Jimmy & Karen - A Little More

We didn't get together again for a few days. Karen had been out with Kevin a couple of times and I saw Ginny on Saturday night. Ginny was still reluctant, scared I think, to have sex but was willing to not only give me an occasional blowjob but to let me finger her to orgasm. At least I was making progress on that front.

Sunday night had me in my room getting things ready for another week at Uni. I had my laptop going and I was putting the final touches on an email which was to carry my latest interpretive essay on the war of 1812 logistics to my professor. It wasn't due till Thursday but it had been my experience that he was a lot more lenient marking early submittals. Just as I pushed the send button Karen came through the interconnecting bathroom into my bedroom.

"Yo bro! How's it going?" As was her routine. she was wearing a loose-fitting wife beater shirt and a snug pair of almost transparent pale blue panties. As always, she looked good.

"Fine here. How are things going with you and Kevin?"

"Well, he hasn't gotten into my ass yet if that's what you're asking?"

I had that in the back of my mind but thought better of asking the question directly. I moved over a little giving her room to sit and then lay herself on my bed. She was looking at my laptop and asked: "What-cha doing?"

I showed her that I had my Uni email account open and that I also had my essay open in the word processor application. She politely pretended to be interested before asking:" Got a lot left to do tonight?"

I told her that I was just about done and only really needed to close out the apps.

"Then what?"

I asked the same question: "Then what?"

"Talk for a while?"

"OK by me." I lowered the cover on the laptop and slid it onto my night table: "What's the subject tonight?"

Karen knew how to get my undivided attention when she wanted to. She rolled over onto her tummy and lifted my hand putting it directly onto her beautiful bubble butt: "What's next on the list of getting me ready for anal?"

I almost blacked out from the massive diversion of blood from my brain directly to my cock. As usual, I started to tent out my Jockeys. Karen had that smug look on her face as she looked down my front confirming that I was, in fact, paying attention to her. "Well, before we move on sticking things up your ass, how about looking at an interesting video that I found about a girl who, like you, wants to try anal sex?"

"Yes! I'd really like to see that. Can you put it onto your laptop?"

I agreed and we were soon watching this young woman and a camera operator doing normal sex. She was kinda kneeling on the end of a bed with her upper body propped up on what looked like three or more pillows. The camera guy was standing on the floor fucking her at a moderate pace while the girl was chatting casually to him. They were using multiple cameras and split screens since we could see the girls face from the front and the cameraman from the side as well as close ups of his cock going into her by his hand-held camera. She told him that she wanted to try taking it up her ass which caused the camera guy to pull out of her pussy. He picked up some lube from somewhere, applied it to her asshole and his cock and then proceeded to push himself, slowly, into her ass.

The expression on the girls' face turned from expectant to attentive to discomfort in just a few seconds. The guy pushed himself a couple of inches into her and stopped; likely allowing her time to adjust to the intrusion. After a couple of moments, he started to push in a little further but the girl seemed to be in serious discomfort. He stopped again but, after a few more moments, she said that it 'really hurt' and would he 'please take it out'. He withdrew and the girl slowly got up holding her hand over her recently invaded orifice.

The girl walked naked around the motel room talking to the camera guy. They discussed what they were doing and her curiosity about the act. Finally, the girl decided to 'give it one more try, and got back on the bed with her torso on the pillows. The camera guy applied more lube to her using what looked like an adult size ear syringe. More lube went on his cock and he was soon aligning himself for a second insertion.

The girl had a more determined look on her face as the camera guy began to enter her once again. She grimaced, frowned, showed wide-eyed shock and finally resignation as his cock slowly regained its former position in her rectum. A couple of additional pushes had him just about all the way in while the girl continued to stare into the camera with only a slightly uncomfortable expression. Then the fucking began.

After the first few long strokes the camera guy seemed to establish a rhythm. The girl reached back grabbing his one free arm (The other one was still holding a camera) and brought his hand around to her pussy. Once he started fingering her pussy, she started to rock her hips and they were doing the deed together. Her facial expression soon turned to a 'surprised that it felt good' look which included a little smile. They fucked on for a few minutes before the sound of the camera guy's breathing indicated that something was going to happen. A close up of his cock showed it pulsing while he voiced a low moan. The girl's face showed a wide-eyed happy expression as she looked directly into the camera while taking a load up the ass.

The camera then showed his cock being pulled back out of her ass and the ensuing leakage of cum that followed. The girl was happy that she had 'finally done it' and the camera man was less committal only offering her the advice that she should go into the bathroom and 'push that cum out of your ass'.

I turned the video off at that point not needing to see the girl sitting on the toilet. Karen was still looking at the laptop screen after it went to black. She finally looked up at me: "Just like that, they did it without all the stretching and preparations?"

I told her that it certainly appeared so but we couldn't be certain since it was only a video. For all I knew, she could have been a regular anal enthusiast and only claimed to be apprehensive for the sake of the video.

Karen wasn't so sure: "Her asshole looked tight to me. I think that if she was a pro that it would be a little 'looser', if you know what I mean."

I understood but remained uncommitted. I closed up the laptop again and slid it back onto the table. Karen rolled back onto her tummy and when I turned myself to face her, I put my hand back onto her butt: "Wait a minute."

I pulled my hand back. Karen got up off the bed, stripped down her panties then stepped out of them. She put herself back down as she was before and said: "OK now put your hand back."

Her naked butt felt as good as ever. I gently massaged her luscious cheeks as we continued to talk.

"So, you think that just going for it would work?"

I wasn't expecting that: "No, I just thought that you might like to see that video, that's all."

"But he went into her without any real preparation."

"Other than just fucking her."

"Oh yeah, he was doing that." She thought about something for a couple of minutes before saying: "I have an idea."

She was up, into her room and back in less than a minute. When she returned, I could see the half tube of JY in her hand. She handed me the lube and sat herself on the bed: "Ok, you put a little of this onto me and then put your pinky into me. This is for you to judge how tight I am. Then I will do the same."

"You're going to put your pinky into me?"

"No, silly. I will put my pinky into me just to see the same thing as you, understand?"

I nodded my understanding.

"Then we fuck, just like in that video. Then we check me for tightness again."

I was already liking the idea but had one question: "Just like in that movie? We'll need more pillows."

She was gone and back in almost the same time. I now had a total of four pillows on my bed.

"Help me figure out how she had them arranged."

We stacked the pillows near the edge of my bed. Somehow it didn't look right so we moved them to the foot of the bed. They looked better there. Karen got up kneeling on the very edge while placing her torso on top of the pillows. Four were too much; she felt like she might roll off to the side. We removed one pillow, tried again before she declared it 'perfect'.

"How are we going to do the test?"

"C-mon Jimmy. You know, your cock in my pussy then we fuck."

"All-right, let's not start that game again. I meant the tightness test. Kneeling, standing what?"

"It's got to be some way that I can reach easily. Maybe standing?"

"Ok by me. Let me know when you're ready."

Karen turned her back to me and leaned forward a little: "I'm ready. Now, just your pinky, ok?"

I agreed. I put a modest blob of the JY onto my right pinky before moving close behind her. Karen reached back with both hands and separated her butt cheeks. I carefully put the tip of my pinky on her asshole and twisted it a little to spread the lube. With my other hand on her hip, I pushed my pinky into her asshole up to the first knuckle. She was really tight: "Are you clenching?"

"Just a little; wait, there, can you feel the difference?"

I could, but she was still pretty tight. I carefully removed my pinky and wiped the lube off with a Kleenex. Karen turned to face me before reaching behind herself with her hands. I couldn't see what she was doing but she soon stopped moving and looked me straight in the eye: "You're right, I'm pretty tight." She used a Kleenex for the same purpose.

Karen was about to get back up onto the bed when she stopped: "Wait, please go wash your hands before you touch me down there." That made sense so I took my dirty pinky into the bathroom and washed it. When I went back in, I thought: 'What about her finger?'

She was already kneeling in position when I got there. I decided to move on with the fucking and not quibble over things like that.

"Are you ready for me?"

"Loosen me up."

I moved up behind her. I first just admired her beauty and then smelled her arousal. There was still a little lubricant remaining on her asshole but it was the natural lubrication on her pussy that was attracting me. My rock-hard cock was pointing to where it wanted to go. I moved closer and ran my cock head up and down through her moist slit until it centered itself on her opening. A little push had me half way in. Before I pushed the rest of the way in, I remembered the discomfort that she had felt when I fucked her while she had knelt on our parents' bed: "Don't let me hurt you like this."

"Just go slowly, I'll let you know."

I reached around her hip putting my hand down into her crotch. Her clit was well distended and I started applying gentle massage as I started some slow-easy strokes of my own. I was soon well seated inside her and, without hearing objection, started with a few longer strokes and even a couple of 'all the way in pushes.' Still no indication of discomfort; apparently this position moved things around internally getting the sensitive parts out of the way.

Karen was rocking her hips in time with my thrusts and we were enjoying a leisurely fuck.

I wanted to hold out until she had a good orgasm but the pressure was building rapidly in my balls. I increased the rubbing on her clit until she said: "Not so hard, I'm getting close."

That was good news! I kept my cock sliding in and out of her at a moderate pace waiting for her to peak. After another minute or so the signs started to appear. Her hips were rocking more energetically, her breathing changed from deep to short gasps and she started to moan a little. Karen went over the edge and I could feel her whole underside throb around my cock. I snuck a peek down and could see her asshole pulsing. It looked like it was moving in and out in time with her other parts. She had a nice long cum while she pressed herself back against me and I was just about there myself. I slowed to nearly stopped while she enjoyed the aftermath and we were soon almost still with my cock deep inside her. Karen lifted her head: "Did you cum?"

"No, not yet. I was waiting for you."

"Can you do that thing where you put yourself at my asshole when you cum? That was really neat and, if you hadn't noticed, it made me cum again."

I promised to try. I resumed the fucking with some long strokes but, as usual, the short fast strokes soon overtook me. At the last moment I pulled back grabbing my cock and pointing it at her asshole. The first squirt of cum shot out hitting the target. I pushed forward as the next couple of spasms seemed to give Karen her wish. I had a good cum but, when I looked down, the head of my cock was almost all the way into her asshole. The ridge at the bottom of the head was just about even with the outside edge of her opening. That meant that at least the head was more in than out. I must have put most of my load of cum into her bowels!

"What just happened? Was that you or me? I felt a throbbing back there, I've never felt that before."

I couldn't explain it. As I pulled back, I could see her asshole covered in cum but with just maybe a tiny opening at the center. Was she open? Did I really just shoot cum into my sisters' ass? As I looked, the oozing cum seemed to stop and what I thought was an opening seemed to close up: "I don't know. I just might have."

Karen got up off the bed and faced me. Her expression was both surprise and elation. She kissed my lips: "I think we succeeded in getting some of your stuff inside me." She reached back, apparently retesting her tightness. Her eyebrows went up and she smiled: "Definitely looser, feel"

With that, she turned around presenting her butt to me. I didn't hesitate for a second. My little finger went in, without much resistance, up to the second knuckle. I withdrew it: "Definitely looser!"

She was smiling and obviously very happy: "We did it, next step all the way in!"

I was a little more cautious: "Did it hurt?"

"Not at all. In fact, I kinda liked it."

"You do know that it was only just the tip of the head that was in you, right?"

"Isn't that as big as the rest of it?"

"Maybe in diameter. But there was still all the rest of my cock on the outside. It might be different if we tried to stuff that into you."

Karen thought about that for a couple of seconds before agreeing: "Well, maybe so. The part that didn't go in was actually most of it. But we did make some headway, right?"

"Headway? Are you sure that you want to use that word?"

She giggled at that: "Am I supposed to go 'push the cum out of me' like in the video?"

"At the very least you should wash your hands and maybe 'wipe up' the scene of the crime."

We spent the next few minutes returning the pillows, lube and discarded clothing to her room. After that, she closeted herself in the bathroom for a few minutes. I had gotten into bed thinking that she was done for the night. Soon enough, the door opened again and she came into my room to kiss me goodnight.

I asked her if there was any discomfort 'back there'?

She said no. She felt fine and was ready for bed. She only had one additional request.

"Ok, what else can I do for you?"

She got really serious, looked me in my eyes: "Let's set a date that we will do full anal. Ok?"

I was stunned but agreed. I suggested that we look at the calendar and figure something out tomorrow after dinner. That plan was 'just fine' with her. I didn't sleep well that night/.