Shari Takes It Up The Ass

A while back, I dated this woman, Shari, for a while. She was in her 30s, divorced with a couple of kids. She wasn't beautiful, but she was attractive. She had a Rubenesque figure, with big, round breasts and a nice full ass. Shari had a wicked sense of humor - you know the type, she could skewer anybody's neuroses, although that's what drove us apart later when I was constantly on the recieving end. Sexually, she was pretty hot. We had fun in bed, not particularly adventurous, but she loved to get fucked. About the only things she didn't really like were swallowing cum and anal sex, but you wouldn't guess that from the story I'm about to tell!

She had big, soft, pillowy boobs. Because of the kids she had those post-nursing nipples, you know, with huge, dark areoles and long, thick, very sensitive nipples. She loved it when I rolled them between my fingers while I sucked her clit; it made her hump my face. But I think her favorite was to ride me cowgirl, hang those beauties in my face and have me bite and suck them. You would have thought she was riding a wild bronco the way she screamed and pounded her pussy on my cock. Speaking of her pussy, again because of the kids she wasn't the tightest girl I've ever been with, but she had one of the hottest pussies I've ever felt and she was constantly wet. No matter when or where I reached into her panties or under her dress, that woman was always wet and my fingers just slid inside.

We had been dating for a couple of years and things had started to get a little stale. She never seemed much in the mood for sex anymore. She had started to turn her wisecracks on me, especially when we were out with friends. And on this one night it was particularly humiliating. We were out with another couple - Linda and Tom - and things seemed to be going well. We were laughing and talking and just having a grand time knocking back a few drinks. Somehow the conversation turned to sex and porn. Linda made some comment about lesbian videos turning Tom on. We both looked at each other and deadpanned: "There ain't nothing wrong with being a lesbian!" We all had a good laugh over that, but the laughter had barely died when Shari said, "Oh that's nothing. You should see all the gay porn Will keeps in his stash."

The table went silent. Linda's jaw just about hit the floor. Tom looked like he wanted to crawl in a hole and I'm sure my face was beet red. I had no idea of where this was coming from. She had never mentioned this before. I was totally blindsided and humiliated in front of our friends. I tried to chuckle and save some dignity. "Oh Shari, you know I only keep that because it gets you all horny."

"Yeah, right" she replied.

We tried to laugh, managed a few uncomfortable chuckles. Linda even tried to change the subject, but the evening was now DOA. Tom relieved us all when he said, "Well, we gotta get going. It was great seeing you guys, hope we can do it again soon." (Yeah,not! I thought)

I was furious. Shari knew better than to speak to me on the way out. We drove in silence most of the way home. She tried to speak once or twice. "I don't know why I said that."

Through clenched teeth, the only thing I could reply was "Just don't talk to me right now."

We got to her house and she pleaded, "Please come in and let's talk about this. I'm sorry."

"I can't talk right now. I need some time and some distance. I don't know what possessed you to say that, but I have given you no reason to humiliate me like that. I need to do some serious evaluating of where this is going and I need to do it alone."

I told her I would let her know when I wanted to see her again and drove off.

Over the next few days I was able to let a lot of my anger go. I mean, I knew Linda and Tom would probably laugh it off if they even remembered it in a month or so. I was more upset about why she wanted to hurt me and I began to think about ways to make myself less vulnerable.

I had several emails from Shari which I ignored, she knew better than to call and leave a message. Finally, about two weeks later I opened one of the emails: Please call me. I am so sorry. I want to apologize and I want to do something to make it up to you. Shari

I'm not sure what made me decide to call her that night, but she sounded so relieved when she heard my voice.

"I'm so glad you decided to call me. You don't know how sorry I am for hurting you like that. I know I can't take it back. I also know I've been a real bitch lately and I don't know why I took it out on you. Listen, baby (she always called me baby when she was horny, that made my ears and my cock take notice!) I sent the kids to Mom's this weekend. If you come over, I'll show you how sorry I am and give you a weekend you'll never foget!"

I know, I know. I was thinking with my dick. But sex with Shari was hot and it had been two weeks. I tried to sound still put out when I told her I'd be over around 7.

I took my time getting cleaned up and ready. Popped a little blue pill and washed it down with some Scotch. I got to Shari's house a little after 7. Through the storm door I could see that the front door was open. I walked inside and found a note on the coffee table: Pour yourself a drink and come on upstairs when you're ready. S

There was a tray on the table with a bottle of Ouzo and two glasses. I could see that one glass had already been used. I smiled and my dick twitched. Ouzo made us both crazy in bed. This was promising. I downed a shot quickly - hopa! I thought to myself. I savored the burn and the anise filling my nostrils. I poured another and sipped as I closed and locked the front door, turned down the lights and put my coat away. I refilled my glass one more time and poured one for her as I headed upstairs unbuttoning my shirt on the way. About halfway up, I heard her crank up Symphony X "Absinthe and Rue" on the CD player. The wilder the music, the wilder the sex with Shari. This was definitely going to be good!

I walked into the bedroom lit by a dozen or so candles. Shari was standing naked, next to the bed. She was wearing a pair of padded cuffs linked by a chain and holding a blindfold. She stared at the floor as I walked up and took her heavy breasts in my hands. Her eyes fluttered as I tweaked her nipples. I kissed her and she kissed me back hard pushing her tongue into my mouth. I tasted the ouzo on her tongue, her breath was warm, sweet and anisey. My right hand left her nipple and reached between her legs. Yup! Soaking wet. She moaned into my mouth as I slipped two fingers up inside her. My cock was making a tent in my pants as I stepped back to look at her. Her eyes were glazed with lust: her face was flushed, her nipples erect. You could smell her arousal across the room. She looked me in the eye. I glanced down at the cuffs and back up.

"You understand what this means?" I asked. She nodded and dropped her eyes, her face in full blush.

We had talked about light bondage before. She said she wasn't entirely comfortable with it because she felt she should be ready to give up control, to do anything I wanted without being able to say no.

"Anything?" I asked. "Anything." She said without lifting her eyes.

I took the blindfold from her and as I positioned it over her eyes I whispered in her ear, "Potato." A safe word.

She trembled as I stepped away from her and began to undress. I sipped my ouzo as I walked around her, admiring her from all angles. A naked woman is even more arousing by candlelight. On the nightstand I spotted a bottle of lube and a set of nipple clips. My god, she really did mean "anything!"

I picked up the clips and walked back in front of her. I kissed her lightly and she tried to seek out my mouth. I dipped my fingers in my glass and brought them to her lips. She licked and sucked hard on my fingertips, savoring the flavor. I offered her her shot glass and she gulped it down. I teased her mouth with my lips and tongue while I brought her nipples to full flower with my fingers. I kissed her hard on the mouth and fastened one clip onto her right nipple. She moaned deeply into my mouth and tried to hump my leg with her pussy. Still kissing her, I attached the other clip to her left nipple. She whined a little as I tugged on the chain and broke our kiss. Guiding her head by tugging on the chain, I brought her mouth to my own nipples. She knew how much I love to have my nipples sucked and she went to town, licking, sucking, nibbling. Her cuffed hands found my belt and began to undo my pants trying to find my cock.

I stopped her and made her stand still. I kissed her once more and then admired her body. I hefted her breasts and let them drop. She grunted as the clips bounced. I ran my fingers through her slick slit and she trembled with desire. I walked behind her, squeezing her ass, running my finger between her cheeks to find her asshole. I gently circled her anus with one finger while my other hand found her clit. I rubbed in rhythm until she began to pant. I stepped away as she humped the empty air. I stepped closer again and nibbled her ear as I told her, "You look beautiful."

I finished undressing and led her by the chain of the nipple clips to the loveseat in her bedroom. I sat down, legs spread and tugged on her nipple chain. "Kneel."

She knelt between my legs. I reached down to fondle her breasts making her gasp with each movement of the clips. I guided her head with one hand and held my cock steady with the other. "Suck my cock."

She opened her mouth and took my cock in. She immediately began to suck hungrily. She moaned and whimpered as she bobbed her head up and down my rock-hard cock, each stroke causing her tits to sway and the clips to torture her nipples. I moaned and lay back, enjoying how her mouth and tongue made me feel. I finished my drink and set the glass down. The CD was now playing "Shades of Grey."I looked down to watch Shari's lips around my cock, watching it disappear into her mouth. I moaned as it hit the back of her throat and she fucked her face on my dick. I pulled her face off my cock. Her mouth gaped open as she tried to find it and get it back in. I slapped her on the cheek with my cock but pulled it away from her whenever she tried to take it back in her mouth. She got the hint and let me rub my cock on her face. I pushed her head lower and she began to lick and suck my balls.

I lifted my feet off the floor and put them on her shoulders while she went to town munching my balls. "Oh my god, that feels so good!" I moaned while her tongue laved up and down my ball sac. She took each one gently into her mouth and sucked. Then she kissed them both and licked some more. She knew how much I loved to be licked down there and she made sure I got what I wanted. As I said earlier, one of the things Shari didn't like was swallowing. She didn't mind me shooting on her face, so she would usually lick my balls as I came. Tonight was different though. Tonight she would do anything.

I coaxed her back up to my cock. She licked up and down the shaft. She nibbled my cock and licked the head before taking it deep in her mouth. She was moaning now as she worked my cock slowly in and out of her mouth. I was so hard I thought my dick was going to burst. This was an amazing blowjob! I took her head in my hands and began to gently fuck her mouth. I looked down to watch my cock as I pumped it in and out, the blindfold made it even hotter. She was drooling hard trying to keep up as I thrust faster. "Oh baby, I'm gonna cum in your mouth!" I cried. She whimpered and then began to suck even harder.

I held her head still as my cock started to spasm. I thrust in and out of her mouth in time to my spurts of cum. Shari gasped a little at first but then began to suck and swallow trying to keep up. I pumped a huge load in her throat and she swallowed every drop. I lay back, exhausted for the moment and she slowly cleaned up my cock with her mouth. She sucked it dry and lifted her mouth off me, "I love your cock!" she whispered and then took it deep in her throat again.

Between Shari's sucking and the magic little blue pill I was still hard as a rock, but I needed a bit of a break. I pulled her mouth off my cock with a "pop" and had her lean back on her knees. I reached down to take the nipple clips off. She gasped and cried out when I did, so I kissed her hard on the mouth tasting my own spooge mixed with a hint of ouzo. I gently rubbed her boobs getting some blood back into her nipples and easing the ache.

I helped her stand and move to the bed. I laid her on her back first and attached the cuffs to the headboard. I knew she loved my tongue so I asked her what she wanted. "Oh please baby, please lick me goood!" she whimpered.

Always wanting to please a lady, I pushed her legs back and dove face first into her sopping wet pussy. If she was wet before we started, it was now a swamp between her legs. Obviously, she had really gotten off on what we were doing so far. That made me even hotter, if such a thing were possible! I kissed and licked and sucked on her outer lips making her squirm and moan. I ran my tongue through her lips teasing her clit and her vaginal opening. She tried to hump my face. I used my fingers to open up her pussy lips and blew warm air over her clit. That got her! "Pleeeeaaaassse!" she whimpered.

I relented and began to lick her clit. She grunted and then moaned, "oh... fuck yes!"

I licked and nibbled her clit while her hips trembled under my assault. I slid a finger deep in her pussy as I sucked her clit. She hissed and began chanting "oh... oh... oh... ohh... ooooh..." The fingers of my other hand found her asshole and rubbed in counterpoint. Shari's hips began a crazy rhythm of seeking out each sensation - humping my tongue, then wriggling down to get my fingers deeper in her pussy and finally pressing her ass onto my fingers. Her mutterings became an incoherent "unh, unh, unh, unh..."

I slowly began to ease off, I didn't want her to cum yet. She realized what was happening and began to whine.... "Nooooooo!" But I stopped my oral assault and just let my fingers keep her thermostat on simmer. I felt her relax and begin to grind more into my finger tapping on her backdoor.

"Get on your hands and knees."

Shari rolled over as best she could with the cuffs still attached to the head board. She lowered her face to the mattress and stuck her ass up in the air offering me her forbidden opening. I reached over and grabbed the lube. Squirting some onto my fingers and her ass, I began to rub it in. I gently circled her anus with a lubed fingertip as I talked gently to her..."Yea, that's it baby. Open up for me. Give me your asss!"

She moaned as my finger slid inside her tight hole, then whimpered as I began to fingerfuck her ass. My cock was now ready for more attention, so I lubed myself up and slipped my cock into her now steaming pussy. Shari groaned loudly as fucked her pussy and teased her asshole. She grunted when I eased a second finger into her ass and then moaned with each thrust I made into her juicy pussy. "Unh, unh, unh, unh... that feels sooooo fucking good" she whispered as I pumped both her holes.

I eased my fingers out of her ass and my cock from her pussy. I watched her asshole wink at me and close up as I moved my cock into position. I squirted more lube over both of us and began a gentle circular motion with my cockhead on her asshole. I felt her stiffen and heard her grab the chains on the cuffs as I teased her tight opening. "Relax baby. Open up and let me in. Show me you want my cock in your ass."

I centered my cock on her asshole and pushed gently. I felt the muscle begin to give, the incredible heat of her ass on my cockhead. I heard her gasp, her head coming up off the mattress when I popped inside. "Easy, baby, easy" I soothed as I rubbed her back and hips allowing her to get used to the intruder in her ass. I felt her anal ring spasming around my cockhead as she struggled to relax and let me in.

With a deep moan, Shari's head dropped back onto the bed, her asshole blossomed and my cock sank deep inside her. I slowly pushed until I could feel her anus wrapped around the base of my cock. "I'm all the way up your ass, baby" I whispered. She gave a low grunt in reply.

I waited a while before I began to move, relishing the incredibly tight heat of her anal glove. My cock throbbed in her ass waiting to ravish it. I gently ground my hips into hers until I felt her asshole begin to relax a little more. As I eased my cock back a little, Shari hissed. When I pushed back in she moaned. I enjoyed these sounds and sensations as "Rapture or Pain" blared on the CD. When Shari began to push her ass back onto my cock, I started to fuck her.

I reached down and spread her cheeks to watch my cock disappear into her ass. It was so erotic to see her asshole stretch around my dick as I sawed in and out between her cheeks. I loved the slick slurping sound her asshole made around my cock. The feel, the sight and the sound of her ass was incredible as I fucked her. I was thrusting harder when her head came up again and she began to pant and mew. My cock was so fucking hard as I felt every spasm and twitch of her anal ring around my cock. Her asshole felt like molten velvet on the inside. I grabbed onto her her hips and pounded harder inside of her as she opened up her ass and cried "Yes... Yes... Yes.... YESSSS!"

"I'm cumming up your ass!" I shouted as my cock exploded inside her. "Unh, unh, unh, unh, unh.... oh FUCK yea!!!!"

I thought I had cum big before when I shot off in her mouth, but that was nothing compared to what I felt now. I thought the head of my dick was going to split open I shot so hard and so long up her ass. I just kept pumping away it felt so fucking good. The blood was roaring in my ears so I have no idea if she made any sounds at all. My entire body turned into the cock I had buried up her sweet ass.

I collapsed onto her back for a while until I could get my breath back. We were both soaked with sweat and lube. I could feel her anal ring trembling around my cock and my slime starting to ooze out of her violated ass. I finally eased my cock out of her and stepped back to view my handy work.

Her asshole was red and swollen. It gaped open a little bit and my white cream slowly bubbled out. Shari's pussy was opening and dripping wet. It looked like she might have squirted in the middle of our rut because there was a huge wet spot beneath her and drops of pussy juice on her thighs.

Somewhat exhausted Shari rolled to her back on the bed. I knelt between her thighs and gently stroked her clit. "Wanna cum?" I asked.

She could only nod. I gently rubbed her clit and watched her asshole spasm and spit out more of my jizz. I moved my fingers down and slipped two into her pussy. Oh my god, she was a seething fucking furnace in there. Her pussy was sooo fucking hot and wet! I squished my fingers inside her. "I think you liked getting your ass fucked!" I said. She just whimpered and thrust back onto my hand.

I added another finger and began to stroke her g-spot. Her breathing was getting ragged. I started to tease her cervix with my middle finger. I felt her pussy walls begin to ripple and she pulled her legs up so I could get deeper.

We had talked about fisting. Since she wasn't really tight anymore from the kids, she enjoyed being stretched open. Sometimes while going down on her I had managed to get four fingers up her to the palm, but she was afraid to try the fist thinking it would hurt or that she wouldn't be able to take a regular cock in more. She seemed oblivious to all those concerns this night. I eased four fingers up her and she just moaned louder. I twisted my fingers around inside her, massaging her walls, opening her up. She spread her legs more to give me a better angle. I grabbed the lube, squirted a ton on my hand and then used my hand like a funnel to pour some inside her. I brought my thumb together with my other fingers like a cone and started easing it up her. Shari's pussy was opening up and stretching to let me in. Shari was moaning and panting as I worked for the best angle for my fist to enter her. I felt her pussy walls ripple beneath my fingers, she took a deep breath and pushed her fuck tunnel onto my hand. I flattened my fingers as best I could and held my wrist steady, not really pushing, just sort of bearing down. I felt her pussy walls open up and watched as my hand slipped all the way inside her. Shari cried out loud and shouted something incoherent when my fist went in. It was so amazing to feel her pussy from the inside. I felt all her muscles as they spasmed around my hand, this electricity just shot up my arm. I gathered my fingers into a fist and just let her pussy do the work.