My Best Friend's Stroker

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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superevil7
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My Best Friend's Stroker

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Description

John's younger sister, Crystal, is put in charge of his masturbation when their mom feels he is doing it too often. His best friend Dale comes to stay with them for the weekend, and now he is tempted to join his friend, letting the younger girl take control of his pleasure too.

Index

Chapter 1
Chapter 2
Chapter 3
Chapter 4
Chapter 5
Chapter 6

I've decided to change the alternate ending to the canonical ending now. I left the original ending up here if anyone would like to read it still.
Last edited by superevil7 on Mon Sep 05, 2022 6:54 pm, edited 7 times in total.
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My Best Friend's Stroker - Chapter 1

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“Holy…!! Dude!! What are you doing!!?” I could hardly believe my eyes. My best friend in the whole wide world was standing stark naked in his living room, just letting it all hang out there with everything on display! And worse both his mom and his fifteen year old sister were sitting only a few feet away, and his sister was staring directly at his private parts!

“Your friend asked you a question, John!” Oh boy. Being seventeen years old myself, I could tell the tone of a pissed off mother.

My friend looked down at the ground with shame all over his face, only managing to mumble out a few words. “Dale… I… Uh… Um…”

His sister, Crystal, began speaking for him. “I caught John playing with himself a couple weeks ago.” She had a self-satisfied smile on her face. “I had no idea what he was doing at the time.” For some reason I highly doubted that was true.

“Yes, I had to fill her in on some things much sooner than I would have liked.” His mom gave him an annoyed scowl. “I had already talked to him about the frequency he was doing that. So nasty!” She almost spit the words out. “I decided if he couldn’t handle such responsibilities on his own, then I would leave it up to his sister.”

“And now it’s time, John! So get over here!” His sister said sternly. I still couldn’t believe it. I watched as John stepped over towards his sister, almost like a condemned man. I watched as his sister took her own brother’s penis into her hands. And I watched as his penis grew to full erection as she stroked it up and down.

I had been gone for most of summer vacation, going up north to help work on my uncle’s farm. It was a tradition that had started when I was much younger. I always had a pretty good time though, and hanging out with my cousins was always a blast. As soon as I had gotten back home and settled in, my friend John had invited me to come spend the weekend at his house. After going all summer with basically no contact between us, it would be nice to catch up with him.

But I never expected to find this when I walked through his front door! John was getting to that point now. It also seemed his sister could tell, as she sped up her pumping hand. I watched in total shock as jets of his semen began flying from the end of his prick. Maybe Crystal wasn’t as prepared as I thought? She gave a surprised shriek, and some of it ended up spraying her in the face and landing in her blonde hair. But then she gave a joyous, triumphant laugh, so maybe she was expecting it, and everything had gone exactly as she had planned?

I was completely stunned into silence at that point. I couldn't imagine how embarrassed my friend must have felt. I didn’t have any siblings of my own, but I couldn’t even dream of what it would be like to be jerked off while my own mother watched. John was entirely spent, and slumped over onto the couch next to his sister so he could recuperate.

“What do you think, Dale?” His sister asked me, obviously pleased with herself, as globs of her brother’s spunk dripped from her face down onto her blouse. She turned to her brother and said, “You can go get dressed now, John.” in a domineering way.

John didn’t wait around, quickly exiting the room and heading upstairs. I know I felt deeply embarrassed for him, and that’s why I chose to just keep my mouth shut.

It wouldn’t be until later that night as we were getting ready for bed that I would learn the full truth of the situation. All throughout dinner time, and into the evening, Crystal had been making vague, or even sometimes overt references to the power she had over her brother. Like I said, I had just tried to keep my mouth shut about the whole thing, not wanting to embarrass my friend more. I could tell by the looks he gave his sister whenever she brought it up, that it bothered him a whole lot. That night however, while we were in his room getting ready for bed, he would force me to directly confront what had happened to him.

“Dale, you haven’t said one word about what happened earlier. You ok, buddy?” He was asking if I was ok?

“Am I ok? Are you ok!? I still can’t believe what happened to you earlier. Why in the world would your mom punish you like that!?” I guess being directly confronted about it made me kind of mad! To think my friend had been going through this for weeks!

“Dale, relax.” He said, and then pursed his lips as if trying to decide something. “If I tell you something, can you keep it a secret?”

“What? What is it?”

“Well, um. I’m not exactly hating it.” Now he was just confusing me. “My sister did catch me jerking off. That’s true. And my mom did punish me, like she said. But, dude, have you ever had a girl jerk you off?”

“Um… No.” I answered. He would probably be the first to know if I had, but it was still a bit uncomfortable to answer. I'd honestly had very little interaction with girls in this way.

“Well it’s fricken amazing!” He almost gushed. “And all I have to do to keep my mom and sister going along with it is to pretend to be a little embarrassed and ashamed when it happens.”

“You mean you were just pretending!?” I was flabbergasted at his admission, almost appalled.

“Don’t look at me like that, dude. It’s been the best few weeks of my life! Having a girl play with me like that, or looking at my dick and the way she seems to... Admire it… Just trust me. It’s awesome, ok?”

“But that girl’s your own sister!?”

“A girl’s hand is a girl’s hand, dude.” He said with a bit of a shrug.

“If it’s so awesome then why do you pretend to be ashamed?” It was hard to imagine he had been pulling the wool over my eyes earlier. Or over his sister’s and mom’s eyes this whole time.

“Because this is supposed to be a punishment. If my mom knew I was enjoying this she would put a stop to it immediately.”

“Ok, but didn’t your mom say you’re not allowed to jerk it yourself anymore? What if your sister just decides she’s had enough one day and decides to stop?”

“Eh, it’s not like they’re really gonna know if I jerk myself.” He shrugged his shoulders. “Besides, my sister jerks me way more often than I ever jerked myself.”

“Dude… I don’t know. Why’d you even tell me?”

“Cause you’re my best friend, and I felt like I needed to tell someone. You heard my sister anyway. If you’re spending the next few days here, you’re gonna see me getting jerked off a lot.” He gave me a toothy grin.

“Dude!” I just shook my head.

“What!? Hey! Maybe next time she does me, she can do you too. What do you think? Want a handie from my cute little sister?”

“No...! John...!” I looked at him, appalled.

“Come on, I know a part of you seems to like the idea.” He looked down towards my crotch. I was still lying on top of my sleeping bag, and the pajama pants I was wearing didn’t leave much of my erection up to the imagination.

I quickly scrambled to get into my bag. “I… How would…? No, John. Why would I…? How would we even get your sister to go along with that? I’m not the one being punished.”

“Well, I have a plan, if you’ll keep an open mind.” He said, seeing that I wasn’t completely closed off from the idea. I had to admit, getting a hand job from the cute little blonde girl, even if she was my friend’s sister, did sound really appealing.

John and I began putting his plan into action the next morning at breakfast. We waited for a time when we were alone with his mom, and would not have to reveal anything in front of his sister. What we were about to discuss with his mom would be bad enough, I didn’t want to go through it with Crystal there as well.

“Mom? I was hoping I could talk to you about something?” John asked.

“I already told you, Johnny. Your punishment is going to last until the end of summer at least, then we’ll discuss it.” His mom had always called him Johnny, for as long as I can remember. She only really called him John when she was mad with him.

“I know, mom. This isn’t about that. Dale and I were talking last night before bed, and well, because of what happened yesterday, he’s kinda worried he might be…” He looked away from his mom, playing up his embarrassment. I couldn’t help feeling embarrassed when the words left his lips. “...masturbating too much too.”

“Really?” She looked over at me. I could feel my face getting hot as she stared at me. “Dale, how often do you masturbate yourself?”

I know I stammered a little before I could answer her question, but John had prepared me for the few embarrassing questions his mom might ask, and this was one of them. Still, I couldn’t look her directly in the eye. “Probably two or three times.” I answered, then coughed in shame. “A day.” I remembered to add after a moment.

“I see. That’s just about as bad as Johnny. Does your mom know about this?” She asked next.

I just shook my head. John took over speaking for me. Thank god. “No, mom. We were hoping you would be able to help him without bringing his mom into this and embarrassing him too much.”

“I don’t know, Johnny. How can I help him? I’m not his mother.”

“I’ve always thought of you like a second mom.” I quickly said, making her blush and smile in response.

“See mom. He needs your help. Besides, he doesn’t have any sisters of his own. We’re really his only hope.” John said, laying out the rest of what we had talked about.

“Well, let me go talk with Crystal. I want to make sure she will be alright with this before I make my decision.” She left the room soon after. I couldn’t help wondering what Crystal’s response would be. Would she jump at the chance to see me naked? Or would she feel weird about seeing her brother’s best friend in such a state. Either way I was starting to feel a pain deep in the pit of my stomach at the thought.

“See dude. I told you she’d go along with it. You did a great job acting embarrassed.” My friend said, giving me a grin.

“I wasn’t really acting.” I admitted. “Are you sure this is a good idea? What if your sister doesn’t want to do it?”

“Oh come on.” He said with a laugh. “Crystal enjoys doing this just as much as I do. There’s no way she’s gonna pass up the opportunity to get her hands on you.”

“Boys! Can you come over here please!?” We didn’t have to wait long to find out. That was his mom calling us into the living room.

Both Crystal and her mom were seated on the couch when we came in. “Alright, Dale. Crystal has agreed with me that you require the same help as Johnny.” Her mom explained.

“And it’s just about time for John to have his first session of the day anyway. So get your clothes off, Johnny!” His sister demanded. John didn’t need to be told twice, starting to get his clothes off right then. Of course he was used to this by now.

“You too, Dale. Johnny goes completely naked during his sessions, so you will too.” His mom was looking directly at me, with a sternness in her eyes. I gulped hard. The only thing on my mind right then, was that this was a total mistake. Now I had to undress in front of both John’s sister and his mother! I knew I had come too far to back out now, though, realizing if I did, my friend and I would most likely end up in huge trouble. So I did the only thing I could, and took off my t-shirt.

The t-shirt was pretty easy. I had been swimming with John’s family many times over the years, so there was nothing new they hadn’t seen. I even managed to get my pajama pants down without much problem, since I had boxer shorts on underneath. I was still pretty much covered, even if I was blushing profusely at the situation. Being in boxer shorts in John’s living room felt a lot different than being in my swimming trunks at the beach, even if both basically covered me the same.

After getting that far, I kind of froze up. I just couldn’t bring myself to take my underwear off in front of these two females I’d known for so many years of my life. “Looks like Dale’s already ready.” Crystal said with a little giggle, looking at the front of my boxers. I looked down at where her gaze was leading, and realized to my horror my boner had somehow poked its way out of the front. In my mind I knew I was going to be naked in front of them in a moment, but I still reflexively used my hands to shield my manhood from their view. I was completely mortified, feeling like I had done something inappropriate.

“Relax, Dale. Johnny had a bit of a tough time his first time too. Just come over here and I can help you out.” His mom said, motioning for me to come stand in front of her. I did as she said, making sure my erection was hidden back inside my boxers before moving.

What my friend’s mom did next would be burned into my memory forever. There was no hesitation. She just reached out and grabbed my boxer shorts, and whipped them down to my ankles. My boner sprung free, right in front of her face. Both her and her daughter let out a gasp. Everyone had been paying attention to me for the last minute, as John was already undressed. So all eyes were on me, or more shamefully, on my manhood. I wanted nothing more than to clamp my hands over my privates again, but somehow I resisted the temptation this time.

“Wow, Dale! You’re way bigger than my brother!” Crystal commented, with a delighted smirk on her face.

“Hey! I’m not hard yet!” My friend complained, giving her a funny looking scowl.

“I know how big you can get, and it’s not as big as that.” She responded, pointing directly at my privates. With that I felt like I was brought back to being the center of attention.

“Alright Crystal. That’s enough. Let’s get to it.” Their mom pronounced, picking up a small bottle of lotion from the side table next to her. I hadn’t even noticed it until she grabbed it. “I didn’t know how you prefer to do it.” She said, seemingly wanting to explain herself. Then she squirted a large blob of the lotion out onto her hand, catching me completely off guard. Was she going to do me herself!? I got my answer as she started spreading the lotion around on my hard erection.

“Ooh! Can I try with some of that, mom?” Crystal looked at the bottle of lotion in her mom’s off hand, taking it from her when it was offered. Hmmm, I wondered if that meant she had always done her brother dry up to this point?

I didn’t ponder it for too long. My friend’s mom had now started to slowly and seductively stroke my hard cock up and down. I didn’t know how to feel about it at first. I had been expecting Crystal to be doing this to me, not her mother. I wouldn’t say it was unpleasant though, in fact it was feeling really good. Ok it was fricken fantastic! Maybe my friend was really on to something here?

I locked eyes with my friend’s mom. I’d seen the look on a girl’s face before. On Crystal’s yesterday when she was handling her brother, and on some of the women in the porn videos I had snuck a peek at when I knew my mom wasn’t looking, but now that look seemed to be on the face of the woman touching me, my best friend’s mom! Was she enjoying this just as much as I was? There was definitely a lustful look in her eye.

Then I looked a little lower. The first thing I noticed was that her blouse let her reveal an ample amount of cleavage. I wanted to keep my eyes there, but something drew me to take more of her in. She was wearing a fairly short skirt as well. Lot’s and lot’s of leg showing. I glanced over at Crystal, and realized both mom and daughter were dressed pretty similarly. The only difference between them was that her daughter didn’t have as much cleavage available to show off. To me it seemed like they were both dressed to be as enticing as possible, but maybe my mind was just exaggerating it because of the situation.

Turning back to her mom, I got a real shock and almost came right then! She had spread her legs open just enough that I could now see her red panties! I couldn’t see much of them, but what I could see was amazing! Her smile caught my eye for a second as she beamed up at me, seemingly knowing where I had just been looking! I think at this point I was just about as mortified as I had ever been, and at the same time, the most turned on I’d ever felt in my life!

She wasn’t just stroking me clinically, but also trying to tease me, seemingly trying to get me as excited as possible. She began doing this little thing, rubbing her thumb near where the bottom of the head of my cock met the shaft on every stroke she made. It was intoxicating and excruciating all at the same time! Every once in a while she would lightly tickle her fingertips on my sensitive scrotum too. She only had to stroke me a few more times, and it was all over! I felt like I was cumming buckets! She was prepared though, placing a tissue to catch my jiz, apparently not wanting to get as messy as her daughter did yesterday.

She stood up, and helped me to sit down in one of the chairs. I looked over to where I expected to find my friend, but Crystal had already finished with him. He was already slumped over on the couch next to her, trying to catch his breath just as much as I was.

“Alright boys. You can get dressed once you’re able.” My friend’s mom said, looking directly at me with a small smirk on her lips. I can’t be sure, but I could have sworn I saw her giving me a wink before leaving the room.

“You boys don’t have to get dressed.” Crystal said, smirking as much as her mother had been. “I’ve seen it all, so there’s really no reason.”

“Ha! Yeah right!” John said, as he got up from the couch. He collected both of our clothes, then offered a hand to help me out of the chair, and the two of us went off to his room.

Before we could even get dressed, I had to exclaim to him, “Dude! What the hell was that!? I thought your sister was going to be the one doing that?”

“I don’t know?” He dropped our clothes onto his bed, and then shrugged his shoulders. “I didn’t expect that either. I was just as surprised as you are. I mean, my mom, doing that..!” He looked a little wide eyed.

I walked over and started separating our clothes. “I do have to say, it was really awesome!” I couldn’t stop myself from giving him a big grin.

He shook his head. “Dude! That’s my mom!” He chuckled, so I knew he wasn’t really angry with me.

“Yeah. Who knew your mom could give such great handies! And she’s not half bad looking either!” I razzed him a little.

“Ewww! Gross! I don’t need to know you find my mom hot!” He had that same funny scowl on his face from earlier.

“Says the guy perving on his own sister!” I shot back at him.

“Hey! I don’t think about my sister while she’s doing it, I think about…”

“Wendy Harper?” I interrupted him before he could even finish.

“Yeah, of course.” He responded, not even fazed. “And some day you’re gonna tell me which girl you fantasize about when you do that.”

“I told you, I don’t have a crush on anyone at our school.”

“Yeah, well. You must have a crush on someone, since you always turn bright red whenever I bring it up.” He said, smugly.
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My Best Friend's Stroker - Chapter 2

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Things claimed back down, at least until lunch time. It was the first time we had seen his sister or his mom since the session that morning, since we had decided to just hold up in my friend's room for the remainder of the morning. At the moment it had felt absolutely amazing, being jerked off by my friend’s mom, but now after the fact, I didn’t know how I was going to face her again. Or my friend’s sister, Crystal, either. She had been there to witness my striping and wanking as well. Walking into that kitchen, I felt like my face was ablaze.

My friend’s sister was the first one to say anything. “Awww, I guess you boys are still feeling a little modest. You didn’t want to take me up on my offer and stay naked?”

Her mom turned to give her a stern look in the eye. "Now Crystal, you know this isn't meant to embarrass the boys; it's meant to help them get their little problem under control. We're just giving them a helping hand." At first I thought she was scolding her daughter, but then she began to giggle at what she had said.

I just took a seat at the table bashfully, but John seemed determined to one up his sister in the conversation, whispering to her when her mom wasn’t looking. "You'd like that, wouldn't you? You get off on the thought of seeing my dick and playing with it.", Crystal turned her eyes downwards at her plate, then looked back up, squinting her eyes at him. John continued speaking quietly before she could say anything. “Although you never asked me to do that over the last couple weeks. No, it’s Dale you’re interested in seeing more of. Isn't it?” She turned bright red in response to that, and looked at her brother with wide eyed shock. Then she glanced over at me for a second before averting her eyes away.

“What are you whispering about?” John’s mom asked him with a suspicious smirk. John just shrugged his shoulders to his mom as she sat down, and started dishing out the plates. Nothing much else was said about the topic during lunch, and I won't bore you with the details of their mom's shopping list.

It was after lunch that things picked back up again. Crystal seemed determined to get back at her brother for the comments he had made towards her. "Alright boys. Time for another session. Follow me."

She led us into the living room, the same place where just that morning her mom had stroked me off. It seemed like this would be the standard location for all of our sessions. I noticed her mom hadn't come with us this time. I had mixed feelings about that. On the one hand, if she wasn't coming that meant she wouldn't be giving me another glorious handie. On the other hand, that probably meant Crystal would be the one handling me this time. I was already completely erect at the thought of my friend's sister touching me!

"Get undressed boys." Crystal said, matter of factly. Well, she had the hint of a smirk on her lips.

It was hard for me not to feel a knot in my stomach at the thought of stripping naked for her. Even if I had already done it once before. I had always liked the little blonde girl, from the age of eight when her brother had introduced us, all the way until this moment. A few years ago, I had started to notice the changes in her body. How her boobs had grown, and how her hips had swelled. I hate to admit it, even here, but I have always had a huge crush on my best friend's little sister. Yes, I admit it!

She didn’t go to our school, at least not yet, so I wasn’t technically lying to John. She will be going there starting this year, but classes haven't begun yet. We were dressed in our everyday clothes now, which for me meant a t-shirt and athletic shorts. John had jeans on instead. I have no idea why I did it, but I began with my shorts. It was one of those weird mistakes you just can’t explain, but I already had them down to my knees before I even realized what I was doing. It would be stupid to pull them back up at this point, so I just continued. John already had his shirt off, and was undoing his jeans, as I stepped out of my shorts, and I’m sure I gave him a look as if to ask, ‘What are we even doing!?’

“Dale, you have really nice legs.” Crystal said to me, having taken her seat on the couch. She had her arms up on the backrest on either side, and she gave me just the wickedest of grins as she looked from my bare legs to my face! I felt like I was going to fall over!

“Come on, dude. Catch up!” John got my attention. He was only wearing his boxers now, apparently already getting his jeans off.

I wasn’t going to do my boxer shorts next, so that meant I had to lose my shirt. Just like at the beach, I tried to remind myself, but my face felt like it was on fire again. It didn’t help that Crystal seemed to be staring at me so intently with that sexy little smile of hers!

With my t-shirt off and out of the way, that just left my boxers. I had just pushed them past my hips, when the damn doorbell went off! I think I jumped right out of them!

“Now who could that be?” Crystal said, getting up from the couch, grabbing my boxers from the floor, along with her brother’s. She had the most mischievous look on her face as she headed to check the door.

“Relax dude.” John said, seeing the panic on my face. “She’s done this to me a couple times. It’s always just been a solicitor. She’s just trying to mess with us.”

“Well she’s doing a pretty good job…” I whispered, feeling my heart going a mile a minute.

“Oh boys!” Crystal sang behind us. We were still facing the couch at the time. “Look who’s come to visit!”

We both turned around, and there was Windy Harper! “Wendy!!!” John called, and immediately grabbed his manhood to hide it with his hands. I’d never seen such a look of panic on my friend’s face before.

I was just stunned for a few seconds, but then I realized that I too was naked in front of Wendy! I quickly covered up as well as soon as it hit me. Sure, I didn’t have a crush on Wendy like my friend did, but she was still a girl from our class! And now she had seen me naked!

“Why are the boys naked!?” Wendy seemed to be just as shocked as us at first. She looked like her eyes were about to pop out of their sockets! It didn’t take too long for that shock on her face to change into a smile, as she could see the compromised position the two of us were really in.

“The boys were having a bit of a problem with masturbation.” Crystal started to explain to her.

“Crystal!!!” John complained, turning very red now.

Crystal just continued, ignoring her brother like he wasn’t even there. “It seems they were doing it way too much. My mom put me in charge in order to break their nasty habit. Now they are no longer allowed to do it themselves. They have to wait for me to do it for them, when I decide it’s time.”

“Oh my god! Really!?” Wendy giggled, looking to both of us again, seemingly for confirmation. Neither John or I were able to say anything, we were both too afraid and humiliated to be in front of her like this. Without any damn clothes on!

“Yep, it’s true.” Crystal giggled as well, sort of skipping around us to get between us and the couch again. “It’s a good thing you showed up when you did.” For some reason I highly doubted that. This was just way too convenient! Somehow she must have figured out something about John’s crush on Wendy!

“Why?” Wendy asked.

I looked back over my shoulder at Crystal, catching her staring at my bare backside! I don’t think she had any shame about what she was doing, as she just looked back up at me with another smirk. “Because there are two boys to do. My arm gets tired enough just doing one of them.” WHAT!? She couldn’t mean…!?

“You want me to jerk one of the boys off!?” Wendy asked her in wonder, ping ponging her head back and forth between Crystal and us. It was making her long golden brown hair fly all over.

“Yep.” Crystal answered as she sat down on the couch and crossed her leg, giving a big grin to the girl. “You can do my brother. I’ve been waiting all day to get my hands on Dale.” She looked me directly in the eyes and licked her ruby red lips. I just about died! I was the most erect I had ever been in my life!

Crystal got back up, and stared us boys down. “No more covering up, boys!” She commanded. “We can’t jerk you with your hands in the way.”

I don’t know why, but I felt compelled to do as she said. I dropped my hands, and after a moment I heard a small gasp. “He’s so big…” I looked over to see Wendy staring down right at me. Right at the privates between my legs. Well, I guess they were no longer private to her.

“I know!” Crystal gushed with another beautiful smile. My legs were getting weak again. She reached out to take my hand, and then ushered me across the room until we were standing in front of one of the chairs. “Johnny!” She turned back to her brother. “Drop those hands! Now!”

I could see John give a shudder, before he too uncovered himself. He was now just erect as I was. Wendy walked a little closer to him, to take a better look. “Nice, John…” She said with a deep red blush on her cheeks.

“Uhhh…” John didn’t seem to know what to say.

“Say thank you to Wendy for her compliment, John.” His sister commanded.

“Um, thanks Wendy.” He mumbled, keeping his eyes averted from her face.

Suddenly there was a hand brushing on my thigh, trying to get me to turn around. It was Crystal. She had taken a seat in the chair. She smiled up at me with just the cutest, but most self-satisfied smiles I had ever seen, as I faced towards her. Now she was eye level with everything down there. This was the first time she got to see me up close and personal. She slowly reached out and wrapped her fingers around my cock, still not breaking eye contact with me. I gave a big gulp in response. “You ready, Dale?” My god, she was so cute and sexy! I don’t know how I was still on my feet. I just nodded a small nod, as anything more and I would have surely fainted on the spot.

She started very slowly, just using the skin on my shaft to pump up and down, but at an agonizing pace! After only a minute I wanted to hump my hips so badly! I was twitching and squirming all over as her hand teased me! “Slow down.” She whispered to me. “Hold more still.” I did my best but she was driving me wild!

Then she did something totally out of left field. I mean, I had no indication she was about to do what she did. She stuck the tip of her tongue out, and then leaned forward. Without a word she ran the tip of her tongue around my glans, one, two, three times! I almost came right then! Leaning back in her chair, she gave me that wicked mischievous grin again! “Ooh, you liked that!” She purred, going back to stroking me again. At this point I totally lost it! She no longer needed to move her hand, as I was doing all the work! In just another moment, I was spraying her in her face and her blonde hair with copious amounts of my seed!

“Oh Dale!” She giggled in delight, seemingly sticking her neck out a little more, to take my spunk right in her face.

“OH, FUCK! CRYSTAL!” I moaned, as the last of it came out. Then my vision blurred and I collapsed down to the floor, totally spent!

I don’t know how long I was down for, but eventually Crystal took my arm, and started helping me to my feet. “Here, let me help you.” She guided me into the chair she had been seated in.

“Oh my god!” I was still trying to catch my breath as I looked up at her in complete wonder. She just gave me another cute smile. Apparently John and Wendy had just been watching us the entire time, as both of them were staring at me with slacked jaws. The only reason I knew they hadn’t done anything yet is because John was still fully erect.

Crystal left the room for a minute, and came back holding a glass of ice water in one hand, and a washcloth in the other. Apparently she had washed her face while she was gone. “Here.” She handed me the water, which I was very thankful for. Then she surprised me by getting down onto her knees in front of me, and put her elbows on my thighs. She reached forward and took my now flaccid penis into one hand, and as softly and sweetly as she could, she wiped it clean with the small wet towel. It was like this pure act of kindness and consideration I’d never known I’d wanted in my life until now.

After she was finished cleaning me, she turned her attention to the other two in the room with us. "Oh Johnny, Wendy. It's your turn." She said in that singing voice again.

"Us!?" Wendy has a pretty cute blush if I'm being honest, and she had it right then, looking from Crystal to John again and again.

John seemed just as mortified. "Maybe we can skip this one, Crystal…" He almost sounded like he was begging.

"Nope. It needs to be done. Or I know you will be sneaky and jerking yourself off again." Crystal said, placing her hands on her hips. Then she just started both of them down.

"I guess we don't have a choice." Wendy said, eyeing John's face a little.

"Ummm… I guess not." He was the one gulping now, as he stood naked in front of his crush.

"Take a seat Wendy." His sister said. Neither of them had made any movement so I think she was getting impatient. "Now John, stand right in front of her just like you do with me." She demanded. "Wendy, have you ever played with a boy's cock before?" It sounded so weird yet so hot to hear her using such coarse language.

"No…" Wendy shook her head just a little. Ever since John had moved in front of her, her eyes had stayed locked onto his throbbing cock jetting out towards her.

"Ok then. Well why don't you use a bit of lotion. It will make it easier to do for a beginner like you." She skipped over towards them again, producing the little bottle of lotion in her hand. I had no idea where she had gotten it from. "Open your hands for me." She said, and then emptied a big dollop of the cream into Wendy's outstretched hands.

"Now spread it all over Johnny's big, meaty, throbbing, hard cock for him." I think she was trying to embarrass them, but damn did that sound hot to me!

Wendy was very cautious as she completed the task. Now she seemed to be the one totally bashful, and she wasn't even the one naked in front of her crush. John was facing away from me for the most part, but I could still see that he seemed to be in a mix of pure elation at his crush actually touching him, and complete humiliation at the same time. One thing was for sure in his expression, he was still not over the fact that his crush had all of a sudden caught him so compromised.

"Good. Now go ahead and start massaging it all over. This is your time to have fun and really get to know Johnny's penis. Try and find where he is most sensitive, and what makes him squirm and wiggle his hips. Try to see what makes him moan."

"Ok." Wendy said with a blushing smile, as her hands started to explore. "Oh, I think he's sensitive there!" She said with excitement since she had gotten John up on his tiptoes.

"Oh yeah. But the real sensitive part is that head on the end. Try Twirling your finger around it a few times and see how he reacts."

"OHHHHH!" John moaned. Now he was losing his embarrassment and getting into it.

"Oh this is pretty fun!" Wendy laced her fingers together around the shaft of his cock, and then she started using her thumbs to massage the head.

"Oh please, Wendy! I'm so hard already! Please just jerk me!" He began to beg.

"Shhhh, Johnny!" His sister scolded. "Wendy is still exploring. She'll get to it when she is good and ready and if she wants to. Wendy, you just keep doing whatever you want."

"Ok!" Wendy said with a wide grin, starting to realize she was the one in charge here.

"Wow, it can get so hard!" Wendy said with some astonishment. "I thought it was already hard before, but look at it now, Crystal!"

"I know. He seems to be giving Dale a run for his money now." Crystal smiled over at me, then down at my cock, which produced a blush from me. It made me realize I was still sitting there naked in front of them.

Wendy continued her exploration of John's privates, despite all the moaning and pleading he was doing. She was totally into it now, taking pleasure at the way she had learned she could make him wiggle and writhe around. All with just the lightest touch on his swollen, sensitive appendage. I even saw her massaging his balls a little, with a look of pure joy on her face. I could tell she had gotten over any shyness she was feeling. I had witnessed Wendy's transformation from a bashful sweet girl, to another expert dominator of the penis like Crystal. "How do I jerk him?" She finally asked, and I swear I heard a sigh of relief from my friend.

Crystal gave a big smile to me and then a wink, then she addressed the other girl's question. "You just hold it in your hand. Yep, like that. Then you slowly stroke up and down my big brother's meaty, delicious cock." She teased them again, making her voice sound breathless. I couldn't help laughing to myself a little.

Wendy seemed to pick it up quickly. She had him squirting all over himself in a moment. I couldn't blame him for cumming so quickly, he had practically been being tortured by his crush for the last fifteen minutes as she had explored every millimeter of his cock. John almost collapsed just as hard as I had, but he had the couch to fall onto, ending up in between the two girls.

"Wow!" Wendy exclaimed, still keeping her eyes locked onto my friend, more specifically his privates.

"I know…" Crystal gushed. "It's so fun to play with a boy's cock!"

"So it's up to you when they need to be played with again?" Wendy asked. "Would you like me to stay and help you some more?"

"Oh yes. Of course I want you to stay and help, Wendy. But it's not just for today. The boys are going to need us to take over this responsibility for them for at least until the end of summer vacation."

"Oh my goodness! So I can come see your brother naked and play with him again tomorrow too!?" Wendy seemed to be getting giddy.

"Uh hum." Crystal nodded her head with a smile to the older girl. "Not just tomorrow. The whole rest of the summer!"

"Hey, don't I get a say in this!?" John complained, sitting in between them.

"Nope. Your cock belongs to me for the rest of the summer, brother." She took it into her hand and waggled it around a bit. "And I've just decided I want to give it to Wendy."

"What!? You mean it!?" Wendy asked in joyous surprise. When Crystal nodded her head, Wendy grabbed her in a hug, with John still sandwiched in between them. "This is so cool! My very own cock!" She took it in her hand now, just holding it. "I'm gonna have so much fun with your cock, Johnny!"

Crystal got up and stood in front of me. "I like Dale's best anyway. So I'll be keeping his for myself." She smirked down at me with that mischievous look in her eye again. I could do nothing but gulp up at her.
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Re: My Best Friend's Stroker

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I'm really enjoying this story, many thanks for writing it and I hope there's a few more chapters remaining.
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Re: My Best Friend's Stroker

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SydneySub wrote: Wed Aug 03, 2022 12:55 am I'm really enjoying this story, many thanks for writing it and I hope there's a few more chapters remaining.
Thank you SydneySub! If you don't mind me asking, which part did you enjoy the most?
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Re: My Best Friend's Stroker

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No problem at all, the clear winner of my favorite part so far was how brazen and impulsive Crystal was to blow Dale and his response was quite warranted.
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Re: My Best Friend's Stroker

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I love this story! Is there more?
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Re: My Best Friend's Stroker

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Lola wrote: Thu Aug 04, 2022 8:35 pm I love this story! Is there more?
There will be, but it's not finished yet. And thank you! Glad you liked it.
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My Best Friend's Stroker - Chapter 3

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With another one of her sexy smirks, Crystal took a seat on my bare lap, and then took my cock into her hand. Wow, she smelled so good! "This is so nice. Having my very own cock to hold, and a nice strong sexy boy's lap to sit in." She gave me a smile, gripping me a little tighter. Damn it was so arousing to have her in my lap like this! I could feel myself getting hard in her hand.

"Ooh! I wanna try!" Wendy said, and then she got on John's lap, taking his flaccid penis in her grasp. "Ooh, so comfy!" She giggled.

"Oh is it time already?" Crystal's mom asked as she spotted me and Crystal, coming into the room. "Wendy? What are you doing here, dear?"

"Crystal invited me… into the house. I came over to see if Johnny had gotten his class schedule yet. I wanted to see if he was in any of my classes this year. But I never expected to find him like this!" She giggled, wagging John's penis at his mother.

"Oh yes. Johnny's had a bit of a masturbation problem. I was hoping having his sister take over would cure him of his excessiveness."

"Wendy offered to help once she saw Johnny, and I explained everything to her, mom." Crystal told her from my lap. I could not help feeling like this was a bit too intimate of a position for her to be in front of her mom, but her mom didn't seem to mind. Now my cock was back to being totally hard with her in my lap too, and I couldn't help blushing as her mom came over to take a long look at it.

"Well thank you for your help, Wendy. We really appreciate it. Crystal was going to have her hands full dealing with both boys this week while I'm at work. It's always nice to have another helping hand around, isn't it Dale?" She had come to stand right in front of me and her daughter now. Then she reached her hand out, and Crystal released her grasp for a second to let her mom stroke me a few times!

"Uh… um…" I didn't know what to say, with her holding my hard cock.

"But you can always come to me too, Dale. Don't be shy with me. I'm always willing to help you in satisfying this need of yours!" This time I for sure saw her wink at me, and I just about came, but then she released me from her clutches! "I'm heading to the supermarket now, kids. I'll be back in a few hours. Boys, listen to Crystal. When it's time for your next session, do what she says." She said heading out.

Now that her mother was gone, Crystal took my hard cock back into her hand, just lightly stroking me so I stayed hard. She wasn't trying to get me off, at least not yet it seemed. "Isn't this nice?" She grinned at me, and then Wendy. "Finally we seem to have cured these guys of their modesty. I've been telling them they should just stay naked for me. I mean I've already seen it. What's to hide?"

"Oh, that's a good point, Crystal. We have already seen everything." She turned back to look at John. "Your sister's right. You should just stay naked." She said with a laugh.

"Wendy, please…" John had been bright red ever since his crush had gotten up onto his lap.

"No, come on. Your sister said your cock belongs to me anyway. I think I get to decide whether it is covered or not." She smiled, and then stuck her tongue out at him.

"Wendy…" He said more seriously.

"Nope, this cock stays bare. And I suppose so will the rest of you have to stay bare too! You'd look silly wearing your clothes but leaving your cock out." I could see she was just teasing him, but it looked like John was getting mad.

"Get up, Wendy!"

"No, I'm still enjoying your cock too much right now, Johnny. Maybe in a bit." She smirked at him.

"I said get off of me!!" He said forcefully, yelling at her this time. Wendy seemed shocked, and almost like she didn't know what she had done wrong, quickly getting up. She seemed to get a little pale as she stared back at him. Crystal and I were both shocked at his outburst as well.

John got up and grabbed his jeans. "Where are my boxers!?" He demanded. "Whatever!" He said, pulling his jeans on without. Then he quickly grabbed his shirt as well. "You coming, Dale!?"

He looked at me, with his little sister still sitting on my lap. I honestly didn't want to go. I was really starting to have a good time. But I could tell he needed me now. "Sorry Crystal." I said, and she seemed to get the message. She got off of me, and then I quickly grabbed my clothes and followed my friend up to his room.

I was about to unload on him for interrupting things, once the two of us were alone, but then I noticed the look of fear and sorrow on his face as he leaned up against his bedroom door once it was closed.

"I know. Wendy…" I said with understanding, letting him know I could feel his pain.

"Why Wendy? Why did it have to be Wendy!?" He almost sobbed.

"You know why. Crystal must have learned of your secret. She must know you like Wendy."

"And she just wanted to torture me!" He said with anguish.

"No. I don't think so. Come on. They were just having some fun with us."

"Some fun!? Crystal wanted to humiliate me in front of Wendy! Parade me naked in front of the girl I like!"

"Was it so bad, honestly?" I asked him. He didn't know it, but I had just spent a copious amount of time naked in front of my crush, in front of his little sister, Crystal. Yeah it had been embarrassing at first, but I had honestly started to like it. This was all his idea anyway. I get that he was upset for Wendy to see him naked, but there must have been some part of him that took joy from getting jerked by the girl he likes, like I just did.

"Yes!" He complained.

"You’re going to tell me you never fantasize about having Wendy jerk you off?" I countered.

"Yes, but… I mean nothing like that. It's always… But you heard her, she was saying all those crazy things. Owning my cock!? Why the hell would she say something like that…!?"

"Hey, calm down. She was just teasing you, and having some fun. I think she was just following Crystal's lead."

"You think so?" He seemed to be genuinely confused now.

"I don't know man? Let me go talk with them. See what's really up." I said, and he just shrugged his shoulders, but nodded his head. Very quickly I headed back down the stairs.

The girls were still in the living room, giggling to themselves as I approached. I decided to do a little eavesdropping to see if I could find out their real agenda and hid around the corner where they couldn't see me.

"That was so awesome! Thanks for inviting me over, Crystal." I knew it! Wendy had just admitted that Crystal had invited her here.

"You're welcome! I knew you’d like seeing Dale and Johnny naked. It was really fun, wasn't it, touching a boy like that?"

"Oh my goodness, your brother's dick was so cute! It was so sensitive too! I was having so much fun with him!"

Crystal let out a small laugh. "Oh I could totally tell you were enjoying it. My brother on the other hand…"

"I know. It seemed like he was really enjoying it at first too, but then he got so upset at me. I'm really worried about that. That he's so angry with me, that he won't want to have anything to do with me anymore. Do you think I went too far? I was only trying to tease him a little, the way you were teasing Dale."

"I know. I'm worried too. I've never seen him get so embarrassed or upset like that."

"Really?"

"Yeah. He wasn't even that embarrassed the first time he stripped naked for me and I jerked it for him. He's been really enjoying this whole thing the last couple of weeks, even if he always denies it to me. I wonder why he got so embarrassed today?"

I couldn't take anymore of this, and came charging into the room. "You know exactly why!"

"What?" Both girls looked up at me mystified, startled I was even there. "Dale, you're still naked…" Wendy said, and both girls' expressions changed from shock to wide grins.

"I guess I forgot…"I blushed a little, but pushed through. "That doesn't matter right now!" I said in frustration. "You know exactly why John would be embarrassed to be naked in front of Wendy, Crystal!"

"What? No?" Crystal just seemed confused at my accusation.

"Of all the girls you could have invited over, you just chose Wendy for no reason at all!?" Now I was feeling a little mad at Crystal. Mad for my friend and what she had put him through. I wasn't going to let her get away with this!

"I know she's a girl from your guys-es class, but you aren't even as embarrassed as John was, Dale." Crystal said, looking down at my exposed package again.

I quickly covered myself up so she wouldn't get distracted while we talked. “Yeah, because you know how John feels about Wendy!”

A look of realization flashed across Wendy's face. "He likes me!?"

"Of course he likes you! That's why Crystal invited you over today! To humiliate him in front of the girl he likes!"

"What!? I had no idea!" Crystal looked at me with genuine shock at the revelation.

"But…? But…?" It slowly dawned on me that I had just betrayed my best friend's secret, and right to the girl he likes too! "Why would you invite her over here then!?"

"Because Wendy lives in the neighborhood, and she's the closest girl in your class I could think of to invite." Crystal explained. “I wanted to tease you guys a little, not make John feel humiliated.”

"Johnny really has a crush on me!?" Wendy got that cute blush on her face, this time with a big smile.

"Yeah…" I began rubbing the back of my neck in nervousness, wondering what would happen next, now that they knew his secret.

"I kinda have a bit of a crush on Johnny too." Wendy said, and now her cheeks were really glowing. "Especially now that I've seen him naked!" She added with a giggle.

I was at a loss for words honestly. I still felt awful for letting John's secret slip like that, and a little embarrassed about accusing Crystal too. Here I had thought Crystal had actually been trying to humiliate her brother by inviting his crush over to watch him get naked and jerked off. No, she just wanted to tease us a little by baring us in front of our classmate. I thought about speaking up to say that was probably almost just as bad, but truthfully, it didn't seem like as big of a deal as the other thing.

Crystal seemed to realize that maybe it had been a bad idea to invite Wendy over as well. "Do you think I should go apologize to Johnny?"

"I mean, I don't know…? I think he just needs time. Time to get over it." I explained.

"You seem to be over it already." Crystal glanced down at my limp penis, exposed once again as I had let my hands hang at my side after the revelation. She let out a tiny cute giggle at me.

I blushed at them, very tempted to cover up with my hands again. They had already seen everything though, so I didn't really see the point. "I didn't mean to come back down like this. I just kinda forgot to get dressed." I tried to explain myself, but it sounded ridiculous even to me.

Wendy surprised me by speaking up. She had really come out of her shell fast. "We really don't mind, Dale. We think you look great like this. Johnny too."

"Yeah, we're both serious. You guys are both so hot naked!! If you guys were to stay naked, not only would we not mind, but we'd really like it too!" Crystal added, then she blew me a little kiss, and gave me a wink.

"I'll uhhhh… Have to think about it…" I said, feeling baffled by her invitation. "I better go check on John." I said as my excuse to leave the room.

“So, what happened?” John asked me as I came back into his room.

I immediately went for my clothes this time. I wasn't going to let myself make the same mistake twice. “Crystal didn’t invite Windy over because she knew about your crush. She invited her over because she lives so close.” I explained to him. “She wanted to tease us a little with Wendy being in our class at school, but she also thought we would have fun because of that too.”

“Fun?” He asked, giving me a confused look.

“Yeah, you know. Wendy’s a cute girl from our school. She thought it would be exciting for us to be naked in front of her and to be touched by her.”

“So neither of them know about my crush on Wendy?”

I had hoped he wouldn’t ask me that. “Well…”

“Well what?”

“They might have figured it out.” He gave me a panicked look. “I mean the way you stormed out of there, and how I confronted them…” Now he looked shocked. “Ok, maybe I slipped a little.”

“You told them!!?”

“Not outright. But, yeah, they both know…” I said, feeling really bad. He stood there, staring at me, looking beet red. I wasn’t sure if he was going to hit me, or throw me out. “But, look.” I said quickly. “Wendy says she has a crush on you too.”

Suddenly his mood shifted. He was still shocked, but in a good way. “Really!? She said that!?”

“Yeah. It was the next words out of her mouth after I let your secret slip.”

Now he seemed to be really happy. “Really? Really!?” Apparently he was still having trouble believing me. “Tell me exactly what she said.”

“Ok. After I let it slip, she said she had a bit of a crush on you too.”

“A bit of a crush?” He complained.

“Come on. You know how shy Wendy is. If she says she has a bit of a crush on you, that probably means she’s madly in love with you.”

“Shit, you’re probably right!” He said with a big grin. “What else did she say?”

I had a little chuckle. “She said she really likes you now that she’s seen you naked.”

He seemed to puff his chest out a little. “Damn…! Who woulda thought…!” Then it seemed like he got another idea. “Maybe this would work for you too.”

“What? What do you mean?” I asked.

“Well, deny it all you want, I know you have a crush on someone. Maybe my sister could invite her over, just like she did with Wendy.”

“What!? John…”

“No. Think about it. You could let her see you naked, and you could get jerked off by your crush, just like I did. It really was awesome, you know. Especially now that I know she likes me! I can’t wait for her to do it again!!” He said with a large smile.

“Look, just drop it. I don’t…”

“Come on man! I know you! You so have a crush on someone! Who is she? Or is it a he? If it’s a he, that's totally cool…”

I cut him off right there. “No it’s not a he!!”

He just laughed. “Then who is she?” Damn! He had just tricked me into admitting I have a crush on a girl.

“Look, can we just drop this!?!”

“No! I’m your best friend, and that gives me the right to know what girl you have a crush on!”

“I just…” Could I really tell him? Tell him I was basically in love with his little sister? “I don’t think you’ll like it if I tell you.”

“Look, unless you’re going to tell me it’s my mom or my great aunt Francine, I don’t care.”

I went and sat on the edge of his bed, resting my chin in the palms of my hands. “Alright. I tried to warn you, but you kept pushing. You’re not going to like it…” I softly mumbled her name out, “Crystal…”

“Crystal? The tambourine girl in the marching band?”

“No, you idi–…! Crystal Robinson… Your sister…” I was too afraid to look at him at first, and just stared down at my feet. The silence defending. It went on too long for me, and I eventually worked up enough courage to look at him. He was just staring at me with his jaw hung open. “John… Say something…”

“My sister???” He didn’t seem mad, so maybe that was a good sign. “You like my little sister?????” He still stared at me in shock for a very, very long time. An uncomfortably long time! Then suddenly he burst out laughing. “Hahahahahaha!!! Crystal!?!?!?! My little sister!?!?!?” He went into deep belly laughs, almost convulsing he was laughing so hard. “Oh my god! Oh my god!!! And here I got you to get naked in front of her!! Oh man!!! No wonder you’ve been acting so weird this whole time!!! You like my sister!!” All the while he just kept laughing at me.

“What’s so funny!?!?” I demanded to know from him.

He had tears in his eyes now, he was laughing so hard. “Dude! Dude! My sister!?! Damn!! Either you guys are gonna be a really cute couple, or she’s gonna eat you alive!”

“What the hell does that mean???”

He finally seemed to be getting his laughter under control. “Crystal’s totally got the hots for you, or haven’t you noticed? She was practically salivating the first time you were naked in front of her. You were too focused on my mom, but the whole time she was doing me, she was infatuated with watching you.”

Now I was the one looking at him with confusion. “She was?”

“Dude, did you forget what I said this morning at breakfast? She totally wants you! She never asked me to stay naked once after our sessions together, but the minute you show up and it’s all,” He put on a fake girl voice, “Oh, Dale, can’t you stay naked for me? Oh please, Dale! Just stay naked for me for a little while longer! Pretty, pretty please?” and he fluttered his eyelids, doing a bad impression of his sister.

It still got a small laugh out of me though. “I’m the first guy she’s seen naked, besides you. And you’re her brother, so you don’t really count.” I was pretty skeptical Crystal would ever like me that way. I was pretty sure she was just teasing me earlier. "I don't know, dude. I think you are reading too much into it."

He came over and patted me on the shoulder a few times. "Dale, Dale, Dale… What am I going to do with you?" He chuckled and shook his head. "Listen, I'm going to go get a quick shower. I'm still all sticky and crusty from earlier. Wendy wasn't really all that good with her aim. She got it all over my chest and stomach." He said, walking away from me.

"Give her a break. It was her first time!" We both laughed at that as he headed out his bedroom door.

I headed out too, going downstairs. No sense just sitting in his room doing nothing. Crystal and Wendy were still seated on the couch as I came in, having a quiet conversation with each other. "Hey girls."

"Awwwwww…" They both moaned. "You're dressed." Crystal complained.

I blushed at them. "What is your infatuation with me being naked?"

Now it was Crystal that was turning red. "We both think you are hot. Simple as that."

I felt pretty flattered, especially hearing that from the girl I like. "That true, Wendy?"

"I… Um…" She just nodded her head.

"So where's Johnny?" Crystal asked. "Is he feeling any better?"

"Yeah. I explained everything to him, and he seems over it now. He said he was going to take a shower."

"Oh, ok…" Crystal said. Then she got that mischievous smile on her lips. "I think it's time for another session, Dale."

"Wait what? Already?" I asked, suddenly feeling myself starting to rise in my shorts at the mere suggestion.

"Oh yes. You were totally hard earlier, before Johnny stormed off, and I'm afraid you're going to try and take things into your own hands if I don't finish what I started." She explained to me. “Now, clothes off. I’ll have you taken care of in no time.”

Both girls just smirked at me, waiting for me to get undressed. I guess I didn’t feel like I had a choice in the matter. I quickly slipped my shirt off. “WHEW!!!” Crystal cheered and giggled. It gave me a bashful pride as I slid my shorts off. “Yeah!! Take it off!!” She yelled.

“Yeah, Dale! Get those boxers off!!” Wendy added with a blushing smile. I didn’t hesitate, giving them what they wanted. My erection was already sticking straight up as I took a few steps to get closer to them, anticipating Crystal’s soft hand on me again.

Crystal seemed to have another idea though. “Before we begin, I’d like you to do something for us.”

“Huh?” I asked, feeling that bashfulness creeping back in with them both staring at my hard appendage.

“Do ten jumping jacks, and then I’ll jerk you off.” Crystal said with that sexy smirk.

“Ten jumping jacks?” I asked, not really nervous, but more anticipating her getting her hands on me. “Ok. Here it goes.” I started jumping up and down, counting each jump out loud as I did it. “1, 2, 3…” My hard erection bounced up and down, right in the sight line of the girls who just squealed in delight as they watched me. “10… And one more for good luck!” I made one more little jump. I had honestly really enjoyed their reactions.

“Wow, Dale!!!” Wendy gushed. “So hot!!”

“Yeah, really sexy!!!” Crystal let out another small squeal. “Now I’ll do you, but this time I want you to lie down on the floor for me.” She explained. That seemed reasonable enough to me, so I did just that. “Now open your legs wide.” She told me, and when I did, she came and sat down in between, folding her legs Indian style and scooting as close as she could get to my bare, exposed privates in front of her.

“There we go…” She smiled, pulling out the bottle of lotion. “I think you’re going to like this.” She squirted some out onto her hand, and started lubing me up. “I saw a video about penis massages on the internet. They didn’t show anything, but they gave great tips on how a girl can massage a boy’s penis until he is going nuts. I really want to try it. Is that ok with you, Dale?”

Her eyes had this adorable pleading look to them. “Umm, yeah, that’s alright with me I guess, Crystal…” I had to swallow a little, or I was going to choke on my saliva. Now the touching began, but she wasn’t stroking me to get off. This time she was just using the tips of her fingers to lightly rub up and down my shaft, slowly circling it as she went. It felt so good!!! “Mmmmmm…”

That satisfied little smile was back on her lips. “Oh yes, Dale. You just enjoy it. You deserve it for being so good looking…” She swirled her lotion covered index finger around my glans a few times, before she went back to lightly teasing my shaft. I was twitching like mad!! “My, my, my… You’re so sensitive in this spot, aren’t you?” She circled her finger a few times on the spot where the head met the shaft on the bottom side.

“Fuuuuu…” I was having a hard time holding still. “Crystal…. I don’t… know how long I can take this…” Now she was just lightly stroking my ball sack, while I just desperately wanted her to jerk me off!! “Please…! Please…!”

“Please, what?” She giggled, still not giving me what I desired. “What do you want, Dale? You’ll have to speak up. I’m not sure what you mean.” She was rubbing the palms of her hands all around my shaft now, but was specifically avoiding the head.

“Please, Crystal!! I need to cum so bad!!!” Now I was just begging her.

“Oh I know…” She said, looking smug. “But maybe it would be a better lesson for you if I don’t let you cum? Hummmm? What if I just stop now, and leave you naked and twitching on the floor for the rest of the afternoon?”

“Please, no, Crystal…” I pleaded.

“What is in it for me if I allow you to cum?” She asked, lightly dragging her fingernail over my perineum.

"Please Crystal!"

"How about you stay naked for me for an hour?" She looked me in the eye, letting me see that mischievous smile of hers.

At this point I would do practically anything to get off, so I began to furiously nod my head. "Yes! Ok! Ok! I will!! Just do it now! Please!?!"

Crystal was absolutely delighted to hear that, and took my erect cock with both her hands. Then slowly, and ever so deliciously, she slid her hands up and down my slippery shaft. The pleasure was so overwhelming I couldn't keep my eyes open, and moaned so loudly, I was sure the neighbors must have heard me. "OH GOD, CRYSTAL!! OH MY GOD!! YES!! YES!! YES!! YOU'RE SO GOOD!!" I lost all control of myself, and started humping her hands! "OH FUCK YES!!! OH CRYSTAL!!! FUCK!!! OH GOD, FUCK!!!!! AHHHHH!!!!!" Jet after jet fired out of my cock with such force neither she nor I was prepared for it. I just kept twitching and writhing as she kept pumping and pumping me until I was dry!

I think I passed out again.

When I looked at her, she was just staring at me with open mouth shock. She was completely coated in my cum too! She must have moved a little closer when she started jerking me off, because somehow, every bit of my cum had ended up on her. "Hahahahaha!!!" She started laughing, but I could tell she wasn't laughing at me. It was pure joy that was the cause of her laughter. "Oh my god, Dale!! That was so much!!" Suddenly she moved to lie on the floor, almost curling up next to me, and she placed her top hand on my shoulder. "That was so amazing!!" She gushed.

"Uhh, thank you!" I blushed at her, partly because she was so close to me now. "I've never felt anything like that!"

"Aww, you're welcome!" She gave a toothy grin. "And now you have to stay naked for one hour!" She reminded me.

"Just why do you want that so badly?"

"Because you're so cute when you're naked." She answered. "And I don't just mean how hot you look, which you totally are by the way! But it's so adorable how you seem to be so shy when you're naked in front of me too." I couldn't help blushing at her. "See, just like that!" She pointed, giggling at my shyness.

True to my word, I stayed naked for her for the next hour. We moved over to the couch, where she sat very close to me, after she had gone to clean herself up of course. She made sure her bare thigh was up against mine the entire time. She'd also reach out to hold my penis every once in a while, always getting a slight rise out of me, but not making me fully erect. Throughout that time, we talked like old friends. Besides her touching, she never brought up my nudity, and after a while I was once again in that head space of being comfortable being naked in front of her. I even started to enjoy it again. I was really leaning, I loved to make her giggle even more than I already thought.

It wasn't until Wendy and John came into the room that I realized the girl had disappeared some time while Crystal had been jerking me. John was dressed, and walked Wendy over to the door. They gave each other a lovey-dovey look, before she said goodbye and headed home. After that, John came over and chuckled at me, "What are you doing, dude? You really like being naked in front of my little sister? You know you don't have to do everything she says, right?"

"Johnny!" Crystal complained. "Leave Dale alone. If he wants to be naked in front of me, let him."

My hour was already up a while ago. "I think it's time for me to get dressed anyway, Crystal."

"Awwwwe… Alright." She looked at me with sad eyes, but gave me a quick little kiss on the cheek. "I'll see you later though." She winked, then headed off to do her own thing, leaving me with my best friend.

John and I headed for his room after that, where I finally had the chance to get dressed. "What happened with Wendy?" I asked him.

"She came into the bathroom while I was in the shower." He gave me a grin, his quite toothy. It reminded me of the toothy grin Crystal had given me earlier. "I didn't hear her at first. She pulled the curtain open suddenly, and asked me if I would like help washing my back. I spun around to face her. It turns out Wendy’s kinda a freak! All she was wearing was this tiny black thong!!"

"No way! She was?!?" I was astonished. "Wait, you saw her boobs!?!?!"

"That's not all I saw! But I'm getting ahead of myself." He was totally elated. “She took my body wash, and started soaping up my chest. Then her hands went lower, and she was stroking me again! I came so hard… All over her!!!” He laughed.

“Then what happened!?!?”

“Well, she needed some help cleaning up…” He gave me a cocky smirk. “I told her to take off her panties, and join me. Both of us in the shower… Together!”

“Oh fuck!”

“I better not say much more. You know, Wendy’s so shy and all. But I’ll just say this… I got to wash every little bit of her sexy naked body!!”

“Oh my god!!!” I was in another horny daze after hearing that from John. I really wanted to know more, but at that point John’s phone pinged.

“Hey, it’s my mom. She’s back with the groceries. She wants our help bringing them in.” John explained, and we headed downstairs. Our discussion would have to wait.
Lola
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Re: My Best Friend's Stroker (Chapter 3 - Aug 9)

Post by Lola »

Yhea! This story is getting better and better. I love how the mom doesn't mind but helps the girls! And how Crystal convinced Dale to stay naked ahaha
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