It was a few days later when Josephine called me over to her house. We spent the entire night our first night together fucking until we literally couldn’t go another second. It was probably the most magical night of my life, and I couldn’t wait to see if tonight would be even better.
Josephine had me shave before I came over, and she had a change of clothes for me when I got to her place. It was a super cute black dress that would be easy to push up for fucking. She also had me put on red lingerie this time to contrast against the black fabric of the dress, and I felt so cute once I was wearing it.
She did my makeup and put some jewelry on me, even making me slip on a pair of black kitten heels. She told me that she would teach me to wear pumps and stilettos eventually, but she didn’t want me falling on my ass and hurting myself.
“I thought we could do something a little different tonight,” said Josephine.
“Different how?”
Josephine giggled and skipped out of the room, returning with a strap-on dildo dangling from her hands. My eyes widened, and I swallowed my breath as I took in the sight of that thing. It probably wasn’t as long as my cock, but it was thick. Far too thick for my virgin bottom.
“Don’t worry! I’m not trying to fuck you. Not tonight at least,” Josephine said and cackled.
“What do you mean?”
“I set up a dating profile for us! There’s one super hot guy who is interested, but he wants to see a picture of your cock first.”
“What the fuck? What are you talking about, Josephine?”
Josephine laughed. I didn’t know what she thought we were about to do, but anything with a guy was probably a step too far for me. I just wanted her to ride my dick and let me fuck her like she did the last time we were together.
“Lighten up, boy!”
“Why did you set up a dating profile for us? And what do you mean that there is a guy who’s interested? I’m not gay.”
“Don’t you want to fuck some ass? Won’t you even consider it?”
I crossed my arms over my chest and shook my head. Josephine ran over to me and plopped down next to me on the couch where I was sitting.
“Oh, come on! He wants to play with both of us. He thinks you look super sexy as a girl, and I have to agree.”
“Yeah, but why can’t we just fool around?”
“I mean, we can, but I thought you might want to let someone else be on the receiving end. Unless you want to take my big cock?”
I took one look at the strap-on dildo and realized that Josephine had me backed into a corner. I had never really thought about fooling around with a guy, but maybe it wouldn’t be so bad if Josephine was there.
“What if I can’t get hard?”
“I’ll make sure you get hard. I’ll actually do that right now to get a picture of your dick... if you’re willing.”
I glanced down at my crotch, trying to picture myself fucking some dude, and maybe I could do it… with Josephine by my side.
“So, this guy wants us both to fuck him?”
“Yeah, he’s been sending me pictures of his asshole. Want to see?”
“Uh… sure?”
Josephine giggled and unlocked her phone. She went to the app she was using and turned the screen toward me to show me pictures of the guy’s asshole, and I was weirdly… turned on. The guy was big, but if he wanted to get fucked, maybe it would be hot, especially if Josephine was plowing the guy too.
“It’s hot, isn’t it?”
“I don’t know,” I said. “I guess.”
“Tell me you wouldn’t fuck that!”
“I would if you were there with me.”
Josephine grinned and wrapped her hand along the side of my face as she leaned in close to give me a kiss. “That’s all I wanted to hear. Now, how about I make you hard, so this guy can see how big your girly dick is?”
“Uh… yeah, okay.”
Josephine smirked as she fell to her knees between my legs. She lifted my black dress and moved my red thong to the side, and my cock was already half hard when she wiggled it out of the thong, and it got increasingly hard when she wrapped her warm, wet lips around it.
It didn’t take long before I was fully erect, shaking a little from the pleasure coursing through my body. Josephine pulled her lips off my cock and giggled as she reached for her phone to take a picture of my feminized cock, and fuck, I was kind of turned on by the sight of it. If this guy wanted my cock, who was I to judge?
“Sent,” Josephine said a moment later. “Fingers crossed he agrees.”
“Yeah, fingers crossed,” I echoed.
***
The guy agreed, and my heart was racing when I heard his footsteps coming down the hallway. Josephine looked absolutely giddy. She had a sheet on the living-room floor, a big bottle of silicone lubricant, and her strap-on dildo. She ran over to the door when our guest knocked.
“Ralph, I’m so glad you made it!” Josephine said when she opened the door. “I’m Josephine, and this is my femboy Gerald. Isn’t he adorable?”
“Yeah,” Ralph said in a scruffy voice as he stared right into my eyes. He was much bigger than I would have expected, and I certainly wouldn’t have pegged the guy as someone who wanted to get plowed by two dicks. He was the type of guy everyone would assume was an alpha. Tall, deep voice, strapping muscles. He looked like he should be a sergeant in the military.
I waved.
He waved back.
He stripped off his clothes a second later. He had a cock ring around his already half-erect cock, and then he took Josephine and pulled her into his arms to kiss her. She moaned into his mouth, opening her eyes for the briefest of seconds to look at me, and I knew then that I had to join them.
The train had left the station, and I was onboard. I walked over to them, and Ralph pulled me close to his rugged body. He was so firm and muscular, and I felt a weird sense of arousal as he touched my body, but Josephine’s hands were on me too.
We kissed and touched like that for a few minutes until Ralph pushed me over toward the sheet on the floor. He pushed on my shoulders until I dropped to the ground, and then he dropped to his knees in front of me. He spread my legs with a forceful hand and lifted my dress, revealing the tiny red thong that was covering my cock.
My hard cock.
I didn’t know why I was hard from a man, but I was. I could no longer deny it, but Ralph’s rough touch got me excited, and his mouth felt warm and soft and wet when he wrapped his lips around my feminized dick. He had no problems swallowing my entire shaft, pushing it deep into his throat.
I gasped, but then Josephine stepped in front of me and lifted her dress. Then she grabbed the back of my head and shoved my face into her pussy. She was so hot and wet on my face, and all I could do was slide my tongue across the folds of her pussy while Ralph bobbed his head along my dick.
It was all too much to handle!
Ralph seemed to notice this and pulled off my dick. He was already naked and ready. He grabbed the bottle of lube and put some on his fingers before rubbing the clear liquid against his hole, getting to his hands and knees.
“Put on the strap and fuck me,” he commanded Josephine.
She held my face against her womanhood for a second longer before releasing me. I sucked in a sharp breath as she reached to grab the strap-on dildo, pulling it up her legs and fastening it into place. She dropped to her knees behind Ralph and grabbed the bottle of lube to lather her dick.
“Come over here and let me suck your dick, femboy! Just one warning, though. You’d better not cum before I get to feel that big girly dick fucking me.”
I nodded as I stared into Ralph’s powerful eyes, and then I crawled over to him and sat in front of him with my dick hanging out of the red thong. He smirked at me before reaching out to wrap his hands around my base, and then he took my cock into that warm mouth of his, showering me with pleasure.
He grunted on my girly cock when Josephine pushed into him from behind. She winked at me as she filled his hole with her dick, and then she grabbed his hips and started pounding him hard. Ralph tightened his lips around my cock as Josephine fucked him, making me gasp and moan. I pushed him off my dick before I came, which made him smile.
“Good, boy. You know how to listen.”
I didn’t know what to say or how to respond, so I just sat there catching my breath, still on edge, like I could cum at any second.
Ralph dropped his head and moaned deeply as Josephine fucked him a little harder. She was really working his ass, and the smile on her face while she did it was priceless. Her tits bounced and swayed as she fucked Ralph, but then he moved forward, making her cock fall out of him.
“Hey!” Josephine protested. “What gives?”
“I want you guys to DP me,” Ralph said. “You on bottom, femboy.”
I nodded and got to my back. I didn’t know how my life had led me to this point, but I was not upset about it. Ralph straddled my hips and winked at me before bearing down on my cock, filling himself with my shaft, and fuck. It felt so good. I didn’t even care that Ralph was a man. He wanted my dick so badly, and I wanted to give it to him.
“Now you, Josephine!”
Josephine giggled as she got behind Ralph. I couldn’t believe he was taking it when she started to push her fat cock into his already stuffed hole, but he was doing it! He grabbed my fake tits as Josephine pushed deeper and deeper into him, and the friction of her cock against mine was otherworldly.
“Yes!” Ralph said in a deep voice. “Fuck me, girl!”
Josephine thrusted her hips, and that about did me in. I screamed out as her cock kept rubbing up against mine, basically jacking it off while it was surrounded by the warmth and tightness of Ralph’s hole. I wanted to last, but I couldn’t. It felt too good.
“I’m sorry,” I said in a breath before screaming out. I was trying so hard to hold my load, but it was impossible. “Fuck!”
“Yeah, femboy! Fill my hole!”
Thick streams of cum left my dick and filled Ralph’s stuffed hole, but the cum made for an amazing lubricant. Ralph moaned as Josephine moved her hips a little more easily, not at all bothered by the fact that I was being tormented by the intense pleasure.
They ignored my screams and moans, working me to a second orgasm shortly after the first. When I came that second time, the other two came with me. Ralph hollered out and gripped my shoulders just as his cum shot all over my abs, and then Josephine was cumming behind him. She had her hand in the strap, rubbing her clit, until she was screaming.
I’d never felt greater relief than when our bodies separated. I gasped and rolled over, laughing like a fool. I’d never cum twice like that in my life, and I was floating on cloud nine. The other two were as well. It was at least five minutes before we finally got up and started to clean ourselves.
“Glad I came over. You two did not disappoint,” Ralph said as he dried himself off with a towel.
“Neither did you,” Josephine said.
I nodded my head in agreement. We hung out with Ralph for like half an hour before he said he had to leave. Josephine and I cuddled on the couch and watched a movie after he left until our eyes couldn’t stay open. I held her all night and didn’t want to let go when we woke up in the morning.
***
One Month Later
“Do you want me to pick up anything before I come over?” I asked Josephine as I sat in my apartment. I was already dressed in a skirt and heels, no longer worried about going out in public dressed as a girl. I had on a wig and jewelry too. The only people who really paid me any attention when I was all dolled up were horny guys.
Not that I paid them any attention.
My heart belonged to Josephine.
“Would you get a joint from the dispensary? I want to smoke before we go out to eat.”
“Yeah, sure. Anything else?”
“Only your pretty face!”
“Be there in like forty-five minutes.”
“See you then,” Josephine said and hung up the phone.
I had the picture she’d taken as us saved as her contact image on my phone and spent a moment staring at it, rubbing my thumb over her pretty face. Josephine had really opened my eyes ever since we met, and I couldn’t wait to see where the future would take us. Josephine knew I wasn’t like other guys, but that was what she liked about me.
I grabbed my purse and headed out the door, my heels clicking against the floor as I went. I spun in a circle as I walked down the hallway to the staircase, happier and more comfortable with my life than I’d ever been.
THE END