[M]y [F]ucktoy – Opportunity Hits

As you’ll read, an opportunity too good to pass up came about with Cindy. Unfortunately for all of us, they’re away most of the weekend and next week, so no family dinner and no adventures for a while. I’ll keep writing and focus on some of the other sharing I’ve been doing.

Cindy was starting to text more. We had awakened a monster, and not that I am complaining, but I thought this would be a good time to focus on work and remind her I decide when and where she gets off. The plan was to push her off until family dinner, tease her a bit, then wait until next week to be alone with her again. Of course, as all good plans go, this one blew up Wednesday around lunch.

“Jake, Paul’s heading to New York tonight for a meeting. He’ll be there overnight.” The text explained. I knew the underlining offer/begging of the text and as much as I should stick to the plan, I couldn’t pass up an opportunity to have a night of fun, degrading sex. “And?” I replied. “Please Jake. You know why. Come over? I can drop the kids at my mom’s house after school. You can do what you want to me all night long.”

“And what is it you think I want to do, Cindy?”

“You know Jake.”

“Say it.”

“Use me as your fuck toy. Let me suck you cock before you fuck me!”

“Fuck you where?”

“Fuck you Jake. Don’t play.”

“Where?”

“In my ass, Jake. I want you to come over and fuck my ass!”

I smirked and responded: “I think instead I’ll just screenshot this conversation and send it to my brother. What do you think Mr. Pathetic would do if he knew his wife was begging his brother like this?” “Asshole” was her response. “Fine, you needy bitch. I’ll come over. Ground rules:”

“1. After dropping off the kids, come straight home and facetime me.”

“2. Be naked and have the plug. You’re going to work it in your ass while I watch and leave it there until I come over, sometime after dinner.”

“Jake, what if I, um, well, have to go?”

“You take it out, go, and clean up. Eat healthier, you won’t need to go as much.”

“Asshole!”

“3. Work on those tan lines. It’s hot and sunny out. Your deck is private enough. I expect you to be out there naked when I get there.”

“What if Jayden is being creepy and trying to look through the trees?” Jayden was their high school neighbor. I think he was a sophomore or junior. They swear they saw him spying on her last summer. I’m sure he did. As much as she’s a bitch, she’s a looker.

“If you see him, let me know. I’ll see how much he’s willing to pay for an hour or two of sex with the neighborhood MILF!”

“You’re such a dick, Jake.”

That conversation over, I went back to work and lost track of time. My phone buzzing with an incoming facetime request startled me. Upon hitting accept, I was greeted with a nice view of Cindy’s face and naked chest. “Put the camera down and let me see you’re fully naked.” I commanded without saying hi. After admiring her toned body on the screen, I remarked “Good girl, you know what’s next.”

“Um, Jake” she hesitated: “Don’t be mad, but I don’t have lube. I can’t put the plug in without lube.”

“Ha, you pathetic slut! I know my brother’s dick doesn’t get you wet, so you must be lying.”

“You know we just don’t do it in that case.”

“Well, I’m sure you’re fucking wet now. Use that. Better yet, go to the kitchen and get coconut oil. I know you cook with it. You’ll be lubed up and taste good!” She questioned the use of coconut oil. I asked her if she lived under a rock. She complied and went to the kitchen. “Now that you’re in the kitchen, might as well just work the plug in there. Prop the phone on the hutch and sit on the table. I want to see you rub those ass cheeks all over where Paul usually eats. Prepare a meal for me that he’ll never get to enjoy.”

She got up and although the view wasn’t great, gave me a show good enough to make me hard. I was looking forward to tonight, thinking about all the ways I could degrade her and work insults about my brother in. The last being a request from a fellow redditor and one I would enjoy. Sadly, or not, I’m sure Cindy will enjoy as well. For a small plug, there was a lot of gasping and groaning while she worked it in. “About time slut. Get the phone and show me a close up.” She did and it was a sight to see: Her dark, wringled rosebud, slick with oil, was still clenching against the plug as she tried to get used to it. Her pussy lips were plastered together, her sticky wetness holding them like glue.

“See you tonight” I said before abruptly ending the call. I finished up work over the next thirty minutes and put my out of office on, deciding I needed to head a few towns over to the local sex and smoke shop. I wanted to see if there were any fun toys I could buy. And maybe some fun, flavored lube. My shopping trip was fruitful: A purple colored dildo that looked like a weird, overly veined dick, with a large set of balls; a black metal vibrator, medium and almost bead like, and some strawberry kiwi lube. My last stop was at Home Depot for some rope. I wonder how many people go to home depot for the same exact reason? I chose a multi-colored rope that was coated and seemed to have a small amount of give.

At this point, other than a hard dick and lots of porn guiding me, I had zero clue the proper and fun ways to restrain someone. I headed back home to grab a small dinner and shower, but made sure to check online for a couple different articles on basic knots, etc. I decided a shorter rope to help keep her legs harnessed back and a longer rope to tie each hand to the bed would be the best foray into restraining. I dressed in dark cargo shorts, sans underwear, and a light blue polo. Slipping into a pair of quiet, slip on sketchers, I headed out.

It was a little after six when I pulled up the driveway. I grabbed my backpack, filled with the purchased goodies, and headed quietly around back. Cindy stirred when he climbed the few steps to the back deck, but stayed where she was. She was on lying on her stomach on the lounge chair. I dropped the bag and admired her: Her blonde hair, starting to show her true brunette roots, was in the usual ponytail, snaking lazily between her shoulder blades. She usually let her hair run pretty long, so it normally reached halfway down her back. Her ass, small and tight from running, was starting to match her tanned body, although I could still see the tan lines where her bathing suit was while she sunned over the weekend. She was wearing those stupid big sunglasses that seemed all the rage. Her muscular, tanned legs stretched behind her.

The best part of the view was the slight silver handle, glistening in the sun, firmly between her butt cheeks. I smiled knowing she had been plugged for a while now. I resisted the urge to go over and touch her, instead sitting in a deck chair nearby. “My, we seem comfy!” I remarked. “I did as you asked Jake. I’m out here, naked and waiting.” I looked around and noticed all the play toys, zoning in on one in particular: a fake, but quite real looking, riding crop. My nieces were big into horse riding and my mother had gotten them both these stupid riding getups as costumes.

I got up and walked around, circling Cindy as I tried to nonchalantly grab the toy. It was about two feet long and flexible. I told her to close her eyes as I walked closer and traced the tip of the crop from shoulder blades down to the start of her ass crack. She shuddered and let out a sigh. With a quick snap, I brought it up and landed a quick blow to her left ass cheek. “Ow” she cried loud enough for anyone nearby to hear. “Fuck Jake. That hurt!” I snapped her right cheek for good measure and told her it was time to go inside.

Upon entering the house, I pulled off my clothes, smiling as Cindy stared longingly at my hard cock, standing at full attention. “Well, what are you waiting for slut? Get over here and suck it.” She was on her knees, my cock in her mouth, in seconds. She eagerly sucked and slurped my cock as I grabbed her head and forced myself deeper. She was choking and despite the sunglasses, still on, I could tell she was tearing up. For several minutes, I forcefully face fucked her, letting up only when I knew I was getting close. I was not ready to end the first round of fun so soon.

I pulled back and let her catch her breath, smiling more as tears streamed steadily down her flushed cheeks. I removed the glasses and tossed them on the table. With teary green eyes, she looked up and begged: “Let me taste your cum, Jake. Let me suck you off.” “Ha, you’d like that too much. No, I have other ideas in mind. Get up.”

She stood, and a look of hesitancy crossed her face: “Um, Jake, I have a confession to make.” “Oh really, this ought to be good. You sure you want to make a confession now?” “Yes Jake. I, um, I. Wow, this is embarrassing. You know… you know that crop you used outside? I kind of, well, found it when cleaning up today and put it there, hoping you’d find it. But I’m scared Jake. It hurt. Please, maybe we should put it back?”

“Ha, you are such a twisted bitch. No fucking way. Now I’m going to make sure we have fun with it. You’re such a slut, putting your daughter’s toy somewhere for me to find and use to punish and pleasure you. Maybe if you’re lucky, I’ll fuck you with the handle, so every time she goes to play with it, you’ll be reminded that it was in your dirty, little twat.” “Get upstairs, you pathetic excuse for a mother. Lie on the bed. I’ll be right there.”

When I entered the bedroom, she was already spread eagle on the bed, fingers buried in her vagina. I dropped the bag and admired the front view. Someone asked to describe who famous she most closely resembled: Looking down, I’d have to say she looks like a longer haired version of Gweneth Paltrow, with a similar jaw line and facial features. “Now it’s time to restrain you and use you like a good little fuck toy” I remarked as I reached down and grabbed the rope from my open bag before moving to the side of the bed. Cindy looked at e holding the rope and I saw a flash of fear and lust. I’d like to say the next part was sexy and all fifty shades like, but in reality, trying to tie someone’s arm with rope (easy), then throw the roped under the bed, only to grab it and tie the other arm is easy. It is not! But I managed and after a little here and there, I had Cindy’s arms both tied at the wrists. The rope went under the bed and was tightened so she could not move her arms at all. She looked at me expectantly as I moved and started tying a shorter strand of rope to her left leg, just above the knee. I looped the rope over her upper left arm and back under, pulling her leg so she bent in and her knee was inches from her breast. I continued the rope across her chest and did the opposite loop on her right side. The result was her legs both tightly pulled to her chest. The last small piece of rope I tied above both knees, pulling them tight together.

There may have been a better or easier way to this (open to suggestions) but it worked. This is one area where I wanted to make sure, regardless of everything else, that she was okay, so I asked: “You okay Cin? I’m going to make you think twice about being slutty like this, but only if you’re okay with being tied up like this?” She nodded and confirmed. I will spare the details, but we quickly discussed a safe word before continuing. Yes, in the future, we’ll make sure we do this ahead time, but new territory and all.

I grabbed the riding crop, which I was sure to bring up with me, and moved to the side of the bed. I held it up, making sure Cindy saw what was soon to come. She tried to squirm against the ropes and that tinge of fear was back in the twinkle of her eye. Not holding back, I landed a quick flick of the crop against her ass, being sure to let it land across both cheeks. “Oh shit that fucking stings!” she cried. I landed three more in quick succession. “Fuck, fuck, fuck. That fucking hurts.”

I moved up and she looked at me confused, eyes teary again. A quick snap and I landed the crop across her sensitive nipples. She jumped, pulling against the ropes, and cried out: “You motherfucker!” I laughed and remarked “Only if you behave.” I traced the end of the crop over her cheek before landing a few smacks across the globes of each breast. She was breathing heavy and tears streamed as I practiced the techniques I watched earlier on Red Tube. “Shall I continue? I asked. She nodded through clenched teeth.

Moving back down, I landed six snaps in rapid progression. Cindy swore loudly as each landed. I did not want to overdo it, so I decided she had enough. Her ass was fiery red and would surely bruise. Her chest would likely as well. As promised earlier, I grabbed the crop, flipped it, and slid the handle deep in her eager pussy. She strained against the ropes and moaned, letting out a “fuck yes” as her quivering pussy finally had something to clamp onto.

Her ass was on fire and I could feel the heat each time my hand got close. I knelt on the bed so I’d have better access and kept slowly fucking her with the crop handle while also flicking and pinching gently at her clit. She came hard crying out “god yes, fuuucccckkk” as she came. Her legs were shaking and after catching her breath, she asked me if I could untie her. I laughed, moving from the bed. “Not even close!” I replied.

I dropped the crop to the floor near my bag, letting the grool soaked handle drop to the floor. Ha, if it stained, maybe dickhead will see and wonder what it was. I grabbed the toys and sat on the bed, positioning myself so I had access to dripping box. I spent a few minutes sliding my hand over her smooth legs, being sure to be gentle against her quickly bruising backside. She sighed and relaxed against my touch. “I’m not letting you loose unless you say the agreed word, but before I start again, you okay?” “Yes” she replied in a sexy, wanting way.

I slowly pulled at the plug, watching as her tight anal ring expanded and grasped at the toy, almost as if to say, please let me keep it. My cock twitched watching her relaxed hole quickly tighten as I placed the plug beside me. I grabbed the purple dildo and applied a good amount of the flavored lube before placing it against her exposed asshole. Slowly, I pushed the cock, applying pressure as I watched it expand her ass. She exhaled loudly but stayed otherwise quiet. I could see her body heave slightly as her breathing intensified. Once her ass sucked the tip in, I paused so she could acclimate to the larger toy. The toy was girthier than my cock, so this would be the largest thing she’d taken: I knew to take it slow.

For five agonizingly slow minutes, I worked the toy into her expanding asshole. Finally, the balls touched against her ass cheeks. “Hey Cin, you should see the big purple dick in your ass. I can’t wait to fuck you like the whore you are.” For once, she had nothing to say. I started pulling the toy out before sliding it back in. I loved watching how her ass gripped at each of the veiny, ribbed lines. I started gently, only removing the toy halfway before pushing it back in. Before long, I increased the pace and the length until I was fucking her with the entire length of the dildo. She was panting and moaning while trying to meet the toy as I buried it in her ass. I grabbed the vibrator, switch it to highest speed, and planted it firmly against her clit. She cried out and came almost instantly. “Stop. I can’t take it. Too sensitive. Jake, please stop. Please, please.”

There were many highlights to this night, but this next part is one of the best. I pulled the vibrator away and turned it off, leaving it on the bed close by. The dildo was deep in her ass, so I let go and left it there. “Jake, I’m getting tired, can we take a break? I promise you can do what you want after. Please. I’ll blow you.” She asked. “You need to earn a break by being a good girl. So far, you’ve been a dirty slut” I replied as I watched around the bed, watching her. I was able to take her phone off the nightstand without her seeing and knelt on the bed. I knelt over her face, a little awkwardly, and told her “lick my asshole. I want to feel that tongue inside me.” She strained against her ropes before her tongue found the spot. I sat in as much as I could, letting her tongue flick over me.

I felt incredible and I wanted to continue until I came, but I pushed forward with my plan instead. I flicked her phone screen on (stupid her – no password) and hit the phone. I clicked on my brother’s entry in her favorites and hit connect. After putting the phone on speaker, I placed it on her chest. She paused her tongue as she heard the dialing. I moved, looking down at her with a smirk as my brother answered: “Hey babe, what’s up?”

Her look said it all. She was afraid of what I had planned. I put my finger to my lips, signaling I was going to be quiet. “Oh hey babe. How’s New York?” she tried to calmly ask. I re-positioned near her head while she adamantly shook her head no, pleading me to behave. As he droned on about how great he was and how great the deal was going, I started moving and twisting the dildo. She held on for a minute before finally letting an “oh god” slip. “Everything okay”, he asked. “As I slid the length of the toy inside her, she said, through clenched teeth, “sorry, forgot I had to tell my mom to get the girls to bed early.”

“Oh, they’re at your parents tonight?” he asked. “Yeah, they wanted to go and I needed the peace. It’s been a hard week.” She answered. I decided to up it a notch while they continued to talk about their Saturday plans. I pressed the on button on the vibrator and slid it against her sensitive clit. This time, instead of a moan or comment, she let out a noise that sounded like a half squeal and a half cry. “Babe, you’re acting real weird. You sure you’re, okay? What’s going on.”

She looked at me, pleading, and I smiled. I moved the vibrator away from her clit and slid it inside her exceptionally wet pussy. “Yeah babe, just heard a noise. You know how I get when I’m alone. You should go get ready for tomorrow. Love you babe!” she said, basically pleading for the call to end. “Ok babe, I’ll call you tomorrow. Bye” and with that, he disconnected. I moved the vibrator back to her clit, holding it there while I continued to fuck her ass.

“Good girl. When he comes home tomorrow, how are you going to look him in the face and have any respect for him, knowing he was clueless while I have you here, tied up, ass filled, using you as I please? He’s such a dickless fuck. The worst part: I know he got blessed with a bigger, thicker cock than me. And he’s too much of a loser to fucking use the gifts he has. “

Cindy was too busy shaking and breathing rapidly, surely in the middle of a long series of forced climaxes. My dick hurt it was so hard, so I finally moved and slid inside her hot, slick hole. My balls bounced against the rubbery toy balls each time I buried myself in her. I kept the vibrator against her clit, upping the intensity to high. Between the tightness of her pussy, pushed tight by the big toy in her ass, and the vibration of her and the vibrator against me, I wasn’t going to last. Before long, I buried my cock and remarked: “Maybe next time, I should let him watch. See what a real man does to his wife. Would you like that?” I asked as I lost control and shot load after load of cum deep inside her pussy.

After finishing, I slowly removed the dildo from her ass, marveling at the gape as her muscles slowly closed. She had the toy in for so long that she was going to be ready and loose for most of the night. I’d have to take advantage. I slowly removed the ropes, letting her free of her restraints. As I leaned over to remove the last knot, she surprised me by grabbing hold and pulling me to her. Before I knew what was happening, she had her lips locked to mine and her tongue probing mine. I let her have her small win before breaking loose and telling her it was time to clean up. She was spent and couldn’t move, so I grabbed the toys and cleaned them up.

Glancing at the clock, I was surprised to see it was approaching eight. Cindy had finally moved and was sitting on the edge of the bed, phone in hand. I quietly watched while she called, talked to, and said goodnight to her daughters. Her entire body was still flushed from earlier and I could see the rope outlines. “Let’s shower” I commented when she was finished with the call, offering her my hand. As with the last shower, we spent quite a bit of time under the steamy water. We touched and soaped each other long enough that I was ready for round two. This time, I took advantage of Cindy’s relaxed and ready asshole, slowly pumping her until I creamed her no longer innocent ass.

When toweling off, she asked: “Jake, were you serious about offering me to Jayden for money?” Wow, that was kind of out of the blue. Confused, I asked “Um, sure, but that’s not likely to happen.” “Oh, too bad. It kind of turns me on thinking about being used for money.” Hmm, I let that thought linger as I started to think about the possibilities. “Maybe one day Cindy. And I thought your stretched asshole was enough sluttiness for you. Maybe I’ll sell you to the highest bidder and use that money to by Paul a blow up doll.”

“Fuck you Jake. Really, fuck you!”

I ended up leaving shortly after, mind full of devious ideas.

Source: reddit.com/r/gonewildstories/comments/ngzr95/my_fucktoy_opportunity_hits