Catfishing Sis with My Girlfriend

My name is Danny, I was 24 at the time, and in a long term relationship with my girlfriend Shannon. Shannon was 30, and is just an all around beautiful person. She is 5'10, with dark brown hair, tan skin and a fit physique. As far as her body goes, she has small, perky tits, and a really firm ass. We both really loved each other, but as far as our sex life went, we are were vanilla. This is what disappointed me most about our relationship, because I had a kink that I was too afraid to bring up. This was crossdressing. I shared an apartment with my 26 year old sister Julia, and whenever she left, I had the habit of dressing up in her clothes and taking pictures of myself in sexy poses, and would jerk off while wearing them. I always wanted to tell my girlfriend about this, but I was too afraid my girlfriend would think it was weird and dump me. Luckily, I never had to actually tell her.

One day, when Shannon and I were hanging out, I went to the bathroom and when I cam back she had my phone in her hand. I ran over to take the phone from her, and when I got it, I saw all of my crossdressing photos.

She asked fairly calmly, "Danny, what are these?"

I fell silent.

"I'm not mad baby, just tell me what these are."

I gathered myself and said nervously "W-w-when Julia is gone, I sometimes like to dress up in her clothes. Please don't tell her, she'll kill me if she finds out."

"Don't worry, I won't say anything if you do something for me."

Later that day, we spent our time making a snapchat account under the name Sydney Moyer, and pretend that I am a girl to anyone who adds me. I initially thought that this wouldn't be that hard, until later that night. My sister had come home from work that day, and we all sat down for a dinner prepared by Shannon.

Not long after we started eating, Shannon says to Julia "I know you've been looking for a partner recently. I was wondering if you would want me to give your a friends snap?"

"Sure, what's their name?"

"Her name is Sydney Moyer."

As she says this, I dart my head towards Shannon, and she just smiles back at me.

Julia responds "Thank you Shannon! I'll probably talk to them tonight!"

Shannon nods her head, and we continue eating dinner. During this time, my mind is racing all around, wondering if I should tell Julia it's a joke, and Sydney is me, or just flat out not respond. I mostly sure that I wasn't going to play along, but then I thought about what would happen to my relationship with Shannon if I didn't. Would she break up with me for having disobeyed her? I thought about this all night. Eventually Shannon went back to her apartment for the night, and my sister and I started watching TV. Then I suddenly get a snapchat notification on my phone.

Julia says "Weird, you got that right as I sent a snap."

I look down to see that the message I got was from Julia. At this moment, I decided to obey Shannon and pretend to be Sydney. I quickly shifted positions on the couch so she couldn't see my phone. We exchanged greetings, and we both chatted about ourselves, or in my case who I was pretending to be. I had to come up with a lot of random details on the spot, but I thought everything I said was convincing. Eventually, she texted good night, and at that moment, Julia got up and said she was going to bed. I soon followed, but was barely able to fall asleep, because I kept thinking about how wrong it was lying to my sister like this.

The next day, Shannon calls me over to her apartment. When I get there, she asks for my phone, and checks to see if I talked with Julia. After confirming that, she calls Julia. She tells her that she wants me to stay at her apartment for a while because there has recently been a lot of crime nearby. Julia tells Shannon she doesn't care what I do as long as I still pay rent. Shannon thanks her, hangs up and tells me our plan for the day. She's going to take me shopping for a wig, women's clothes and makeup, so I don't have to steal anymore to crossdress. She also tells me the real reason I'm staying at her apartment.

She wants me to, so that I can dress up without Julia finding out and send her pictures of me crossdressing. I started to say I wouldn't do this, but stopped after wondering what would happen to our relationship if I didn't. In the following week, I practically lived as a girl, always dressing as one, and going in public as one. Shannon helped teach me how to do my makeup, and helped train my voice to sound more like a girls. Over this time, Julia and I constantly texted, and even send pictures of ourselves to each other. She wasn't able to recognize me, because I looked like a completely different person. Eventually, as our conversations grew more deep and meaningful, Julia brought up the idea of meeting in person and I reluctantly agreed.

We had met up at bowling alley, and started our date. I wore a cute flowered blouse to the date, and despite me insisting to Shannon that it didn't matter, she made me wear some skimpy panties and a sexy lace bra. When I saw Julia, I was amazed by her beauty. She wore a tiny crop-top that accentuated he huge boobs, a short black skirt, and fishnets underneath that pressed up against her thick thighs. Seeing her like this, she barely seemed like my sister. This helped me enjoy the date a lot more. We had a lot of fun bowling, and afterwards went to a nice restaurant. By the end of the night, she asked me to walk home with her, so I did. When we got up to our apartment, I said goodbye, but she pulled me in for a kiss, she forced her tongue into my mouth, preventing me from saying anything as she dragged me to her room. She threw me on the bend, and started stripping me.

Before she could, I screamed "Wait! I need to tell you something!"

She kept stripping me and said "I already know you're not really a girl. Shannon told me before I started texting you."

That was the least of my worries at the time, what I really wanted to say was that I was her brother. Before I could get anything out of my mouth, Julia got into my panties and wrapped her lips around my penis. She started moving slowly back and forth to get me hard, but once I was erect she went crazy. She started rapidly sucking, taking my penis all the way to the base as her throat made choking sounds. I told her when I was about to cum, and she took me penis deep in her throat and let me cum. I looked at her face as she swallowed my cum. Her makeup was running from all the saliva she made fly around, and I could tell by her eyes that she wanted me in her. At this point, I stopped caring that she was my sister, and just knew I had to fuck her. I flipped her onto the bed and thrust straight into her without moaning. I fucked her as hard as I could, which just made Julia scream in pleasure. She was so tight that every time I pulled outward, her pussy would just suck me back in.

I started pulling out of her pussy and said "I'm about to cum!", but she wrapped her arms and legs around me and pulled me to her.

"I'm on the pill, cum inside me!" Julia put her lips on mine, and we started tongue fucking each other as I released my load inside her.

We made out for another 10 minutes, and fell asleep in each other's arms. The next day, I woke up and couldn't find her anywhere in the apartment I thought it was weird, but just kind of brushed it off and went home. I went to Shannon's apartment and immediately told her how much fun I had fucking my sister.

"I already know. Julia told me. She also found out you were her brother. When she woke up, she noticed you get a notification on your phone and recognized the background, she decided to look at the notification and saw it was from your friend."

"So she knows? What will I do! She'll never forgive me!"

"Don't worry, she'll come around."

There were about three weeks where neither of us heard from Julia, until she texted both of us to meet at her apartment and for me to crossdress. When we got there, Julia led us to the couch, and sat down across from.

She sat staring at us in silence before saying "I don't know what to do. I enjoyed the time I spent with you as Sydney, but now that I know you're my brother it's hard for me to live with what I did. But beyond this, I'm more curious why you set this up Shannon."

Shannon responds "Ever since I met you after dating Danny, I've been in love with you and him. I thought if I asked for us all to be together, I could convince Danny but not you. So, I made Sydney because I know you are lesbian, but I thought you might go for a crossdresser, and you did. Once I got you two together, I thought it would be easier to convince you for us to all be together."

"Let's say we were all together, how would that work?"

"We would all move in together, and Danny would become Sydney at all times, and whenever we have sex, we do it together."

There was a long pause. I sat there not knowing what to say until Julia blurted out "Fine, I'll try it."

"Good!" Shannon said "I'll start moving in tomorrow." She stood, and pulled me up and out the door. Shannon and I went the whole way home, and went to be without saying a word. The next day, she had us start packing things, which wasn't much so we headed over to Julia's. We got there around dinner time, and Julia had made something for all of us. We sat and ate in silence. When we were all finished, Shannon said we were all going in Julia's room. When in there, she ordered Julia to start sucking me off. Reluctant, now knowing that I am her brother, she slowly undresses me, and sucks me off until I cum. During this, Shannon is masturbating while watching us. This relationship continues into present time.

As we continued having sex, both me and Julia got more comfortable and started having sex like normal. As this went on, we settled into a routine. Usually, I would roughly fuck Julia until both of us cum as Shannon watches and masturbates. Then Shannon will put on a strap-on and fuck both me and Julia in the ass. When she first got the strap-on, neither of us had done anal, so we both lost our virginities together. Some might think the threesome, incestuous, crossdressing relationship is weird, but we are all the happiest we've ever been. I'm especially happy, because I now crossdress whether at home or in public, and I have two beautiful women who support me in doing so.