So here I sit, waiting to hear what will become of me, and I can’t help wondering how the hell I got here. I know how it all got started. And it was all Michael’s fault —
Michael and I met my first year of high school. We were both the smart nerdy types. And at around 5’6″ and just over a 100 pounds, with long hair neither of us were exactly the jock type. Michael’s dad split when he was young. His mother remarried, but his step-dad Brent spent most of his time in China running some sort of import business, so his Mom, and older siblings, s****r Brittany and step-b*****r Derrick, pretty much had the house to themselves.
His mother worked late, and his b*****r and s****r both had jobs. So we often had the run of the house for several hours after school. Neither one of us had much of a social life, so not much need for a job, We’d watch moves on cable, or play video games like Soul Caliber, I was always too afraid to play the female characters around anybody but Michael for fear that someone would accuse me of being queer. But Michael always seemed comfortable playing them, so I did, as well. This had pretty much been our routine since middle school. Not far into our senior year, at 18 years old, we were still each other’s only real friend.
We’d always talk about girls being hot without realizing that we both longed to be hot like them…until the day I let it slip, that I thought Bridget Moynahan was…
“…So hot in Coyote Ugly. God, I wished I looked like her!”
Michael stared at me for a second in surprise. I thought, Oh shit…I can’t believe I just said that. He got up and disappeared into his room. I’m thinking he’s completely freaking out.
“Andy, come here a second,” Michael called from the other room.
I approached cautiously. Was he lying in wait with a baseball bat the brain me with? I rounded the corner to see him sitting on his bed with his laptop. He waved me over.
“Check this out.”
He was being way too cool about this. I sat down next to him, and he showed me this video of a smokin’ hot girl dancing in a bikini for the camera. He hands me the laptop, and I watched as she removed her top to reveal perfect perky breasts, she spoke in a foreign language that I thought might be….
“Spanish?” I asked.
“Portuguese…she’s Brazilian,” Michael said.
I continue to watch as she pulls her bottoms down to reveal a 7 inch cock.
“What the….?” I gasped.
“Hot, huh?” Michael replied.
He closed the video and opened a folder full of movies.
“I got a a ton of videos like this. Trannys rule!”
I stared at him in disbelief.
“Go ahead,” He insisted, “Check ’em out. I’m gonna grab a coke. You want one?”
I nodded as I clicked on hot tranny movie after hot tranny movie. I lost track of time as I watched almost every movie he had. I was so completely astounded by their beauty, and was incredibly turned on.
“So what do ya think?” a female voice asked.
I looked up, startled to see a very pretty blonde girl in pigtails and a very slutty version of a school girl outfit standing in the doorway with a can of coke in her hand. I quickly closed the laptop and tossed it on the bed next to me.
“Um, I’m sorry I thought you…Um, I’m a friend of Michae…”
The girl burst into laughter.
“Andy, it’s me,” She said.
“Me, who?” I asked, confused.
“Michael…well when I’m like this…It’s Michelle,” She said.
My jaw dropped.
“Holy shit, you’re fucking hot!” I hiccuped.
Michelle smiled, and approached.
“You still want this?” she asked, as she held out the coke.
I couldn’t take my eyes off her. I reached numbly for the coke. Her eyes, moved down to my crotch. I was hard as a rock.
“Looks like there’s something else, you want,” She said coyly.
I blushed and looked away. Michelle knelt down in front of me, and began rubbing my crotch. She looked up at me and pouted.
“You want me to take care of this for you?”
I stammered, and then nodded…unsure. She undid my pants, pulled out my cock, and gently began sucking me off. It was the most amazing feeling in the world. I came in her mouth almost immediately. She swallowed, licked her lips and smiled.
Dizzy, I nodded.
“Oh, my god,” I gasped.
“Your first blow job?” she asked as she did my pants back up.
“But hopefully not your last,” she smiled.
As I looked down at her breasts poking out of her top, I was in awe. They looked so real. I reached down and felt them. She grabbed my hands and pushed them together and massaged her tits with them and moaned.
“Awesome aren’t they?” She moaned.
“Silicon breast forms. They’re glued on,” she said.
She got up and sat on my lap, and played with my long brown hair.
“Do you want me to show you how?”
“You mean, with me?”
“I’ll make you into the girl you’ve always wanted to be,” she whispered as she twirled my hair around her finger.
I gulped and nodded. She took my hand and led me to the bathroom. She told me to get naked. She shoved me into the shower, and had me shave everything, legs, arms, armpits. When I got out. She dried me off, and got a pair of tweezers out to shape my eyebrows. I pulled away.
“Wait, what about school, and my folks?”
“Dude, nobody pays any attention to us at school. But don’t worry, I won’t go crazy, besides everyone will just think it’s some kind of emo thing.”
Michelle shaped my eyebrows and did my makeup, then curled my hair. I wanted to look in the mirror, but it was fogged up. She led me naked to her s****rs room. I stood there, as she pulled a bunch of outfits out and held them up to me. She giggled as she scooped up the pile of clothes and ran back into her room dragging me behind her.
In her room, she went into her closet and pulled out a pair of breast forms.
“These are B’s. I had these for awhile before I got the bigger ones.”
“Does your mom, know about this?”
“Yeah, she’s totally laid back.”
She held them up to me, and moved them around on my chest till she got the placement right.
“Here, hold them in place here.”
I did as I was asked, and she pulled out the glue. I backed up.
“Wait how long does the glue last?”
“About a week, but don’t worry, I have remover, it’ll take ’em right off.”
I was scared but excited at the same time. She pulled the breasts away from me at the top and squirted the glue in, and pushed them back into place, and smiled as I held them there, and she gently pushed her pretty painted nails around the edges to the seams to seal them. After about 2 minutes she let go, and so did I. The breasts pulled down under their weight but held. I had boobs! Michelle got some makeup powder out and took the shine off and then they looked completely real. She glued shiny pink acrylic tips onto my nails
She handed me a pair or white thigh high stockings with little pink bows at the top. I slid them on, and they felt so weird, but so good. Next was a lacy light pink pair of waist hugger undies, and a pink chiffon layered mini skirt, and a beautiful ice pink corset. She pulled the laces tight, and the firm caress of the corset felt amazing. She tied the laces off, and wrapped her arms around me, I could feel my cock bulging against the panties. The last thing was a pair of clear lucite platform heels with an open toe. I nearly toppled over trying to stand in them.
She finished by tying my hair back with a pink ribbon. She tousled my hair a bit, and smiled.
“Perfect. You are dazzling,” she said as she pushed her closest door closed, “Look…”
I turned around so I could see myself in the full length mirror on the door.
I gasped in awe. Where did I go? There was a drop dead gorgeous hottie where I used to be.
“Something’s missing,” Michelle said.
She walked back to the bed and rummaged through a pile of bracelets and necklaces. She finally stopped, grabbed something pink and walked over behind me.
“This should do it.”
She wrapped a pink patent leather collar with a heart-shaped ring in front around my neck and buckled it in the back.
“It’s more of a bondage collar than a choker, but it’ll work.”
“So, does this make me your bitch?”
“Definitely,” Michelle giggled.
I was so turned on I could barely contain myself. I kissed Michelle passionately and felt her up. She returned the heat. She shoved me back onto her bed, and attacked me. Her hands were all over me. Her touch against the boning of the corset and along the length of my stockings made me think I would burst. And then she stopped, stood up and pulled her cock out of her panties.
“Your turn,” she said as she shook her engorged cock at me.
I hesitated. I didn’t really want to. I stood up and tried to say no, but all that came out was a stammering mess. Michelle grabbed me by my hair and yanked.
“It’s either going in your mouth or your ass…pick one, bitch!” Michelle snapped.
“Okay, okay,” I squealed.
She let go. I slowly got on my knees and took hold of her little monster, looked up at Michelle, and gulped…pleading with my eyes that this was a joke…that any second she’d start laughing and tell me she was k**ding.
“Don’t act like you don’t want it….suck it.”
I wrapped my lips around her cock and started sucking tentatively. She put her hand on the back of my head and pushed me down on her further.
“Just pretend it’s your own cock. Suck it like you want to be sucked.”
I closed my eyes and did what she said. I licked the head, and swirled my tongue around it as I moved up and down on the shaft. Michelle groaned and gasped in response. As her moaning got faster and more intense, she grabbed a fistful of my hair and fucked my face. I had lost all control to her. She finally reached climax and pulled out and shot it all over my face.
“There, now you know what it really means to be a girl…used.”
Using her penis, she rubbed the cum all over my face and stuck it back in my mouth. I felt like crying…for about 20 seconds. I wiped the cum out of my eyes, and opened them to see Michelle’s mom standing frozen in horror in the doorway.
“What the fuck, Michael?” Michelle’s mom asked.
Michelle stood there casually. Like it was totally normal for us both to be dressed like whores sucking each other off.
“Mom, don’t act all shocked. You’ve never had a problem with me dressing.”
“Yes it’s okay privately, but now your doing it front of a girl…and….does her mother know she’s over here?”
Michelle looked down at me and then back to her mom, and laughed. Her mom scowled.
“This is funny to you?”
Michelle collapsed on the bed laughing. I looked bashfully at the floor and tried to wipe all the jizz off my face. Her Mother turned to me.
“I’m sorry dear. Sometimes Mikey has terrible manners, I’m sure you’re embarrassed enough. What’s your name, sweetie?”
She didn’t recognize me. I must have looked like a deer in the headlights. Michelle giggled.
“Go ahead sweetie, tell her your name.”
“Okay, Andi…you can use the bathroom down the hall and get yourself cleaned up.”
I got to my feet, and went to leave, when Michelle completely lost it.
“I can’t believe she doesn’t recognize you!”
Her mom stopped me in the doorway, and gave me a good once over. After about a minute her face went white.
“Andy Lembke??” She gasped.
I nodded, embarrassed.
“Holy shit, Mike! Do you have any idea how much trouble I could get in, if her..er…HIS parents found out what was going on over here? I indulged your dressing because I believe you should be allowed to be comfortable in your own home without judgment, but THIS?? ”
“Relax, mom. Andy and I are both adults now. Besides, how would they ever find out? It’s not like he’s is going anywhere dressed like that. Although, he does make a very convincing chick. Maybe I can take him to the prom this year.
“Whatever…just get yourselves cleaned up before your s****r gets home, and you and I will have serious talk about this later!”
She stomped off. Michelle rolled her eyes, and bounced up off the bed.
“C’mon slut, let’s turn you back into a boy.”
She took me by the hand to the bathroom to change. We both stripped down to our panties, and I wiped the cum off my face with a damp cloth, as Michelle searched her bag of goodies for something. She removed a squeeze bottle labeled adhesive remover, popped the cap and squeezed some out into her hand. It sputtered a bit. She rubbed it around the edges of her breast form, and began peeling the edges up, she worked it for a bit and eventually got the left form to come free.
“I wish we didn’t have to take these off. I love the way they feel,” I said.
“I knew you’d like it,” She grinned devilishly.
I smiled back sheepishly. She squeezed more onto her had for the other breast, very little came out. She looked at me worried. She tried to get more out of the bottle, but nothing came out.
“What?” I asked, worried.
“Well what does that mean?”
“Well, it means you’re stuck here till tomorrow and the stores re-open. We can go to the specialty shop downtown to get more.”
“I can’t be stuck like this, Mike!”
Michelle slapped my face hard.
“Don’t call me that. I hate that name. Do I look like a Mike to you?”
Even with only one breast glue on, he still looked more like a girl than a guy. I apologized.
“That’s better. And you’re not in this alone, I’m stuck too. We’ll be fine, it’s just one night. No one will ever know. Derrick will probably be gone til Sunday, crashed at some chick’s house, and I can handle Brittany.”
She looked down at the breast form in her hand.
“I suppose I better make them a matched set.”
She picked up the glue, and started smearing it on the breastless side of her chest.
We dumped Brittany’s clothes in the hamper. Still in our panties, we went back to Michelle’s room, and put our boy clothes back on. We looked at each other with our nipples showing through our thin T-shirts, wearing make up, and our hair all girly, and laughed. Michelle went into her top drawer and pulled out two older model sexy Victoria’s Secret bras. One pink, and one white. She handed me the pink one, and then took off her shirt and put on the white one. Her boobs were spilling over the top.
Michelle explained, “These are Brittany’s favorite Bra’s. I steal them occasionally, just to annoy her.”
I took off my shirt, and put the pink one on, which squeezed my tits together creating awesome cleavage. We put our shirts back on, and I peeked at myself in the mirror. I loved how the bra changed the shape of the falsies under my shirt. And loved the way it felt. Not as sexy as the caress from the corset, but still nice.
We decided to go tell her mom what happened with the remover. In the hall we bumped into Brittany coming home from her job. She giggled when she saw us.
“What are you two faggots up to?”
“Keep laughing bitch. We’re wearing your underwear,” Michelle snapped back as she dug her thumb into her pants to reveal her panties and lifted up her shirt and flashed Brittany her bra.
Brittany lost her shit.
Michelle’s mom rounded the corner. Brittany pointed at us.
“This shit has to stop. Now he has his idiot friends dressing up in my clothes!”
“I know, I know, I’ve already talked to him,” Her mom deflected.
“Then why are their dicks still bouncing around in my undies?”
“Michael, I told you to take it all off.”
“We tried, but I’m out of adhesive remover, so we’re stuck with tits until tomorrow, and it’d just be weird to be in boy mode all night with… these,” Michelle explained.
“Fine, but just be sure to wash everything when you’re done,” Her mom fretted, “Andy, I’m so, so sorry. Can you call your mother and ask her if you can spend the night?”
I nodded, and she turned and left. Brittany just glared at us icily, and then stomped off.
I went to Michelle’s room and called my mom, and told her I was staying the night. She suggested I stay the whole weekend. It wasn’t ever a problem for me to be out of the house for extended periods of time. I was adopted, and I always got the feeling my parents resented that I wasn’t more of a stereotypical manly son.
I hung up my cell, and caught my reflection in Michelle’s closet mirror. I was amazed that even in a T-shirt and jeans, I was pretty. I played with my fake titties through my shirt. As I stood there admiring myself, Michelle walked in casually, locked the door, and leaned against the wall arms crossed.
I giggled, “Yeah.”
“Good. Cuz, we’re gonna have some fun tonight.”
The glint in Michelle’s eye worried me.
CONTINUED IN PART 2.