That’s a lot of stops.”

“I’m taking advantage of the fact that my current guest has a car.” she winked at me.

“Oh, so you’re only dating me for my car.” I chuckled.

She stopped and smiled at me. “Oh, are we dating?”

I looked at her wide eyed. Did I assume wrong? “I uh… thought...”

“Shhh.” she interrupted. “We are, if you’re ready.” 

I felt something in me flutter. It’s out in the open now. “I think I am.”

“Great,” she said walking to the door. “Let’s go.” She made her way to the door.

“Now?” I said. “I just confirmed we’re dating and you're eager to get to the store?”

“I have to feed my girlfriend.” she said. “And I’m out of celebratory drinks as well.”

I stretched, and yawned again. We grabbed our coats and went out the door.

* * *

After buying groceries and wine, I figured we were done, but Madison had other plans. She dragged me to the clothing store.

I watched her browse dresses. I browsed as well. There were some really cute dresses. I took one off the rack and examined it, frowned, then put it back. Hopefully one day I can wear these again. I turned back to Mads and asked, “Mads, are you looking for anything in particular?” 

“Nope. I’ll know it when I see it.” she said.

“But I can’t help, then.” I said pouting.

A rack of sweater dresses caught my eye. “Oh I like this material” I said, taking the sage green dress off the rack.

“Do you want to try it on?” Madison asked.

“I can't,” I said. “I’m still in this stupid male body.”

“Nicole,” she said. “You’re a woman. You can try on anything here. Especially while I’m here, if you’re worried.”

She’s right. I looked around to see if anyone was looking. Why can’t I do this for myself? “When we first swapped, I was at one of those popup markets.” I told her. “I was browsing women’s clothes. And the look I got from other customers…”

Madison came up to me and held me on my shoulders. “Don’t worry about anyone else. You can do this. You’re a strong woman. And if you need someone to be there for you, I’ll be by your side.”

“Thanks Mads,” I said. I looked back at the rack, picked up the dress and held it back up against me. “Maybe a size larger,” I said. I found a few sizes larger. “Maybe this.”

“Well, try it on.” she said. 

We both walked to the changing room, where I went in and she remained outside.

I took off the coat, t-shirt and jeans and stood there in my boxer shorts. Should I buy underwear while we’re out? I pulled on the dress and exited the room to check with Mads. “What do you think?”

“I like it.” she said. “Though I think it would look better with leggings.”

“OK” I said. “Let’s get some leggings.”

“And shoes.”

“Shoes.” I repeated. “And underwear?” This was exciting. It’s been a while since I went on a shopping spree for myself. This reminded me of old times, and made me feel more myself.

She smiled. “Yes we can.”

“Oh” I said as I was about to turn back into the changing room. “We didn’t get what you came for.’

“This is what I came for,” she said, winking. “For you. To let you know it’s OK to be a transwoman.”

“Thank you, Mads,” I said. “This helps. But we have groceries in the car. Should we get back to your palace?”

“I didn’t get anything frozen,” she said. “You’re fine. It’s just Nicole and Madison shopping. Like old times. Get what you want.”

* * *

After a long day of shopping, we finally returned to Madison’s apartment. I got a few dresses, several pairs of panties, a pair of shoes, a pair of cute boots, and a few bralettes. After that, I was enjoying myself, so I also got some makeup.

We walked through the door, I dropped my bags and Madison started taking the groceries out of their bags. 

“What’s next?” I said.

“Go shower and shave.” she said, still putting groceries away. “We’re having a girls’ night.”

“Yes, ma’am” I said, getting off the couch.

As I passed Mads, she grabbed and pulled me into a kiss. I was surprised, and even more surprised I felt her tongue. Then she pulled away, leaving me stunned and… a little frustrated. “Go shower now.” she said, winking at me.

* * *


It was a casual Friday morning. I spent a good portion of the morning painting, impatiently watching the clock tick. Tyler was set to come pick me up around 2. So I was trying to kill time all morning.

After lunch, I showered and shaved my legs. When I returned to my room, I got one of the new bra and panties I bought when I was out with Hanna. I was putting on a strapless bra because the dress I bought exposed my shoulders. I watched myself in the mirror as I clipped the bra strap. After months of doing this, it feels so natural, and I almost can’t even remember life as a guy. 

I quickly put on a t-shirt and shorts so I can walk out of my room. I still prefer to be casual, but since I cut back the excessive feminine look Nicole used to do, I’ve actually come to enjoy the occasional moments I can get myself all made up. A hint of foundation, some mascara, eyeshadow, lip gloss, there and I’m almost ready for the next step of my transformation.

While I was putting the finishing touches up, out of the corner of my eye, I noticed Lexi was watching me. 

“What’s up?” I asked.

“Nothing,” she said. “I was just thinking how only 2 months ago you were a guy and you had never touched any of that stuff before. Here you are standing there putting makeup on like you’ve been a girl for 20 years.”

Great minds think alike I suppose. “I’ve had help,” I said. “I have some of the best friends a girl could’ve asked for.”

“You just called yourself a girl.” she said. “Are you ready to admit you’re trans yet?”

“I dunno.” I said. “I’ve accepted that we’re not swapping back. I’m a girl on the outside. And yea - I don’t hate it.”

She nodded.

“It’s as if some magical force out there said, you are better off living this life than your old one.” I added. “But what bothers me about that idea is that I’m better off this way. Nicole is not. Nicole got the shit end of the deal. It’s as if… nah forget about it”

“What Vic?”

“It’s as if the wish was only about me. It was never about Nicole. It’s as if I was the one who wished for this… or Tyler.” There was more to this though, but I didn’t want to dive too deeply into it. The implications of this theory lead me down a path I don’t want to go. What if Tyler did wish for this? What does that mean for me? For Nicole? For Tyler? That means Tyler had the Genie at some point. I don’t want to continue this line of thought because the end of it only leads to potential heartbreak.

I returned to my room and I pulled on the dress. I put on a pair of heels. I posed in the mirror. It was elegant. And hot. Damn, I look sexy. 

I returned to Lexi who hadn’t moved from her doorway. “What do you think?”

“Amazing, Vic.” she said. “You’re gonna knock Tyler dead.”

“I’m worried about Nicole.” I said.

Lexi placed her hands on my bare shoulders. “Don’t worry about Nicole tonight. This is yours and Tyler’s night. Besides - she’s in good hands.”

And this was another reason I didn’t want to think about the genie. My reluctance to turn back then makes me out to be the bad guy. I just want to enjoy tonight. It’s Friday, and it’s date night with my boyfriend. Maybe I’ll worry about the genie and real world stuff tomorrow. I smiled and nodded. Lexi returned to her room, and I started doing my hair. This hair has a natural wave to it, but I think I want some curls to lay on my shoulders tonight.

* * *


I pulled my car up to Nicole’s apartment. I got out and stood beside it. I was wearing a gray suit, pink shirt, and light blue tie. I don’t always wear suits, in fact I usually avoid them. But I wanted to make a great impression on Nicole. She makes me want to look my best.

Then Nicole came out of her building wearing a stunning dress.

“You look amazing,” I said.

“Wow,” she said. “Look at that suit.”

From behind my back, I pulled out a bouquet - of snickers bars.

She looked at it and laughed. “You got me a bouquet of candy?”

“I remembered from a few months ago, when I got you makeup flowers and you ate my candy bar instead.”

She chuckled. “That was your candy bar? Well, I remember I was having a rough day and I was hungry and I really appreciated it.”

I opened the passenger car door for my girlfriend.

“Thank you very much,'' she said, getting into my car, and taking the bouquet from me.

I walked around the car, and got into the driver's seat.

“So where to?” she asked.

“You’ll see,” I said, driving away.

* * *


I took a nice long shower. I brought my toiletries with me and slowly shaved my body. The stubble was coming in the past few days and it was certainly itchy and unpleasant. I could smell food cooking. Madison is cooking for me.

I dried off and picked out a navy blue pair of panties and pulled them on. They didn’t fit exactly like I expected. Mostly because this body doesn’t have the hips and this unwanted appendage is there. I flattened out my dick and pulled the panties up snuggly. 

I next put on the bralette. Sure I don’t have any boobs, but the bralette felt familiar. 

Next came the leggings, then the sweater dress, then a pair of socks and the boots.

When I was dressed I went to the mirror and started doing my makeup. I hadn’t done makeup in 2 months, but I most certainly didn’t forget. 

Next was my hair. This body had short hair when I got it 2 months ago. I certainly haven’t gotten a haircut, so it’s a tad longer than it was. I added some product to my hair to try to give it more volume. I played around with it with my fingers. I let some strands fall in front of my ears.

I stood back and admired my work. “Oh my god.” I said to myself. “I look like a taller, more muscular Hanna.” I don’t know what I was expecting. I most certainly don’t look anything like my old body. But coming close to looking like Vicky’s sister actually made me a little more feminine, and certainly made me feel more at home in this body.

When I walked back into the living room, Madison was there, equally dressed up. She was wearing a little black dress with designer stockings. Her heels clicked against the tile floor as she seductively walked towards me, holding two glasses of wine.

“Hello beautiful” she said, handing me a glass.

“Thank you,” I said. “You look gorgeous as always. I’m worried I look like a dude in a dress.”

“You’re a beautiful woman, Nicole. Don’t let anyone tell you otherwise.” 

“So what did you make?” I asked, sipping some wine.

“A Vegetarian Mushroom Risotto.”

“Sounds yummy,” I replied.

* * *


Tyler drove us downtown, and we valet parked at a fancy restaurant I have never been to. It was certainly not a place frequented by college kids. The restaurant was gorgeous. Fancy architectures, high ceilings, elegant chandeliers. I heard music - a live orchestra too.

This time, they had our reservation and we were escorted to our table.

“Wow” I said. “This is something else. I hope this wasn’t too expensive, Ty.”

“I had a Groupon” they shrugged off.

I looked at the drink list. Fancy. I feel like getting a beer likely wouldn’t be appropriate here, so I looked at the cocktails. The waiter came, and I ordered a chocolate martini, and Tyler ordered a jalapeno margarita.

Once the waiter left, I saw an open dance floor where people were slow dancing.

“Would you like to dance?” Tyler asked.

“Kinda.” I replied. “But I suck at dancing. You saw me at Halloween.”

“I loved the way you were dancing at Halloween.”

“But that was pop music. This is… fancy dance kinda stuff.”

They got up, extended their hand, I took it, and they led me to the dance floor anyway.

Tyler placed my free hand on their shoulder and then put their other hand around me on the small of my back. Then they proceeded to slow dance with me, which surprised me. 

“Tyler, have you been taking lessons?” I said. “You weren’t this elegant at the Halloween dance.”

“I found a do it yourself video.” they said. “How am I doing?”

“Great” I said. 

Just then, Tyler twirled me. Tyler sure is finding a way to make me feel like a princess at a ball.

“I love when you smile,” they said.

Was I just smiling there? Surely I didn’t enjoy getting twirled, right? I certainly smiled more at the compliment.

“It makes me feel like I’m finally doing things right.” they added,

When has Tyler done anything wrong? “Everything is perfect, Tyler” I said.

* * *

After a very exotic dinner, drinks, and dancing, we returned to campus. I imagine drinks were expensive, so we didn’t stay at the restaurant long after dinner. But instead of returning to either my or Tyler’s dorm, we walked to the Student Union. The sun was low in the sky and the campus had a serene calm to it. There was certainly a chill in the air that was penetrating my coat. I leaned against Tyler for warmth.

“Let’s go up to the 5th floor” Tyler said, pushing the elevator button. 

“What’s up there?” I asked.

“Nobody” they said with a smirk.

“Oh.” I smiled at the insinuation they wanted to be alone. I don’t know what Tyler was thinking. We can certainly be alone in their bedroom. Or my bedroom. Lexi or Josh can take a hike for a few hours if need be.

We took the elevator and strolled through the 5th floor, which is just a bunch of student club offices and study rooms that were empty for the weekend.

Tyler held my hand and we walked through the empty corridor. We came to what would be the front of the building. A large window was there that overlooked the entire campus. I don’t think I’ve ever been up here. 

There was a strategically placed blanket there with a bucket of ice and a bottle of champagne sticking out of it. 

“Tyler, did you do this?” I asked.

“Maybe.” they said. “Sit.” they motioned. “I’ll take your coat.”

I took off my coat and handed it to Tyler. I then adjusted my dress, and sat down on my knees and Tyler joined me after placing both our coats to the side. I looked out the window. It was a beautiful view of the sunset. The orange glow of the sun, and the late-fall foliage on the trees were breathtaking.

“What’s the champagne for?” I asked. “What’s the occasion? Our anniversary has already passed.”

“This is the three year anniversary of actually making it official.” they said.

“Oh” I said. That makes sense I suppose. “This is so sweet,” I said. I decided I liked being wined and dined. I only ever imagined doing it from the other side, wining and dining with a girl I liked. Of course, I never really got that opportunity.

Tyler reached into their jacket pocket and pulled out a folded note. They cleared their throat. 

“You prepared a speech?” I asked.

They gave me the “stop talking” look. 

Fine. I’ll let them make their speech.

“Nicole, it’s been 3 wonderful years dating you. We’ve had our ups and our downs. You’ve been there for me when I was having troubles and I tried to do the same for you. It wasn’t until just recently that I realized something just clicked into place with us. It felt so natural to be with you. I couldn’t imagine college without you in my life and have a hard time imagining the future without you either.” They refolded the paper and returned it to their jacket pocket. “I taped some of my favorite pictures of us to that window.”

Sure enough. Around the sides of the windows there was stuff taped to it. There was a napkin branded from Birdie’s Wings and Golf, technically my first date with Tyler, then a selfie from that same night. There was a picture of us in our Halloween costumes. Then one of Tyler and I sleeping on the couch after video games that Josh must’ve taken. All of these pictures were from this semester. I expected to see some of Nicole, but there wasn’t one. 

I meant to ask where the older pictures were, so I turned around and Tyler was kneeling beside me. 

“I’ve spent years praying for my soulmate.” they said. “Searching for someone who would accept and love me for me. During one of our fights at my lowest, I made an offhand wish that I’d find my soulmate.” 

Tyler made a wish? The wish?

“And since then, every moment we’re together, you’ve constantly reminded me that I already found you. You are the perfect girlfriend.” They pulled out a box from their jacket and opened it to reveal a ring that stopped me from breathing. “Please be the perfect wife.” 

All thoughts about the wish stopped. My eyes got big. My jaw dropped. Oh Shit. I’m dreaming right? No way. Tyler’s proposing? To me? Should I follow up on that wish comment?

It was a modest ring - but what do I know? I know nothing about rings. I never owned one in my life. But Tyler is giving this to me. My first ring. My first ring is an engagement ring.

What am I going to say? Tyler’s proposing to me. Tyler wants me to be their wife. Sure I was imagining being someone’s husband one day. In fact I had considered proposing to Lindsey before we graduated. I had started to look at rings before she dumped me for my best friend. All of my hopes and dreams for us, shattered. Tyler is offering me what I lost. I hadn’t considered being someone’s wife. But slowly I’m being drawn to that sparkling ring. Is this what I want? I’ve accepted that I may stay as Vicky for the foreseeable future. I’ve accepted that I’m going to remain living this life. Sure, I certainly wasn't happy being magically put into Nicole’s body, but Tyler has made every day bright and sunny. I’m having a hard time imagining a future where Tyler’s no longer in it. The thought of returning to my solitary life as Victor is unappealing. Tyler is the reason I don't want to be Victor anymore. 

“Yes, Tyler” I found myself saying.

Is this really happening? I just said yes. I’m engaged. The past two months have felt like a dream. Is this part of the dream where I wake up? 

I was stunned and frozen. Tyler took the ring out of the box and held it up to me. I took it. Which one is the ring finger? Left hand, right? I slid the ring onto my left ring finger and it fit perfectly. The diamond sparkled under the light from the sunset behind me.

I felt tears on my cheek. I wiped them away. Gah, why do girls cry when they get proposed to? Why am I crying? I’m happy. I’m overjoyed. But there was a nagging thought in my mind. I never told Tyler I was Vicky. I should’ve told them before they proposed.

Tyler is proposing to the wrong person. No. Bury that thought. Look at those pictures. Tyler is proposing to me. To Vicky. I’m the one they fell in love with. Tyler - wished - for - me. I’m the one Tyler wants. This is right.

“What’s wrong?” Tyler asked.

“I’m just happy.” I said. I am happy. But I never told them the truth. Can I even tell them the truth now? Can I take this ring off and give it back to them? 

No. I don’t want to. This is my ring. Tyler is my fiancé. This felt right.

And with that thought, it was crystal clear. I wanted to marry Tyler. I wanted to be their wife. This is the future I want, and dammit I’m going to take it and protect it.

I embraced Tyler and they kissed me. “Yes, Tyler. Yes I’ll marry you.”

* * *


After an amazing dinner and 2 bottles of wine, Madison and I were cuddling on the couch listening to some jazz she put on.

I kicked off my boots and feet up on a nearby ottoman and she did the same. I then removed my socks so I could show off the pink nail polish on my toes. 

Her stocking foot started playing footsie with my bare foot. I giggled when she started tracing her finger up my legs. 

I turned to her. She had a hungry look in her eyes. She held me tightly. There was nowhere to go. But I didn't want to go anywhere.

I looked into her eyes and offered my lips with a whimper. She pulled me in for a kiss and I offered myself to her.

I felt her hand go up my dress and to my thigh. I could feel her fingers slightly caress my thigh through my leggings. At that moment I wanted to shed them.

She got up and straddled me without releasing our kiss. I was hoping my erection wasn’t ruining the mood.

She grabbed my left breast. Despite nothing being there, it felt weirdly euphoric. Her touch is reminding me I’m a woman.

She broke off our kiss for a moment as she then lifted up her dress over her head and tossed it aside. 

I placed my hands at her hips and I offered up my lips once more.

Instead, she unclasped her bra and tossed it on top of the dress. Then she offered her right breast to my lips. 

My lips met her nipple and I let it on my mouth. While I was expecting her lips to meet mine, I wanted any part of her she was willing to give me. I then started caressing it with my tongue. I hoped I was doing this right as I only ever had this done to me. When I heard Madison let out a gasp, I knew I was on the right track.

Madison was completely in control, and I was loving every moment of it. Gone are the days of me having to dictate what Tyler did in the bedroom. Madison pulled away only to offer me her other breast and I gladly complied. “Good girl,” she said.

I moaned at that and continued to happily suckle on her.

She pulled away then put her hands under my sweater dress and started pulling it up. After she did that I crossed my arms over my flat chest out of embarrassment. 

“It’s OK.” she whispered, rubbing my bare arms. She knew I was self-conscious about this body. “You’re beautiful, and you’re mine tonight.” Instead of removing my bralette, she instead tugged on it and pulled my left breast out of it. It wasn’t much, but having my one breast being pushed up by the bralette made me feel like I had something to offer her. She then suckled at my exposed nipple.

It felt weird at first. Nothing like it did when Tyler used to do it to me. But slowly it started to feel good. Before I knew it I was moaning. I wanted more. 

And Madison happily provided, moving onto my other breast. After a minute of suckling on that breast, she returned to my needy lips. She pressed against me, our bare breasts touching each other.

I ran my hands up her stockinged legs over her panties and up her bare back, then back to her thighs.

She grabbed one of my hands and placed it between her open legs.

I got the message. I took my fingers and started rubbing her panties. I looked into her eyes for validation. She smiled and let out a moan. 

I felt her thrust her pelvis into my fingers, as she started kissing my neck and ears. Her warm moans on my neck made my fingers work faster.

Her moans got faster and her legs squeezed me. She suddenly stopped me and stood up. 

Did I do something wrong?

She held out her hand. 

I took it, she pulled me off the couch and led me to her bedroom.

When we got to her room, I slid off my leggings and kicked them free. My erection was clearly tenting up my panties, but Madison didn’t seem to care about it.

She pulled off her pantyhose and panties and sat down on her bed. She leaned back with her legs spread open. She looked at me with a smile and traced her labia with a finger. “You want dessert?”

I silently nodded and I knelt down and moved my way to the bed and her. 

As I buried my head into her pussy I was rewarded with her saying “good girl.”

This was certainly a side of Madison I hadn’t seen before, but her dominance was turning me on. I wanted to obey and pleasure her. I’ve known Madison since the first week of school freshman year. She’s been one of my best friends since then. Our friendship was always based on mutual respect and love. I would always meet her flirtations with resistance. It felt so good to break myself of that resistance and fully let her in. 

I’ve dreamt of going down on another girl since I fooled around with Brianna. We never made it this far, but we definitely did over-the-clothes petting. This felt like a dream. Madison has been a lesbian the whole time, but I tuned that part of our friendship out. She has certainly dated people over the past years. She never brought them around and I never asked their names or their genders because I didn’t want to know. I suddenly got nervous that my limited experience wouldn’t compare to her previous partners. 

I had only been on the receiving end of this. Tyler certainly knew how to make me feel good. I can only hope to replicate that feeling in Mads.

Madison smelled sweet. She was already wet and her folds were exposed and tempting me. I used my tongue and tasted her sweet juices. I was hooked and used my tongue to trace and massage her folds, lapping up every drop of juice I could get.

I could hear her moan. I was doing a good job and that made my erection throb even more. I was tempted to use one of my free hands to masturbate, but I resisted, instead seeking to give all of my attention to Madison’s pleasure, not my own.

She grabbed my hair as her moans got louder. My tongue was cramping up, but I wanted to continue to pleasure her.

She tensed up and came. She sat up and pulled me up on the bed with her. She kissed me passionately to reward me for doing a good job. 

She then forcibly pushed me down onto the bed.

I went to remove my panties to free my dick, but she slapped my hands away.

She then straddled me and kissed me. I felt her start to grind up on my erection on top of my panties.

Oh this felt good. I could feel my own panties getting wet - either from Madison’s juices or my own precum. It was then I felt my erection spring free of the panties. 

She stopped, pulled out a grocery bag sitting on her floor. I recognized it from earlier in the day. She pulled out a box of condoms from it and made quick work of the packaging. 

I went to remove my panties but she stopped me again. She wanted me to keep wearing my bralette and panties. I have to admit, it certainly helped keep me in the mood. It kept me immersed as Nicole. As a woman. Where I felt dysphoria having sex with Kayla, with the wrong body and the wrong sex parts, I felt like Madison was calming those thoughts. Perhaps I’m not the first transgender woman Madison has hooked up with.

She then grabbed my shaft and rolled the condom down it. Her confidence was comforting, since I felt embarrassed when I put one on my first time with Kayla.

I was afraid she wouldn’t want to have sex with this male body. But clearly she prepared for it. I didn’t have to be embarrassed anymore. She wanted to have sex with me as I am.

She then continued grinding against the shaft. It was slow at first. I noticed when I had sex with Kayla how muted the sensations were behind a thin wall of latex. She started to pick up speed, and I could feel the orgasm coming.

“Not so fast” I said between moans. “I’m close.”

Then she backed off and slowed down. She paused and focused on kissing my lips, my neck, my ears, my nipples.

She slowly started grinding against me again. This time she was higher on the shaft. I moaned more as this felt really good. She stopped, and continued to kiss me. I could feel the head of my dick find her opening. Every twitch of my dick would slowly inch into her. Twitch. Slide. Twitch. Slide. Inching in bit by bit.

Then suddenly I felt my full dick slide into her. I expected her to pull out, but she slowly rode me. 

I was in ecstasy. She went slowly enough for me not to come right away and enjoy it.

Then she pulled out. My eyes pleaded for more but she got off the bed and went into her dresser drawers. 

I sat there on the bed staring at the ceiling in frustration. I wanted more.

“Get up” she commanded me. “All fours.”

I looked up to see Madison standing there wearing a strap-on dildo.

My eyes got wide. I did what she commanded. I stared straight at the wall as the plastic dildo slid into my ass.

Minutes later I was screaming in ecstasy. I loved every second of it.

* * *


“How did you get all of this done?” I said, amazed at everything. This place, the setup, the dinner, the ring.

“I had help,” Tyler said. “Josh, Lexi, Madison. They all helped me.”

“They all know?” I said surprised.

“Josh told me about this spot. Lexi made sure the ring was the right size. She was also very maternal I might add. She sat me down and gave me a whole speech on making sure I was going to treat her roommate right. The restaurant was Madison’s idea.”

Another tear. I wiped it away. “I certainly have some great friends.” I’m so overjoyed.

Tyler pulled out their cell phone. “Let’s get a selfie.” 

They held out the phone and I smiled, holding up my left hand with my engagement ring. After Tyler took the picture I looked down at the ring on my hand. What a magical night this has been. I have the best friends and the best fiancé one could ask for. 

* * *


It was dark in Madison’s bedroom. She was spooning me as I was coming off of a sex fueled high. My breathing was still returning to normal. I heard Madison’s phone buzz on the nightstand next to the bed. She reached over and glanced at it.

“What’s up?” I turned and asked.

“Nothing,” she said. “I’ll tell you tomorrow. Come here,” She offered her embrace and I slid into it. When my breathing returned to normal I dozed off. Things are good in Madison’s arms. I feel like maybe things are going to get better.



Hi, I'm Emily and I'm writing Gender Transformation Fiction! This site is a place for me to keep all of my stories in one place. I'm also a software developer in the daytime, so this site will also be a proving ground of cool new features that pop into my head. Feel free to message me on Twitter or at my Discord Server! You can also find me on and

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She is going to be despondent when she finds out. Also I half expected then to switch back suddenly during their dates

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She's going to be something alright!

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“I feel like maybe things are going to get better” That won’t be contradicted in the next chapter… not a chance…

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Famous last words!

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I have to say I expected TayTay to propose to 'Nicole' but not with all the effort they put into it. Real class act on T's part. There was just too much leading up to tonight to not have a proposal. Romantic evening, private chat with parents, nice restaurant. The room overlooking the campus at sunset was perfect. Assuming T finds out they aren't engaged to Nicole v 1, how hard is Nicky going to have to work to earn the right to replace Nicole in T's life? Can they reach a point where T will weigh the betrayal against all the good Nicky brings to the relationship and decide to continue with her? I suppose a lot of it will depend on how happy Nicole can be with her circumstances. If Nicole is miserable, that would also pull T down emotionally. It seems, fortunately, that Madison is willing to go all out to make things work with Nicole. I'm glad to see Nicole is in a serious relationship, even if it is not with T. I didn't think Stephanie was all that bad a person either. And of course, Kayla. At least Nicole doesn't have to be alone, even if she can't be with the one she wants. (Hey, I feel a song title coming on...) The hot monkey sex with Nicole and Mads was a little edgy-er than what you usually write. But you pulled it off very well. I was not expecting the strap-on part of the play. Then again, based on Nicole's reaction, I don't think she was either. I was more-or-less expecting just the typical biological body Olympics between a boy body and a girl body. I do hope Nicole is willing to experiment more with being a boy before totally giving up. She has been more focused on the negative aspects for the last two months. I might be biased, but being a guy isn't always bad. Mads is treating Nicole very, very well right now. That might make her feel better about being stuck in the icky boy body. Maybe there is a happy ending for everyone (except Brandon). He gets 💩 So do Nicole's parents. And I really hope Nicole can find it in her heart to give T and Nicky her honest and heartfelt blessing on the nuptials. Let's face it, Nicky and T are much more suited for each other than Nicole and T. And deep down I think Nicole knows that. She needs to let go of T and focus on Mads. Sorry, I know that is harsh, but it's like ripping off the band-aid. Better to get it over with and start healing. So at this point, with the engagement, how would a scene play out in which Nicole and Vicky confess to T? I'm picturing four possibilities: 1. A gathering at T's place with everyone who knows about the swap. Even Courtney. Nicole and Vicky need to sit down with T privately and explain what happened, when and how, as best they know. Then give T time to ask questions and process the information. Expect some anger and resentment. T's friends are there to show love and support as well as to verify the swap claims, however T chooses to engage with them. 2. Just T, Nicole, and Vicky. Again, expect the emotions, but maybe the more intimate setting will give T less shame to feel of being betrayed. 3. Just T and Vicky. T will have to reach out to Nicole for her side of things, and I'm sure Vicky will have to tell Nicole in advance so she isn't blindsided by T calling her or showing up in person to hear her side of things. 4. The secret dies with Nicole and Vicky. T never finds out (hopefully). Everyone else just lets the story die and moves on. T doesn't get hurt, Vicky gets her dream guy, and Nicole moves on with her life as well. Seems like a total cop-out, but results in fewer broken hearts. Problem is, Brandon is a big unknown in all of this. He could somehow let the cat out of the bag about Nicole and Vicky to Tyler, even if it is just out of spite. I'm trying to think through how I would react if I was T being told the truth at this point. Extreme disbelief, because magic doesn't exist, right? (That's where the others, especially Courtney can help.) Followed by anger, humiliation, betrayal. I'd need both Nicole and Vicky there together to confirm the claim. I would expect them both together, although I could see Nicole feeling too ashamed to face T. It was her idea to keep the secret from T in the first place. I know, Vicky isn't far behind in going along with the whole scheme. Afterwards, some alone time for T to process? Or is that the right time to say goodbye to Nicole? Then T can very slowly start to rebuild trust with Vicky? The longer T is kept in the dark the harder this moment will be for them. I'm also assuming there is no way to swap back at this point. And even if it was possible, Vicky wouldn't be willing to swap back. How far would she go to remain in Nicole's body? People in stories have resorted to murder to keep what they have. Or would Vicky do the 'honorable' thing and swap back out of obligation? Now that brings up another interesting situation. With Taylor in the picture, after swapping back Victor could still have a loving marital relationship with the person of his dreams. Nicole is still SOL with T, however. And at the end of the day, magic is involved. We still don't know how many wishes have been made and how they have affected each person's life. We don't know motives or long-term goals. Even memories are suspect. Nothing is off the table, yet. Looks like you've got quite a job ahead of you, Emily, to put all of the pieces of this puzzle in place, on at a time, without letting on the bigger picture we are trying to solve. Good luck with your writing. I hope this review provides you with encouragement, but doesn't steer the USS Emily towards a literary iceberg. Write everything so that you are happy with it. M101 is your creation, and you have made it come alive in amazing detail and emotion. Great job.

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Sorry, I actually had my review broken down into those things called, um, paragraphs. I forgot they don't travel well and everything gets jumbled together. I can't even go back to edit or delete. Looks like you're stuck with the giant blob review. Sorry.

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