Tara & Jacob

By MiniTryst.

Sometimes, Jacob couldn’t believe his luck. He looked Tara up and down as she stripped off to get ready for bed – even just taking off her sweats, she looked terrific, mesmerizing even. What did he do in a past life to deserve this? By all accounts, she was the perfect girlfriend; committed, caring, and seriously just *incredibly* hot. In all the years they’d been together, he’d never stopped being infatuated with her – and she knew it.

He felt himself getting hard just watching her get ready, so he pulled her down onto the bed into an embrace before she could finish. Laughing, they quickly undressed each other, feeling the warmth of each other’s skin, their excitement building.

Now, Jacob knew he wasn’t exactly spectacular below the belt, but he was pretty sure that he more than made up for it by how he used it, especially with Tara. The sex with her was just different than other women. It felt like they were perfectly in tune with each other, anticipating what the other wanted before they even knew themselves.

He looked down at her as they made love, watching her react to him, getting almost as much out of seeing her enjoyment as he did from his physical pleasure. The hot joy of sex spread throughout his body as he came, and he slumped onto the bed next to Tara as he thought to himself, does life get any better than this?

A few minutes later, cuddling and recovering, he heard a small sigh come from Tara.

“Are you OK?” He said with a grin, “I think that was our best one yet!” and gave her another kiss.

Thinking nothing of it, he stretched out a bit and got more comfortable – he let his eyes close as he enjoyed the contentedness that followed and prepared to drift into an enjoyable, well-earned sleep. Unfortunately, it didn’t last long.

Tara propped herself up on her elbow, looked at him nervously, and half-whispered, “Jacob, it’s just, and I don’t want to hurt your feelings here because you know I love you, but sometimes, and not all the time, but sometimes I feel like—”

“What’s up with you, Tara? Spit it out!” he laughed.

She gave him another strange look, then shook her head and lay back down.

“Never mind, I don’t want to upset you. It’s nothing. Don’t worry about it.”

He could tell how worked up she was getting, so he opened his eyes and forced himself to wake up a bit.

“Look, Tara, it’s OK, you can tell me – what’s wrong? Are you feeling OK?”

He turned his head, saw the look on her face, and his stomach dropped, “Oh god, did I hurt you or something when we were?”

She was fidgeting and picking at her nails, her head resting on his shoulder, but at that moment, he could have sworn she was stifling a small laugh when he said that.

“Oh honey, no, it’s nothing like that. It’s just sometimes. I feel like you’re not getting me there,” she said and glanced at him.

“What?”

He stared up at the ceiling and felt like a deer in headlights. This wasn’t going to be good.

“OK, look, I have to get it out. It’s just, you know, Jacob Jr,” she said, glancing down at his slowly retreating manhood, “is a bit on the small side, isn’t he? And sometimes, I’m not able to, you know.”

After a few more seconds of silence, she continued, “I mean, it doesn’t have to be a big deal. I was just hoping we could figure out a way to make things a bit, well, better for me.”

He just kept staring up at the ceiling, his stomach churning and mind racing.

After another quick pause, “Oh look, I’ve upset you now! I’m sorry, Jacob, you know I love your little guy!”

(Was that another laugh?)

“Please don’t be mad. I mean, you just sort of know already, right? He’s just not exactly the biggest. He’s more, well, cute, I guess.”

This rambling was becoming painful for Jacob. Cute? Surely she could come up with something better than that. He groaned and closed his eyes.

“Fuck!”

“Oh god, I’m so sorry, Jacob, I’m getting this all wrong. I never could figure out how to talk about this. Please don’t hate me.”

He sighed. He knew she felt bad whenever she talked this much.

“No, look, I’m sorry. It’s not your fault, and I could never hate you.” After a brief pause, he asked, “It’s just not exactly nice to talk about. How long have you been feeling this way?”

He was trying his best not to look upset, and Tara seemed pleased he was at least talking to her now. She pulled herself a little closer, her hand resting softly on his chest, drawing circles with her finger and letting it drift down his torso, and he could feel himself getting excited again.

(What the fuck? Here’s the love of my life, telling me my penis is too small, and I start getting a hard-on?)

“I don’t know. I guess since the beginning? I’m sorry, I just really thought I’d get used to it eventually. We still have lots of fun. I just wonder sometimes if it could be even better.”

She looked down at his rapidly softening member again and asked: “I mean, how big IS it exactly?”

A few minutes later, Jacob could feel Tara’s hands on his dick again, but not in quite the way he’d hoped. He could also feel the cold plastic of a ruler Tara had grabbed from the other room. How had it come to this?

Tara was straddling him, but sadly she was wearing clothes this time. It wasn’t all bad though, she had her back to him as she sat on his chest, and the view of her ass in a skimpy thong was helping him feel a bit better, at least. Meanwhile, she leaned over his crotch, making some reasonably personal measurements.

“Hey, that tickles!”

“Aww, well, tell the little guy to keep still!” she giggled, “he’s just so cute!”

“Little guy? Not cool!” He felt a bit hurt she was making jokes so quickly, but he could feel something stirring within him. Did some part of him like it when she made fun of his dick? This was starting to get confusing.

She pushed herself up and got off the bed and asked, “So, any guesses?”

“Ah, come on, I don’t know.”

Now, this was tricky. He didn’t want to overestimate and get knocked back, but it might look even worse to go the other way? It was a minefield.

“5 inches?” he ventured. He thought it was better to low-ball it.

She cocked her head and smiled, “Oh, honey. Come on. You have to try and own it. You can only play the hand you’re dealt in this life! Your little friend clocked in at dead on four inches!”

She held the ruler up to show him a black line right against (just under, if anything) the four, labeled ‘Jacob.’

“I had to mark it, maybe he’ll grow a bit and this time next year, and we can compare! We have to hope he doesn’t get even smaller. He might disappear!”

Oh fuck. Not only was she making jokes now, but he’d tried pretty hard to never put an actual number on it, and this had just made it seem a whole lot more real. He’d always hoped that he was really about average but had never had the guts to try and prove it to himself.

“Maybe it’s because we just had sex? There’s no way that was my best performance.” he offered weakly and took the ruler from her.

“Aww, don’t worry honey, four is fine, barely below average, probably. It’s just like a fun-sized version! We can always try again later if you want. Right now, I was hoping we could discuss some options.”

“Options?” he asked, confused. It has turned out to be quite an evening already. What more did she have in store for him?

With a glint in her eye, she hopped off the bed, grabbed his little shaft with just her thumb and first finger, and (ignoring Jacob’s surprised yelp) pulled him over to the laptop to show him her plan.

*****

A few days later, they were in bed again, and Jacob was just holding on for dear life. He’d never heard anyone, let alone Tara, make noises like this before. This was different from what he was used to.

She managed to catch her breath for a second and moaned, “Wait, honey, let me get on top.”

They rolled over on the bed, and she mounted him before he knew what was happening, grabbing his arms and pushing them down. Arching her back, she closed her eyes and started to rhythmically bounce on top of him, letting out a long sensual moan.

Jacob could feel himself straining against the new ‘extender’ they’d bought for him as it pushed in and out of Tara. The plastic sheath enclosed him and enhanced him, standing tall at a good eight inches. He closed his eyes and tried to imagine feeling her warmth against his dick instead of plastic and quickly sensed himself beginning to climax.

He let out a soft moan as it rose inside him, and Tara’s eyes opened as she lowered her face down into his neck.

“Not yet, honey, please,” she whispered, “hold on another minute!”

Before pushing herself upright and continuing to ride, Jacob gritted his teeth and did what he could to stem the tide. He wasn’t sure what to make of this, Tara enjoyed herself so much more than before, and she didn’t ask him to wear it every time. He knew that if he refused, she would just grow frustrated, and really, was it so bad? He was still able to enjoy himself through this thing. Maybe it was better this way.

Tara finally let out a stifled scream and tensed before she relaxed onto him a moment later. He’d managed to hold on long enough this time, so long that he was still straining against the sheath, craving release.

He let her rest a few minutes before whispering, with a grin, “I think my, uh, little guy could still use some attention if you don’t mind.”

Jacob paused for a beat when he called himself ‘small,’ but Tara just grinned. She pushed herself off him and released his dick from the plastic extension, exclaiming, “Well done, baby! Look at the little thing, and he’s still going strong! That deserves a special treat.”

She took his shaft between two of her fingers and slowly stroked up and down.

“Do you like that, honey?”

He was too desperate even to say anything, his quiet involuntary moans doing the talking for him.

“I just wanted to say how proud I am of you. Jacob, the way you handled our talk about your shortcomings has been so impressive. I feel like this has brought us even closer together.”

She paused for an agonizing second before her hand started again and sped up before whispering in his ear, “Just because you have” She paused, choosing her following words carefully, “a Tiny. Little. Willy doesn’t mean I love you any less.”

And that was it – as soon as she finished talking he burst, and sprayed the both of them with his white-hot load, causing Tara to gasp and let out a shocked laugh.

“Oh wow – honey, you enjoyed that!”

Jacob let out a relieved sigh and relaxed back onto the bed, blowing out his cheeks and closing his eyes.

“That was amazing Tara, I’ve never felt anything like it,” he breathed.

She just sat on the end of the bed and looked down at him, her face slightly surprised, but her eyes were twinkling with possibilities, before lying down next to him for a loving embrace.

*****

A few weeks later, Jacob was sitting at home with Tara, playing on her phone and giggling non-stop.

“What is it?”

“I don’t want to say!”

“Well, something has to be making you laugh this much! Come on, show me. I’m bored.”

“It’s just something the girls texted me fine, have a look.”

She handed him the phone, expecting a video of a dog or something like that, only to see her browser open on a page full of penises? Plastic penises, sex toys, he realized. They looked pretty small, though

“Don’t worry about it. It’s silly. The girls were just messing around and sent me a link”, she said, as a notification popped up at the top of the screen:

‘I bet they’re all too big for him anyway, Tara ;).’

“What was that?” Jacob asked, trying to open the text.

They’re just chastity cages. It’s silly,” said Tara, quickly taking the phone back.

“They’re what?”

“Oh, it’s just a kinky game some people play as you lock away your boyfriend’s dick for the weekend if he’s been bad, or just to keep him on his toes, I guess. One of the girls found the page and thought I’d find it interesting.”

She giggled and blushed as she explained, and Jacob’s mind started racing. Did she want to lock his dick in a cage now?

She turned to look at him and burst out laughing. “Oh, honey, don’t worry, I’m not going to buy one! You should see the look on your face,” she said as she reached forward and pulled him close, grabbing at his crotch through his jeans. “I’d miss my little friend too much if I locked him away,” she whispered, still rubbing against him aggressively.

Jacob could feel himself getting hard when suddenly she pulled back and gave him a quizzical look.

“He is still in there, right? I think I can feel something if I try?” she asked.

He groaned as she gave another little laugh, kissed him on the cheek, and headed into the kitchen for another glass of wine.

“Do you want a beer, honey?”

He sighed and shouted back, “Yep,” before collapsing onto the sofa, trying to figure out why he had just got the most rigid erection he could ever remember having. He needed a drink.

*****

Later that night, Jacob and Tara collapsed on top of each other, both sweating and exhausted after another session with the ‘enhanced’ Jacob. As was becoming routine, Tara prized the plastic off Jacob’s still straining member and began to slowly stroke.

Tara barely seemed aware of where she was, eyes closed and breathing deeply, and Jacob wasn’t surprised. The only hint she was even awake was the rhythmic movement of her hand along his shaft. The difference in her pleasure since they’d bought the extender was noticeable.

Her eyes opened a fraction as she studied Jacob’s face – his eyes closed and head back as he came close to finishing – as she slowed almost to a standstill, a playful smile on her face and a quiet moan escaping his lips.

The next few seconds were agonizing as Tara let him hang for a moment before slowly continuing.

“I wonder if there are other things we could try that will make things this much better? All it took was a little self-awareness of your shortcomings, and our sex life has completely changed. And I can tell you’re enjoying it as much as I am, Jacob.”

Tara grabbed his balls, her thumb still hooked around his cock, and squeezed his whole petite package gently with one hand, just to make sure he was still listening. Jacob let out an involuntary moan before whispering, “I am. I am enjoying it. Please don’t stop!” writhing into the bed as she squeezed a little more firmly.

Tara giggled, released her captive audience, and continued to gently stroke.

“Well, if you’ll be a good boy for me,” she said quietly, leaning in so close he could feel her breath on his ear, “I won’t have to stop for long.”

Tara pounced. Without releasing her grip on him, she quickly swung one leg over him before he could react. Both her legs were pinning his arms as he was presented with a very intimate view of her from below, still wet from their workout minutes before. For a second, Jacob thought he thought she wanted to be sixty-nine and was about to feel her lips around his aching cock, before he felt her squeezing his balls gently again. He faintly gasped just as she lowered herself fully onto his face, cutting short any thoughts he had on the matter.

Jacob had never been incredibly diligent about pleasuring Tara orally before – why would he be? As far as he knew, their sex life had been amazing, but he was smart enough to get the hint now and put his tongue to work, burying his face even further, with the weight of her pressing down on him.

While Jacob’s tongue strained to please his girlfriend, her warmth from above and the solid feel of her thighs around him would have been strangely comforting were it not for the rest of his body exposed to her fully, splayed out across the bed and pinned down by her careful positioning. He felt intensely vulnerable and knew something had shifted in their relationship, but the gentle, loving squeeze from her hand, still wrapped around his rock-hard cock was enough to keep him focused on the task at hand.

“Well done, honey, you’re getting the hang of this quickly!” she said, slightly muffled. “Now, you have five minutes to make me cum, or I won’t be finishing you off after.”

Jacob’s mind was racing – this was another change he hadn’t been ready for, toys to make their enjoyment better was one thing, but not getting to cum at all? But he realized he didn’t have time to be thinking this through – best just to make sure she finishes, and soon.

He redoubled his efforts, it felt like time slowed down as he fought through the ache in his jaw, but it seemed it was working. Above him, he could feel Tara shifting her hips as he did his best to vary the speed and pressure, as she reacted to it, and slowly he could feel her tensing up, and she approached orgasm.

He thought he must nearly be at the time limit now. Tara released the steady grip she’d had on his balls and arched her back, her nails digging into his chest as she scratched up his torso. Her whole body stiffened, and loud moans began to fill the room as she rode his face to completion.

Tara slumped backward a little, putting her hands on the bed and taking some of the weight off Jacob’s face, and his tongue gently slowed down before stopping as she maneuvered herself, so she was lying down next to him again. He could practically feel the glow coming off her as she settled herself into the crook of his arm, a lazy smile playing across her face while she stared up at him.

“Oh honey, you did so well. That was amazing,” said Tara and began massaging his desperate little cock again.

Jacob’s face was aching, his tongue was tired, and he was almost ready to burst. She’d stroked him to within an inch of his life, and he no longer had any words. Jacob let his head fall back against the pillow and relaxed, losing himself in the sensation.

“It’s a shame you missed your time limit, though. I guess we’ll just have to finish this another night”.

Jacob snapped out of it pretty quickly when Tara revealed that unfortunate truth. Before he could react, she let go of his penis and snuggled up closer to him.

Jacob eased Tara away from him slightly and looked her in the eye – he could see she was enjoying this, but this was a little too far.

“What? Surely you’re not going to leave me like this!” he said, a slightly pained whine in his voice.

“I did explain to you how it would work, Jacob. I didn’t hear you complain or object! If I correctly remember, you started working away pretty quickly”.

Jacob knew that was true, but it still felt harsh.

“It’s just unfair! I’ve done everything you’ve asked to help make our sex life better, and now it feels like I’m being punished for it.”

Until now, the expression on Tara’s face had been pure joy and mischief, but for a second, Jacob thought he saw that drop and a slightly steely look came over her before her smile reappeared, a little colder now.

“Well, you are being punished. Jacob, how often do you think I give you a blowjob?” asked Tara, “And how often do you return the favor?” Seeing Jacob pause, her smile widened, and she continued, “Exactly. I’ve been quite passive in our sex life for a while now, and it’s been fine. We’ve already talked about your small dick and how it’s not enough for me, but there are other things we should be doing as well.”

Jacob began to feel a bit funny. She was being much colder now, almost clinical, he thought, but he didn’t interrupt – she had been right. He wasn’t exactly generous with oral sex usually.

“I think it’s time we agreed on something. I should be the one in charge of our sex life. You essentially had this power before, and we can both agree it’s improved since I took charge a little bit,” Tara continued, no longer looking relaxed and satisfied but determined.

Jacob wasn’t sure about this, she was making sense, but it felt too sudden and strange. It hadn’t been that bad, had it?

As if she’d read his mind, Tara began to reassure him. She said, “Look, it doesn’t have to be anything scary. The extender we bought you was a great start, and I’m so happy about how open-minded you’ve been. To start with, I just want to work more on your oral skills. You enjoyed doing it today, didn’t you?”

Jacob had enjoyed it. As he thought back on it, he could feel himself getting excited – his little flagpole had softened while they were talking slightly but began to swell again now. Seeing this as encouragement, Tara slowly wrapped her hand around it again.

“Maybe there would be a few ‘punishments’ here and there, just to keep you motivated. If you could wait until morning before you cum, won’t it feel even better?”

Tara began to slowly run her hand up and down his cock again.

“What do you say, Jacob? Can you accept me being in charge? I promise there will be rewards as well,” she whispered in his ear.

Jacob was pretty much at breaking point. He loved Tara, and he really, REALLY wanted just to agree, but this whole thing had his mind racing. Punishments? For what? What had he done wrong? But as much as it scared him, it excited him as well. And they could just try it out for a while, couldn’t they?

Tara could see the turmoil on his face and pushed harder, “Please, Jacob, for me, just say that you’re mine and that I AM in charge. I promise this is going to be amazing for both of us.”

She let go of him and instead moved lower and wrapped her lips around his cock, head bobbing and tongue swirling around his bite-sized tiny dick.

“OK, yes! Yes! You’re in charge! I’m yours, and you can do what you want with me!” cried Jacob. He could feel the crescendo coming, and he knew he meant it – he would give Tara whatever she wanted, whatever she needed.

And then it stopped. Moments from cumming, Tara pulled her lips away, scooted forward, and straddled his chest, grabbing his hands and pushing them down above his head, his tiny dick left bobbing against a tongue that was no longer there.

“Oh Jacob, I’m proud of you! This is going to be amazing,” she said as she kissed him forcefully.

It was already too late, the orgasm eluded him, but the hot streams of cum began to pour out of him, shooting partially up Tara’s back and partially all over himself.

He let out a pained cry as she pushed harder against his arms, keeping him in place as he squirmed while she looked around in shock.

It wasn’t like anything Jacob had felt before, he kept expecting the wave of pleasure to arrive, but it just felt empty and frustrating.

“Oh Jacob, did we just have your first ruined orgasm?”

First?

“I didn’t expect that. I just wanted to leave you on the edge honey, I must be better at this than I thought!” she said happily. “Well, I said you weren’t allowed to cum tonight, and you managed it anyway. I guess we’ll need to find a new punishment for you in the morning!”

Jacob was in a daze as they both got cleaned up and ready for bed. Tara was still chatting away as they settled in for the night but seemed to realize he was quieter than usual.

“Jacob, look, it’s going to be OK. I love you. Nothing has changed there. This is going to be fun, I promise. The punishments will just be a bit of fun as long as you play along, and if you give it your all, the rewards are going to more than make up for it.” whispered Tara, the lights already off, the words just appearing out of the dark.

Jacob nodded and could tell Tara had felt it. She reached down, grabbed his crotch through his underwear, and gave it a quick squeeze while kissing him good night.

“I’ll see you and your little friend in the morning,” she finished before rolling over to get comfortable.

Jacob lay there, hands behind his head, eyes wide open in the dark, staring at the ceiling he couldn’t see. What had he agreed to here? He loved her, though, and knew she meant well. He just hoped it didn’t get out of hand.

 

The End.

 

*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.

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