When a simple dare becomes an obsession, it can quickly get out of control EXTREME DEPICTIONS WARNING
When a dare becomes an obsession.
DO NOT READ THIS IF YOU ARE NOT INTERESTED IN EXTREME SITUATIONS -
I am not sure how to start this story. It is difficult for me to admit that this is now our new reality for me and my young wife. I guess the only way is to start from the beginning and dive into it.
My lovely, innocent wife, who I will call Jan, became my bride soon after we both graduated from college. We dated for two years and did not have any interest in having a big wedding. We eloped and got hitched as soon as possible. She is about 5’2”, barely 110 lbs, and has amazing breasts for a small girl. She has medium brown hair with sun highlights that is about shoulder length. Her ass is boyish (tiny) and her legs are to die for. She is the complete package. You can understand why I wanted to get her legally entangled with me as soon as possible.
Her college roommate for a year, who I will call Jill for this story, quit school and got married before we did. I always had the hots for her roomy. She was similarly built to Jan, and I think they shared each other’s clothes all the time. I secretly hoped they’d share boyfriends on occasion too, but sadly, that never happened.
Whenever the two girls got together and had a few drinks, the craziness would boil out of them. They fed off each other and goaded the other one into activities that I would never believe that my girlfriend, and now wife would ever dream of doing. One time, at a pool hall, while we were still in school, they bet with each other that they could make the next pool table of guys playing to lose to them in a pool game. They challenged the guys to bet $100 that the girls could beat them. It was game on, of course, since those guys were not about to let a couple of cute girls beat them.
The boys let the girls break first, and Jan sunk a ball on the break. She missed the next shot. One of the guys made his first shot, but Jill decided to start her distraction plan. As he lined up for his next shot, she stood in his line of sight and began to slowly remove her top. He missed an easy shot. It was Jill’s turn, and she made the next two shots before missing. The other guy had his turn and again, as he lined up for his first shot, Jan slowly pulled off her top too. He missed it also. The game went on, and both girls were now topless, and were being insanely distracting to these horny college men. The girls ended up winning and pocketing the $100. The bet between Jan and Jill was one dollar.
This type of crazy sexy gamesmanship continued between the two girls whenever they got together. And I loved spending time with Jill and her husband because of it. He was a quiet guy who just let Jill do whatever she wanted. He never tried to curb her unusual sexual antics, and I fully supported him. I loved seeing Jill in various stages of undress when they did these naughty things together.
It got even more intense after we were married. Jill and Jan would dare each other to do things that other beautiful young married women would normally never do. Jill dared my wife Jan to pick up a homeless man once and see if she could get him naked. This poor guy did not understand what was happening, but stripped down an alley, with the hope that he would see her naked too. He was standing there in the dim light, buck naked, waiting for her to strip down too. She just laughed, took his photo, and ran off. She won her one dollar bet with Jill.
The idea of fucking around with homeless men became a common theme with these two. Jan dared Jill to suck a homeless guy’s dick. Jill took the bet, and they easily found a street guy who was willing to be flirted with by two beautiful girls. He may have been homeless and dirty, but he was not stupid. He played along. Jill told him her girlfriend wanted to see her suck him off. He found a quiet spot away from any witnesses and pulled off his pants and underwear. Jill squatted in front of him and grabbed his filthy penis. She pulled on it to get his blood flowing, and I would be damned if she didn’t start sucking him off. The guy was astonished. He grabbed her head and began face fucking Jill. I don’t know if she had planned to have him take control, but he soon was shooting a load of spunk into her mouth. She swallowed his load and continued to suck him clean. She popped up from in front of him, wiped her mouth off and thanked him for his participation. Jan handed her the dollar to pay the bet, and the girls giggled and trotted off back to the busy street.
Another evening and another excursion with them looking for a homeless dude happened a few weeks after Jill sucked that guy off. It was Jan’s turn to do a decadent act. She approached two or three street men in another dark alleyway. The bet this time was for her to let them cum on her face and she had to wear their cum for the rest of the evening. I was shocked that Jan took this dare. Me and Jill’s hubby were always away from the action in the past, but this time I needed to be right there to witness it for myself.
Jan told the guys some story that she had an unusual attraction for men living on the street. She told them what she wanted. She would suck them off, as a group, and when they had all been serviced by her, they would surround her and shoot their cum on her face. She could not get them to believe this was not some kind of trap, so she had to strip down to prove she was serious. She slowly pulled off her shirt, then her bra and handed them to me. She kept going. She shimmied out of her shorts and pulled off her thong and was naked to the world. I took those clothes from her too and she said “there, now do you believe me?”. The men dropped their pants and presented their growing erections to her for servicing.
I was astonished. To think that my lovely young wife was really going to do this was incredible. I could not find words to say. I was dumbstruck and just stood there, like a butler, holding her clothes. She kneeled down and grabbed the closest guy by his butt cheeks and opened her mouth. He shoved his erection into her mouth, and she slobbered all over it, like it was the best candy in the world. He rolled his eyes back and gasped as her tongue started doing magic to his member. She stopped before he got too excited and turned to the next guy who was standing right there.
She repeated her technique, and this guy was in heaven. He could not believe he was getting a blowjob from a beautiful stranger. She sucked and licked his shaft and managed to deep throat him. His stinking pubes were jammed right up against her nose as she clutched his ass cheeks and pulled him close. I would never have believed this if I were not standing there three feet from her. She retracted her mouth from his pulsing pecker before he could lose control and then she turned to the last guy.
Again, she licked and sucked him as if he was the love of her life. It made me question the times that she just half-heartedly sucked my dick. But I knew that she wanted to win the bet and anything she had to do was worth it. The last guy also stood there as he was being serviced. But as soon as he grabbed her head, she pulled his hands away and told him that she was in charge and for him to just enjoy it. He did.
After all three homeless men had been prepped by her incredibly talented mouth and tongue, she asked if they were ready to finish on her face. The first guy stepped up and shoved his dick into her smiling face and got her to add some slobber to his shaft. Then he pulled out and stroked himself frantically until he exploded with several spurts of jizz on her face. The first spurt landed on her forehead, and then the rest went on her cheeks. She kept her mouth shut so they would aim at her face. She wanted to wear as much cum as possible and not waste it in her mouth.
The second guy used the same technique and had her get him all wet with her saliva before jacking off on her too. He had an impressive load and there was cum dripping from her nose to her chin when he was done. The last guy face fucked her again, briefly, then pulled out and blasted her with his sperm too. He got it in her hair and forehead, and some went into her eye. She just winked at him. When the session was over, she stood up and thanked them by kissing each guy on the lips. They really weren’t thinking about getting cum in their mouths, or didn’t care, and they all were grinning big toothless grins.
Jan looked at me with a very satisfied expression on her face. I handed her the clothes and she slowly got dressed. She did not bother with her panties and gave them to the first guy as a souvenir. Jill was ecstatic. She hugged my wife for having completed the prurient mission and gave her a long, passionate kiss. Then she handed my wife the one-dollar bill. I was still speechless. I had no words to express what I had just witnessed. I assumed this MUST be the last dare that these two girls would attempt, since the idea of having a homeless guy’s filthy dick in their mouth had to be the most extreme act they would attempt.
We walked into a nearby night club after my wife finished dressing. She was careful not to rub off any of the jizz still glistening on her rosy cheeks. She had a glob of thick creamy cum on one side of her forehead and thick drabs still hanging on her chin. As we went inside the club, the bouncer stared at her, and then glanced a look at me, as if to say, what the hell? We went inside and found a table. Jan and Jill were giddy with the results and we all got very drunk. As the evening faded, so did the spunk on her face. It dried to a thin crusty film on her skin. She found a last glob of it in her hair, with her finger, and popped it into Jill’s eager mouth. Jill’s husband just looked at me and shook his head. He was as mystified as I was about this extreme sport the two girls were engaged in.
A few weeks after this incident, the four of us were again out partying together. You’d think I would have learned my lesson and gotten them away from this part of downtown, but my own perversion of watching Jill and Jan perform these lewd acts was overpowering. I even spotted a homeless guy for them to play with.
It was Jill’s turn to accept a dare, which was to actually lick the asshole of a street stranger. I could not believe this was even considered, but both girls were very excited about it. We left the bar where this dare was consummated, and Jill found the guy I had spotted earlier. The four of us calmly approached him. Jill told him in a manner of fact way that she wanted to suck his dick and lick his asshole. This guy was completely taken off guard and was very leery of participating. I don’t know what he thought would happen to him. Get busted? Go to jail and spend a night in a real bed? He finally accepted that this was not some sort of set up and said he would play along.
Jill stripped down and her hubby was the butler this time and held her clothes. Jan and I stood closely by so we could witness this vile act that Jill had agreed to. She was supposed to suck him off, but before he finished, she would eat out his dirty asshole. It seemed like no one in her right mind would lick the filthy ass of a homeless guy, but both Jill and Jan were panting with anticipation of this happening.
After Jill was naked, she began unbuckling the belt of her intended partner. He soon decided it was real and quickly pulled off his clothes. Jill kneeled down, as was the established technique, and began to suck his soft penis. It was not too long before her attention to him aroused him and he was hard as a rock. He fucked her face and buried his dick balls deep into her throat. He nut sack was dangling just beneath her chin. She carefully stopped before he had an orgasm and told him to turn around and bend over. He promptly did. She used both hands to spread his ass cheeks and buried her face in his nasty butt crack. She used her tongue to lick his asshole and all along his crack. Jill pushed her face in deep and inhaled the fetid aroma of a man who probably had not bathed or used toilet paper in months. I almost wretched as I watched her lick and suck him. She reached around and began to stroke his throbbing member as her tongue was still buried in his ass.
Jan, then got into the action and plopped down in front of the guy and started sucking his dick. In just seconds the guy blew his load in Jan’s waiting mouth. Jill spun him around and sucked the remnants of his cum from his softening dick.
Both ladies were all smiles from the decadent act. Jill stood up and started to kiss the homeless guy but he would have none of it. He was not about to kiss a woman on the mouth that had just rimmed his asshole. Jill was a bit miffed but got dressed and collected her one-dollar winnings from my wife. As Jan gave her the dollar she leaned in and passionately kissed Jill and licked her face. It was incredible to witness.
I presumed this was the last of these crazy dares, since it just could not get any dirtier, than what we had just witnessed. But as we drove home after this event, both girls were enthusiastically brainstorming what other vile acts they could perform. Jill’s husband and I were both still in shock and could not believe they had more perversions yet to experience.
The last of these events, which just happened a few weekends ago, was to be the craziest idea yet. But neither Jill’s husband nor I had been told what the girls were planning. We went to a bar to have a few drinks which was not far from the same downtown area where several homeless men gathered. The girls, by this time, felt completely comfortable with their little scenario of approaching a group and making their proposition. This time it was Jan’s turn to take the dare. And this is where I failed as a husband. I let my voyeurism control my good sense and let this happen.
This last dare was for Jan to have sex with one of the homeless men. To let him penetrate her cunt but not wearing any protection. No rubber. I just knew this really could not happen. Jan would get up close to the line but balk at actually allowing a homeless man to fuck her bare cunt. This was too far out of the realm of sensibility, even for these two ladies. My heart was pounding in my chest as we approached a group of street men.
Both Jill and Jan casually approached them. There were a few men that we recognized from previous encounters, so they pretty much knew something interesting was going to happen. Jill’s husband and I stayed in the shadows, and did not want to impede this, but the truth is that I did not know what to say anyway. Could I demand that Jan not go thru with it, even though I was confident that she wouldn’t anyway? I did not want to be the killjoy of this prurient activity, but I also did not want it to occur. I was torn with indecision, so I did nothing.
I could not hear their conversation since we were too far away. But it seemed like it was going the same as all the other encounters. The girls were very persuasive, and you could see that the men were beginning to go along with whatever was suggested. Then, as usual, my lovely wife Jan began to strip off her clothes. Jill joined her and stripped down to nothing too. This was a new wrinkle. Both ladies’ clothes were in a pile in the alley, and they were surrounded by several dirty homeless men.
It seemed like an awkward moment until Jan leaned up and kissed one of the guys. Her hand found his crotch and she began fondling him. Jill did the same and soon they were on their knees with naked men surrounding them. Both girls were giving blow jobs. It did not seem like this was quite the usual tactic.
Suddenly, Jan was forced to the dirty pavement and held down by one guy while another naked guy dropped to his knees and began eating her pussy. She grabbed his head and stroked him as he pleasured her. I was thinking at the time that I wondered what kind of head lice he probably had that she was now touching.
Jill was also soon flat on her back on the rough concrete alleyway. She was being held down as if she was forced to be there, which I could tell she had not been. Each woman was being eaten out by a homeless man feasting on her shaved cunt. Other men got down on the pavement and shoved their hard dicks into each girl’s willing mouth. The lights from a distant streetlight cast an eerie glow to the scene. I could see details of what was happening, but it seemed like I watched it in slow motion. It was like my feet were cast in concrete where I stood, and I could not make myself move. Jill’s husband looked at me and shook his head in disbelief. He was no better than me as far as not taking any action to stop this process. We were both caught up in the event as both of our wives were willingly assaulted by a group of homeless men.
I suddenly remembered that the dare was to have a homeless man fuck my wife with no condom on. I panicked as I realized that this now was a real possibility. These guys were not going to wear “protection” so they did not get a disease from these fancy white chicks. It served these girls right if they came away from this alley with only one or two STDs. I nearly threw up as I watched this unfold.
Almost like it was choreographed, the two pussy eaters crawled up and apparently penetrated each girl . I watched the expression on Jan’s face, as she sucked a dick, then felt the dick of another man shoved into her bare cunt. She pulled the dick out of her mouth blurted out familiar curse words that she uses as she is enveloped by pleasure. She was really getting off on this. I watched her facial expressions intently. It was then that my attitude made a 180-degree change. If this is what my slut bitch wife wanted, to be raped by a dirty homeless man, then I would let it happen. She deserved any diseases or infections that she caught by doing this dare. Same with Jill. She was totally captivated by getting fucked by a filthy homeless man and she deserved any disease she came back with.
Well, as you imagine, the sex did not stop with a single homeless man fucking our wives, as was the original dare. When one was done dumping his cum into one of the girls, he would crawl off and allow one of his buddies to continue the assault. There were additional participants who wandered up as this gang bang unfolded so I do not know how many men were involved in fucking the girls. I doubt they were keeping track. Every moment that I saw them they seemed to be lost in some kind of sexual nirvana. They could not get enough dicks to suck or sperm spewed into their cunts. I heard Jan bark to the next guy standing there to stroke his dick so he could get hard and fuck her.
My brain wandered away from the actual assault I was witnessing. I wondered what it would be like to let them into the back seat of my vehicle with all that sperm that would be leaking out of their pussies. I guess I am a cruel bastard for even thinking about that but watching them encourage another man to dump a load of jizz into them was infuriating at this point.
I eventually had enough. The street urchins who were using our wives as cum dumps needed to go away. The way I got that to happen was another behavior that I later regretted, but it was a spur of the moment decision.
To end the parade of homeless penises ejaculating into my wife’s well used cunt, I first told them enough was enough. They completely ignored me. So, I did what any loving husband would do to end a gang rape. I pulled out my own penis and began pissing all over the guy who happened to be lodged inside my wife’s cunt at that moment. I soaked him down good. Of course, Jan was under him and caught all the residual piss that ran off his back and head. She soon was covered by my piss, which mixed with the sweat and the grime that had been left by each homeless partner that she fucked.
Jill’s husband followed my lead and began pissing on her partner, and her too. He was just as upset as me and we both used our piss as a weapon to cool off the ladies who apparently were in heat. After we began our piss assault, the men backed off, grabbed their ragged clothes and blended back into the street scene from which they came.
Soon it was quiet, with only two naked ladies, lying in pools of piss, sweat and cum. Both girls were exhausted and lay sprawled out on the pavement. I tossed a garment to Jan and just curtly said, “time to leave”. I also pulled out two single dollar bills from my wallet and tossed one to each of them. “There, you both won your dares”.
I called an Uber and had the wives delivered home. I was not about to let their stinking bodies in my car. Maybe when I got home later they would be cleaned up and back to being normal. Jill’s husband and I went to a nearby bar and got shit faced. We did not even want to go home to deal with our wives. This ended their little competition of dares, at least as far as I know.