Big Help from Lil Sis Pt. 03

Big Help from Lil Sis- Part 3

Last part of the three-part series. All characters are over eighteen years old.

Jessie moved towards the door as my sister opened it. The first guy through the door said a quick hi to my sister and then moved over to Jessie and wrapped an arm around her and gave her a quick kiss. He was obviously her boyfriend. He stepped out of the way and the boys with him streamed into the house. They were carrying cases of beer or White Claw and one had two brown bags in his hands which I assumed was the tequila.

I think I subconsciously counted as each one stepped into the house, and I wasn't sure if I was happy or if I became more nervous when I realized there was five of them. There was going to be a one-to-one ratio of boys to girls.

"Everyone this is my boyfriend, Ryan. I will let the rest of them introduce themselves and you all can do the same." Jessie announced.

They went one by one and then we did the same. I focused hard on my voice when it was my turn. I felt their eyes looking me over as I said my name was Addie and that I was Kelly's cousin. In fairness, they had looked at each of us as we introduced ourselves as if they were deciding would they want to have sex with us. I had also noticed the grins or maybe smirks from a couple of the girls as I said I was Kelly's cousin.

The beer was brought to the kitchen and put in fridge. Interestingly all the guys took a beer, and four out of the five girls choose White Claws with Stacie being the exception and opting for a beer. There was a tension in the room that was broken when the doorbell rang again.

Kelly and I went to answer it and found the pizza delivery boy standing on the porch. A smile spread over his face as he looked at us while we took the boxes from him. I slipped him a twenty-dollar bill that I had taken out of drawer in the kitchen for his tip.

We took the pizza boxes over to the dining room table and set them down. Some paper towels were brought out to be used as plates and everyone dug in. I watched as the boys inhaled their slices and the girls tried to do the exact opposite. I hadn't really had any direct interactions with any of them yet but was starting to feel my nervousness subside. That may had been because my first White Claw had gone down so fast.

Two of the pizza boxes were empty so I reached for them to take them over to the trash in the kitchen.

"I got them. Where do they need to go?" One of the guys asked me.

"Uh... over here in the kitchen." I moved in that direction as I struggled to remember his name.

"Matt." He blurted out. "I could tell you were trying to remember."

I laughed. "Thanks Matt... you were right, sorry. I am...."

"Addie.... Kelly's cousin. It is nice to meet you. Do you live near here?" He smiled at me.

I couldn't tell if it was a cocky smile, a humorous smile, or a flirty smile. What I could tell was he had an amazing smile of almost perfect white teeth. He also didn't just smile with his mouth. He had the ability to smile with his eyes also.

I liked that even in my heels he looked just a little down to meet my eyes. I guessed he must have been about six feet two inches tall. His brown hair was cut short and tight. He was wearing khaki shorts, and a polo shirt that was covering what appeared to be a fit body and waist.

"I uh... live in Springfield but go to school at State." I made up the first part and went with the truth for the second part.

"Oh great. What year are you?"

"Finishing my sophomore year. What about you?" I kept my eyes locked on him even though I wasn't sure exactly how I was breathing right then.

"I am finishing my sophomore year also... at Montgomery... I live in Fairview."

Interesting. Fairview was just over a hour from here and was two hours from where I went to college at.

We moved onto what our majors were. He was majoring in communications. He was going to college to fulfill a promise to his parents and grandparents that he would get a degree. What he really wanted to do was get a job as a fireman after he graduated.

"I will have to make sure to keep an eye out for the calendar after you become one." I interjected as he was telling me this.

He looked a little confused.

"You know the fireman calendar... the hot guys without their shirts on holding axes, or kittens or whatever." I said nervously.

"So, you think I am hot?" He winked.

"Umm..." I started to die of embarrassment.

"Just teasing you. But I am going to take that as a compliment coming from someone as beautiful as you." He blushed a little.

Kelly walked in carrying another empty pizza box with the guy that I think was named Steve following her carry a bunch of empty beer cans. They dumped them all in the garbage and he grabbed a bunch more out the fridge.

"Addie, can you grab some White Claws. We are going to go out back and play some flip cup before it gets dark." Kelly was getting a sleeve of red Solo cups out of the pantry.

I followed her direction and Matt offered to help. I was bent over getting them out of fridge and looked back over my shoulder and caught him staring at my ass. When I turned to hand them to him, he shrugged his shoulder to indicate he knew he had been caught and said sorry. I smiled at him and winked.

We met everyone out back I noticed that Lisa gave me an odd look as we took the drinks over to the table. Someone decided we would play boys against the girls. Jessie was at one end with her boyfriend across from her. I stepped in next to her and Matt jumped into the spot across from me. Kelly moved next to me and the guy who had come into the kitchen was across from her. I was beginning to see a pattern.

Normally I am pretty good at flip cup, but my nail kept catching the table or something and it was throwing me off. After the third round I figured that part out. Because the girls were getting beat, we needed more refills and I volunteered to go get them and Lisa offered to help.

"You didn't waste any time picking one out. Did you?" Lisa said as soon as we got inside.

"What do you mean?" I asked although I was pretty sure I knew.

"You grabbed onto Matt pretty quickly."

"He just offered to help me. Is there a problem? If I did something wrong, I am sorry." I told her.

"No... he just caught my eye when he walked in and before I could make my move, he was all over you. I am just being a bitch." Lisa laughed.

"Oh... I didn't know you were interested in him. We can switch spots when we go back out." I told her.

She smiled. "No... I told you I am just being a bitch."

We made it out back and distributed the cans to everyone so the game could start again. This round was more even, and the girls won about as often as the boys. When we ran low on alcohol we decided to stop. No one was drunk but everyone was feeling happy.

After pretty much the whole group took a pee break, we were all back in the family room. I had sat on the love seat and Matt had quickly taken the seat next to me. I was concentrating on keeping my legs closed and making sure I didn't flash anyone. Lisa and Kelly were sitting in the middle of the couch. Scott and Steve were on squeezed into next them on the outsides.

I looked over and saw that Stacie was sitting on the arm of the overstuffed recliner and Brian was sitting the chair. Jessie had pulled chairs in from the dining room for her and her boyfriend who was missing right now. I guess we had all coupled up already.

Ryan walked in holding one of the bottles of tequila and some mini solo cup shot glasses. He started handing out the cups and then moved to the center of the room.

"So we can all get to know each other a little better how about a game of Never Have I Ever? If you haven't done something you have to take a shot." Ryan announced.

You could tell by the boys faces they were all in on this idea and had probably planned it before coming here. I looked over at Kelly and she gave me a small shrug. Stacie was smiling so it looked like she was willing to play. Lisa's face showed that she was more than a little nervous about playing. Jessie pretty much didn't have choice since it was her boyfriend who had suggested it.

"Well... girls are you in?" Ryan asked.

"I am." Stacie quickly said.

"Okay... I will do one round and see from there. I am not a big tequila drinker and sometimes it makes me do stupid things." Kelly giggled.

"I like Kelly's plan and the same on tequila." I added smiling.

"One round and I reserve the right to withdraw before that." Lisa said after a slight hesitation.

"Awesome." Ryan announced and went around the room and poured each of us a shot.

When he sat down Jessie said. "Kelly since you are host you can go first."

"Oh... well... okay... I guess. Let's see." She hesitated then quicky said. "Never have I ever... performed oral sex."

I laughed inside because according to all her friends Kelly had probably given more blow jobs than anyone else here, and maybe more than all her friends combined. I also realized that I wouldn't have to drink because she didn't say blow job or sucked dick. I had performed oral sex it had just been on a girl.

Lisa sighed and brought the cup up to her mouth. I think I heard Stacie giggle a little as she did. What was surprising was when Scott who was sitting next to her did also. Matt and I gave each other a little grin when we didn't drink.

Ryan filled their cups and Steve went next. "Never have I ever swallowed after performing oral sex."

Lisa took another drink along with all the boys. I realized I would have to drink for this also but was worried what Matt would think when I did. Would it reduce his obvious interest me. I brought the shot up and took a drink. Maria, Kelly, and Jessie still hadn't had a drink.

After the cups were filled again it was decided that Lisa would go next. You could tell she was struggling with coming up with a question. Finally, she blurted out.

"Never have I ever had a threesome."

It looked like everyone was going to be taking a drink for this one. As everyone lifted their cup, we noticed that both Ryan and Stacie didn't. Ryan not drinking caused him to receive an interesting look from Jessie. When I looked over at Stacie, she gave me a quick wink. Matt and I also shared another quick smile.

Jessie went next. "Never have I ever hooked up with someone of the same sex."

You could feel a little tension in the room as everyone looked around to see who wasn't going to drink.

"Define hook up... like oral sex, hand jobs, what." Brian asked.

"Umm... how about never have I ever gotten off with a someone of the same sex." Jessie responded.

Kelly, Stacie, Ryan, Scott, and Steve all took drinks. I was playing a little with the truth on this one. Since right now I was girl and I had been with girls, I decided I didn't have to drink. Kelly had caught onto that also and gave me a quick wink. I was surprised that for the first time Lisa didn't have to drink, along with Jessie, Brian, and Matt. I was a little excited that Matt had at least had some experience with a guy a before.

Ryan went next. "Never has I ever masturbated to gay or lesbian porn... Gay for the guys and lesbian for the girls."

Scott asked. "Does tranny porn count?"

"Just for the guys." Ryan laughed.

Steve and Stacie were the only ones to drink. I looked at Matt and he a sheepish grin on his face and I gave him a big smile back and winked.

It was Stacie's turn. "Never had I ever had anal sex."

Lisa, Kelly, Steve, Brian, me, and Matt all took a drink.

Jessie turned really red as Ryan gave her a big smile. I wasn't sure but looking at their faces it seemed like it was something new that had happened between them. Brian looked up at Stacie with a raised eyebrow and she smiled and winked at him.

Brian jumped in as soon as the cups were refiled. "Never have I ever had a one-night stand."

Only Lisa and Scott drank. I think everyone in the room laughed when it happened since they had kind of paired off.

I was happy to not have to take a drink the last couple of rounds. I was tipsy but didn't want to get drunk. At some point Matt and I had moved closer and now our thighs were pressed against each other. It was our turn and we looked at each other to see who would go next.

We had hit most of the main stream taboos, oral, anal, same sex, threesomes, I was thinking when Matt said.

"Never have I ever either given or received a facial."

"Oh... good one." Stacie said.

Me, Lisa, Ryan, Jessie, and Matt all took drinks. Kelly and Maria looked a little embarrassed while Brian, Scott and Steve sat up and had an almost proud look on their faces. I looked over at Matt and felt my cheeks flush. I actually thought about whispering in his ear that he could give me one so next time we wouldn't have to drink.

I struggled to come up with a good question but finally said. "Never have I ever had sex in public."

I was surprised that only Lisa, Ryan, and Scott had to drink to that one.

We all decided that it was time for a bathroom break and as we came back people spread out a little and it was obvious the game was over. That was good since most of the good questions had been asked already and I wasn't really excited about drinking anymore tequila. I stepped into the kitchen and saw Lisa chatting with Matt and was surprised that I was instantly jealous.

Matt saw me and broke away from Lisa and moved over to my side. I immediately felt my mood change and my pulse go up. He asked me if I wanted another drink and I told him yes. He grabbed each of us one from the fridge. He handed one to me as we stepped back out into the family room and went back to the love seat.

I noticed that Ryan and Jessie were on the couch now and that Stacie and Brian had disappeared and I also didn't remember seeing Kelly and Steve when I was in the kitchen and they weren't in the family room either.

"Were you surprised by any of your cousin's responses to the game?" Matt asked me.

"No... not really? How about you. Were you surprised at any of your friends' responses?" I asked him.

"No... not really." He laughed that he repeated my answer.

We looked at each other for a minute and you could feel tension building. The silence was a little awkward.

"How about my answers. Any surprises?" I asked breaking eye contact as my nerves grew.

"Uh... hmm... not really... I guess."

"Uh.... hmm... I guess... sounds like maybe there is but you don't want to say it?" I looked right at him and winked.

"Well okay... can't believe I am asking this... the never swallowed? Not even once? You aren't curious about that?"

"Oh... I am curious about it. Just haven't had the right... I guess... opportunity." I said with some confidence.

He got a strange look on his face. I figured that was because I had said I had performed oral sex before so in his mind the opportunity had occurred. I had played pretty fast and loose with my answers. I had never lied but I hadn't totally been honest and used the ambiguity of presenting as a girl to my advantage.

"So... you have hooked up with a guy before? How was that?" I asked the question with enthusiasm and made it sound like it turned me on a little.

"Reality... I was just answering the question honestly. An old buddy of mine gave each other hand jobs one time. We started off watching some porn, then jerking off, and somehow ended up doing that to each other."

I could tell he was telling the truth. I am not sure what I thought about his answer. Was I disappointed that it wasn't more or was I happy that he wasn't completely turned off by the idea of male sexual contact.

"How about you... what is your same sex story? Or stories?" He asked.

I decided I needed to be honest with him. I figured he would either freak out because he had been flirting with a trans person, or he would be like cool, you do you and let me down easy, or he would be into trying something new. What I didn't want to do was to try and fool him into hooking with me thinking I was a girl.

I lowered my voice and leaned a little closer to him. "I uh... I need to tell you something... I hope..."

"Where did everyone go?" I heard Lisa say as she walked into the room.

"Uh... I am not sure" I said giving her a dirty look.

She didn't get the message from my eyes and took a seat on the couch. Scott came out and sat in the chair across from her. This was going to make it difficult for me and Matt to continue our conversation and I really wanted to do that. I reached for his hand and stood up.

He followed my lead and came with me as I headed towards the stairs. I sensed his eyes on by butt and turned around and confirmed it. It made me smile and gave me hope that this was going to work out okay. I saw that the door at the end of the hall was closed, that was my mom's room. My sister's door was closed as we walked by it and the noises I heard left no doubt about what was happening in there.

I got to my room and hesitated. I knew I had been introduced as Kelly's cousin but once I confessed the truth to Matt, my room would help confirm I was really a boy, there was nothing feminine about it. I took a deep breath and stepped in. I sat on the bed and patted the spot next to me and Matt sat also.

"Okay... so... here goes. I want to be honest with you and I hope this doesn't... piss you off, shock you, disgust you, or any combination of those."

"Uh... alright..."

I looked right at him. "I am really a boy under these clothes and makeup. My sister and her friend helped me pick out the outfit, and took me to get my nails done, helped with my hair and makeup. I am sorry."

"When I went to the bathroom earlier, I saw the pics on the wall. I was sure that some of them were you but then I convinced myself that it was just cousins who looked alike. You talk, move, and look like a girl... a really pretty and honestly hot girl." He told me.

"Uh... thank you. You aren't mad?" I asked nervously.

"No... surprised... definitely. Curious though... is this something new? You kind of sound like you have never done this before which is honestly... unbelievable with how amazing you look." He said sincerely.

"New... this level of it, yes. But the wearing girls' stuff, no. I have been doing that a long time."

I went on to explain to him how I had dreamed and fantasized about girl stuff pretty much all my life, my previous crossdressing experiences, and then Kelly catching me yesterday and everything that had occurred since then basically stopping when I got to bringing him up to my room.

"That is... I am not sure what it is... amazing or something. I am glad you are getting to have this experience and live your dreams." He smiled at me.

"Thank you. It has been wonderful." I took a deep breath. "I have also dreamt about.... well... other things about being a girl."

"Oh... interesting... what kind of things." His tone and play full smile made it obvious he knew what I meant.

"Well... like what it would be like to kiss a boy." I stopped to see his reaction. He smiled so I continued. "Or what it would be like to suck a boy off and to swallow his cum."

"Really... I had heard you had never done that and were curious about it, swallowing I mean."

"Yes... very curious about it. I am also curious about how it would feel to be fucked by a boy." I looked right at him.

I actually saw his throat move as he swallowed and then he leaned over to me and kissed me. He was tentative at first, but I responded eagerly, and we were soon kissing passionately as our tongues slid between our lips. He gently pushed me back and was laying partly over top of me as we made out.

The passionate kissing continued as I moved my hand down the side of his body, over his hip and then to his groin. His dick was already hard in his khaki shorts, and I squeezed it as he let out a moan. He spread his legs open, giving me more access and I moved my hand up down. I felt his hand grab and squeeze my ass.