Jenny’s Tutelage

In 5 parts, based on a post by BrazenHorse. Listen to the ► Podcast at Connected.

"Here

we go," said Willy 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.

“Uh, ladies, my eyes are up here?” Willy cut the tension with glee.

 "And your point would be? Jenn retorted with a horny grin. “Idon't even care that the wine is terrible."

"Wait, really?" Willy asked.

"Yes," Mandy chimed in. "But it's okay, Willy. It's the thought that counts, that and the alcohol effect."

"And

the cock," said Jenn as they each laughed. Willy 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. Willy barely had a

sip before he was in immense pleasure again. "Oh fuck," he said out

loud, making his feelings known.

"It's so hard in my hand. I think I'm in love with your cock, Willy. Is that okay? That I'm in love with your cock?"

"Sure," said Willy. "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.

Willy

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," Mandy said. "Willy may need to release first. Before we move on to the main event."

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

Willy

didn't even mind Mandy 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 Willy? Just so he can last when you guys have

sex." Mandy clarified. “And Willy, coming quickly and often, are proof

of high virility. Be proud of your volume and multiple servings.”

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

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

"Umm,

I have a better idea," Jenn said. Mandy grinned ear to ear watching

Jenn crouch to her knees in front of Willy. She then grabbed his cock by

the base and angled it towards her mouth, stopping just short and

looking up at him. "Is this okay?" she asked sexily. Willy bit his lip

and nodded.

"Good,"

she whispered before opening her mouth wide and stuffing his cockhead

inside. She closed her eyes and sucked the tip while stroking with her

hand. Mandy smiled, watching Willy's facial expression. He was in pure

ecstasy. "That feel good?" she asked him. He closed his eyes and nodded.

"Umm,

hum" Jenn moaned as she sucked his cock. Her mouth was full as the

first few inches of his shaft was buried down her throat. Her hand raced

up and down his cock while her other hand cradled his balls.

She finally took a break, panting out of breath. "Oh my gosh, Willy. You're so fucking big! I can barely do this!"

"You're doing great. Right Willy?" Mandy asked.

"Definitely," he muttered. He could barely find words. "Please keep doing that."

Jenn eagerly continued, this time sucking and slurping with passion. She was determined to get him to cum.

"Oh,

oh God," Willy said. He sounded like he was in agony, but the truth was

the complete opposite. His very first blowjob was better than he ever

imagined.

"She's

so good, huh?" Mandy asked. Willy could only look in her direction, but

couldn't respond. She unexpectedly grabbed his hand and brought it

towards her chest. At first, Willy held back, unsure what she was doing.

But it became evident quickly she was inviting him to fondle her. Willy

hesitantly grabbed her breast and held on tightly. He didn't know what

to do. The most beautiful breasts he had ever seen, ones that he

fantasized about repeatedly for years, were now in his hands. And they

were even more glorious than he ever imagined.

"Do

you like that?" Mandy asked. This caught Jenn's attention as she opened

her eyes and looked up while continuing to suck his cock.

"Yes," Willy said. "So much."

Jenn and Mandy made eye contact and smiled at each other, happy with the result they were getting from Willy.

""Oh

God. Oh my God, oh shit here it comes!" Willy said as he let go of

Mandy and clutched the couch cushions for dear life. It was time.

Jenn

stopped stroking, but kept her lips wrapped firmly around his shaft.

She was prepared and ready. She rubbed her tongue firmly on the

underside of Willy’s tip, as she looked up at Willy in anticipation.

Mandy focused on the exposed part of his shaft. Willy moaned as it began to throb powerfully. He was ejaculating.

Jenn's

eyes immediately got wide as she felt the first gushing load of hot cum

spray the depths of her throat. It was far more than she imagined.

After the second blast, she knew it was too much to take in, so she

immediately released him and stroked his cock with her hand.

"Jesus!"

she said after swallowing fast and inhaling a quick breath. Cum dripped

out her mouth, down her chin, and rolled into her cleavage below.

"Ah!"

Willy belted out. He was just getting started. A long, unbroken rope of

cum flew up in the air, landing back down on his chest with a splat.

Mandy covered her mouth as she sat speechless, watching him cum.

"Willy! You're still going!" Jenn said in shock, as she held her hand around the glans.

"Oh

God, Jenn! Please don't stop! Oh fuck!" he said as more and more cum

blasts shot out the tip, leaving him drenched in his own seed.

"Is this real?" Jenn asked, looking over to Mandy for answers. She could only laugh in response. "It most certainly is."

Both

girls watched as the final few cum blasts exited his cock, dripping

harmlessly down his rigid shaft; coating Jenn’s attached fist. No one

spoke as all three of them stared at the mess left behind. Only Willy's

labored panting could be heard.

"I have," Jenn swallowed to clear her throat, "Never, and I mean never seen anything like that in my life."

Willy and Mandy looked at each other and laughed. Both were very happy with Jenn's reaction.

"Right!?!" Mandy said.

Jenn

finally looked down and noticed a considerable amount of cum had landed

on her shirt. "Well, there goes this shirt," she joked. She crossed her

arms at the bottom of her shirt and began to lift it, but paused. "You

don't mind, right?"

Willy shook his head. "Not at all."

"Good,"

she smiled before lifting her shirt up over her head revealing her

perfectly flat belly and medium, perky boobs. She wore a black bra. "How

did you get it under here!" she exclaimed. All three of them looked

down to see a thick glob of cum on her bra. It must have seeped through

the shirt. "Welp, the bra too I guess," Jenn said as she unhitched her

bra and let her breasts free.

"Yay!" Mandy said, clapping. "Boobies!" she said in a high-pitched voice.

Jenn cupped her tits and held them up. "They're iddy biddy, but I like 'em."

"Oh my gosh, stop. They're perfect," said Mandy. "Right, Willy?"

Jenn eyed his still pulsing hard cock. "I guess that's a yes!"

Willy blushed. "Yes. I like them a lot."

"So does he!" Mandy pointed to his cock. "Did you even go soft?"

Willy shook his head. "No. Not really."

"Where

can I get one of you? Can you come home with me?" Jenn asked. "You're

something else, buddy. I can't wait to get on that thing."

Willy

didn't try to hide the fact that he was openly staring at Jenn's

breasts as he mindlessly stroked his cock. Her nipples were small and

pink, but seemed to fit the rest of her physique perfectly. She gave him

an unobstructed view of them as she re-secured her ponytail with both

hands. She smiled while watching him stare at her.

"Willy?" she asked as he finally broke his stare and looked up.

"Shall we go in your room?" Jenn asked in a sweet and sincere tone. Willy nervously bobbed his up and down.

"Okay,"

she whispered before standing up and extending her hand. Willy took it

and they each stood up. He turned back to Mandy. "You coming?"

"Oh, umm, did you want me to, Willy?"

"Well, yeah. I thought, yeah I do. Jenn?" he asked.

"More the merrier!" Jenn answered.

With

that, the three of them headed towards his bedroom. Willy walked behind

Jenn. His cock was so big and hard it kept poking her in the ass.

Actually, Jenn deliberately slowed down just to facilitate the contact.

The girls were overly amused by this, laughing hysterically at the ridiculous sight.

"So,

first things first. There are lots of positions we can do," Jenn said

as she took charge. She and Willy were each on their knees on the bed,

facing one another. Mandy sat on the corner of the bed as well, facing

them as a spectator.

"But

I'm gonna be honest with you," Jenn continued, looking down at Willy's

hard cock. She took it in her hand. "You may be too big for a lot of

them, at first."

"Agreed," Mandy said as she looked at his cock and nodded. "100% agree."

"Why don't we start with me on my back and you in front. Called missionary."

"I know what missionary is," Willy grumbled as they got into position.

"Just

trying to be specific!" Jenn said as she licked her hand and grabbed

the head of his cock. "Let's get you nice and lubed here, shall we?"

Jenn

rubbed her saliva, mixed with Willy's precum up and down the upper

section of his shaft. The glisten from the moisture left his sturdy cock

looking shiny and prominent in the dimly lit bedroom. Mandy was

mesmerized by the sight and from what was about to happen. As she

lovingly watched them prepare, she felt an intense burning sensation

between her legs. She wanted so badly to masturbate, but was fearful it

would ruin the moment. Willy was about to lose his virginity to her best

friend. It was a magical moment and she was happy to be there, yet felt

an uncomfortable feeling that maybe she shouldn't be there, or maybe it

should be her instead.

"You ready, Willy?" Jenn's question snapped Mandy out of her deep thoughts.

"I think so," said Willy. "I mean, yes. Yes I'm ready baby."

Jenn and Mandy burst out laughing. "What?" asked Willy.

"Nothing. It's cute," said Mandy. "Go ahead, Willy."

Jenn

shimmied out of her panties, revealing her cunt for Willy to feast his

eyes on. He had never seen a cunt in real life. At first glance, he

decided it was more beautiful than anything he could have ever imagined.

She maintained a small light brown bush, trimmed impeccably. Her labia,

pink and moist, opened slightly to reveal a dripping wet snatch better

than anything Willy had seen online. She smiled as he stared, reaching

down and opening it for him with her fingers. He gulped.

"Just

put it in nice and slow, okay Willy? You always have to remember how

big you are and you may hurt girls if you go too fast."

If

Willy wasn't clutching his cock, they would see how much his hands were

shaking. He slowly inched forward. "Okay," he said with a stammer.

"Okay, alright."

"Take your time," Mandy whispered, carefully rubbing his thigh.

He

leaned forward. His cock head was so big against her crotch, it

appeared as if there was no way it was going to go inside anything.

"Um," he said.

"It's okay," Jenn said. "We’re in no hurry."

After

a surprisingly short amount of time, Jenn changed plans and 

repositioned both her legs inside Willy’s knees. She pulled his chest

down onto her tits and her thighs clamped Willy’s cock firmly against

her clit and swollen wet cunt lips. “Let’s just enjoy the massive girth

and give my clitty a nice massage, while my cunt dilates some more.” She

dropped her head back, onto the mattress, and let out a moan. "Wow,"

she said. "You're fucking huge."

"Is it okay?" Willy asked, concerned.

"Yes. Oh yes, honey. Keep working it in. This feels amazing."

Willy

resumed as he tried to slide more of his cock. Through enn’s hot

crotch. It was far tighter and far warmer than he had ever imagined, but

he loved every second of it. He made eye contact with Mandy who looked

up proudly and mouthed the words "Congratulations." Willy smiled back.

"Oh

God. Oh that's good, Willy. My God, that's good," said Jenn with her

eyes closed and head rested on the mattress. "This feels so good right

now."

"It does for me too," said Willy. "Like, a lot."

Jenn

propped up pillows under her shoulders, so she could see better. "I

seriously cannot believe you're getting it in there. You're so thick and

full. I feel like I've died and gone to heaven!"

"Try thrusting faster now, Willy," said Mandy.

One

thing Willy had always been good at is following directions. He started

to rock back and forth in an attempt to bring Jenn to an orgasm. "Like

that?" he asked.

Jenn

bit her lower lip and nodded. "It feels really good," she whispered.

She was starting to become flush. Satisfied he was doing fine, Willy

continued thrusting. His cock was now sliding in and out of her sopping

wet crotch with ease. "Oh God," Jenn said as she closed her eyes and

collapsed onto the bed sheets. "Your cock is so good."

As

Willy began to get the hang of it and worked his way deeper and deeper,

Mandy started to feel a bit left out. In the beginning, it was all fun

and casual. But now Willy was legitimately ‘outercourse’ crotch-fucking

her best friend and there wasn't much for her to do anymore. She found

herself hopelessly staring at his thick cock as it glided in and out,

coated in her friend's ample natural wetness. The shine and glimmer of

this throbbing, veiny cock was enough to send her mind in all sorts of

naughty directions.

"Does it feel good?" Willy asked as he paused for a moment with his cock buried halfway.

Jenn propped herself up on her elbows with her eyes wide. "Don't stop! I was gonna cum!"

"Oh, sorry!" Willy exclaimed as he promptly continued. Jenn's eyes rolled in the back of her head as she began to moan loudly.

"Umm God! Fuck yes! I love this cock!" she said. "You're gonna make me cum like this!"

It

was not more than a few minutes until Jenn finally reached orgasm. She

grasped the bed sheets tightly as her mouth formed a perfect circle.

"Fuck, fuck, fuck, fuck, fuck!" she shouted lewdly. "I'm cumming!"

Willy

was completely shocked and overwhelmed. He had never imagined he would

be bringing a woman to orgasm simply by having crotch sex. From

everything he read, he figured it'd be nearly impossible to ever

accomplish this. All he could focus on was to continue fucking her while

holding off his own orgasm with all his might. He looked down onto

Jenns perky nipple and decided to nibble on it.

Suddenly,

Jenn screamed in ecstasy. After panting heavily for a minute, she slid

up, releasing Willy's cock from her thighs. She spun around on all

fours, raising her cute ass in the air. "Do me like this, Willy!" she

proclaimed.

"Like, in your ass?" Willy asked, clutching his cock, dumbfounded.

Jenn

sighed and reached between her legs, grabbing his cock and guiding it

to her snatch. "Like this," she said. "Oh, that's it right there. Umm,

God you're big." And just like that, Willy proceeded to seek entry into

her, doggy-style. Tonight would be a night full of firsts, he decided.

But Jenn’s tight snatch just wouldn’t open enough, so Willy resumed his

outercourse alternative.

Neither

of them noticed her leave. Right before Jenn had her first orgasm,

Mandy had snuck out the door and sat down on the couch in the other

room. She could do nothing but sit and listen as Willy lost his

virginity in spectacular fashion right next door.

At

first, she felt fine about everything. She was happy for Willy. Happy

for Jenn. She felt like she was doing a good deed giving him the

practice he needed before his big date. However, as she sat alone in the

other room listening to the sounds from the bedroom, she felt a sense

of jealousy. She had gotten to know Willy so well in the past couple

weeks that she may have grown a bit of an attraction to him. It

certainly wasn't just his impressive equipment, but seeing that side of

him really struck a chord with Mandy.

‘Was Willy saving himself for me?’ Mandy wondered.

Yet

here she was alone on his couch with her hand buried in her wet snatch

listening to her friend get the daylights fucked out of her by him in

the next room. As Mandy listened to the sounds, she masturbated

feverishly. She couldn't help herself. She was overcome with desire.

"Oh God, Willy. I'm cumming again. I'm cumming. Fuck, fuck!!"

Willy

was covered in sweat as he made love to her with passionate aggression.

He studied her intricate back muscles. Her round and bubbly ass rode up

and down his pole. Reached around and fondled both nipples for a while,

then massaged her ass cheeks.

‘I am the fucking man right now.’ Willy

thought to himself. He did it. He bedded a hot babe. He made a

beautiful girl have not one, but two powerful orgasms. Tonight couldn't

possibly be any better, except her cunt just wouldn’t accommodate his

girth, and she didn’t have the patience to go any slower.

Then

he felt it. It came on quickly, much quicker than he expected. One

slight move by Jenn sent him off the rails.  She had reached down and

cupped her fingers around his frenulum. His blood boiled and stomach

quivered. He was going to cum.

"Oh shit. Fuck," he said. "I'm gonna bust."

Jenn

quickly spun around. Like a pro, she immediately sat in front of Willy

on her knees, taking his big cock into her mouth. Willy's ass cheeks

clenched as he unloaded his long-building cum blast into the back of

Jenn's throat for the second time.

"Ah!"

Mandy could hear the deep moan from next door. It was followed by

several restrained grunts and giggling from Jenn. She closed her eyes

and imagined Willy blowing his substantial load all over Jenn's face.

She moved her fingers faster as her heart raced. She wanted to cum and

she wanted to do it at the same time as Willy.

"Fuck!" Willy said as Jenn continued to laugh.

"Umm,"

Mandy said quietly, ensuring she wouldn't be heard. Her cunt gushed and

throbbed as a warm and familiar sensation washed over her entire body.

Next

door, Jenn held her hands in the air as she stared at her breasts while

Willy coated them with his thick cum. She couldn't help but laugh at

the sheer volume while also being impressed at the young man's

abilities. "Holy shit!" she exclaimed.

"Oh

fuck," Willy said as he squeezed his cock at near the tip, releasing

one final drop of cum. "That was amazing," he said. His voice cracked as

if he was about to cry. He was overcome with emotion.

"Look

at that!" said Jenn as they both stared at her chest and abdomen. "I've

never seen that much come out!" She looked up at Willy with a smile.

"You're really something special, my friend."

"Thanks," he said.

Mandy

lay still, eyes closed, her chest rapidly rising and falling as she

recovered. She seemed to have had an orgasm at the same time as Willy,

although they were unaware. She quickly sat up, buckled her pants and

darted for the sink. While she washed her hands, the bedroom door swung

open.

Jenn

slowly emerged, walking bow-legged and giggling. "I think I'm gonna

need a few days to recover from that!" she said to Mandy as she slowly

and gingerly sat down on a chair.

"I told you!" Mandy said. "How was it?"

Jenn,

fully clothed, took a deep breath, closed her eyes, and rested her

hands on her stomach. "He's amazing," she said. "Where on Earth did you

find him?"

"Who

me?" Willy asked as he entered the living room. He stayed back to clean

up a bit. Both girls turned to see Willy strolling towards the couch,

completely naked. He even swung his cock around in a circle before

plopping down on the couch. He spread his legs apart and rested his

softened unit over the edge of the cushion.

"Wow, okay," said Mandy, shaking her head as she dried her hands. "Looks like someone had fun."

"This is the greatest night of my life," Willy said. "I still can't believe what just happened."

Mandy

returned to the living room and sat on the other end of the couch,

facing Willy. She smiled, mouth closed, somewhat hesitantly.

"Tell me that's the smallest you get," Jenn said, wasting no time bringing attention back to Willy's cock.

He

picked it up and dropped it down again. "This is the smallest I get,"

he proclaimed proudly. The hefty cock was still a good six inches in

length.

"Can you, like, drape it over your leg?" Jenn asked. "How would that work?"

Willy

placed his cock over his left thigh, as requested. It was so long, it

easily covered the surface area of his skinny leg. Jenn shook her head

in disbelief. Mandy remained quiet.

"How

on Earth?" Jenn said. She turned to Mandy. "It was amazing. Very good

for a first-timer, I might add. He did the trick." She turned to Willy.

"At least twice."

Willy

and Jenn spent the next few minutes recollecting their experience.

Mandy noticed a certain swagger and confidence in Willy she hadn't seen

before. It was almost as if having sex turned him into a new man. She

was still surprised he walked out completely naked. This was something

the old Willy would never do unless asked. Mandy assumed that Willy

fully penetrated Jenn.  Wendy felt empty and regretful. She knew now

that this should have been an intimate evening just for her and Willy.

Now she’ll never get the opportunity to be his first.

"Well, I should get going," said Jenn as she carefully stood up. "I need rest, and an ice pack."

Willy

stood up to hug her. As they embraced, Jenn kissed him on the cheek and

reached down to give his cock a squeeze. "If you ever want more

practice, well, you know where to find me, big guy."

Willy walked her to the door and shut it behind her. He turned around and leaned against it with a big smile on his face.

"I owe you," he said to Mandy. "I owe you so, so, much."

Mandy smiled. "I'm glad you enjoyed yourself."

Willy

walked over to the couch and sat down right next to Mandy so their legs

were touching. He had a look of desire on his face. "You know," he said

as he picked up his cock and squeezed it. "I think I could go a third

time. And I do owe you," he said with a wink.

Mandy eyed his cock and noticed it was growing hard. But she quickly turned away.

"What?" Willy asked, surprised his advances did not seem to be landing.

"I have to go," she said. "It's getting late."

Willy

was suddenly embarrassed and humiliated. In an instant, he felt like

the old Willy. As his cock shrunk, he covered it in shame. "I'm, I'm

sorry. I thought you, I thought I,"

Mandy stood up and faced him. "I'm glad you guys had fun. Now you should be fine for all your future dates, right?"

Willy paused. "Well, I guess so, yeah,"

"Great. Good luck with everything. I'll see you later."

Mandy

rushed out the door, leaving Willy naked and stunned on the couch. In

the sudden heavy silence of his apartment, he desperately tried to think

of what just went wrong. The girl he loved and adored seemed to be

turned completely off from him. He fought back tears as he retreated to

his room and collapsed in bed.

Alienation From Mandy

Several

days had passed. Willy grew more and more anxious as the week went on.

He couldn't concentrate at work or home. He was filled with a feeling of

dread. As if something had gone terribly wrong.

His

date with Donna was that evening. Despite losing his virginity and

learning all he could with Jenn and Mandy, he felt like he wasn't ready.

His usual lack of self-confidence haunted him, leading him feeling

unprepared and fearful.

Adding

to his misery, he hadn't spoken more than a few texts to Mandy since

she left his apartment. Willy was not naive. He knew he messed up. He

inappropriately made an advance on her after he had just had sex with

her best friend. In the moment, it felt right. He was flying high,

feeling like he could conquer the world.

But

in reality, it was a careless move. He could sense Mandy was completely

turned off and likely disgusted. How could Willy have thought he had a

chance? Even though he had the most amazing experience in his life that

night. Even though he lost his virginity to a beautiful brunette and

made her orgasm twice, he felt empty and lost. All he could think about

was Mandy. Being with her as she watched. Feeling her glorious breasts.

The look on her face when he first penetrated Jenn.

He felt miserable about where things stood now.

But

there was no time to dwell. He had to prepare for the moment this was

all about. His first date. Willy spent most of the day nervously pacing

around his apartment. He frequently opened the dating App to look at

Donna's pictures. He found her to be attractive. Blonde hair, blue eyes,

and a pretty face. Unfortunately, she never sent him more than a few

pictures and none of them showed her entire figure. One of them was of

her exposed breasts and they were clearly large with big pink nipples.

Since Willy was definitely a boob guy, he couldn't help but feel excited

to meet Donna.

After

reading advice online and factoring in Mandy's own assessment from the

other night, Willy decided it was best to masturbate on his own before

heading over to Donna's house. The last thing he wanted was to cum in

his pants like he did in front of Mandy.

So

that afternoon, he undressed and laid down on his bed. He opened up his

phone to look at the pictures of Donna's tits while playing with

himself. Before long, however, he switched over to Instagram and started

scrolling through Mandy's page.

She

had such a social, active lifestyle. Countless friends and dozens and

dozens of experiences were on full display as he scrolled through. He

often felt sad when watching her other life through the veil of social

media. He didn't have much of any experiences to speak of. He often

found himself focusing on her pictures from that previous summer when

she went to Cancun with her girlfriends. Her body was perfect in that

black bikini. He grew hard almost instantly as he stared at her breasts

and vividly remembered fondling them the other day.

He

set the phone aside to inspect his fully hard cock, dripping with

precum. He spread his legs and feverishly tugged at it, picturing Mandy

watching him have sex with Jenn. The experience was likely to live in

his mental imagery forever.

“Umm"

he grunted softly as his cum boiled. He angled his cock directly up in

the air so as not to splash his face. He became accustomed to his large

volume of ejaculate.

Thick

cum shot out into the air, splattering back down on his belly as he

moaned. While he came, he pictured Mandy right next to him laughing and

giggling.

"You cum so much!" he could hear her voice in his head.

After

the final few loads, he rested his head down and closed his eyes. A

sudden and unmistakable feeling of guilt and anxiety crept in. The

reality of the situation was back in the forefront of his cluttered

conscience. He was about to go on his first date.

Tinder Disaster

As

Willy drove past each house, they seemed to be getting bigger and

fancier. He had never been on this side of town his entire life. It was

the wealthy side; where all the 'somebodies' lived. He had no business

over here. Until tonight.

His

Google Maps let him know the address was at the end of the street. As

he pulled into the driveway in his 2009 Toyota Camry, he saw two

Mercedes parked next to what appeared to be a tennis court adjacent to

the house. The place was huge. He checked three or four times to be sure

he was even in the right place.

"Holy

shit," he said quietly to himself as he approached the large Mahogany

doors at the main entrance. His hand shook as he rang the doorbell. He

quickly put it behind his back as he waited for an answer.

After

what seemed like a painful eternity, the handle finally turned as the

door opened. Standing in the frame was a plump woman, no more than five

foot five, wearing a black dress and holding a glass of wine. "Willy,"

she said as she beckoned him in. "Do come in."

"Umm," Willy said, confused. "Is, umm, Donna here?"

"Who's that?" she asked.

Willy blushed with embarrassment. How could he have been so stupid to go to the wrong house?

"Relax.

It's me, silly. I'm Donna," she said as she held out her hand. Willy

tentatively shook it. He was still very confused. She looked nothing

like the photos. Firstly, she was much larger than he thought. Her face

was slightly wrinkled. Her eyes were not nearly as bright as the

pictures led him to believe.

"You're

skinny," she said as she led him into the large, bright kitchen. "Like a

twig," she said. "You need to eat something?" she asked with a smile.

"No, ma'am," Willy said softly.

She

laughed. "Honey. There's no need to be so proper. Relax! Let's get you a

drink." She walked over to the corner of the massive kitchen and poured

him a glass of brown liquor. She walked back and handed it to him.

"Macallan 12. The gold standard in Scotch Whiskey."

Willy took the glass and nodded. He placed it on the counter. "Not a whiskey guy?" Donna asked.

"I've, umm, I've never had it."

"You'll

like it," she said with a wink as she went to refill her wine glass.

"Have a seat, darling. Let's get to know each other."

Deception and Kink

"So,

yeah that's basically it. We usually have one person on the register,

one doing inventory, and then me." Willy took a sip of his second glass

of Scotch. It was going down much easier and he was getting a bit

buzzed. But he was still painfully nervous and shy.

"Sounds

exciting," Donna said, sarcastically. She was greatly amused by the

young man. She could tell he was extremely nervous despite her efforts

in getting him out of his shell.

Willy

nodded and took another sip. By now, he could tell Donna was much older

than he. He pegged her as being in her forties, maybe even fifties. He

admitted she was pretty, and perhaps even stunning in her early years.

But she was much heavier than girls he normally felt attracted to. She

probably had fifty pounds on him.

"Willy,

do you know why I took an interest in you?" she asked as she stood up

from her chair and approached him. She placed her glass next to his and

put her hand on his shoulder.

Willy gulped. "Umm, well the App paired us, right?"

Donna

laughed. "It was your little hint at the bottom of your profile. And

when I saw it in the picture and video," Donna smiled and shook her

head. "Just incredible."

Willy nodded. "Yeah, I know."

"Willy. Look at me," she said. "Is this what you want? Do you want to be here tonight?"

Willy

didn't know how to answer. He wished his nerves would calm down. He

knew he was being awkward and shy. This was his first real date in his

entire life. He never imagined he'd find himself in a place like this,

in his own hometown no less. He had gotten this woman to take interest

in him on his own merit. He couldn't back down now. He nodded as

confidently as he knew how.

Donna

smiled. She removed her hand from his shoulder and picked up her glass.

"Then follow me downstairs," she said in a whisper.

Willy

followed her down to the basement bedroom suite where she led him to a

large and modern space. The area was well furnished with a bar, movie

theater, and gym. As Willy waited for her to pour them fresh drinks at

the bar, he wondered what on Earth this woman did for a living to afford

such a luxurious home.

"We

bought the house in 2016. Moved here from California. A Physician and

his wife used to live here. I actually think his wife was a Doctor too,"

Donna said as she handed Willy a generously poured Scotch.

To be continued in part 5, by BrazenHorse. For Literotica