Jamie and Kaley Learn from Dad

Everyone in this story is 18+

Jamie and Kaley met at school, she was the dance captain who had a History and English class with him. She was terrible at both subjects but Jamie was particularly gifted in those areas. He offered to help her study and she agreed.

She thought he was cute in a stoner kinda way. He always wore a band t-shirt or a Cleveland Browns hoodie to school, his hair was long, blonde, and thick, and while he was very skinny and slight he did have a cute butt. Jamie wasn't as tall as her normal guy being only 5'6" but he was taller than her own 5'2" so she didn't really mind.

When the two of them studied the first time she was taken aback at how pretty his eyes were. They were a grey color, either penetrating or soft and gentle depending on the intensity of his gaze. His lips were surprisingly full for a guy and she wanted to feel them against her own.

She didn't know that she actually liked Jamie, but she definitely thought he was cute. Finally one day after they had been studying for weeks she looked at herself in the mirror in his bathroom and thought about it.

She had been wanting to kiss him for weeks, to get it out of her system she told herself. She brushed her long black hair a bit to make it look less of a bird's nest. Took off her glasses and put in her contacts to better admire her deep emerald eyes. She thought about whether or not she should pull up her boobs or not but decided to just remove her bra. This way the cold basement would draw his eyes to her chest and she could make her move.

She knew he was too intimidated to make his own, and she found that cute. After adjusting her large F cups around in her shirt, she turned to see how her butt looked in the leggings. It was popping, as it should since she did squats and dance exercises nearly every day.

She walked back down to the basement and saw Jamie sitting there in his jeans and Grateful dead shirt. He was packing his bong as she made her way into his eyesight.

"Oh, sorry I thought I had more time. I'll put this away" He said, setting down his bong next to the couch.

"No actually, since you helped me get an A on my last English test I think we should celebrate. Let's smoke."

Jamie looked at her surprised but excited. He didn't think he had much in common with Kaley, and was beginning to think that his friends were right. He had a lot of friends that were girls, but never a girl friend. He was an 18 year old virgin after all, and had been too afraid to pursue any kind of sexual relationship. He assumed he was destined to go to college a virgin, but had begun to come to terms with that.

Kaley sat down beside him on the couch. Very closely. Jamie grabbed the bong and lit it. He filled the tube with smoke, let it marinate for a second, removed the bowl from the stem and cleared it in one hit. Then he exhaled a large cloud of smoke and passed it to Kaley.

She tried to do the same, but her inexperience with drugs made her first hit end on a coughing fit that made her large chest bounce up and down. She did not feel sexy even though she noticed Jamie staring at her tits.

He gave her a water bottle that he had just opened and she sipped it slowly. She apologized for coughing and "wasting" her hit. He laughed and reassured her that her coughing was good. Meant she hit it right for a noob.

This continued for a bit until both of them were very stoned. Jamie was used to being stoned and happily zoned out in a long bout of silence that might appear to be deep thought to the uninitiated. In reality he was wondering what his odds were of getting Kaley to take off her top. He figured low, she was just being nice and wanted to celebrate. He didn't want to read too much into it.

Kaley was not used to being this high, and the silence made her self conscious. She was worried that Jamie was just being nice when he let her smoke his weed and that the rumors of her promiscuous nature (mostly fabricated) were turning him off or intimidating him to the point of inaction. She began to silently panic.

Finally she thought of a brilliant way to break the silence and get it all out in the open. "Wanna play truth or dare?" She asked.

Jamie looked at her shocked that she had regained the ability to speak, then took a second to ponder her words and their meaning. Then their implications. And he agreed. She went first.

"Truth or dare?" Jamie asked.

"Truth" she answered.

"Ummm, did you really have a thing with Mr. Olinger the economics teacher?" This was one of the more salacious rumors about Kaley (and a few other girls) that had been spread around the school. Mr. Olinger was a former Big Ten football player and barely 27. He is tall, muscular, and according to the girls of the school, very handsome. Jamie felt like an idiot immediately after asking the question. He couldn't believe he had ruined his chances in less than 10 seconds. 'Fuck you moron' he thought to himself as he waited for her answer.

"No... that's not true, he was coaching the football team in his grey sweats and I commented on his bulge to Becky, that was it. Everyone decided that I thought he was hot. Which he is, but then that turned into me fucking him. Which I didn't"

Jamie nodded, taking it all in and deciding that made sense. Then she asked him Truth or dare and he also said truth. He didn't want to seem too eager to get dirty after all.

"Are you a virgin?" She asked.

Jamie was embarrassed and couldn't bring himself to say the word yes. So he nodded.

"Aww. Don't be embarrassed, it's cute. It's a good thing." She tried to reassure him. But he immediately went to asking her truth or dare to stop the conversation. She said truth again.

"Do you think size matters?" He asked. Jamie had always been nervous about size. He knew he was smaller than average, he'd never measured for fear of the shame, but he knew it didn't fill out a toilet paper roll. And that was apparently the barometer for a small dick. He also knew that when he was soft his manhood turtled inside him. For some reason though, asking the question was starting to make him hard.

"Umm. Yeah I mean a little, but it's not the end all be all ya know?"

"Yeah I was just curious what a girl's perspective was" he said casually with a confidence he didn't have.

"Your turn truth or dare"

Jamie wanted to do truth but was afraid she'd ask how big his dick was. And he didn't want to lie and say big, but he also didn't want to be truthful in case she was just being nice earlier to protect him. So he said dare.

"I dare you to kiss me"

Jamie was stunned. He wanted to kiss her. He wanted it bad. But he wasn't sure this would end well. What if he went for mouth and she meant on the cheek? No... that's dumb of course on the mouth. And so he did. Then they embraced. The two locked lips and rolled tongues. Jamie HAD kissed a girl, but this was still pretty new to him, and he wasn't sure if he was good or not but Kaley assuaged his concerns when they broke lips by saying how soft and nice his lips were. Then going in for another.

Before Jamie could ask Kaley asked him again "truth or dare?"

"Ummm... truth? I guess"

"Can I take off your pants?"

Jamie said nothing, but stood up. Kaley reached for his belt and undid it. Still he did nothing. Then she unbuttoned the top and pulled them down. Jamie pulled down his boxers quickly. He was fully hard now, and realizing that he was probably going to get lucky right now, with a beautiful girl. This was a great day.

Kaley got his pants off, saw him pull down his boxers and then was stared in the face by a very small, very thin, pink dick. She had seen smaller she thought, but she couldn't remember when. Still the weed had made her horny and she thought he was cute and sweet. So this wouldn't deter her. She gave the head of his cut little cock a kiss and then enveloped it in her mouth.

It didn't reach past her tongue, so she opened up wide and licked the base of his dick. Then she got some spit on him and took her finger and thumb and started stroking back and forth while sucking on the head very lightly. Then she pulled her mouth away and looked up at him. His eyes were closed but he was very much enjoying what she was doing.

She did a quick measure with her hand and saw that it was the length of her middle finger. She made a mental note to check that out of curiosity. It was also only as thick as her middle and index finger but she decided it didn't matter at that moment and kissed his cute little balls.

Finally Jamie opened his eyes realizing she wasn't going to finish him with her mouth and looked down at her smiling. She smiled back and enveloped him back on her mouth. This time with more of a sense of finality than before.

Kaley liked Jamie she knew that, but she wasn't quite ready to have sex with him. Maybe had he revealed something more enticing she would've changed that stance. After a few seconds of bobbing and two finger jerking Jamie burst inside her eager mouth. She was a little irritated, he didn't warn her or tap her shoulder, but she also didn't have any trouble swallowing such a small load, so she shrugged it off.

The two sat on the couch for a bit after and smoked another bong. Eventually Kaley went home and prepared for the next day. She wondered if Jamie knew he was small, or if it really mattered for sex. She'd had sex before but everyone she had been with was around average to above average. Or at least she thought they were. Maybe Jamie was average? She remembered her pseudo measurements and decided to check them and then check professor google.

Based on her memory and finger length Jamie was about 3.75 inches. Which according to Google was very small. She spent hours trying to find what the best ways were to have sex with an under endowed man, but all she found was a lot of small penis humiliation sites, and even more cuckold sites. She spent a little time on them but the small penis humiliation (or sph for short she realized) was obviously aimed at the man, and did nothing for her as a result. The cuckold porn was weird and she didn't spend much time looking into it.

She did land on a site that showed positions for smaller guys, but they weren't very helpful. She knew some wouldn't work because her butt was too big, or the height difference wasn't big enough for him to get any leverage. Missionary looked the easiest to pull off, but that was better with small but thick dicks. She did see that lifting her legs while in Missionary was helpful for thin dicks, as well as lots of exercising for her pelvic floor muscles.

She already had a great core from dancing so that seemed easy enough. Then she went to sleep thinking about how she could have an orgasm from fucking Jamie.

Jamie after Kaley left did pretty much the same thing. He measured his 3.75 inches of dick, measured his 3.5 inches of girth, tried to find out how disadvantaged he was, and how best to compensate. He didn't get past the cuckold and sph porn where he masturbated three times and fell asleep. He did manage to put an ask on a social media app he used, and when he woke up he had a litany of answers. They ranged from a few positions, to letting his girl fuck them, and anal.

That last one was interesting and had a modicum of logic to it he figured. You wouldn't want to shove something huge up there right? No, a finger or a tongue or a very small dick would be perfect. Jamie went to class with a raging hard on thinking of the possibility of anal with Kaley.

The two continued to fool around throughout all of January into February. Jamie never actually asked her to be his girlfriend. Which she realized one day when she and her friends were talking about it, but they were as good as she figured. He definitely wasn't cheating on her with anyone.

The two young lovers tried all the positions Kaley had found online but nothing really helped. She couldn't really feel Jamie even with her legs on top of his head, and her pussy was as tight as it could be. She would flex it on him which allowed her to feel it, but it wasn't enjoyable.

Then there was the problem that when it did start to feel good (usually when he rubbed her clit or had added a finger or two) he would cum. She did manage to teach him to go down on her, but he wasn't very good and wasn't super into it. Then one day on March 16th, it happened. Jamie asked her for anal.

She wasn't super into the idea, but she had to admit he made some good points. And she figured that had to be tighter, which meant she could feel him better. So she agreed.

It took some doing, since she had such a large and firm ass from dancing, but they managed for her to lay over the side of the couch. Jamie spread her cheeks, added a very healthy amount of lube and slid his dick in slowly.

Kaley definitely didn't hate this. She felt him inside her, and it felt pretty good. It was a little uncomfortable, but it didn't hurt, and after a minute it felt like he was fucking her in the back of her pussy. And she didn't hate that at all. She began to moan in pleasure, which she realized was the first time she had done that sincerely during sex. Then Jamie grabbed her hips, stiffened up... and came.

Kaley wasn't mad that he came fast, because she was used to it by now, and she figured he'd get better stamina if they did that way often. She asked to use his shower, but his downstairs one was out of order, she'd have to use the main bathroom.

"What if your mom walks in while I'm cleaning my ass?"

"Don't worry she's out of town, my dad is staying here tonight. He's not gonna walk in on you, he's in the guest room watching the Leprechaun movies."

"Fine" and she walked up and grabbed a towel on her way to the bathroom.

Kaley showered herself and dressed. When she walked out of the bathroom she saw that the door to the guest room was open. Jamie's dad was laying on the bed with his lights off. Kaley had never seen him before. Her curiosity of whether he and his son looked alike got the best of her, so she peeked in. She didn't walk in the room in case he was awake, instead she just positioned herself to see inside the room.

The TV was lighting the room. She glanced at the bed where he was laying. He was on top of the covers with his pants around his ankles. She saw his hands were on his crotch and she silently gasped. Had he seen her? Then she instinctively looked at the TV. It was porn. It was some girl, maybe in her early 20s sucking on a massive cock while another guy sat in the corner jerking off. She recognized it immediately as cuckold porn.

She hadn't been into it when she saw it, but right now it seemed kinda hot. The thought of performing with a big cock so her small dicked boyfriend could watch and pleasure himself was a hot fantasy. She thought 'like father like son I guess'.

She looked back at the bed to see Jamie's dad stroking his cock...with both hands! The apple in this instance had fallen miles from the tree. Jamie's dad had to have three times the cock of his son. The room was still dark so she couldn't be sure, but an outline of a long fat cock was pretty obvious. She backed up a bit and tried to silently make her way into the hallway.

She tiptoed down the hall toward the basement. She had been upstairs for nearly 20 minutes, which she realized when she saw the oven time. She quietly opened the door to walk down to the basement to smoke with Jamie again and then go home. She wasn't going to mention a word of what she saw to him.

As she made her way down the steps she heard a woman's voice. "Are you a baby dick?" She heard.

"Yes" she heard Jamie whisper to the woman.

"Are you incapable of satisfying a woman?" She heard as she silently took a few more steps.

"Yes" she heard Jamie whisper again.

"Then do the right thing, let her fuck a real man. Or at least buy her a dildo. Women want big fat cocks, not little pinky dicks. Repeat after me. Women don't want my little pinky dick they want big cocks and real men"

"Women don't want my little pinky dick, they want big cocks and real men" Kaley was now at the foot of the steps. She saw Jamie with his laptop open and had his pants unzipped. He was slowly rubbing his index finger against the underside of his dick as he repeated the woman from the recording.

She stood there in disbelief for a second. They had just had sex?! She thought. At first she was irritated. Then she slowly let the scene take her over. Her boyfriend was fingering his dick while his father was double fishing his own massive tool. Her boyfriend had just cum inside of her less than 30 minutes ago and was now getting himself off at his own inadequacy. She continued to watch and listen.

"Now say it again, but this time use your wife or girlfriend, or crush's name, and keep stroking your own little clitty"

"Kaley doesn't want my pinky dick, she wants a big cock and a real man" Jamie said as he sped up his own rubbing.

Kaley made her way over to Jamie silently. She came up behind the couch and got on her knees. She couldn't see the computer screen or Jamie pleasure his tiny tool, but she could see his head. She came up close to his ears and waited for the woman to speak again.

"Now before you bust your pathetic little load I want you to say that you're not a man. You are in fact a beta cuck"

Jamie was about to repeat the woman, but instead Kaley said it in his ear. "You're not a man, you're a pathetic beta cuck" and that caused Jamie to shoot his little load all over himself, and Kaley to giggle incessantly.

"Unnng" Jamie said as his orgasm went on longer than he expected. "I thought you left! You were gone for so long... I'm so sorry!"

"It's fine, I mean I knew you did that obviously I'm not an idiot. But why were you watching that kind of porn?"

"I don't know... that's just what landed on."

"Sweetie, those algorithms learn from your past searches." She grabbed his laptop to see if there was anything he had been watching that she could incorporate into their own sex lives.

"Ummm. I..." Jamie realized he had nothing to say. He was cooked. He never bothered to clear his search history. And there was some stuff that would definitely make her pray for him.

As Kaley went through the old searches she found a lot of cuckold porn, and SPH on there. A lot of POV SPH she noticed. And even POV Cuckold porn. All she could say was "wow". Followed by...

"How much do you jack off? Because we have sex almost every day?"

Jamie stared at her stone faced for a moment. He didn't want to admit that he jacked off immediately after she left. That he was thinking of these girls while they 'had sex', or that lately he had been dreaming about some of this stuff as his reality. He didn't want to scare her. Instead he said...

"I don't know. A lot I guess? You probably think I'm a freak."

"No... I don't kink shame. If this is what you're into... then let's try it." Kaley said. "Send me your favorite links... let me see what I think." She gave him a kiss on the cheek and left Jamie there still with his deflated nub of a dick out and cum all over his stomach and crotch.

Jamie did as she requested and sent her his favorite POV SPH stuff. Then she sent a text asking for some of his other favorites. There was after all a lot of cuckold related stuff on there and he hadn't sent her a single link to any of it.

Eventually Jamie relented and sent her one of the more vanilla cuckold scenes. The girl used a dildo to cheat on her boyfriend at a party while he was at the store.

While Kaley admitted the girl was hot and she wished she had that dildo from Bad Dragon as well, she didn't find any of it particularly hot. The small penis humiliation was something she could do no problem, she figured. Especially if Jamie started servicing her orally more frequently. But she didn't really understand the cuckold thing yet.