Twinsies Pt. 01 - First Night Out

Sarah was still sucking on my hard dick but I was much more focused on the tongue in my ass and the girl dick inserted into my mouth. June pulled her tongue from my ass which caused me to slightly whimper around the phallus in my mouth. June grabbed my cheeks and squeezed them again before moving one hand to squeeze more lube out of the bottle. She began to rub it onto something with even more wet squelching before something cold and hard came into contact with my anus. One of her hands was on my hips and the other was holding the tip of what I guessed now was a strap on dildo. Based on the tip I gathered that it was a bit wider than the one currently inside my wet mouth.

June very gently pressed the tip against my anus but it gave a lot of resistance, "Relax your muscles, Clark. Or would you prefer Clara with how things are tonight? If you relax it won't hurt nearly as bad."

I tried to take her advice and relaxed my body then I felt my ass loosen slightly. She also noticed and tried to push again. This time my sphincter relented and let the tip of her rubber cock penetrate. It stung a lot but surprisingly felt good at the same time even though it was just the tip. She placed her other hand onto my other hip and began to slowly push more. The rubber dick began to stretch my asshole around its thick, realistic, veiny surface as it slid deeper and deeper into me.

June thrusted the rest of the fake dick into me which elicited a grunt from me once she bottomed it out within my no longer virgin asshole. She stayed in place, balls deep inside me, letting my newly stretched butt get used to the foreign feeling of being filled. I could feel my ass tighten around the entire thing but it oddly felt really good within my sexualized bowel. Once my ass began to adjust to the width of the fake phallus lodged within me the pain and discomfort subsided and became a pleasure full experience.

"Are you ok, Clara?" June asked sweetly as she rubbed my back and hips with her soft hands. I mumbled an 'mhmm' around Amber's cock. Amber lightly brushed her fingers through my (wig's) hair still which I could feel. This was actually quite comforting with all the newness of the situation.

"Do you want me to keep going, then?" June questioned. I gently nodded which moved the dick in my mouth a bit. I realized I kind of liked that sensation so I started to move my head up and down slowly. I had begun to enjoy having both of my ends filled. My oral motions had also started to elicit moans from Amber. I looked up towards her and as soon as our eyes met her cock twitched in my mouth as I felt it slightly grow. Relishing in the fact that I was pleasuring her I decided to try and move farther down her shaft. I relaxed my throat almost the same way I had let my ass loosen and pushed down letting her cock slide deeper down my hot wet throat.

This made her moan as I started to actually suck on her as well. As I felt precum ooze out of her hard prick and down my throat I found myself enjoying the sensation. The gooey texture coating the back of my wallet throat felt sexy which was only intensified by knowing it was a girl I was pleasuring to make the fluid come out. But that wasn't enough. I now wanted to feel her actually cum and shoot into my mouth.

I doubled my efforts a bit with my sucking and brought one of my hands up to her shaft. Slowly moving it up and down I stroked her and the same pace as my bobbing. She moaned more and seemed to be breathing a little shakily. June hasted her thrusting as well once she noticed me really getting into it. Sarah was moaning and humming as well causing a vibrating sensation to go through my dick. It felt amazing and I never really wanted it to end but I could feel myself getting close to climax. I felt Amber begin to shake a bit and I knew what she was doing. She surprisingly grabbed the back off my head and pushed me down onto her all the way as the first strand shot out and splattered against my throat.

I clamped my lips down and swallowed as much as I could as more streams came spurting out of her tip. The feeling of her cumming in my mouth made me go over the edge and start to cum. I began flooding Sarah's mouth with my own shots of jizz as she tightened her lips around me.

A strange sensation had been also building in my ass. Once June had noticed I was cumming she grabbed onto my hips tightly and thrust the dildo deep into me a couple times and a sudden burst of pleasure shot through me at lightning speed. I tensed up and my ass clenched hard around the rod in my ass. One of June's hands had left my hip and I felt something start to squirt into my butt. It felt really sexy and I was loving it. As the fluid stopped shooting inside my body slowly relaxed.

"What was that, sis?" I asked my sister behind me.

"That is what it feels like to be cummed inside of. Did you like it?"

I nodded my head, "Mhm. All three of those were amazing. I don't know what I liked most." June pulled the dildo from my ass slowly. With a small pop it tip came out which brought an involuntary whimper to my lips.

She heard it and teased me by putting the head back up to my asshole and rubbed it around, "Looks like you really liked it, huh?"

"Yeah. It felt really good." I admitted

"Good. Now that you know what it feels like to be fucked you can probably get some from any guy you want at school."

"Really? You think I could get stuff like that?"

"Yeah. And better. Some guys have bigger or much sexier dicks and they are willing to put it in almost any wet hole willing to open up to them. Especially if you learn to do everything we do tonight on your own."

I thought to myself about what going to school all girly would be like. One of my first thoughts was about my friends. I realized though that they all at first thought I might be trans when we met since My figure was so feminine. Now I could come out and say I was and none of them would likely say anything. I started to get excited, "Sis? Could you teach me how to do makeup for myself?"

-To be continued.