Do You Think My Sister is Hot?

She sounded more resigned than eager but I wasn't about to let this opportunity pass me by. I grabbed the lubricant again, thoroughly coating my entire shaft and adding another small amount to my wife's puckered little opening. I then took a deep breath, touched the tip of my cock to her hole, and just slightly pushed.

Sarah moaned as the tip penetrated her tight ass. Her moan was half pain and half pleasure, I could tell. I stopped and stayed motionless for an impossibly long time as she gained comfort with the feeling of my big cock stretching her asshole.

After a very long pause, she breathed, "okay. More," and I eased myself further into her, two more inches at least. "mmmmmmmmnnnnnggghhhh" she grunted into the sheets but she was determined now, she was not about to give up, "more, Cory. More." I pushed again, inches more, and I was almost there. "Aaaaahhhh. More. Give me it all. I can take it." I pushed again, and finally felt the satisfaction of my hips against the cheeks of her ass. I was all the way in.

The sensation of my wife's soft, warm asshole grasping my cock was almost too much to bear. The extreme tightness of her opening, clenching the base of my shaft and the whole warm recesses of her bowels wrapped around my cock was like nothing I'd ever felt. It was so good, so naughty and so wonderful it took all my restraint not to fuck her frantically.

"Oh god. Oh god Cory. Oh god. Just wait. Oh my fucking god."

I didn't move a muscle. My hot wife had my cock all the way up her bum and if she didn't want me to move, I damn well was not going to move. She took some time to adjust, panting and groaning, but after a few seconds she said, "It's okay. I'm okay. It's so strange, so dirty. But Cory it's hot. It's so hot. I can't believe you're all the way in my ass."

"Ungh baby it's so tight. It feels so good. I can't believe how good your ass feels around my cock."

"Okay baby go slow. Go slow okay?"

I pulled out a few inches, ever so slowly, and then just as slowly, pushed back in.

"Oh god. Oh my god. So dirty. So good."

I pulled out and pushed in, with just a bit more force this time.

"Yes. Again."

I pulled out and pushed in, then repeated it. Sarah's asshole felt so good on the whole length of my shaft I couldn't believe it. She grunted as I pushed in with a bit more force, glad to be so thoroughly lubricated as it was definitely helping to make the experience enjoyable for us both.

"Okay. Okay," she gasped, "keep going, just not too hard." I pulled back several inches and then thrust back inside, "Unnnngh yeah. Yeah Cory. Yeah. Fuck it. Fuck my ass."

I was on fire now, from her words and from the sensations vibrating through my cock, and from thinking about the taboo and dirty act we were undertaking. I would not last long.

I began fucking her ass, not as hard as I would her pussy, but really fucking it, really pushing now.

"Yes. Yes. Yes. Fuck it. Fuck my ass. Fuck my dirty ass. Fuck my asssssssss."

I was in awe at how much pleasure she seemed to be getting from getting her butt fucked and I was about to come. As I continued sliding gently but insistently in and out of my wife's asshole, almost at a climax, Sarah looked back over her shoulder, made eye contact with me as I fucked her in her ass, and whispered,

"Hey Cory . . . do you think my sister likes it in the ass?"

That was it; I was undone. I groaned and grunted and practically howled as I thrust deep and shot rope after rope of my hot cum deep inside my wife's asshole.

...

A few weeks later, Sarah told me Megan was having a party to celebrate a recent promotion and that we were invited to her place on Friday after work.

As before, there had been no mention whatsoever of Sarah's sister except in the most mundane comments related to daily life, what she was up to, jokes she had made and how work was going. So when Sarah casually mentioned that we would be going over to her sister's house this weekend, it was not necessarily surprising, but given the role she had started to unwittingly play in our sex life, it was a bit unusual.

Nonetheless, I was eager. Sexual fantasies about Megan notwithstanding, I really did enjoy spending time with her. She was smart and charming, like her older sister, and had this warmth to her, this unspoken magnetism, that just drew you in. She worked as a manager of a very upscale, Michelin-starred restaurant downtown and at our dinners and the parties she threw, she would often hold court, regaling her guests with over-the-top stories about the excesses of the wealthy diners she served.

Megan partied a bit, which was de rigour in the restaurant business, but she had appropriately slowed down as she approached thirty and now, although her wild side wasn't far beneath the surface, she was for the most part a responsible adult who enjoyed the finer things in life. She loved to dine and drink and dance. I had to contain my excitement to spend an evening at her party.

The rest of the week passed uneventfully and on Friday, Sarah and I hurried home from work and got ready to go out. Of course, it only took me a few minutes -- guys have it easy! -- and after I had freshened up and changed I put on some music and cracked a bottle of Beaujolais, pouring a few ounces into two glasses, while I waited for Sarah.

I walked into our bedroom, and seeing the ensuite door closed and not wanting to interrupt her routine, I placed a glass of wine for her on our dresser. Sarah would notice it when she came out to get dressed and be pleasantly surprised, I thought, and I returned to the kitchen where the bass-y vibes of Frank Ocean filled the space.

I checked my phone briefly but was content to just enjoy the wine and the music and check out momentarily when Sarah emerged, holding her glass of wine and looking like a billion fucking dollars.

Her hair was up, curls cascading down around her ears. Her makeup was immaculate: smooth and subtle and inviting. And she was wearing a little black dress that would quite possibly have been illegal in several countries. Strapless, low-cut, tight and short, and she fucking owned it. The dress accentuated the lines of her exceptional forty-ish year old body and I was in absolute awe of the sexy and sophisticated woman before me, my wife of more than a decade.

Sarah looked at me, smiled, took a sip from the glass of wine she'd found on the dresser, swallowed, and said, "close your mouth, dear."

I couldn't help but laugh. This woman had such a spell on me that even after all this time she could literally drop my jaw. I rose to my feet and put my arms around her waist, running my hands over her broad, feminine hips. I leaned in to kiss her but she stopped me, saying, "don't mess up my makeup. Let's go."

...

When we arrived at Megan's condo, Sarah knocked and Megan almost immediately opened the door, then gave an excited scream, throwing her arms around Sarah's neck. "You made it!! I'm so glad. I haven't seen you for weeks!" after which she turned to me, approached me and hugged me too, saying "welcome Cory! I'm so glad you came. Come in and get a drink," with which she gave me a little peck on the cheek.

None of this was out of the ordinary of course, but given the way Megan had been factoring into our fantasy sex lives recently, between the close physical contact and the sight of her -- stunning in a tight black bodysuit and drapey white linen pants -- I was feeling a bit short of breath as we entered Megan's home. And I swear I caught a small little smirk on Sarah's face as she sensed my obvious discomfort.

Megan's party was a lot of fun. Her friends were welcoming and interesting: there is something about folks who work in the hospitality industry that makes them, well, hospitable.

Sarah and I split up for the most part, her helping Megan in the kitchen, refilling drinks and warming up appies, while I chatted with a group in the living room. We talked about work, naturally, but eventually moved on to more engaging topics like music and wine and books. One woman in particular, Jess, was captivating and interesting and we spoke for more than an hour about her work as a bartender, what she was studying in grad school, and her passion for inking graphic novels.

With this crowd almost entirely working in the same industry, I was genuinely fascinated to learn about the inner workings of restaurants: debaucherous cooks, thieving bartenders, slutty waiters and waitresses, owners embroiled in criminal enterprises; I'm sure it was all exaggerated for effect, but I enjoyed it nonetheless. I talked about my job as little as possible, as it really isn't all that interesting. That said, it pays about quadruple what anyone else in the room would make, so I was able to content myself with that knowledge.

I could tell Sarah was having a lot of fun, too. She and I were older than most of the other attendees by ten years or so . . . not so much as to not fit in, but enough to be envied for our position in life, while we envied -- or at least admired -- their relative youth.

Not to mention, Sarah was attracting a room full of male attention with her smoking hot cocktail dress. Every time she crossed the room I watched many sets of eyes following her. I was proud. The sophisticated, sexy woman attracting all the attention from these younger guys was going home with me.

Two drinks turned into four and four turned into "who's counting" and suddenly it was midnight. It's very rare that Sarah and I stay out this late, but with a room full of folks in their late twenties and early thirties, the party was still going strong. Wanting to be helpful, I gathered up a stack of dirty plates and a few empty glasses and carted them to the kitchen. Entering the small kitchen, I found Sarah and Megan chatting, each with a wine glass in hand.

"Oh hello there stranger," said Sarah lovingly, "having fun?"

"I am actually. This is a great group of people Megan. Your friends are cool."

Megan smiled, "yeah with the way Jessica Baker is looking at you I bet you're having fun you charming devil."

"Oh really," said Sarah, raising an eyebrow, "who is this Jessica and what exactly are her intentions with my man?"

"I am certain I have no idea what you're talking about," I replied coyly. "Jess is purely interested in some mentorship from someone with more life experience than her."

"Oh mentorship eh?" inquired Sarah doubtfully, "What she wants from you has been called a lot of things but 'mentorship' is a new one."

"Hey hey hey," I defended myself, "this coming from the woman in the showstopper dress who's had every man in the house drooling the whole night."

"Yeah but guess which one gets to take it off of me."

"All right, all right," groaned Megan, "I'm right here, remember? The perpetually single girl who does not need to be reminded of your bloody fulfilling and wonderful relationship. It's nauseating, really."

"Truly," replied Sarah, winking at me. "Anyway, I have to use the ladies'."

"Oh use the one off my bedroom," suggested Megan. "Too many boys have used that guest bathroom already tonight. I'll have to take the hose to it tomorrow."

"Eww. I will do that, thanks."

Sarah left, walking to the rear of Megan's condo towards her bedroom and Megan turned to me, cocked her head, cast me a sly grin and said, "so. How's things, Cory? I hear she let you put it in her butt."

I gasped and sputtered and sucked my mouthful of beer halfway into my lungs, leading to a coughing fit. Red faced I coughed and coughed for a full minute while Megan looked on with a self-satisfied expression. She let me twist in the wind, red faced and still sputtering for what felt like a very long time before continuing, "well, girls talk, you know?"

Finally catching my breath, I breathed deeply and simply said "I didn't know you and your sister talked about that sort of thing."

"Oh we talk about all kinds of stuff, Cory. Lots of stuff. Sisters love to share." She smiled at me and I was still not sure what to make of all this. Had Sarah told her about our pillow talk starring Megan? Had she told her that I find her hot and fantasize about her? No. She wouldn't. Would she? Still, I wondered about the full meaning of 'sisters love to share.'

I did recover enough to respond with, "well one thing the two of you share is how much you love making me uncomfortable, I'll give you that." This made Megan laugh out loud, which felt very nice. She had a charming laugh and was a beautiful woman, even when she was busy torturing me.

"Okay," she said, "I'll let you off the hook for now but after a few more drinks I want all the gory details. I'm supposed to be the wild child in this family, I simply cannot have my big sister doing stuff I've never done. It will not stand."

I just smiled. It was a bit surprising to me that Megan, notorious for her one-night stands and active sex life, had never done anal. What was even more surprising, though, was how revealing she was being with me.

We were all quite a few drinks in at this point so that was definitely part of the explanation, but nonetheless she and I had never had such a frank conversation. "You're right though. I really did enjoy making you squirm. You should have seen the look on your face."

"Gee thanks Megan," I said sarcastically, "I'm so glad to have provided you with some entertainment."

"Don't mention it. Now I believe it is time for a shot of tequila. Let's pour one for us and that sexy wife of yours."

"Oh god no," said Sarah, returning to the kitchen. "No shots. I'm all shotted out. Shit-shotted out. Done for. Handsome stranger, take me home, I'm drunk." She certainly looked it -- it seemed that Sarah's several glasses of wine had caught up to her all at once. She was still functional but I knew that the party was over.

Megan looked disappointed, saying "it's only just after midnight, you lightweight."

"Yeah, yeah" mumbled Sarah but she was not going to be convinced. She hugged her sister tightly and said "thanks, sis. You throw a hell of a party," and then gave her a little kiss on the cheek. It was all completely innocent but I couldn't help but find it exciting to see Sarah and Megan sharing such close contact.

"You'd better get her a tall drink of water, and I don't mean you, Cory," quipped Megan as she turned and hugged me as well.

I embraced her and it was wonderful. I am a full head taller than Sarah's petite little sister, and wrapping my arms around her back, I could immediately feel her firm breasts pressed up against my lower chest, feel her warmth through the thin, tight bodysuit, and feel the blood rushing below my belt -- I had always found Megan incredibly attractive, but ever since Sarah had introduced her into our sex life, I now was struggling to contain my desire for her.

The hug lingered a bit longer than necessary, neither one of us wanting to let go, but we finally did, and I helped my tipsy wife out of Megan's condo and down to the street, where the Uber I had ordered was already waiting.

In the Uber ride home we didn't talk much, content to hold hands and relive the fun we'd had at Megan's, until about halfway home, Sarah leaned over and whispered in my ear, quiet enough so that the Uber driver wouldn't hear, "I have good news and bad news. Which do you want first?"

"Um, the bad news please."

"I'm too tipsy for sex. I want you but it's just not going to work. Sorry."

I smiled at her and kissed her on the cheek, "of course baby, that's completely fine." Even though I had been anticipating fucking my wife silly after her sister's party, our sex life had become so hot and so good that I could hardly feel disappointment; I was a very lucky man. There were many more nights of fulfilling sex to come. "So what's the good news?"

"I'm still gonna take care of you baby."

Well this is a pleasant surprise! Although Sarah wasn't much into giving head, and so I assumed that was not in the cards tonight, as I mentioned earlier, she had recently perfected the unsung art of the hand job and so regardless I was in for a treat. Nonetheless, I was willing to let her off the hook, saying, "are you sure? You don't have to, you can just go to sleep if you like."

"Shhhhh," she slurred into my ear, "I do want to. Do you want that? Do you want me to touch your cock?"

"Oh yes baby."

"You want me to stroke this big hard cock for you?" As she said this, her right hand slid down my body, rubbing and teasing my hardening shaft through my jeans.

"Yessss."

The timing was impeccable. Just as I was starting to get uncomfortably hard, we arrived home, thanked the driver and exited the car, quickly unlocking the front door and getting settled inside. Sarah was more than a little tipsy -- we both were -- but we hadn't overdone it too much and were both just feeling pleasantly buzzed.

I undressed quickly and climbed into bed, sitting up and waiting for my wife. She did not disappoint, entering our bedroom sultrily, sitting on the bed next to me with her back to me and simply saying "unzip me."

I drew down the zipper on her tight black dress, revealing the back of her strapless, lacy black bra. She stood and, still with her back to me, slowly shimmied down the dress, tugging it over her large breasts, sliding it down over her thin waist, and then wriggling it over her broad, feminine hips. As she slid the dress down her thighs, finally dropping it in a pool around her tiny, perfect, pedicured feet, she revealed her panties, lacy and black, matching her bra, full-bottomed (Sarah doesn't like thongs and rarely wears them) and incredibly sexy, with fine lace details and sheer panels revealing the soft skin beneath them.

As I drank in the form of my wife, long smooth back, broad hips, soft round bum and long, toned legs, my right hand slid down to my shaft, lazily touching and stroking myself while enjoying the striptease in front of me.

Sarah reached behind her back and unclipped her bra, pulling the cups off of her full breasts and letting it fall to the floor. She slid her hands up and down the sides of her body, accentuating the intoxicating lines, until her thumbs hooked into the sides of her panties.

I moaned out loud as she bent at the waist, halfway to the floor, and slowly slid her panties down, over the curves of her ass, down her thighs and to the floor, taking her time and allowing me to drink in the sight of the parted cheeks of her round ass giving me a glimpse of her pussy, just disguised by a trimmed patch of curly black hairs, and above it just the slightest hint of the tight little asshole that I had deflowered not too long ago.

I was rock hard now, and full-on stroking my cock as she turned to the bed and leaned over me, her full breasts swaying invitingly near to my face.

"Do I still turn you on baby? Are you touching yourself?" she breathed.

"Why don't you find out for yourself?"

Sarah slid into the bed, both of us completely naked now, and her delicate fingers slid up my inner thigh, lingered for a moment on my sensitive balls, and then fluttered their way across my shaft, which was now hard as an iron bar.

"Oooooh is this for me?"

"You know it is baby. You're so fucking sexy."

"I'm going to make my man feel good," she whispered, fingers now encircling my shaft and stroking gently. She began a pattern of just lightly stimulating the head of my cock with her fingertips, then grasping the shaft and stroking, and then caressing my balls. It was driving me crazy. The trio of stimuli was prolonging and intensifying my pleasure.

She repeated the pattern several times, lightly on the head, lightly on my balls, firmly on my shaft until I felt my orgasm start to build.

At that moment, she started whispering in my ear, "close your eyes baby. Let me make you come. What are you thinking about?"