The year after I graduated college I lived with a guy named Blaine I found on Craiglist while searching for places to live. Just hearing that name you might think "douchebag" and you were right but he had an extra room and I did NOT want to live at home.
This guy was drunk all the time, messy as hell and really mean to any girl he would bring back to our apartment. Recently it was a girl named Lexi, she had only been around a few times and I could tell she wasn't very interested in him. He would get a little rapey at times, touching her when I was around when she was clearly uncomfortable. I tried giving her looks of apology for my idiot roommate's behavior but she didn't care, she ignored him most of the time and I could tell she was ready to be done.
There was one Tuesday where Blaine was at work and I had the day off. He and Lexi had spent most of the weekend fighting about how she wouldn't have sex with him. It seemed like this was the typical "girl tries to fix the ass-hole" relationship that was clearly not working at all. I slept until about 10:30 a.m. and when I left my room, I noticed that Blaine had left his door open and there were a few articles of Lexi's clothes on the floor including a black lace thong.
She was gorgeous and just seeing her clothes started to get me a little hard so I decided to try them on. Her thong slipped on perfectly, hugging my junk into one little soft piece of fabric and sliding right up my crack for the perfect fit. Next it was a pair of black Lululemon leggings, a perfect fit as well, molding my nearly non-existent ass into a cute little bubble butt and slimming my legs all the way down to my ankles. I was loving my waste-down girly look and had just put on her baggy sweater when I heard the front door open.
Terrified, I tried to find a place to hide but it was too late, Lexi stepped in the apartment and had a clear line of vision towards me wearing her outfit from the previous day.
"Uhhhh, what the fuck???" she said, closing the door behind her. I was nearly speechless, stammering to get the right words out.
"You weren't supposed to be here" was all I could get out.
"And you're not supposed to be in my clothes but here we are," she said. I was frozen, without a clue in the world. "Looks good on you though, if I doll you up enough you may be able to pass as a girl."
"Huh? If you what??"
"Yeah, come here, let me fix you up," she came into the room and took my hand. "You can't wear those cute leggings without a pair of Uggs sweetie." She grabbed the boots out of the closet and handed them over. I was hesitant but I pulled them on and they fit perfectly.
"Next we'll work on your upper body. Take that sweater off and put in this," she reached into the closet again and pulled a corset off a hanger. She held it while I stepped into it and tied it up tight for me then took some tissues and stuffed the bra cups. "Perfect, now you can put that sweater back on and have a seat on the bed." I started to ease my way onto the bed but she pushed me down.
"Makeup time!" The next few minutes were a blur of brushes and pencils and an array of colors. She had a few different cosmetic sets in her giant purse and it felt like she was using everything. "And now for the finishing touch." She reached into her bag and pulled out a blonde wig.
"I usually wear this when I go out to bars just for fun but today it's for you, sissy!" She pushed my hair around a bit and slid the wig on. "Excellent! We just need to get you pumpkin spice latte and you'll be my perfect basic bitch." She laughed and asked if I was ready to see myself in the mirror. I nodded and she pulled me up from the bed and walked me into the bathroom.
"Oh my god!" I said, staring at a beautiful blonde girl in the reflection. "I'm...gorgeous!" It was too good to be true, my makeup was a little heavy but it was perfect, the wig looked natural and I had perky breasts showing under the sweater.
"How do you feel?" she asked.
"Amazing, I've always wished I could try out being a girl!" I said. Her excitement turned to confusion.
"You don't sound like a girl sweetie, want to try that again for me?"
"I feel incredible," I said with a bit of a higher pitch.
"That's better," she grabbed my hand and pulled me towards the front door. "Let's go sissy, I need some coffee so we're going to Starbucks so you can get your basic bitch pumpkin spice latte too."
I tried to pull back but she was not letting go. She dragged me into her car and put me in the front seat. Our drive was very short and I expected us to go into the drive through but she parked and got out of the car. She walked around to my side, opened the door and pulled me out.
"We're going inside and you're going to order a drink."
The place was packed but there wasn't any line. I felt like everyone was staring at me, knowing there was a boy under all the clothes and makeup but my fears would soon be quelled.
"One pumpkin spice latte, extra whip," I said in my best female voice.
"OK Miss, and what's your name?" the Barista asked, pen in hand ready to write it on my cup. I had never thought I would have to come up with a girl's name for myself and I couldn't say my name was Derek, that's not feminine at all. "Um, Daria," I said.
"Like the TV show?" said the Barista, I nodded and gave a half-smile. "I used to love that show!" He started going on and on about one episode that I never even saw and eventually I could tell this guy was flirting with me.
I was dressed like a girl, I felt like a girl and this guy was treating me like a girl. I looked back at Lexi in disbelief, she gave me a look of "I told you so" then ordered her drink and paid for both of ours.
The Barista was still trying to talk to me while we were waiting for our drinks. I could tell he thought I was really beautiful and until that day had never really felt any sort of sexual interest towards a guy but in my girly state I couldn't help but feel a little attracted to him.
Our drinks were finally ready and we took them back to the car. "So, did you get his number??" I couldn't tell if Lexi was being sarcastic or not but I told her I didn't and that I wasn't interested in guys. "He was SO into you, how could you leave him hanging like that?" It felt like she was starting to get mad now. "I'll have to teach you a lesson when we get home then."
We pulled back into the complex and got out of the car. I had a newfound confidence and didn't feel like Lexi had to drag me around everywhere. I saw a guy I knew checking me out on my way inside when he was taking out the trash. He had no idea it was me!
Inside Lexi pulled me into my bedroom and shut the door. "What the fuck were you doing in there?? I brought you to that store and pushed you to get that barista's number so we could have a fun sissy threesome but since that obviously doesn't interest you, it'll just have to be you and me."
"What?? Threesome?" I was confused.
"What? You think I dolled you up like this just so you could play dress-up? I turned you into a girl so you could be my little fucktoy and I WANTED to bring a third into it but you're too sissy to play ball so instead of his cock, you'll be sucking mine now." She pulled down her own leggings to reveal a soft, cut, four-inch shecock.
"You're trans? Wow, I would have never known."
"Sure am sissy, why do you think I'm so good at getting a boy to look like a girl? Now get to sucking." She pushed me onto my knees, grabbed my head and pulled it towards her. I took her hands off of me and she gave me a very angry look.
I inched closer and softly kissed her tip. Before I knew it I had the whole thing in my mouth, tongue swirling around while she moaned for more. I started to squeeze her ass and it felt incredible but as soon as I had a handful, she grabbed my hand and pulled out of my mouth.
"Enough sucking sissy, I don't want to waste my orgasm on your sloppy blowjob. It's like you've never sucked tranny cock before." I hadn't and I could tell she was being sarcastic. "Now get on the bed and get on all fours." I followed her direction and she pulled my leggings down my thighs to expose my ass. She grabbed some lube from her giant purse (of course) and started playing with my ass hole.
"I need to make sure your sissy pussy is nice and wet for me." Her fingers teasing the outside and slipping in just a little. She leaned over me and whispered into my ear, "you might feel a little something back there." And I sure did. Her rock-hard shecock slid right in and a euphoric feeling came over me as I moaned for more.
She started thrusting harder and faster, I tried to ask her to slow down but it felt too good to speak. She could see me getting hard and grabbed my cock and started stroking.
"We're going to cum together baby, are you ready?" I tried to squeak out a yes but it didn't happen. I just moaned louder and started cumming all over my bed, I could feel her throbbing and shooting cum into my ass. She pushed me down so I was flat, thankfully out of the way of the large cum pile. She pulled out let all her cum leak out my ass.
"Mmmm, good job sissy," she said. And with that she was gone. I don't mean she left, she fucking snapped her fingers and disappeared. I got a very disorienting feeling, my vision started to blur and I got a weird feeling in my stomach. I must have passed out because when I came to it was about two hours later and there wasn't any cum on the sheets. I looked around the room, everything was different. It was like I was sharing the apartment with a girl.
There were a few photos on the dresser and I picked one up, hoping to answer some questions. I looked at the picture and almost passed out again. It was me but it was girl me kissing the barista. All of the pictures were of girly me and him. I reached for my hair, thinking it was a dream and I could pull the wig off and be me again but I couldn't. It was long blonde hair but it was mine. I pulled my leggings down, hoping to untuck my penis but it wasn't there. I checked the padded bra but it was filled with skin, with breasts. I had become female.
I began to become more aware of my surroundings, my body was shaped a bit differently, and without even trying, I sounded like a girl. A lot of the stuff in the apartment was still the same but slightly different. Pink cups instead of blue, Cosmopolitan magazines instead of Sports Illustrated. I ran to the bathroom and looked in the mirror, everything looked real, it felt real. I even had texts on my phone from friends and family as if they knew I had been a girl this whole time. It was like having sex with Lexi transported me to a dimension where I had been born a girl.
My mind started racing when the door opened. "Daria! I'm home, where are you?"
"In here" I shouted from the open bathroom with my newly normal feminine voice. I started brushing my hair so it looked like I was in there for a reason. Soon I smelled coffee and felt lips on my cheek as he gave me a kiss and placed a latte in front of me. A rush of love and attraction came over me, my final hint that I had truly become female.
"Pumpkin spice, your favorite!" he said, squeezing my ass. "Oooh, nice leggings, are those new?" I nodded, he smiled. "Oh, we also had one of our regular customers bring us a bunch of fortune cookies so I brought one home for you too." He placed the wrapped cookie on the counter and walked into the bedroom.
I unwrapped it, broke it open and pulled out the fortune. It had a haunting message that felt like it was just for me, "Some days you live your life in peace and some days you get fucked by the Devil."
I went to sleep that night thinking I would wake up a boy again but it didn't happen and it never happened.
