Jimmy & Karen - Selected Again

Thanksgiving Weekend

Sunday night of Thanksgiving weekend had me tired of turkey leftovers and laying on my bed reading an American history book. Classes at the local University restarted tomorrow and the History class was on Tuesday and Thursday. I was generally up-to-date on my other classes so a closer look at the Battle of Monmouth seemed appropriate.

At just past nine, my sister Karen drifted into my room through the connecting bathroom. She was, as usual, clad in a loose-fitting wife beater shirt and a snug pair of pale-yellow panties. And, just as much the norm, I was wearing a grey T-shirt and Jockey underpants. She looked to see that my TV was off and my laptop was on the dresser. Karen took her usual position lying on her tummy next to me on my left: "What-cha reading?"

"American History, why?"

"Oh, just curious. School tomorrow, then?"

I was almost at the end of a chapter so I tried to read on: "Yes, back to classes for me and back to work for you, right?"

Karen didn't say anything. She picked up my left hand and placed it on her delightful bubble butt: "Mumble -- mumble -- mumble" in a low voice.

"What? I didn't hear that."

"Now that I have your attention; I need your advice."

I gave her sweet buns a little squeeze: "Advice on what?"

"I have a little problem."

"Ok, what's the problem? Is it with me? Your new friend Kevin? Your old friend Carmine? Or with someone else?"

"Kevin! We've been going out together since the beginning of August. I held him off for as long as I could and then, on Labor Day weekend, I gave him a little. He was a little crude. . . "

"Crude? What do you mean?"

"By 'crude' I mean that he was not as considerate as you; he doesn't always ring my bell."

"Better at it than, what's his name, Carmine?"

"Don't talk to me about that scumbag Carmine. He gets a little from me and then he runs off with that whore Sue. I hope that I never see him again."

"So what's the problem with Kevin?"

"Well, we've been doing the deed off and on for a couple of months now. He's getting better at it and I'm really starting to enjoy it with him."

"That doesn't sound like a problem."

Karen was silent for a moment, gathering her nerve: "He wants to do anal."

"Anal! He wants to do anal with you? You told him 'no,' of course."

"I didn't tell him anything other than I would 'think about it'."

"And, did you think about it?"

Karen lifted her hips a little flexing the muscles in her tight little butt: "That's why I'm here."

Wow, my sister is telling me that her current boyfriend wants to put his pecker into her pooper and she wants advice from me. I could feel a couple of stirrings down below as I contemplated the idea. While still palming her luscious ass: "I can understand why Kevin, or any man for that matter, would want to get into this. How do you feel about it?"

Karen sat up on her legs letting my hand slide back to the bed: "I'm not sure. It sounds like something exciting to do although I don't know how a woman gets anything out of it. I'm afraid that it will hurt but I'm afraid that I might really like it. Worst of all, I'm afraid that word would get around and any guy who wants to date me would expect it. Have you ever done it?"

"Me, no. I've only gotten Ginny to give me a blowjob. You're the only one I've ever had sex with."

"Can you help me decide?"

"How about we learn a little more about it? We can both learn if you like."

Karen: "Same rules as with sex?"

"Same rules? What do you mean?"

She put her hand onto my chest and got real serious: "If I decide to do it, then you will be the first. Ok?"

So, there I was, with my sister asking me if I would be the first one to fuck her in the ass 'IF' she decides to do it. It looks like my job just became convincing her that anal sex is definitely the 'thing to do' this Fall: "Yes, but only if you want to and only if we can do it without hurting you. Does that sound fair?"

Karen: "That sounds more than fair and it sounds like the brother that I have learned to trust with my body."

I was happy to hear that and even happier to think that I was again selected to exchange cherries with my sister.

Karen apparently noticed the tent in my Jockeys that betrayed my enthusiasm. She reached over and patted my cock with her palm: "It looks like you like the idea, too."

I couldn't hide what she observed: "Well, I guess that the idea is a little exciting."

"What do you want to do about it?"

I made like I was deep in thought:" Well, that all depends on you. Any suggestions?"

Karen got up off the bed and walked over to the bathroom door: "How about a 'cracker'?"

"New rules?"

Karen opened the door, stepped into the bathroom, as she pulled her shirt up and off: "Ok by me, let's go."

I was up and off the bed in a flash. By 'New Rules' she meant that ever since we had begun 'exchanging body fluids', when we did a 'Cracker', if she had the first orgasm, then she would lift up her butt allowing me to enter her vagina and fuck her while she lay there on her tummy. This new rule prompted me to do my best while rubbing her clit to get her off first. I liked the new rule.

I walked out of my Jockeys before leaving my room. The shirt came off in the bathroom and I tossed it in the general direction of my room but, I didn't check. When I got to Karen's' room she had already spread the towel on her bed and was standing there holding her phone.

"Expecting a call?"

"No. I want you to take a picture of my virgin asshole with your cock next to it. I might be able to appreciate the size difference and understand a little more about what fits where, ok?"

"What are you going to do with the picture?"

"I'll delete it after I study it a bit."

"I don't want a picture of my cock floating around on the internet."

"How would anyone know it's you if it's just your cock and my ass?"

"I don't know, but it just makes me a little nervous."

"I'll protect your privacy, dear brother. Now take the picture and let's get on with things."

Karen climbed up onto her bed and while kneeling, she bent over putting her hands down for support. I moved close enough to touch her and tried to gently separate her butt cheeks but I didn't have enough hands to do that and take a picture. She figured this out and put her one hand back pulling her cheek to the side. I pressed the other side opening her crack to full view. My cock was already rigid so all I had to do was move close enough to get my cock head and her little wrinkled opening in the frame. Click and it was done.

I put her phone onto the bed and reached for the bottle of lube while Karen put herself down onto the towel in her usual position. One good long squirt of the lube down her gorgeous crack was all that was needed. I put the lube back and promptly started rubbing the lube into her crack with my pointer finger. After a couple of swipes all seemed ready and I mounted the bed over Karen's back aligning my cock with her ass crack. As always, she felt so very good. My first thought was that I just might not win the new rules tonight, I was already close.

After my second stroke Karen lifted her right hip giving me room to get my hand down to her pussy. I was pleasantly surprised to find her already very wet and that her clit was noticeably distended before I applied my usual gentle rubbing. We were off and running quicker than on most previous occasions and it sure seemed like Karen was thrusting harder than usual.

I stayed with it and was soon rewarded by Karen going over the edge. She moaned and thrust rapidly for a few moments before pressing herself back onto me. I could feel the throbbing with my fingers and realized that I was now going to fuck her. I stopped stroking and lifted myself up a little as she arched her back lifting her crotch up high enough for me to slide my cock down through her crack and into her vagina. A few gentle pushes and I was in. Karen started rocking her hips again as I began stroking in and out of her pussy. I was really feeling good and not concentrating on anything else. I could feel my balls starting to snug up giving me the sense that I was close to my own release. A few more long strokes suddenly became a quick succession of short fast strokes which resulted in my eruption.

Karen was arching her back again letting me press in deep. I had a great orgasm and was soon on the downslope enjoying the feel of my cum oozing out of her pussy around my temporary dam. That's when I noticed that she was still throbbing; or rather, throbbing again.

"Did you cum again?"

"Yes! I like the new rules too."

I eased myself out of her and, as usual, picked up the bottom of the towel and brought it up between her legs. She grabbed the four corners with her fingers and stood back up wearing the towel like a diaper. She waddled into the bathroom and was back fairly quickly. Look Ma, no mess on the bed or on the floor!

We kissed our thanks to each other. I promised to find out all that I could about the anal question before saying my goodnight. I knew that I would sleep well.

The next day I was at Uni when I ran into a guy that I knew from High School. We had both been on the Baseball team although he was a year ahead of me. I knew that he was a psychology major so I decided to try to pick his brain. I started by focusing on having to do something that might be uncomfortable. His advice was to start slowly and to try to make it as pleasurable as possible while gradually increasing until the goal is met.

That night Karen was out with her new boyfriend Kevin so I had to wait till Tuesday to share what I had learned. We were in our usual positions just after eight. I was laying on my bed with Karen prone next to me. As usual I had my palm on her bubble butt and we were talking.'

"So, he told me that you need to start out small and work up until something as big as a cock could fit without discomfort."

"Start small? Start by sticking something small up my ass?"

"Yes, that's what he said. And, most importantly, we need to find ways of making it pleasurable for you. That way, you'll learn to like it and moving up in size will be easier."

Karen got quiet for a few moments before: "So, what small thing should I start with? And, more importantly, how will that become pleasurable for me?"

"Let's start with the small part first." She Agreed. "What is small and designed to go into your backside?"

"A thermometer?"

"Anything else?"

"Maybe that thing on the end of an enema? A suppository?"

It looked to me like a thermometer would be the smallest and I told her that.

"Ok I've had a thermometer in my butt before when I was young. I remember that it didn't hurt but how will that become a pleasurable activity?"

I thought that was obvious: "I give you pleasure while it's in you."

"Really? And how would that be done?"

"Take your pick: my hands, my mouth, your hands, your little pillow or something else?"

Karen grew thoughtful for a few moments "Ok let's say I agree. Then how would it happen if I pick 'your hands'?"

"Do we even have a rectal thermometer?"

"Yes, it's in the medicine cabinet down in the pantry by the kitchen."

"Ok, so we get the thermometer, you lay face down on your bed and I put a little lube on you and then slide the thermometer in. Then, I touch you like I do when we're doing a cracker. How does that sound?"

"That sounds pretty good. How many times before moving up to whatever is next? And, what is next on the list?"

"Maybe the tube on one of those disposable enemas?"

"And after that?"

"My pinkie finger?"

"Ah I see it now; then we can progress through all your fingers to your thumb and then to your cock?"

I decided that her plan sounded good but we might want to try some positions other than her just prone on the bed and she agreed.

She then asked: "When do we start?"

I had no answer. "I don't know, whenever you want, where was that thermometer?"

Karen said: "I know I'll go down to the kitchen for a drink of milk or something and get it while I'm there."

She was gone and back in a flash. I was still putting my stuff out for tomorrow when she came into my room holding the little glass device in her fingers: "I suppose we should use some lube, right?"

I thought that the lube that we use for our 'crackers' would probably do and suggested that we go into her room and see if our little plan worked. She agreed and headed that way with me right behind; get it? 'Behind'!

She grabbed a bath towel on her way through the bathroom which she spread on her bed in the usual 'cracker' style. She put the thermometer onto her dresser and started to strip off her clothes. I took the hint and quickly peeled out of my shirt and Jockeys.

Karen put herself face down onto the towel, just like when we do a 'Cracker'. Man, she really looked good. I picked up the thermometer and put it on the bed next to her hip. Now for the lube.

I grabbed the lube bottle off the table but Karen objected: Why not use some of that JY that's left over? The tube is in my night table drawer. I took out the tube and brought it over to where she was waiting. I spread her butt cheeks with my fingers and put the tube over her little wrinkly entrance (up until now just an exit). I tried to squeeze the tube just a little only wanting a drop or two but, as luck would have it, I squirted out enough for a full-on Cracker. There was so much lube that I couldn't see the center of her opening.

Using my middle finger, I spread the big blob of Lube up through her crack until I could make out the details that I needed to see. Next for the thermometer: "Are you ready?

"Yes, what's taking you so long?"

"I've never done this before, just hold on."

I wiped the excess lubricant from my fingers onto the towel then picked up the thermometer. Which end went in was obvious so there wasn't anything left to do. I lined it up over the center of her opening and moved it down to contact. She flinched slightly when it first touched her but was steady after that. I gently pushed down and twisted it a little as it slid into her. It went in about an inch.

"It's in, does it hurt or anything?"

"I can't really feel it. I felt it as it went in, but now I can't really tell that it's there."

"Maybe if I touch you it might let you concentrate a little on everything."

Karen lifted her hip giving me space to reach under her. I quickly found her slightly distended clit and began a gentle massage. It didn't take long before she started to enjoy my fingers. Her hips were rocking and things appeared to be going well for her. For me, on the other hand, I was standing there, bent over my naked thrusting sister with a stiff cock that occasionally grazed her one butt cheek as she moved. I soon noticed that my back was complaining almost as much as my cock; this was not the optimal position for me.

I decided to bear with it and was soon rewarded with Karen going over the edge. She thrust her hips rapidly a couple of times before pushing herself down hard onto my hand. I could see the end of the thermometer jumping up and down as the muscles in her crotch and asshole throbbed during her orgasm. I was amazed to see that.

I waited quietly as she came back down to earth. I slid my hand out from under her and finally stood up straight relieving the strain on my back. The view was still spectacular with the thermometer still sticking up between her cheeks: "That was wonderful, I could feel it inside me when I was coming, it certainly felt different, good but different."

"Shall I take it out now?"

"Please, and one more thing?"

I slid the thermometer out of her carefully placing it on her night table. I moved back getting ready to put myself down on her back for a well needed 'cracker': "What's that?"

"Come closer." I did just that. I put myself down on her back the usual way with the weight of my upper body on my arms and my cock centered in the crack of her ass. I gave one tentative stroke noting the different feel of the JY as compared to our usual lubricant.

Karen turned her head toward my face: When you come, try to come onto my asshole, I want to know how that feels, ok?"

How could I resist a request like that? I began stroking with Karen energetically rocking her hips making the process feel all that much better. The end was soon in view and I guess that she could tell: "Remember, on my asshole, ok?"

I could only grunt my agreement as the throbbing was beginning for me. She arched her back lifting her butt as I lifted myself up and grabbed my throbbing cock at the same time. I'm not sure how I managed to aim things but I had my cock head smack up against her asshole when I started to spew. I came in a surge while trying to maintain my position. Karen started shaking below me but I was too occupied with my orgasm to take any real note. When I started to come back, I put myself down onto her as I was before. This time, I could feel my aftershocks and something else. Was she throbbing, too?"

"Did you come again?"

Karen started to giggle: "I think that some of your stuff went inside me. And yes, it did make me come again, thank you."

I stood up and looked down at her ass. I spread her cheeks only to see a big blob of my cum directly over her little asshole: "And you think that some of it went in?"

"Yes, I could feel it. I think that you may have gone inside me, just a little; maybe just the tip of the tip if that's a word?"

Karen got up and went into the bathroom while I just stood there thinking about what had just happened. It didn't really feel all that different for me but she said that some of my stuff went into her. Well, that's a start, I guess.

When she came back we said our goodnights and went to bed. I slept like the dead.