The Problem with My Sister Ch. 02

Thursday Morning...

Having said goodbye to the family again Leanna and I were headed toward the city. We stopped along the way at a local nature center for a good hike and just to hang out. The conversation was blended with everything from our new family dynamic to eastern philosophy and the concepts around living in the moment. The rest of the day was to include a late lunch after the hike and then arriving at the hotel mid-afternoon for spa treatments before the big event. Leanna had this so well planned that we should be finished at the spa around 4 pm for room check-in.

"I have booked you a massage and then a pedicure because your feet look like shit."

Giving her a little shit I replied in a whiney voice, "But mom, the other Marines will make fun of my pretty feet."

"Very funny asshole. They will be anything but pretty, just less ugly."

"Speaking of assholes, I can't wait to get inside yours tonight."

"Very smooth casanova, but it won't be tonight," she paused longer than I liked, "It will be this afternoon, as soon as I'm done with my massage that way I'm totally relaxed."

"You have this so well planned sis."

"And, after you have robbed my ass of its virginity, you are taking me out to dinner...someplace nice."

"That's a fair trade. Should I get a reservation?"

"Already done loverboy," she replied through a smile and another of her winks that I have grown to love.

The lunch was low-key and surprisingly no drinking. She said she wanted nothing that might keep her from experiencing 100% of the sensations coming her way this afternoon so I played along. By the time my massage and foot treatment was finished she was already in our hotel room in a very short satin robe and from what I could tell, nothing else. I noticed candles burning, the shades tightly pulled, and a bottle of lube on the nightstand. She was sitting on the bed and she instructed me to sit in the pullout chair by the desk. I realized this was similar to the setup for our first night together.

"Josh, you've been a very good sport this week giving me all of the orgasms while you were going without so I'm not going to make you wait any longer. I do have some requests on how I want this to go based on my research if you will."

"I am at your service my lady."

"Very well. I won't need much foreplay really because I have been in here getting myself warmed up so to speak for the last 30 minutes. I'm going to roll over on my side and I want you to use a liberal amount of lube on both of us which is why you see a towel beneath me. Then I want you to spoon me and when your cock is hard enough I want you to enter me."

"I don't think being hard is going to be a problem." We both laughed because it was obvious that I was already there.

"Good, then I want you to pay attention and do as I say. I may hate it or I may like it but either way, you are the first person to do this to me and that's something nobody can take from us."

"I feel honored and privileged to be part of this."

Laughing, she said, "You are always so proper."

"Respectful is what I would call it. I have always respected and admired you and it's indescribable the joy I receive from our times together."

"Aww that's sweet Josh. Now, stop being so nice and get over here."

She started to roll over but maintained eye contact while pulling up the back of her robe.

"Now make proper love to my asshole and fill me up with the week's worth of cum you're carrying around."

"I would love nothing more," was all I could say as I approached. I finished shedding what I was wearing and reached for the lube. I could see that when Leanna had rolled over halfway on her stomach with her top leg bent she had worked one of her hands down to her pussy and was slowly rotating. I gently applied a liberal amount of lube to her anus and worked in a finger and then two to see how this was going to go.

"I think those butt plugs have you very well prepared or you are just extremely relaxed."

"I think the butt plugs were fun but wanting this to be enjoyable combined with this spooning position is the way to go. The mind is a powerful tool."

"Indeed it is."

I had joined Leanna on the bed spooning up behind her ready to attempt entry.

"Any last words before I take your anal virginity?"

"Take it slow and enjoy every little sensation like I am. I want you to remember on your deathbed the day you bred the virginity out of your big sister's ass."

She had such a way with her hot talk. I eased the head of my cock up to the entrance and she jutted her hips back to receive me in her opening. She moaned instead of yelling which I took as a good sign. Even though it started relatively easy I wanted to be careful to be sure I was lining up well with her canal to not cause any pain. She too was easing into a slightly different position to make all of the inner workings fit. Before I knew it I had bottomed out with my entire cock buried in her ass and I swear I could feel our heartbeats meshing together.

"Stay right there for a minute, don't move," she whispered.

"Are you ok?"

"Better than ok. Can't you feel that? How your cock is perfectly positioned in my ass?"

"I thought it was just me but yeah, we feel very connected."

"You know we came out of the same womb, made of similar sperm so why wouldn't we think this would feel so perfect?"

"I honestly never thought about that. We are made for each other."

"Yes we are," she breathed as she started to slowly rock and squeeze her ass around my cock.

"I think it's time we dispensed with the philosophy and you got back to fucking my ass. Until you've dumped your load in there I'm still counting you a virgin."

"Ok but I'm still going to take it easy. I don't want to wreck you right out of the gate and this isn't going to take long."

"I am way ahead of you," She said as I noticed her buried hand was busy on her clit and her breath had increased. We started moving in unison as her orgasm arrived and I felt her ass spasm on my cock. That put me over the edge and I told her so.

"Fill me up like the ass fucked slut you've turned me into."

That was it. I came so hard and long I thought I had broken something. When we both came down we laid there like we were for quite a while.

"Thank you for making an honest woman out of me, Josh. You were so gentle but also strong at the right times. That was perfect."

"I have to say I am a little surprised as to how that went."

"Now I want you to do something for us. I want you to slowly exit my ass and grab your phone. I want you to take a closeup of my asshole with your cum dripping out. A memento for you to remember this moment."

"Aren't you worried about the evidence?"

"You're a guy, you can say it is anybody which is the reason for the close-up. Only you and I will know the truth."

I did as she instructed and then she clamped her ass and said she wanted to keep the rest in there as long as possible. Then she had another thought.

"Grab my bag over there and find the butt plug I used today."

"You've had a butt plug in all day?"

"Surprise! It seemed to work too. Now I want to use it to keep your cum in there during dinner."

"You're the boss."

Dinner was at a nice place within walking distance. After we were seated Leanna seemed distracted so I asked if anything was wrong.

"No, not at all. Just rolling an idea around in my mind."

"Care to share?"

"It's just that," she paused, "I think you should still be dating."

"For what purpose other than providing cover for what we're doing?"

"I think you should continue on with your life and let our relationship be secondary. I know it seems crazy but I think it would help us become stronger if our connection parallels our relationships that are considered normal."

"Nobody that I have met would even come close to giving me a satisfying life when I have you to compare them to."

"What if I already knew somebody?"

"And who would that be?"

"You remember Ashley. The girl I train with?"

"Isn't she gay?"

"Why would you say that?"

"Well, she's my age and still single, plus she could do nothing but watch you the one time I visited you guys at the gym."

"She was just trying to learn the moves and no, she's not gay. Have you seen her recently?"

Reaching for her phone and flipping through some pictures, "Here's a recent photo."

"Wow, I thought she kind of looked like you before but wow, you two could be sisters."

"Now you're catching on," she smiled and gave me that wink again.

The waiter arrived and we dropped the topic other than agreeing to meet up with Ashley on my next leave. After dinner, we retreated to the hotel for what would have been considered some sweet and sensual lovemaking, a little tamer than everything we've done to date. We slept tangled up in each other's arms not waking until the sun was peeking through the window. I still had a flight to catch and Leanna reminded me that we needed time for our pre-trip ritual. So we parked in the same area and she sucked me off one more time before walking me to the terminal. Now being in the public eye we had a good hug and exchanged kisses on the cheek.

"I guess I'll see you for Thanksgiving right?" she asked.

"That's the plan."

"Just remember what's waiting for you when you get home."

"It keeps me going every day. Enjoy lunch with your friend."

"Yeah. Hey, you know I still love you like a brother and not just a lover right?"

"I figured you did. Same for me."

"So it's like I'm missing two people while you're gone."

"Yeah, I get that."

"Good, so be extra careful and make good decisions," she said through a growing smile and a wink.