Shari’s Last Cherry

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I posted a story about Shari a while back. Some felt I shouldn’t have included the negative comments I made. Maybe you’re right, but it was very cathartic for me to write that story and there was a lot I didn’t say! 🙂 For those who are interested, I dated this chick, Shari, a while back. The relationship didn’t end up well, but this story is about some of the hot times we had together. I’ve classified it as erotic couplings because it’s more than just getting in her ass for the first time.

Shari 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 was fun to be around and when she wanted to, she could be a hot fuck. She loved to have her pussy eaten – evidently her first husband never liked going down on her. Well, I love to eat pussy just about as much as I love to fuck it. So, I would lick her juicy pussy for hours, sucking on her clit, licking up and down her labia, driving my tongue and then my fingers inside her. All the time she is writhing on the bed, holding my face to her pussy or holding her legs back so I can get my tongue inside her. I tried licking her ass once but she really hated that. So I concentrated on licking and playing with her pussy.

I loved making her cum. She grunted and moaned so loud. Not a screamer mind you, but you knew she was cumming and that she enjoyed it. Her pussy would get amazingly wet after she came and I would lick up her juices six ways to Sunday!

After she recovered a little, she liked for me to straddle her chest so she could give me a tit-fuck for a few minutes. Her breasts were big and soft and they felt so warm cushioning my cock while she stroked it with them. After a few minutes I would reach down and start playing with her nipples. She had very sensitive nipples and I loved to see her eyes flutter as her engine revved up again. She would look down towards my cock and open her mouth. I knew it was time. I would reluctantly pull my cock from her tit-embrace and kneel over her head, sliding my cock into her mouth. We would both moan as her mouth slid down my shaft. She loved it when I would hold her head in my hands and gently fuck her mouth. Other times I would hold still and watch as she bobbed her head up and down on my cock. I would catch her eye and then pull my cock out of her mouth. She knew what I wanted and left her mouth open and I would teabag my balls into it. She would suck lovingly on my balls and get me really hot and bothered. I would then take her mouth again with my cock, facefucking her a little more vigorously now. But she would always stop me before I came, she really didn’t like the taste or texture of cum. That was ok, by now her pussy was an inferno! I would slid my dick into her and while we kissed I would slowly fuck her pussy.

Eventually, I would kneel up between her spread thighs and really start fucking her. That usually brought a response like, “Oh yea, fuck me like you mean it!” I would start playing with her clit and she would play with her own nipples while I banged her pussy. I would shift so my cock would scrape her g-spot on every thrust. First, her eyes would roll back in her head. Then I could feel her pussy muscles start to ripple around my cock. Finally, this grunt turned into a long, low, sultry moan as she came in waves. I was either right there with her or shortly after her, pumping her pussy full of my hot cum. Like I said, there were some good times and she could be a hot fuck when she wanted to be.

So after we had been dating for a few months, she asked me if I would take a trip with her to leave the kids with her parents for a month in the summer. I said sure. I liked her kids. We got along well and had fun together. The drive went well, her kids were suprisingly good travelers. We split hotel rooms on the trip, her son stayed in my room and Shari and her daughter were in the other.

I should add here that at this point in our relationship Shari and I never had sex while the kids were there. I had not even slept over at her house while the kids were there. So to them, I was just a friend. Shari wasn’t interested in getting serious then and neither was I. We would socialize together around the kids, but only when they were visiting their father or staying with friends would Shari and I fuck.

When we got to her parent’s place, we still kept up the charade that I was just a friend, though I think her mother knew right away. We stayed there a couple of days making sure the kids were comfortable and settled. We had separate bedrooms which was fine with me because I certainly wasn’t going to fuck Shari in her parent’s house! Her dad and I became fast friends because of our mutual love of golf. So he and I hit the links everyday while Shari got reaquainted with some of her old friends.

Pretty soon it was time to go, which again was fine with me because I was starting to get very horny at this point! So with good-byes and drive safelys, Shari and started erotik film izle back home without the kids. Almost immediately our conversation turned to sex and when were we going to do it and how and how long. That was when she told me about one of her get-togethers with one of her best friends. She had told her friend all about me and about our sex life, including my preoccupation with her ass which she had been unwilling to give up yet. Shari told me that her friend had then explained all about anal intercourse giving her all sorts of tips and techniques. She said her friend didn’t exactly enjoy it, but she knew how happy it made her husband and that made it worth it. Shari said the conversation had convinced her to let me have her ass. I almost wrecked the car!

We continued to flirt the rest of the day and finally arrived at a motel for the night. I was ready to get into her ass right then and there, but Shari said she didn’t want to do it in a hotel room, she wanted to be in her own bed. I couldn’t really argue since I was going to get to take her anal cherry. Of course, at that point I would have screwed a knothole I was so randy. However, sensing that I was a little disappointed she said she would make it up to me by having hot regular sex while watching some porn so she could get to know a little more about what she was planning on letting me do. Fortunately, the motel we stayed in had several porn videos for rent. We selected one was likely to have some buttfucks in it and settled in to watch.

We laughed and giggled at some of the more ridiculous plot manipulations but Shari quieted down and started squirming when the action started. We kissed a little while sneaking peaks at blowjobs and pussy licking. When the fucking on screen actually started I began to play with her nipples and then stroke her pussy. The first scene was just a straight fuck and so we were on simmer by the time the second scene unfolded – a threesome with two guys and a girl. Shari had already indicated that this was one of her fantasies, satisfying two cocks at once. I moved down between her legs to suck her pussy while her eyes were glued to the screen. Shari would occasionally narrate the action, “She’s sucking one cock and then the other.” “Now one is fucking her pussy while she sucks the other cock.” In the meantime, I licked and sucked on her clit and tongue-fucked her pussy. She ground her pussy into my mouth while watching the action on the screen.

Suddenly she got very still. I looked up and saw her staring at the screen. “Oh fuck,” she said,”they are fucking her pussy and ass at the same time!” I glanced over my shoulder to see the woman with a glazed expression of pleasure on her face as two cocks reamed her pussy and asshole simultaneously.

“She looks like she’s enjoying it,” I said and returned to licking her pussy. I alternated sliding my first and middle finger into her very wet pussy, then slid both of them into her pussy to rub her g-spot. Shari began to moan in chorus with the woman’s moans on the screen. I slid my middle finger out of her pussy and began to tease her asshole with it. Shari gasped and instinctively tightened up. I licked her clit with broad strokes of my tongue, continuing to circle her asshole as I whispered, “Just relax, baby.”

Shari began to pant and I felt her rosebud puckering. I put my finger against it and waited. When I felt it quiver again I gently slid a little inside her ass. She let out a long low moan. I felt her asshole spasm again around my finger and then relax a little. I slid my finger in to the second knuckle. She hissed and then moaned again. She began to grind her hips up into my mouth and down onto my fingers. I looked up at her face and saw she was flushed, mouth hanging open, staring at the screen. I began to gently saw my fingers in and out of her pussy and ass while I sucked harder on her clit. Shari’s hands went to the back of my head as she ground her pussy into my face and her ass onto my finger. A steady chant of “oh fuck, oh fuck, oh fuck, oh fuck…” issued from her lips. I reached up with my free hand and began to tug on one of her nipples when she finally exploded into my mouth.

“OH SHIT!!!!” she screamed and I felt her pussy and asshole spasming on my fingers. Her pussy gushed juice into my mouth and down my hand. She bucked wildly on the bed and I tried to stay with her, sucking her clit and let her fuck herself on my fingers. Eventually she calmed down and collapsed onto the bed. At some point she had writhed away from my fingers and so now I gently blew warm air across her pussy and rubbed her mound with my hand.

“I think you liked that!” I said. Her only response was, “Holy fuck!” I snuggled up next to her, my cock now hard as a rock and craving attention, but I knew she needed time to come down a little from that orgasm. I laid gentle kisses on her pussy mound, belly and succulent tits, all the while stroking her and easing her back to earth.

“I think someone needs some attention,” she finally film izle said as I rubbed my cock against her thigh. My only response was to roll onto my back and get comfortable. I pulled her to me in a deep, passionate kiss. While battling her tongue in my mouth, I played with her nipples and she stroked my cock. She worked her way down my neck to my nipples and chewed on them while it was my turn to writhe on the bed. Then she nestled my cock between those big, soft breasts and whispered, “Don’t you dare cum yet.” I had to fight the urge because it felt sooooo damn good.

At first, Shari bypassed my cock and started licking my balls. I realized she was trying to calm me down a little so I wouldn’t shoot immediately. Mmmmm her tongue felt great on my balls. I moaned and lay back enjoying every second. She licked up from my balls to the head of my cock, repeating this action several times. I fucked my hips up into the air trying to get my cock in her mouth. “Unh, unh, unh….” she teased. “Tell me what they are doing on the screen.”

I forced myself to sit up a little and look at the movie. A new scene was now playing, just a simple twosome. As we listened to the starlets whimpers, I looked Shari in the eye and said, “He’s just fitting his cock into her ass.” Shari looked me in the eye and slowly took my cock deep into her mouth as I saw from the corner of my eye the guys cock disappear into the girl’s ass on screen. “Oh fuck….” I moaned as we listened to the sounds of the buttfuck heating up on screen and I watched Shari’s head bob up and down on my cock. Every so often she would pull my cock out of her mouth and lick the shaft and head. Sometimes she would return to licking my balls, lick up the shaft and then plunge my cock deep into her mouth. The movie forgotten, this was turning into one of the hottest blowjobs I had ever received.

Finally, I said, “If you don’t stop soon, you’re going to get a mouthful,” knowing that she did not like me to cum in her mouth. Shari didn’t say anything but returned to sucking my cock even more enthusiastically. It quickly dawned on me what she wanted and I began to let myself go to cumming in her mouth. I gently took her head in my hands and began to pump my cock into her mouth in rhythm to her sucking. “Oh Shari, oh Shari…” I murmured as I felt my orgasm welling up inside my cock. With a great shout my cum burst out in several huge spurts. Shari sucked and swallowed furiously to keep up with it. She never let go of my cock as I pumped her mouth full of cum. Finally, when I collapsed back onto the bed she let my cock pop from her mouth only to lick up and down the shaft and take the head back into her mouth as I lay helpless. It was my turn to say, “holy fuck!!”

We talked about it later when I asked her why she let me cum in her mouth. She told me it was pretty much a one time thing, that she was so hot and carried away in the moment that she wanted to do it and she though I deserved something extra special for making her cum like that. It was still something she didn’t like doing very much though, so I knew it wouldn’t happen very often. Still, I expressed my appreciation!

The next day’s travel went fine. We did a little flirting, but I think both of us were still recovering from the night before. We arrived back at her place and unpacked. I poured us each a glass of wine and then went to find her. Shari had finished unpacking and was now taking a post-trip shower. We sipped a little wine and kissed. Shari suggested I should clean up too. I joined her in the shower and we soaped and rinsed each other thoroughly. I paid very careful attention to her ass, gently washing it, making sure her little pucker was squeaky clean. I took her in my arms and kissed her as we stood beneath the spray. My hands sought out her ass and I squeezed firmly. My fingers drifted into her crack and I gently rubbed her asshole. I looked down into her eyes, “You gonna let me put my cock in there?” I whispered. She looked deeply into my eyes and nodded, “uh huh.” My cock throbbed between us.

She stepped out of the shower and told me to finish washing up. I got out to find her in the jacuzzi with candles lit all around. I settled in beside her and we sipped our wine, softly kissed, cuddled and stroked. She urged me to sit up on the side of the tub and crawled between my legs. She stroked my cock and looked at it longingly, then whispered “Oooh, you brought the big dick tonight!” I started to say it was no wonder given the anticipation, but my thoughts were cut short as she took my cock deep in her mouth. As she sucked my cock, she angled her ass so that she caught one of the jets on her pussy. She moaned and writhed against the pulsing water as she worked my cock with her mouth. Suddenly, she spasmed and moaned deeply on my cock and I knew she had had a mini-orgasm. Shari let my cock plop from her mouth and got out of the jacuzzi. We dried off and finished our wine, then she led me to the bed by my cock.

I lay her back on the bed and gently kissed seks filmi izle my way down her body, paying special attention to her oh so sensitive nipples. Soon I was between her splayed thighs licking up and down her slit until her lips parted and I wriggled my tongue inside her. She sighed softly as I ate pussy to my heart’s content. Her juices were flowing copiously by this point. I sucked them up and drove my tongue as deep as I could into her pussy and then slid a finger deep inside while I worried her clit with my tongue.

When I felt that her pussy was good and warmed up, I reached over to the nightstand and found a bottle of lube. (While I had been unpacking the car, she had been setting out the necessary equipment!) Shari watched me as I lubed up my fingers. I teased her pussy first sliding a couple of fingers inside and watching her eyes roll back into her head. Then I pushed her legs up a little to give me access to her secret hole. Shari moaned as I traced the puckered opening with a lubed finger. We both moaned as I slid my first finger deep inside her ass. Oh my! It was sooo fucking hot and tight. I felt her anal ring spasming around my finger and my cock throbbed at what it would feel like when my dick was inside her. I gently stroked my finger in and out of her asshole, marveling at the erotic sight. Then I went back to sucking on her clit while I waited for her asshole to blossom open.

I asked her if she was ok and she mumbled an assent. I sucked harder on her clit while I eased my middle finger up her ass alongside the first. Shari hissed and then I felt her asshole open up and both fingers slid inside. “That’s it baby,” I cooed, “relax and enjoy.” I left my fingers deep inside her ass and gently kissed and licked all over her pussy. Soon I felt the muscles of her asshole begin to relax and I could feel the strong pulse of her heartbeat throbbing around my fingers. I began to explore, thrusting my fingers deeper inside and slowly withdrawing. Repeating the procedure and watching her cute, little asshole dilate and receive me. I felt her asshole open even more so I applied more lube to my fingers and eased a third finger inside her hole. Shari moaned but her stretched sphincter didn’t tighten up again. She reached down to hold her legs open, giving me full access to her ass while she lay back panting on the pillows. I fucked my fingers slowly in and out of her ass, sucking hard on her clit. I felt her asshole twitch in rhythm to my tongue on her clit. “Oh baby,” she whispered, “I think I’m as open as I’m gonna get.”

I slid my fingers out of her ass and moved to lay next to her. “Get my cock ready for your ass,” I told her. She knelt beside me and sucked my cock deep into her mouth. (I must say here that it has been my experience that women suck cock differently when they are going to take it in the ass. It is hot and wet and relaxed; slow with lots of tongue and not a lot of suction. Shari proved no different, worshipping my cock with her mouth before I took her ass.) Then she sat up and put a condom on me. “Hygiene,” she softly spoke. Then she lubed up my cock and lay back down as she was before.

I knelt between her spread thighs and rubbed her pussy. I slid two lubed fingers into her pussy and stroked her g-spot until I felt her relax, then I slid a finger into her ass to make sure we had plenty of lube there. I rubbed my cock over her pussy as we stared into each others eyes. I slowly sank my cock into her overheated, relaxed pussy and we moaned together. I fucked her gently for a few minutes and bent down to kiss her deeply. She sucked hard on my tongue. I pulled back and disengaged my cock from her sweet pussy. “Ready?” I whispered. She nodded. I pushed her legs back exposing her now lubed asshole. It was shiny and red from the play earlier. I lined up my cockhead with the puckered opening. I could feel it twitch through the condom. “Relax, baby, let me in,” I said. She nodded and closed her eyes. I pushed gently and the head of my cock started to push into her ass. She gasped and it slipped out and plunged back into her pussy. We enjoyed that feeling for a minute and then tried again but my cock again slipped up into her pussy.

“Hold your legs open for me baby,” I said and she reached down and pulled herself open for me, offering me her ass. Now I was able to hold my cock steady as I directed it against her hole one more time. This time we both gasped as the head started inside. I held still and sure enough Shari was able to start to relax and my cock moved further inside her ass. Shari looked up at me, eyes wide, panting and I slowly pushed my cock deeper into her ass. Incoherent sounds were coming out of her mouth as I held still and waited for her ass to open like it did for my fingers. I told her to take deep breaths and after three or four I started to gently thrust in her ass. Her eyes closed and she moaned deep in her throat. I took that as my cue and slid my cock the rest of the way home, balls deep in her ass. I felt her sphincter squeezing the base of my cock. It was soo damn amazingly tight and hot in her asshole. I bent down to kiss her. Then, forehead to forehead, I whispered, “oh baby, I’m in your ass. You gave my your asshole. It feels so damned good! You okay?”

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