Fantasy Island

Ann's plan actually worked out against Brian. Without Greg's half of the rent, Brian had to find a new room mate, but nobody wanted to live with the slob. He interviewed a few candidates and had a guy move in with him for the last two months of Brian's lease. He managed to catch up on the rent, but the last weekend of the lease, the room mate took all of Brian's valuables, which were pawned for $235.

Brian had to pay for the damages to the apartment since he never carried renter's insurance. Greg never knew Ann plotted against Brian. He just surmised it all as bad luck finally finding him.

Brian got Bree pregnant and they tried to sue the condom manufacturer. They were laughed out of the lawyer's office.

Brian had to quit working for Ann. He moved across town to be closer to Bree. Brian got a job at the same grocery store thanks to Bree.

About 3 weeks later, Brian was fired for stealing beef jerky and condoms (so he could cheat on Bree). When the store manager found out about this, he told Bree.

She was so humiliated that she broke it off with Brian. She went out on the town with a few friends and had sex with two guys across town. She actually had a few orgasms in the process, and enjoyed having a threesome with two guys.

Brian came back to Bree and patched things up with her. The truth was, he had no place to go, and since Bree's sister had taken them in, it was the only arrangement they had.

Bree blamed Brian for the loss of the furniture, and made him promise to buy her the exact bedroom suite, and a crib before the baby showed up. Brian had to work at the grocery store AND take a job working weekends to save up enough money so they could get a place of their own before the baby arrived. Bree enjoyed herself for the next few months making quite a few trips across town to suck Jerry's cock, and to ride Allen's cock (usually at the same time).

She was still humiliated that she spent all those weekends fucking Brian, but she did still love him. When their baby boy came into the world, they both found focus and settled down. But Bree still gets text messages from both Allen and Jerry.

Ann left Joe and took half of everything she had ever bought him. She had the house sold, and gave Joe some "restart" money.

She and Greg lived in their apartment until Greg finished school. Greg started his practice as a physical therapist. They just bought a house on the golf course, where Joe mows the lawn and Brian caddy's to make extra money for their 3rd baby.

Brian is proud of Bree, she has done so well and is so important that she has to take trips across town every other weekend to help get another store going. Its the store where Jerry and Allen make her scream THEIR names while they pump her full of cum, but Brian doesn't need to know that, yet.

As for Jo and I.. things are moving in a different direction for us.

Ted had gotten Elaine to work out all of her frustrations and she decided it was not for her. They patched things up, and moved forward with their marriage. Ted and I have grown distant with nothing in common.

Joe and Ann had split up over this "lifestyle". Joe wanted it more than Ann did. Ann wanted something different, and she found it when she least expected it.

Now Joe is mowing yards and working odd jobs just to get by. The last we spoke, Joe said that Ann has a younger man in her life and she was doing well.

My wife Jo had exchanged numbers with her old college boyfriend Robert before he left town. He kept in touch and made it a point to returned to town.

When Robert was in town, Jo would leave on a Friday evening and she would come home on Sunday morning. I would have a long list of chores to work off before she returned. If I finished the list, I got to hear about how Robert satisfied Jo, and she would spare no details.

If I did not complete the list, I was denied the details. Jo would use this time to antagonize me even more, prolong my suffering and get me even more sexually frustrated. I learned that my eagerness made me do things I normally would not do, and Jo learned how to use that against me.

Robert had gotten very used to fucking Jo on a regular basis. In fact, he asked for a transfer but got denied.

Jo ALWAYS came home in a great mood after spending a short weekend with Robert. Jo had gotten really comfortable with sending me photos of Robert's cock in her mouth, his ball in her mouth, and his cock inside of her.

The photos usually matched the story she would tell about how well Robert met her needs. Robert had learned that giving Jo a week's notice of his visit would make her do more kinky things.

Soon it all became routine for Jo and for Robert, and that was when things changed.

This last visit, Jo requested two rooms in the hotel, side by side with a pass-through door.

I was forbidden to watch, but I was allowed other liberties.

I was stripped down naked, except for my chastity device. I was tied to the office chair in the room and then positioned by the pass-through door, with the door cracked. I couldn't see anything, but got to listen to Robert and Jo, and it made my cock strain against the chastity device harder than it ever had before.

After everything was in place, Jo walked into Robert's room and all I could hear were slurping sounds, and a lot of moaning. This lasted for several minutes until I heard Robert say, "Here it comes!!! YES YES YES.. Oh FUCK YES!!! MMMM.. So HOT.. MMMM.. MMMMM.. oh yes."

I figured out quickly that Jo had given him a blowjob, and judging by his vocal line, it had been a while since he had an orgasm.

Seconds later, Jo walked into the room. She was still dressed. Her lipstick was smeared. Her lips were closed, and there was a fire in her eyes.

Jo grabbed my face and kissed me. She used her fingers and thumb to force my jaw to open, and used her tongue to push a thick, salty load of semen into my mouth. She used her second hand to hold the back of my head, and used her tongue to make multiple passes from her mouth into mine. She shared Robert's load with me, then stepped back and watched me swallow it. Had I resisted, she would close the door and leave me in the room for house keeping to find then next morning.

Jo licked her lips and smiled with approval. She said nothing.

Jo lifted her skirt and pulled her panties off in front of me. I could see her nipples were hard. The chain around her neck and its key twinkled in the dim light. The act of sucking cock made her moist on most occasions. She had confessed to me before that sucking off Robert, made her wet as hell. She tossed her wet panties into my lap, covering my cage. I wanted to sniff them so badly.

Jo had made a few confessions to me before tonight. She had admitted that sucking cock while fully clothed added to the excitement for her. I remember her also telling me that if she sucks a man's cock with her clothes on, it "forces" her to swallow, and "do a neater job" than if she is naked. Her comment, "If cum drips onto my tits, that is okay if I am naked, but if I am fully clothed, it makes me want to swallow ALL of the load." Her words echoed in my head as I watched her strip out of her clothes.

Jo carefully unzipped her skirt, laid it on the bed, then removed her top. She had a skimpy black lace bra on that was a size too small for her chest. She left it on while she pulled her heels off. Lastly, she removed her bra and my cock twitched at the sight of her naked body. I had grown accustomed to seeing her naked with the key around her neck. She never removed that or her wedding band.

She walked over to me and grabbed the back of the chair, spinning me away from the door so I was facing the wall in our room. She pulled me closer to the door and in a loud voice, she asked, "Are you ready?"

"YES." Robert replied.

What happened next was both bizarre and unexpected. I was wheeled into the next room, Jo pulling the chair and leading me. Robert's cum was still smeared all over my face. Jo's panties covering my caged penis.

Robert was laying on the bed, naked. His cock was not completely soft, or completely erect. There was a dim light on across the room.

Jo positioned me near the corner of the bed, close enough to see well and hear well, but not too close (or too far away). Jo walked around the chair and leaned over in front of me. Her huge breasts rubbed against my should, her warm hand rested on my opposite shoulder as she whispered in my ear, "You stay quiet and watch, or this NEVER happens again. Only nod if you understand. Blink hard if you do not understand."

I waited for Jo to pull away from my ear, then I nodded.

Jo smiled and then stepped away from me and walked over to the bed. She grabbed ahold of the headboard, planted a knee on the mattress by Robert's shoulder, and then swung her leg over Robert's head. She lowered her hips to his face, and as Robert's tongue made contact with Jo's clit, she let out a sigh and a hiss all at once.

I watched in awe as Jo's hips sank a little lower, and as Robert's hands explored her body, Jo's hips moved against his face in a loving way that just looked like it felt good.

I heard Jo whimper and I watched as her body twitched. Her thigh muscles and her glutes flexed as she had a small orgasm on Robert's face.

After that, Robert grabbed both of Jo's ass cheeks and Jo used her shoulders to help steady her body. I heard her moan and hiss as Robert ate her married pussy for several minutes until Jo cried out (loudly). She used her hips to grind against Robert's face and she screamed, "Robert, Robert, Robert!!!" over and over as she climaxed. I counted six orgasms before I felt my head get light and found myself staring at Robert's cock, which was hard again, and Jo's ass as it flexed and relaxed several times over.

Jo rode Robert's face for a very long time. She was wet when it started, but now between the panting sounds Jo made, there was a sloshing noise that filled the room. Robert ate married pussy like a champion. Much longer than I ever remember eating Jo's pussy.

"Was this a lesson, or a display of what mistakes I had made in the past?" I kept wondering to myself.

Just when I thought the show was coming to a close, Jo lifted herself up off of Robert's face and rolled over on his opposite side. Jo kissed him. French Kissed him, tasting herself on Robert's tongue. She seemed to enjoy it.

After they made out for a few minutes, Jo got up on all fours in the middle of the bed. She had her ass facing the headboard, and looked directly into a mirror that was bolted to the wall. Robert stood behind her, paused and looked her in the eyes in the mirror. Then, by bending at the knee, Robert lowered his hips until his cock was lined up with Jo's married pussy.

Without hesitation, Robert slid his cock inside of Jo. He grabbed her hips to steady himself, and he pushed his cock all the way in, until his balls were resting against Jo's ass. The expression on Jo's face told the tale completely.

I knew she had found more pleasure in being with Robert, but now I could see why. Robert ate pussy better and longer than I did. His cock was bigger around and slightly longer than mine. The head was much bigger than mine. If THAT were not enough, Robert knew what positions made Jo cum the hardest, and the one they had invited me to watch was her favorite.

Robert knew how to fuck too. Something Jo left out of her detailed accounts since their first time together.

Robert pushed his cock all the way in and waited for the rest of Jo's pussy to open up, and it actually drove Jo crazy with desire. Robert would caress her skin, run his finger tips over her back and ass cheeks and it brought her pussy to life in ways Jo has never been able to describe. Jo watched my reaction. Looking into your own wife's eyes while a bigger, longer cock is buried deep inside of her pussy is a level of humiliation few reach, but here we were, fully engaged in the act and loving every second of it.

Jo turned her attention back to the mirror. She looked up at Robert. Robert knew she was ready.

I was unprepared for what happened next.

Robert grabbed Jo's hips and started moving in and out of Jo slowly. Jo whimpered as Robert's cock head "massaged" her interior walls, pushed against her clit, and bottomed out against her cervix. Robert "worked" his cock like a professional porn star. He sent slowly and first, which drove Jo into a deeper state of arousal. A few seconds later, Jo cried out in pleasure as an orgasm shot through her body, forcing her pussy to clamp down on Robert's cock.

After her pussy muscles relaxed, Robert started fucking Jo harder and faster. The sounds of skin smacking skin filled the room. Robert was forceful in the way he took Jo's pussy. His powerful legs and upper body rippled with each thrust into my wife. Jo's hips were taking a harsh pounding. With each "smack" that filled the room, the skin on her legs moved and Jo herself moaned and whimpered louder and louder with each of Robert's efforts.

"OHHHHHHHHH FUCK!!!!!" Jo screamed out loud as Robert continued to pound her pussy. Her married pussy never was treated like this, and I was finding out the hard way why that was a mistake I would never live down.

"Robert.. Robert.. Robert.. OH SHIT... YES YES YES YES YES... AHHHHHH." Jo screamed and chanted, nearly non-stop as Robert continued fucking at an impressive pace.

Sweat was running down Roberts face. He was panting hard. He was STILL on his feet. The angle his cock was sliding in and out of Jo was hitting all of her nerve endings, and it awakened her inner sexual being. Jo was moaning uncontrollably, screaming into the pillow from time to time, but also chanting Robert's name. She was having multiple orgasms on Robert's cock, and I do not feel any other cock would have done her any better at the time.

Robert sensed that she was close to another orgasm, and he looked and me and winked.

Then Robert stuck his thumb in his mouth, pulled it out with a heavy coating of saliva on it, and pushed it against Jo's asshole. Jo encouraged Robert to push it inside of her. Robert needed nothing else to be said.

I watched Jo's face as Robert's thumb slipped in past her sphincter. Her eyes nearly rolled back into her head. Robert used his thumb to hold Jo's ass in place, and then he started to fuck her again.

Robert's renewed vigor, and his "magic" cock made Jo tingle head to toe. Jo's enthusiasm to take his thumb in her ass made the moment hotter than before. I feel the fact that her husband was watching her have multiple orgasms with her college boyfriend (who's thumb was now in her ass) may have added to the situation for Jo as well.

I found myself wanting to encourage Robert to fuck her harder, but I am not so sure she could have taken it.

As Robert started pounding Jo's married pussy just as hard as before, he worked his thumb in and out of Jo's asshole at the same time.

Jo was screaming, panting, and moaning louder than before.

This did not last very long, and Robert told Jo, "I'm gonna cum. I am going to fill your pussy!!!! HERE is comes.. MMMMMMMMMMMMMMMMM FUCK YEA. MMMM.. Take it all Baby!!!"

Robert KEPT his thumb in Jo's ass the entire time, and as he shot his load inside of my wife, I watched her face.

Jo looked at me as Robert filled her pussy up. She had an expression of passion, fulfillment, pleasure, and satisfaction all rolled into one look, and we shared that while Robert emptied his balls into her.

Once Robert was done, he pulled his thumb out of Jo's ass, then slowly pulled his cock out of her ass.

Jo rolled to her side, and held her legs up in the air.

Robert walked over to the chair and pulled a single piece of rope. This untied me and I was "free" to stand up. As I stood, Jo whistled, and then worked her index finger in a "come over here" motion.

I knelt at the foot of the bed, and Jo moved her body to align with my head. She spread her legs open, crossing her ankles behind my neck and using her thighs to pull me in closer.

"EAT" Jo ordered.

A flood of memories and assumptions rushed through my head. Everything from the first Cuckolding story I ever read and how it shaped my fantasies to the wild details that I gleaned from that and other entries which had morphed into thinking about Jo fucking other guys with bigger dicks than me.

I never once considered simple facts like better techniques, more enthusiasm or increased stamina, and how it could be used to please her or fulfill her desires. These were lessons I was learning AFTER the fact, and this meant they were going to be painful.

Early on I only hoped she would learn to enjoy this fantasy, but never considered my part in the introduction, transition, or maintaining this lifestyle.

I thought about how I had beat off in the shower, in the garage, and in the storage shed numerous times thinking about my wife sucking the neighbor's dick.

I thought about how the simple act of flirting with strangers like Derrick, or people we knew would initiate my imagination and how I would chain together made up events and circumstances that usually ended with Jo having an orgasm with someone else. I thought about different positions, clothing, how to hide cameras, set up meetings, and how it would look (and feel) to watch my wife ride a different cock or to be taken by another man with a muscular build.

I envisioned her gasps for air, her moaning in pleasure, and the whimpers she would make with them while I watched.

I WANTED her please other men, and to be pleased by other men. I reminded myself how my own wife getting fucked by another man excited me, and that what I was about to do had to be done to prove I wanted THAT above all other acts or tokens of affection. I had to prove I wanted her to humiliate me to the extreme, and I had to prove I was going to hold up my end of the arrangement after the deed was done.

I closed my eyes, opened my mouth wide and stuck out my tongue. Jo held the back of my head and guided me up and down the warm and "leaking" slit of her pussy. She pushed my head down and squeezed, pushing out the semen that Robert had just pumped inside of her married pussy.

Robert watched as the white paste rolled out of Jo's pussy, landed on my own tongue, then disappeared inside of my mouth.

Jo moved my head and rolled her hips upward, forcing me to lick her asshole, then move to her leaking pussy, lapping up any and all residue, then she rewarded me by letting me lick her tender and sensitive clit.

Jo ran her fingers through my hair and moaned deeply as I cleaned her pussy up. "That's it.. take it all.." Jo hissed softly.

Robert's scent and his semen were all over Jo's pussy lips. "Clean the outside as well my Dear." Jo instructed.

Jo's fingers lovingly ran through my hair as I ate (cleaned) her pussy. I looked up at her and she was kissing Robert WHILE I ate her pussy. One of her hands was on the back of my head, and the other was on Robert's shoulder.

The humiliation of eating another man's semen from your own wife's pussy could only be multiplied by a few factors.

1) If you witnessed her taking that semen, and still went forward with the act.

2) If she encouraged you to do it, and critiqued your effort.

3) If the "donor" was still in the room, and was getting more attention than the husband.

4) If your wife ignored you WHILE you cleaned her.

I envisioned the site as it would look to a fourth person in the room. The idea made my dick strain against my chastity device. The scent of Jo's pussy was heavily masked by Robert's semen, but I knew my wife's juices were swimming in the fluids I tasted and drank from her.

It had been months since I had an orgasm. Jo was saving my "release" for something special. Tonight was full of new events and new firsts for us both. I was hopeful of having a release tonight, but was smart enough to NOT bring it up.