“You ready for tomorrow night?” I asked via text. Cindy was quick to respond: “Yes. Nervous but excited. I’ve been wet non-stop all week thinking about it.” My response: “Don’t forget, be at my apartment at 5:30. That should give shit for brains enough time to get home. Park in the garage, 2nd floor. That way, no one will pay attention to your car. We need to be at the hotel before 7 so we can prepare” texting her again with the details to be sure. “Ok, Jake, how many guys?” “Let me worry about that. You worry about being a good little slut. Trust me, you will be used and worn out by the end of the night. If you are good, I might let you shower before sending your pathetic ass home.”
“Fuck you, Jake.”
The next night, I answered the knock, stepped back, and had to admit Cindy looked stunning: She was wearing a knee length black dress, tight against her curves, and looked amazing. Granted, only I would see her with clothes on, but I was impressed that she put on a show, likely missed, for dickhead. I invited her in, suggesting she leave the bag at the door. I told her to follow me to the bedroom, which she did with little hesitation. “Bend over and let me see how fucking wet you are, you whore.” Her face instantly flushed as she complied, leaning over the bed, hands out, legs spread. I gently pushed the dress up over her tanned ass, letting it bunch at her waist. As instructed, she was not wearing panties.
I reached out, sliding my hand against her bare, shaved pussy, commenting “you do not disappoint. You are dripping like a faucet.” As I slid a finger inside her overly tight pussy, I continued “this slutty little pussy is going to be stretched and filled by a bunch of strange cocks tonight.” She moaned and pushed back against my finger before I stopped teasing. Telling her not to move, I went to the nightstand, opened the drawer, and grabbed a toy and lube. After coating my fingers, I worked two into her tight, waiting ass. I liked that there was no resistance or hesitation to me playing with her anally. To think only a few weeks ago, I was her anal first. Now, as I slowly worked the medium sized njoy plug inside, she just groaned and relaxed until it was inside. “Oh fuck Jake, that’s fucking cold and big” she remarked.
“Based on how hot your asshole is, I wouldn’t worry about it being cold. As for size, yes, it is bigger than the other one. I want your ass to be ready tonight. I’m sure it will be pounded!” That done, I gave her ass a good whack on each cheek, told her to stand, and then got ready to head out. I grabbed my bag, which contained some robe, a blindfold, and a change of clothes. One last look around the room and we headed out, both wondering how the night would turn out. On the ride into the city, I had Cindy give me a show, making use of her still sopping wet pussy. I must say the sounds of skin against wet skin is rather intoxicating and makes the drive go much more quickly.
I told Cindy to wait nearby when I went to check in. In case Jim and Lucy had yet to arrive, I wanted to make sure Cindy did not know I had two rooms. Check in went smoothly with the receptionist confirming my cousin was already registered and in his room. As we found the elevator, my phone vibrated with a text from Mike, confirming he would be here around eight. I replied with the room number. I could tell Cindy was nervous with anticipation as we walked closer to the room. Once I opened the suite, Cindy looked around, dropping her bag in the far corner of the room. She stood next to the bed as I joined her, playfully slapping her ass for attention. “You ready?” I asked, surveying the room for how I was going to tie her to the bed.
It took me a few seconds to realize there was under the head of the bed, so I would be able to get a rope under and behind. I was glad to know this would work. Turning to Cindy, I let her know she had the next fifteen minutes to get ready, then I would be prepping her. She started pacing, asking “should I really be doing this? Oh god, why am I doing this?” Two quick strides and I was across the room, grabbing her shoulders and stopping her: “You are doing this because I told you you’re doing this, you stupid fucking slut. Do you understand?” Her eyes teared up slightly, but she nodded and seemed to calm down. For effect, I roughly grabbed between her legs, bunching her dress into the folds of her pussy, and rubbed her. “My dress, asshole” she cried out. As a response, I grabbed at the neckline and ripped down, hearing the fabric tear as her tits pulled free from the dress.
“The only asshole you need to be concerned with, you ungrateful bitch, is yours. It will be leaking cum by the end of the night for sure. Now shut the fuck up, get undressed, use the bathroom, and get your ass back out here” I commanded, voice elevated just below a yell. Cindy turned bright red, looked at me with fury, and stormed to the bathroom, trying to pull her ruined dress back up. She finally emerged, naked as asked, looking much more subdued. “Ok fuck toy, go lie on the bed, arms out straight.”
The next ten minutes were spent knotting her arms and looping the rope under the bed. Once finished, I stepped back and admired the view. Her arms were pulled taught against the sheets, slightly above her shoulders. Her tanned body contrasted well against the bright pink rope, bought for this occasion. Realizing it was close to the time Lucy and Jim would show up, I knelt on the bed and covered Cindy with a black cloth, tightly tying it around her head, blinding her for the next several hours.
“Jake” she asked, hesitantly: “What if I have to pee in the middle of this?” she asked. I laughed and replied: “Pee on the fucking bed and maybe, if you’re lucky, I’ll tape it and send it to Paul.” “You’re suck a fucking dick” she responded, regretting it the second she felt me pinch and twist her right nipple. “Ow, please stop!” As much as I relished having more fun, I heard a knock on the main door.
I greeted Jim with a fist bump before Lucy practically jumped me, kissing me hard. Jim laughed, closing the door behind them. I half walked, half carried Lucy into the main room, quietly explaining to them Cindy was waiting. Jim peeked his head in before returning and giving me two thumbs up. Lucy and I watched as Jim undressed, the three of us already having decided he would have first dibs. Loudly, I said “Okay, it is all there, you can have at her. She is on the bed. Only rules: No cumming in her pussy, nothing that will cause lasting damage, and no removing her blindfold. Otherwise, she is a wet and willing fuck doll. Get your money’s worth.”
Lucy and I watched from the doorway as Jim moved to the bed, roughly pulling Cindy’s legs apart so he could kneel and get into position. We could see Cindy’s breathing quicken in anticipation. I noticed Jim’s hair and stubble were turning grayer as the month’s I knew them went on. It helped give him the distinguished look I would expect for someone in their early fifties. Some would say he looked like George Clooney, although other than the hair and the nose, I did not really see it. Cindy’s moan as Jim pushed her legs back before pushing his hard cock inside her waiting pussy brought me out of my musing.
We continued to watch while Jim reached out, pinching Cindy’s nipples while he slowly fucked her tight, wet, adulteress pussy. “Cindy, you are suck a pathetic, cock starved little whore” I remarked, “letting your brother-in-law sell you to strangers for sex while your stupid husband is at home babysitting the kids.” Her head moved towards the sound of my voice as she moaned loudly, her body conveying how much she was enjoying this. The show continued, Jim pinching her nipples while continuing to slowly enjoy her wet and wanting pussy. After roughly fifteen minutes, I whispered quietly to Lucy that it was time for her to get ready.
We moved back into the living room, and I watched as Lucy stripped, making a show of it, ensuring my cock strained against my shorts. She looked and me and smiled as she pulled her strap on out of the backpack, she had with her. With a sparkle in her eye, she brought it to her lips and flicked her tongue over the tip of the rubber dick, winking at me as she slowly worked the tip in her mouth. Just to frustrate her, I turned and walked back to the bedroom door, looking over my shoulder to see her jokingly pout.
As Lucy walked by, she playfully slapped the side of my leg with the dildo and leaned in, whispering “why don’t you just get on the couch, and we can have fun instead?” I kissed her before pushing her towards the bed. Jim had moved back a bit and was holding Cindy’s legs back with one hand. With the other, he was playfully spanking Cindy’s tight ass. Seeing Lucy, he stopped, looking at us with a big grin. The room was eerily silent as Lucy took his place. Jim moved to the head of the bed and straddled one of Cindy’s tied arms before letting his wet cock slap against her lips, signaling for her to suck him. She opened and eagerly began sucking his cock. He reached out and grabbed her head, urging her to suck harder. Lucy positioned Cindy’s legs so they were resting on her shoulders, her calves solidly against Lucy’s erect nipples. I watched as Cindy, likely realizing something felt off, tried to move. Blindfolded and held by Jim, she could not move much and quickly gave back in, concentrating on Jim’s cock.
Lucy set a pace of long, forceful strokes, hungrily slamming her fake cock deep in Lucy’s well used hole. For my part, I continued to lean in the door, watching my sister-in-law being spit roasted, wondering what my brother would do if he knew just how much of a slut his wife was. Me, I’d be overjoyed, but that tightwad would likely jump out a window. A while into the show, my phone pinged with a text from Mike. He was outside the door, waiting for his turn. I went and greeted him. He stopped mid room as he caught sight of the show through the doorway. “Holy fuck, he whispered” while absently grabbing his own crotch. I laughed and slapped him on the back.
“You’re next man. Thanks for the cash. Here are the rules” and I explained the same rules I gave Jim and Lucy. For a second, I wondered how Mike would react given we had never been in a situation like this. The two facts that drove me to inviting him were that a) he had met Cindy and thought she was a hot mom and b) he always talked about how much he would love to be involved in a gang bang. That said, you never knew how someone would react when faced with a situation like this. I need not worry as Mike eagerly tossed his clothes off, discarding them on the couch.
He stood before me, short jet-black hair, waiting for me to tell him what to do. Mike was shorter, I would say about five six or seven, and had the usual darker Italian skin, making him look almost permanently tanned. He worked out, but still had a small gut, but was comfortable with his body. He had muscular legs and was packing a rather nice, thick cock. Never one to be great at sizing up cocks, I can only say he was about the same length as me, meaning average, but thicker. He was slightly thicker than the rubber dildo Lucy was now trying to slowly work into Cindy’s ass, having pulled the plug while I was busy talking with Mike.
Mike moved into the room, standing awkwardly, watching the show. Jim pulled his cock from Cindy’s mouth, stroking himself over her for a few seconds while we watched, finishing in several spurts across Cindy’s mouth, chin, and chest. After pumping himself empty, he moved off the bed, motioning for Mike to have a turn. Mike practically jumped on the bed, rushing to put himself in position before pulling Cindy’s head to his dick, pushing in until he was choking her with his girth. By this point, Lucy had the dildo almost completely in Cindy’s ass and was beginning to ass fuck her with the same strong strokes she had previously used on Cindy’s now well used pussy.
Jim, while recovering, looked on and decided to move closer. He reached out and began roughly massaging Cindy’s breast, pinching his nipple as he did. She was moaning against Mike’s cock, causing him to quicken his pace as he fucked her mouth. For me, it was the perfect time to have a little fun. Grabbing my phone, after answering a few snaps which distracted me, I called my brother “Hey bro, what’s up?” I asked. I listened as he droned on about how Cindy was out and stuck him with the girls. I put the phone on speaker, watching as Cindy heard the voice and tensed with fear.
The conversation went on for a minute before Paul stopped and asked “Um, Jake, are you fucking watching porn?” I laughed and responded: “No shithead, I’m watching your wife get railed by multiple dicks, covered in cum, being a good little slut!” The entire scene was priceless: Mike snorted, Jim and Lucy stopped mid pinch and mid stroke, and Cindy pulled against the restraints, smart enough to stay quiet, although she may have bit down on Mike. “You know Jake, you can be a fucking dick sometimes” Paul responded, before hanging up.
I laughed, knowing he would not for a second believe what I just said, but everyone else was still in a bit of shock. Mike released his hold on Cindy’s hair, so Cindy immediately cried out “Jake, oh my god, what the fuck?” “Cin, chill and suck a dick you dumb cow. You know that shithead is too stupid to ever believe what I said was true. Be a good little slut and carry on!” I nodded to Mike, who was still rock hard, and he snapped out of it, soon after sliding his cock back in her wet mouth. Lucy smirked, but rather than continue, left her strap on half buried in Cindy’s ass. She reached down and started playing with Cindy’s wet pussy, expertly brining her closer and closer to a climax. Jim was still shaking his head, laughing at my brazenness in calling Paul. I am sure we would joke about it later.
Lucy, sensing Cindy was building to orgasm, went back to slowly fucking her ass. Cindy sucked at Mike’s cock like the cock starved slut she was. I could tell she was cumming, watching her body tense and shudder as she continued to be flooded with all the combined sensations. Mike pulled back, not even needing to stroke as he shot his load over Cindy’s tits and nipples, covering her already sticky chest with more cum. Lucy pulled back, suddenly leaving Cindy’s holes completely open for the first time an over an hour. Thankfully, Jim looked ready for round two, so I commented “All empty. Can’t have that. Who’s going to fuck that hot, tight MILF ass?”
Jim took the hint and quickly placed himself in position to drive his cock deep into Cindy’s waiting ass. Lucy had warmed her up plenty, so Jim was able to slide in with ease. Lucy walked over, standing next to me as she removed the harness and the strap on before handing it to me. It was slick with juices and lube. The entire room smelled heavily of sweat, pussy, and cum. Lucy slid onto the bed, lowering herself onto Cindy’s face: “That’s right, Cindy. You better lick and suck that wet fucking pussy until she creams your face. She paid more than the rest of them combined to use your tongue as her fuck toy.” I remarked, watching is Cindy’s face is smothered by Lucy.
While Lucy grinded against Cindy’s mouth, Jim continued to fuck Cindy’s ass. Before long, he grunted and buried himself balls deep, flooding her with his cum. Sweating and thoroughly satisfied, he climbed off the bed, giving me a fist bump as he turned to watch Lucy. Mike, ready to join back in, replaced Jim between Cindy’s legs. “No need to be gentle. Her ass is well used by now. Stick that thick cock in and have at her buddy” I called out. Lucy grabbed Cindy’s legs from Mike, pulling them towards her, so Mike could concentrate on the task at hand. After lining up and applying a little lube, he thrust with a quick grunt, burying his thick cock to the balls, deep inside Cindy’s ass. She gasped into Lucy’s wet crotch as her ass was stretched more than ever before.
Mike roughly pounded her, his slick cock continuing to stretch her. “Wow Cindy, you’re like a bitch in heat. How many orgasms have you had, or have you lost count?” I asked knowing she could not answer. “Such a dirty whore having multiple cocks in your PTO mom ass. I’d ask what everyone would think if this became public, but I know the answer: all those perverted dads would line up with cash to be next on the list to fuck the stuck up bitch.”
Lucy came next, riding Cindy’s face and tongue until she came down from her orgasm. When she finally got up, Cindy’s face was a slick sheen of cum and pussy juices. Lucy came up to me, whispered in my ear “Now I get what you see in her” before giving me a nice, long kiss. Cindy, mouth finally free, was openly moaning and chanting softly “oh fuck, oh fuck, oh fuck” as Mike continued to fuck her loose ass. Jim, Lucy, and I watched as Mike continued until he too, buried to the hilt, let go deep inside Cindy. Fully spent, he pulled out as we all watched Cindy’s gaping ass slowly close, leaking cum as it did.
“Good little slut” I remarked. “Stay put while I let our guests out. I’ll be back for you sooner or later.” Cindy, lost in her own bliss, stayed quiet. The rest of us left the room as I closed the bedroom door behind me. Speaking quietly, we all agreed fun was had by all. Mike cleaned up and got dressed, telling me: “this was fucking great. I’d fuck her any day man” before saying by and heading out. Jim and Lucy, both having quickly toweled off, got dressed as well. We made plans for a late dinner the next morning, hugged, and they left as well.
I returned to the bedroom and the quiet, realizing a very spent Cindy was asleep. Her legs were still spread, ass covered in cum, sheets soaked beneath her. Her face, hair, and chest were a mess of juices and cum: Gently, I removed the ropes from both hands and untied the blindfold. As I removed it, Cindy opened her eyes, looked at me, and sleepily said “Thanks Jake. I’ll never forget this night.” I helped her get up from the bed and watched her walk to the shower. Looking back, I could see the bed covered in sweat and body fluids, evidence of a night of fun. I thought about snapping a picture and sending it to my brother, but I also knew I came close to crossing a line tonight by calling him. I was in no way done with Cindy, so this would stay our little secret.
While she was in the shower, I caught up with a few people on various messaging apps, with one particular picture received causing my cock to harden.
Once Cindy was showered, I told her to get dressed, having decided we’d head home and sleep at my house. We left the keys to the room on the desk so I could do remote check out in the morning. Cindy, sleepy and admittedly a little sore, clung to my arm as we made it to the car. She was quiet on the ride to my place, talking only to tell me she was grateful I helped her fulfill a major fantasy.
It was before ten when we got back to my place, but Cindy was spent and needed a little after care, so I stripped to my boxers and slid into bed with her. Holding her against me, feeling her warmth, we settled in for the night. As I held her, I reminded her “you staying changes nothing. You’re still a stuck-up twat that I will continue to use and abuse as I see fit, understand?”
“Yes Jake. And Jake, fuck you” she said, before snuggling her head into the pillow, soon to be asleep.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/nnz44l/my_little_fucktoy_sharing_is_caring_mmff/
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