Read Part 1 Here
Read Part 2 Here
Read Part 3 Here
Read Part 4 Here

*****

Part 5…

“Ok, let’s take another quick shower, and then we’ll go to bed,” Chloe decided.

Once in bed, she immediately swung herself on top of Greg, but unlike he expected, she sat on his chest. Her bare pussy was just a few inches in front of his eyes. She looked down at him.

“That was a great night. Did you have fun too? What do you think of Jade?” asked Chloe. She reached back to find his small member and began to jerk it with her right hand.

“She seems nice. No wonder she’s your best friend.”

“And do you think she’s hot?” Chloe slightly increased the speed of her hand and looked deep into his eyes.

“Mhmm, she looks okay, but not as hot as you,” Greg knew he was on thin ice. In front of his eyes, Chloe’s pussy gleamed at him, was she getting wet again?

“Did you check her out,” Chloe continued questioning as she kept jerking him off.

“I… well, no, well, maybe I looked at her briefly when I was looking for you.” Greg didn’t like where this was going, but he could smell her pussy now, too. Chloe was getting aroused again.

“Don’t you like the secretary style? I thought all men thought it was hot,” Chloe sensed Greg’s arousal in her hand.

Greg didn’t want to be a weird guy. “Sure, secretary style is hot, especially with the glasses.” He looked up. Chloe’s nipples were hard and protruding from her shapely breasts. Above them, he saw the fine Asian features of her beautiful face but now looking sternly down at him.

“Ah, so you noticed her glasses right away too, seems you did look a little longer then, didn’t you?” Chloe loved to hold him in this state of growing arousal. He was pudding in her hands.

“No, well, I didn’t notice the glasses until later, after we were sitting together at the table,” Greg tried to break free of the verbal grip. His breathing was already quickening.

“Ah, I see. Then what were you looking at for so long before? Jade told me you were looking over for quite a bit. Maybe her legs in that short skirt or her tight white blouse caught your attention?” Chloe slowed the pace of her right hand but gripped it more tightly and moved her pussy forward. Greg groaned.

“No, I didn’t. Believe me. I couldn’t see the skirt…under the table…after all, I’m not into…big boobs at all.” Greg could have slapped himself.

“Oh, so you checked out her tits!! Greg, Greg, Greg, such a naughty boy you are. I don’t think I will give you a handjob tonight.” Chloe took her hand off his penis.

“Instead, you are going to lick me again!”

Chloe moved forward enough for Greg to reach her sweet honey pot with his tongue. Her pussy juice was already dripping onto his chest and running down his neck. Chloe could have several orgasms a night, 5, 6, 7, or 15. She just needed the right guy, and Greg had to be that guy now and his tongue under the given circumstances.

Chloe slid further forward. Greg didn’t need any commands. He knew what to do. And he felt guilty for checking out Jade. Eagerly he licked and sucked her pussy. From his position, he could also insert his tongue into her. Chloe moved her pelvis in circular motions, smearing her already flowing pussy juice over his face again. She always needed a lot of friction on her clit, so she pressed more and more against his mouth and face. Her breathing quickened, and the room was filled with her moans.

“Yeah, that’s it, that’s my good boy. Lick me, lick me good.” She was practically sitting on his face now.

“Oh yeah, there we go, hmmmm, so good. Keep doing that. Suck it! You just love to drink my pussy juice, isn’t that right?”

“Mmm yeah,” Greg had his mouth full, his voice only coming through in a muffled way. But his affirmation was clear.

“You love my pussy and everything it provides you, isn’t that right?”

“Mmm yeah.”

“You know, if that’s so, I would love for you to drink my piss,” Chloe ground hard on his face, she didn’t need an answer, and she had no urge to pee right now. She just wanted to plant this idea in his head. She panted, riding his face in thrust after thrust, her clit on fire, juices flowing out of her pussy, into his mouth, and over his face. She arched her back, sat upright, squeezing her breasts together, pinching her nipples, and with a loud moan, she climaxed for the second time tonight.

“Fuuuuck.” Chloe fell back and tried to regain her breath, her swollen juicy, still vibrant pussy inches from Greg’s face.

After a few minutes, Chloe regained enough strength to get up from her position. Exhausted, she was now lying down on Greg’s right side. She turned towards him, propped herself up on her left elbow, and gave him a loving kiss. “That was amazing.”

“I am sorry that I checked out Jade. I couldn’t help it.” Chloe looked at him. He was so sweet and now desperate to make up and get a chance to cum tonight.

Chloe laughed out loud. “Ha-ha, don’t worry, I’m just kidding. Jade is attractive. No problem that you checked her out. I’m not the jealous type. Relax.”

“But I’m too tired to fuck you tonight. You’ll have to make do with a handjob. Is that okay?” Chloe already knew this was okay with him, and her right hand found his penis. She grabbed it with her fist and started to jerk it slowly. She could already feel a few drops of precum. His licking her love tunnel had probably excited him quite a bit himself.

She jerked him for several minutes and eventually increased the speed, but it didn’t seem to work. His penis was getting hard and soft again. Chloe’s hand and arm began to tire.

“What’s the matter? Am I not doing it right? Show me how you jerk yourself off. I want to see that.”

Greg was reluctant to perform this intimate show of his masturbatory habits in front of his girlfriend. Still, eventually, his arousal got better, and he grabbed his penis and began to jerk himself off.

“Ohhhh, really!? You’re only using your thumb and three fingers. No wonder!” exclaimed Chloe.

Greg hadn’t realized that at all, but yeah, sure. He doesn’t use his whole fist, just a few fingers. Isn’t that what all men did?

“Let me do it, let me do it,” Chloe thought this was hilarious. And she grabbed the little one with her thumb and three fingers. “Oh yeah, that’s a lot less tiring than moving your whole hand all the time.” She began to find a slow rhythm again.

“You know, I’m a total beginner with small penises. My ex-boyfriends all had at least 6 inches, some even 8. I told you about them last time. I always had to use my whole hand jerking them, sometimes both hands” Chloe loved to rub salt in the wound. She could feel his penis pulsing under her touch. He was getting even harder with this talk.

“And I had to jerk their cocks fast. With your penis, maybe jerking slowly will do it, too. Look how hard it is, wow.”

Greg didn’t have to look; he could feel he was rock-hard. Her fingers, but most of all the embarrassment, excited him immensely.

“This is very pleasurable. And not so tiring for me.” Chloe increased her speed just slightly and kissed his right nipple.

“Maybe we won’t have to have sex so much in the future at all. You satisfy me orally a few times, as often as I need it, and I’ll give you a little hand job. What do you say?”

“Yeah, sounds…sounds great,” Greg just didn’t want her to stop now.

“Look at my eyes” Chloe knew he was already embarrassed and wanted to increase this feeling.

Greg loved her almond eyes, that mix of innocence and mystery, sweetness and wickedness.

“But when we have sex again from time to time, it’s always safety first, right?”

“Yes, of course, we use contraception, of course,” Greg didn’t know what she was getting at.

“Mmm, wow, I can use my thumb and two fingers. Look,” Chloe wanted to bring his focus back to his penis.

Greg lifted his head slightly and saw Chloe’s fingers just below his penis head, jerking him off with the smallest movements. It felt great. His white, pink skin markedly contrasted with Chloe’s golden complexion.

“Nice, your little one is already oozing precum, even though I slowly jerk it. Maybe a small teenage pee-pee doesn’t need that much to cum? That’s so cute.”

Greg was utterly embarrassed. It was the first time she had called his penis a “pee-pee.” And sure enough, even though she was only stroking him very lightly, the precum was oozing out of his little hard-on. Greg was thinking of protesting, but Chloe knew to let the “pee-pee” sink in and cut him off quickly to prevent any chance to complain.

“Look at me.” Chloe ensured Greg was back in that state of shame and arousal she loved.

“You know, I realized something. The industry always creates these generic products without respecting people’s individual needs. Take me, for example. There are so many beautiful dresses for women, but many of them you can only fill with a B or a C-Cup. That’s so mean. You like my perky tits, don’t you?”

“I love them” Greg didn’t know where this was going. She did know that he loved her breasts. He shifted his gaze to look at them. They were wonderful just the way they were, small but firm and perfect for her petite body. Her nipples stood up proudly.

“And you like seeing them in tight tops or dresses too, don’t you?” She continued to jerk him off with those slow movements.

“Oh yeah, I do.” Greg could already feel his penis throbbing.

“Sometimes I have to look hard to find one that fits. Luckily, there are usually very helpful salespeople who know all the products. Sometimes you just have to ask. But I like to make that effort because I want to look perfect for you. And I know you would do the same for me.” Chloe just loved entangling him in her spider web in this state. She nudged his chin lightly, signaling him to look into her eyes again. Greg lost himself in her gaze, which was assaultive, caring, and mocking all at once. What was she planning?

“Yes, absolutely, of course, I would do the same for you,” it seemed like a freebie promise to him. He would rarely buy clothes for her, after all; if he did, he would just specify her size to a salesgirl, or Chloe would come along. The main thing at this moment was that she didn’t stop jerking him off.

Chloe beamed at him. “I knew it. You’re just such a gentleman. The thing is, last night, you told me you had a small penis. And now that you’ve said that, I also think it’s really, really small. A small, tiny, pink weenie. Maybe it’s even too much to call it a penis. Do you mind if I call it a pee-pee from now on? It just feels so much more accurate?”

Greg was in turmoil. She only realized his lack of size now because he had said it yesterday. Shit, he shouldn’t have said it. Why had he done that?

It was too late now, and his excitement drove him crazy. If she called it a pee-pee, that would be so embarrassing. On the other hand, it was just between them, and it didn’t matter; somehow, it was hot, too. And no way was he going to argue with her now.

“If you like, babe,” he said, breathing quickening. Chloe smiled triumphantly and continued to hold his gaze.

“That’s so sweet of you. Then since you have such a cute lil pee-pee, we want to make sure that we have the right dress for it, right? I realized that you got the standard size condom on your nightstand. I know it is not your fault, but we wouldn’t go with the standard industry solution when we can do much better, would we? We should honor your actual size, isn’t that right? Chloe emphasized her last words by stroking slowly in the rhythm of her words.

“Hm, I guess, but…” Greg didn’t know what to say, and his increasing arousal didn’t help.

“Don’t worry about it. I’ve got it all figured out. Tomorrow we’ll go to the sex store in the mall near my office. The people there are super helpful. Jade also asked….”

“Jade?” Greg yelled. He couldn’t believe it. What did Jade ask? Did she know all this? Did she invite them to join them in going to the sex store? A sudden rush of panic rose in him. Shame weirdly aroused him, but he wasn’t ready to be so open in front of an almost stranger like Jade. Had Chloe told her everything? Chloe felt his penis suddenly go soft.

“Relax, relax, big boy.” Chloe giggled. “Jade asked what we would do tomorrow night, so we have all day to shop before we meet up with her. Don’t worry. You’re too sensitive sometimes. Besides, she doesn’t know much. I just told her that you have a talented tongue and love to lick me. That’s a compliment. We girls all want a guy who does that. I was bragging about you.”

Greg felt great relief, his little guy slowly recovering and growing again in Chloe’s fingers.

“Can I maybe just go to the shop myself?” he tried.

“Oh, don’t be silly. We don’t have any secrets, do we? And we’re educated adults and chilled. We’ll go together. It’s not a big thing.” She grinned sweetly at him but quickly switched to a stern look in his eyes that clearly said: decision making, discussion over.

Greg gave up his resistance.

Chloe resumed her touching. She now used only her thumb and one finger in a languid rhythm.

“Look, I can jerk off your lil pee-pee with even my thumb and index finger. Sooo slow, and it’s still sooo hard. It’s so much better to jerk off a little one. It’s comfortable. I think you are about to come, babe. It is already throbbing. Damn, are you going to cum from just that?”

“Mmmm,” Greg moaned. The touch was minimal, but her talking was driving him crazy.

“Oh my God, I think your little wee-wee will shoot its sweet load if I touch it just a little longer. That’s hilarious. I never knew it took so little to make a tiny willy squirt.”

Greg jerked uncontrollably, his thigh muscles trembling slightly, his breathing growing rapidly.

Chloe giggled loudly, “Imagine if I told Jade about this. That I could make your tiny pee-pee erupt with the slightest touch of my thumb and forefinger, God, she would laugh sooo hard.”

That was it, Chloe’s giggles, her mentioning of Jade, her stimulation, and the embarrassment of Greg feeling he would come from her minimal touch. Greg felt his juices boiling, his balls contracting. His torso tensed up, his feet stretching out, his pelvis rising and arching to meet Chloe’s slightest touch. There was no way to stop it. He lost control. Several thick jets of his seed hit his belly and torso and ran down his sides. Chloe used her hand to catch it and spread it all over his torso until it was utterly sticky. Greg remained to lie there exhausted, unable to move. She snuggled up to him, rested her head on his chest and her hand on his messy torso, and kissed him.

“Let’s sleep like this. I love the smell of sperm. And that was a brilliant, sexy night with you. Tomorrow we’ll go shopping.” Chloe smiled in complete satisfaction.

*****

Chloe was the first to wake up. It was already 10 o’clock, but they were probably both so exhausted that they had slept like stones. The bed still smelled of sex, primarily due to the cum Chloe had spread on Greg’s body. Chloe played a little with the now-dried platelets on his skin.

Carefully, she pushed herself out of bed to avoid waking Greg and went into the bathroom. She was glad Greg had come to her place last night because she had all her makeup and clothes. At his apartment, she only had some sort of emergency gear. Today, however, she wanted to look hot for their adventure. “Today could be a fascinating day,” she thought. She couldn’t wait to go to the sex store with Greg. This was going to be sooo embarrassing for him and so entertaining for her. And later, they would probably meet Jade again. Jade had gotten a taste for the whole thing. All the innuendos yesterday, ha-ha. Chloe just loved her best friend. And, of course, she would send Jade some messages about how the visit to the sex store went before their meeting.

While Chloe was still a little sleepy, thinking about how to make Greg’s visit to the sex store as embarrassing as possible and brushing her teeth, she let her eyes wander around the bathroom, lost in thought. Her gaze lingered on the laundry basket for a while. Slowly, a broad smile formed on her face. “Hmmm, what if…” Chloe’s cheeky mind had already awakened. She glanced at the hamper and rummaged around in it. “I see.” She rinsed her mouth, put the toothbrush back, and slipped into the bedroom again. Greg was still asleep. She opened the closet as quietly as possible so as not to wake him.

She had cleared a small area so Greg would have somewhere to put his clothes when he slept over. “Just as I thought,” Chloe grinned triumphantly, taking Greg’s last fresh pair of underwear. Quietly, she slipped back out of the bedroom. Back in the bathroom, she stuffed his new underwear into her washer-dryer-combo and the rest of the dirty clothes, including the rest of his underpants. “Hmm, add the pre-wash programs, select eco mode, slow-dry, oh, that’s going to take 4:26 hours, no way these clothes are going to be clean and dry before we leave, that’s such a bummer, hahaha,” Chloe thought to herself. Poor Greg would probably have to go in commando today. She just needed the extra anxiety to get him to visit the sex store. Chloe winked at herself in the mirror, mouthing, “you are so good.” Then she hit the start button.

She slipped back into the bedroom and snuggled up to Greg. She kissed him, and Greg responded with a sleepy, “Good morning, babe.” Chloe’s hand stroked his sticky chest, tracing circles around his nipples and pinching them now and then. “Good morning.” She loved caressing him. His whole body belonged to her and lay before her as if he were at her mercy. Greg loved the feeling of Chloe just doing whatever she felt like. He was still half asleep, but he enjoyed her touch. She stroked her fingernails over his torso, along the sides of his body, and then over his abs. Greg had a genuinely amazing body, like an Adonis. She let her fingers slide lower, expecting to feel his little naked hard-on.

Boxer briefs! “Shit!” She’d forgotten about the briefs he’d worn last night. Greg had probably gone to the bathroom sometime during the night and, on the way back, had found the boxer briefs on the floor and put them on. “Damn it.” Chloe was pissed off. Her beautiful plan was about to evaporate into thin air. What was she supposed to do?

She almost wanted to give up. Her plan for the sex store would have to do without the added attraction. But then a thought occurred to her, and a devilish grin spread across her face. “You sneaky little subby, you’re not going to foil my plan that easily.”

Chloe reached down again and began to rub his lil wee-wee. She tenderly stroked from his balls to his head. He was already throbbing under her hand. She placed the flat of her hand all over his penis and rubbed it up and down. Again and again. She could hear Greg’s breathing getting louder and faster.

Greg turned a little toward her, lying on his right side and nuzzling his face against her breasts. Chloe was horny, too, and she loved it when he licked her breasts. Most of the time, he was quick to land his mouth between her thighs, but she also found pleasure in letting him suck her nipples. She had very sensitive nipples and leaned back a bit to give him the needed space. He took her left nipple into his mouth and started to suckle on it.

For Chloe, an incredible feeling arose that turned her on even more. On the one hand, she had this power over the arousal of his penis, but there was also something new: He was suckling on her breasts like a baby. A grown man is suckled, vulnerable, tender, and exposed. And Chloe was the one nursing him. There was something erotic about the whole situation, and Chloe felt that tingling in her pussy.

“Hmm, that’s it, baby, suckle on my titties,” she whispered into his ear as she continued to massage his penis inside his boxer briefs. She knew Greg’s fetish well enough now. She wouldn’t have to invest too much in this massage if she just pushed the right buttons in his head. She needed to get him aroused enough to play along with his secret desire to be humiliated. They had already established that he was a sub and had a small penis. Last night she had squirted boldly directly into his mouth. And he had swallowed it all willingly. He had even accepted that Chloe referred to his penis as a little pee-pee. Not only just accept, but Chloe was sure he loved her saying it. He always seemed to reach the most incredible heights of arousal when he felt the greatest embarrassment.

Chloe had very carefully extracted all these confessions from Greg, had teased and tested him until he or his penis finally willingly and needily revealed one secret little kink after another to her. In Chloe’s eyes, their relationship had reached a new level, especially after he accepted her squirting into his mouth and swallowed several loads. His little pee-pee stayed hard as lipstick in the process. She felt secure enough to proceed with less caution from now on. “Finally,” she thought. “Things will get much easier from now on.” Greg wouldn’t leave her if she humiliated him, not at all. Entirely, on the contrary, he would love her for it. And he would probably jerk off over her humiliation like a gazillion times once he was alone.

She looked at him. Greg was still suckling on her nipple.

“Yeah, suck mommy’s tits like a good boy, mmmm, you are such a cute baby. Do you like to suckle on mommy’s perky boobies?” Chloe kept massaging his stiff boy stick in his boxer briefs.

“Mm-hmm,” Greg kept sucking, nodding his head in affirmation. He felt so safe sucking her nipple and feeling her soft and warm boob on his face.

“I bet you do. Because you are such a little sweet baby boy, I am sure you would also drink the milk from my young boobs if there were any. Isn’t that right?”

“Mm-hmm.”

“I know because you like to drink everything from my body. Such a good little baby you are.” Chloe couldn’t wait to eventually amplify his obedience by having him drink her pee soon. It was the second time she had planted this thought into his head. But that was for another day. She had other plans for this morning.

“Would you like to cum while sucking mommy’s tender titties? We both know it doesn’t take much for your little baby penis to spill it. Because it is so little, yes, that’s what it is: A tiny, little, baby penis. I can feel it trying to grow big. But it cannot. It can just grow to its little, baby size. It is sooo cute.” Chloe giggled loudly.

“Your little one is so hard. I think you’re about to cum, baby boy,” Chloe whispered into his ear again. She felt his penis pulsing.

“Mmmmm,” Greg was so aroused by this humiliating talk that he too felt he was to cum soon.

With his free left hand, he reached down and grabbed his boxer briefs in an attempt to pull them down. But Chloe took his hand with a firm grip and placed it onto her other breast, her hand now missing on his little stiffy. Greg involuntarily arched his groin up in a futile attempt to find her hand.

“Uh-Uh, my baby boy needs to hold mommy’s other boob. You wouldn’t want mommy to stop touching your lil baby boner, would you?”

She didn’t expect an answer. Greg keeping his hand on her breast was answer enough. She eyed him. He looked like a baby now, eyes closed, sucking on her left breast while grabbing her right breast with his free hand. Chloe loved it and felt the moisture growing between her legs.

Greg did not want to cum in his boxer briefs. The last time that happened was when he was 16 and had a wet dream. He still vividly remembered his anxiety about his mom finding the stains. But his hand on Chloe’s tight, soft chest felt so good, and he wanted to feel her touch on his little one again.

Chloe continued her massage on his groin.

“Are you afraid to cum in your little briefs? Don’t worry about it. It’s very normal. Babies often wet their undies. Because they have no control over their little, baby penis, they lie there with their underpants wet. But that’s ok. That’s ok for a baby boy and his little baby penis.”

Greg’s breathing quickened. His face was flushed, and Chloe didn’t know if it was from arousal or shame. But what was the difference, for Greg anyway? She could sense that he was about to cum. She made sure that his little thing pointed upwards in his boxers.

“What do you think? Should I tell Jade that my boyfriend cums in his briefs? That he can’t manage to get his underpants off before he spills his load? I bet she’d laugh her ass off. Or maybe she will ask her date if that’s ever happened to him. The one with the big cock, you remember?”

It was too much for Greg. He felt his scrotum tighten. All his nerves, all his feeling were coalescing in his penis. He moaned loudly and shot his first stream. The sensation was different than usual, though. The jet met resistance and immediately felt his cum spreading around his penis head. The second and third spurts, almost as violent, pushed his cum further down and sprayed all over his groin. While Greg’s body shuddered several times, the cum ran out of his penis, soaking his boxer briefs further.

Greg’s breathing slowly became shallower again. He could feel the sticky moisture in his crotch slowly cooling off. He lay there, exhausted, with completely soaked briefs, his penis shriveling in the middle of the damp mess.

With a devilish grin, Chloe felt around his crotch. He was so soaked. She looked forward to his reaction when he discovered that all his other underwear was in the wash.

“Oh my, my little baby has wet his undies. How did this happen? Could your little baby penis not hold it?” She smirked.

Chloe pressed Greg against her. He still had her nipple in his mouth.

She kissed him on the forehead. “You are so adorable, my baby boy.”

*****

After Chloe and Greg had lain there for another 15 minutes, Chloe decided they should finally get up. After all, they had a lot of excitement waiting for them today.

“Hey baby, let’s get up. It’s almost eleven. Besides, you might want to shower and change into something drier.” With a big smile, she kissed him.

“Yeah, you are right. Good morning honey.” Greg was still sleepy, but his moist groin suddenly reminded him of what had happened briefly. He blushed, and he was glad Chloe did not deepen the topic.

Chloe went to the bathroom first. After she showered, she sat in the living room with a towel to paint her toenails. “I am done, for now. The bathroom is free. And don’t forget to shave down there. I felt some little stubbles even through your briefs when you came in them. You know I love your cutie all clean and smooth.” She loved to rub this incident in again.

“Err, sure, babe, should I just throw my underwear in your hamper? It is kinda sticky,” Greg asked from the bathroom.

“Oh, that’s very considerate of you. Please better let your undies soak in one of my hand washing basins. The hamper is empty. I don’t want to have your little accident waiting for the next wash in there for too long,” Chloe chuckled.

“Alright, no problem,” Greg added some water and detergent in the basin and let his boxer briefs soak right in.

“Oh, and could you put my panties in the hamper,” Chloe opened the bathroom door and, with a loving smile, handed her panties to Greg, closing the door again.

Greg grabbed them and immediately felt the moisture. Chloe must have been as excited as he was when she made him spill his load in his boxer briefs. Her panties were soaking wet. He put them in the hamper.

Greg stepped into the shower. The images of what had happened just last night ran like a replay of a sports broadcast in his mind’s eye, how he had knelt there and washed Chloe’s legs and feet. She had guided his tongue between her thighs and finally squirted into his open mouth, holding him in place with both hands, and how he had swallowed it all, gulp after gulp. His penis was already sticking out again, stiff and naughty. Yes, she had made it clear with her hands what she expected of him, but Greg knew that it would have been easy for him to escape from her grip. The truth is he hadn’t even attempted. And he had been as hard yesterday as he was now at the thought of it. The shaving was done quickly. He only had a few stubbles and applied some shaving cream. He got it all done in a few strokes with the razor. His little pecker was as naked again as one of a prepubescent teen. He turned on the shower.

Chloe opened the bathroom door and stepped in. “Having fun in there?” She laughed as she saw his small, bare, hard-on through the glass door. “I’ll get started on my makeup.”

Greg did his best not to think about the embarrassment waiting for him in the sex store and to get rid of his stiffy again, showing his arousal. He couldn’t stand an ice-cold shower and tried cooler water. But this did not have a lasting effect. For better or worse, he had to come out with a hard-on. He stepped out of the shower and dried himself off.

Chloe, doing her makeup in her birthday suit, peered in the mirror at his pubic area while she applied her foundation for today’s makeup.

“Wow, looks like someone is already a lil bit excited,” she giggled. “So cute!”

“You know, guys tend to be hard naturally in the mornings. It is this morning wood thing,” Greg tried to explain.

“Oh, I see. And I already thought it was because we are about to go to the sex store, and you will ask for their smallest condoms there,” Chloe winked at him through the mirror.

Greg’s tiny boner involuntarily twitched upwards, much to Chloe’s delight. “Little pee-pee’s don’t lie,” she smiled to herself.

Greg wanted to escape the awkward situation. “Ok, I’m ready then. Take your time with the makeup. I’ll go get dressed.”

“Sure,” she said, thinking, “if you can.”

It only took a minute. “Babe, do you know where my fresh underwear is? I could swear I had another one here.”

Chloe mouthed, “Oooops!?” to her reflection in the mirror as she applied her eyeliner.

“Hmm, I don’t know. Don’t you have any left in your closet? I put everything in the hamper in the washing machine this morning.”

“Shit looks like I don’t have any fresh ones here. And yesterday’s is wet now too.”

“Ah, that’s unfortunate. But don’t worry. Then we’ll just both go without underwear. I’m all about solidarity here.” Chloe, still naked, stepped out of the bathroom and grinned at Greg.

“But, huh, I don’t know,” Greg was visibly uncomfortable with the prospect of not wearing underwear during their sex store visit. His penis, however, was already fully extended again. And suddenly, Chloe felt an opportunity she wanted to grab right there.

“By the way, do you know exactly how big it is?” She pointed with her eyeliner to his groin.

Of course, Greg knew. Since he was 14, he had measured his little one countless times. And he had generously agreed with himself that under perfect conditions, it was 4 1/4 inches. But how embarrassing would it sound if he told Chloe that he knew so precisely?

“Well, I don’t know that for sure. It’s never been so important for me,” he lied.

Chloe had hoped for this answer. “That’s a shame. It might be embarrassing if we don’t know for sure afterward at the sex store. And I wouldn’t want us to be embarrassed to guess its size. It looks huge this morning, bigger than usual. Looks almost kinda menacing.” Chloe had to use all her strength not to laugh out loud. It was still the same adorable tiny baby stick greeting her from his groin. She faked a thoughtful face. “Maybe we should measure it! Maybe it has close to 6 inches, and we’d be, going to the store for nothing. ”

Greg’s brain, of course, knew that couldn’t be possible. Since he’d been measuring his penis, he’d never even come close to 5 inches, let alone 6 inches. But his pride was sparked. What if this morning was that special day when he could reach the 5-inch mark? He looked down at his penis.

Chloe could see his inner struggles. Her tall Greg looked at his tiny pecker and hoped a miracle would happen in front of his eyes. Oh god, how she loved playing with him. Would he fall for this cheap trap? Would he let her measure it? It had to be an embarrassing procedure for him, but he still seemed hesitant. Her poisoned guess that he might be bigger than they thought seemed to stroke his ego. “I mustn’t give him time to think about it any longer,” she quickly realized.

“I guess there’s only one way to find out. I’ll get a ruler.”

“What? Do you want to measure it? Now and here?” Greg felt his shame rise to his face.

“Of course. Otherwise, we can’t be sure. And don’t worry about it. I’ve already kissed, fondled, sucked, and fucked it. There are no secrets left anyway. And you would make me very happy if you let me. Pleeease!”

She looked at him with her sweetest smile, stark naked and beautiful as ever. And Greg had to admit that she was right: She knew what his little one looked like, and maybe it was bigger than he thought by some lucky chance. Chloe pouted and brought her hands together in front of her body as if in prayer, pressing against her breasts with her upper arms so that they stood full and proud towards Greg. “Pleeeeeeeease.”

Greg looked at her full breasts, sensual mouth, and pleading eyes. He just couldn’t refuse her anything. “Alright, let’s do it.”

“Ah, you are the sweetest boyfriend in the world,” Chloe blew him a kiss and beamed at him. “Let me just get the ruler.” Chloe stepped up to her desk. She had several regular rulers and quickly hid them in one of the drawers. She already knew exactly which ruler she would use. And she also knew where it was. She wanted to use the ruler her best friend Jade had given her just for this purpose but more in jest. The 6-inch Hello Kitty ruler. It was pink and decorated with hearts and bows. “It is just perfect,” Chloe kissed the ruler and returned to the bedroom.

“Are you ready?” Chloe waved at him with the ruler.

“What is that?” Greg saw the short pink ruler.

“Oh, that is the only one I could find. Jade already gave it to me last weekend,” Chloe explained with a broad smile.

Why would Jade give Chloe a Hello Kitty Ruler? Greg could now see the ruler more clearly, pink, girly with all sorts of decorative elements. Had they indeed talked about his size? Had they discussed Chloe measuring it? Greg turned a deep red.

“Ahem, why did Jade give you that ruler?” Greg inquired nervously.

“Oh, you remember that we went to the same elementary school, right? We shared the same table back then, and she accidentally stole my ruler. She recently found it at home and thought giving it back to me after such a long time was funny. It is sort of a small souvenir from our school days. You know, in Asia, we take maths seriously. So, this little ruler has always been in our tiny hands.” Chloe explained, and she just loved to talk about small things taking the opportunity.

“I see, such a nice idea of her.” Greg still thought the ruler looked somewhat new, but probably the girls just took good care of their belongings.

“And, as it is a 6-inch ruler, I feel it is perfect for us. My bold guess is that it will be long enough.” Chloe giggled and sat down on the bed. “Come here.”

Greg was still stiff and now stood right in front of Chloe. She playfully scratched the ruler’s edge along his penis and grinned at Greg from below.

Greg tried desperately to pump as much blood as he could into his little stick to make it as big as possible. From above, he could see his tiny member was already bright red. Maybe he really could reach 5 inches?!

“Seems we have a color match here,” Chloe laughed. “Girly pink is so in fashion this season.”

Finally, she patted his balls with the flat side of the ruler. Greg was dying from embarrassment. Chloe’s delicate hands so close to his pinky penis, checking how to best adjust the ruler. It came to his mind again that she had had guys with 7, 8 inches. Those cocks were even bigger than the ruler in her hand. He was sure she was silently comparing his to theirs. And still, Chloe’s face spotted the sweetest smile. She seemed to enjoy this.

“So then, let’s see how long it is: 1…2…3…oh wow, ha-ha…4…hmmm…and a little bit, right to this little heart here. Like 1/8 more. That is the proof. Then, you do have a baby penis. I will still legitimately call it my little pee-pee.” Chloe giggled.

“No way, I am sure it is at least 4 1/4 inches,” Greg protested, immediately feeling stupid to be haggling for an eighth of an inch here.

“What makes you think that? Since you’ve never measured it before,” Chloe loved having him in the hot seat.

“It’s just a feeling, you know, 4 1/4 it should have,” Greg tried a lame argument.

“Hmm, the feeling is good, but Hello Kitty is better. It is what it is, and it is exactly 4 1/8. We Koreans are very particular about numbers. I told you that.” Chloe thought about taking a permanent marker and writing down the numbers on his abs right above his little stick, but that might have been too much for him now. But she had to laugh involuntarily at her idea. Maybe other things could also be written about how she loved this. “I guess every 14-year-old with a tiny stick like this would be praying every night for it to grow more. Gosh, that’s just hilarious. But don’t worry, baby, I truly love your baby penis,” she kissed it on the head, holding it gently with her thumb and forefinger.

4 and 1/8 inches. So that was it. How could Greg be so stupid as to think he was bigger than usual today? Chloe’s generous estimation before had to have somehow misled him. Greg’s head was deep red.

“Then we both go in commando today. That’s fun” Chloe changed to the original problem that Greg had almost forgotten about.

“Yeah, I guess so,” Greg couldn’t quite share the “fun,” though.

“Unless, of course, you want to try on a pair of my panties,” Chloe gave him a challenging look. “Hm, I have never tried to get his reaction on something like this,” she thought.

“Ha-ha,” Greg was surprised and tried to sound as cool as possible but hesitated a little too long. He had never worn panties, but it kind of hit a nerve. “Err…of course not; how could I even fit into any of your S-Size panties?!”

“Oh, so if I had the right size for you, you’d consider it an option!? I will keep that in mind,” she stuck out her tongue playfully.

“Come on, I was joking, obviously,” he shot back weakly.

“Hm, you were obvious, yeah. Let’s get ready” Chloe left for the bathroom to finish her makeup.

Did she just say that he was apparent or obviously (joking)? Greg couldn’t recall her words. Anyway, he had to get dressed. He pondered which pair of pants to wear. The choices included a pair of tight jeans and slightly wider-fitting light green linen pants. Greg was worried that the shape of his little man would clearly show in the tight jeans and decided on the linen pants, which gave him a little more room.

Chloe opted for a tight grey cotton dress halfway down her knees. Decent enough, but it clearly showed her shapely braless boobs and smooth legs. And Greg knew that no panty-line meant no panty today. Chloe finished her immaculate makeup. Her beautiful face was framed by her lengthy, black and open, silky hair. “God, I look so amazingly hot, I would ask myself out,” she chuckled to herself due to this self-praise. She would be the super hot girlfriend today, standing next to him, when he, the tall white handsome guy, had to admit to a stranger that he had the tiniest little baby stick anyone could imagine. And she would happily assist if he happened to forget the exact numbers.

“Let’s go then, big boy,” Chloe chuckled and took Greg by the hand.

 

To Be Continued…?

 

*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech.