Breaking Matt and Dolly In

by mattwatt

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa, Ma/Ma, Romantic, Reluctant, Gay, Heterosexual, Wimp Husband, Wife Watching, Gang Bang, Interracial, White Couple, Hispanic Male, Oral Sex, Anal Sex, .

Desc: Romantic Sex Story: Matt and Dolly have an affectionate but sexually loveless marriage. As they enter their 50's, Matt realizes that he is indeed gay and Dolly is simply unfulfilled. Then there are the yard guys, who have designs on the lovely, but overlooked Dolly but realize that they need to 'compromise' Matt first. They set about that and it works, with Dolly as one of the main prizes.


The plan, which by the way worked like a charm, was actually Luis'. He was good at listening to people, watching them and deciding whet they were truly like, what they were hiding, kind of. In this case, he was sure that Matt was more than half way gay, at least 'gay curious'.Dolly, he thought, was more difficult, 'more tightly wound', was the way that he put it to Jorge and Manni. It made them laugh.He still thought that she could be reached, and reaching Dolly was Luis' main aim. He found her, older, ripe, and lovely and wanted to pursue the plan to get to her.

The plan was fairly simple.

"We turn them out," Luis explained,

"How, man?" Jorge wanted to know.

Luis laughed and said: "Very carefully! But it'll work, trust me on this."

"But that Dolly is an old bag!" Jorge said, the youngest.

"Are you shittin' me, man?" Luis answered. "Ever look at her, really look at her? Those tight jeans, not too tight but certainly not loose, kind of advertising that Momma has an ass worth lookin' at and she still wants to show it. Nice sized tits and that curly dark hair with some gray in it. Take her clothes off and get her revved up and she'll be all the Momma that you can handle."

Jorge laughed at Luis' enthusiasm and said: "Okay, man, I'll be lookin' and tryin' to see what you're talking about."

"Do that!" Manni said, "Luis is right about this one, about both of them."

Matt and 'Dolly'/Dorothy Winters were into their early 50's. They'd been married for 24 years and were comfortable with each other. The sexual 'fire' had certainly gone out of their marriage but there were at least some reasons. Matt was inflicted with a small dick. Standing up at attention it measured only about 4", and Dolly had for years privately referred to herself as 'Dolly the Unsatisfied', a fact that she kept strictly to herself.

She tended, Dolly did, to be a little strict with Matt, who could be kind of scatter brained. She suspected, at times, that Matt had a gay streak in him, 'maybe bi', she thought to herself but never wanted to test those waters. It had gotten to the point that leaving sex alone, except for a couple times a month, was fine.

Over the years their preferences had hardened. Dolly longed for Matt to 'fuck her well', as she put it to herself. That usually didn't happen. Matt loved to have his dick sucked and this was the one place that Dolly was willing to accommodate him.

She even thought it fun, kind of silly, that his little thing fit into her mouth so snugly, without causing any kind of discomfort. But Matt knew better than ever unload in Dolly's mouth. She sure as hell didn't like that and wasn't going to take it.

They lived a normal life, both of them working, church members, as a matter of fact, choir members at their church, and popular, for Matt was always funny and Dolly was a worker sublimating her sexual frustrations in business and the ability to organize and get things done.

Dolly was pretty much as Luis' had described. Still, at 53, a very nice, trim package of a woman. Boobs didn't really sag. She had large nipples and was vain about wearing fairly tight pants.

She had a secret love of watching men's butts. She never shared this pleasure with Matt, although if she had, she'd have discovered that it was a pleasure that he also enjoyed!

Currently, the hit in Dolly's life was the three guys, Luis, Jorge and Manni, who did their grounds work, trimming, mowing, raking in season and all.

Dolly was secretly pleased by how Manni wore his pants as 'low riders', with the belt around his upper thighs. She covertly watched, usually able to get a view of Manni's 'crack' and enjoying the sight.

Of course, when Dolly wasn't ogling Manni's crack, Matt was, thinking about what kind of 'meat' Manni might have, and just drooling over the sight of any or all of the three of them in their shorts, sometimes running shorts, as they worked, shirts off and sweaty. It made Matt breath hard.

Of course, Dolly noticed it and that kind of response in Matt tended to make her angry, set aside the fact that she was reacting to the same kind of views. At times, she simply decided to go shopping, when the three of them were due, unless a heavy spirit, a sensual one was on her and then she wanted to stay and watch, always keeping an eye out for Matt, so that he wouldn't notice her having this kind of visual pleasure.

Matt and Dolly Winters were both tightly wound in their own separate ways, and Luis could see through that. It was what his plan was based on, and today, a Saturday, was the day that the plan was supposed to be put into operation.

They went over it, the three of them and thought it would work. They had observed often enough to know that Dolly would be away for a good while, giving them the chances with each one, Matt and Dolly, that they wanted.

In talking about it, Luis even laughed and told Manni and Jorge about how he had seen Dolly staring at them any number of times.

"Shit, man," he said laughing, and talking to Manni, "When you hunker down and your pants ride low on your hips, I can hear the two of them sighing at the sight of your ass cheeks that you give."

The others laughed at that thought, image.

"This is gonna be so much fun!" Luis said.


They were all pleased, when they got to Winters' home to do the work, to see that Dolly was indeed leaving. They smiled and waved at her, giving her a breezy 'Mornin' Mrs Winters' greeting. She was, as usual, wearing a pair of those snug jeans.

"See, dimwit!" Luis said. "Look at her wiggly butt!"

"Yeah!" Jorge said, realizing that Luis had a point.

"I guess!" Manni said. "This is all gonna be fun!"

"The fag first," Luis said, "And then we go on a hunt for Dolly. She usually ends her shopping at the 7-11 down on Wayne. We'll try to get her there. Good spot. Room around it and isolated enough."

"Cool!" Manni said.

They went to work, after greeting Matt, who was, as usual, flamboyantly glad to see them and effusive in his greetings. They did their work quickly, shirts off and sweaty. They could see Matt peering at them through the curtains of the family room. It made them chuckle.

"He's ready alright," Jorge said, and both Luis and Manni nodded.

They got the work done and the clean up done and then went into the shed to clean up the machines that they used. They always used the Winters' machines. In the normal course of days, Matt would always join them in the shed sooner or later. The timing was usually a matter of the amount of time that Matt could wait to get his major thrill of seeing they 'boys', shirts off, still sweaty and maybe hunkered down and showing some butt cleavage.

The three of them were working at the clean up, when Manni, looking out the window said: "Here he comes!"

"Remember the plan!" Luis said.

They turned their backs to the door, with Luis standing near the door and working on the blower machine, Jorge working on the rakes, and Manni hunkered down and working to clean the mower, showing the 'cleavage' that Matt was interested in.

In preparation, Manni had pulled his cargo pocket shorts down a few more inches, so that, when he hunkered down, he was showing an expanse of pristine white boxer tops and a good 2-3 inches of butt crack.

When Matt entered the shed, saying a breezy 'hi', he sighed involuntarily, and stared at Manni's crack. The plan had begun.

It was Luis who moved, getting over to Matt and pushing the door closed.

Matt was still entranced by the sight of Manni's ass hanging out, when he was surprised by a vice like hand gripping his neck.

"Like that, Mr Fag?" Luis said barely above a whisper.

"Hey," Matt said. "Let me go!"

"No way, man," Luis said, "Until you tell me that you like the sight of Manni's ass!"

Matt struggled a bit but soon enough realized that there was no way that he could get out of Luis' grip, which was tightening and becoming painful.

Matt was not a fighter, he wasn't particularly brave, didn't mind being ordered around by his feisty wife, and in this case, as the pressure on his neck increased, simply gave into what he was indeed thinking.

"Yes," he said, sullenly, "I like the sight of Manni's ass."

"Say it again!" Luis said.

Matt repeated the phrase. Luis squeezed, and Matt winced.

"Say it nice, Mr Fag!" Luis said, and Matt complied, saying in a very nice, pleasant voice that he liked the sight of Manni's ass.

"Say it to Manni," Luis said next, enjoying this immensely. "Say it nice to Manni!"

Matt did: "Manni," he said, with Manni turning around and grinning at him, "I like the sight of your lovely ass!"

"More like it, bitch!" Luis said.

With the language and the pressure on Matt's neck, showing him that they might indeed hurt him, if he didn't comply with what they were saying, asking him, ordering him to do, Matt was losing control totally, if he ever had any control of the situation or over these three.

Luis walked him forward then to right behind where Manni was still hunkered down.

"Get down on your knees!" Luis said, putting pressure on Matt's neck.

Matt went to his knees, now kneeling right behind Manni, staring down at Mannis' ass crack, now close to his face. Luis pushed on Matt's head and said in a whisper:

"Get your mouth down there, Mr Fag! Get your mouth down there and lick Manni's crack. Don't even think of not doing what you're told or the ass kicking begins now! That what you want? Us to kick your fag ass? Kick it good? Break you up a little? Cut you up?"

.... There is more of this story ...

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