Chapter 4

The next day, Jen came to my room, and clearly was really upset. I sat her down, gave her a big hug, and asked her what was wrong. She just let it all out: her guilt about initiating a relationship with me, her guilt about doing anything sexual at all--too young, she felt like a slut, and then she dropped the bombshell; she told that that she was afraid that she was into pain.

She explained that the times that I put my finger in her ass, that it hurt like crazy, but she absolutely loved it. She even told me that when I had swatted her butt the other day, she had orgasmed. Jen wanted to confront the issue head on, and had an idea. She wanted to be spanked, lightly spanked, completely clothed, but nonetheless spanked. In some weird way, she seemed to think that this would help.

I really loved my sister, and would do anything for her, besides, anything that allowed me to touch her backside, would be just fine with me.

We agreed on the rules: light spanking only, over her clothes, no skin on skin, no sex play. She was wearing denim shorts, so they offered some protection, and this seemed like the ideal time to try.

I got my desk chair out, put it in the middle of the room, and sat down. She draped herself over my knees, with her head to my left, and her feet to my right, and the object of my affection right under my eyes. She was wearing a fairly modest top, but her shorts were pretty short, old-fashioned denim, and they did a great job of encasing and accentuating her beautiful ass.

I gave her a light swat, and she giggled, and told me I would have to do more than that. So, I gave her a good swat, and this got her attention; her head came up, her ass jumped, and she squealed. The next blow was just as hard, and she started moaning.

By now, I was seriously erect, and she kept rubbing against it. Her ass was really moving around, and she had started crying very softly. After about 25 swats, my hand was starting to hurt; the denim was rough, and had rivets. On the other hand, she really seemed to be enjoying the whole thing. She was crying nonstop but kept wiggling her ass, and it almost seemed like she was lifting it up to meet the next swat.

We stopped for a short breather, and I showed her my hand which was really red. In response, she told me that she wanted to lose the shorts. Against my enlightened self-interest, I argued that we had agreed that she would be clothed. She nodded her head, but said that panties covered all the important stuff, kind of like swimsuit bottoms. Also, she said that my hand wouldn’t take much more, and if she took off the shorts, it would be easier for me.

So, she stood up, and seemed a little surprised that I reached out, unsnapped and unzipped her shorts. They were too tight to simply slide down, I had to get my fingers into the legs, and walk them down. Once they came down a ways, I was able to easily slide them down her perfect legs.

This left her only protected by a tiny pair of translucent panties, and I could see a wet spot between her legs. As soon as the shorts came off, the faint musk scent that had been in the room, became much stronger. She really did like the pain.

Again, she delicately placed herself over my knees, I started spanking. Once I could see the effects that the spanking was having, I was in heaven. The first spank landed on her right cheek, and brought an immediate yelp of pain. It also caused the cheek to jiggle wonderfully, and shortly after, I could see a faint reddish hue through her panties. The next spank landed on her left side with about the same effect. I alternated back and forth, sometimes higher on her ass near her hips, and sometimes closer to her legs. Compared to her ass, I had pretty big hands, so some of the swats landed squarely in the middle.

After about 12 swats, I was a little winded, her crying had reached a fever pitch, and I wanted to assess the damage, so I stopped and just caressed the object of my affection. It was boiling hot, and red as a beet. If it was possible, as I was caressing, she was dancing around even more. Reasoning that she had taken the first 12 with no problems, I started again.

I had to grip her with my left hand to hold her down, and it was wonderful watching her legs kicking flailing around. Her panties were soaked, but her ass seemed to rise up to meet every swat. When I finished, she was crying, I mean really crying, and once I realized this, I felt like a total jerk, and stood her up to give her a hug.

She gripped me like I was her lifeline, and cried on my shoulder for at least 10 minutes, and then between sobs and hiccups, she told me that she wanted to be spanked totally naked, and she really wanted the spanking to be pretty hard. She also admitted that several times she had almost asked me to stop because of the pain, and she didn’t want to risk stopping the spanking prematurely, so we agreed on a safe-word, rex. Unless she said that word, I was to ignore any pleading or crying.

By now, we’d reached an unspoken agreement that I was in charge of removing her clothing, so she just stood there with her head down while I unbuttoned her shirt and exposed her bra covered breasts. Her nipples, must have been hard because they were clearly visible poking through the fabric of her bra. She had turned around so that I could reach the clasp of her bra, so when I was ready to remove her panties, she was facing away from me. She winced when I started peeling them down, and I understood why; her ass was red and blistered.

I know it was against the rules, but when her ass came into view, I just couldn’t help myself, I gave it a couple of kisses. She didn’t seem to mind though; she did a little leg wiggle. When she turned around, I could see that her nipples were puffy and beautiful. Her muff, thanks to my help with the razor, wasn’t a muff at all, just two really nice camel toes. I desperately wanted to suckle her beautiful tits, but I had already crossed the line when I had kissed her bum, and I felt like I had to refrain.

We agreed on 25 hard swats with my hand, and then we’d assess the damage, and decide whether to continue. I don’t know what came over me, but some primal urge had taken control, I laid them on much harder than I intended, alternating left and right, and sometimes right in the middle. Her bottom was totally crimson, and was starting to blister in places. She was in a full cry, hiccups, tears, and begging me to stop, but no safe word.

Sometimes between spanks, I’d just rest my hand on her ass, or even dip into the valley between her legs. She was soaked; my pants had a huge wet spot where he pussy was resting on my leg. I was really getting into the whole thing now, and the last five came pretty quickly, and were the hardest yet. She was crying to beat the band when I finished. Even if she wanted to continue, I was convinced that we had to stop for now. I got some lotion, and spread it gently and lovingly on her ass. My right hand hurt like hell, so it was resting on her thigh while my left hand massaged the lotion into her fanny. She was still crying, but as I continued with the butt massage, her legs began to spread apart.

Even though we had agreed that we wouldn’t do anything sexual, this was too good of an invitation to pass up. With my right hand, I worked my way up her leg, and into pussy, while with my left hand, I gently caressed her ass. She was sopping wet, and was really wiggling around. As far as I knew, she was still a virgin,, so as much as I wanted to, I didn’t put my finger in her vagina, but I did spend a lot of time on her clit.