Jimmy & Karen #12 - Eve of the Eve

See #10 & #11 for background

Christmas was on a Friday so, logically, the Eve was on a Thursday. Karen and I had set the Thursday as 'the day' that we would take each other's anal sex cherries. We had been fooling around with the idea and gone as far as my putting my finger into her ass as well as my ejaculating onto, and possibly into, her asshole. The date was fast approaching and the excitement was building in the both of us.

Monday night had Karen out with her current boyfriend, Kevin as usual. I had classes that day but was now free until after the first of the year. I had plenty to do as homework assignments were piled on these last few days and everything except lab work was on the list. I expected to be spending a good portion of my holidays at the library and on-line. I spent the evening on my laptop making two lists: One, all the homework that I needed to do, and: Two, all the things that I thought that I might need for the planned activities with my sister. The second list already contained: a new fresh tube of JY Jelly lubricant, a box of medicated 'cooling' pads, and a disposable mineral oil enema. The lubricant would replace the almost empty one that we had been using for our 'crackers' and anal exploration. The pads were for her to use if (likely) her asshole is sore after we do the deed. The mineral oil enema is to provide some 'internal' lubrication. I kept the list open figuring that I might think of something else before the 'big night.'

I never heard Karen come home that night. I slept in Tuesday morning not getting up till after nine. My sister was already sitting at the kitchen table when I walked into the room: "No work today?"

"No work for the rest of the week. Construction has just about stopped and the owner decided that it just wasn't worth opening the office. I have to check the answering machine twice a day; but other than that I'm done till Monday."

I poured myself a cup of coffee and sat at the table. There were pastries and some fruit so no need to 'nuke' another of those frozen breakfasts. "What are you going to do today?"

"Go to the mall and do some Christmas shopping. What about you?"

I decided that going to the mall sounded like a good idea and offered to drive. Karen accepted and we decided to do a quick cleanup of the kitchen, get changed and head out.

We were soon on our way when she said: "What are you getting for your girlfriend, Ginny?"

I hadn't picked anything specific out but thought that some jewelry was likely appropriate: "I 'dunno', maybe a necklace or something?"

"How much to you have to spend on her?"

I figured that I could budget about seventy-five dollars, or so, towards a gift. I told that to Karen who offered to help me pick something out. I gladly accepted her offer and we were soon walking through the busy mall. We found the jewelers and looked through the items until Karen spotted one that she liked and my budget liked. I made the purchase and we were on our way. "Where to next?"

Two stores down was the big pharmacy. We both had a few items on our list so we split up. I found all the things on my list and headed for the checkout up front. Karen was already in line so I fell in right behind her. She put her items onto the counter and I saw some nail polish, nail polish remover, feminine pads, a tube of JY and a small jar of adult suppositories. I said nothing and moved along as she checked out. She stood at the end of the counter and inspected the purchases that I made. We were soon walking through the mall again. Karen linked her arm through mine drawing us closer when she said:

"What's the enema for, you plugged up?"

"No, it's not for me. I read that using just a little of it lubricates your insides making the 'activity' a lot more pleasurable."

Karen nodded her understanding and guided me into the "Coffee-And" shop. We were soon seated at a small table enjoying a coffee and those outrageous cinnamon 'things' that are so gooey, sticky and tasty.

My turn: "So, if you're on the birth control insert thing, you still have a period?"

She looked around to see that no one was close enough to overhear: "No, they're for you."

"Me! Why would I need them?"

She started to giggle: "No, they're for after you do your thing in me. I tend to leak you out and these keep it from getting all over my underwear and other places."

I was just finishing up my coffee when she asked: "So, what are those little pads for? Me, I suppose?"

"Absolutely. I'm very concerned that you might feel some discomfort and they are supposed to ease things 'back there.'

"That's very considerate of you, thank you."

"And you bought suppositories? Don't we have those at home?"

Karen seemed surprised: "We do? I could have saved that money; where are they at home?"

I put on my 'smirky' face: "They're on the top shelf of the medicine cabinet. You could see them if you were a little bit taller."

"Wise ass! Anyway, they're a 'just-in-case' thing. I'm pretty regular but, just in case, ok?"

"Very OK!"

We were done and got up to leave. As we got back out into the mall, I said: "And we both got a tube of lube, great minds and all that."

We spent the rest of the afternoon wandering the mall. Karen and I separated for a half-hour so that we could concentrate on each other's gift. We met up at the appointed time and were soon on our way home with armloads of shopping bags.

Our parents were due home around six or so. I spent some time in my room wrapping the gifts while my sister claimed the family room for the same activity. There was, as usual, a list of things to 'start' for dinner as well as the suggested start times. Mom was so efficient. Karen started first but I was soon helping her in the kitchen. And, by helping her I mean doing what I could and getting in a couple of ass grabs at the same time. She grabbed my ass a couple of times, too: "Fair is fair."

The parents were soon home and dinner was served. There was a little discussion about what could be done 'around the house' while both my sister and I had so much free time. We settled on a small list which mostly included moving some things down to the cellar and finishing up the holiday decorations. Karen and I were soon alone again doing our nightly chores in the kitchen. I found it difficult to keep my hands off her gorgeous looking ass while she had her hands in the sink. Soon enough, we were done and, as usual, with the parents in the family room. Karen's cell phone rang. It was Kevin and she was soon out of the room taking her call. Almost on cue, my phone went off and it was, of course, Ginny. I excused myself and headed up to my room.

Ginny told me that tomorrow, Wednesday, was her last day of High school before the Holiday break and, if it was alright she would stop by in the afternoon to 'drop something off' for the Christmas tree. I agreed and looked forward to seeing her and was happy that I had gotten her a nice present and happier that I had already wrapped it. We chatted on for a few minutes before she 'had to get going' but left me with the cryptic: "I hope that you will be enjoying the holidays, I intend to enjoy them." I rang- off and fired up my laptop.

I tackled my email first. A few I answered. A bunch I deleted and a couple I sent to SPAM. After that, what else, a little porn. That seemed to always attract my sister and right on cue Karen came through the bathroom door. She had on her usual tight pale blue panties but, this time, instead of the wife beater shirt she had a white t-shirt with a holiday wreath printed on the front. Her erect nipples made the wreath really attractive.

Putting herself in her usual position, on her tummy next to me on the bed: "Tell me about that thing with the enema again."

I told her to wait while I searched for the article on the internet. I soon found it and invited her to sit up next to me so that we could both see the screen. I clicked the 'go' button and the article began slowly scrolling through a couple of paragraphs about anal sex lubrication. It told us that it's just as important to lubricate the 'receiver' internally as well as externally. Also, don't forget to properly lubricate the delivering 'instrument' as well. It then showed a short video of a woman kneeling on a bed with her bottom exposed. A man held a small disposable enema up for the camera before inserting the tip into the woman's asshole. He waited for a close-up and demonstrated a 'small squeeze' apparently injecting a small quantity of the mineral oil into her. The man explained: "You don't want to inject so much that the 'receiver' gets the urge to evacuate; just enough to make everything nice and slippery.

Karen asked me to run the video a second time: "That makes sense. Let me see that one that you bought."

I retrieved the device from my closet and handed it to her. She read the box and then took the little plastic bottle out for a closer look. She removed the protective cap and peered closely at the nozzle thing: "It looks like Vaseline on here."

I agreed and reminded her that we both had bought a new tube of KY.

She slid the cap back on and handed the little plastic bottle to me: "Let's try it, see if you can only do a 'little bit', ok?"

I wasn't expecting that but how could I refuse: "What position would you like?"

"Just like in that video." She stood up, slid her panties down and off and then knelt herself down on the bed with her ass held high. She moved her knees apart to about shoulder width and looked back at me:

"Well?"

Just like that! I was going to stick that thing up her ass; just like that! You 'Betcha' I was!

I could see and feel my cock stiffening as I stood there. I probably had my mouth open and maybe started drooling. Damn, she looked good: "Ok, here goes." I closed the distance to her, removed the little cap and brought the nozzle close to her pretty little pucker: "Should I put some lube on you first?"

"That thing already has lube on it."

That sounded like a no to my blood starved brain. I aimed the tip towards where I imagined her navel was, cautiously brought the tip into contact with her center and gently pushed. It went in easily. I kept pushing until all the nozzle was inside her and stopped: "Ready?"

"I can barely feel it, but yes, do it."

I gave the little bottle a gentle squeeze. When I stopped squeezing, the bottle remained slightly compressed. Apparently, there is a little valve in there somewhere that prevents anything from returning into the bottle. Isn't that clever!

"Did you feel it go in?"

"I'm not sure. It certainly didn't hurt. Can you take it out now?"

I slid the nozzle out as slowly as I could. I anticipated a little leakage but there was none. I slipped the cap back onto the nozzle and put the little bottle back into the box on my dresser. Meanwhile Karen had stood herself back up.

"I can't really feel anything other than a little tingling back there."

She walked a few steps toward the bathroom, turned and walked back: "Nothing. I wonder if it lubed me up in there?"

I was puzzled: "How can we tell? Try putting your finger in, see if you feel the lube."

If I do that, it will pick up the lube that's already on the outside. I don't think that will work."

"You're right. I guess as long as we see the level in the bottle go down that will let us know that it went in."

"That sounds good to me. Hey Wow! You've got a tent going there."

I looked down and yes, my jockeys were tented out. This seemed to be a regular occurrence whenever she came into my room: "What would you expect? What with me sticking things up your butt and all."

Karen looked at me with a quizzical expression: "Well, what should we do about that?"

She put her finger to her temple pretending to give the matter deep thought: "Well, we haven't done that mutual oral thing lately. Wanna give that a try?"

I slid my jockeys down allowing my stiff cock to point directly at her: "Does this look like I don't like the idea?"

She apparently liked the idea so much that, without any delay, she put herself down onto my bed. She lay on her side awaiting my presence. She had placed herself generally in the center so I had plenty of room to put myself into position next to her only reversed. I was soon gazing at her closely trimmed bush. I think that Karen was even more horny than I at that point. Without waiting, she drew my cock into her mouth and lifted her leg while 'scooching' over putting my face where she wanted it on her pussy. I didn't object, not one bit.

I noticed right away that she was wet. Wetter than usual and her scent was even more attractive. I kissed her lower lips and generally nosed around until she spread herself even further giving me more access to her already engorged clit. She was already sucking on me when I reciprocated. I drew her clit between my lips and rubbed it with just the tip of my tongue. That got a little movement. But, when I started sucking on it, she began a slow rocking that eventually became a gentle, but insistent, thrusting.

Meanwhile, my hands were free. So, I reached back to start a little massage on her asshole. This caused a little increase in her movements and maybe a little moan. My exploration eventually led to my pushing first my pinky and then my pointer finger into her rear opening. More moaning while the thrusting continued.

It did feel more slippery inside her. I guessed that the mineral oil had worked. I was just beginning to appreciate the success of my lubrication efforts when she went over the edge. Her climax, as always, was dramatic. The thrusting became more like lunging and her whole body was shaking. I could feel her entire underside throbbing especially her asshole. My sister really knows how to cum.

I held tight allowing her to ride it out. Meanwhile, she had stopped moving her mouth on my cock. I guessed that she had other things on her mind. She resumed her ministrations soon after she returned to earth. I was on my way but kept up my licking and fingering as events unfolded. I felt my testicles begin to snug up followed by the familiar throbbing followed up by the marvelous feeling of cumming. Karen kept me in her mouth as I delivered my essence to her. We both had a great orgasm and were soon just recovering.

Karen took me out of her mouth but held on with one hand. She lifted her leg and moved herself back away from me. That's when I realized that I still had my pointer finger in her ass; so I politely removed it and let her move freely. After a couple of moments, she quickly reversed her position putting us face to face: "Thanks, I needed that."

She giggled at her own joke which made me laugh too. We kissed for a few moments before she started to get up: "Well, was there any of that oil on the inside?"

"Yes, I think so. It sure felt a little more slippery. I was able to get in a little further. Did I hurt you?

"No, I actually enjoyed it. Looking forward to Christmas Eve!"

I asked her to wait: "I have one more thing to discuss about that."

"You're going to chicken out, aren't you?"

"No, not at all. It's the position that I want to talk to you about."

She looked puzzled: "You behind me with your cock in my ass, right?"

"Well, yes. Look, I've been reading a little more on the subject of the 'first time.' From what I can gather, it might be best if we do it more on our sides, like in the 'spoons' position. They say that it is a little easier and lets the woman, that's you, have more control of the activities. Understand?"

Karen sat herself back down on the bed and looked attentive: "Tell me more."

"If we do 'spoons' I can go slow and you can push back when you're ready. You can let me know when I need to stop pushing and you can even just move away if it hurts too bad. I really don't want to hurt you."

Smiling: "I understand your concern and I defer to your judgement. So, the 'three pillows' is out?"

"At least for the first time."

Now she put on her big sister face: "And, what makes you think that there will ever be a second time?"

That made me laugh: "OK then?"

"Yes, but while we're on the subject, just how do you see the events going?"

Mocking her usual wise answers: "You know, my cock. your ass, pump, cum."

"Touché wise guy. Really, give me an idea of what to expect."

"Well first, your place or mine?"

"Place? I thought that we were going to fuck my ass not yours."

"Look what I've started. Your room or mine?"

Karen actually stopped to think about that for a moment: "My room."

"OK. How will I know when you're ready?"

"How about if I come in here and you do that 'lubricating' thing then we go into my room for the main event?"

I proposed a counter offer: "How about if I start with a nice massage which leads to my doing your boobs, which leads to me going down on you."

"I like it so far. Where would this happen?"

I was tempted to say something wise but opted to let this one go: "I think that it would be best on your bed; it's a little bigger than mine."

"OK, then what?"

"Well, while I'm going down on you, I administer the little internal lube job."

"OK, then?"

"After you have a good cum, I'll offer you another one."

"Two in one night?"

"You want to have good memories of the night. Besides, if one relaxes you what will two do?"

"Two might make me pass out!"

"I doubt that, but we'll see. Anyway, I'll apply the KY while I'm doing the second one after which you just roll to your side and I will move up behind you."

"Ok, now we're getting somewhere."

"I will put some of the KY on me." She interrupted: "Why can't I do that?"

"Then I will get into position and center myself on you. When you're ready, you push back a little and I will push at the same time. You put your hand on my thigh and control the action by pulling me towards you or pushing me back. How does that sound?"

She gave it a little thought before: "That all sounds good. But, can I make one request, no two requests?"

"Sure."

"First, let's try the position just to see how it lines up."

My sister put herself down onto the bed with her back toward me. She bent herself at the waist and brought her knees up a little. I got down onto the bed behind her and moved to make contact. The first thing that we both noticed was that, since my hips are wider than hers, my cock didn't line up with her ass crack. She lifted herself up and put my pillow under her hips. We tried it again and the fit seemed perfect.

After we had confirmed the arrangements, she got up off the bed and walked over to the bathroom door: "And Second, after you're all the way in, I want us to roll me over onto my front with you on top of me. When we get that way, I really want you to give me a good fucking, OK?

With that she was gone for the night. I waited for her to finish in the bathroom and then went in to take my shower. Early night but not easy to sleep.