“I’d never be able to live it down, Jacky,” he told her. “I’m just too scared.”
Jacky promised she would find a way to help, and she reminded Ted about the vibrating prostate stimulator they had bought so long ago. It was still sitting in its wrapper in the bedroom closet, and Jacky told her husband she would be happy to take it out and warm his butthole up. Ted agreed, but he said he wanted some finger play first. So, for the first time in what felt like forever, Jacky and her husband got naked in bed together. Jacky lubed up her finger and squirted a nice dollop onto Ted’s hairy asshole. She started with her pinky, and inserted it tenderly and gently into her husband’s tight bum. He was gritting his teeth and Jacky could feel his whole body tense in resistance.
“Relax,” Jacky whispered to him soothingly. “The more you fight the more it will hurt! You have to just relax your body into it. After all, I know you have taken dumps that are wider than my finger, honey.”
Ted relaxed, and Jacky slipped her finger inside of him. His butthole was tight and smelly, and it released a rank, sweaty odor as Jacky pumped her finger in and out of it. When he seemed comfortable, she moved up to her index finger, and then two fingers. Ted seemed to be enjoying it. His cock was growing and slapping up and down on his belly like a horny animal.
“Eat it out,” he asked her.
Jacky grimaced and almost threw up, there was no way she wanted her face in that smelly, hairy rectum. Besides, she hated the taste of lube on her tongue.
“I’ll let you use the prostate stimulator if you lick it a little bit. Come on, now,” Ted implored her.
Jacky agreed. Taking a deep breath and trying to close off her sense of smell and taste, Jacky gave Ted’s butthole a few quick, hard tongue licks. Ted moaned in delight. Jacky was glad her husband was happy, but she honestly couldn’t take anymore.
“That’s all I can stand dear,” she told him. “I think you need to shave and wash your bum before you try this with anyone else.”
Ted promised to do so, and Jacky brought out the prostate stimulator. It was thin, about the same width as her thumb, just a bit bigger, but it was much longer than her fingers. It slipped into his asshole easily, and Jacky pushed it in deep before she turned it on. Ted’s dick snapped to attention as the pleasant vibrations reached his prostate. He had a super boner, and Jacky was feeling quite horny just looking at it. In fact, she found herself actually wanting to suck Ted’s dick as she looked at it, hard and red and so desperate for some affection.
Jacky sucked Ted off, and he came a fat nut in her mouth. His orgasm lasted for almost a minute, longer than it took him to nut, as the prostate stimulator had penetrated to a new level of sexuality.
“I guess I’m just a horny old goat,” Ted laughed. He squeezed his cock at its base and got all the remaining drops of cum out. He had Jacky lick them off.
“That was nice, now wasn’t it?” he asked her. The two fell asleep together, cuddling naked in bed, and Jacky felt something close to happiness and love for the first time in a long time.
The next day, when Jacky was getting pounded out by Simon, she thought back to how good it felt seeing her husband’s dick long and hard like it had been when they first met and he was so horny for her. She was excited to make his dreams come true. When Simon had finished and was enjoying a post-sex brew, Jacky approached the subject with him.
“I was wondering if you might enjoy taking my husband’s anal virginity?” she asked him.
Simon was silent, thinking about it for a while. “Well, Jacky. I’m not gay. So, I guess I am not super thrilled about fucking a dude’s butthole. On the other hand, your husband gives wicked head and I like fucking you a lot, so I am inclined to say yes.”
“Oh, that’s great!” Jacky gushed.
“But,” Simon interrupted her, “I need you to sweeten the deal a little bit.”
Jacky agreed, and Simon told her that he wanted to fuck both husband and wife anally. “And I will come inside of you, my dear,” he told her and gave her a light kiss on the forehead.
Simon told her to give him a ring whenever the two of them were ready, and Jacky agreed.
It was time for her and her husband to start some anal training.
I Like Butt
Ted and Jacky were moving on to the medium sized butt plug in their anal training kit. The two of them were both giggling and having lots of fun as they squirted lube on each other’s buttholes and braced for the stretching sensation.
“Ow,” Jacky complained as Ted roughly shoved the butt plug into her tender asshole. “Be a bit gentler,” she told him.
She reciprocated by inserting the butt plug into his ass roughly as well. Ted didn’t complain verbally, but he let out a sharp snort.
As usual, whenever butt stuff came into play Ted’s dick was hard as a rock.
“Let’s fuck,” Jacky suggested. To her surprise, Ted agreed, and he gave her an excellent pounding, bringing her to orgasm several times. It felt so good to cum on her husband’s hard cock, somehow it felt better and purer than fucking around with Simon. Jacky kissed Ted when he was done, and the two fell asleep with their butt plugs in.
When it was time to move onto the last, biggest butt plug, both of them had quite some trouble. No matter how much lube they used, it just would not fit. Finally, Jacky decided that they should each try to sit on their respective butt plugs like an egg.
“Just go nice and slow and ease it in, who cares how long it takes?”
The two of them made quite a funny looking pair as they sat on their black plastic dildo eggs, trying to wiggle them into their butt holes. Finally, after a few minutes of struggle, the plugs were in. They were both feeling too full and strained for any sexual activity, but Jacky called up Simon as promised and let him know that they were ready for their anal threesome whenever Simon had time. He promised to come over the Thursday, when Ted had the day off, and they would have a good time of it.
Ted got excited thinking about finally losing his anal V-card, and he started to masturbate. He let Jacky watch, and she ate his nut when he was finished.
Keep Doing That!
The big event had finally arrived. Ever the good wife, Jacky had set up some drinks and chip and dip on the kitchen counter, and she had light, calm jazz music playing on the speakers throughout the house. Both she and Ted were dressed up nicely, as if they were about to host a regular house party for some of the neighbors. Ted seemed visibly tense, and Jacky was plying him with beers to try to help his nerves.
When the doorbell rang, Ted almost jumped through the ceiling. Jacky laughed. She poured three shots for everyone to calm things down. To be honest, Simon was looking a bit uncomfortable too.
No one wanted any of the chips and dip, but they all sipped on a beer and enjoyed one last shot before heading to the bedroom, where Simon promptly whipped out his large member and had Jacky and Ted get to work sucking on it. Ted held Jacky’s hand as they both knelt on opposite sides of Simon’s cock, giving the big beauty a nice work over. Ted sucked sloppily on Simon’s balls, until Simon instructed him to start fingering his own asshole. Ted removed his pants and went over to the bed and started sticking his index finger in his loosened bum.
“Keep doing that, jerk yourself off too if you want. I’m going to start on your wife first,” Simon told Ted. He bent Jacky over the bed, moved her panties to the side, and inserted his hard cock into her wet pussy. Jacky moaned as Simon fucked her, she watched as her husband stroked his cock to the cuckholding.
The moans suddenly turned into screams as Simon moved his cock from her pussy to her asshole. Despite all of the anal training, it hurt more than she had expected. Ted’s cock was throbbing and red. He chimed in with words of encouragement as Simon pounded his wife’s ass, one hand behind his back.
When he had tired of fucking Jacky’s butt, Simon pulled out his cock. He held it out in front of Ted’s face and instructed him to suck it clean.
“After all, you don’t want your wife’s b
utthole germs in your own asshole, right? Simon laughed as Ted slurped on his rusty trombone. “You suck cock soo good, Ted. I hardly even want to fuck your asshole, you suck cock so good.”
Ted’s eyes grew wide. The whole point of the evening was for him to lose his anal virginity, and now Simon was telling him he just wanted a blow job?
“Don’t worry man,” Simon told him. “I’m just fucking with you, dude. I’ll stick it in your ass if you get down on your knees and beg me for it.”
Ted did as he had been instructed. He kissed Simon’s feet and begged Simon to stick his fat white cock in his shaved, well-rinsed asshole. Simon complied, flipping Ted over on the ground and shoving his cock in fast and hard.
At first, Ted howled. His dick went limp, and he screamed in a mix of pain and surprise. But in a few seconds the screams had turned into moans of pleasure and Ted’s dick was hard as steel and dripping pre-cum as it whipped back and forth to the beat of Simon’s fucking. Jacky masturbated as she watched her horny husband getting his anus stretched out by the sexy frat boy. Ted was also jerking on his dick, pulling on it every now and again before stopping. He was dangerously close to cumming, and even a second or two of extra stimulation might push him over the edge.
Jacky got underneath him, and she put her husband’s dick in her mouth, sucking him off as he got filled up by Simon. His balls were clenched up tightly in his scrotum, and Jacky knew he was going to blow his load any moment. She tried to draw things out for him, but he couldn’t last much longer. After a few deep thrusts from Simon he blew a giant load in Jacky’s mouth.
Despite Simon’s promise to cum inside Jacky, by the time he pulled out of Ted’s asshole his cock was already blowing its load. He ended up with a handful of cum as he tried to intercept it.
“Well, shit,” Simon muttered to himself, “that was tight.”
After the group relaxed with some beer on the couch, Simon went back for seconds, drilling Ted’s asshole and blowing his load deep inside of it. Ted cleaned up Simon’s dick with his mouth, and the younger man gave Ted a brotherly pat on the head.
After Simon had gone home, Ted and Jacky were talking to each other.
“So, was it everything you expected?” Jacky asked her husband.
“Yes, it was great. It hurt so much at first, but just for a minute and then it felt wonderful. I thought I was going to blow my load right away, I am surprised I held out as long as I did,” Ted told her, smiling as he recounted the evening’s shenanigans.
Jacky cleared her throat, and then she asked her husband what had been on her mind for a long time. “Does this mean you are gay, honey?”
Ted laughed loudly. “What are you talking about?” he asked her naively. “We are married! How can I be gay when I have a beautiful wife and a family? You must have lost your mind.”
Jacky began to cry. She told her husband that she felt like he wasn’t really attracted to her anymore, and she had met Simon online since she wasn’t getting her needs fulfilled at home. The past few weeks, when Ted was giving random guys blow jobs while Jacky watched, and when they were doing their anal training together had been great, it had felt like old times. But, now that he had lost his anal virginity and had some confidence with men, Jacky just didn’t know what there was that was keeping Ted around. She asked him if he wanted a divorce.
Ted hugged his wife and gave her some tender kisses on her face. “I wouldn’t leave you for the world, babe. I don’t know what it is. I work with all men, and you know I have never really had any female friends. I don’t understand women, and I have no clue how your minds work or how to get you off. But I understand dick, and I guess I am pretty good at giving blow jobs.”
“You are great at giving blow jobs,” Jacky interrupted.
“Okay, I am great at giving blow jobs,” Ted agreed. “But, I love you. That’s why I married you. Sex is just a thing to enjoy for a little while. You bust a nut and then it is over. But you are forever. You are my best friend. I wouldn’t feel right coming home to some dude cooking me dinner. I’m just not that kind of guy.”
To be honest, Jacky was a bit confused. But she wasn’t unhappy. She loved her husband more than anything in the world, and she never wanted to leave him. She had been feeling sad once all the good sexual attention stopped, but recently things had been fun again. The love and the passion was back, and even though Ted spent most of his time getting other dudes off, he and Jacky had the occasional good fuck and they were becoming even better friends. If this is how he wanted to live, that was fine with Jacky.
“I love you, babe,” she told her husband. “I want whatever you want. If you want to stay married to me and explore sex with men, I want to help you. I find it so sexy when you get a big boner, and I love watching you suck a guy off. I guess marriage doesn’t need to be conventional, it just needs to work.”
Ted agreed.
From that day on, their marriage flourished. For a long time, Ted and Jacky kept up their threesome relationship with Simon. Despite his initial reluctance, Simon was quickly coming to favor Ted and one day he surprised everyone by sucking Ted off. Eventually, he let Ted fuck him. It was a real ordeal, and Simon hadn’t gone through any anal training or anything. It took a while for Ted to shove his fat member inside of Simon’s asshole. Luckily, the frat boy had plenty of liquor in his system and the whole thing was agreeable to him. Jacky enjoyed watching all the gay sex, and she jerked off, got some dick from Ted or Simon, or swallowed a load whenever the two had time for her. She also continued her game of picking up random store clerks and strangers when she and Ted were out together. Eventually, however, Simon graduated and moved away and the random hookups had gotten a bit dangerous. Ted and Jacky were now pretty well known in their local community for being some sort of sexual deviants, and they had to watch out so they weren’t charged with public indecency or any sort of crimes.
Things had gotten a bit boring again, and Jacky was starting to despair. She couldn’t think of any fun new things to do, and without Simon intimate house sex was few and far between. Then, one day, she and Ted saw moving vans pull up to the house next door to them. They were getting new neighbors. It was a handsome young couple: a sexy housewife with a huge rack and a nice ass and a tall, clean cut husband whose dick tip dangled out of his shorts dangerously as he bent down to lift up the moving boxes. Both Ted and Jacky liked what they saw, and they decided that a great new way to spice up their marriage would be to seduce this new couple and turn them out. Variety is the spice of life, after all, and the most important ingredient in a healthy marriage. Jacky had learned as much from trying to figure out Ted.
Ted and Jacky sauntered out into the yard, and greeted their new neighbors. They invited the couple over for champagne and a roast that night. The couple agreed, and Jacky and Ted headed back home to get ready, both of them had giant smiles spread across their face.
The End.
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