This is the story of how I finally got to fuck my sister-in-law, Cheryl.
For as long as I have known my wife, I have wanted to fuck her oldest sister, Cheryl. At the time this happened, she was 32 years old. She is tall (about 5’ 9”) and on the slender side with long beautiful legs and a great ass. But I am first and foremost a breast man and Cheryl has what always appeared to be the most incredible pair of tits. My wife, on the other hand, is pretty small – barely more than an “A” cup – so thoughts of feeling and fucking those huge tits of her sister’s constantly drives me crazy. Cheryl is a biker chick and she likes to wear things like tight blue jeans and little black tank tops with push-up bras that accentuate her 38DD rack (I saw the label on a bra in her bathroom once). She has long, dark hair and smooth ivory skin. I should also let you know that she loves to party and has the reputation of being something of a slut.
I had been with her sister for a few years at this time and had been fantasizing about her since the day I first laid eyes on her and those fantastic tits. When I was around her, I could barely keep my eyes off of her breasts and it just drove me crazy wanting to see them and touch them. I always tried to see down her shirt and when I was lucky enough to get a glimpse of that cleavage, I would just imagine being able to slide my cock between those huge, soft mounds, shooting cum all over them. But, even though she was kind of a slut, the sisters were really close and I just knew that there was no way I was ever going to be able to actually fuck her, so I was left with constantly masturbating to thoughts of her. I was able to get some pictures of her at a party when she was wearing a little top that showed some cleavage and also one of her in her swimsuit. I hid them out in the garage and would pull them out from time to time so I could look at her pictures while I jacked off. Of course, I would often fuck my wife while fantasizing about her sister, too.
There came a Saturday night when a bunch of us were checking out a band and partying at a bar that was only a couple of miles from Cheryl’s house. Everybody was getting wasted and the booze and drugs were flowing. My wife was drunk as hell, but Cheryl was really out of it. Her 14 year-old daughter was at a friend’s house so she could really cut loose. She had taken a couple of downers and had been drinking shots of Tequila and it caught up with her. It wasn’t too long before she was passing out, barely conscious, and needed to go home. My wife was pretty out of it at this point, too, but wanted to stay and party with her friends so I volunteered to take Cheryl home. It wasn’t until I got her into my car and she passed out completely that I started having thoughts.
It dawned on me that here I was, alone in the car with her and she was now passed out cold. She was wearing this tight little black silk shirt that buttoned down the front and I was sitting there staring at those huge tits with nobody else around. After a couple of minutes of thinking about it, I gingerly reached over, put my hand on her arm and gave her a little shake. When she didn’t respond, I started pressing against the side of her tit with the back of my hand and fingers, rubbing the side a little and pressing into that soft mound. She didn’t budge, so I let my hand slide up onto her tit and just sit there not moving – I was scared to death of her waking up and catching me. She still didn’t move so I started just gently massaging it, compressing her immense breast and feeling its softness. It felt amazing – so big and soft and full – that I moved my hand to her other tit and started squeezing that one as well. I knew what I was doing was probably wrong, but I was a little drunk, too, and couldn’t help myself. My cock was hard as a rock as I realized I was actually feeling those tits that I had spent so much time fantasizing about. I got a little bolder and unbuttoned a couple of her buttons to expose some cleavage. She was wearing a push-up bra as usual and the sight just about sent me over the edge. I slid my hand down between her tits and started to gently massage her left one – damn, I almost came right there. By this time, I was almost to her house so I just continued to gently feel her up until I got her home.
When I got her out of the car, I realized just how out of it she was. Downers and tequila had sedated her to the point where I actually had to carry her into the house. I was crazy horny by now and really wanted to at least see those tits and the rest of her beautiful body since I figured that this was my one and only chance. I decided I would take her to her room and if she didn’t wake up, undress her and put her in bed. She was completely unconscious at this point and my plan was to look at her naked body, feel her up some more and jack off over her in person – she would never know. That plan didn’t last for long, though.
I carried her in and laid her on the bed and unbuttoned her shirt. The sight of those 38DD tits squeezed together in a thin black push-up bra was something I will never forget. I finished taking her shirt off and then took off my pants so I could stroke my raging hard cock while I sat on the bed next to her and squeezed her tits through her bra until I just couldn’t take it anymore. I reached underneath her, unhooked the strap and let them out. They were the biggest, most beautiful tits I had ever seen in my life! They were huge and full, creamy white in color with light tan aureoles the size of a half dollar. Cheryl’s breasts were even more beautiful that I had imagined in my wildest jack off sessions. I took them both in my hands and started massaging them harder and harder, shaking and jiggling them and worshipping them in every way. I lowered my head and sucked on them, moving my mouth from one huge breast mound to the other and even though she was totally unconscious and not moving, I felt her nipples respond and grow hard between my lips. I thought, “what the hell,” and straddled her, careful to keep my weight off of her while I squeezed those big, beautiful tits around my cock, slowly sliding it in and out between them. I couldn’t believe that I was actually tit-fucking Cheryl as I had imagined so many times! I stood up again and moved toward her head. There she was with that beautiful face and sensuous mouth; I just had to put my cock in there. I turned her head toward me and stuck my huge engorged cock between those sweet lips. She didn’t move so I slowly and gently fucked her in the mouth, only putting in about three inches or so, until I was so close to coming that I could barely stop myself in time.
At this point, I was going crazy with lust. My cock was as big and hard as it had ever been and here I was, alone with my sexy sister-in-law, the object of I don’t know how many jack off and fantasy sessions, and she was completely passed out on downers and booze. I could do whatever I wanted with her and to her.
I sat back down on the bed next to her and slowly undid her blue jeans. I stuck my hand down between her legs and started rubbing that sweet pussy that until now I had only been able to dream about. I was sitting on the edge of the bed fondling her breasts with my left hand and rubbing her pussy with my right. It looked like I was finally going to fuck my sister-in-law and I was in heaven! I slid two fingers into that tight cunt and started finger-fucking her for all I was worth. I worked my fingers in and out of her wet twat and imagined my hard cock sliding inside her. I rolled her over flat on her stomach and pulled her pants and panties completely off of her, removing her little high heels at the same time and throwing all her clothes in the corner of the bedroom. She was lying face down now, completely naked with her legs slightly spread, and I just stood there for a minute, slowly stroking my cock while I looked down at that sweet body that was all mine for the taking. I returned to the bed and started massaging and feeling her firm, round ass with both hands. I slid my right hand back down between her legs and finger-fucked her pussy some more while I tonguing her sweet little asshole. I couldn’t believe the sensation of my hand between her legs from behind working over that pussy, and my face buried in her beautiful, round ass. When her asshole was good and wet with saliva and my fingers were wet with her cunt juice, I slid the middle one into her asshole and started finger-fucking her tight ass. I worked my finger in and out of her ass, loosening up her hole while I reached underneath her again with my left hand and continued squeezing one of those big, beautiful tits.
I knew now, for sure, that she was not going to wake up until the next day when the drugs and alcohol wore off so I could satisfy my deepest desires. I spread her legs wide open and took a long look at that beautiful pussy and ass. Yes, it was really going to happen. I got between her legs from behind and slowly slid my cock into her waiting pussy. It felt so good, I couldn’t believe it, but I was not going to finish there. After a few strokes to get it good and wet with cunt juice, I pulled my cock out of her and started slowly pushing the head against her asshole. There was a little resistance at first and then the head of my cock slipped into her delicious ass. She moved just a bit and let out a little sound and my heart almost stopped. But then, she was still once again and I slowly worked the rest of my rock hard cock into her ass, pushing it slowly in and out, a little deeper each time, until I was bumping right up against those firm ass cheeks. I slowly moved my cock in and out of her tight ass until it relaxed completely and then started fucking that ass for all I was worth. I let my total body weight down on her and reached under her and grabbed both of her huge tits while I pushed my cock in and out of her tight ass. I was actually fucking my beautiful sister-in-law in the ass while squeezing the most beautiful pair of breasts I had ever seen. I continued sliding my cock in and out of that tight ass, living every fantasy I had of her, and it wasn’t long before I couldn’t hold it back any longer. I exploded again and again, shooting loads of my hot cum into her, filling her beautiful ass while I squeezed her immense tits as hard as I could.
When I finally got my breath back, I got up, went in the bathroom and washed off. I put my pants and boots back on and returned to the bedroom to tuck her in before I left. When I rolled her onto her side and went to pull the covers up over her, I got another look at those incredible breasts that I had spent so much time fantasizing over - I just had to fondle them one last time while I still had the chance. As soon as my hands closed on those tremendous tits, I remembered that there was something else I had always wanted to do. Fondling her big naked breasts and thinking about it, I was instantly hard all over again. I took out my cock one more time and quickly jerked off, shooting one last big load across her chest. I gently rubbed my cum all over Cheryl’s big, beautiful tits and left for the night with a huge, satisfied smile on my face.
Damn, now I have something to think about when I jack off, don’t I? Where in the hell was my camera?