Sandy's Sister

Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me.

Note: If you haven't already, read the Learning Experience stories and Twentieth HS Reunion, which are prequels to this story.

It had been too long since the last time that Sandy and I'd had the opportunity to get together for some hot, naked fun. It wasn't a lack of desire but the difficulty of coordinating across the distance between our respective homes. When I heard from her younger sister, Sherry, that she would be coming out my way for a conference and was wondering if I'd be interested in dinner, I wasn't sure whether Sherry knew anything about Sandy's extramarital dalliances with me. Regardless, I was going to meet up with her since I'd known her for as long as I'd known Sandy, but I couldn't help wonder whether Sandy had suggested meeting up with me and, if she did, whether extracurricular activities had been mentioned. Sherry had a figure not unlike her big sister, with nice curves and a significant rack, so I'd be up for it if the opportunity presented itself. On the other hand, if it was an innocent dinner, I'd be fine with that, too.

I never asked Sandy about it because it seemed like posing the question "Did you want me to fuck your sister?" might be a little awkward...especially if she didn't. Figuring I'd just play it by ear, I made plans to meet with Sherry for dinner after I got off work on the one day she'd be in town before she headed into the mountains for her conference. I called her as I left my office and she met me in the lobby of her hotel. She looked nice in a sundress and sandals and gave me a hug but I tried not to let my mind wander to what might be under her dress. I'd picked a restaurant we could walk to and it was a pleasant evening so we strolled down there casually while starting to catch up.

The restaurant had an outstanding beer list and we were through our first one by the time our entrees arrived, so we each had a second. I warned Sherry about being at altitude and drinking, so she slowed down on the second one as we ate. By the time we'd finished eating and were nearing the bottom of our second beers, it was still early so I asked her what she wanted to do once we'd settled up the bill, assuming it wouldn't be more drinking.

"Well," she started, hesitantly, "I have a very nice hotel room. We could go back there if you're interested."

"What happens in the hotel room stays in the hotel room?" I asked, definitely interested.

"Absolutely," she replied with a sultry look.

"Sounds like a good plan," I told her, so we got the bill settled and headed out.

As we walked along the mall, she took my arm but that was all, so I assumed she got the importance of discretion. Once we found ourselves alone in the hotel elevator, however, it was another story. As soon as the doors closed, her arms were around my neck, my hands were on her waist and we were making out. She was pressing against the growing bugle in my pants so I moved my hands down to her ass and pulled her against it. By the time the elevator stopped, I was ready to burst out of my pants and I was thinking about how wet she probably was. She led me to her room, unlocked the door and we hurried inside.

We were back in each other's arms at the foot of her bed, my hands immediately going to her ass as we made out again. I could feel her panties encasing her ass and wanted to see them, so I moved my hands up to the zipper at the back of her sundress and unzipped it. We broke apart as I started to slide the shoulder straps down her arms, revealing her luscious tits within her bra. Once her arms were free, she shimmied the waist over her hips, causing her tits to jiggle and definitely grabbing my attention. I backed up and took in her figure in just bra and panties before reaching for her tits and caressing her hard nipples through her bra. We made out again as I fondled her tits before reaching back to unfasten her bra. I backed up again as I started to slide her bra down her arms, my eyes going wide as her large areolas and thick nipples were revealed.

As her bra dropped to the floor, I was leaning down to lick and suck her hard nipples while caressing her soft, smooth tits. She was moaning softly and running her fingers through my hair while I stimulated her tits but I soon dropped one hand to the front of her panties and started to caress her pussy through the thin, damp material. She moaned a bit louder and parted her legs slightly, giving me better access but, instead of slipping my hand inside, I dropped to my knees and started to slide her panties down. I ran my hands over her ass while sliding her panties over it and watched closely as her trim, brown bush was exposed. While helping her step out of her panties, I kissed the smooth skin of her lower abdomen and hips. I was fully intending to eat her pussy when she stopped me.

She had me stand and started to raise my shirt over my head. I raised my arms to allow her to remove my shirt while my attention was still on her big tits. As she went to work on my belt and pants, I started to caress her tits again, at least until she dropped to her knees to take my pants and underwear down. With my rigid cock bouncing near her face, she helped me out of my shoes, socks, pants and underwear. She then took my cock in her hand while still on her knees, pumped it and licked the head before standing and suggesting we get onto the bed. She climbed onto the bed with me and, after making out some more and caressing each other's bodies while kneeling in the middle, she had me lie on my back and immediately straddled me. I was admiring her curvy physique, her swinging tits and her trim bush as she reached for my cock and lowered herself onto it.

I reached for her tits as her hot, wet pussy engulfed my cock and we both moaned. While she started to slowly ride up and down on my tool, I was caressing her soft, smooth tits and brushing my palms over her hard nipples. After experimenting a little bit, she found a movement and pace that apparently pleased her, so she was riding me with a smile on her face, letting out the occasional moan. I was enjoying her tits, but I also let my hands roam over her hips and waist and around to her ass while watching her tits bouncing. She closed her eyes but mine remained open, taking in as much of her as I could. There was only a hit of resemblance between her and Sandy in her face, probably not enough to pick up on if you didn't know they were sisters. Her tits were in the same category as Sandy's, nice and big, but Sherry's curves were a little bit less pronounced. It occurred to me as I relished the feel of her pussy sliding up and down my cock that Sherry also had never had kids, so she was a bit more snug, as Sandy had been back when I'd first started fucking her.

The harder she rode me, the more her tits were bouncing and the more they were hypnotizing me. When she leaned forward and planted a hand on either side of my head, I found them in my face and started to immediately lick and suck her hard nipples again. I fondled her swinging tits a bit, too, but my hands were soon back on her ass, pulling it down as I pushed my cock into her as deeply as I could. She was getting louder as her pussy became hotter and wetter so I knew, despite never having fucked her before, that she was close to cumming. I wasn't aware of how close she was until she suddenly slammed herself down on my cock and just sat there while tremors passed through her body. I could feel the goosebumps on her skin as she let out a long sigh.

When I was certain she'd finished cumming, I rolled her over onto her back and went right back to fucking her. She quickly recovered and was raising her hips each time I thrust into her, allowing me to penetrate her deeply. We started making out again as I felt her tits moving beneath me and enjoyed the feeling of my throbbing cock sliding in and out of her snug, slippery pussy. My orgasm was slowly beginning to build and, as I savored the pleasurable feeling of fucking her, I was also considering whether to just cum inside her or to go with something else. Figuring we had the time available for trying a variety of things, I decided on something else.

I went on fucking her missionary-style while my orgasm continued to build and I was thoroughly enjoying it. Once it was getting close to cumming, I slipped out of her and straightened up on my knees. Grabbing her legs, I pulled her down closer to the center of the bed and away from the pillows, then swung around and positioned myself over her in a sixty-nine. As I was admiring her trim, brown bush before diving into it, she wrapped her lips around my cock and began to suck it. I moaned and just enjoyed it for a moment before lowering my head and running my tongue up her slit, tasting her pungent nectar. We both immediately went to town on each other. I was lapping at her pussy, slurping up her juices, before slipping a finger into her and focusing on licking and sucking her clit. She was sliding her mouth up and down my cock while pumping the base in her hand.

As focused as I was on eating her pussy, I was still savoring the pleasure that her mouth was providing as my orgasm began to build more quickly. I could feel my cock swelling even more, but she remained intent on repeatedly inhaling my throbbing tool. As I got closer and closer to cumming, I had to stop eating her for a moment and just enjoy her oral talents. I continued pumping my finger in and out of her and was admiring her pussy as the pleasure built. With a groan, I finally started spewing into her mouth and she moaned as she swallowed it down. Once I was spent and she had nursed the last drops of cum from my cock, I went back to licking and sucking her clit. With her attention on her own pleasure, I could immediately feel her pussy becoming wetter and more engorged.

She let her head drop back and rocked her hips toward my face as she got closer to cumming again. Without a cock in her mouth, she was getting quite loud, which made me happy that she was feeling good and wasn't shy about expressing it. I could feel her starting to tense up a little as she was on the verge of cumming then she went limp and her entire body shook as her orgasm coursed through her. I kept eating her until her moans and shaking tapered off, then raised my head and slipped my fingers out of her. I moved around to lie beside her and we moved up so that the pillows were under our heads as we recovered.

Once we'd both caught our breath, we were chatting a bit, both about what we'd just experienced together as well as entirely unrelated things. I was lying on my side and she was on her back so my attention was continually drawn to her tits and her pussy. It wasn't long before I was casually caressing her tits as we were talking, still relishing the opportunity to get my hands on them. Her breathing changed a little bit when I started to focus more on her hard, thick nipples and, when she ended up reaching over for my growing cock, I propped myself up and lowered my head to lick and suck them. My hand ended up trailing down over her stomach to her trim bush and, after gently running my fingers through it, I slipped a finger down over her dripping slit.

She let out a moan as I explored her pussy, which was overflowing with her musky juices again. I was getting ready to kiss my way down over her stomach to bury my face between her thighs again when she indicated that she had other plans.

"Feels like you're ready to go," she said, pumping my cock, "How are you going to give it to me?"

"How about if you roll over and stick that sweet ass up in the air for me?" I replied.

She rolled over and got her knees under her, keeping her face on the pillows, while I moved around behind her, my rigid cock jutting out in front of me. Before slipping into her again, I leaned down and lapped up some of the juices flowing from her pussy for a moment, causing her to moan and writhe, then ran my tongue up over her asshole. I was also massaging her ass cheeks until I started guiding my cock back into her hot, wet pussy. I took her by the hips and eased it all the way in, relishing the feel of being embedded in her again, stopping once my hips were pressed against her ass. Once I started to slowly fuck her, she reached back between her legs to caress her clit.

Her pussy felt so amazing that I just focused on the pleasure I was feeling as I watched her ass jiggle each time my hips tapped against it. I was sliding the full length of my cock in and out of her nice and slow while appreciating how incredible it felt. I had no desire at that point to change positions other than to lean forward slightly and slide my hands up from her waist to her swinging tits. I think my cock actually got even harder as I felt the soft, smooth flesh in my hands and started to gently caress them. I was thinking that I'd just continue fucking her like that until I needed to take off for the night but, the longer I fucked her, the louder she was moaning and the wetter her pussy was feeling. It appeared as though Sherry was building up to another orgasm more quickly than I was, so I had to consider if I wanted to change anything once she'd cum again.

As she got closer to cumming, she started to push back against my incoming thrusts. I reluctantly released her succulent breasts and took her by the hips again so that I could fuck her harder and hopefully provide her with even more pleasure than she was obviously already experiencing. I tried to just keep the same pace that she was, though that continued to increase as her pussy got hotter and wetter. I was starting to feel the stirrings of my own orgasm, but I had no doubt that Sherry would be there long before I was very close. When she slammed herself back one last time and just held herself there with my cock buried deep inside her, I felt her body trembling as it was covered with goosebumps. I didn't try to keep fucking her, instead just let her do whatever she needed to experience the most pleasure.

By the time she'd finally finished cumming, I knew what I wanted to do next. I slipped my cock from her hot pussy and had her roll over onto her back. Moving up, I straddled her and lay my cock between her tits, which she then squeezed together around it. Gripping the headboard and looking down at her tits, I started to slowly fuck them and moaned at the feeling of the soft, smooth flesh on my throbbing cock. Sherry was looking at my cockhead as it kept sliding toward her face and I wondered whether I'd be able to hit her chin once I blew my load. I'd already cum in her mouth, so I wasn't planning to finish there; I was going to fuck her tits right up until I came and, as good as it was feeling, I wasn't expecting it to take much longer.

I kept a nice, slow, steady pace while savoring the slow build of my orgasm thanks to her luscious titties. The pleasure was incredible and just continued to get even better the longer I slid my cock against her soft, smooth flesh. I increased my pace just slightly as I got closer to cumming but I was not giving her tits a hard fucking. When I did finally explode onto her sternum, her eyes went wide and her tongue came jutting out, though I don't think I managed to hit it. My cum pooled on her chest as I enjoyed the wave of pleasure washing over me but she just watched it while still holding her tits in place. Only once I was spent and had slipped my spent cock from her cleavage did she abandon her tits and start to scoop up my cum with her fingers, feeding it into her mouth.

As she devoured my load, I lay beside her again and watched, reaching out again to caress her tits. When she'd finished cleaning herself off, she turned and smiled at me sheepishly. I ran my fingers through her dark brown hair then kissed her, despite her cum breath.

"How much longer can you stay?" she asked.

"Not long enough for another round, I'm afraid," I replied.

"I didn't figure," she said, "but I'm glad we were able to get in a couple. I'll have to be up early, anyway, to make it to my conference."

We talked for a little while longer before I needed to hit the road and I assured her that our encounter had absolutely been an unexpected treat. She remained naked as I got my clothes back on so that I was certain that the image was imprinted into my brain. We hugged and kissed again before I slipped out the door and headed for home.

I was still thinking about her over the next couple of days, with good reason since we'd had such an incredibly hot time and her body was a force to be reckoned with. I was pleased to get a couple of texts from her during her conference, but they were nothing that would have raised any eyebrows if anyone else had seen them. When she actually called me at work one morning, I was surprise, especially when she asked if I would be available later that morning. She was driving from the mountain resort where the conference had been held straight to the airport and she'd figured it out so that she could stop briefly on her way if I was available and didn't mind screwing in the car. I made sure my schedule was clear and met her outside my building when she arrived.

I hopped in the passenger seat of her rental and navigated her to a remote parking lot. We didn't have enough time or privacy to jump in the back seat and strip down, but she'd worn another sundress and told me that she'd neglected to wear anything under it. My cock was immediately on the rise as soon as she shared that with me. Once she'd parked, I had my pants and underwear down as she straddled me. My cock immediately slipped into her incredibly wet, hot pussy and we both moaned. While she started bouncing up and down rapidly on my tool, my hands were up under her dress, seeking out her boobs. With my hands on them, I was pushing up into her pussy each time she came down while caressing her hard nipples.

I really wanted to just yank the sundress up over her head so I could watch her titties bounce while squeezing her ass, but I figured this wasn't the place for that. Instead, I made out with her while fondling her titties until it seemed like she was getting close to cumming. I could feel my own orgasm welling up pretty quickly as well, in part due to her hot pussy but also in part because of the anticipation of seeing and fucking her again. I felt no need to try to hold out since our time was limited to some extent, so I was pushing up into her and pulling her down with my hands on her bare ass.

It didn't surprise me when she came first and, because her pussy got even hotter and wetter when she did, I was only a minute or so behind her. I'm not certain she'd finished cumming when I exploded into her with a groan, filling her with my load. Once we were both spent, she just sat on my lap for a few minutes as my cock started to shrink and slip out of her. She was well prepared and cleaned herself up with some tissues before slipping into the panties she had stashed nearby in the glove compartment. I knew part of that was to be a bit more modest for her flight, but she also explained that she didn't want to worry about having a big wet spot on the back of her dress by the time she returned her rental car. She slipped into her bra, as well, and all too soon she was dropping me off at my building again. We'd said our more passionate good-bye before leaving the parking lot so I just gave her a quick peck before I headed back to work and she headed for the airport.