Sex Between SiblingsbyJANAMARIE©
"Janet, I think this is going to hurt a lot. Will you stop if I tell you to?"
"Oh yes love. I will stop if you even breathe the word. But first I am going to loosen you up a little before putting this thing up your ass."
I then lubed up my fingers and told her to lift her ass in the air. She did and I started to rub my fingers around the rim and then inserted one and then two. The same as I did when I was eating her. I kept them busy for a while before having my third finger join them.
"Janet, your fingers are starting to hurt me and they are a lot smaller than the dildo you just bought."
"Not really Glor. My fingers, even though each one of them is smaller, together they are a lot thicker than the dildo."
"OK honey, I am going to slip the dildo up your ass. Hold your hips in the air and I will go in very gently."
I lined up the little head on the anal wand and put it against the ruby lips of her tight little asshole. I put the slightest pressure on it and it slipped in an inch or so. I was looking down at her and didn't see any pain on her face so I pushed a little more. She was scrunching her mouth around as if it was hurting her but not saying a word. I pushed a little more and I could begin to see pain showing on her face. By then I had three inches or so buried. I stopped for a minute and leaned forward to let my fingers wander over her nipples. She looked up at me and smiled,
"You know I love that don't you Sis?"
She had never called me 'Sis' before and it sort of surprised me. "Yes, love I do."
I then pushed a little more and now had four inches in her and by now she was crying.
"Do you want me to stop?"
"No, try and get it all in me so I want to know what it feels like."
I gave the final push and then had the entire five inches or so buried deeply in her virgin ass.
She was gritting her teeth with pain but holding it in very well.
I started the same kind of thrust and pull back movement I had been using with the big dildo on her pussy and it didn't take long before she was shouting,
"STOP…take it out. I will NEVER let anyone do that to me again. It hurts too fucking much" WOW, that was the first time I ever her heard her use the 'F' word. She must really be serious about this.
"Glor let's shower and get cleaned up."
We did and afterwards I suggested she go out to the kitchen and make us some lunch while I was tidying up.
She had soup and sandwich meet and some soft rolls on the kitchen table by the time I got back out there. We had our lunch and I told her I was going to my favorite little fish market later and would get some crab cakes for a dinner I would throw for her and Jim sometime in the next couple of days. She thought that was a great idea and I knew if I ever wanted to get my hands on that huge dick she said he had I would have to start somewhere getting closer to him.
The dinner went off fine. Jim loved the crab cakes and I had accompanied them with asparagus and a salad. A small dish of vanilla ice cream finished off the meal. Jim had a nerdish personality but I chalked that up to the age difference between us. After dinner I suggested a game or two of Scrabble and he jumped at the chance.
Glor just rolled her eyes saying, "You are playing right up his alley. He is superb at the game."
Sure enough her won the two games by a wide margin and was in his glory. We sat around chatting for the next hour or so and then they were gushing with appreciation for a nice night. NO problem, it was but the first step in my effort to get the kid's dick.
The next couple of weeks went by with only a couple of brief get-togethers and I decided to fire another salvo. I phoned their cell phone and Jim answered. I told him I was going to have a repeat of my crab cake dinner the next night and wanted to invite him and Glor. It sounded as if her jumped thru the phone accepting the invitation.
A got a couple of bottles of Chardonnay to accompany the crab cakes and the dinner went great. Glor and I told him that we had let him win the last games of Scrabble and if he wanted to try again we were prepared to kick his butt. Well, the male ego couldn't stand that challenge and out came the board. Sure enough Glor won the first game and I the second. He was crestfallen but we never mentioned until later that I had kept his glass full of the Chardonnay and he was more than a little tipsy when we were playing. He took our deception in good nature and we played some card games until it was time for them to leave.
A week later I knew Glor was going to go out of state overnight with her college choir leaving Jim home alone. That evening I phoned him saying that I was having some trouble with my VCR and asked if he knew anything about them. He assured me he did and would be right over. I had jerked around on the little connection cord that goes between the VCR and the TV to the point it was disconnected inside the fitting.
Jim came over with a little tool pouch prepared for a major operation on my patient. I made certain I was wearing a very loose fitting blouse without a bra and just had to lean over the unit while he was working on it to make sure he saw what lay beneath my top. Within ten minutes he had found the problem and had the coupling connection repaired. I said I wanted to try it before he got away.
A bombshell of a porn tape was innocently sitting inside the unit just waiting it's turn. Jim turned it on and gulped when he saw a guy fucking a gal on her hands and knees while she was giving another guy laying underneath her face a blowjob. I had walked out of the room about the time he turned it on. I didn't want to be right there and be in a position of having to get up and turn it off in the event he was embarrassed so I waited in the kitchen for a bit and returned to find Jim glued to the screen.
"Damn, that looks like fun. I forgot I had that tape in the unit" I said
He never said a word but kept staring at the screen. I could see that he was getting a little uncomfortable with the expansion taking place in his pants. It wasn't long before he had to sit back and reach in his crotch to reposition himself.
By then the gal on the screen was sitting on the dick of one of the guys while she was jacking off the other. Poor Jim didn't stand a chance. He was moaning as loud as Glor does.
"Jim, why don't you open your pants and let your wand out for some fresh air. It looks as if it is kind of cramped in there." At the same time I was saying that I had reached between his legs and opened the top button on his jeans. He wasn't wearing a belt and the button popped open with the pressure being put on it from the inside. I then let my hand pull down the tab on his zipper.
Good Lord, Glor was right. This guy had a dick to end all dicks. With all of his earlier repositioning himself it was sticking right through the slit in his boxer shorts. The damn thing had to be over ten inches and was damn near the thickness of my wrist. It was hard as a rock with just a bit of pre cum showing on the head of it. He could do some serious damage to a woman with this thing if he wasn't careful.
I let my hand slide over it and gently started to slide it up and down. With my other hand I pulled my blouse all the way open and let my tits burst out. I reached over and put a hand behind his head and turned it from watching the tape and directed his face at my chest. He dropped his face between my tits and started to kiss the nipples back and forth. While he was enjoying my tits I was jacking him off ever so slowly. There was a little more pre-cum showing now and I took my fingers and worked it over the head of his cock and all around the cock rim and then down the sides of his shaft. I was positioning my hand along the shaft to see if I could some accurate idea of just how big he is. It was apparent I could get a t least three handfuls before reaching the head of it. He slid forward on the sofa so his ass was hanging free and that allowed his dick a little more freedom to stand almost completely erect.
He was breathing much faster now and I could feel him trembling through his mouth on my tits and my hand on his cock. He then started a deep moan and his cock started to twitch. By now he was gasping and his breathing was labored. I could feel something starting way deep in his balls and a second later his orgasm began. I swear the cum shot out of his cock at least six inches in the air and it kept on exploding time after time. He must have shot four or five thick heavy streams out of that monster. I kept jerking and milked every drop he had. I got up very slowly and retrieved a warm wet towel from the kitchen.
I returned to the living room and he was still lying exactly as I left him. I had removed my top and shorts and leaned over and put the warm cloth on top of his dick. His eyes sprang open and I leaned forward and straddled his face with my tits. He reached up and put a hand on the sides of them and buried his face in between them while pushing his hands together. I reached down and gently wiped up his cum that had shot all over his stomach. I then sat on his soft dick and kissed him very softly.
"You are some lover Jim." I purred. He hadn't done anything but lay there and let me jack him off but I wanted to stroke his male ego a bit.
I then slid down and just flicked his shaft with my tongue and gently held his huge balls in my hand. God they were the size of tennis balls. It didn't take much work on the part of my tongue before his young shaft started to expand. I pulled it away from his abdomen and softly took the head of it between my lips. I wasn't sure that I would be able to get the whole head of it in my mouth when it was fully hard but I was damn sure going to try. My free hand was gently tracing the veins in his shaft and I could feel than when I let my fingernails do the tracing it seemed to turn him on more.
It wasn't long before that marvelous piece of meat was at full attention. I was right, I could barely get the entire head of it in my mouth. He had one humongous cock. I was glad that I had had my tubes tied after the birth of my daughter for I wasn't sure they made condoms for a cock of this size. I put one knee on either side of him and positioned his cock in line with my pussy. I knew I had better be careful or he would impale me on the thing.
He looked up at me and said, "Janet, I don't think we should be doing this. I am a virgin, you are my sister and I don't really know what to do."
Well, I'll be, another virgin…two in less than a month. That has to be some kind of record.
"Don't worry about it Jim, I will be happy to teach you all you need to know."
I then started my slide down his pole. I was soaked from the passion I had while jacking him off and my pussy lips were trembling. I was able to get about six inches in me without any trouble when I could feel the tightening of my vaginal muscles around the head of it. I could actually feel the ring around the head of his cock with my vaginal muscles. There was no pain so I kept going. I was sitting straight up and he had reached up and was playing with my tits.
"Damn Jim, that feels good." I said "Now hold still while I try and get the rest of you in me."
I pumped up and down a bit getting it in a little further with each of my downward strokes. I still only, ONLY!, had about eight inches in with a lot more to go. I slowed a bit and then resumed my efforts.
I had stopped at the eight-inch level and then just put a slow but steady pressure on it and I soon had his cock buried to the hilt. Holy shit, I thought I could feel it all the way up to my throat.
I looked down at him saying,
"Jim, you are all the way inside of me now. I am going to rise up and down but I don't want you to rise up hard trying to jam it into me. You could do some serious damage to me if you do. OK?"
"OK Janet. Whatever you say. I don't know anything about this other than what I have read about and seen on those porn flicks."
"Trust me Jim. You will know everything you need to know when we get through today."
I then started a very slow rocking on it and lifting myself off him a few inches before coming back down. It felt sensational. I leaned forward and once again had my tits straddling his face. He seemed to love nuzzling them. At the bottom of my thrusts I started to swish my cunt all around the base of his shaft and his balls. That got his attention big time.
I had reached around behind my ass and was gently playing with his ball sack to hear "God, Janet, that feels great." He shouted.
I then started to lift myself up about six inches before falling back down on his lovely shaft and found I could handle that without any trouble. That was all I needed to know. I started to pump that cock into me fast and furious. I don't think I ever rose so that less than three inches was still buried in me and when I came down I kept up the squishing of my cunt. My clit was completely aroused and was receiving the benefit of my squishing when I was at the bottom of my stroke.
"Jim. It's my turn to cum and I am going to do it nooooowwwwww"
My pussy actually went into what I can only describe as convulsions. My vaginal muscles were expanding and contracting like I had never felt before and there was a warm glow extending throughout my whole body. I am 32 and have had sex numerous times but never ever felt anything like this in my life. He wasn't far behind me. I could feel the pulsing in the shaft and he was soon shooting stream after stream deep inside of me. I didn't think he would be recharged so quickly for he had just cum a half-hour earlier when I was jacking him off but I guess I forgot the sexiness of youth.
I just collapsed on him and with the length of his cock it stayed in me as compared to what a shorter cock would have done. We were both exhausted. Me, more than him but we lay like that for a good while before I got up and off of him.
"Did you enjoy that Jim?" I asked.
"God, yes. I have jacked off a thousand times but it never felt like it did when I was doing it to you." He responded.
"I'm happy for you. That cock of yours was made to give women pleasure but you could really do serious damage to a woman's insides if you aren't somewhat gentle. I'll teach you how to use it. OK?"
"That would be great Janet. All I know how to do is to jack off and even there you made me cum a lot more than I ever do when I do myself." He volunteered.
"OK tiger. Say I have to run out to a business meeting for a little while. How about I give you a call when return if it isn't too late?"
"Sure, I have a paper I'm writing that I can work on."
I was back from me meeting around nine and all I could think of during that whole damn meeting was the lovely cock on the boy. I called him as soon as I was in my door inviting him over. He said he would be there in about twenty minutes.
I answered his bell absolutely nude and his eyes almost popped out of their sockets when he got a full frontal look at me.
"Come on in big boy." I purred as seductively as I could without making it sound too contrived.
He followed me like a sheep and I led him straight to the bedroom.
"Strip down Jim. I have some lessons for you."
It couldn't have taken him a minute before his clothes were off and he was lying on his back on the bed.
"Wow, you're anxious.
I looked down and his cock was just starting to rise in anticipation of what was ahead.
"Jim, I'll be right back." I ran to guest bedroom and went to my sewing basket and retrieved my cloth bound measuring tape. I wanted to see just how big that damn this was.
By the time I returned it was at its full glory and he was stroking it lightly.
"What, are you trying to do, start without me?" I asked jokingly.
He blushed and said "No, I just wanted to keep it warm for you."
"Touché. Great response"
"Lie back and let me do something". I placed the end of the tape at the base of his cock where it joined his stomach and ran the tape to the very tip. My God, it was just a bit over ten inches. No wonder it felt as if it was all the way up to my throat when he was fucking me.
I threw the tape on the floor and leaned over him with my tits hanging right in front of his mouth and said "Gently tiger."
I lowered my head to his crotch to see if I could do that cock any good with my mouth. As hard as I tried I couldn't get much more than the head of his cock in my mouth. My lips were wrapped around the head of it just past his cock ring and that was it. Every time I tried to get more in my mouth my teeth were scraping his shaft. How the hell was I going to give him a blowjob?
I figured the only way was sort of cheating. I would get the head of his cock in my mouth as far as I could and then grab the shaft with one hand right up close to the head. I would move my hand up and down on his shaft as if it was my mouth moving like that all the while I would be licking my tongue around the head of it. I would really be jacking him off with the head of his cock in my mouth. The saliva coming out of my mouth provided all the lubrication my hand needed and it worked just fine. I had the other hand cradling his balls as gently as I could while massaging them with my fingers.
I had my head twisting from side to side the way I would be doing if I were able to ride his shaft from the top to the bottom. It wasn't long before I could feel his muscles twitching and he had wrapped his fingers in and around my hair and was pulling me down on him. He was ready…It had worked. A minute or so later I could feel the first of his love juices hitting the back of my throat that were followed but three or four more.
He didn't disappoint me. His tongue lightly brushed my nipples and his hands gently stroked them. I reached down and started to stroke that magnificent cock a little more roughly than he was touching me. I couldn't control myself. Here I was, years older than this young stud and I couldn't keep my hands off that wonderful piece of meat. I leaned over and fell alongside of him on the bed and told him that I wanted him to fuck me in what is referred to as the 'missionary position.'
I first reached over to the bedside table and got my tube of KY jelly out and smeared his cock with it. I also took a glob and pushed it into my pussy. I then lay back and pulled him on top of me and lined his cock up with my pussy.
"Now Jim, I want you to gently, hear me, gently, push the head of your cock into me. Not far, just a couple of inches." I instructed.
He did exactly as I said and I pulled his face down and buried my tongue in his mouth.
I started to throw my pussy up to take more of his cock and it wasn't long before I had more than half of it in.
"Jim, I now want you to keep up a little pressure on your hips pushing your cock in me further but I want you do it very s l o w l y. Do you understand me?"
He nodded yes and I could feel that thing penetrating me to my very core. He did exactly as I had asked and he soon had it buried.
Whew, it felt wonderful.
"Jim. I am going to wrap my legs around your back and pull you into me whenever I think I am able to stand it but I do NOT want you to go ramming it into me. Understand?"
We then started a very slow and magnificent fuck. He thrust deep and slow and I found myself pulling him deeper than his eleven inches would allow. It was fantastic. I could soon feel the pulsing in his shaft and his breathing becoming faster with each thrust. Mine was almost the same.
It wasn't long before we were both exploding and my worst fears came true. From the very beginning I was frightened he would go crazy ramming it home when he was in the throes of passion of an orgasm and that is exactly what happened. He backed off until just the head of it was in me and than thrust it in with one long hard move. I screamed as if I had been shot and he fell off me. I was doubled up with pain and he was off the bed and running around the bedroom asking what he could do for me and I just said,