The following story took place about 8 years ago and it developed into a 6-year sexual relationship between my sister (then 26) and me (then 23).
We had both just returned from a cousin’s wedding reception and man, were we buzzed. OK, drunk. ‘Jess’ had moved out of the house a few years earlier but was staying at the family homestead for the wedding weekend.
Our parents had left the reception hours earlier, perhaps a bit tipsy themselves, and were snoozing peacefully in their 2nd floor bedroom as we entered the house laughing hysterically (I had dropped my keys 3x trying to unlock the front door). Luckily for the local pedestrians, the wedding was only 2/3 towns away…
We were ‘up’ and not ready to quit partying. The bars were closed, most of the other wedding guests had bailed out earlier, but Jess and I were really having a ball–we were always very close and we hadn’t seen each other very much since she moved out of the house and out of town years earlier. We were going to make this weekend last. After getting settled inside, Jess went out on the patio to smoke a joint (I don’t smoke) and I went into the kitchen to see what we had to drink. Not much booze at my house, usually, but I had a couple of stray beers in the fridge. I turned on the stereo in the living room, keeping the volume low, changed out of my siut and into a bathing siut for a quick swim. I grabbed the beers and headed out to the patio. I took a quick dip; a couple of laps around the pool and I was up, out, and drying off.
Jess was getting stoned. She watched me coming out of the pool and was smiling broadly when I took a spot in a patio chair. She was wearing a short black dress and black nylon stockings. She had left the heels inside the house. Still single and with no current significant other, she was dressed to impress the eligible males at the wedding. And impress she did. The break up with ‘Mike’ had been bad; she didn’t date for almost a year, but she was finally ready to start looking again. The conversation, however, soon returned to the subject of her relationship with Mike. She felt a bit better about her current status, however, because I recently became single myself. We compared notes for a while and she mentioned the time she walked in on Leslie and I while we were in the 69 position.
We laughed hysterically for a bit, trying to keep quiet. Then Jess said ‘Mike used to really love that.’
‘Love what?’ I asked, still laughing.
‘Oral sex,’ she replied. The pot was good.
A few moments of silence passed, then Jess looked at the smirk on my face. ‘What’s that smirk for?’
‘So did Les…’, I said.
More laughter; then, from her, ‘so did you, obviously!’
Through my buzz, I was enjoying reaching a new level in me & my sister’s relationship. We could talk sex now. It was cool! And…different…interesting…
‘Ever do it out here on the patio?’ she asked.
‘Nope. In mom & dad’s bed once.’
‘NOW WAY!’ she wailed.
‘Shhhhhhhhhh!’ I urged.
She said ‘I don’t think I could do it, on mom and dad’s bed…’
She paused and looked like she was thinking hard. She bent a leg to scratch an ankle. That’s one mini mini-dress, I thought…When she put her leg back down the dress stayed up, high up on her thighs. I could almost see her panties as she sat on the deck railing. Ididn’t say a word.
‘Ever have anal sex?’ she asked.
‘Jesus!!’ I almost spit my beer all over the ground. Taken off guard and feeling like we may have taken this a bit too far, I was embarrassed and tried to deflected the focus back to her. I stalled and said ‘have you?’
Jess looked dead serious. ‘No. Mike wasn’t interested and I guess neither was I. But It’s been so long since I’ve gotten laid I find myself thinking about it more and more.’
‘Anal sex?’
‘No, well, yeah, sex in general but… I regret the things I never tried now that I’m alone.’
‘Oh, come on. You know you won’t be alone forever. Before you know it you’ll be having all the anal sex you want,’ I joked. And it wouldn’t take long before she found another guy. She looked so hot when she wanted to, I thought. Like right now…One of the spaghetti straps on that little black dress had fallen off of her shoulders during that last laugh attack; a fair amount of tit was showing.
‘Yeah, joke all you want,’ she said, ‘but I know you feel the same way I do, now that you and Les aren’t fucking. Don’t you ever feel like that last blow job might be your last ever?’ Hearing my sister say ‘fucking’, ‘blow job’ and ‘anal sex’ was having a surprising effect on me; that, her hiked skirt, the half-exposed boob, and the alcohol was getting me aroused. My cock started to expand in my wet shorts. I didn’t think she’d notice; I had checked her out when I was kid, too; I don’t think she ever knew. Besides, she was beautiful! What else would any red-blooded man (or drunken little brother) do but sneak a peak for a cheap thrill?
‘Hey!! You never answered me! “Ever Have Anal Sex!?” she insisted. Did she think this talk was as much a turn-on as I? Or was she just goofing? Something was going on between us but I wasn’t sure what.
‘No….never did.’ I looked up at Jess and she was looking at directly at my swim trunks; specifically the bulge in front. She did notice! I was drunk; I didn’t know how to react. So I didn’t. I just stood there and watched her looking at my hard dick through my shorts. Then I said, ‘I wanted to, but Leslie didn’t.’
‘You wanted to?’ she said, breaking her stare and meeting my eyes again. I saw no signs of embarassment or shame over the fact that she had just been busted spending a considerable amount of time checking her little brother’s rock-hard package. She looked different to me somehow…
‘Yeah–I would love to do that. I’ve seen it in porno and it looks like they all dig it….’ I explained. I was bold; throughout that entire sentence I was staring at Jess’ black panties, now slightly exposed from her shifting position on the railing. Fair is fair. ‘It turns me on to think about it.’
‘Are you thinking about it now?’ she aked as she returned her gaze to my cock, now harder than ever. She was getting bold, too. My heart started to race.
‘Well, talking about all this stuff has got me going a little, yeah.’
‘A little?’ she smiled that good ‘ole sister smile and I knew that whatever was happening here was cool with her. We laughed at my at the scene my hard-on was making and I was really happy that there was no shame in it; this was fun, exciting, and really comfortable at the same time.
I opened a beer. ‘I fantasize about it alot’ I said.
‘When you jerk off?’ she said. There; that time I saw it; a slightly sinful look crossed her face when she said that. She was getting off too.
‘Yeah–when I jerk off. I wish I was fucking a girl up the ass.’ Jess shifted a little on the rail. ‘But as many times as I’ve beat myself off to that fantasy, I still have no idea what it’s really like.’ She was breathing heavily. Our eyes were locked together. ‘I’m dying to know.’
Jess’ voice was really low, quiet. Moments passed…’Me too. I wanna know, too. Maybe…maybe sometime…would you want…’ She was having a hard time, but I knew what she was trying to say. All the while her eyes were focused on my cock. I decided to help her out.
I stood up and took a step toward her. ‘We could try it, right? I mean we know each other and love each other, right? We feel safe with each other—‘
She interrupted. ‘We could just try that, just that alone…it wouldn’t be like we were having sex, or anything…Should we? It’s just my butt, it’s not my…vagina. Would it be OK? I mean would it be wrong?’
Wrong shmong! I couldn’t find a single thing wrong with this. I didn’t ever want to do anything to hurt my sister. We were both obviously horny as hell and willing to help each other out of this sexual curiosity thing. In fact it couldn’t make more sense!! I told her so and she smiled as she listened. She grabbed a beer and said ‘Let me go in and get ready. I’ll meet you in your room in 5 minutes. Just anal sex, right?’
I assured her we would just satisfy our mutual curiosity and that was it. ‘We’re just helping each other out with something, that’s all!’ She smiled again and hopped down from the rail. Her braless boobs bounced as she hit the patio. She looked at me and nodded her head excitedly. ‘We’re not going to fuck; we’re just kind of trying something out on each other!’
‘Exactly! And if one of us doesn’t like it, we stop! That’s it!’ I said. She bopped eagerly into the house and I saw the bathroom light go on.
I had a moment to myself then. I saw this as a wondrous thing: not only was I going to experience anal sex, but I would experience it with my loving, caring sister who just happened to be a complete babe!
I downed another beer and headed into the house. I walked down into the finished basement where my room was, my parents now snoozing 2 floors away. The door was open and my small reading lamp was the only illumination. I thought I could make out my sister sitting on the edge of my bed; as my eyes adjusted, I saw that she was still wearing that black dress. The stockings were gone. The radio was on.
She had it all worked out: ‘Okay. Now. Come on over.’ It was kind of funny becuase she was really stoned; but things quickly got real. She moved to the center of my bed and bent over on her hands and knees with her butt facing me. She reached around to pull up the dress over her ass to expose her butt to me. My heart was a hammer in my chest. But as I approached the bed and sat down, I saw that my sister still had her panties on–a black thong. ‘I’m just gonna pull this over like this so you don’t see the other stuff, OK?’ She slid a finger under the thong and pulled it over to the side, exposing her little brown asshole and a fair amount of light brown pubes. I slipped off my shorts. She looked back at my fully exposed crotch. ‘Ready?’
Well, I’m unhappy to announce that my dick had lay down and died. Maybe it was the beers, maybe I was tired, maybe it was a bit of nervousness at having to perform sexually for the girl who had humiliated me so often as a kid, but it just wasn’t happening. I didn’t say so, though, and moved over behind her and tried to concentrate. I laid out the shaft over the cheek of her ass, and I heard a gasp. I slid it up and down in between her cheeks and the feeling was exquisite. Jess started panting like a dog. She let out an almost-moan; as I continued sliding my cock up and down the cleft of her cheeks I felt the blood rushing back. Yes! It would be stiff in a minute, but Jess was impatient. To my utter shock and surprise, she wheeled around and said ‘This always worked for Mike’ and put one hand under my ball sack and the other around the base of my semi-hard dick and pulled the whole package toward her mouth. ‘I know you really love this, but try not to get carried away, OK? I’m just helping to get you hard.’ In a second, she was giving me head!! My sister was sucking my cock! God, it was good! To hear that familiar slurping noise and look down and see you own sister giving you head is a feeling I could never describe! She moved her head up and down on my stiffening member as she pulled and pushed my groin into her face; the feeling was fantastic. I had imagined that my sister was experienced in sex, but never thought of how good she might be at sucking cock. In my excitement I reached down and tried to slip the straps on her dress down to expose those wonderful boobies, but she relinquished my balls and pushed my hands away, mumbling ‘MM-MM! MM-MM!’ as she swallowed my dick. She was all buisiness. Don’t get greedy, I thought. You’re gonna get her ass! Don’t blow it!
Cock now rock-hard again, (that was the only time I’ve ever been GLAD Icouldn’t get it up!) Jess spun around again and pulled her thong over. ‘OK…do it! Stick it in!’ As I slid my dick around the general area and up and down her crack, she pleaded ‘C’mon, Tommy! C’mon! Do it! Do it!’ I finally got my cockhead poked into the opening, and tried to push it in, but I think Jess was far too wound-up to be reaxed enough to let me in. I pushed really hard and she said ‘OW!’ I backed right off.
‘You’re too tense! you have to relax!’ I urged. ‘Those porn stars have tons of experience; you gotta smoke another joint or something.’
‘I don’t need any more pot! I need you to put it in my ass! C’mon Tommy! We’ve come this far! Put it in my ass, please!’
‘God, Jess, believe me, I want to, maybe this position isn’t right.’ I said.
‘What other one is there?’ she asked. I remembered a position I had seen in porno movies; just like the missionary position but the woman shifts her pelvis a little higher and lifts her legs up to her chest. I described this to Jess and she immediately assumed the position. Her thong immediately became a problem. She couldn’t keep it pulled over while using both hands to keep her knees up at her chest.
‘Gotta take this off, Jess. Don’t worry, no funny stuff. I won’t look; I’ll turn the lamp off if you want, but you gotta take this off.’
Jess got up from the bed. She was transformed. ‘Fuck! It’s off!’ She quickly stripped off her thong and threw it. ‘OK? How’s this? Huh?’ She was so in need of my dick in her ass I think she lost her mind. Then she pulled the entire dress over her head and threw that too. My big sister–totally nude. I will never forget the first time I saw her naked, hot, and craving my cock. A vision from my most shamefull adolescent fantasies come to life. Her tits were perfect. Her nipples were puffed out and their tips were hard. Her tan lines seemed to glow in the dim orange light. Her chest heaved with her heavy breathing and I could actually smell her wetness in the air. I looked at her pussy and saw how wet she was; her pubes were damp and matted. The insides of her upper thighs glistened. She spoke forcefully: ‘ OK. Now please let’s do it, Tommy. I can’t stand it anymore! I need to feel your cock in my ass!’ She motioned me over her. Hearing her talk like that was killing me.
She jumped back into bed and got into position. Before I joined her, I opened my dresser drawer and removed a small platic bottle of baby oil that I often used to masturbate with and said ‘This might help. too.’ I couldn’t believe I had not thought of this earlier. I started to open the cap and was about to squeeze some into my hand when Jess said ‘No, let me, Tommy. I want to do it. Come here.’ I walked back to the bed and handed the bottle to her. My sister then covered my cock in warm, slick lube, stroking up and down just like I did. ‘It’s bigger than I remember. I hope this works.’ She looked at my cock with hungry, anxious eyes. Then she spread some oil around her asshole. As she lay back she said: ‘Alright. Now put that big cock of yours up my ass, little brother. Fuck my ass!’
She was on her back with knees up at her chest and I was kneeling at her butthole with my lubricated dick in hand in a split second. I looked down and got a greedy look at her sopping wet pussy, but that was strictly off-limits. After a bit more hit and miss, I found the correct angle of attack. I pushed the tip in. When my cockhead entered her anus, her eyes opened wide. This was it! She looked up at me and said ‘Do it, baby brother! Do it! Fuck my asshole! Buttfuck your big sister!’ I pushed it in further, then pulled out a bit; in even further, then out a bit. 5/6 strokes later and I was in as far as I could go. I held it there for a while, and looked at Jess, who was pinching and pulling both nipples rapidly with eyes closed. I was feeling a profound lust.. ‘How’s that big sister? Like my cock up your ass? Huh? Should I fuck your ass with my hard cock? Huh? Tell me to fuck your ass!’
‘Oh, God, Tommy, fuck me! Do my asshole, baby!’ I started slowly pumping my pecker in and out of her slick, super-tight butt. I looked down and I could see her cunt lips opening and closing with each long stroke of my cock. Her exposed clit was swollen and wet. ‘Ohhhhhhhhhhhh! I love it! Do you like it Tommy? Do you like my asshole? Ohhh, your sister loves your big fat dick in her ass, baby brother! It’s sooooooo gooooood……’ My strokes were increasing in speed and strength as we talked dirty to each other.
‘Oh yeah, baby, it’s awesome! I love fucking your tight little asshole. Feel your brother’s cock, Jess? You like your brother’s hard cock fucking your ass?’ My cock momentarily popped out of Jess’ butthole; she yelped as if injured and I guided it back in. Back inside, I really started ramming her ass. A renewed wave of lust swept over me as I watched my sister reach down with one hand and start massaging her cunt. The moaning coming from her now was intoxicating. The tit that she wasn’t molesting was bouncing to and fro with our rythm. I arched down and took the nipple between my teeth and gently bit as I fucked. ‘Ohhhhhhhhh, no, Tommy…..’ she half-heartedly resisted my nipple play.
Once again, my dick popped out. I was fucking like a machine, however, and didn’t miss a stroke; when I stuck it back in it suddenly felt different. It only took a second before I realized that I had just thrust my cock inside my sister’s sopping puss. In a micro-second, my mind reeled; I had crossed the line we set, it was an accident, should I stop, will she hate me, it feels fantastic, fuck her silly, she loves it—time just seemed to stop. We were both suddenly completely sober. Now there could be no question. I was fucking my sister.
But then I noticed that her hand had not stopped working her cunt; she was still working away at the top of her pussy mound. ‘Oh please…don’t worry just fuck me Tommy keep fucking me fuck my pussy fuck my ass fuck my mouth just don’t stop please don’t stop’ she said breathlessly. ‘Fuck my wet pussy.’ I didn’t need to be asked twice. I started pumping her lovely hole. ‘Yeahhhhhhhhhhhhhh baby.’ Her cunt was hotter and wetter than her ass and her ass was FINE. She wrapped her legs around my back and we worked together. She planted a big wet kiss on my lips and we were soon tonguing each other like there was no tomorrow. After a while I pulled out and guided her back into the doggy position. I shoved my prick back into that juicy sister-hole and grabbed a butt cheek in each hand and fucked her from behind. This position elicited an entirely different set of moans and grunts from Jess. She must have repeated my name 100 times; then she had her first violent orgasm. I could feel her juices spreading over my balls and inner thighs. She squirmed up the bed and lowered her stomach down until she was laying flat; I never let go of those cheeks and followed her down fucking all the way. Her beautiful butt was upturned to meet my cock’s thrusts; I was pounding her into the mattress and she was trying in vain not to scream. She pushed her face into one of my pillows and shrieked as she came a second time.
I wasn’t about to stop fucking my sister yet; I needed to shoot my hot load in her, on her, whatever; but she quickly turned over, removing my cock from her cunt. Apparently her clit just couldn’t take anymore of our frantic fucking. ‘I know you wanna come, Tom. Let me give you head, just like Leslie did when I walked in on you.’ As she spoke, she maneuvered me onto my back. ‘You know, that was the first time I ever saw your big hard cock. I thought about it for months; your huge cock and how beautiful it looked and how lucky Leslie was and what it might be like to suck off my own brother while he ate my pussy.’ She started masaging my balls and stroking my shaft. I needed to come so badly my entire body ached. ‘I thought these thoughts were wrong and felt quilty that I couldn’t stop imagining it. But I held on to that memory and tonight proves it was right, right, Tommy? This can’t be wrong Tommy! It feels so good…Your cock tastes so good!’ And with that, my dick disappeared into her soft and slippery mouth. She blew me like she loved me; and I was never more sure that she did. She was on all fours. I slid my upper body over toward her groin. I reached up with both hands and motioned her to spread her legs. She did and I slid under her pussy as she continued to suck me off. I pulled her butt down towards my face and probed her wet slit with my long tongue. Classic 69. She pulled her head off of my cock and let out a loud ‘OhhhhhhYeahhhhhh’ as I started to lick my sister’s dripping cunt. She gushed as I worked her clit; we each at the same time inserted a finger into the other’s anus. As she inhaled my member, I pulled my soaking wet face away from her gash and said, ‘Suck that cock, Jess. Your brother loves the way you suck his dick. No one sucks it like you do. Work that finger. Make your brother come! Make me come just like I did when I was a kid beating my meat thinking about my big sister’s body!’ The more I said, the harder she sucked. Soon, I could no longer concentrate on eating Jess’ pussy or fingering her ass. I was going to come bigtime. That was all I could think of. Jess could feel me asshole tightening around her finger; she could feel my balls clenched against my body; it was going to happen. She was ready. I was so loud I was convinced I’d wake up my parents, but I didn’t care. I came in a series of giant, hot, wet bursts of thick cum; my sister struggled to swallow every drop of the thick white goo. She almost got it all; some leaked out of the corner of her mouth and onto her lower lip. My ass must have been about 2 feet off the bed when I finally relaxed; I’m surprised I didn’t snap Jess’ middle finger with my sphincter.
My sister swallowed hard, wiped the excess from her lips and said ‘Nobody could ever tell me there’s anything wrong with this, Tommy. I want you again. And again. And again….’
‘I’ve been waiting for this forever, Jess. We can’t get much closer than this, can we?’
She closed her eyes, shook her head, smiled and said, ‘Maybe I should move back home,’ just before she fell into a deep sleep. I wasn’t far behind.