A Geek's First Time Ch. 02

Jill was sitting at the bar having a drink and talking to Lisa, who was serving at the bar tonight.

"So it's been a month since your little boy toy was here," Lisa said with a slight grin.

"Harry isn't my boy toy, we have a night of sex, and that was it," Jill replied, annoyed. "I don't expect him to see again."

"How? Do you think he would be disgusted sucking a dick? Swallowing cum?"

"No, I think he learned his lesson in not leaving his house in a huff on a cold winter's night," Jill said as she took a drink.

"Hmm," the tall blonde woman said. "Shame, I would pay money to tap that ass of his."

Jill burst out laughing. "You fucking whore. You're the reason why Harry hasn't come back."

"Me?" Lisa said, raising an eyebrow.

"Yes, you did say to the poor boy that you would stick two dicks up his ass. That would scare anyone."

Lisa rolled her eyes. "The boy needs to learn true pleasure, and if he comes back. I will show him that pleasure."

"Double anal straight off the bat would scar the poor boy," Jill replied. "You need to start slow, then loosen him up, then double team him."

Lisa burst out laughing. "I think we should double team, Harry. What do you say? Just imagine it our dicks in his tight little hole."

"Stop it, Lisa!" Jill said, rubbing her cock between her thighs. "You're making me horny."

"You need to wank don't you?" Lisa grinned. "Go on then. Go to the little girl's room and stroke that dick of yours. Or if you prefer, you can over to this side of the bar and serve the girls while I suck you off."

"Fuck you!" Jill said as her cheeks turned red and ran to the bathroom to have a wank.

Lisa began to chuckle as she put the empty glasses on the bar into the dishwasher. When she was done doing that, she saw Harry walking into the room and walking over to the bar.

"Hello, stud," Lisa grinned.

"Oh hello... Lisa wasn't it?" Harry replied.

"Indeed it is," Lisa said, surprised that Harry remembered her name. "How can I help you?

"Is Jill here tonight?" Harry asked.

Lisa let out a small giggle. "Oh, course, she is here. Jill is in the ladies room, stroking her dick thinking about you." Harry's face turned red as Lisa began to laugh. "So anyway, what can I get you?"

"Water, please."

"Coming right up," Lisa said.

Jill walked out of the bathroom. It didn't take her long to shoot her load. She did miss Harry and wished she got to see him again.

She noticed a male with black hair sitting at the bar and froze. "Harry?" She walked over to the bar, and Harry turned to meet her.

"Hi Jill," Harry said warmly.

"Harry," Jill smiled. "It's nice to see you again."

"Hey, Harry," Lisa smirked. "How was sucking Jill's dick for the time first?" She placed a glass of water on the bar.

Harry and Jill's faces began to glow red.

"Come on, Harry, you need to tell me what it felt like having your big dick up Jill's tight little ass."

Jill quickly grabbed the glass of water and threw it at Lisa.

"Hey Lisa, you've made a mess. Go and clean yourself up," Jill said.

"Bitch," Lisa chuckled and walked away to dry herself.

Jill walked into the bar. "Sorry about that Harry, was it water in that glass?"

"Yeah, it was," Harry said, embarrassed.

"Coming right up," Jill said as she got a glass and filled it up with water. "I'm surprised to see you again, Harry. Why did you come back?"

"I... Well, I wanted to ask you something," Harry replied with a blush.

Jill placed the glass of water onto the bar. "What is it?" Jill replied, smiling.

"I wanted to know if you wanted to fuck my ass as a thank you for looking after me last month."

Jill sighed. "Harry, you don't need to offer your ass to me. Remember what I said to you last month? I wasn't planning to fuck you, but I saw your big dick, and..." Jill's face grew red, and she began to laugh a little bit. "I needed it, and also, I'm more of a bottom than top."

"Oh, I see," Harry said, disappointed. "The reason I was asked you, Jill, is because I was interested in getting my ass fucked. Only by a transsexual woman, of course, you've opened me a new door for me."

Jill began to rub her face. "I mean, if you're interested in finding out what it feels like. Maybe one day."

Harry smiled. "Thanks, Jill. I wouldn't ask anyone else."

Jill felt her heart skip a bit.

"So, how have things been anyway?" Harry asked.

"Meh, the same honestly, living during the day and coming at night to work and earn a wage. What about you? How is that streaming thing coming along?"

"Oh, I've just reached 50 followers means which I can enter into a partnership, which I've applied for," Harry replied.

"Right..." Jill replied, having no idea what Harry was talking about.

"A partnership means I can start making money now. Of course, I'm not a big name, nor I'll ever be, but hopefully, I can gain a small fan base so I can earn some cash, but more importantly, earn money for the charity stream I told you about."

"Oh yeah, I do recall you saying that," Jill said. "I also recall you were going to play games. So are you playing the newer games? Or are you playing retro games?"

"Retro games," Harry replied. "I don't have a strong enough computer to play the latest Triple-A titles. One day that is the goal, but right now, I need to take one step at a time."

"I hope you do well, Harry," Jill smiled. "You're a smart young man who is kind and far more mature than my age group."

"My age group as well," Harry replied.

"True, so are you still up for a bit of fun?" Jill asked.

"What do you have in mind?" Harry replied.

A slight smirk appeared on Jill's face. "Well, I was thinking of us going back to my flat and me bending over and you sticking your big dick in my tight ass."

Harry's cock began to grow. "Sure," he replied, blushing.

"Why are you blushing?" Jill said with a giggle.

"My dick is growing hard."

Jill leaned over to Harry and put her mouth to his ear. "I need that dick, Harry. Keep it hard for me, love."

Lisa arrived back, and she grinned. "Stop whispering to the poor boy toy and take him home right now. You're not working tonight. Plus, look at poor Harry's face is pure red."

Harry hid his face with his hands, causing both women to laugh.

"Let me grab my coat," Jill said as she left the bar.

"Hey Harry," Lisa said seriously.

"Yeah?" Harry replied, surprised by Lisa tone.

"This is the happiest I've seen Jill in years. Don't be a dick, alright?"

"I-I wasn't planning to be one," Harry said, shocked.

"Good," Lisa said, walking into the bar. "Jill has had a rough life if you hurt her or even upset her. I will find you."

Harry was ready to ask what happened to Jill. But he never got a chance when he felt Jill's arm wrapped around his.

"Ready," Jill said.

"You two have fun," Lisa smiled. "Harry, give her a good fucking will ya."

"Shut up!" Jill said, embarrassed.

Harry stood up and didn't reply. He and Jill walked out of the club while Lisa shook her head. "Maybe I was too blunt with Harry."

The night was cold, but thankfully for Lisa and Harry, they were nicely wrapped up. Unlike their last walk together, this one was met with silence. This worried Jill as she began to thought Harry was having second thoughts.

"Hey Harry," Jill said, concerned.

"Yeah?" Harry replied.

"Are you ok?"

"Oh yeah, sorry, I was in deep thought. Lisa said something to me which shocked me."

"Let me guess. Lisa wants to try and stick three dicks up your ass, right?"

"No," Harry said, stopping causing Jill to stop as well. "She told me you had a rough life and told me not to be a dick to you."

Jill left out a sigh that hinted towards anger. "See that woman! Harry, forget what she said, ok. It's nothing for yourself to be concerned with, ok."

"Are you sure? Because the last thing I want is to upset you."

"Yes, please, Harry, forget about it," Jill said softly as she began to walk again, taking Harry with her. "Anyway, do you have a thing for the older woman?"

"I don't think I do," Harry replied. "Why do you ask?"

"Because I'm 16 years your senior."

"Age is just a number. What I see is a beautiful woman."

Jill began to blush. "Well, you have your way with words."

Soon the pair arrived at Jill's flat, and soon as they got inside. Jill quickly got to her knees and pulled Harry's jeans down, then his boxers.

"Hmm, it's a lot smaller than I remember," Jill giggled.

"Hey, I'm not warmed up yet," Harry said, embarrassed.

"Let's change that, shall we?" Jill said as she opened her mouth and took Harry's soft cock.

"Fuck," Harry moaned softly as he felt Jill's soft mouth on his member.

Jill began to bobble on the cock as she felt it get bigger.

"Please, not so fast," Harry begged. "I'm going to cum too soon."

Jill ignored Harry and began to lick the head of the dick. She put one of her hands on his balls and began to play with them gently.

"SHIT!" Harry roared as he flooded Jill's mouth with cum.

Jill swallowed her prize, and she pulled her mouth away, licking her lips in the process. "Thanks for the protein," she giggled.

"Sorry," Harry said, disappointed. "For not lasting long."

"Don't be," Jill replied as she stood up. "Remember last month? You lasted much longer before you came for the second time. So I'm doing the same here again. Now stud, get into my bedroom and stirp. I'm going to go into the bathroom and clean up."

Jill ran to the bathroom, excited, while Harry couldn't help but smile. He found Jill adorable when excited. He walked into the bedroom, took off his top, threw it on the floor, and sat on the bed while slowly stroking his rock hard cock.

Harry didn't need to wait long as his mouth dropped when he saw the blonde bombshell Jill walked in.

"Careful," Jill grinned. "You will catch flies."

"Sorry, but I forgot how amazing your body was," Harry replied.

"Cheers, love, I try my best to keep in shape," she replied, went into her drawer and pulled out a condom and lube. Jill got onto her knees, put the rubber on Harry's dick, and then covered it with lube. Then, she put some around her hole.

"Jill, wait!" Harry said quickly.

"What is it?" Jill said, concerned that Harry was having second thoughts.

"There is something I want to try first."

"What is it?" Jill said, looking at Harry in confusion.

"I want to eat you out," Harry said, blushing. "I...er...saw a video on rimming, and I wanted to try and pleasure you."

Jill felt her heart skip a beat. "Oh Harry, you're a little gem. Get on your knees then."

Harry did what he was told and got on his knees while watching Jill get onto the bed, laid on her back, as rested her ass against the edge of the bed.

Harry saw Jill's tiny hole, and he moved his head towards it and stuck his tongue out and made contact with it. Then he began to move his tongue up and down, causing Jill to moan softly.

"That's good, Harry," she said.

Harry felt happy, and he began to stick his tongue into her ass. Then he raised one of his hands, grabbed Jill's semi-hard dick, and began stroking it.

"Please, don't stop," Jill begged.

Harry felt Jill's cock grow to its five inches as he continued to stroke her dick while he pushed his tongue deeper into Jill's ass.

"Fuck! I'm not going to last!" Jill moaned.

Harry pulled away from Jill's ass and guided his head to Jill's cock and swallowed it whole, and began to bobble his head up and down.

Jill clinched the bedsheet with both hands as she was overflowed with pleasure. Harry was everything she wanted in a lover. He was kind and respectful.

Harry pulled his mouth away from the dick. "If you don't give me your cum, then I'm not fucking your ass." Then he went back to sucking Jill's dick.

"You bloody tease," Jill moaned. "Fucking take my load."

Harry felt his mouth flood with Jill's cum. He swallowed everything she gave him. Then stood up and felt the cock slide from his lips.

Jill saw Harry standing before her. "Fuck me, Harry! Fuck my ass!" She grabbed a pillow and put it under her ass to give Harry better access.

Harry grabbed his cock and placed it at Jill's hole, and slowly pushed in. Both moaned in pleasure as Harry's dick went further inch by inch.

Jill wrapped her legs around Harry's ass, and she wasn't going to let him go any time soon.

Harry finally reached balls deep, and he placed his hands on the bed as he leaned over Jill, and he began to move his hips back and forth.

Jill reached her arms out and placed her hands on Harry's back pulled him down, causing their lips to meet.

Harry froze as this was the first time he kissed a woman. But he felt Jill's tongue trying to wiggle into his mouth he opened, and she felt his tongue play with his. Jill could taste her cum in Harry's mouth as he began to move his hips again as he slowly fucked this beautiful woman.

Jill was heaven. It felt terrific. For her, she and Harry weren't having sex. They were making love. "Oh, Harry faster!"

Harry obeyed as he moved his hips faster, and the pair began to flesh smacking against each other.

Jill kissed Harry again as her mind shut down from the pleasure kissing and the pounding she was receiving.

"Jill...can we try a...new position?" Harry said breathlessly.

"Yeah, let me ride that dick of yours again!"

Harry slowly pulled out, and he heard a pop. Then he got onto the bed and laid down on his back. Then he saw Jill lining her ass over Harry's cock, and she dropped herself on the big pole.

"Fuck!" Jill moaned as she began to bounce up and down.

Harry reached up and began to play with Jill's nipples with his hands.

"Jill, you're amazing!" Harry moaned.

"You are too, honey!

Harry watched Jill's hard cock slap against his stomach and wondered if that would be his cock if he were on top riding Jill's dick.

Jill leaned over and kissed Harry once again. She didn't want this lovemaking session to end. This was the best sex she ever had.

Jill got off Harry's dick and laid beside him on her side. "Fuck me sideways, Harry!"

Harry got on his sides and resumed to fuck her. But this time, Harry gently pulled Jill's face to him, and this time it was him to did the kissing.

Jill began to stroke her cock, which was beginning to get a bit too much for her. "I'm gonna cum!"

Harry began to pound Jill fast and hard. "I'm going to fuck the cum out of you!"

Jill's eyes rolled into the back of her head as she began to spewed what was left in her balls all over the bed. "FUCK!" She roared.

Harry was getting close himself. "Jill, I'm close!"

"Cum...in...my...mouth! Throat fuck me!" Jill said slowly as she tried to recover from her orgasm.

Harry pulled out of Jill's ass, took the condom wrapper off, and moved up to Jill's face.

Jill laid on her back and allowed the cock to go into her mouth. Harry began to move his hips slowly in order not to hurt Jill.

"Here it comes!" Harry groaned as he pulls his cock out but leaving the tip at the edge of Jill's mouth as the cock began to flood Jill's mouth with hot cum.

Jill swallowed all the cum, and soon after, Harry crashed onto the bed next to her.

"Oh wow, that was better than last time," Harry said, looking up to the ceiling.

"Indeed it was," Jill said as she cuddled up to Harry. "Hey Harry, thank you."

"What for?" Harry asked.

"For making love to me, you've made me feel like a woman."

"But you are...well minus the dick."

"No, Harry, what I mean is," Jill said, then she stopped. "Look, forget I said anything. Thank you anyway."

Harry began to wonder if Jill had PTSD. "Jill, you can talk to me. I know we've only met twice. But I'm not like most other men."

Jill let out a small giggle. "Oh Harry, you are one of the best men I've ever met. Maybe in time, I will talk about it. But right now, I want to enjoy the after sex period."

"Yeah, about that, I need to be that typical man and leave after sex," Harry said with guilt.

"Because of your parents?"

"Yeah," Harry sighed.

Jill began to laugh. "Well, it's understandable. Don't feel guilty or anything."

"Can I use your shower before I head?" Harry asked.

"Hmm, I will if we can strike a deal," Jill replied.

"And what is that?"

"Could I get your phone number?"

"Sure," Harry replied.

"And your streaming name," Jill added.

"Huh? You want that as well?"

"Yeah, I...er...would like to watch you," Jill said, blushing.

"Ok, sure," Harry replied.

A few nights later

It was Harry's first stream being in a partnership with the streaming company he was using. Nobody had given him subs or bits. Not that Harry expected to get anyway.

The chat was slow, and the people that were usually on the chat were not present.

Harry was playing a retro game until he got a notification appearing on the screen. "Hey, xJillx, thanks for the follow."

Then a few seconds later, Harry saw another notification appearing on his screen. "Oh, thank you xJillx for the sub. You didn't have to." Then he had a quick look at the chat.

'Hey, I wanna help my favourite guy at the moment x.'

"Wait... Jill, is that you?" Harry said, surprised.

'Yes, love, it's me.'

"Welcome to the stream!" Harry said, blushing. "Oh yeah, thanks for being the first-ever person to giving me a sub."

'You look cute when you are blushing, lol.'

"Not on stream," Harry laughed.

'LOL.'

"Right, I think I'm going to end the stream here. I've been going for three hours. Once again, thank you for those who have appeared, and once again, a special thank you to xJillx for the follow and sub. Catch you guys for the next stream."

Harry ended the stream, and he picked up his phone straight away and began to text Jill. Thanking her for the sub and follow privately, but soon they agreed to meet up to have lunch together.