Editor's note: this story contains scenes of incest or incest content.
*****
After all that's gone down this past year and all the mind-opening experiences I've had, I STILL never expected to be in a strip club pulling a train for a group of hot transwomen for my bachelor party. Less expected: my brother is running the show.
* * * *
Let's back up. A lot has happened since our lives got mixed up with Kelly and Michelle, the beautiful young lesbian couple who move din down the hall from my gay brother Mark and I.
I say "gay brother" as if that needs distinction because obviously this is a straight world and I'm just your average straight guy, right? I could have gotten away with that a year ago before meeting Kelly and getting a taste for her strap-on in my ass. And before I'd tasted my first real cock or made out with another man and put my dick in a guy's ass. My mind had definitely opened and I'd slid over on the Kinsey Scale to somewhere closer to bisexual.
Gemma and I had been dating for several months. She's trans and probably the most beautiful woman I've seen in person. She's Native American, tall, with long black hair and black eyes with a light brown glow to her skin. The fact that she has a cock makes our sex life more interesting but she's 100% woman to me.
After our insane first 24 hours together, things calmed down for Gemma and I. We went on dates like normal people. The sexual chemistry was still off the charts but sometimes we needed to just go home and sleep if we had work the next day. I was working for a tech startup in the city and Gemma was working in advertising at a small agency so both of us worked long hours.
Michelle had moved in with Gemma right after she ended things with Kelly and sometimes I was jealous, wishing I was living with her. Six months in, things were still going strong so I suggested we try living together and Gemma was game. I was a very happy man and I knew Michelle would make a fantastic roommate.
When Kelly and Michelle broke up, that was the end of their deal with my brother to get Michelle pregnant. I'm not sure why it never worked after three months of fairly frequent fucking but it's possible Mark's otherwise perfect genes did not include a high sperm count.
A few months after I moved in, Gemma came home to find a candlelit apartment. Michelle was waiting inside dressed in a sexy waitress outfit with a very short black shirt, fishnet stockings, white collared shirt unbuttoned to reveal cleavage, and a choker.
"Welcome home, madame. Let me take your bag and coat."
Gemma was confused but delighted. "Okay, what's going—"
"Madame, follow me this way. Your dining companion awaits."
Gemma followed Michelle into the dining room to find me waiting for a dinner by candle light. "Are we doing date night here?"
I stood while Gemma took her seat, Michelle pushing in the chair for her. "I figured this would be a nice intimate night at home."
Gemma leaned over the table and kissed me.
Michelle moved to the head of the table and removed the white wine from the ice bucket. She poured Gemma a full glass and then filled mine as well. She bowed slightly and went into the kitchen.
"How did you get her to play Hot Waitress?!?" Gemma was stunned by Michelle's look and her performance.
"Oh she was totally into it. Especially when I told her why..."
I slipped out of my chair and got down on one knee.
"No. No fucking way, stop, oh my god stop." Gemma covered her face with her hands. I knew by the tone in her voice that she didn't want me to stop. I pulled a ring out of my pocket and held it in front of me.
"Gemma, my life has never been the same since I met you. You are everything I've ever wanted in a woman and you have a combination of compassion and strength that always amazes me. I have never been this happy and I don't want it to stop. Will you marry me?"
Gemma had tears streaming down her cheeks by this point and still had her hands partially covering her face. Her breathing was quick and she drew a long slow breath in to calm herself.
"Yes. Fuck yes."
I jumped up and hugged her, pulling her up out of her chair. She pulled away.
"Hey!"
"What?"
"Gimme the damn ring! It's not official until I've got that on."
"Oh crap, right." I kneeled down again and presented the ring. She put out her left hand and I slid it onto her ring finger.
"That's the way to do it!" Michelle was standing at the door with her cellphone recording the moment. "Congrats you guys, I'm so happy for you!"
Michelle joined us in a hug, squeezing us tightly, face mashed between our shoulders. She stepped back.
"Sorry. Ummm, sir and madame, your first course will be ready soon."
Michelle resumed her role play and left for the kitchen. We took our seats and raised our wine glasses.
Gemma toasted, "To a beautiful future."
"To a beautiful future indeed."
We sipped our wine like the adults we were quickly becoming. Then Gemma freaked out.
"Holy shit holy shit! I have to call Heidi! And my mom! And—" She started to get her phone but I grabbed her hand.
"There's plenty of time. Michelle spent all day slaving in the kitchen for us." I smiled and Gemma melted, smiling back.
She leaned forward and kissed me again. "You're right. Wow, I'm just so excited. I love you so much, baby."
"I love you, too. But I guess you figured that out."
"So do you have any regrets? I mean, we're pretty young." Gemma's voice went to a whisper. "You'll be sucking this one cock for the rest of your life..."
I laughed. Gemma knew that I still thought of myself as straight but she liked to poke fun at me almost as much as she liked to poke me.
"But it's the best cock around."
"I'll say," said Michelle as she entered the room with a pair of goat cheese salads. Michelle winked at me as she set them down. She refreshed our wine glasses and went back to the kitchen.
Gemma and I looked at each other in shock and then bust up laughing.
"Wow, I didn't expect that from Michelle!"
Gemma took another sip of her wine. "Michelle is always full of surprises. And you can't dodge my question."
I took a long sip of wine and thought.
"Honestly I'm not sure what I'd be missing. I didn't know what I was missing before I met you but there's no one I'd rather be with."
"Good answer."
"It's true."
"But you don't have a list of fantasies? I feel like everyone I know has a few itches they need to scratch... threesomes, Black guys, whips, anal, Asian girls, gangbangs, whatever."
"Hmmmm I guess I've done a couple of those. I had an Asian girlfriend in high school and I think that weekend we met had at least one threesome, right? I found out I'm not into pain with Kelly and I've never had a thing for Black guys. I've never been with a Black girl but I think I'll be fine."
Gemma nodded, amused. "So I guess that just leaves gangbangs..."
We both laughed and had more wine. "Yep, just the gangbangs. How about you?"
"Me, what?"
"Regrets? Unfinished business?"
Now it was Gemma's turn to pause and think. "I dunno... I did a lot of crazy shit in college. There weren't a lot of trans girls and I was pretty popular with the adventures types."
"So your checklist is all checked off? You had all of the anal gangbangs with Black guys and Asian girls and their whips that you could handle?"
"Yeah, pretty much. That was a crazy night."
"Wow." I smiled, not sure whether to take that as a joke.
Gemma said, "Look, it wasn't THAT wild but at times it got close. But if I can think of anything, I'll let you know."
We finished our salads and Michelle came out with the main course: steak, Gemma's favorite. It was perfectly broiled, medium rare and lightly seasoned. Michelle served my steak first and then put down Michelle's.
"Your meat, madame."
Gemma looked up at Michelle. "Is that some sauce to go with my meat, miss?"
"Oh no, ma'am. I wasn't being saucy." Michelle turned to go back into the kitchen and Gemma swatted her tight ass as she went.
I eyed Gemma carefully.
"Are you sure there's not someone—er, something you'd like to do before getting hitched?"
* * * *
The wedding was coming up soon. We'd opted for a small ceremony with just family and closest friends and our jobs afforded us a planner to take care of most of it. The bachelor and bachelorette parties were up to us, though.
My brother Mark took over planning my bachelor party and Michelle and Heidi were in charge of the bachelorette. We didn't have much time left and only one weekend worked so both parties ended up being on the same night.
Alejandro moved in with Mark after I moved out. He was couch surfing before that and things were still going pretty well with them but I knew they both fucked other people once in a while. Young gay guys are no strangers to open relationships but I was hoping they would get serious at some point; I really liked Alejandro and wanted him in the family.
So the guest list for the bachelor party was me, Mark, Alejandro, and a few guys from work plus a couple of college friends. We went to a raucous Mexican bar in the Mission with mariachis and everything and then, full of margaritas, we started a bar crawl through Hayes Valley and into Polk Gulch at the edge of the Tenderloin.