Note to my readers: Thank you so much for reading my stories and taking the time to write and comment on them. I never imagined I'd be putting stories in my head onto the Internet, but it's been a lot of fun. Two of my stories including the first ever are based on real-life experiences that I think about often to this day. It's been a blast of fun writing these. This will be my last story for a long time, maybe ever. Thanks again for reading.
Several days had passed. William 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 Amanda, 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 Amanda since she left his apartment. William 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 Amanda was completely turned off and likely disgusted. How could William 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 Amanda. 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. William 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 William was definitely a boob guy, he couldn't help but feel excited to meet Donna.
After reading advice online and factoring in Amanda's own assessment from the other night, William 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 Amanda.
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 Amanda'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 Amanda watching him have sex with Jenn. The experience was likely to live in his mental imagery forever.
"Mmmmmm" 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 Amanda 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.
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As William 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. "William," she said as she beckoned him in. "Do come in."
"Ummm," William said, confused. "Is... umm.... Donna here?"
"Who's that?" she asked.
William 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. William 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," William 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."
William 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."
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"So... yeah that's basically it. We usually have one person on the register, one doing inventory, and then me." William 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.
William 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.
"William, 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.
William 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."
William nodded. "Yeah... I know."
"William. Look at me," she said. "Is this what you want? Do you want to be here tonight?"
William 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.
William followed her down to the basement where she led him to a large and modern space. The area was well furnished with a bar, movie theater, and gym. As William 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 William a generously poured Scotch.
"What do you do?" William asked.
Donna smiled. "Retired," she answered as she took his hand and led him to a seating area across the room.
They sat down next to each other on one small section of a large L-shaped sofa. Donna sat on the edge of her seat, angled towards William. After they each took a sip of their drinks, she placed them on the coffee table in front of them. She smiled at him. "Well? Why don't you show me?"
William looked confused. "Come again?"
Donna laughed. "Your penis. Can you show it to me?"
"Oh, right," William said, almost as if it was a foregone conclusion he was expected to show her his dick. "Right now?"
Donna nodded. "Please," she said as she anxiously stared at his crotch.
William slowly unbuckled his belt and jeans. He began to unzip his fly, but suddenly stopped. There was a problem. "Uhh... it's umm... it's not... erect yet."
Donna laughed. "My dear, dear, boy. It's ok. C'mon let's see this sucker!"
