Her Tight Anal RingI recently started baby-sitting in order to help pay for my college expenses and I must say the experience was more than a little exciting. While I was in high school I babysat but I never had any sexual experiences with any of the families I sat for, but now about every third client I have seems to want to bed me and more than a few are single women who want to have a safe no strings attached tryst with another woman. Before I get too far ahead of myself I should tell you about how it all started. Being in college was putting a real strain on my finances and I determined I would have to supplement the money I got in grants and aid in order to make end meet when my roommate suggested I fall back on the old baby-sitting standby. While I was not crazy about this idea I figured what the hell at least its money in my hand so I wrote out an add and went to the local supermarkets and posted it on their bulletin boards. Well the response was overwhelming and I soon had more than enough work to keep me busy. One couple with 2 kids I'll call them Ken and Lisa were very nice although a little nonconformist. The first time I worked for them they went out and Ken returned home not with Lisa but with another woman. I asked no questions but by the way they were all over each other I figured that Ken and Lisa must be into the swinging life. Their kids were pleasant enough and the money was good so I continued to sit for them on a regular basis. One day I got a call from Lisa early in the morning asking if I could come over about ten o'clock and stay with the children until 4:00 as she had to go out that day. As I had only one class that day I agreed to sit for her. When I arrived Lisa was still in the shower so I went around back by the pool and let myself in. I checked on the kids and found them watching TV in the rec room then set out to find Lisa and check in. I walked into Lisa's bedroom and found her standing there stark naked. I excused myself and started to leave but Lisa called me back saying that it was ok and that she wasn't a prude about nudity. I watched as she got ready to go out and as I did I felt my pussy getting wet and my nipples started to harden. Since I was dressed only in my cutoffs and a T-shirt my excitement was obvious to Lisa and she watched me closely as she began to get ready. Lisa is an beautiful red head and she stands about 5' 10" with firm creamy tits a hard taught belly and nice pink nipples which stand out proudly when excited. Lisa's legs are long and firm and her pussy was partly shaved exposing her full pink pussy lips. I could tell Lisa was getting turned on by the situation as her nipples were fully erect and a light flush had appeared on her upper chest. Lisa moved to her dresser and took some body lotion and began to rub some of the fragrant lotion into her full firm tits rolling her erect nipples in the process. Lisa finished up by rubbing the excess into her exposed cunt lips and in the process exposing her hard long clit. All the while Lisa was getting ready she kept up a steady stream of conversation which I barley heard as my eyes and thoughts were glued on her fantastic body. Lisa went to her dressing table and got out a black garter belt and shear stockings and slowly put them on. She still wore no panties or bra. She then put on a shear blouse which barely covered her ample tits and slipped on a skirt commenting that she hated wearing underwear and found going without it was much more comfortable and a bit naughty. Lisa asked me if I was wearing any and I replied only my panties to which she suggested I go without them in the future and give myself a thrill. Lisa came over and gave me a parting hug which was more than friendly and said she would be back by 4:00 and to make myself at home as her husband Ken wouldn't be back until very late that evening. The rest of the day went slowly and I continued to have fantasies about Lisa seeing her beautiful body in my mind as my imagination slipped from one forbidden fantasy to the next. Lisa's kids were good and the time passed quickly with my mind filled with potential lust filled adventures. Its funny I never really got turned on by women as a rule but there have been a couple of times in my life when I spent some idle hours in between the sheets and thighs of one of my female friends mostly out of lack of any nice guys, but my desire for Lisa was something else again. As per Lisa's schedule I put the kids down for their nap at 1:00 right after their lunch. Having some free time and feeling very stimulated from all the fantasies that were running through my head I decided to go out and sit by the pool and relax in the sun. Knowing there was no one around and having noticed that the back yard area was ringed by high walls I decided to take off my panties and see if Lisa was right. As I removed my cutoffs I knew I was very stimulated as the entire crotch of my skimpy white panties was soaked with my pussy juices. I pulled off my panties and stood there in front of Lisa's bedroom mirror as I slowly rubbed my slick pussy and pressed my hard clit between my wet labia. It felt great but I was getting carried away so I put my shorts back on and went out to the pool area and layed down on one of the lounge chairs soaking in the warm sun.
I was feeling very sexy and spread my legs as if to allow some unseen admirer to peak up the leg of my cutoffs and watch my cunt. In my minds eye my admirer was Lisa and I could see her licking her lips with anticipation. Lost in my daydream I started to squeeze my tits and pull my now erect nipples making me very hot. I pulled up my T-shirt and really gave my tities a workout as my hand went between my legs and stroked my pussy. Soon I was having my first orgasm my fingers pumped fully up my soaking twat as I viciously frigged my clit with my thumb and worked my now swollen tits with my other hand. As I descended from the heights of my climax I sensed that I was not alone and opened my eyes to see Lisa sitting opposite me watching my self fulfillment with obvious lust. I was shocked at first and covered up and told her I was sorry but the sun had relaxed and excited me and well I just lost control. Lisa told me not to worry about it that she often came out here to sun and it many times had the same affect on her. Lisa asked me if her suggestion that I not wear panties had helped get me worked up and I told her it had and that I had taken them off just before coming out to relax. Lisa told me her business in town had concluded early and she decided to return home and relax with a swim. I told Lisa that sounded great an I envied her. Lisa came back by asking me if I wanted to join her in the pool and spend the afternoon with her. I somehow knew there was more in her invitation than was spoken and told her I would like to but I had no suit and no change of cloths. Lisa stood up and removed the robe she was wearing and told me I really didn't need one showing me her firm naked body and telling me to swim like she did, naked. I a flicker of uncertainty flew through my head but was soon replaced with desire and I thanked her and told her I would enjoy that very much. Lisa told me to take off my cloths and meet her in the pool. I watched as she dove into the pool and surfaced calling me to join her. I pulled off my T-shirt exposing my firm full breasts to Lisa's view, my nipples were fully erect and I knew from Lisa's expression she was appreciating the show. Next I pulled my shorts down and since I had taken off my panties earlier I was completely naked. I couldn't hide my lust for this woman and I briefly rubbed my mound slipping my finger over my clit. Moving to the edge of the pool I prepared to dive in letting Lisa have a long look at my full tits and firm hard body hoping I was having the same effect on her as she was having on me. I dove in and swam around a bit the water was really refreshing and Lisa and I exchanged some girl talk as we discussed the problems in each of our day to day lives. Pretty soon we were into some intimate conversation concerning our sex lives and I learned that Lisa and her husband Ken were as I suspected into swinging and enjoyed sharing each other with their friends. This talk was getting me hot and as Lisa and I sat on the edge of the pool I could feel the heat and wetness build up in my pussy. When Lisa put her arm around my shoulders I thought I would melt and I leaned into her and kissed her full warm lips. Lisa was a expert seductress she softly caressed my shoulders with her hand as she cupped my breast and fondled me to a frenzy. Out tongues exlored each others mouths as I reached for and found her full firm tits cupping them and fondling her in return. Lisa layed me back and began to rub my hard flat belly as she stroked the insides of my thighs with her other hand, moving ever closer to my now sopping pussy. I could feel her light touch on my cunt lips as her fingers gently massaged my outer lips pushing them back to expose my now throbbing erect clit. I drew in my breath as Lisa descended on my cunt spreading my legs and opening my pussy as she slowly ran her tongue over my open lips and then found my hard button. Her licking soon turned to sucking and I felt her push two of her long fingers into my pulsing cunt as she sucked my clit until I climaxed. As I was coming down from my orgasm Lisa crawled up on me and licked my nipples and then kissed me again letting me taste my pussy juices which covered her mouth and lips with a fine sheen. I wanted to pleasure her so I told her to lay back and let me return the favor. I pushed Lisa on her back and reached between her legs spreading them and giving me access to her slippery shaved cunt lips. Pressing my fingers deeply into her hot slippery pussy I began to rub her clit with my thumb as I sucked her tits and bit her nipples. This had Lisa moaning in no time and I could feel the walls of her vagina pulse with each thrust of my probing fingers. I moved slowly down Lisa's hard taught belly until my mouth was positioned right in front of her sopping pussy lips. Lisa could hardly contain her passion and quickly placed her hand at the back of my head urging me to suck and lick her slick cunt. I reached out my long tongue and licked her shaved pink lips separating them from around her already stiff distended clit and began to flick her hard button with long tantalizing strokes. As I licked I continued to play with her tits and rolled her right nipple between my thumb and forefinger as I pushed and probed her hot twat with my invading fingers. About two minutes of this had Lisa quaking with orgasm and I licked up the overflow of her sweet juices like a bee in a flower as she poured out her passion. As Lisa was recovering I moved back up to her face and kissed her deeply probing her mouth with my tongue and letting her taste her own juices. After Lisa had regained some of her composure she suggested we go into the house and see if the children were still sleeping and then continue our lovemaking in her bedroom. I could hardly wait to get into her arms again and told her that while I infrequently had quick one time experiences with other women during my life none of my previous lady lovers had made me feel as good as she did. We walked back into the house hand in hand and I began to feel very close to her. After checking on the children Lisa and I went to her bedroom and after a bit of mutual caressing and fondling Lisa asked me if she could shave my pussy so that I could get the full benefit of her mouth and tongue work while we made love. At this point I could refuse her nothing and readily agreed. Lisa took me into the master bathroom and had me sit on the edge of the vanity while she prepared to shave my pussy. I told her I wanted mine to look like hers with a smallish tuft of hair left on my mound and my cunt lips fully shaved and exposed to view. Lisa relished her work and quickly shaved me cleaning off my sensitive lips and then turning me over and shaving a few stray hairs from around my anus. I was pleased with her work and told her it felt like I had a whole new cunt to experience her love with. Lisa answered by slowly pressing her index finger up my virgin anus and telling me that my pussy wasn't the only place to feel pleasure and as she deftly worked her finger up my ass I knew I was about to broaden my sexual awareness quotient by at least 100 per cent. I suggested we shower and then I would like to eat her pussy again, an idea that made Lisa very happy and we proceeded to shower together making sure to rub all the sensitive parts of each other. I even managed to fuck her anus with my finger as I washed her ass and fondled her firm ass cheeks. Lisa's touch on my now shaved pussy made me quiver with delight as each touch felt like a thousand feathers caressing my naked cunt. We returned to the bedroom and Lisa asked me to get on the bed which I gladly did as she went to her dresser and opened the drawer and began to take out her toys as she called them. Now I have a little plastic friend at home in my dorm room which I use regularly to relieve my sexual tension but compared to what Lisa had in her drawer my vibrator and I were clearly novices. Lisa pulled out a 18 inch double dildo which she said we'd share later and then two different vibrators one about 8 inches in size and quite thin and another about a foot long that was jet black, I guessed this one was to simulate a big black penis. Lisa also removed a good sized dildo attached to some straps and I knew from watching some porno tapes with my boyfriend that I would be feeling this monster in my pussy soon. Lisa brought her collection over to the bed and asked me to get up on my hands and knees facing her. She then slid beneath me and after sucking my full swinging tits and chewing on my sensitive nipples she wormed her way back until he mouth was directly under my cunt. I was looking directly in her sweet cunny and I could tell from the wet river pouring out of her pussy that she was very turned on. I kissed her sweet pussy and pushed my tongue into her wet hole as she pulled my pussy to her mouth and began to tongue fuck my newly shorn cunt. I spread her swollen pink lips and inserted two fingers up her hot wet channel making her moan audibly in the process. I switched my tongue to her clit and licked her erect love bud with long slow strokes as I probed her hot wet hole with deep hard strokes. Lisa pulled my cunt lips back and reached around my hip grabbing my ass cheek and spreading the crack of my ass. Just as I wondered what she was going to do I felt her hot wet tongue enter the puckered ring of my asshole and I started to shake with excitement. Lisa slowly tongue fucked my anus until I climaxed while she continued to finger fuck my cunt and frigged my hard clit with her thumb. I was devastated by the intensity of my climax and determined to brig Lisa off the same way. Pulling her legs back under my arms I exposed her pink puckered asshole and immediately began to run my tongue over her pulsing asshole. I could tell Lisa needed more and I pushed three fingers up her sopping cunt and started to rub her clit in time to my pumping fingers. Lisa was moaning loudly by now and I pushed at her tight anal ring with my tongue until it opened up a bit allowing me to penetrate her tight asshole. I continued my assault on her anus cunt and clit until I felt her climax peak and begin to subside. I had never experienced a woman so fully as I had Lisa just then and could not get over the intensity of our pleasure. After a bit I climbed off Lisa and snuggled up next to her kissing her and fondling her cunt ass and tits. Just as we were returning to earth from our out of this world experience I heard the children begin to make noise. I told Lisa to rest and I would take care of them and get them down stairs and settled in front of the TV. As I left Lisa call to me to hurry and she would have a surprise for me when I returned. I left thinking of how much pleasure we had enjoyed and thought it would be hard to top our previous lovemaking. I returned after settling the kids to find Lisa kneeling on the bed with the strap on dildo on and pumping the big black vibrator in to her sweet pink pussy. I watched as Lisa rammed the vibrator up her cunt and stroked the long strap on dildo at the same time. Lisa called me to the bed and I dropped the robe I had put on to the floor and presented her with my cunt and ass doggy style. Lisa bent down and began to lick and suck my pussy as she continued to ream herself with the vibrator until she had me on the verge of orgasm. She then move in on my cunt with that long stiff artificial cock and slowly pressed its length into my waiting pussy I thought that plastic shaft would never end as it stretched my cunt to the limit making me go crazy with pleasure. Lisa obviously an old hand at this had no trouble fucking me with her artificial cock while she continued to do herself with the dildo and I imagined seeing that fat black shaft being repeatedly rammed into her pink shave pussy as she probed my own stretched hole with her plastic penis. In no time she had me moaning in orgasm and I fell forward and watched as she stroked her fake prick and rammed her cunt with the black vibrator until she too collapsed in orgasm. Seeing her their defenseless the black shaft still protruding from her pink swollen cunt lips I moved in between her legs and pulled off the strap on dildo and slowly stroked the vibrator in and out of her steamy cunt as I licked her clit. This aroused Lisa once more and I pushed my finger deep into her anus as she squirmed in pleasure. Lisa climaxed again as I licked and sucked her sweet clit and pounded both her holes with a quick hard rhythm. Lisa quickly regained her strength quickly and crawled up between my thighs and began to lick my clit while she probed my hot cunt with her big black vibrator and finger fucked my asshole. I was so worked up I climaxed quickly thrusting my slippery lips into Lisa's mouth as she impaled my pussy on that demon vibrator of hers. As I was lying there panting from my last orgasm the big black vibrator still humming in my fuck happy twat Lisa got her other vibrator and wet it by forcing the entire shaft up her juicy pussy. Rolling me on my side Lisa spread my ass cheeks and slowly worked the vibrator into my anus. Since my ass was still a bit virginal Lisa slowly worked in that throbbing monster until I was able to take the entire length up my throbbing anus. I had never felt so full before and I climaxed over and over as Lisa worked her toys in and out of my cunt and asshole while she sucked my tits and bit on my nipples. As both of us were just a bit fucked out Lisa suggested we check on the kids and then take a nap before dinner which sounded good to me so I went down and made sure the children were ok then joined Lisa for a shower and we crawled onto her bed and fell asleep in each others arms. I woke before Lisa and after checking on the kids again went back to her bedroom and woke her up by licking her cunt and asshole until she was well stimulated. Teasing her I suggested we make dinner and get the kids to bed early so that we could have some more time to ourselves. Lisa thought that it was a good idea and we proceeded to dress and get dinner ready. After the kids went to bed Lisa asked me if I would like to see some porno movies she and Ken had. My pussy was wet and I was ready for anything so I told her yes and Lisa went to the VCR and popped in a tape, as the movie started I realized that this was not a commercial tape but rather a home grown video that someone had made. As the movie started there were a bunch of people at what appeared to be a party they were all milling around and engaged in conversation. Then the camera focused in on one woman and it was Lisa she was standing talking to this man and woman and was rubbing this guys cock as she talked. The woman was just watching and listening like there was nothing unusual about Lisa's behavior. Lisa then unzipped his fly and pulled out his long cock and began to stroke it. The woman now reached over and began to squeeze and fondle Lisa's tits as Lisa brought the guy's cock to full erection. Once Lisa had the guy fully erect she handed the woman her drink and got on her knees taking the guys cock in her mouth. This guys cock must have been at least 10 inches long and as fat around as I have ever seen. After a few good licks Lisa had his cock fully in her mouth and throat with his balls were resting on her chin. The other woman just watched until she too decided to get into the action. She unzipped her dress and took it off revealing her big firm tits and large stiff nipples and she was wearing only a garter belt and nylons so her cunt and ass were fully exposed. She reached down and helped Lisa get undressed until Lisa had nothing on at all. By this time I was already rubbing my tits and twisting my erect nipples in anticipation of what was going to follow. Lisa suggested we strip each other as we watched and really get into the film and each other. I was way ahead of her and had her blouse off before she finished her sentence. I removed her skirt and spread her legs giving her pussy a quick lick and a kiss to show Lisa how turned on I was. Lisa stripped me as I watched the unfolding story on the screen. By now the Guy was naked and lying down with Lisa continuing to deep throat his massive cock as she finger fucked his asshole with hard pounding strokes. The other woman had put on what I recognized as Lisa's strap on dildo and was licking Lisa's cunt and fingering her asshole in preparation to mounting her and fucking her with the plastic cock. Suddenly the Guy pulled his cock out of Lisa's mouth and the other woman layed down on her back with that plastic shaft standing in the air. The guy moved Lisa over the other woman and helped Lisa mount the plastic shaft forcing it deep into Lisa's cunt while licking her asshole and finger fucking the other woman. Lisa began to pound her pussy up and down on that fat plastic shaft as she kissed and licked the other woman's heaving tits. The guy spread Lisa's ass cheeks exposing her pink rimmed anus to the camera then move in and rubbed his cock into the crack of her ass and pressed it into her puckered anus. Slowly he forced his massive penis up Lisa's asshole until all that was left outside was about a inch. Lisa in the meantime had continued pumping her pussy with the artificial cock as the other woman licked and sucked Lisa's tits and nipples. I watched transfixed as the guy began to stroke his big pecker in and out of Lisa's stretched anus with long hard strokes making her ass cheeks jump with each impact and shaking her full hanging breasts wildly. This scene continued until the guy climaxed in Lisa's asshole and Lisa climaxed on the fake cock. As the camera panned back I could see naked men an women all around the room fucking and sucking in ever imaginable way. Lisa was sitting behind me now stroking and fondling my cunt and tits as the short film ended.
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