Big Help from Lil Sis Pt. 02

I had just gone into the kitchen to get a water when the doorbell rang. I am pretty sure I jumped and Kelly yelled down from upstairs for me to answer it. I loved hearing my heels on the hardwood floor of the foyer as walked to the door and opened it.

"Wholly Fuck! I mean... well wholly fuck." Stacie said greeting me.

"You look amazing Adam.... Ops sorry... Addie...." Jessie said.

Jessie stepped in and hugged me. Stacie continued to stand there staring at me and then finally entered the house. They each were already dressed. Jessie had on a purple fit and flair dress and black pumps like me. Stacie was a wearing a pink baby doll dress with a really short hem on it. She had on a pair of strapped sandals with a about a three-inch heel.

"I honestly don't know what I was expecting but... Jesus... you are fucking girl... a beautiful girl." Stacie continued to stare at me.

"Uh... thank you. You look beautiful also. I love your dress." Thank you.

Kelly had come down stairs and greeted both the girls and told them they could put their bags in her room. They returned along with Lisa a few minutes later. We spent a few minutes complimenting each other on our outfits. Stacie continued to look at me in amazement.

"Jessie... are Ryan and his friends still bringing the alcohol?" Lisa asked.

"Yes... they should be here in about thirty minutes. I think they have beer, White Claws, and tequila." She responded.

"White Claw and tequila... easy to see what their plan is, isn't it." Stacie laughed.

"Not sure they need either of those to be successful with me." Kelly said.

"Wow... plan on slutting it up tonight?" Jessie asked with a smile.

"Maybe." Kelly blushed.

"What about you Addie... plan on slutting it up?" Stacie giggled.

"Maybe." I was trying to be funny by copying what Kelly had said.

"So besides being into girls clothes you are also into dick?" Jessie asked.

"He is... oops... sorry.... She is curious about it. Hasn't had a chance to decide if she actually likes it." My sister said almost defensively.

"Well if it is genetic she will like it or at least like a mouthful of it." Stacie laughed.

"Coming from the girl who wants her butt full of it." Kelly stuck her tongue out at Stacie.

"What are you curious about? Do you want to give a blow job or to be fucked in the ass?" Jessie asked me.

"I ah... well umm... yes." I stuttered.

"Well girl we are going to have to see if we can't make that happen for you." Lisa said.

"Jessie, how many of Ryan's friends are coming tonight?" Stacie asked.

"Hopefully all of them with the help of you whores." Jessie laughed at her play on words. "And Addie if you don't get some dick while wearing that outfit something is wrong in the world."

"Funny... seriously... how many friends is he bringing?" Lisa asked.

"Three or four... I think..." She responded.

I did the math quickly in my head. If Jessie's boyfriend brought four friends that would mean there was a one guy for each girl if you included me. I am not sure if I was nervous about that or excited. I had fantasized and dreamed a lot about being with a guy.

In fact, when I jerked off, my go to was thinking about giving a blow job while doing it. I spent more than a little bit of time looking at dick pics on my phone. That was fantasy though, reality was very different and very scary to think about.

"Those numbers work pretty well don't they girls." Kelly laughed.

They all looked at me and I felt my checks warm up. My nerves were definitely on edge and I could feel my heart beating hard in my chest. I was excited about the possibility of being able to live out a fantasy while at the same time scared to death of it. I also had a serious concern and worry so I gathered my courage, took a deep breath, and blurted it all out.

"Let's just say that one of them is interested in me and I am interested in him. Do I tell them I am actually a guy and hope they don't care? Do I try to hide it? How does that even work? If he touches my boobs, he will figure it out right?"

They all smiled and laughed but I continued.

"I mean... have any of you ever had sex without having a guy touch your boobs? And obviously he is in for a big surprise but will definitely feel my... you know... my thing if he puts his hands between my legs. And you can laugh but I am serious."

"Okay... sorry for laughing... So... obviously the safest thing is to do what you said.... tell him before things get to far." Kelly said.

"But... if you don't want to do that... you can make an excuse... tell him it your time of the month and that your boobs are sore and it messy down there, but you are willing to blow him." Jessie added.

"Yea... you can keep all your clothes on and still do that. That is the easiest way to not be discovered." Kelly told me.

"Okay... that makes sense... not saying I am definitely going to do anything just nice to know if I was going to, how it might work out." I told all of them.

Kelly told everyone that she was going to go ahead and order the pizza. It was just past six o'clock now so it would be close to seven when it would be delivered. There was a nervous energy starting to be felt as we waited for Jessie's boyfriend and the rest of the guys to show up. All the girls moved about, and I found myself alone with Stacie for a minute.

"Uh... can I ask a question? I was told you would be a good person to ask this." I said to her.

"Sure... betting this about anal sex, isn't it?" Stacie winked.

"Mm... yes. Is that okay?"

"Sure... although don't believe everything these whores have told you. Yes, I like it, but no I am not constantly getting fucked in the butt." She laughed.

"Okay... are there any tips or tricks, or I don't know.... Things I should know, I guess."

"Yes... the first tip is lube... lots of it. Don't believe what you see or read in porn. Spit or salvia isn't going to be enough. When you think you have enough lube add more." She giggled a little.

"Okay." I nodded.

"Next... relax. The more you tense up, the more difficult it is going to be for him to get it in you, more importantly the more uncomfortable it is going to be."

"Oh... that makes sense." I replied.

"Finally, tell him to take it slow, at least at the start. Let yourself get used to it being there before he starts to really fuck you. Finally... let yourself enjoy the idea of it. You are doing something most people think is taboo and kinky and dirty... it is okay to get really turned on by that idea." Stacie finished.

"Thanks. That was all great advice. Um... what is the best... ah... like... position to be in?"

"Well... for me... I really like it when I am bent over something... like the bed, or the end of the couch kind of a submission thing or a being taken thing, but you have to be sure that the guy isn't going to be rough. Doggie style is good also for being able to have them get good penetration." She explained.

"I really appreciate you sharing all that with me." I said sincerely.

"I really hope you get to live out your fantasy." She said before walking off.

"Getting some coaching from Stacie, Sis?" Kelly said from behind me.

I jumped from some reason as I heard he speak. I wasn't sure why I was scared but that feeling quickly moved to happiness as my brain registered that she had just called me sis.

"We should probably go with cousin or something instead of sis though... If the guys think you are my sister, they are going to wonder why your room isn't more girly. That is if you bring a guy back to your room." She winked at me.

"Hey... that is true and thanks for reminding my room isn't girly." I faked a pout. "Umm... so Stacie gave me some advice about... well you know... do you have advice about uh..."

"Sucking dick?" Kelly cut in.

I nodded.

"Sure... the biggest thing I can tell you is... enthusiasm. If he thinks there is nothing in the world you would rather be doing right that minute than having his cock in your mouth, he will enjoy it. Lots of tongue action and your hand helping are good things also. Oh, and eye contact. Guys love it when you look them in the eye while their dick is in your mouth." She told me.

Right then the doorbell rang, and I jumped again. I took some deep breaths as Kelly went to answer it. I stepped out into the family room and noticed all her friends were watching me and had grins on their face. I saw Jessie also move toward the door as my sister opened it. I wondered how many guys would be on the other side.