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 reach 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.
Eventually, my left hand wandered into her ass crack, and started to massage her anus, while my right hand continued to masturbate her. She had told me that she was into pain, and inserting things in her ass hurt like hell, but she liked it, so without a lot of preparation, I jabbed a finger into her ass. When I did, she actually screamed.
When I started sawing back and forth, she was moaning, squirming, and I could barely hold her in my lap. I'm not absolutely certain, but I believe that she was having orgasm after orgasm. I was so off in my own world that it didn't register the first time that she said 'rex', probably not the second either. Eventually, she screamed rex loud enough, and got my attention.
She fell to the floor in what closely resembled a faint. I desperately wanted relief, but she was almost comatose, her ass was red and abused, and I wanted to be a gentleman. Correct that, I didn't want to be a gentleman, but I felt like I had to. I gathered her up, carried her to her room, and put her to bed.
I haven't controlled anything else since this whole thing started, so I'm not sure what made me think that I could control this. I asked Jeff to spank me, lightly, over my clothes, non-sexually, but just as soon as I lay over his lap, my motor started running. Instant turn on!
The first swat was so light as to be a joke, but then he really started, and it really hurt. I was almost jumping around in pain and pleasure. The two seemed to meet right in the center of my clit. He said that he gave me 25, but it could have been 125; I was too far gone to count or care.
We were both out of breath, me from excitement, and him from a combination of excitement and exhaustion. While we rested I saw that his hand was red and almost raw. I immediately felt sorry for him, and felt badly because it was me who caused it.
I also felt really guilty for leading him astray, and starting down this path. I decided that the only way to make it right was to escalate the spanking to the next level of pain. I suggested that he take my shorts off and spank my nearly bare bottom.
I was wearing pretty shear panties that would offer little or no protection. I was actually going to remove the shorts myself, but before I could, Jeff motioned me closer and did it for me. What an erotic feeling to know that my brother was taking my shorts off, and could see a pretty good outline of my pussy. Also, I could see his erection. Even better, I knew what was going to happen next.
Very carefully, I leaned over his lap, remember my ass was really sore. With his first spank, I was sure that I had let this go too far. The sting was worse than anything that I could remember feeling. It landed on my right cheek, and sent a jolt that went from the top of my head to my toes. However, right in the middle was a special spot; it went there also, and man did it feel good. I just wasn't certain that the pleasure was worth the pain. I didn't get a long time to ponder as the second spank landed a second or so later. Again, the pleasure was great, but the pain was almost unbearable.
I totally lost track of the number of swats, but at some point, Jeff stopped spanking me, and just started rubbing. I hadn't seemed like 25, but I assumed that he knew what he was doing. God the rubbing felt good. His hand was all over the place, and I just couldn't get enough. Some parts of my ass were on fire more than others, and I was wiggling my ass around to get his caresses on the right spots. I was having mixed feeling about the spanking being over because even though it was very painful, it also felt great.
Imagine my surprise when Jeff told me that I had 12 to go, and he started spanking again. Frankly, I wasn't sure that my ass could take 12 more. However, 12 spanks later, I would have done anything for this to continue. It seemed like I was having an orgasm with each spank.
I could tell that Jeff was tired, and he had a very obvious erection. I knew that he needed relief, but I wanted to up the ante, I wanted it all, I wanted to feel more of this delicious pain. As I often do when I'm excited, I let my alligator mouth overload my sparrow ass, and I told Jeff to strip me totally naked, and really beat me.
The look on his face when he was taking off what few garments remained, was priceless. When he pulled my panties down, the pain of the hem scraping over my ass, that delicious pain, was electric. I actually expected him to fondle or lick my titties when they came into view, and truthfully, he could have done anything, anything that he wanted, and I would have allowed it. However, he was a perfect gentleman, and he stuck to the task at hand.
I lay over his lap again, with my breasts resting squarely on his left leg, and my ass over his right. When he started spanking, I started squirming which caused the rough denim on his left leg to start scraping my breasts----God did that feel great. It hurt on my ultra-sensitive nipples, it hurt a lot, but I still loved it.
Even better, the mons of my bare pussy was scraping on his other leg. The deliciously painful friction in both places coupled with the sharp pain of the spanking had me in orgasmic bliss. The orgasms just ran together, and wouldn't stop. I was so exhausted that I'm not sure that I could have gotten out the safe word. Thankfully Jeff stopped on his own. I was, crying, snot running out of my nose, tears outlining my face, hiccuping, and totally inert.
Then Jeff did the most wonderful thing; he started rubbing lotion into my ass. As I gradually started to come around, I realized what a good view he had, but I wanted him to see more. I wanted him to look at my most private places. I needed for him to have an unfettered view. If I'd had the strength, I'd have reached back and pulled my cheeks apart so that he could see my anus also.
I imagined that I had an audience of more than one. What a turn on. I couldn't spread my cheeks, but I could spread my legs apart. I tried to do it slowly so as to not be obvious, but he probably knew that it was on purpose. He also knew that I was canceling our agreement to keep this non-sexual.
His fingers found their way into my sex, and with his other hand, a finger stuffed its way into my ass. Again with the pain, but what a great pain it was. He started sawing back and forth in the back, while rubbing my clit in the front. The pain gradually subsided, but not the orgasms, they just continued to build.
Every time that he pushed his finger it, it went right to my clit. This went on for several minutes, and I just couldn't take it any longer, so I called out "rex!" Nothing happened, he just kept going. I must have screamed 10 times, the last one loud enough to be heard next door before he actually stopped. I collapsed on the floor.
I woke up the next morning in my own bed---on my stomach of course. I love my brother!
I was lying there in a blissful state when my mother came in, before she left for work, to tell me that later in the evening, my cousins Rebecca and Peter would be coming late in the day to spend a couple of weeks. Some family problem that their parents had to take care of. I had been plotting something, and this news required that I put my plan into high gear.
TO BE CONTINUED
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