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The Babysitter Returns

Category: Group Sex
08.04.2020
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It had been awhile since our sex life had any adventure in it and Jackie and I thought maybe turning 40 had something to do with it but just when you start to have doubts, something can always happen.

Jackie got a call from Jill, a young girl who had babysat for us during high school, and she had asked if she and her husband Don could stay with us for the weekend. Jackie immediately said yes, as Jill and her were quite close. As for myself, thinking about Jill gave me an instant hard-on.

Back in her babysitting days, I always made sure my wife took her home, not trusting myself with her. She was a petite little thing, probably not weighing a 100 lbs., but had the perfect little bouncy tits and a so very nice tight ass. With beautiful green eyes and a pouty little mouth, she knew how to turn heads.

Friday came around and Jackie was so excited as they pulled up in the front yard. Just coming from the wedding they were in town for, Jill got out and looked amazing, married life had not hurt her any. Coming up and giving me a hug, I did my best to control myself as I felt the tight body of a 22-yr. old press up against me and hug me tight. Don gave Jackie a big hug and we all went in the house. As the girls chatted away, Don and I had a beer and sat down. As he rattled on about his job, I wondered why Jill had married him. Lots of their friends and other people wondered the same thing; little did I know that we were going to find out this weekend. Watching Jill talking to my wife, she looked so hot and sexy, I was envious of Don as he talked on and on, unaware I was undressing his wife in my mind.

Deciding to call it a night, Jackie showed them the guestroom and made sure they were comfortable and then came to bed. As we lay in bed, Jackie went on and on about how glad she was they were staying with us and then rolled over next to me with a wicked look on her face. I asked her what she had on her mind. She said “you may not believe this, but when Don gave me a hug when they got out of the car, he gave my ass a big squeeze.” What do you think about that? “Looks like he knows a good piece of ass when he sees one” I said as Jackie just laughed. The next morning I had to go into work for a few hours to catch up on a few things. As I left, Jackie gave me a kiss and said her and Jill had decided last night that they just wanted to get a little sun out by the pool and relax. Picturing those two in bikinis, I knew I would hurry home.

Work didn’t take as long as I expected, so on the way home my mind started thinking about two sexy women laying by the pool. My foot got heavy as I couldn’t get home fast enough. As I got home, I went through the kitchen and grabbed a beer and went out into the closed in patio. As I was about to go out on the pool deck, I looked out and saw a great sight. Both Jackie and Jill had bikinis on that didn’t cover much and were laying face down with Don kneeling between them. He was rubbing suntan oil on both of them with each hand. Both of their tops were undone as he worked the oil all over their backs. He started massaging Jill’s ass, pulling her bottoms up into her crack, exposing both cheeks of her tight, young ass.

Stepping outside quietly and staying hidden behind the pool, I could start to hear Jill moan as he massaged each cheek, working the oil all over her. I wondered how far this would go. I soon got my answer. Jackie`s head was turned away from Jill as Don’s hand slowly worked its way down her back and over her gorgeous ass, slowly working her bottoms up higher and higher as I heard Jackie start to breathe heavy as he now turned his full attention to her, massaging her ass with both hands. As Jackie started to squirm with passion, Don reached up and started to pull her bottoms down. At the moment of no return, Jackie turned her head, looking at both of them. Praying that she would go on, my prayers were answered when she raised her butt and let Don pull her bottoms down.

Taking my rock hard cock out of my pants, I watched as Don worked the hot oil up and down the crack of my wife’s ass, slipping his fingers into her by now dripping pussy. Jill decided to get up and I saw those perky little tits for the first time as her nipples stuck out a good inch as she kneeled on the other side of my wife. Now with two sets of hands on her naked backside, I knew Jackie would not be far from orgasm.

As they both rolled her over, I wondered what would happen next. Jackie had never liked the ides of being with another woman so I didn’t know how she would react as Jill started to massage her breast as her husband worked his way down to my wife’s perfectly shaven pussy. Spreading her legs as wide as they would go, Don pulled her pussy lips apart as her juices dripped down her ass. As his tongue made contact with her clit, Jackie nearly jumped a foot as he worked his tongue back and forth over her engorged lips. Hearing Jackie moan, I looked up and saw Jill take my wife’s nipple into her mouth and start to suck on it, pulling on it and stretching it until it popped out of her mouth, then attacking it again as Jackie exploded into her first orgasm. Don held on tight as she bucked her pussy into his mouth, cumming loudly as always.

As she laid there calming down, I could see that my wife was wondering what in the world had she just done, wondering whether to let this go on as Jill got up and slowly peeled her bottoms off, revealing her young pussy that had just a small triangle of hair on top. As my wife sat up on the pool chair, Jill kneeled in front of her husband and pulled down his swimtrunks. I saw my wife’s mouth drop as she saw his large, uncircumcised cock. Now maybe we knew why Jill had married him! My cock is 8 inches long and very thick but Don’s cock was just as thick and at least 2 inches longer as his wife took into her mouth. Licking the head, it didn’t look like she could even get it in her mouth but she did as she got just the head in, swirling her tongue around it as she pumped the huge shaft with her hand.

Getting up, Jackie kneeled beside Jill and started running her tongue up and down the shaft. Jill then started on the other side of his cock, both women on his cock, face to face as they ran their tongues around his thick shaft, attacking it like it was their last meal.

Pushing him down on reclining pool chair, that huge cock stood straight in the air as my wife attacked it. Knowing that she can deepthroat my cock, I knew what Don was in for. Getting on her hands and knees, Jackie slowly started working his huge cock a little deeper each time as she worked it in and out of her mouth. Jill was kneeling beside; watching as that horse cock went further and further until it had started going down my lovely wife’s throat. As each stroke went deeper and deeper, both of their eyes got bigger and bigger as that cock disappeared further down Jackie`s throat until finally she had it all except for the last inch. Try as she may, she just couldn’t get that last inch! Going up and down on it, all the way out, then all the way back down again, I knew Don couldn’t last long as he grabbed my wife’s head and started fucking her mouth and throat insanely as he started shooting his load down her throat. Milking the last bit of cum out of his now softening cock, his cock came out of her mouth, the head dark purple from the explosion. Fascinated with his uncut cock, she worked the skin up and down over the head, licking the last drop of cum from it.

Getting up, Don jumped in the pool to cool off and Jill laid back down with my wife kneeling beside her. They looked at each other and Jill took Jackie`s hand and put it on her breast, rubbing her own breast with Jackie`s hands. Looking into Jill’s eyes, you could tell she was asking my wife to take care of her. With shaking hands, she started to massage those small, perky tits and worked those erect nipples between her fingers. My wife may have been new to this, but it didn’t take long for her to have Jill moaning as she dropped her mouth to her nipples and started sucking. I nearly came right there; never did I ever believe what I was seeing would happen. Sucking on her nipples, my wife’s hand slowly worked its way down to Jill’s, until now, neglected pussy, opening those swollen lips and exposing a clit that stuck out as far as her nipples. Rolling her nipples in her mouth and her clit with her fingers, Jill came to her first orgasm as her husband walked up, still dripping from the pool.

Thinking Jackie would go after him again, I was surprised as she slid down between Jill’s legs and started exploring a woman for the first time. I could see her tongue running up and down her pussy lips, occasionally going further down to swirl around her tiny, pink asshole and back up to her clit, bringing Jill closer to another orgasm.

Don had dried off and put some suntan oil on his cock and was stroking it back to its hard 10 inches. Standing over these two hot women, he poured some oil on Jackie`s ass and rubbed it in as he knelt behind her. Bringing his cock up to her puffed out pussy lips, he shoved all ten inches into her with one stroke, making her scream with surprise and desire. As Don pounded her like there was no tomorrow, Jackie lost interest in the pussy in front of her as her mind was in only one place.

Looking like she was left out, I decided I had watched long enough and walked out to see what would happen. Don and Jackie were fucking so hard, I don’t know if they even heard me as I walked up. Jill’s eyes got big as she looked from me to her husband. Don just turned to me and smiled as he jackhammered my wife doggie-style. Walking up to Jill, she was on her knees as I offered her my cock. Struggling to get the head in her mouth, I could tell someday Jackie would have to give her cocksucking lessons, but not today as I watched our babysitter work on my cock, looking up at me with those beautiful eyes.

Laying her down on the chair, I lifted her legs over my shoulders and started to lick on the same pussy lips that my wife had just done, tasting her sweetness. Running my tongue up and down her slit and then thrusting it in as far as possible, I ran my fingers along the crack of her ass, gently caressing the area between her pussy and asshole, working my finger closer and closer to her tight hole. Making contact with my finger, Jill let out a loud moan and jumped as I penetrated her tight hole with a finger as I worked on her clit with my tongue, making her cum loudly as she screamed for me to fuck her.

Bringing my cock up to her pussy, I looked over to see Jackie was now on top of Don and was bouncing up and down on her young studs cock, her tits in her hands with a look of pure lust in her face. As Jill guided my cock into her pussy, I had almost forgotten how tight a pussy a woman of her age has as I drove my cock all the way in. Looking down as I started to slowly fuck this young vixen, it was a heavenly sight as my shaft went in and out, looking as if it would rip her apart each time. Pounding harder and harder, Jill came with such force that I could barely control myself. Hearing my wife scream, I looked over to see that Don had cum deep inside her pussy and Jackie was still sitting on top of him with her tits in his face. Pounding away at Jill, I watched as Don’s cock popped out of my wife’s pussy, cum running down it.

Turning my attention back to Jill, I rolled her over on her hands and knees, doggie style, my favorite position. Slowly running my cock in and out, I poured suntan oil on her ass, making it shine as I rubbed it in.

As Don tried to recover, Jackie came over and smiled at me as she watched my cock fucking another pussy. Sitting down beside Jill as we fucked, Jill pushed her down and spread my wife’s legs, looking at the pussy her husband had just ravaged. It looked red and puffy from the pounding it had just got and there was still cum oozing out of its violated lips. With both of them making eye contact with each other, Jill lowered her head and started to lick the cum out of my wife’s pussy. Jackie`s eyes got big as silver dollars as she watched this young girl eat her husbands cum from her pussy. Watching this and looking at Jill’s tight little asshole winking at me as I fucked her pussy, I knew I wouldn’t last much longer. Working my finger down to her asshole, I eased a finger in to the knuckle and this shot Jill off to another orgasm as I shot my load deep in her tight pussy.

Lying there, everyone catching their breath, no one knew what to say except wow! Don came over and sat by his wife, asking if she wanted to fuck him now, but she said she couldn’t take anymore but she would give him a blowjob. With that said, Jackie smiled at me and gave me a wink. As Jill started working on her husbands spent cock, she could take half of it in her mouth. What a sight as she slobbered on it, trying to get it hard again. It was obvious it was going to take some time.

Feeling Jackie pull on my cock, we stood up and she led me over next to Don and Jill and got down on her hands and knees and started to put on a show. Picking up the suntan oil, she covered her ass with oil and put her tits and face down on a towel, sticking her ass up for everyone to see. Reaching back with her hand, she started rubbing the oil on her ass, then into her pussy, and finally up around to her less than virgin asshole, starting slowly with one finger working it in to the knuckle, watching the tiny ring grip her finger. For someone who only a few years ago didn’t like anal sex, when she was in the mood now, no one could be any hotter and willing.

I realized what Jackie was really doing now, wanting to show these two young sexpots that the older crowd could still teach them something. I picked up the oil and put more on her ass, letting it run down to her asshole, as she worked two fingers in past her tight ring, moaning and wiggling that ass in our face. By this time Don’s cock had made a miraculous recovery and he was watching the show intently as Jill stroked his cock with her hand as her eyes were glued to my wife’s ass.

With my 8-inch cock rock hard again, it twitched in anticipation as Jackie pulled her fingers out and spread her asscheeks with both hands. Pouring oil on my cock, I laid it against the tight anal ring of my wife’s asshole. Pushing just the head in, I thought Don was going to faint as my whole 8 inches disappeared in a matter of seconds. With my wife still holding her asscheeks wide open, I pulled all of the way out, leaving her hot asshole wide open. What a sight! With an audience watching, I could hardly control myself. Shoving my cock all the way back in, Jackie moaned with pure lust, knowing she was the center of attention. “Fuck my ass, fuck my ass with your hard cock” was all she could say as I pummeled her tight ass, over and over again, having no mercy. Looking over at Don, I knew what he wanted. “Are you going to let Don fuck your asshole with his big hard cock after I cum in it ” I asked her as I stayed still and let her slam her ass back and forth onto my cock. Slowing down, I knew she was giving it a little thought as she looked back at us. At that moment Don would have done anything to have my wife’s ass. “God yes, Please let me have your ass, oh God yes” was all he could say. Looking him in the eye, she said “after my husband cums in my ass, I want you to stick that huge cock in my asshole and flood it with your cum.”

Looking into my wife’s eyes, I knew she was turned on by the thought of two cock’s cumming in her ass. That thought shot me to the edge as I pounded my cock deep into her asshole and filled her ass with my cum. Looking at Don, he knew what he was fixing to do and was so excited I was afraid he was going to cum before he got to. As I pulled out of my wife’s asshole, my cock was still semi-hard from the thought of another mans cock in my wife’s ass. Cum was dripping out of her ravaged asshole as she reached behind her and rubbed oil over his big cock. Opening her asscheeks for him, her asshole still halfway open from my cock, Jackie turned and said, “come on big boy, fuck my ass. ”

Jill held her husbands cock against my wife’s asshole and guided her husband in as the head of his horse cock popped in, twitching with excitement as he entered her tight hole for the first time. Sliding in slowly, Jackie grunted as she felt this huge horse cock stretch her asshole to the limit, clenching her fist as Don gave her 2 inches more than she had ever had before. Looking back at us with her eyes rolled up in the back of her head, Jackie seemed to have lost her breath with the fullness within her.

As Don started to slowly pull his cock out and then back in, quickening his pace, Jackie moaned with both pain and pleasure. Watching that big cock stretch my wife’s ass, Jill bent over in front of me, pulling her asscheeks apart. Looking back at me with those big eyes, she said “be gentle, it’s my first time, please J.D.,fuck my ass.” Looking at that virgin little rosebud, my cock recovered instantly as I massaged oil all over her ass and into that tight little hole. Flinching as my finger worked it’s way past her anal ring, Jill moaned as it slid in past the knuckle, slowly stretching it as I worked my finger in and out, slowly, as she became use to the intruder. “Oh please fuck my ass, please” Jill said as I laid my cock up against her virgin asshole.

Covering it with oil, I held it forcefully against her tight ring until the head finally popped in, causing Jill to wince with pain. Letting her become accustomed to the feel of my cock in her ass, I looked over as Don was in heaven, working his big cock in and out of my wife’s well-fucked ass. Pulling his cock all of the way out with a pop, Don would then shove it all the way back in as Jackie began to scream for him to keep fucking her ass.

Turning my attention back to Jill, I told her to start pushing back on my cock when she was ready. Looking back at me with a look of uncertainty on her face, she started to slowly work her ass back further onto my cock. “I don’t know if I can take it” she said as the first 4-inches were in. Gripping her hips, I slowly pushed until all 8-inches were in, making Jill nearly collapse. “That whole fucking cock is in my ass, oh fuck” was all she could say as I held myself still, savoring the tightness of her virgin ass. Slowly pulling out, an inch at a time, and then back in, Jill began to enjoy it as she began to move her ass back and forth on my cock.

Hearing Jackie scream, I looked to see that Don had her by the hair, pulling her head back as he pummeled my wife’s ass. Losing control, Don screamed as he shot his huge load deep into her ass, making Jackie cum with wild abandon as she felt his hot cum deep inside of her. Kneeling there, that huge cock began to shrink and plopped out of my wife’s plundered ass, making her moan with the feel of emptyness. As cum leaked out of her ass, dripping down to her pussy, I thought he must have pumped a gallon of sperm into her!

Feeling Jill start to work her ass back and forth on my cock, I looked down to see that tiny rosebud stretched wide by my cock as it went in and out. My wife then moved over beside me and smiled, pouring oil on my cock and Jill’s ass, massaging her asscheeks as I picked up the pace, driving my cock harder and harder into her asshole. As Jill began to scream she couldn’t take anymore, I drove my cock all the way in as Jackie screamed for me to cum in her ass. Losing complete control, I came, pumping her full of hot cum.

As my cock came out of Jill’s now violated ass with a pop, she collapsed moaning she couldn’t believe what had just happened. Looking over at Don, he was laying on a towel all wore out next to his wife. Who would have ever believed!

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Roger Dousay wrote

Loved this story. My wife and I never had sex with any of our baby sitters. However, on quite a few occasions, we enjoyed sex with couples half our age and younger….My wife loved 18 to 20 year old young men’s hard cock. She has had sex with these young men many times. She is 67 now. The last time with an 18 year old, she was 64.