Jimmy & Karen #10 - My Room

The next night had us together again, as usual, in the kitchen doing our nightly duties at the sink and dishwasher. As the work completed, we drifted out into the mud room where the official family calendar was hanging. Karen wanted to set a date for our first full attempt at anal sex. The calendar was pretty full of appointments, activities and events for the next few weeks but one date stood out: Christmas. I would be off from school and Karen would be off from work on the eve and day of the holiday.

Karen: "Christmas day when Mom and Dad go over to grandmas?"

"They'll expect us to go with them."

"Christmas Eve while we're waiting for Santa?"

"Won't you be on a date with Kevin?"

"Not if we're finally going to do it. It would certainly be an easy date to remember."

"Like the Fourth of July"

"Actually, the first time was on the third."

"I stand corrected."

"Right, you stand and I kneel on the bed."

That did it. I gave her ass a good grab and headed her back into the kitchen. One final check before we declared the mission done. We joined up with our parents in the family room for a little 'tely' before we went up to our rooms at about eight thirty.

I checked my email. I replied to a few and deleted a bunch. I was getting a lot of spam. I suspected that it had something to do with my email address being through the University. Oh well, best to be safe. Just as I was closing out of the email Karen came drifting in through the bathroom, as usual.

She sat herself on my bed right next to me: "Watching some porn?"

"Not currently, I was checking my email."

"Want to watch some porn?"

"Sure, what topic would you like to see?"

"Let's watch some guy do a babes' boobs and then go down on her."

I submitted a search and came up with a few candidates. I let her pick one and started it. She snuggled a little closer as we watched. After a couple moments she said: "You do it better than that guy."

I thanked her for the compliment: "But, there's always room for improvement, right?"

"You do very well; I always cum don't I?"

"It seems so, but, tell me, is there anything else that you would like me to do, or stop doing, or do differently?"

"Just do it a little more often."

I was surprised: "Really, you would want me to go down on you more often?"

"Maybe just a little. And as long as we're discussing things like that, can I make a request?"

I turned the laptop off and slid it back onto the table. I wanted to give her my full attention: "Name it."

"Can you make love to me?"

"I thought that we were doing that. "

"No, we're just fucking. I'd like you to make love to me, not every time but, once in a while."

"I'll do anything that you want; just let me know what that is."

Karen got thoughtfully quiet for a few moments before: "Kevin and I have gotten closer but we're still only fucking. We go to parties where he drinks too much then only wants to grope me as foreplay and then get himself off as fast as he can. Or we go to the movies and he stays sober but when we go parking it's the same thing. I want to lay down in a bed, do lots of foreplay and then make love. And, I want you to cuddle with me afterward and sleep with me and spend the night."

I was surprised to hear this request from my sister. The description of her sex life was a little sobering to me and made me understand why she has continued to cling to me even though she has a steady boyfriend. I resolved to do the best that I could for her and said: "Karen, if that's what you want then that's what you will get. When do you want to do that?"

She moved closer and gave me a nice kiss: "Thank you, I want you to surprise me. Just come into my room in the middle of the night. Get into bed with me and make love to me. Stay there when were done and sleep with me. I get up before you do so I can wake you and send you back to your room so that all will seem normal. Ok?"

"Not tonight?"

"No, tonight I just want you to fuck me. Are you Ok with that? Wait, don't answer that, just let me check." She put her hand onto my Jockey covered cock feeling that it was about half way rigid: "I'd guess yes."

"Where do you want it?"

"Right here in my pussy, we're not going through all that, again are we?"

When she started busting my chops, I knew that the serious part of tonight's' conversation was over. I hugged her close to me feeling her hug me back. I kissed her a couple of times, before sliding my hand down to pull her waist closer. As you may have guessed, I did that by putting my hand directly onto her cute bubble butt.

I rolled over onto my back bringing her with me. She was now laying prone on my front and we both enjoyed this rarely felt experience. I slid my hands under her shirt and assisted her in taking it up and off. Her bare tits felt so good pressed against my chest. Her nipples were stiff and she responded to my fingertips rubbing them lightly: "Mmmmm that feels good."

I encouraged her to slide up on me putting her nipples directly over my face. I kissed and then licked and then sucked them. Her low moaning continued as I paid more and more attention to her beautiful firm tits. I was in no hurry to move on and I sensed the same from her. My hands were free so I rubbed her lower back and occasionally across her firm butt. I ran my fingers under the waist band of her panties a couple of times which prompted her to lift her hips up and slide them down a bit. I took them the rest of the way and they were soon down and off.

Karen was now totally naked and laying on top of me. While still enjoying her boobs, I moved my hands to her waist and pushed up trying to encourage her to slide even further up my front. I had the intention of going down on her again only this time with her on top of me rather than on her back.

"I'm about as far up on you as I can get. If I go any further you won't be close to my boobs."

"That's exactly what I want, move up and sit on my chest."

"What? Like with my pussy on your neck?"

"No, with your pussy on my mouth."

It seemed like Karen was having a little trouble visualizing what I was suggesting: "Do you want me to draw you a map?"

"You want to go down on me with me on top?"

"Exactly, haven't you seen that on one of the pornos?"

"Not that I remember, let's see one!"

"How about if we act one out. Just slide on up and put your legs over my shoulders. You will have to bend your knees a little, and I'll slide down the bed a little."

"Turn off that reading light, ok?"

I switched off the light and we then moved into the position that I had suggested. It took a little adjusting but, I was soon face deep in woman parts. Karen leaned onto her hands and then down to her elbows while I got oriented with the new position. Her scent was, of course, more concentrated like this and I could feel myself getting even harder as I explored.

I held the cheeks of her ass as I explored her with my tongue and lips. It took a few moments to locate her clit. I'm guessing that it had retreated a little during her confusion and our maneuvering; but, once I found it and started massaging it with my tongue It regained its distention and, just maybe, was just a little bit more engorged. I soon had her clit between my lips and was happily sucking on it while my sister was gently thrusting against my face. My chin was just about lined up with her vagina and I could feel a bit of her moisture running down my neck.

I let my fingers drift over to her ass crack and started a gentle massage of her asshole. This coincided with an increase in her thrusting; coincidence? Anyway, Karen was energetically riding my face and I was beginning to sense her impending release. Knowing how she tenses up when she comes, I started taking deep breaths anticipating a temporary cutoff of my air supply. Sure enough, she went over the edge dramatically.

Her last thrust was more like a lunge. Her thighs came together and her entire underside started throbbing. I could feel an increase in her moisture along with the throbbing of her asshole against my fingertips. She let out a low moan and rode it out for what seemed like the longest orgasm that I had ever witnessed for her.

She took a while to come back to earth: "Wow, that was wonderful. What can I do for you?"

I didn't reply right away, I still had a face full of pussy. She lifted up and slid herself back down staying on top of me. When we were face to face, she kissed me deeply before saying: "Wow, was I that wet?"

"It seems as though you liked that."

"I did and now I want to give you anything that you want? Just name it."

I thought for a quick moment: "Can I have two things?"

"Probably, what are they?"

"First, just like you want me to come into your room and make love to you some night; I'd like you to come in here and put yourself into that same position. Just put your pussy on my face and let me please you again. No talking, just sex. Second, I'd like you to get up off me and put yourself face down on the bed with my pillow under your hips. Then I'd like to fuck you for a few minutes, how does that sound?"

She lifted herself up and lay down next to me. I slid down the bed and got off at the foot. I turned to see her pulling my pillow down under her hips raising her butt into the most inviting position. She spread her legs and waited patiently for me. I knelt on the bed and lowered myself until my cock was sliding in her crack. Karen raised her hips a little more giving me plenty of room to move my cock down through her split until I lined up with her vagina. One push and I was in an inch or so. Then came the long glorious push as I went the rest of the way. We were soon fucking in a most delightful rhythm.

The end arrived sooner than I had anticipated. With one great push I unloaded my balls into my sister's cunt. I hadn't thought about the 'fallout' but, sure enough, some of what I gave her soon ran back out and ended up on my pillow. Oh, well, it was still a great cum!

"Why didn't you squirt that into my ass?"

I hadn't even thought about doing that. Looking for a quick excuse: "We hadn't put any lube on you. I was afraid that it might hurt." That seemed to satisfy her as she squeezed by cock and balls between her thighs and ass cheeks in a very appreciative way.

It soon became obvious that it was probably getting toward bedtime for both of us. Karen got herself up, dripped a little more onto my sheet and floor before kissing me goodnight: "I need another shower" and she was off. She closed the bathroom door behind her. I was just fucking her and now she's going to be modest? I had to wait for her to finish in the bathroom before I could go in and wash my face which was, obviously, strongly smelling of pussy. I straightened up my room and was asleep in about ten seconds. I slept with the cum stains on my pillow on the bottom.