A Geek's First Time

Harry was walking through town after having a falling out with his parents about his future career as a streamer. The 19-year-old wanted to play video games and stream himself playing the games to the world.

However, his parents didn't think it was a real job and told Harry to focus on getting one.

Harry did have a part-time job as a receptionist that he got when he turned 16. He did weekends while he was at school. But since leaving at 18, he did a few weekday shifts. The extra money helped him to get a decent computer to stream and play games.

It was a cold winters night, and Harry realised that he didn't think this through. He only had about £25 in his wallet and nowhere to crash for the evening. His pride wouldn't allow him to go back to his parents.

He didn't have a clue what he was going to do. But there was one thing he knew he needed to do, and it was to find someplace warm before he froze to death.

He came across a club that had no bouncer and headed inside without thinking. The heat that greeted him was a blessing.

"I need to stay in here as long as possible," he said to himself.

Harry walked down the corridor and went into the main room, which had a bar, chairs and tables and a dance floor in the middle of the room. Music was playing in the background.

Harry noticed there was a lot of women chatting and dancing, but a few of them looked off, but he couldn't his finger on it. He walked over to the bar and sat down.

"Hey there," said a female bartender. "I haven't seen your face before. First time coming here?"

"Yeah, truth be told, I needed a place to keep warm, and I came across this place. Do you sell water?"

"Of course we do, it will be 50p. But can I see your ID first? I just need to check that you're old enough to be allowed in here."

"Perfect," Harry said as he stood up and took his wallet out and opened it and grabbed a pound coin and his ID. "There you go."

"Cheers," said the woman taking the coin and ID and had a quick look. "You're good." She handed Harry back the ID and went into the till and pulled out 50p. "There you go," she said, giving him the coin. Then she got to work getting him a glass of water.

Harry turned around to look at the room again, and he had to admit it looked nice. He did catch a few of the women looking at him licking their lips.

He wasn't a bad catch. He was 5ft8, had short black hair and was skinny. He also had green eyes.

"There you go love," the woman said.

Harry turned around. "Thank you."

"No problem, so what is your name?"

"Harry, and yours?"

"Jill," she smiled, "Nice to meet you love."

Jill looked to be in her mid 30's she had blonde hair that reached down to her shoulders, she had C cup breasts and was slim and was around the same height as him.

"Nice to meet you as well," Harry nodded then he took a sip of his water.

"So are you a top or bottom?" Jill asked.

"Excuse me?" Harry replied, confused.

"Do you take the dick or do you give it out?"

"Do I take dick?" Harry said, further confused. "I'm not gay."

A smile grin appears on Jill's face. "Love, do you have any clue what kind of club in your in right now?"

"No..." Harry replied nervously as he turned around, and nothing seemed out of place apart from the women staring at him like he was a piece of meat.

Harry turned back around to face Jill.

"You're in a transgender club Harry, most of us girls are packing heat," Jill said.

The news froze Harry for a few seconds. Then he took another sip of his water slowly.

"You're quite the catch I must say, Harry. I wouldn't mind taking you home with me tonight."

"So you can fuck me, yeah?" Harry said nervously.

Jill winked this made Harry blush a tiny bit. "You said you weren't gay, so taking you home is out of the question. Don't worry, though, you stick with me at this bar, and I will protect you from the girls."

"Oh, ok, thanks."

"So what are you doing in a place like this?" Jill asked.

"I had a fallen out with my parents, and I walked out of the house without thinking."

"That's not good love."

"Yeah," Harry sighed. "I can't go back. My pride won't let me."

"So, you're homeless for the night?" Jill asked.

"Yip, I need to figure something out soon."

A woman walked up to the bar, and Jill served them while Harry was deep in thought.

"Hey there good looking," said the woman.

Harry turned his head and saw this tall woman with blonde hair licking her lips at him.

"Oh hey," Harry said nervously.

"What is a cute little thing like you sitting here by yourself. Come over and sit with us. We show you a good night."

"Back off, Lisa!" Jill said. "Harry here isn't interested in us women. He is in here to escape the cold winter's night. He isn't causing me problems, so I wish for you not to cause him problems."

Harry took a sip of his water to avoid eye contact with Lisa.

"Fine, it's a fucking shame too, because we keen to double anal Harry too," Lisa said, annoyed. "He looks like he could be our bitch."

Harry spat out his water in surprise.

Jill finished making the drinks and put them on a tray which Lisa picked up and walked away.

"You alright, love?" Jill asked.

"Yeah, I'm sorry for the water, I...I haven't heard anyone talk about me like that before."

"Yeah, all of us are horny," Jill chuckled. "But stick with me, and you won't be a whore for woman dick."

"Thank you, Jill, I mean it!"

"No worries, love," Jill smiled. "We just need to figure out a plan for you."

"I have one," Harry said nervously.

"Well let's hear it then?"

"I..." Harry blushed. "I...er..."

"Take your time," Jill said.

"See how you said you would take me home to fuck me? Well, could I stay at the nights at yours and I'll offer my body in return?"

Jill stared at Harry for a few seconds before she burst out laughing.

Harry's face was red as a tomato. He couldn't believe he just offered his body for a night to stay warm.

"Oh my days you are so cute," Jill said, wiping the tears away. "I thought you weren't gay?"

"I would be willing to push past my comfort zone to survive."

"Alright, you have yourself a deal, Harry," Jill smiled. But unknown to Harry. Jill had no interest in sleeping with him. She just wanted Harry to have a place to sleep for tonight.

A few hours later

It was 11 pm, and Jill had finished her shift. She and Harry left the club which was full now. Jill had to fight off a few of the women that wanted a piece of Harry. At the same time, the young man was blushing for most of the night.

"So," Jill said as she and Harry walked through the streets. "What age do you think I am?"

"Erm mid-30s, I want to say," Harry replied.

"Not bad, I'm 35," Jill replied. "So is this first time going to a woman's flat?"

"This is my first time with a woman ever," Harry replied. "I'm a geek. I love my sci-fi and video games."

"Oh so, you're a virgin, lucky me," Jill chuckled. "You should be lucky that Lisa and her friends never got their hands on you. Your ass would be destroyed."

"My ass is going to get destroyed anyway," Harry replied. "I can't believe I'm going to have a dick up my ass."

"You will like it, I will be gentle with you," Jill said, trying to calm Harry's nerves.

Harry's phone began to ring, and he took it out of his pocket. "Go away, mum!" He said, putting the phone back into his pocket.

"You should answer it," Jill said. "To at least ensure your mum from stop worrying."

"It is her and my father's fault for me leaving home! Why can't they let me pick a future that I want!"

"Which is?" Jill asked.

"I want to become a streamer that plays video games," Harry replied. "I know I won't be as big as the other streamers out there. But I want to be popular enough, so I can do charity streams and help other people! But my parents think streaming isn't a real job."

"Old folk, eh?" Jill replied with a little laugh.

"I know right," Harry sighed.

The pair reached reach the flats that Jill stayed at. They headed inside and climbed up a few levels until they reached Jill's door.

"I'm sorry about the mess, I wasn't expecting to bring home a hot stud tonight," Jill said as she opened the door.

The pair walked in, and Harry was stunned by the pile of clothes that laid in the living room.

"Wow, this place is messier than my room normally is," Harry said, stunned.

"Hey!" Jill said, offended. "As I said, I didn't expect to be taking you home."

"Sorry," Harry said. "So..umm...do you want me on my knees?"

"Pardon?" Jill said, looking at him funny.

"So you can fuck me?"

"Oh yeah that, I need you to take a small shower first to warm yourself up. Just dump your clothes here, keep if your boxers on right now if you like. We wouldn't want you to die of embarrassment."

Harry blushed as he pulled out his phone and wallet and put them on the small wooden table next to the sofa. He took his jacket, t-shirt, jeans and socks off.

"Mmmm not bad," Jill said, nodding her head. "Yip, Lisa and friends would have destroyed you for sure."

Harry's face turned red, leaving Jill to chuckle as she took him to the bathroom.

"There should be a towel already in there," Jill said. "Give yourself a good clean as well. I like my men clean."

"Oh ok," Harry said as he walked into the bathroom.

Jill went back into the living room and noticed that Harry's phone began to ring. She walked over to the table, and the word mum was on screen.

Jill took a breath and picked up the phone and answered. "Hello?"

"Oh, Harry, I'm hap.... Wait? Who is this?"

"My name is Jill, are you Harry's mother?"

"Yes, where is Harry? Is he alright? Why are you on his phone?"

"He is in my shower, taking a warm shower. He is fine, and he refused to answer your calls. So I did instead to let you know that he is safe."

"Thank you so much!" Harry's mother said relieved. "I'm sorry about him."

"It's fine. Harry is a nice young man. It would be rude of me not to help him out. I will have him home tomorrow morning."

"Are you sure? His father or I could pick him up right now."

"It's too late plus is cold right now. Harry is in safe hands. I will get him home tomorrow you have my word."

"Ok then, tell him that my father and I are sorry for losing the rag."

"Well do, goodnight," Jill replied.

"Goodnight."

Jill put the phone down. "At least that is sorted," she said, stretching her arms. "Right I better find a blanket for Harry and clean up this sofa so he can sleep on it."

Jill stood up and began to pick up the clothes that she had left lying around.

"Hey, Jill," said a nervous voice. "That's me ready."

Jill turned around to see Harry naked in front of her. Her eyes travelled down to his dick, and her jaw hung open, dropping the clothes in the process. She was staring at a well-groomed area with an eight-inch dick

"You're big!" She said.

"Huh? We are the same height," he replied, confused.

"Not your height your dick!"

"Oh yeah," he blushed. "I couldn't keep it down."

'Ok then change of plans,' Jill thought. "Harry, I'm going, to be honest with you. I never had any desire to have sex with you."

"You didn't?" Harry replied, confused.

"No, I only took your offer as a means you would have a place to stay for the night. However, now that I have seen your cock." She walked over and put her mouth to his ear. "I want it," she whispered. "Do I have your permission to suck you?"

"If you w-want," Harry replied, embarrassed as his face turned red.

The young man watched Jill slowly drop to her knees, and she gently grabbed his cock.

"It's so thick as well, I'm going to enjoy this," she chuckled. She opened her mouth and engulfed four inches of the cock.

Harry's eyes rolled into the back of his head as he felt pleasure he never had before wash over him. "Fuck!"

Jill used her tongue on the cock while she bobbled her head, and she could hear the soft, cute moans coming from Harry.

"Please don't stop...it feels amazing," Harry pleaded.

Jill had no plan to stop. Instead, she wanted the young man's cum. She upped her pace and began to play with Harry's balls.

"Oh my god!" Harry moaned. "This is the best feeling ever! I'm close."

Jill pulled out. "Give me everything you have. I want every drop of cum!" Then she put her mouth back on Harry's cock and went to town on it.

Harry's legs felt like craving in this was much better than wanking. He didn't realise oral sex was this amazing.

"Jill, I'm cumming!"

Jill felt her mouth getting flooded by Harry's cum. The thing that surprised her that he didn't stop. She had to swallow as much as she could just to keep up with him.

Harry left out a big sigh as he fell on his backside and laid on the floor, catching his breath. "Holy fuck that was amazing, Jill thank you!"

"You had a lot of cum in those balls of yours," Jill replied after she swallowed the remaining cum. "You were like a canon."

"Is that good or bad?" Harry said, sitting up.

"Good," Jill smiled.

"Oh cool, umm do you want me to return the favour?" Harry asked. "You are letting me stay here for the night."

"Do you feel comfortable? I don't want you to do anything you are uncomfortable with."

"The idea of me sucking cock is wrong, but I want to make it up to you, who knows maybe I'll end up loving the taste of cock."

"At long as you're sure," Jill said, standing up. "Let me head to the shower so I can clean myself up."

Jill left the living room, and Harry sat on the floor as he began to think. If he got so much pleasure from oral sex. Then what would anal sex be like? Would he get the same amount of pleasure if Jill was fucking him or if he was fucking her?

One thing for sure was Jill opened Harry to a new world of pleasure.

Harry stood up and began to pace himself around the living room. Then he stopped in horror. "Wait, I didn't even last that long! Jill sucked me off with ease and made me cum quick."

"It was your first time," Jill said, making Harry jump. "I expect man's first time to end quickly." Harry's eyes widened when he saw that she was naked. His eye's travelled down to her rock, hard dick, and it was five inches.

"You have a nice body," Harry replied as his face grew bright red.

"Thank you, I hope you like my cock as well," Jill chuckled. She walked over to him and softly grabbed his hand. She led him to her bedroom, and she sat on the bed and spreading her legs open. "Get on your knees, Harry."

Harry felt the urge to obey this woman, so he did. He knew what was expected of him as he was level with Jill's dick.

"Last chance to back out, love," Jill said.

Harry didn't reply. Instead, he moved his head forward to the dick and opened his mouth and let the dick enter him. He heard Jill let out a soft moan, so he knew his mouth alone gave Jill some sort of pleasure. As for the dick, the head felt soft and didn't taste bad.

Harry used his tongue to swirl around the dick as he tried to remember the skills Jill used on him. Then he slowly began to bobble his head.

"Don't take to much," Jill said softly. "I don't want you to choke on my dick."

Harry took the advice in and got to work. He had to admit he was enjoying himself and sucking Jill's cock wasn't that bad. It even made him grow hard again, that he was doing something so dirty.

"Love, what are you planning to do when you make me cum?" Jill asked.

Harry froze, he hadn't thought of that. He pulled away, freeing the cock from his mouth. "I don't know. I guess I will swallow it since you did that for my cum."

"You don't have too," Jill said stunned.

"No, I want to repay you for letting me stay here for the night. Just...er...let me know when you're going to cum."

Harry went back to work while Jill's eyes rolled into the back of her head.

"Fuck!" She cried. "This is your first time? I don't believe you!"

Harry raised his hand and began to play with Jill's balls. It felt weird playing with a set of balls that weren't his. But he tried to copy everything that Jill did to him, and it was working.

"Go on and kiss the tip of my cock a kiss," Jill said.

Harry pulled the cock out of his mouth and gave Jill's cock a kiss without question.

"Good boy, now take your hands away and open your mouth with your tongue hanging out."

Harry did as he was told and opened his open, leaving a nice target for Jill to aim in. She began to stroke her cock and harry could only watch as he witnesses this sexy woman stroke her cock.

"I'm close!" Jill said. "You keep your mouth open, and I will dump my load in you." She placed her cock on Harry's mouth as she stroked a few more times. She let out a moan and began to shoot her load into Harry's mouth.

Harry felt his mouth flood up and soon swallowed. The taste wasn't that bad; it was a bit bitter. But other than that, Harry wouldn't mind having second servings.

"Oh, that felt good!" Jill moaned as she fell backwards on her bed.

Harry licked his lips and stayed on his knees, unsure what was going to happen next.

Jill sat up and looked at Harry. "Do you want to have sex, Harry?"

"Umm sure," Harry said nervously.

"Good stuff, you get that dick of yours hard again, while I get the lube and a condom."

Harry put his hand on his semi-hard dick and began to stroke. He watched Jill go into her bedside drawer and pull out a tub of lube and a condom.

"Stand up," she ordered.

Harry stood up with his cock now fully hard once again. Jill tore the condom wrapper open and pulled the condom out and put it on Harry's cock. Then she got the lube and smeared it over the condom. Jill stood up and put some it over her ass, and she turned around and bent over, putting her hands on the bed for support.

Harry could only stare at Jill's perfectly shaped round ass.

"Fuck me, Harry, fuck my ass! Also, don't worry about hurting me. I can take it!"

Harry nervously lined up his dick with her backdoor and slowly pushed it.

"Fuck!" Both of them said at the same time. For Harry, it was how tight Jill's ass was. For Jill, it felt good whenever a big dick entered her.

Harry began to slowly fuck Jill's ass. He wasn't sure if he was doing it right. But her ass was making his dick feel good.

"Come on, boy! Fuck me hard and rough! You don't need to worry about cumming. It will take a lot longer for you to shoot a load a second time. Now fuck me like that slut I am!" Jill ordered.

Harry upped his pace and began to fuck Jill hard.

"Yes, that's it, Harry! Oh, fuck your big dick feels so fucking good! Keep fucking me!"

Harry felt happy that he was giving a woman a good time. It raised his spirits and gave him the confidence to pound Jill harder. He grabbed Jill's hips and gave her powerful thrusts."

"YES!" Jill cried. "That's it Harry keep doing that!"

This continued for a few more minutes until they tried a different position. Harry was on the bed while Jill bounced on his cock cowgirl style.

Harry watched this beautiful woman bounce with her hard dick smacking against his stomach. Harry raised his hands and played with Jill's nipples.

"You have nice boobs," Harry panted.

"Thanks, you have a nice big cock!"

Jill continued to bounce, and it was soon taking it's a toll on Harry's balls.

"Jill, I'm close!"

Jill got herself off Harry's cock and pulled the condom off and began to stroke the thick meat.

"Come on, boy, give me a second load!"

Harry let out a moan as he began to shoot his load, and it went everywhere.

"Fuck!" He said. "That was amazing."

Jill let out a small chuckle as he scooped up a bit of cum from Harry's stomach on her finger and placed the finger in front of his mouth.