by Budman

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© Copyright 2022 - Budman - Used by permission

Storycodes: M/f; bond; tease; denial; mittens; oral; anal; toys; shop; cuffs; incest; teen; cons; X

Continues from .

Author's Note: These chapters will make almost no sense if not read in order. If you haven’t, I strongly suggest you go back to the introduction and chapter 1.

This chapter contains a flashback to Jill and Bob’s earlier life. Enjoy.

Chapter 6: Oral, NY and Graduation

Life returned to ‘normal’ whatever that was. Jill survived her two-week Mitt sentence and probably enjoyed more sex than normal. Seeing his wife in the Mitts, eating off the floor, really turned Bob on and that frequently resulted in some after dinner sex of one type or another. Sometimes it was a blowjob, sometimes anal but about once a week, Jill got a good, old-fashioned fucking and that was worth waiting for.

After her “mitts” sentence was served, Bob decided he wanted to see if he could drive Jill to masturbation, and so, he embarked on an almost month-long period of edging, butt fucks and blowjobs. One evening he came down after dinner, handcuffed Jill’s hands around the pole behind her back and proceeded to tease her clit for almost an hour with a vibrator. By the end of the hour, she was covered in sweat and shaking from frustration. Bob then implied that if she gave him a REALLY inspired blowjob that he would finish her, but of course her blowjob wasn’t good enough despite Bob blowing a huge load down her throat. Bob left her handcuffed to the pole until bedtime with cum drying on her chin.

“It really wasn’t fair”, Jill thought. She KNEW that blowjob was good, one of her best. She did best when she could use her hands along with her mouth, but she also knew Bob preferred her to either lock her hands behind her or order her not to use them. Bob loved to make her work for his cum, and he also loved that it took longer when Jill could not use hands.

Bob knew it was a good blowjob too, his legs were almost too weak to walk up the stairs. His lovely soccer mom was one hell of a fellatrix. She had never quite mastered a balls-to-the-chin deep throat but Bob doubted she ever would, some women just had too strong a gag reflex.

Bob thought back to that New York City trip they made for their first anniversary. Bob had just received a nice sales bonus. He should have saved the bonus for their first house, or any number of other expenses but he decided to splurge. He bought airline tickets, three nights at a nice hotel and tickets to two plays. It was on the way home from one of those plays, at almost midnight, that they passed one of those seedy adult video stores off Broadway.

“Let’s go in!” Jill exclaimed and yanked Bob inside before he could object. Thank god she didn’t want to go into the back where the booths were. But she walked up and down each aisle picking up and looking at VHS covers.

“Ooow, people DO that?”

“How do they get that many people in one bed?”

“How can she get both of them in her mouth?”

“Doesn’t he get, you know, shit on his dick?”

“Oh, that looks like one of the riding crops Gran uses on the farm!”

“Wow, that’s a lot of rope?”

Bob could not get her to shut up. Normally people in these stores are quiet and sullen, looking at anything but each other. But this young, newly married woman was causing the other patrons to smile, mostly at Bob’s obvious embarrassment, as he trailed her around the store and looked at everything she excitedly shoved in his face.

But then Jill found the amusingly titled “Sex Education” section. Video’s on HOW TO: do anal sex, do threesomes, do oral. They weren’t really instructional videos, just thin excuses for more porn but Jill was taking them very seriously. Bob almost laughed out loud. Jill picked up one by Nina Hartley on how to give and receive oral and started to the checkout. Bob almost died. 

Jill, however, was very serious even if she was giggling a lot. As a new bride, she took making Bob happy in bed very seriously and she knew, despite being raised on a farm, that she was awfully naive. This store had just shown her how true that was! She was startled to learn that women put penises into holes other than their vaginas. She was determined to learn how all that worked!

But it got more embarrassing for Bob. There was a display of bondage toys near the register. Jill was fascinated. She fingered everything and finally picked up a “Starter set.” Years later she would laugh at her purchase. They were pink, thin vinyl and connected with plastic “chains”. Oh, and then there was the “wall of vibrators.” Jill asked Bob what they were for?

“Um, you know, you put it on your sex, and it helps!” he stammered.

“Helps what?” she asked before thinking about it and then, finally, looking just a little embarrassed.

“You pick one!” she said to Bob as she moved away. He chose a tame, battery powered ‘lipstick’ shaped vibrator; tame but just the first of many more to come, or is it ‘cum’?

At the register there was a selection of “Stimulating Lubes!” To Bob’s final embarrassment, Jill asked the goth young lady behind the counter for her recommendation. She didn’t even look up from the Rolling Stone magazine she was reading, just reached up and handed Jill a bottle of “clit tingler.”

Bob couldn’t get out of there fast enough; he threw a couple of twenties on the counter and didn’t wait for change. Years later he can still remember the whole evening, especially when they got back to the hotel and Jill wanted to try her first blowjob while wearing the cuffs behind her back. She was surprised at how fast Bob blew his load, she felt like they had just gotten in position and started. Jill was just getting into the rhythm and starting to enjoy it, the feel of his cock filling her mouth when, boom, he was done. “Oh well,” Jill giggled to herself, “I guess I’m better at this than I knew!” Jill got even better after watching the video at home, and eventually learned to swallow, and Bob grew even deeper in love with his adventurous if naïve wife.

While Bob was reliving ancient history, Jill was sitting on the old army bed trying to figure out how to get Bob to let her cum. She really needed it bad, and she didn’t know how much longer she could behave herself. The next evening when Bob came down with dinner and to chat for a while, he reminded her about their N.Y. trip.

“I wonder whatever happened to that blowjob instructional VHS Tape?” Jill wondered.

“We probably threw it out with all the others when we realized we hadn’t owned a VHS player in years and could find all that stuff for free on xhamster.” Said Bob.

Hmmm, could this be the angle she needed to earn an orgasm?

“Hea Bob, could you find me an instructional video on doing deep throat? And let me use the laptop long enough to watch it? And do we still have that silicone model of your dick that we molded with that novelty kit I gave you a few years ago?” She asked.

“Well, this could get interesting,” thought Bob.
“I’ll see what I can find you slut!” Bob laughed.

Later that night he did find both an interesting video, the dildo and he threw in a small spray bottle of numbing spray for when someone has a sore throat. The next morning before he left for work, he set the laptop up on a TV Tray just out of Jill’s reach, didn’t plug it in so it would run out of battery in a couple of hours, and put the video he’d found on loop. He seriously doubted that Jill would ever master a deep throat, but he was going to really enjoy watching the surveillance tapes of her trying!

Jill spent most of the morning kneeling as close to the laptop as her chain would allow with the numbing spray in one hand and the dildo in the other. She did manage to get it pretty much all the way down her throat but couldn’t keep it there for even a second, and even with numbing spray she gagged and dry heaved. This was going to take a lot of practice.

Jill did an extra-long treadmill session after the laptop ran out of battery and fell into a deep nap. So deep she didn’t hear Clair coming down for her after school visit until the cheerful “So how was your day!” greeting.

“Oh shit,” thought Jill with a start, “where did I leave that dildo?”

The answer was, right in the middle of the floor along with the empty bottle of throat spray.

Clair didn’t comment on it for quite a while. Jill thought about trying to scoop it up and put it on the shelf with her toothbrush but decided to just ‘play it cool.’

Finally Clair said “Dad’s OK with you having that...” pointing to an obvious silicone penis?

“Oh, I can’t use it, at least not... “, Jill stopped not sure how to finish the sentence.

“Is that sore throat spray? Oh wait...", Clair stopped, finally putting the whole thing together.

“You know, when I was your age, I didn’t have a clue there was anything other than missionary sex, and I only knew about that because I grew up on a farm.” Jill laughed.

And as they talked, Jill told Clair all about her and Bob’s trip to New York and the video store. Well, she didn’t tell her about everything, just about their adventures in the store.

And so, Clair became used to another of her parents interesting sex habits, as she frequently interrupted her Mom’s practice sessions. Because Jill practiced a LOT. When she set her mind to something she could be very determined and stubborn. And she did make progress, but it was very slow progress. Bob, on the other hand, found watching Jill’s practice session on video to be the highlight of his day!

Another evening while Bob was letting Jill’s sexual frustration build, he put her to bed right after her dinner, cuffing her hands to the top of the metal bed frame and strapping her ankles to either side of the metal frame. He then took a belt and tightened it around her waist. He put brand new lithium AA cells in her penis vibe, set it to low and inserted it into her cunt using another long belt through her crotch to hold it in place. Wishing her a good night, he turned out the lights and left. That was a LONG and very frustrated night for Jill as the batteries didn’t run out until almost 4am (not that she had any idea what time it was!) When the morning came, Bob came down before breakfast, removed the vibrator and aggressively fucked Jill until he came. He came so fast that she had no time to reach orgasm.

And so it went all month, every few days Bob would come up with some way to edge Jill while assuring that he got off; then he would carefully review the surveillance video in the hope of catching Jill relieving herself. She never did.

But she did take out her frustrations on the treadmill and the exercise bike, not to mention doing pull-ups, push-ups, squats and every other exercise until she was totally exhausted.

And it worked!

As each Saturday’s weigh-in edged closer and closer to Jill’s release weight the tension built until one Saturday morning Clair heard an ear-piercing scream from the basement. She really wasn’t sure if she dared go downstairs or not. The scream could have been pain, or it could have been orgasmic, but as soon as she heard her Dad call her name, she knew it was good news and ran downstairs. Bob had a huge grin on his face, Jill was hugging him and happy crying, Clair joined the hug.

Bob then excused himself and went upstairs to get the key while Clare made a point of admiring Jill’s figure and muscle tone, which she had seen all along but still made a point of admiring. Bob came back downstairs with a puzzled look on his face, “Clair, did you take the keys off the keyboard, I didn’t find them?” Jill’s face fell for just a second until Bob held up the keyring and they all laughed at Jill’s momentary distress. As Bob unlocked the chain from around Jill’s waist for the first time in months and months, he suggested that Clair go run a hot bath in their large master tub and put some bubble bath in it. Jill thought that was a great idea and asked if she could also have a glass of wine, something she had perhaps missed more than any other food!

That afternoon, after her first “normal” meal Jill put on an unglamorous exercise outfit and they all headed out for a shopping expedition. Jill had kept very few things from before her weight gain so nothing in her closet fit anymore, not even the bras and panties. Bob spent thousands that afternoon on everything from new underwear to a couple of really nice party dresses. Bob was sure those dresses would make their male friends (and perhaps a few of their female friends) stare when they saw Jill’s new body showcased in them.

That night Bob had made reservations in the most highly rated restaurant in town. Jill put on one of her new, killer dresses and she and Clair did each other’s hair and makeup. Clair had to admit she was a little jealous of her Mom’s new figure and outfit, especially since Bob had told her to invite Fred. Clair was worried that Fred would spend the whole night staring at her Mom, which didn’t happen, Fred was no dummy! Although Bob reminded Jill that her stomach would not be able to handle a heavy meal until it adjusted to real food again, Jill couldn’t resist the Trout Almondine with asparagus, a salad and a slice of chocolate cake for dessert. She threw almost all of that up several hours later, but still declared the evening a total success.

Fred was a perfect gentleman, congratulating Jill on her success without ever mentioning “weight” or asking where she had been. Bob was impressed and Jill even more so. Clair had told her a lot about Fred since they had started dating but she was more than a little worried about getting questions she wasn’t sure how she would answer. Now she was starting to wonder just what Clair had already told him. But if she had told him, she was even more impressed with his discretion. Bob and Jill were also impressed with how Fred treated Clair and with what a great conversationalist he was. In short, they liked him.

For Fred’s part, he was convinced there was more to this family than Clair was willing to share right now. and he was OK with that. He was now sure that he was in love with Clair and wanted to spend his life with her. He could wait till she was sure as well and was ready to bring him into her family circle. In the meantime, he was just happy to finally meet Clair’s mother, and even happier that she was such a nice and attractive person. Fred would love Clair anyway but was aware that looking at a girl’s mother gives you a preview of what your future wife may look like in 20 or 30 years! And he liked what he saw!


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