Her Latest Challenge

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Husband challenged not to cum, cuckold anal experience.
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I remember the first time that I saw her. She was dancing in a club, each move she made was hypnotising, the flashing lights lit up her beautiful face, her big brown eyes and her long, curly brown hair. Her wide hips swayed seductively with the music and her chest seemed to heave and draw the eyes of every man and woman in the room. Somehow I found the courage to approach her, and even more surprisingly she agreed to dance with me. We drank and danced and talked.

She made it clear she wasn't looking for a relationship, and being eager to pursue any action with such a stunning creature, obviously I mimicked the sentiment. That night she took me back to hers and rode me like a toy, telling me exactly how she wanted it. It didn't just end as a one night stand, though nor was it a relationship. We decided that we would just live out our fantasies, just no strings attached sex. Because there was no fear of trying to impress a new partner we were both able to say what we liked sexually and how we liked it. Being so open was refreshing, exhilarating and I found myself asking things that I hadn't even realised turned me on. I also loved hearing it from her, instructions, commands, she was a sexual being and I was there to help service her.

Our fling continued and we spoke constantly, meeting to fuck and talking in between about things we wanted to try, positions, toys, places. Hearing her soft voice on the phone was enough to get me excited and she became all I could think about: her curves, her thick lips, our amazing sex.

Despite our initial intent we began to fall into a relationship, but were mindful of the fun we had exploring and being open sexually. In such spirit we still talked about our fantasies and regularly experimented and Amanda is now my wife. Even as an established couple we still explore and experiment, fucking in public, role play, bondage - I even managed to invite one of her friends for my first ever threesome. We had always said that we would be open to involving others, as we knew that it was purely for sexual gratification and wouldn't have an impact on our marriage.

A couple of years into our marriage we began giving each other sexual challenges as a way of keeping up the experimental nature that we had developed. They began simple, but being in control of each other's experiences and releases gave its own pleasure, and of course they began to be more and more creative.

She always managed to surprise me, and this is what I thought about as I drove home; I considered what my wife had told me, 'Keep an open mind, I've thought of a challenge that hopefully we'll both enjoy." I had tried to predict what it may be, based on what we had done before, but I really wasn't sure this time. What I did know was that, just like all the other times, a challenge would need to be repeated until it was 'passed'.

I pulled up to the house, Amanda's car was already parked and the door unlocked. She greeted me in black lingerie, a corset style bodice showing off her amazing curves, brunette hair falling over her bare shoulders, stockings drawing the eye to the pale skin of her thighs.

"Hey honey," she whispered as she nibbled my ear, "I've got your challenge all ready, have a shower and come visit me upstairs." She slowly walked away, hips swaying hypnotizingly, my eyes following her beautiful ass as she climbed the stairs and disappeared around the corner.

I snapped back to my senses, realising that my cock was already straining against its confinements, I began unbuttoning my shirt as I hurriedly paced towards the shower.

Shortly after, I climbed the stairs in just my towel. I approached the bedroom but I paused as I could hear hushed voices, the second voice was deep and distinctly male. It caught me off guard, it made sense that a threesome would be something that she would want to do, especially with another man as we had already tried it with a woman, but how would this be part of a challenge? Last longer than him? Make her cum more times? My head was spinning with ideas, conflicting feelings of arousal and jealousy. Before I stepped into the room, I took a deep breath and promised myself that I would keep an open mind and fulfil whatever fantasy my gorgeous wife had concocted.

I stood in the doorway and took in the scene, my wife was sitting on the edge of the bed, leaning back on her outstretched arms behind her, legs crossed in a relaxed and sexy pose, she looked at me and gestured with her eyes to the man who stood near her.

"Honey, this is Chase," as she looked at him her eyes tracked him up and down, encouraging me to do the same. He was tall and clearly strong, not overly muscular, but he had a large frame that narrowed at the waist and split into two thick jean covered thighs. He gave a polite smile as he nodded towards me, running a hand through his short hair.

"Chase is going to help us with your challenge," Amanda continued, "I'm a lucky girl today," she said as she sat more upright, "I get to fuck both of you."

My cock twitched under my towel, stirring at the thought of fucking my wife with another man. However, I still did not understand the challenge, Amanda must have noticed my furrowed brow and continued.

"Your challenge is simple baby, you need to cum in my pussy". she paused and bit her lip seductively for effect, there was obviously more to come.

"You will fail the challenge if you cum before you are allowed to fuck me though," her lips curved into a sly smile "First Chase is going to fuck me whilst you watch."

Again she paused for effect, to let the words sink in, I was to watch my wife be fucked by this stud, all I had to do was not cum and then I would fuck her afterwards. I waited for her to continue.

"Once you've watched him fuck me, he's going to fuck you, after he's finished with you, then you can fuck me." As she finished speaking I felt light headed, I had not seen this coming, this was new. I had a few times played around and had Amanda stick one of her fingers up my ass as we fucked, the sensation was one of taboo and had been a fun experience, but I had never actually been fucked by anything, let alone anybody.

"So, all you need to do baby is hold your cum long enough to fuck me, simple" she whispered as she pointed to the chair that had been pulled close to the base of the bed, indicating that I sit. As I moved towards it, she slid off the bed and onto her knees, looking at me as she slowly unzipped Chase's jeans and unfastened his button.

"He's known as quite the stud. He popped a little blue pill so having the stamina to fuck us both shouldn't be an issue." She stopped talking as she reached in and pulled out Chase's cock, even I had to admit it was something to take in, thick and long and already hard and full.

Amanda licked the tip, and then wrapped her red lips around it. She began to slowly bob up and down, moaning to show her appreciation of his member. She cupped the balls and squeezed them gently and rhythmically as she fastened her pace, pushing ever deeper towards the back of her throat.

Chase looked down at her with an expression that was hard to decipher. He was obviously enjoying the gorgeous woman sucking his dick, but he looked hungrily at her as though she were prey, or a conquest he was preparing for.

He placed his hand on the back of her head and dragged her hair into a rough ponytail, using this as a handle to encourage the pace that he wanted. In response, Amanda moved her hands on to his thick thighs, bracing herself as her head continued to engulf the slickened member.

I realised at this point that my own dick was upright, as rigid as I had ever seen it and straining against the towel that covered it. I loosened the towel and let it fall off either side, allowing my dick to stand upright and unobstructed. It felt strange to be so aroused and not touch my own cock, I gripped it firmly but did not begin to stroke, the challenge had just been explained to me after all.

Chase was pulling her head in order to push his cock in, timing it with his thrust. Amanda's eyes were closed, pleasurable moans still emanating from her as she followed his lead. Her hair flowing along her back under Chase's firm grip.

Using his grip on her hair, he gently guided her to her feet, before stepping closer and using his body to push her back onto the bed. She landed lightly, feet raising in the air with her momentum. Chase grabbed her feet and raised them to his shoulders, resting them there in order to free his hands up to pull down her panties. He threw them on the floor near me. I could see the wet patch glistening in the low light, but my eyes didn't linger as I was again drawn to the scene unfolding before me.

The beast of a man was not one for foreplay clearly, after removing her panties he removed his own shirt in a fluid motion and stepped out of his jeans. He grabbed Amanda's thighs and dragged her waist closer to the edge of the bed, her hair sprawling above her. He grabbed his thick cock and aimed it at her pussy. He pressed it to her opening and between his hand and the weight of his body, pushed it into her in a steady motion. As he did this my wife closed her eyes and arched her back in a silent scream of ecstasy, taking his full length.

Unceremoniously, Chase began deep, pounding thrusts into my wife's pink pussy, gripping her legs for leverage. I could see his glistening cock pull out almost all of the way before pistoning in all the way to the base and repeating. He did not seem to care about her pleasure, he set the pace and thrust repeatedly into her. Amanda however seemed to enjoy being treated like a fuck doll to a well hung man. She was writhing with pleasure and seemed to breathe in time with each of his deep thrusts, her hands gripping the sheets around her. She pulled one hand towards her pussy and her fingers danced around her clit, right above her pink lips that were getting such a hard pounding.

It was during this point that I realised how entranced I was, without thinking I had joined in with their sexual gratification. I was actually enjoying seeing my hot wife getting fucked, being wanted, and seeing her loving every second. I had only just realised that the firm grip I had on my own dick was also stroking it, matching perfectly to the pace of their fucking.

Chase was watching her tits bounce as he drove deep into her, his own breathing was steady and deep. Her back arched once more and her toes curled as she was relentlessly pounded to orgasm. He did not seem to care that she was enjoying it, or even be aware that she was.

Suddenly he pulled out of her and stood upright. Amanda did not respond straight away, almost needing time to regain her composure and return to her senses after such a drilling, Chase however, did not need her input.

He grabbed her legs and used them to roll her onto her stomach, turning her so that her legs also rested on the bed. I watched my wife, lying there as her eyes flicked towards me and focused. She must have seen me stroking my cock as I gazed upon her and she gave me another sly smile.

Just as unceremoniously as before, Chase climbed on top of my wife and parted her legs with his own. Grabbing his cock and aiming it at her ready, wet pussy, he slid it in as she lay flat on the bed. Once he was in he thrust in deep and laid his chest upon her back, pinning her completely under him, one of his arms supported his weight as the other slid under her neck and gripped her in a loose headlock. Once happy with his position he resumed his fucking, pushing her hips into the bed as his own body arched with each thrust.

Amanda's face was being lifted by Chase's arm and was in clear view of me from my chair. She looked like she was in a daze, a blissful mindlessness caused by the deep fucking that she was receiving. She looked as though she had submitted in both mind and body. Her face seemed to wash with endless orgasms.

I couldn't have looked away even if I'd wanted to. She was a goddess, her skin seemed like porcelain in comparison to his tanned skin, her soft hair seemed more delicate next to the coarse ones of his arms, her body was curvy and sexy as the beast rode her, pumping her into the springs of the mattress that cried out against the assault.

Watching several minutes of this, I was too in a daze like watching a hypnotist's swinging timepiece, but instead it was the rhythmic fucking of my wife. I realised that I had been stroking my own aching dick, faster and more frantically than I had realised or intended and my own orgasm had been building. My brain seemed to fight between the instinct to blow my load to the hot scene in front of me and the gradual realisation that I had a challenge to complete.

In the time it took for me to grapple my mind back under my control it was too late, despite the fact that I had removed my hand from my throbbing dick and clenched my fists in a vain attempt at control, I was past the point of no return. My dick continued to throb as the inevitable sensation grew, culminating in a strong orgasm that spewed my cum over my thighs, stomach and dick. It seemed to continue as each pulse of my dick oozed cum as I squirmed in my seat.

All the time Chase continued to pound my wife's pussy as she cried out in pleasure.

Amanda smiled as she took in the site of my cum splashed over me from watching her fuck, which seemed to once again tip her over the edge and rock her body with another orgasm. Her body bucked under Chase as best it could, but he did not break his pace or even notice. He was himself picking up speed, and began to grunt as he reached his own release, his last orgasmic thrusts pounding his dick deeper and deeper as he shot his load inside of her.

As expected of the stud, he simply pulled his dick out of my wife and stood up, he looked over at me as if noticing me for the first time since my wife swallowed his dick, and cast his eyes down over my crotch to take in this sight of my own seed sprayed all over me, marking my defeat. He gave a semi shrug and began to gather his clothes.

My wife's face did not match the sentiment of her words, "Such as shame, you failed. This means that we will have to try again next week." She bit her lip and lay back limply on the bed, exhausted in post orgasm bliss.

The event ran through my head hundreds of times over the next week, how excited it made me, how I lost control. I had failed the challenge. I had caused the night to be repeated. Amanda had playfully teased me of course, and refused to have sex with me until the challenge restarted in order to keep me pent up.

Amanda was true to her word, she had set up another visit from Chase, and the day had finally arrived. Once again I drove home and, despite knowing the details of the challenge to come, I was just as nervous as last week. I arrived home and was greeted by Amanda again, although this time she was entirely naked. She gave me a kiss and an exaggerated blush as I took in her form. "I thought it might save him some time," she said softly as she pressed herself against me, kissing me gently. "Get yourself ready, you know where we'll be." Her hips rolled as she walked away, my dick stirred as I recalled Chases' firm hands on her soft skin, her moans echoed in my head and the sound of the relentless pounding, and then the image of my cum covered cock.

I shook the images out of my head and walked towards the shower.

After I had finished showering, I left the towel as I headed towards our bedroom. I had to remind myself it was my bedroom because as I approached it I could already hear the unmistakable sound of slapping and moaning, by the time I stood in the doorway to take in the sight my dick was already at full attention.

Amanda was on her hands and knees facing the chair at the base of the bed, Chase was behind her grabbing her hips with his large hands and fucking her from behind with deep, slow thrusts. Her face was contorted with pleasure, eyes shut tight and mouth open. Chase must have seen me, but he didn't stop or slow down. After a moment Amanda opened her eyes and saw me standing there.

"Baby," she said breathlessly "We thought we'd make it easier on you and get started." As she said this Chase removed one of the hands grabbing her waist and leaned forward, using it to grab her hair. He pulled on it and lifted Amanda's face, using both hands to pull her body back into each of his thrusts. She moaned with renewed pleasure, and it seemed like that was the end of our conversation.

I moved slowly towards the chair and sat down, facing the fucking pair. It felt familiar, my dick was swollen and begging to be touched. I fought the urge. My hips wanted to join in with the same rhythm in which Chase was fucking my wife, my hands wanted to fondle her tits, kiss her, slip my dick in her mouth. Instead I sat, fighting temptation and watching Amanda's eyes roll as she lifted one of her hands to find her clit. She was in the throws of an orgasm, legs wobbling, chest heaving and as I looked on I felt my own dick throb.

Chase was breathing heavily, his body like that of a machine in its repetition. His hands held her in place as he fucked her to the base of his cock, each thrust being marked with a slap as their bodies met. I couldn't help but consider the next part of the challenge, with this being me under him, his dick thrusting into my ass, us creating the slapping sound as Amanda watches on. I imagined his strong hands holding me in place and pulling me down each time he impaled me. I realised I had gripped my cock and was stroking it, removing my hand as soon as I realised, noticing the bead of precum forming at the tip of my dick.

A whimper brought my attention back to the bed, Chase had lunged forward and once again pinned Amanda under his own weight, thrusting faster and more frantically than before. He began to moan gently with each of his thrusts, Amanda's own cries of pleasure were muffled by the sheets and Chase's own moans, he began to thrust faster and faster, sweat beginning to glisten over his body as he gripped her tightly, he lifted his own head as his own orgasm swept over him, blowing his load deep inside my wife's pussy as his last thrusts slowed.

He lay on top of her, their breathing laboured. Chase lifted himself up and moved off of Amanda, allowing her to lift herself to a kneeling position.

"That's how he's going to fuck you," she panted, biting her lip, "like a dog. Come here, let's get you ready."

I stood slowly and approached the bed, her hand took mine and pulled me on to it. As she pulled me forward she sat back against the headboard, she leaned in, grabbed me under the chin and gave me a long, deep kiss.

"Stay just like that," she said as she cast her eyes over my naked form, now on my hands and knees with my ass in the air, vulnerable, "I'll be here the whole time."

She leaned back and blew a kiss as I heard footsteps approaching me from behind, the same strong hands that I had witnessed grip and hold my wife, clamped on to my waist and pulled me back towards the edge of the bed. My dick was still hard, and swung beneath me with the sudden movement. I felt a warm trickle of moisture on my anus, and a strong finger rubbing it around slowly, then pressing firmly into me. My back arched with the sudden intrusion, his other hand pulling me back instantly. He removed his digit and I looked over my shoulder as I saw him grab his cock and line it up to my entrance. I felt a pressure where the rubbing had just been that felt many times larger than the finger, it felt too large to be able to ever fit in, the idea that he may not actually be able to get it in began to form in my mind. This was quickly put to an end as he thrust forward, pulling me back at the same time. His cock slipped into my ass as I felt the pain of stretching, and the fullness of his dick inside me. He slid it in until I felt my ass touch his body. He left it there for a moment, seemingly allowing me to adjust, before very slowly pulling it back to the point it was nearly out, then pushing it slowly back in. I looked up at Amanda, who had a smile on her face and a finger rubbing her clit. As I looked at her I became conscious of my own expression, open mouthed and wide eyed, trying to grasp the new sensations running through my body.

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