Sister n law stories

[tom00799]

I've always had a thing for my SIL. The first time I met her was when my wife and I were dating. Wife and I joined her family for dinner at her dad's house. I remember catching her out of the corner of my eye mouthing to her sister, my wife, "he's cute". That was many years ago. She's older now. Mid 50's but in great shape.

Not too long ago we had a moment that neither of us expected to happen. She was single at the time and was frustrated with the online dating scene. She's the type that has to be with someone all of the time but has standards that are not going to be met dating losers from match.com. She couldn't seem to find anyone with all of the qualities she wanted.* About one in three guys would send pictures of their cock within a short time of email exchanges which I thought was hilarious. She would always jokingly say to me that I'm a one of a kind but I know she meant it.

She and my wife have always been close. She lives out of town but not too far so she visits often. She likes to get her drink on and my wife can never keep up with her. Many times we would stay up after my wife would fall asleep. We would drink and talk about all kinds of things. We have a pretty good connection, the kind she wanted in a man. I knew she had not had a good fucking in a long time, if ever. She used tell me if I wasn't married to her sister she would be all over me.

One night we started off as usual with all three of us drinking. My wife was falling asleep on the big sectional couch we were all sitting on. Wifey finally said she was going to sleep and got up and went to the bedroom. Sis and I stayed up and kept drinking and watching TV. The lights in the room were dim and a fire was going in the fire place. It was winter. I had pj's on with no underwear. She had on a t-shirt with sweat pants. She started to sit closer to me. She eventually snuggled up to me and put her hand on my arm and pulled herself close. She was in a happy state. She was glad to be holding onto a man. I put my hand on her inner knee simply to make her feel comfortable and to innocently give her the idea that I liked it too.

We snuggled for a while like that. Then, out of the blue she said "can I ask you a question?". "Sure" I replied. "Can I kiss you?". "Sure" I said expecting a peck on the cheek. She turns over and plants her lips on mine and sticks her tongue down my throat! We started making out like lovesick high schoolers. She was really getting hot. As we were sucking face, her hand started to move towards my crotch. She kinda hesitated but then reached down and grabbed my throbbing rod through my thin pj's. She started squeezing and tugging on it and let out a little "I want that so bad" type of moan. She was conflicted but could not force her self to stop what was happening. She pulled her lips away from mine and said "I want to suck your cock so bad".

Without hesitating, she pulled my cock out, placed her juicy lips on it and started sucking. Her mouth is bigger than my wife's and her skills are far better. It was fantastic. I worked my hand down the back of her ass inside her pants and started to work her cit with my finger as she sucked away. She was hot and moaning. She pulled up and said "let's go somewhere where we can fuck". I decided to take the gamble and fuck her right there on the couch. I pulled her pants off and went down on her. I was surprised to find that her pussy hair was short and just beyond stubble like she had shaved it bald and it was growing back in. I did not get to eat it very long because she wanted cock. She pulled me up towards her and, as I was sliding my cock in, she said "I can't believe this is happening". I gently slid my cock in. I was surprised that is was so wet and tight. I started to put it to her. She was moaning and saying how it felt so good. What was weird is that it felt like I was fucking my own wife but like it was years ago before my wife discovered her g-spot, but that's another story.

She obviously had not been fucked like that before. She was enjoying it tremendously. "We have to stop, but it feels too good" she kept saying. It was hot and steamy and I was really going at her and I could have come at any moment but was holding back. After fucking for about five minutes or so, the guilt overtook the pleasure. "We have to stop". Knowing that she meant it this time, I quietly and quickly came inside her with out her sensing it. She got up and said "help me find my pants". She got them and wondered off to the room she was staying in. I took a quick look around and noticed her panties on the floor. Good catch I thought to myself. I took them to her room where she was passed out bottomless.

She was asleep when I left for work the next day so I never said goodbye. I can only imagine what she thought to herself when she woke up with a bare pussy. I wonder if she remembered what happened. I wonder if she discovered the cum inside her.

She came back to town a couple of weeks later. It was mildly awkward at first but that quickly changed. We drank and had fun and acted like nothing ever happened. It's been like that ever since with the exception of one deep kiss with lot's of tongue. I need to teach her a thing or two that my wife has discovered like her g-spot and how to be multi-orgasmic. I need to get her off with my tongue and finish that good fucking she really needs. After all, I'm just looking out for the family.

[barnyb]

My SIL had just gone through a separation and was living at my wifes parents house. We had always done a bit of harmless flirting but nothing more than a bit of hassling each other.

She had separated from her husband who she met when young (and got prgo). Now she was free she spent some time in the gym and got some new boobs.

One time we were around her parents house (parents lived overseas) having a family dinner (her, wife my kids, me)

After dinner I picked up the kids who were asleep and put them in the car. Wife grabbed the rest of our stuff and sat in the car.

My shoes were outside the ranch slider which was outside the downstairs lounge - her lounge. SIL had gone downstairs and shut the curtains getting ready for bed. My shoes were outside by the ranch slider but the curtains had been pulled - except for a gap. Now when SIL shut the curtains she would have seen my shoes and known I would come back for them.

Hence, it was all set up. She knew I would see her. She could claim innocence. The show proceeded.

I came back for the shoes and reached down to pick them up. I then noticed the curtains had not been fully pulled and there was a gap which looked into the lounge and bedroom. At the closet was SIL reaching up for some clothes. She had her back to me and pulled her top off then slid off here trackies - no knickers. Back and side on view reaching up high into the closet so her legs and bum were nice and taunt. I didn't move (and no red blooded male would). She fiddled around for a short while all the time on tip toes with butt nice and firm. This is when I realised that she had clearly been working hard at the gym. She pulled down a top and then started to put it on her head. At the same time she turned to me and fully front on fiddled with her top hiding her head but exposing her new boobs and fully shaven sn*tch. She then walked towards me with top over head and disappeared into the bathroom.

Show over. She set me up and showed me her fantastic bod, without being seen as an exhibitionist. I went back to the car.

[ThomasMoore]

A few years ago wife and I went to Aruba with her older sister and her husband and stayed with them at their timeshare. My brother in law is a real drag and stick in the mud and rarely if ever left the poolside bar. On the second morning, my wife suggested that we should all go down to the beach since she was bored with the pool and bar at the condo unit. Of course brother in law said no, so my wife and I headed out to the beach alone. A short time later my sister in law came walking down the beach and joined us. We were all a little tired after our somewhat late night at the casino nearby, and my wife quickly dozed off. I sat chatting with my SIL and in a short time fell somewhat asleep as well. My wife was exhausted and was sleeping heavily when a woke up a short time later, my sister in laws towel was still next to me but she was down in the surf. When she saw me sit up she waved to me and came out of the water, topless!! My wife and her family grew up pretty conservative and I was shocked to see her sans top! Both wife, and sister are full chested yet rather slim and I marveled at my sister in laws heavy large breasts as they swayed from side to side as she walked back to her towel. I handed her a clean dry towel when she arrived thinking that she would dry off and cover up, but to my surprise she dried off and sat next to me topless chatting for the next half hour or so. I loved being right next to her and watching her large nipples get hard as she would catch me looking at her. I have more experiences from this trip, as well as other things that have happened over the years that I will write about when I have more time.

[xxxxenophile]

Originally Posted by ThomasMoore

I have more experiences from this trip, as well as other things that have happened over the years that I will write about when I have more time.

Hope you have time soon! Sounds like she needed some attention

[enjoyslife]

Sounds like a nice trip with a woman like that just casually sitting and talking topless next to you. Looking forward to your other stories too.

[fapfreediet]

I've had an eye out for my SIL (wife's youngest sister) since we met over 20 years ago. She has small breasts and liked to wear loose t-shirts around her parents house, giving a nice downblouse of her dark areolas and nipples. Always some mild flirting despite our language barrier (wife and her sis are from Brazil) but it never led to anything. Wife and I have had phenomenal sex that whole time and I've never cheated.

When my wife was pregnant with our second child, her youngest sis came for a visit. I enjoyed my wife's pregnant body but she was bloated and I really missed her athletic flexibility. Her sister was really showing off her hard body while here (flashing white cotton panties in a short skirt in the rear view while I was driving, with my wife in the passenger seat, low cut tank tops, tight workout pants with cameltoe, etc) and I couldn't get her out of my head. Even jerking off while sniffing her panties wasn't enough. I devised a plan to peep her in the bathroom/shower with the shiny side of a blank DVD barely pushed under the bathroom door.

I made several attempts being as careful as I could in our small house (did not want to get caught/divorced just to see her pussy!) but always missed out. The morning before her flight back home, she told me she was going to hop in the shower. I pulled the disk out and set up for her to get out of the shower but she stepped out with the towel wrapped around her waist. In the big mirror the door faces, I could see her breasts slightly but the steam from the shower was working against me. When she started toweling herself dry close to the door but facing the opposite direction (the mirror), I pushed the disc farther under the door to see if it improved my view.

She let out a surprised, Portuguese version of "What the hell!" and my stomach sank = busted! Instead of saying something to me, she squatted down inches above the disc revealing her beautiful pussy lips, the finely manicured hair around it. I got a real eyeful! I pulled the disc and jerked off in my bathroom. It was so good, I let out a moan she could probably hear through the wall. She dressed and I drove her to the airport, but we never spoke of it. I've had that good memory for almost 15 years.

[tinycuties]

i wish i could som how get with a sister in law. but that must be tough and ackward.
either it goes great, or absolutely horrible lol

[daskers]

Originally Posted by xxxxenophile

It sounds like the women in that family have very open minds, and strong physical needs! Earth needs more ladies like that

Well I just fucked Karen once, her mother was further down the road when I fucked her, as said it was a year before my brother and Karen divorced that I nailed Marge the mother twice. But I would also haft to agree with you, it was strange it turned out that way and it did make me wonder about them.

[richyguitar]

I always like to think back to a great moment of accidental / unaware nudity concerning my girlfriend’s little sis. My gf was still living at home with her mom and her younger sister at the time. I had only stayed overnight with them on weekends a few times before. On Sunday mornings we would have breakfast in their kitchen all together. Her sister usually got herself out of bed a little later and would typically, still half-asleep, come stumbling into the kitchen for a cup of coffee and sit down with the rest of us. On that very morning she had just come out of bed again, still wearing her red T-shirt from the night before and some loose-fitting satin panties (like boxers but especially made for women; a bit like hot pants-style with intentionally short legs, but not as tight). She helped herself to a cup of coffee and sat down sideways to me on the bench seat.
At that time she was arguing a lot with her mom about people she wasn’t supposed to hang out with – not at least her first boyfriend, being 11 years older than herself. So it didn’t take long until her mom would begin quizzing her about where she had been the night before and stuff like that. While engaging in the first discussion of the day with her mom, she was rising up her left knee, putting her foot up on the bench and then placing her elbow on her left knee. Her tiny naked feet looked pretty sweet by the way, but much more mind-blowing was the view her new seating position suddenly allowed me. Her thin bent legs were leaving a large gap between her thighs and her loose, slightly oversized panties. It literally took my breath away as I realized that the little fur that I was seeing down there belonged to her vagina and that her position allowed me a perfect side view on her nude pussy lips. The most thrilling thing about the situation was that, being distracted by the conversation with her mom, she was sitting like that for minutes, completely unaware she was just showing me her pink bits. If she knew she would have sunk into the earth out of shame! My girlfriend was sitting at the opposite side of the table and had no clue of how her little sister was just freaking me out.
Back in my girlfriend’s room a little later, I was still so horny that I let her know I was in the mood for getting it on. She somehow found it funny that the “family breakfast” had apparently made me horny and kept joking about it for a while, but was eventually giving me a quick handjob while we could still hear her sister and mom quarrelling with each other. I’ve never told her why I needed her hand so badly that morning… but when I see her sister I always remember the look of her pink bits and feel a little privileged for being one of the first guys to have ever seen her pussy.

I’ve really liked her since that day. As long as my girlfriend was living at home - with the women’s unattended laundry always in reach - I quite regularly took the chance to jerk off while sniffing some used panties of her sister … unfortunately, I haven’t had the chance for years, but I still know how her pussy smells and will (hopefully) never forget her aromatic odor.

[jmontagn]

Now-days, my ex wife’s Pam’s sister, Katrina is the epitome of virtue and prudishness. You would never suspect that she was once a wanton sl*t who had almost no inhibitions. Pam told me many stories about Katrina’s sexual adventures. This is one of them.
A few years into our marriage, we were in bed watching “The Godfather” on cable and Pam confided in me that her father had once threatened to go to the mob to arrange a hit. I was more than a little surprised because her father seemed to be a pillar of their community, a well-to-do, white, upper middle class, church-going, mid-westerner. I asked, “He must have really been upset about something. What would get him so desperate?”
“My sister, Katrina! What else? She had just quit high school, two days after her 18th birthday, one month short of graduating and had an argument with my mom. She ran away and we hadn’t heard from her for a couple of weeks. Mom and I had kept tabs on what she was doing through our network of friends. She had been bouncing around staying at one or another of her girlfriends’ parents’ houses and within 10 days she was working at a fast-food restaurant near downtown and sharing a flat with a co-worker. Everything was fine for a couple of days, until one evening when my dad went over to see if he could talk her into coming home to finish high school. He came home fuming mad. I was upstairs in my room studying and heard him ranting at my mom that his daughter was a sl*t. I went down the hall to the top of the stairs to hear because I was afraid he might have found out that I was in love with a guy and had been necking and petting with him, but just then he told mom that he had walked up to Katrina’s place and when no one answered the doorbell he went to the window and saw her naked on the couch with a black guy on top of her. He was screaming at mom that he knew some people and would have that bastard killed.”
“Wow!” I was flabbergasted. “Did he actually have the guy killed?”
“No! Mom calmed him down. She made him sit down and they had a few stiff drinks and saner heads prevailed. My mom and I went to the restaurant the next day and she made my sister an offer she wouldn’t refuse. Katrina had run away because my mom wouldn’t give her the money to go to San Francisco to live and do the hippie thing. Mom simply told her she would give her the money and arrange the trip for the following week. All Katrina needed to do was come with her right then. To no one’s surprise, the three of us left the restaurant a big happy family and as usual Katrina got what she wanted.”
“You mean that she concocted the whole scene to get your parents to foot the bill for her to become part of the Haight-Ashbury sub-culture?” I asked in a somewhat envious tone.
“Not really!” Pam answered. “She and I had a girl-to-girl talk when we got home and I asked her if she had planned the whole thing. She said not the whole thing and that she was surprised that it had taken so long for mom to give in. That’s when I asked her directly if she had set-up the black guy and used him too. She seemed oblivious to my dad’s being there the night before and asked me what I meant by that. That’s when I told her about what dad had seen and what he told mom about having the guy shot. She started to cry because she was upset that she had caused so much trouble. I asked her if she was in love with the guy and she said not really but he really was good in bed. The next day she told me that they just used each other for sex and that neither of them wanted anything more than that. I was a little giddy and asked her if it was true that once you’ve had black you never go back. She smiled back that it was great but she didn’t care what color it was as long as it was big and the guy knew how to please her. She did say that black would definitely be part of the palate from now on.”
I asked her, "Did Katrina tell you how she met him and what did they do together?”
“During our girl-to-girl, Katrina told me she met Sam the week before at the restaurant where he was also working and they would flirt during work. One night they had to close the place alone and while they were cleaning up and setting up for the next morning, they flirted as usual and she teased him, ‘You’re all your talk and no action and all your talk is getting me horny!’
“Sam teased her back, ‘I’m horny too! What are we gonna’ do about it, Kat?’
“Katrina said, ‘I ignored his remark and went into the ladies room to change and had my uniform off when I heard the door open. Standing there in my bikini panties (Back then she never wore a bra.) I turned around and saw Sam coming toward me. He was naked and sporting a huge hard-on. Before I knew it we were locked in a passionate embrace, kissing and groping each other. We edged over to the couch and settled into it. At first we sat side by side but within a few minutes I leaned back and he was on top of me. He broke off our kiss and started to kiss my neck, then my shoulders, then my chest and finally my breasts. The feeling was incredible when he finally took my left nipple between his lips and gently tongued it. When he did the same thing to my right nipple, I had a mini-orgasm and was ready to fuck but Sam had more in mind. He moved from my breasts down my body kissing and tonguing me over my belly, navel and pubic mound until he reached my panty-clad pussy. He kissed me there for a second or two and then proceeded down my thighs and calves and finally kissing my feet and began sucking on my toes, one-by-one. I was in heaven. I never had a guy pay this much attention to me before. I was his. He could do anything he wanted with me, but he still wasn’t finished pleasuring me. He stopped sucking my toes and slowly kissed and tongued his way back up my legs to my pussy. When he got there he hooked his thumbs around the hips of my panties and I raised my hips and he slid them off. Then he very gradually planted gentle kisses around my pussy, finally actually kissing my lips and slowly inserting his tongue between them. I was a cunnilingus virgin until then, but I was being initiated by an expert and my body shuddered with an orgasm. Sam then administered the coup d’ gras, his lips and tongue turned their attention to my clit. I was totally aroused so they had no trouble finding it. First he gently flicked it with his tongue for about a minute until I came again. Then his lips went around it and he sucked on my love button while simultaneously tonguing it. I can’t describe the thrills of the continuous wave after wave of orgasms as he kept this up for several minutes. I almost passed out from the ecstasy.
‘He finally removed his mouth and moved back up to kiss me. I could taste my juices on his tongue and it made me feel so naughty that I broke off the kiss and moved down to kiss his 8 inch hard-on. Pam, you know that I have given several of my boy friends hand-jobs but I hadn’t ever given a blow job before, so I was a little unsure of what to do. Sam sensed this and teased me, “Never seen one this big, huh?”
“’I said, “Never seen one this close.” We laughed and he guided me through the process. I did what he told me to do. First I kissed the tip. He was uncircumcised, my first uncut cock, so I rolled back his foreskin and tongued around the head and he moaned. After a few minutes of this he asked me to put my lips over it and I did. I didn’t need to be told to do anything else. I took as much of his cock into my mouth as I could and started to suck. Sam’s natural reaction was to start fucking my mouth and within a few minutes he was flooding my mouth with his semen. I instinctively swallowed what I could but I gagged a little and a lot of it ran out of my mouth, down my chin and on to my chest and breasts. I moved back up and we kissed and held each other for several minutes before we finally got off the couch and got dressed.’”
I wanted to hear more and asked, “You mean that he didn’t fuck her that night!”
Pam answered, “Not that night in the restaurant but the next day he came to her place and Katrina said they fucked for hours. I asked her about it and she said, 'Sam started the same foreplay as the night before in the dressing room but this time he didn't want a blow job. Instead he had me lie on my belly. He straddled my legs and slammed his hard cock into my pussy. It hurt as he went in. It is the longest, thickest cock I have ever had and I thought he was going to rip me open, but the pain eased almost immediately and was replaced by a wave of cumming as the bottom of his cock touched my g-spot with each thrust. I've been screwing guys for two years but I have felt so full. I must have had 20 orgasms. When he came inside of me I could feel his hot semen hit my cervix and flood my womb and I screamed in a final orgasm. I left my pills at home when I left and my period is a couple of days late. Pam I am worried I might be pregnant with his baby.'
"She started to cry again and I soothed her by telling her that her period was probably irregular because she went off "the pill". Anyway she got her period the night before she left for San Francisco. After hearing about his skill as a lover, I wanted to meet Sam but was too timid to ask Katrina."