College Bound Pt 03

While James and Jenny were eating breakfast, she checked her phone for messages and found more than a dozen from Tiffany obsessing over James. Her 'hookup' date turned out to be fairly lame, she wrote, with the young man nutting only minutes into their encounter.

When she finished all of them, she filled James in and added, "I was thinking...we need to go to Boston at some point soon and perhaps this weekend would be best. We could rent a car, spend the day and maybe invite Tiffany along too so you can tease the shit out of her."

"I'm game, Aunt Jenny. It will be fun. I'll need to find the right vehicle so you can blow me while I drive."

She laughed and said, "Not outside this apartment, I won't."

"We'll see. I was thinking we should visit a sex shop. I've never been in one and it should be fun. I've heard you can get a vibrator that can be worn under the clothes and has a remote control. I'd like to buy one for you so that when we're out and I'm feeling horny for you, I can click it on and make you suffer with me."

"Hahaha! You're too funny!"

Shortly before lunchtime, the two of walked out of his first sex shop and she was already wearing his gift. She was still trying to puzzle out how she let him talk her into this.

They found a nice place for lunch, and he brought up the rental car subject again. When she refused to give in, he turned the vibrator to the lowest setting and smiled as she temporarily went rigid.

The waiter arrived and he left it on while she stammered out her lunch order.

Once they were alone again, she said, "Look, it's not that I don't want to do it. I do! It sounds hot, but I'm trying to keep us safe."

"Perhaps you're being overly cautious."

James was fingering the remote as he spoke and popped it up to level two.

Again, she went rigid and grunted softly as she squeezed his hand.

Trying to whisper, she hissed, "James, I'm going to cum if you don't turn it off."

"Hmmm. I wonder what that would look like! Maybe you'd prefer it on level three."

"Oh, god, please don't! I surrender. Fine! I'll suck on you in the car, there and back. I'm begging you to turn it off."

James chuckled confidently as he switched it off. Admiring the remote, he said, "This has to be the best purchase I've ever made!"

When she tried to wrestle it away from him, he stuck it in his pocket and threatened to turn it back on if she didn't behave. This quieted her up quickly and she sat there, knowing she'd been put back in her box for now.

Jenny sat there dumbfounded, trying to absorb everything. A part of her should be furious for what he was doing but a much larger part was highly aroused by the control he held. With a mere touch of a button, he could quietly ignite her innermost passion and use it against her. And the thought it would almost always happen without warning brought a whole new level of eroticism to their game.

Feeling the residual heat in her groin, she whispered in his ear, "I want to suck you dry right now!"

Whispering in her ear, he replied, "Good girl! Maybe an opportunity will come along while we're out."

What was wrong with her, she kept asking herself. He was misbehaving. Abusing his hold on her and making her reconsider boundaries they already agreed on. And now she wanted to reward him by licking his cock? How could that logic possibly make sense? It didn't, she knew, but she still wanted to do it.

After lunch, they were browsing in a nice department store when he found an area in men's clothing with a dressing room area that was practically deserted. Clicking the remote to level one, she froze momentarily, then looked around. It was obvious to her he turned it on because he was activating his blowjob doll. Seeing the dressing room, she knew exactly what to do.

She followed him in, and they went into a small room with a bench. She didn't hesitate to get on her knees, and he didn't hesitate to part her lips with his thick member. As he grew closer, he switched the remote to level two and tried to time his release with hers.

She gave off noticeable signals and he actually found it easy to get off with her. She, however, found it extremely challenging to capture all his fuckjuice, without spilling, while in the middle of a good orgasm.

When he finished, he turned off the vibrator and kissed her on the forehead as he complimented her for being a 'good girl.' Zipping himself up, he left her alone to compose herself. She sat for a moment considering what just happened. He used her like a dirty whore, yet she fucking loved it! And hearing him tenderly call her a 'good girl' actually made her feel like a good girl. Coming full circle, she reasoned good girls were supposed to suck cock, therefore, there really wasn't a problem.

Walking out of the dressing room, she felt much better having sorted through her reservations. She might start wearing that little vibrator in public all summer long! It gave her more chances to be a good girl and that alone almost made it worthwhile.

The day went beautifully after that and they had a marvelous time at the next stop, before finally grabbing some take out on the way home. The evening was as fun as the last three had been and the days ticked by as Aunt Jenny became more his sweet slut with each new day.

The weekend came and they had plans to go to the Six Flags Amusement Park together. Jenny confessed to James that she now adored wearing her new vibrator with him in public, but she suggested it stay home on this trip since she couldn't risk Tiffany figuring things out. He quickly agreed and it took a huge load off her mind knowing he wasn't going to take foolish risks.

He still insisted on renting a pickup for the trip to Boston since the center console flipped up and she now liked the idea, finally comfortable with the idea of blowing him during the drive.

Taking overnight bags, the plan was to spend the night at Tiifany's apartment before exploring some of Boston on day two prior to heading back. Tiffany had only the one bedroom plus a sofa sleeper so Jenny would share Tiffany's bed while James took the couch.

Jenny mentioned that in all likelihood though, Tiffany would be dragging him into her bed that night, forcing her to sleep on the couch but she said it was well worth it since he'd be getting valuable experience with someone new.

The drive out was amazing for him, but her view was limited with her face in his lap most of the time. When they arrived at Tiffany's, they went up to her apartment briefly so Jenny could use the little girl's room.

James took a long, hard look at Tiffany and liked what he saw. She was quite small at around five foot, two inches in height and very petite with a weight no more than a hundred pounds. She had a small, pretty, oval shaped face with bright blue eyes and sexy, curvy lips.

She was wearing a short, beige miniskirt with a snug fitting top that really showed off her large, probably enhanced, breasts. Her legs were tan and nicely sculpted and she had her hair up in high pigtails which gave her a youthful, 'wild child' kind of look. While walking shoes might have been more comfortable at a theme park, he was digging the matching, ankle high, lace boots.

Being summer, he chose to stay comfortable in cargo shorts but at Jenny's suggestion, he ditched the underwear so Tiffany could get a better look at his erections throughout the day.

Alone with Tiffany for a few minutes, she started in right away. "So how do I look?" She made sure to spin around and jut her small, round ass out in his direction for added effect.

Mentally prepared to battle with the sexy lady, he looked her up and down, as obvious as he could be about it, and said, "Mmmm. You look cute as a kitten! Some young, cougar tamer is going to be a lucky man! How did your date go, by the way? Satisfying, I hope."

"Not quite as satisfying as I would have liked but there's lots of fresh game out there. I always keep an eye out for new targets to hunt."

Hearing her talk about hunting young men was driving him wild and it took little to stir his rod which had been comfortably hanging down his right leg. With it starting to swell, it had no place to go and created what looked like a log in his shorts. He could see that Tiffany spotted this right away as she began chewing her lower lip which he now saw as a tell for when she was turned on.

Jenny came out before they could get too deep into their playful banter, and they headed out. Although the truck had rear seating, Tiffany hoped up front, in the middle, claiming she wanted to hear the conversation better. He certainly didn't mind since he found the electricity of being next to her, combined with her perfume, to be intoxicating.

Having no arm rests in the middle, she casually rested her left hand on his right leg. A few miles, later, her fingers were on the head of his swollen rod and for more than fifteen minutes, she drummed them maddeningly with an occasional light rub. He throbbed constantly throughout the drive and it would have been impossible for her to not notice this, but they were beyond that now. This was her in attack mode.

While he absolutely loved Tiffany's attention, James had to wonder if this was how he'd been making his Aunt Jenny feel with the vibrator. Helpless to his whims and teasing. If so, she obviously loved it. She wore it on day two without being told and on day three, he deliberately forgot the remote but, in the cab, she told him she had it and slipped it into his pocket.

By the time they parked, James already payback in mind. They spent hours going on different rides and having fun when he finally spotted the perfect ride.

It was a childish, water log ride where the riders sat in a line, with each person sitting between the legs of the person behind them. The person at the back had a backrest but all riders forward had handrails for support. Because it was designed for younger riders, there were no bars or other restraints and all children rides were designed large enough for parents to ride with their kids. It was perfect, he thought.

He jokingly suggested the ride and Jenny quickly agreed, giving him a sly wink. Her dirty mind must have quickly deduced what he had in mind! He was more surprised when Tiffany excitedly agreed. When it was there turn, he jumped to the back and beckoned Tiffany to sit in front of him.

Before they even took off, Tiffany scooted back and wiggled her ass into him, then leaned back into his chest, pinning him to the backrest.

Tilting her head back, she said, "This is comfortable. I'm glad you picked this ride!"

The ride started to glide forward, into a darkened tunnel and he slid his left hand around her flat belly to hold her into him while his right hand ran up her thigh, under her short dress and found her wet folds. She immediately jumped but made no move to stop him.

Whispering in her ear, he said, "Kitten, let's see how comfortable you are by the end of the ride!"

She leaned her head back and whimpered and he knew then she'd be sucking his dick soon after the ride ended.

"Kitten, I see you aren't wearing panties. Very naughty of you!"

Before she could respond, he found her button and teased it by swirling a fingertip around it, causing her to stiffen up.

Dipping a finger inside her, she whimpered again and he laughed. "It's not like you to be so quiet, Kitten. Are you distracted by something? I can stop."

As he withdrew his finger, she pleaded, "No! Please don't stop!"

Resuming his exploration of her folds and creases, he confidently replied, "Because you asked me nice, I'll continue."

By the end of the ride, she was begging to be put out of her misery. "We can go on the ride again, Kitten, but you'll need to get Aunt Jenny's permission. And I want you to tell her why. In detail. Understand, Kitten?"

Tiffany leaned forward, pulled Jenny back and talked softly in her ear. Suddenly, Jenny laughed but it was obvious she was happy to do another go around on the cheesy ride.

When they pulled into the unloading point, there were practically no riders in line, a testament to just how uninteresting the ride was to youngsters. Jenny asked the employee if they could go again, offering to get out and go through the line, if need be, but they were given permission to stay in place. As soon as they entered the tunnel at the starting point, James resumed his merciless teasing of her swollen, drenched cunt.

Halfway into the ride, she whined, "You promised to take me over! You can't leave me like this!"

Firmly, he responded, "Kitten, I only promised to touch you. Not to grant you an orgasm. If you want that, you must earn it. And if I'm impressed by your efforts, I'll spend hours fucking your brains out later tonight. Or I can sleep on the couch like we originally planned."

Reaching her arm behind her, she found his hard dick and gave it a squeeze before saying, "I want to impress you! You'll see!" Not more than ten minutes later, she was on her knees, looking up and desperately trying to please him with her warm mouth.

Her relatively small mouth made his prick look even larger and as she struggled to work on the first few inches, he dwelled on her reaction when he unzipped himself and presented his meat to her only minutes earlier; Her eyes went wide and she whispered to herself, 'Oh my gawd!' as plunged her mouth over it.

Stroking her hair, he moaned, "Mmmm. What a good girl you are, Kitten! I'm going to enjoy this!"

Feeling his gentle hand and his warm praise put her in an extra special state of mind. She loved giving head but she rarely let a guy cum in her mouth. She just never got used to the taste but much more importantly than that, guys had to earn that privilege and most simply didn't measure up. She was a slut with high standards.

She decided long ago that before she'd ever swallow a man's juice, he had to show her an amazing time. Expensive meals followed by expensive concerts and if the guy did all that and also made her feel like a queen, she MIGHT allow him that luxury.

But now, as she feverishly sucked his big knob, she found herself revisiting that policy. Or at least making an exception in this case. She wanted to please him so badly and naturally, that meant swallowing. Setting her mind to it, she was determined to suck him dry and earn his gratitude.

Studying her face, seeing her desire only to please, he had her exactly where he wanted!

Cupping her small face, she closed her eyes as he spoke. "Oh, I knew you were a sweet, gentle Kitten! You're doing such a great job, Kitten! I'm loving every tongue stroke."

Using his thumb to caress her cheek, he asked, "You going to be a good girl and take my milk? Loving kittens like you, need lots of sweet milk!"

Looking up at him again, she nodded. She didn't just need his milk, she thought. She fucking craved it! She'd swallowed plenty of times but never because she wanted to and certainly not because she enjoyed it but today was going to be a first for her. She was going to whorishly vacuum his big nuts dry and she was going to cherish his flavor as she looked up and watched him go cross eyed!

James knew that Tiffany's skills at sucking cock were nowhere near his Aunt Jenny's talents, but he absolutely loved the control he had over this situation. He had her tightly wrapped around his finger and looking down at her, he considered that she might be enjoying blowing him more than he enjoyed receiving it!

James was ready to let her have her sticky reward, but he reminded himself not to squeal out with joy like he would have done days earlier. A confident man enjoys the blow without her knowing the full extent of his satisfaction.

Willing himself over the ledge, he continued to gently stroke her cheek as he smiled and calmly said, "I'm going to let you have my milk now, Kitten. Here you go! OH! Oh, Kitten! Very nice, Kitten! Oh, yeah, you're such a good girl! Such a loving Kitten! Mmmm. Be sure to get it all!"

James had to put on his poker face as he exploded in the hot blonde's warm mouth. She was slurping him good without stopping. As she continued, they both knew how sensitive he was getting but he couldn't let her think she had the upper hand.

A few moments later, she accepted that he was strong enough to take it. In an act of tender submission, she opened her mouth and displayed everything he'd given her. Swallowing it all down, they both knew who would be in charge later tonight.

Pulling her up, he kissed her deeply and said, "You've pleased me greatly, Kitten. Tonight, I'm going to fuck you senseless with my big cock. I want you thinking about that all day."

Tiffany smiled and nodded. How could she possibly think of anything else?

Zipping himself up, he thanked his luck that no one had come into the unlocked storage room they found. Jenny had been keeping watch outside but that wouldn't work for long. While he longed to plunge his dick into the tiny blonde, he knew it was better to leave her unfinished. Letting her marinate all day would have her delirious with need by tonight.

As they stepped out, Jenny laughed and said, "You both owe me big time for this!"

James hugged her warmly, pecked her on the cheek and said, "Thanks, Aunt Jenny! You're the best aunt ever!"

Tiffany jokingly joined suit, hugging her and repeating his words.

Saying it just loud enough for Jenny to hear, he asked Tiffany, "Should we let Aunt Jenny watch us later?"

Meaning it only as a joke, she surprised him by feeding into it excitedly. "That would be sooo hot! She could use my phone to video us!"

The three of them got a good laugh out of it but Jenny found herself dwelling on it the remainder of the day. She knew she'd kill to watch her stud nephew turn the little slut inside out. He was certainly acquiring the skills to do it. And while she couldn't do anything sexual with her nephew, she knew that Tiffany would never leave her hungry.

When Tiffany ran off to use the restroom, James took the chance to catch up with Jenny in private.

"Aunt Jenny, it's a good thing we left your vibrator at home because I would have switched it on several times today."

"Would you believe I've been missing it all day. I've grown to love the control you hold over me with that wicked thing!"

"Aunt Jenny, are you weirded out by any of this? It had to feel strange guarding that door while your best friend gave me a blow job."

"Are you serious? You two have me horny as hell! I overheard the way you spoke to her when she blew you. That was so fucking hot! She never swallows a guy unless there's big gain in it for her so you must really have her spinning!"

"How's this going to be tonight? I feel bad that you'll be alone, fingering yourself on the couch. I promise to make it up to you big time!"

"Fuck, I actually do wish I could watch tonight! That would be amazing. And Tiffany would eat me out. She'd never let me go empty handed like that. But showing interest in watching my nephew is flirting with disaster."

"What if we had some drinks beforehand? We could pretend to be more shitfaced than we really are and that would be the excuse for being wild and impulsive. We still couldn't do anything between us, but we could be together. And Tiffany would fill your need. I noticed her bed is huge so we could probably all sleep together and everything gets blamed on the alcohol."

"Hmmm. It could work but you and I would need to be extra cautious. You slip and call me, 'Mommy' and that will be tough to explain away. Let me think on it."

Tiffany appeared a minute later, and James ran off to the restroom next hoping to coax secret conversation between the two ladies.

By the time they got something to eat and finally made it back to Tiffany's apartment, he knew something had changed. Both Tiffany and Jenny were now keen on having drinks so James played along, pretending to drink more than he was and when Tiffany wasn't looking, both he had Jenny would either dump some of theirs in the sink or into Tiffany's glass. Very soon, Tiffany was mildly drunk and unable to notice too much.