Story Time

Long Way Down

Cara has bought a new pink bra with plenty of support and a frilly maroon top just for the trip to the summer house, but it didn’t matter.  Amelia didn’t even bother with a bra, she just threw on a tank top and her boobs still looked great.  She had been on her way down the stairs when Jill told her to turn for a picture.  To her surprise, Cara had been right behind her…

Everybody Stops When They Hit The Beach  

Busty and Your Friends Know It

The demi cup bra shake is an important test…

Tinder Date

So… I had a choice last night about how I wanted to spend my evening. Netflix and Chill. Or Tinder and Fuck. Or something in between. I decided to throw all caution to the wind and hooked up with a guy I met off Tinder.

But with a different kind of guy than I normally go for.

I had changed my profile earlier in the day to say that I was looking to meet a “… a cute young PussyBoy with a pathetically small package and an extremely talented mouth and tongue who likes the taste of experienced pussy.”

I didn’t mention height or weight or race, but I knew I didn’t want someone too tall, or too heavy, or anything other than a white boy.

I had a young eager surfer boy in mind, but I was open to other possibilities.

Before the change, my profile mentioned things like “black men”, “heavy hung”, “aggressive, dominant”, and the like. But that’s not what I wanted last night.

Who knew there were so many young PussyBoys out there to choose from!

I chatted with several possibilities before focusing on one that really struck my fancy. To be honest, at first, it was his face. OMG… he was cute! Not handsome. But cute. The dimples, the sparkling eyes, the innocent smile. He was thin but in shape; not overly muscular. He was young. Only 19.

Did I mention he was ridiculously cute?

We chatted for a while. Actually, for a long while.

I asked if he knew how to surf. He said he had tried it, and liked it, but wasn’t that good at it yet.

He also mentioned he had a motorcycle. And still lived with his father; that his mother lived out of state.

He sent me more pics, including two of his penis. I told him I wanted to see one with it soft, and another one fully erect.

He complied with my request.

Normally I would have been extremely disappointed by what he sent me, and just ended the conversation, but for my purposes last night, it was perfect.

His penis looked like it belonged on a nine year old boy. All pink and pathetic. It was basically just a small fleshy nub with two walnut-sized fuzzy balls attached.

“Has anyone ever told you that you have a really small dick?”

“Not like that, no.”

“Have you ever had sex with a girl only once, and then she broke up with you?”

“Yeah. Actually.”

“Well… that’s probably why she broke up with you. She just didn’t wanna hurt your feelings by telling you why.”

He didn’t respond. We were texting, but I could hear the silence. For a moment there, I thought I had lost him.

Part of me thought I shouldn’t have told him that; I shouldn’t have been so cruel. But another part of me wanted to just be very direct and honest with him, so I could immediately control the dynamic.

“Are you still there?”, I asked.

“Yeah. I probably wasted your time. I’m sorry.”

“There’s nothing for you to be sorry about. You have a small dick. That’s okay. I mentioned in my profile that I’d like to meet a guy with a small package.”

“Yeah, but, really?”

“Yes. I’ve been with a lot of men that had really big dicks. And to be honest, they kinda hurt me sometimes.”

“Really? I thought girls liked hung guys?”

“Well… yeah, we do. But not all the time. I actually like men with small dicks. And younger, like you.”

“Have you been with a lot of guys my age?”

“Yes. Young guys are… fun to teach things to. I like their enthusiasm, and their energy. And to be honest, I like how young guys can stay hard and cum like five times a night.”

“I can go a long time.”

“I bet you could! Have you had experienced pussy before?”

“Experienced like how?”

“Experienced like… a girl who’s been with a lot of guys?”

“I guess not. I’ve only been with girls my age.”

“Experienced pussy tastes better.”

“Really?”

Yeah. Cuz it’s been sweetened up by all that fucking, ha ha.“

“Has yours?”

“That’s what I’ve been told. That it tastes like sweet peaches and cream.”

“Nice!”

“Except maybe sometimes it just tastes like black dick, ha ha.”

“Have you been with a lot of black guys?”

“Kinda. Yeah. My former boss was a black guy. He used to hit it all the time after work.”

“Your boss? Isn’t that like sexual harassment or something?”

“Yes. It was great. He harassed it every day, ha ha.”

“If you’re okay with it I guess, yeah.”

"It’s too bad you’re not a virgin still. It’s been a long time since I’ve taken a boy’s cherry.”

After chatting with him some more, and then confirming with him by telephone, I decided he might do.

I met up with him at a public place, down at the marina, which is close by, to further check him out. I needed to make sure he was legitimate, met all my expectations, and wasn’t a psycho. I needed to check his ID.

Beyond that, I also wanted to make sure he had the small endowment that his pictures promised. I couldn’t imagine he would lie about that, but I wanted to be sure.

In person, he was definitely as cute as his picture. Even more so, actually.

For a guy, he was short and thin. His profile said 5 foot six and 130 pounds. I also noticed he had small, delicate hands. And no tattoos… which was another one of my requirements.

I could also tell he was extremely nervous. Almost trembling.

We walked and talked for a while, which was a little awkward at first, but then things smoothed out. I was pretty direct with him about what I was looking for.

“Stand behind me. Unzip your zipper, and push up against me. I need to feel what you’re not packing.”

That kinda shocked him; my directness. But he anxiously did as I asked. There were a few people around, walking on the pier, but they weren’t closer than 20 or 30 feet. We were next to two high posts that kind of hid us. With my right hand, I reached behind my back, to feel him.

“Oh my God! That IS small. Are you sure that isn’t a pussy?” I laughed.

Then I turned to look at him. He blushed with embarrassment. But he didn’t say anything.

“You’ll do. Follow me back to my house? It’s pretty close.”

“Yeah!”

Twenty minutes later we were at the beach house, up in my bedroom.

We undressed.

As far as his penis was concerned, there wasn’t much of one. It was already erect, maybe three inches long, and as thin as a hot dog. Basically, like half a hot dog.

It was Perfect!

“Turn around”, I asked him. “I wanna see your ass.”

I reached out to touch it, not bothering to ask him if it was okay, cupping one of his small tight butt cheeks, in my hand. His entire body was tan, except for his ass… which made it almost kind of glow in the dim light of the bedside lamp in bedroom. It was a nice tight beautiful juicy white ass! Muscular, but not overly so. And with his messy sun-bleached blond hair…and that smile!!… he was perfect! Kevin Spacey would have probably tried to steal him from me, ha ha.

“Do you run? Do anything athletic?”

“I bike a lot. And rock climb.”

“And surf, right?”

“Yeah. Some.”

“Well… you have a really nice ass. Has anyone ever fucked it?”

He seemed surprised, and almost offended by my comment.

“No!! I’m not gay.”

“Turn around. Smile for me. Let me see your teeth.”

He complied.

“You told me earlier that you’ve eaten pussy before. But I’m curious, how many women have you serviced with your mouth and tongue?”

“Just two. Or… three.”

“Were they your girlfriends?”

“Yeah. Kinda.”

“Around your age?”

“Yeah.”

“Have you ever licked out a woman’s ass before?”

“No. Not really.”

“Well… I really enjoy that. A lot.”

He didn’t say anything.

We were standing in the bedroom, next to the bed. Naked. Just kind of checking each other out. It was strange in a way, having just met, but we both knew what we were there for. Which is one thing I really like about Tinder.

Standing in my bare feet, we were almost exactly the same height. In heels, I would be much taller.

Mostly, Surfer Boy was looking at my face, but he was also checking out my body… trying to be discreet about it.

“It’s okay. You can look.”

Unlike most other men in that situation, I couldn’t help but notice that he hadn’t yet touched me.

“But… you realize that you need permission to touch me, right?”

“Consent, yeah. Definitely. I get it.”

“Your dick isn’t big enough for you to just be able to do whatever you want with a girl. You have a little boy penis. And boys with small dicks get told what to do. Understand?”

“Okay”

“The proper answer is, ‘yes ma'am’. Do you have a problem with that?”

“No.”

“No, what?”

He caught on quick. “No, ma'am.”

As he said that, I caught him looking at my breasts, which were full and heavy. My nipples were stiff and enlarged beyond normal.

I answered his question before he asked. “I’m breastfeeding. Can you tell?”

“I… wasn’t really sure. They’re beautiful.” He was still nervous, and very shy.

“Do you wanna taste mommy’s milk?”

"What?”

“Do you wanna suck on my nipples and taste my milk?”

“Is that possible?”

“Of course it is.”

“That wouldn’t be too weird for you?”

“Uhh uhh. I’d love it, actually. I’d love to feed you.”

I invited him to touch and suckle on my breasts. He eagerly accepted my offer.

I sat on the bed, gently put my hand on his shoulder, and guided him to kneel down in front of me. I opened my legs just enough to let him get close.

“Go ahead, sweetie. You can touch and hold them. And take one of my nipples in your mouth.”

He reached out right away, with both hands, and touched my breasts. I could feel his hands shaking.

“Relax. You’re doing fine.”

“Okay,” he whispered.

“You have to kinda bite down on it with just your lips. No teeth. And suck. But gently.”

He followed my instructions. And was soon drawing my milk.

“Are you getting some?”

He paused for a moment to look up at me, letting the nipple slip from his mouth. “Yeah.”

“Go ahead. Get your nourishment, sweetie. You’re gonna need your energy tonight.”

He kept his head on my chest, sucking on my nipple.

I teased him. “Is your little dick hard for mommy?” I knew it was, but asked him anyway.

My question embarrassed him. “He mumbled a response, only momentarily releasing my nipple. “Uhhh, yes.”

“Good! I like a hard little dick. I’m gonna need you to keep it hard for me all night.”

I let him feed for a while. He started out gently at first, barely sucking on them. I told him he could suck them harder, and that if he did, he’d get more milk.

“Don’t be shy, sweetie. Right now, they’re all yours.”

That promoted him to release my left nipple, and take the other one in his mouth. This time, he sucked on it harder.

I got the feeling he would have kept sucking them all night if I had let him. But I had other plans for him.

Gently coaxing him to stop, I scooted back on the bed, with my head propped up on the pillows, and spread my legs. And gently parted my lips with my right hand, showing him the pink meat inside.

“Do you like mommy’s pussy?”

“It’s beautiful.”

“You don’t think it looks nasty?”

“No way. I love it!”

“Some men think it looks like it’s been fucked too much.”

He just started at it, but didn’t touch. Not even my legs. I hadn’t yet given him permission.

“Okay, boy. Show me how good you are with your mouth. Front and back. If you can make me cum in less than ten minutes, I’ll let you fuck me with that little pink worm between your legs.“

As he joined me in bed, I noticed his penis was still fully erect, sticking out like a thumb from below his waist.

He didn’t waste any time servicing me. He got right to it. And it felt good, although I could tell he was still nervous, and perhaps a little too anxious. And definitely not very experienced.

After a little while it started to feel better… especially after I put a pillow under my ass to lift my pussy up higher for him. But still, I could tell he wasn’t going to meet the ten minute deadline. Because, quite honestly, I was also still kind of nervous, and wasn’t quite getting there mentally. My mind was wandering too much.

Surfer Boy eventually made me cum, but it took him almost twenty minutes. And I had to give him a lot of help, telling him how to do it. It felt nice, but my orgasm was far from earth shattering.

“Mmmmm… that was really nice,” I partly lied. “Come up here. I want to kiss you.”

To be honest, the next few minutes were probably the best part of the evening. Not because he was a particularly good kisser… he wasn’t… but because I loved how I was able to totally take control of the kiss, put my right hand on his neck under his chin, and hold his mouth while I devoured him. I alternated between kissing him gently, and hard.

Then I paused to speak with him some more.

“You do have a talented tongue, sweetie. But it took you a little too long to make mommy cum.”

“I’m sorry.”

“That’s okay. It’s our first time together. I’m sure you’ll do better next time.”

“I’m sorry. I just…”

"Did you like the taste of mommy’s pussy?”

“Yeah!”

“You know, if you keep answering my questions with ‘yeah’, and not how you’re supposed to, I’m going to take a belt to your cute little ass and teach you some manners.”

“I’m sorry. Ma'am.”

“That’s much better.”

At this point we were laying down on the bed next to each other, with me partly on top of him. Looking down at him.

“Well… you didn’t earn any pussy tonight, sweetie. But you do deserve a little reward.“

His penis was still hard. And had been hard the entire evening from the moment he took his pants off.

"Have you ever had a blowjob before?”

“Yes, ma'am.”

“Do you enjoy them?”

“Yes, ma'am.”

“Well, you won’t be enjoying one tonight. You didn’t earn one. But you did make mommy come… eventually… so I’m thinking that’s worth at least a hand job. What do you think?”

“Okay.”

“Has a woman ever given you a hand job before?”

“Not really.”

“Do you want mommy to rub your little penis, and make it feel good?”

“Yes. Yes! Ma'am.”

“Are you gonna disappoint me and cum really fast, or can you make it last?”

“I can go a long time.”

“Well, I’ll tell you what. If you can last at least ten minutes before spurting, I’ll invite you back to service me next week. Would you like that!”

“Yeah! Yes, ma’am.”

“And I’ll give you another chance to earn some pussy.”

“That would be awesome!”

With that, I took his hard little hot dog size penis in my hand, and softly, gently stroked it. I was careful not to touch the head too much. That was always an extremely sensitive area for Scott; sometimes he would come almost instantly even if I just barely touched it. Which I hated because then he’d immediately go soft… if he wasn’t half soft already.

I kept talking to Surfer Boy.

“Or maybe you’ll earn a nice blowjob next time. We’ll see how you do.”

“Okay”, he said anxiously.

He ended up lasting well over ten minutes. But part of that was because I was teasing him, and sometimes only lightly touching him, sometimes just outlining his penis with the tip of my wet finger.

The power and energy of his ejaculation caused his body to arc up, and his penis to throb and spurt and come all over his stomach and chest. Some of it even got on his neck, it went up that far. I was also happy to see that he came a good amount.

After first I was thinking I’d rub his semen into his skin, and let it dry. But then I decided to instead get a warm washcloth, and gently clean him off.

I took my time doing it.

“Now. Is that better?”

“Yes, ma’am.”

We lay in bed together for a while longer. I felt so comfortable with him. He was laying on his back and I was squeezing his cute butt, and gently put my middle finger between his ass cheeks. And touched his hole. Then I put it in my mouth to get it wet, and put it back. But not inside.

“Are you sure nobody’s ever fucked this tight little ass of yours?”

He was quick to emphatically answer. “No!!” He was rather defensive about the gay thing.

“Well… maybe someday we’ll change that. Maybe someday I’ll bust your little cherry ass, ha ha.”

Fifteen minutes later he was gone.

——

Call it penance. Call it self-denial. Call it crazy. Call it perverted. Call it whatever. But I actually had a really, really good time with him.