Chapter 9 -
We took off to the mall, where I had her buy three pairs of thong panties and a sheer body stocking (with open crotch) at Victoria’s Secret. I also bought her a pair of hot shorts and a tight lycra micro mini skirt at another shop. I didn’t want to see any of the stuff on, now. I wanted it modeled for me at home.
We came home and I sent her upstairs to change. I told her “Thong panties, hot shorts, and the shortest, tightest top you’ve got. Nothing else.”
I waited fifteen minutes, then shouted upstairs, “I’m waiting. You’d better get your hot little body down here ASAP.”
Fifteen minutes later, she still wasn’t back downstairs. I shouted up again: “I’m coming up to get you in five minutes. You’d better have your tight little ass down here before then or it won’t go easy for you.”
Four minutes, thirty seconds later, I heard her coming hesitantly down the stairs. She was barefoot, as instructed, wearing the tight hot shorts she was supposed to have on, and wore a short half-tee shirt. It wasn’t tight, but what it lacked in tightness it made up in looseness. It was one she’d cut years ago, when she was much smaller. I’m sure back then it probably barely revealed her navel. Now it barely covered her nipples. To the extent they existed, you could see the underside of her tits below the bottom of the shirt.
When I looked at her face, it was obvious that she’d spent most of the time upstairs crying. Her eyes were red and slightly puffy, but I didn’t care at all.
When she finally stood before me, I took in her body from bottom to top. My eyes traveled up her slim legs, over her lovely calves, and her bare thighs, to the line where the shorts were digging into her skin at her crotch. There was barely any ‘leg’ to these shorts. They were practically another pair of panties. I thought I could barely make out the line of her panties underneath the shorts from the front. That meant they had to be damn tight indeed. The tops of the shorts ended just above where I knew her pussy hair to end, leaving an expanse of an inch and a half or two inches below her belly button. All that space was bare up to her tits, where her tee-shirt ended.
Now that she was standing right in front of me, and because I was sitting down while she was still standing, I could actually see up her shirt and see her nipples. They were already hard and, when I told her to start pinching them, they quickly got as hard as they could. While she was pinching them I had her turn around. Again I looked over her lovely calves, thighs and ass. The shorts were tight enough that they still left a tiny space at the top of her thighs, just below her ass and pussy. I could see through that small space to the front of the room. When I slipped a finger into that space, up against her pussy, she flinched and jumped away.
“Sorry,” she muttered, as she stepped back into place without being told. “You scared me a little.”
I continues my inspection up her ass, past the top of her shorts where the end of the crack of her ass could just barely be made out. Her back, just like the rest of her body was fantastic. My sister was a tight little package, alright.
I could just make out the lines of the thong panties that I’d told her to wear. You could see the lines at the top, but as they descended into the crack of her ass, they disappeared. Perfect.
I reached forward and felt up her hips and upper thighs from the outside. I told her to turn around as I had my hands on her hips. I loved the feeling of her body rotating under my hands as her ass and pussy slid by them. “Alright, you can stop pinching your nipples. Reach one hand down your shorts and start playing with your clit.”
I saw tears start to form in her eyes as her hands dropped from her tits. “Can’t we even go up to the bedroom?”
“In a sec,” I told her. “Just do what I tell you to do in the meantime.”
She slowly slid one hand under her shorts and started fondling her clit. The shorts were so tight, I could see her hand perfectly as it did its happy work. I still had my hands on her hips, and I told her to turn around again, to face away from me.
“O.K. Now don’t stop playing with yourself. With your other hand, I want you to reach down the back of your shorts and slide one finger up your ass hole.” As I was telling her that, I moved one hand from her hips over her ass so I could rest a finger along the crack of her ass, over the shorts.
Jenny shook her head and muttered something about “I can’t, I can’t do that.”
“Sure you can, Jenny. Lube your finger up with your spit first, then just slip it up your ass. You had fingers up the ass last night, so this’ll be no different.”
I saw her other arm move forward in front of her and I assumed she was sucking on her finger, as instructed. Her hand came back behind her body slowly. She rested her hand at the top of her shorts for a second or two, obviously trying to prepare herself mentally. I helped her along by pulling the top of the shorts away from her body with my free hand. After I had made a little space there (which, incidentally, revealed the lovely curve of her bare ass at the top of her crack) she moved her hand down her shorts. I could see and feel, with the hand that covered her ass, her hand as it descended down her crack from inside her shorts. I felt her finger move along her crack until she got to her ass hole. She hesitated for a few moments, then slowly started to push it in. I watched her body stiffen as her finger went up her butt. I could feel her hand continue to move down her ass as she pushed her middle finger further and further into herself, wriggling it back and forth to get it in further. Under the tight, lycra shorts, I felt her first knuckle go past the tip of my finger, into her ass. She stopped when she had her finger about half-way in. I waited for her to collect herself for a minute, then asked her why she had stopped.
“Isn’t this far enough?”
“No,” I told her. “I want to feel your finger go in as far as it can. Don’t stop until your palm is all the way up against your ass hole.”
She nodded and lowered her head. Then she shifted her weight and spread her feet apart slightly and started pushing again. I felt the second knuckle on her middle finger sliding past the tip of my finger, into her ass hole. I also noticed that the tips of her first and fourth finger were now making their way out past the bottom of the shorts. Finally, her finger was all the way in and you could see her nails sticking out her shorts from the bottom. I started massaging her bottom with both hands now, occasionally putting pressure on the finger that was up her butt and forcing it a little further in. I also told her to move her finger around insider her rectum.
“How does that feel?” I asked.
“It’s O.K., I guess.” Her words were non-committal, but her voice betrayed some emotion. She was starting to get turned on!
“Keep massaging your clit from the front,” I told her, as I continued to knead her ass through her shorts. I also slipped one finger along her crack, underneath her ass hole, and tried to pressure her pussy through her shorts.
After a few seconds of this, I decided it was time for me to have some fun. I stripped out of my clothes while I watched and made sure Jenny didn’t stop her work. Very quickly, I was naked. My cock was as hard as it was last night. I knelt down behind Jenny and grabbed the waistband of her shorts on both sides of her hips. The waistband was already stretched since Jenny had both her hands down her shorts, and when I pulled at the sides, it dug into the back of the hand that was fingering her ass. I pulled her shorts down past her hand to just below the level of her pussy. She had her legs spread slightly so I couldn’t pull it down any further, but I didn’t need to. I had managed to leave her panties still on, but they didn’t cover anything in back. Her hand had actually been outside her panties when it was down her shorts, and she had just pushed the thong to one side when she pushed her finger up her ass.
I came around to look her over from the front. Sure enough, she was getting turned on. She had her eyes closed and she was playing with her clit madly. She’d work on it for a few seconds, then stop for a few, then continue. She had managed to get this hand down the front of her panties. I pulled her panties down from the front to take a look at her beautiful pussy. Unfortunately, I couldn’t get the waistband past the finger that was up her ass, since her hand had started outside her panties.
As I pulled her panties down, she opened her eyes and looked down at me. “Please Dave, f-f-f-f-f-fuck me. Please put it in me. I’m ready. Please.”
I went ‘round behind her again and tried to pull her panties off again from behind. There was no way to do it unless I tore them or she pulled her finger out of her ass. “All right. Pull your finger out.” She gave a big sigh of relief as she pulled her finger out. I pulled her panties past her ass and down to her shorts, then I picked her up and carried her over to the dining room table. She used her free hand to hold herself up against the table and I ran back and grabbed a cushion from the couch. I had her rest her body against the cushion and lean forward over the table.
“OK. Keep playing with your clit and put that finger up your ass again.”
“David? Do I have to? Can’t you just ... put it in me? I’m ready, ... I promise.”
“I don’t think you’re quite ready, and it turns me on to see you fingering yourself. ... Go on, do it!”
She was leaning over the table at an angle already, so she could finger her clit with the left hand. With the other, she slowly reached back and put her finger on her ass hole. She’d touch it with the tip of her finger for a bit, then put pressure on it slowly. I could watch as her ass hole started to open, then her nail would come up against her sphincter and she’d stop and pull back again. After two or three times this way, she tried bending her finger a bit and coming in nail first. She put her fingernail tip against her ass hole, then let it slide in till her fingertip was going in. She got to the first knuckle this way, then she stopped. “David. Please just ... you know. I don’t want to do this part. My ... pussy ... is ready.”
Poor girl. She didn’t even realize that I intended to fuck her up the ass. “Just keep going. I like to see it. When you get your finger all the way up your ass, I’ll start fucking you.”
After I said this, she put her face back down on the table and forced her finger further up her ass. Even though it’d just come out of there, it still took her a full minute to get it all the way in. Finally, it was in. Her other fingers were splayed out over her ass while her other hand was working her clit below her pussy.
I came up behind her and pushed her shorts and panties down as far as they would go to give myself more room. I pointed my cock at her pussy and slowly slid it in. I didn’t pump or do anything else, just pushed it up her cunt slowly and steadily. I could feel her fingers working her clit against the underside of my cock as it went into her, plus I could feel the finger that was up her ass over the top of my cock through the membrane separating her ass and pussy.
Once I was fully buried in her, I told Jenny to finger fuck herself up the ass. “I want to be able to feel your finger sliding in and out of your ass with my dick.” Jenny didn’t have much room to maneuver, but she managed to slide her finger in and out a few times. I slid my cock in and out a little bit at the same time to try and get as much lubrication as I could.
Finally, I reached down and pulled her finger out of her ass manually. As I was pulling her hand with my own, she said “Ohhhhh. Thank you, David. I’m starting to feel sore down there.”
“I spat on my hand and rubbed the spit around her ass hole. At the same time I pulled my cock out from her cunt and pointed the head at her sphincter. “You’re about to feel a whole lot sorer, Jenny.” Then, with one hand I guided my cock to her ass hole and with the other I held her body down against the table.
When Jenny felt the head of my cock against her ass hole, she started to squirm. “My God, David. What are you doing? NO! You can’t put that there.” Now she was trying to twist out from under me. “STOP!! PLEASE, David, STOP. Oh God. Please stop. ... Don’t put it up there! Please!”
I let go of my cock for a second and slapped her hard on the ass. “Quit squirmin’ around, sis. I fucked your cunt last night. What made you think I’d be satisfied with that this morning? I told you last night that I’d take every one of your holes. Day two... hole two. Now quit moving around.” I still held her down with my weight pressing her against the table. She wasn’t in much of a position to get away anyway, so I continued: “Look, sis. You’re going to give this up to me one way or another or all those pictures are going to haunt you for the rest of your life. You’ll be plastered all over Playboy, Penthouse, Hustler and any other magazine that’s willing to pay me for them.” I gave that a second to sink in. “Now you don’t want that, do you?!”
I went on as I put my hand back on my cock and held it against her ass hole and started to push. “Now, if you relax and don’t move around much, this’ll go easy for you. Just relax and let me do the work. Relax your ass hole.” As I was saying this, the head of my cock slipped past her sphincter, and into her ass. “There we go. The first part’s over. Now that wasn’t so bad, was it?” I looked up Jenny’s body and saw that she was now crying. I let go of her with my other hand and kept pressing forward. Every inch my dick slipped up her ass brought fresh sobs from my sister. Finally I was all the way in.
“C’mon, sis. Quit crying. It’s not so bad, is it?”
I pulled her up off the table so she could lean forward on her hands. “Is it that bad?”
She shook her head and tried to stop crying.
“Can you feel it up your ass?” I knew that was a dumb question, but I wanted her to acknowledge the fact that she was being butt-fucked.
“Of course. Oh my god, it hurts.”
“C’mon. It can’t hurt that bad. Just relax.”
“I’m relaxing! ... It just hurts.”
“Lift your arms over your head.”
When Jenny did so, I grabbed her shirt and pulled it up over her head and threw it to one side. Now all Jenny had on were the shorts and panties that were pushed down to her hips. Other than that, she was naked. I pulled her body back to mine and lifted her up in the air. With my cock still up her ass, I carried her over to the mirror in the hallway. I leaned back against the arm of the couch and rested her on my lap (sort of). I still had to hold her in the air, though, since she was so much shorter than I was. Her ass was squeezing the shit out of my cock now. I told her to lift her legs in the air toward her body. I guess being a cheerleader has some unexpected advantages. I could never have pulled my legs all the way up in the air like she did, but there they came, her knees coming closer and closer to her shoulders.
“Pull your fuckin’ shorts and panties off. They’re killing my dick.”
Jenny reached down and pulled her shorts (and panties) up her legs, past her knees and almost to her ankles. She couldn’t reach any further and couldn’t get them off totally.
“Allright. Spread your knees to keep ‘em up there.”
Jenny continued to do as instructed. Both of us could look through her legs at the mirror. I was leaning back and half-resting her body on mine. With her legs in the air, tied at the ankles, and her knees spread, we both had a perfect view of her slit and my cock halfway up her ass. I couldn’t get it any further in in this position, but if I had, I’m sure I would have broken it. I moved one hand to hold onto her left leg and keep it in the air. My other hand was wrapped around her body, just below her tits.
“Play with yourself, sis. Play with your clit and pussy hole.” She leaned forward to reach both hands between her legs and that blocked my view. “Hey! You’re blocking me. Lean back again.”
“I can’t reach both hands and lean back at the same time! What do you want me to do?!”
“Lean back. Just play with your clit.”
I watched her fingers working her clit over and could see she was starting to get excited again. I tried to slide my cock in and out of her ass hole, but I couldn’t get almost any motion. I did get a little friction and it felt great. Watching myself fuck her ass in the mirror and watching her play with herself was a fucking turn-on. After she was a little more turned on, I told her to finger herself in the pussy again. She moved her hand down from her clit and slipped one finger up her pussy. In the position that she was in, her pussy hole opened up like a flower to accept her finger. She was really getting turned on now, and so was I. With my right hand I started to fondle her left tit and nipple as best I could. Even though I wasn’t moving in and out of her at all, I got so turned on just watching her finger herself and looking at my cock up her ass hole that I started to come right then.
“Fuck!! That feels so fucking good.” I squirted load after load up her ass. Now Jenny started to come too. She kept finger fucking herself as she shuddered and came. Finally, she just grabbed her pussy and held on. I’d already finished coming up her ass and I pulled my dick out as it softened.
“That was so good, Jen. You’ve got a perfect ass hole. I can’t wait to fuck it again.”
As I said that, I put lowered her to the floor and let her collapse there. I was surprised to see her start to cry as she lay there.
“Thanks, sis. That was great.”
As she lay on the floor, she curled her body up into a fetal position and continued to cry. “What are you doing to me?... I can’t believe that I came just now. You were hurting me! That really hurt! You made me get turned on.” She was still sniffling, but now she started to uncurl. “Why are you doing this to me? Do you hate me?”
I sat down next to her and held her body to mine. I gave her a tight hug, then backed off a bit and kissed her deeply. I kissed her for ten or twenty seconds but didn’t get much of a response. Finally, I broke the kiss, but still held her body in my arms. I looked her in the eyes and tried to sound as sincere as I could. “I love you, Jenny. I love you like a sister and I love your body. I’d never do anything to really hurt you and I’ll protect you from anyone who tries. But I know that this is what you need and what you want. You may complain about it, but we both know that you came just now as big a come as you’ve ever had. So don’t complain to me about what I’m making you do. You needed your cherries popped as bad as any girl ever did, and so did Erin and so did Carla. You loved last night and you loved this morning, even though you’re crying about it now.”