William Finds Love Pt. 03

"Two Margaritas ma'am?"

"Oh yes, thank you, thank you," Amanda said as she leaned forward on the lounge chair taking the drinks from the handsome cabana attendant.

"Don't drink them too fast now," he said with a wink.

"My friend's in the restroom!" Amanda said. "I promise they're not both mine!"

"Suuure," he said jokingly as he walked away. Amanda smiled while admiring the view when he walked away. She placed one drink on the table between her and Jenn's chair and took a sip from the other.

She leaned back and crossed her legs. She was getting some great sun today and was hoping to darken her already impressive tan.

"That was fast!" Jenn said as she returned to her chair and sat down. She took a sip of her Margherita before removing her cover-up. She wore a red bikini, tightly clinging to her impeccably toned body. Like Amanda, she crossed her legs and looked around the large pool deck.

"Who needs a Country Club membership when we have your parents'?" Amanda said as she smiled cheerfully. The two friends frequently used the Country Club pool since Jenn's parents were long-time members.

"Gotta love it," Jenn said as they clinked glasses. A group of boys hanging out in the pool were doing a terrible job of hiding their consistent glances towards the women. Jenn didn't hesitate to wave to them, quickly revealing the fact that they were caught. They turned away in embarrassment.

"Your fan club?" Amanda asked.

Jenn turned to her. "More like your boobs' fan club."

Amanda laughed. "You think?" She adjusted her black bikini top by holstering her heavy orbs with the straps. Jenn marveled at the sight. "You're very blessed, honey."

"Oh why thank you!" Amanda said.

"I'm serious! You have the best tits. I can only dream of having those!"

"Stop. You know you're a hottie too, missy," Amanda said. She was right. Jenn had a great body, cute face, and beautiful full brown hair. Despite her modest chest, she never had issues garnering attention from boys.

"Ok, I'm dying with anticipation," Jenn said, angling her body towards Amanda to give her full, undivided attention.

Amanda smiled. "Ok, ok. So.." she started. "It's about a boy."

"I knew it!" Jenn said proudly. "Another Amanda fling. Is it Ronald? Or Jamie? I know you were crushing on him earlier this year."

"No, no, no, nothing like that," Amanda said, again adjusting her bikini strap. She then took another sip.

"What do you mean?" Jenn was stumped.

"You know how you have an affinity for... you know... a certain kind of man?"

Jenn laughed. "You can say it, you know. I like big penises. This is fact." They each laughed.

"Yes, big penises. Well, I sort of have an idea here."

"Are you going to set me up with a porn star? Because I really don't want to be with a porn star, Amanda," Jenn said, chuckling.

"You know my friend, William?"

Jenn scoffed.

"Right, of course you do," said Amanda. She was unexpectedly nervous as she brought up the subject. "I've been helping William out. With, like... online dating and stuff. Helping him make a profile, chat with girls, that kind of thing."

"Look at you, Miss Matchmaker! How's the poor boy doing? I've always felt so bad for him. But he's just so freaking shy and awkward sometimes. Poor guy."

"That's the thing. So we made a profile and everything, but he got no hits. So... I suggested maybe getting a little racier, ya know? Share some data points about himself."

Jenn burst out laughing. "You told him to put his dick size in the profile?! Amanda! Are you trying to destroy the last shred of self-confidence the poor boy has!?"

Amanda was not laughing. She lowered her sunglasses. "It's huge."

Jenn suddenly stopped laughing. Her mouth dropped. "No. No way. How huge?"

Amanda grinned as she looked around the pool. She took a sip of her drink and leaned in closer to Jenn. "It's nine inches. I've seen it. I jerked him off too."

Jenn nearly spit out her drink while Amanda giggled like a school girl. It was exactly the reaction she anticipated from her long time friend and casual hook-up. Not to mention, lover of larger dicks.

"You're kidding me!" Jenn said so loudly that the group of boys all looked over. She made a "turn around" motion with her finger as each of them obediently looked away.

"I swear to you. It was so big. Absolutely enormous. Bigger than any guy I've ever been with."

"And you jerked him off?!" Jenn was still stunned. "Why? How? I have so many questions!"

"I helped him shoot a video because someone on the App asked for it. So I filmed him while he..." Amanda trailed off.

"Choked the chicken?" Jenn asked.

"Mmm hmm. So afterwards, he was still obviously very hard. He actually looked very uncomfortable. So I said just take it out then. Let the thing breathe. So... one thing led to another and I gave him a hand... or two... or maybe three."

Jenn couldn't stop from laughing again. She was all smiles since the conversation started. "You are wicked! I love it!"

They each took a sip before Jenn continued. "So wait a minute. Why are you telling me this? What do I have to do with it?"

Amanda changed to a serious expression. "Jenn, the poor kid is so nervous to meet his first match from the App. She's very pretty too. And she's not shy about saying she wants to see his dick."

"She's probably a dude," Jenn said.

"That's what William said! Well, regardless. He is so painfully nervous. I told him I'd help him get ready for it. I told him I'd give him some practice."

"You're gonna fuck him? Aren't you two like siblings?" Jenn asked, unsure where it was going.

Amanda stared into her eyes. The two girls had been friends for so long but had explored each other beyond that on several occasions. Every once in a while, during these deep-level conversations the two of them reminded each other that they do in fact have a sexual connection. It was never something they outwardly talked about, but it was always there. "That's where you come in," she finally said with a smile.

-----------------------------------

"Company? What do you mean, company?" William asked as he tried to keep his voice down. He was talking to Amanda on the phone in the office of the pharmacy.

"You know her, William. It's Jenn. She's gonna swing by with me tonight. Is that ok?"

"I mean, I guess so. Sure, but... why? I thought we were gonna play Scrabble?" he asked.

"We can still play. Or not. Let's just hang out, it'll be fun, the three of us."

"Whatever," William said. "Look, I gotta go. My break's over." He hung up the phone and returned to his cash register. He was more than disappointed that Amanda wanted to bring a friend over. It would be the first time he saw her since the handjob incident. He was hoping they could play around again, maybe another handjob, maybe more. He even thought he'd get to see Amanda's boobs perhaps.

But now, those hopes and dreams were shattered. There would be no way any of that could happen now that she was bringing her friend. William convinced himself that she was bringing her on purpose. She needed an excuse to not have to hook up with him again. She was probably disgusted by him and didn't have the heart to tell him.

Reluctantly, William dragged himself to the liquor store and supermarket to get some things for that evening. He rarely had guests other than Amanda. He bought a few bottles of wine, some beer, chips, and snacks before heading home.

It was eight o'clock when he heard the door unlock and some female chatter on the other side.

"You have a key?" a voice asked. It was Jenn. "I practically live here," Amanda responded as they each emerged from the doorway. William stood up from the couch and wiped his sweaty palms on his jeans.

"Nice look!" Amanda said as she hugged him. "Did someone help you pick these clothes out?" she winked.

"Hi William," Jenn said as she extended her hand. "You remember me?" she asked.

"Of course," William said. He met her only a handful of times and normally at a crowded party that Amanda dragged him to.

"Nice place," Jenn said, looking around. "I actually thought this complex was a senior living thing."

"Jenn!" Amanda said as she laughed. "Not nice!"

"Kidding of course," she said, turning to William. "William, your apartment is lovely."

"Thanks," he said. "So... umm... can I get you guys a drink? Or..."

"Do you have any wine?" Jenn asked as she surveyed the kitchen where two wine bottles were sitting on the counter. "I'll have that please."

"Same. Thanks William," Amanda said.

The three of them sat in the living room, sipping drinks. Amanda and Jenn did most of the talking as they laughed and joked about all sorts of topics William knew nothing about. He sat quietly, sipping his beer and half listening to the conversation. He was more interested in trying to sneak peeks at both girls. Amanda looked beautiful as always, wearing tight dark jeans and a black top. Her shining blonde hair was full and draped over her shoulders, reaching her bust line. The low cut of her shirt showed off ample cleavage.

Jenn wore a tight white top, black spandex pants with heels. She was incredibly sexy and apparently knew it with her choice of clothing. Her hair was a dark brown and the way she wore it in a ponytail. Their perfume wafted through the small living room. It was driving William crazy. He loved it.

"William?" Amanda asked.

"Hmm?"

She laughed. "Jenn just asked you what you do for work."

"Oh... umm... sorry about that. I, um... I work at Bernard's," he said softly.

"The pharmacy?" she asked. "I get my birth control there," she said.

""He doesn't just work there," Amanda said. She turned to William. "He's the Manager."

"Oooo, the Manager, huh?" Jenn said. William couldn't tell if she was being sarcastic. He decided she probably was. "Very nice," she added.

"Yup," William said awkwardly. "I still work the register sometimes though--"

"William, why don't we put on some music? It's a little quiet in here," Amanda said, interrupting his bland commentary. She then stood up and walked over to the Bluetooth speaker. William turned to Jenn who was smiling at him as she took a sip of wine. He tried to smile back, but was so nervous it probably came across weird.

Amanda played some music before sitting down again. "So," she said looking at Jenn.

Jenn nodded. "So," she repeated. "Amanda tells me you are doing some online dating?"

"You told her that?" William turned to Amanda with shock in his eyes.

"Relax, it's cool," she said. "Jenn's gonna help us out."

"Us?" William was confused.

"Look.. Bill, Billy, can I call you Billy?" Jenn asked.

"William's good," he said grumpily.

"William," Jenn sat forward and folded her hands together. "Amanda told me about how you have a date coming up. And how that date may be interested in you in some unique ways."

Is this going where I think it's going? William thought to himself.

"What I'm saying is... I heard you have a gloriously magnificent penis," Jenn finally said.

Holy shit. It is going where I think it's going.

Amanda and Jenn started laughing at her directness. Amanda quickly regained seriousness. "William," she pleaded. "Please don't be upset. I told her this. But I told her for a good reason."

"She's right," Jenn said. "I love big dicks."

Amanda laughed again. "This is true, but that's not why." She turned to William. "William. Jenn's gonna help you with the sex part of all this."

William's heart skipped a beat. His palms grew sweatier. Butterflies filled his stomach. And, of course, his cock twitched. "She... she is?" he asked.

Amanda nodded. "You said you were worried about how you would perform and everything. And seeing as I can't help you, I figured we could ask Jenn to step in."

Jenn raised her hand as if she was in a classroom. "That's me!" she said excitedly.

William was shocked. He wondered what they had in mind. He also wondered what Amanda meant by saying she was unable to help him. Was this the end of any hopes he had for romance between them? He shifted his focus to Jenn. She was gorgeous. Remarkably attractive and utterly out of his league. "What are you saying?" he asked, nervously.

"I love big dicks. I can show you how to work it. We can have sex, William. That is... if you're interested in having sex with me."

Amanda eagerly awaited his reaction. She wanted nothing more than for her friend to be happy. "What do you think?" Amanda asked.

William leaned forward and folded his arms on his lap. He was getting hard and didn't want to show it. "I dunno about this," he said. "I've never... you know..."

"Oh believe me I know all about it," said Jenn. "And you can trust me it's going to be just fine. I promise."

William paused for a long time as he considered the offer. On the one hand, Jenn was an incredibly sexy girl practically begging to have sex with him. But on the other hand, it was Amanda he had hoped for and he couldn't help but feel severely disappointed.

"I dunno," he said again.

"Look," Amanda said. "Why don't you think about it? In the meantime, take it out and let him breathe a bit. Let's show Jenn what we've been talking about."

William took a deep breath. "Umm... ok. I guess that's fine."

"Yay!" Jenn said as she clapped her hands. "I can't wait!"

William reached for his belt as the girls eagerly watched. It was already clear he was sporting an erection as he moved his arms away for the first time. He stood up and slid his jeans to the floor, revealing a massive tent forming under his boxer briefs on one side.

"Damn," said Jenn. She looked at Amanda who excitedly nodded in agreement.

"Here we go," said William as he pulled his underwear down, freeing his massive flesh-toned cock. It sprung up lewdly before bouncing a few times protruding from his body. His oversized balls sagged prominently beneath it.

"Jesus Christ," said Jenn. She was no longer jokes and smiles and now seemed possessed by the massive appendage before her. "That's the biggest penis I've ever seen."

"I told you!" Amanda said. "Isn't it special?"

Jenn kept staring. "It's more than special. That thing... that's like a work of art." She looked up and made eye contact with William. "You have quite the gift there, William."

"Heh... umm, thanks," he said. He never quite knew how to respond to compliments of his dick.

"William, come sit over here. Would you please?" Amanda asked as she patted the section of the couch between her and Jenn. William kicked his jeans and underwear aside as he strolled over. Each of them watched his cock bounce and sway as he approached. He sat down between them and leaned back on the couch. His cock was so big, it rested across his abdomen.

"When did you find out you had such a big dick?" Jenn asked, eyes still glued to it.

No one had ever asked William that. He had to think about it. "I'm not really sure. I guess I never really knew until..."

"Me?" Amanda asked.

William nodded. "Right."

"It's probably bigger than 99% of guys, William," Jenn said. "Believe me I like to think of myself as a penis aficionado."

Everyone, including William, laughed at that. "Oh do you now?" Amanda asked. "I had no idea!"

William remained quiet as the girls stared at his penis and talked about it. The more he exposed himself, the more comfortable he was. This was the third time he had been naked in front of Amanda and now someone else too. He admitted to himself he was actually enjoying the attention.

"It looks so hard. You're like a rock solid column right now, huh?" Jenn asked. "Can I see how it feels?"

William couldn't dare deny the request. "You can," he obliged.

In no time, Jenn's hand was around the base of his cock. Squeezing, stroking, gauging its sheer size. "This is incredible," she said. "You're so big."

"His balls too," said Amanda as each of them peered forward to see. "They're enormous."

"They look like they're pretty full, huh?" Jenn said. By now, she was openly stroking the lower portion of his shaft. William was too scared to agree with her comment out loud, but it was true. He was getting hornier and hornier by the minute.

Amanda seemed to sense this as she interjected. "Can you stop for a second? I just want to admire it." Jenn removed her hand as the girls stared at his throbbing hard cock. "It's so perfectly proportioned. I wish I could mold your cock into a dildo or something!" Jenn suggested.

"Look at his veins. I think I like those the best. Look at how they throb!" Amanda exclaimed, getting into the verbal praise game with Jenn.

"So pretty," said Jenn. "Hey, you know what? Can you do me a favor?" she asked.

"What?" William responded.

"Can you go refill our wine glasses with your dick out? I saw that in a porn one time and it was super kinky. The waiter was completely naked and the girls were clothed. His cock just bounced around as he served them drinks." Jenn giggled with excitement.

"You... I mean, girls... watch porn?" William asked.

"Duh!" Jenn said. "Everyone watches porn, silly! So, can you do it? Pretty please?"

William stood up and turned so his cock was at eye level. Jenn and Amanda's eyes never seemed to unstick from his penis. Starting to feel more comfortable, he wagged his hips a little, resulting in his cock swaying back and forth. The girls burst out in uncontrollable laughter. Jenn even clapped. "Woooo hoooo! Go William!"

He then headed for the kitchen to fetch some refills for the girls. Jenn leaned in closer to Amanda. "It's so fucking huge!" she whispered.

"I told you! You should see how many girls wrote back to him on the App. They all want to see it!"

"I wanna fuck him. I seriously need to fuck him, Amanda!"

Amanda laughed. "Let's take our time. He's obviously very nervous."

"Here we go," said William as he approached the girls. As expected, they each eyed his big cock, bouncing left to right as he walked.

"This is amazing," Jenn said as she retrieved her glass of wine. "I don't even care that the wine is terrible."

"Wait, really?" William asked.

"Yes," Amanda chimed in. "But it's ok, William. It's the thought that counts."

"And the cock," said Jenn as they each laughed. William reclaimed his spot between them as he took a sip of the beer he brought for himself. Jenn quickly grabbed his cock again and began to stroke. William barely had a sip before he was in immense pleasure again. "Ohhh fuck," he said out loud, making his feelings known.

"It's so hard in my hand. I think I'm in love with your penis, William. Is that ok? That I'm in love with your penis?"

"Sure," said William. "Sure, why not?"

As Jenn stroked him, it became clear there was a substantial amount of precum dripping out the tip. "You look so aroused right now," she said. "Are you pre-cumming a little up there?" she said with a wink.

William looked visibly distraught. As Jenn jerked him off, his arousal rapidly accelerated. It had been no more than five minutes of direct contact, yet here he was again, desperately trying to stave off an explosion.

"Wait, wait, can you... umm... can we stop a second?" he asked as he grabbed Jenn's wrist.

"Oh, I should have mentioned," Amanda said. "William may need to release first. Before we move on to the main event."

"Really? Are you that turned on?" Jenn asked, eagerly.

William didn't even mind Amanda speaking for him. He was happy she said what she did, otherwise he may risk being embarrassed soon. "Yeah, I tend to go quick," he admitted.

"Just the first time, right William? Just so he can last when you guys have sex."

Jenn looked around the room. "I think we may need to make it a little wetter."

"You mean, like, lube?" William asked.

"Umm... I have a better idea," Jenn said. Amanda grinned ear to ear watching Jenn crouch to her knees in front of William. She then grabbed his cock by the base and angled it towards her mouth, stopping just short and looking up at him. "Is this ok?" she asked sexily. William bit his lip and nodded.