The Bright Side

Happy Birthday to me...Friday the 24

th

was my four year anniversary of joining Literotica.com, so as a special treat, four new stories in one go!

The Bright Side: First Time for Everything

In an effort to branch out in the world of writing I made sacrifices to the internet gods, and through the magic of email I have come into possession of some very interesting stories. Funny stories, awkward stories, but most importantly - TRUE stories. Tweaked? Yeah, to make it a little longer. Spiced up in places? Sure thing, I have to pad it out enough to be enjoyable and not super short. Adding my own style and flair? Well, for the sake of humour I'll say yes, but definitely not much!! Also Literotica has rules, after all, and most importantly I wanted to do the tales justice, to make them both enjoyable AND true at heart.

I hope you enjoy reading them as much as I did learning about them myself, and remember...always look on the bright side!

--

This isn't a made-up story. This isn't exaggerated. Sure it's not 100% accurate, but that's the way these things work. It has undergone so few changes that you could count them all using the fingers on one hand. Truly - and sadly - this story is real. And it's the story of my first time.

Well, not exactly my first time, but you'll see what I mean.

His name was Geoffrey. He was cute, I liked him just as most of the girls at school did, and we actually dated for a little while longer after all this happened, but I have to be honest; Geoffrey is dumb.

Like, really dumb.

Like, he couldn't pour piss out of a boot if the instructions were on the heel, dumb.

Even so, looking back on those fond memories...yes I do still like him a little bit, and obviously I liked him a lot when we first started dating, and he will eventually grow up and mature after he reaches like twenty five, and when he does I'm sure he will make a girl very happy one day. But it won't be me, and she'll need to be very smart and very tolerant. Because he is very dumb.

Geoffrey was in my photography class in my last year of high school. It was a small class, so every day I would have to see him, and since there were so few people to talk to I ended up talking to him. Now Geoffrey was also a fairly attractive guy and pretty popular too, so even though I didn't usually get hung up over his type like a lot of my friends, when he asked me if I'd like to go out for coffee I said yes, figuring I should at least give him a chance. Then he asked me if I'd like to go to the movies, and I said yes.

Then one night, near the end of our last school year and about a week or two after my eighteenth birthday, he asked me if I'd like to go out for dinner, on an actual date. By that point I was definitely more attracted to him, and not knowing the embarrassment that was to come, I said yes.

--

"I'm glad we did this," said Stacey as they left the restaurant in Geoffrey's car. "I really like you Geoff." Stacey had worn her nicest jeans and top combo for this date with Geoffrey, her classmate and someone she was very rapidly becoming more and more interested in, and he had been very appreciative of her efforts. All night they had flirted and even outright teased each other, despite their youthful age and relative lack of world experience outside of year twelve. But they were practically adults, finishing school in two months time, and then they could do whatever they wanted. The excitement of finishing study and exams had them both in a good mood, so things were going very well.

"Yeah? I like you too. Actually, I like you a lot, Stacey," Geoffrey said, smiling at her as he started the car and headed for her house. The whole way there Stacey wanted to reach across and do naughty things to him, things she wasn't even sure she could do correctly. She was fairly inexperienced, much to the joy of Bree Weatherly, one of the more popular girls at school, who claimed to have done most things under the sun. Stacey didn't think much of her and she wasn't exactly a role model for others, but if you've been in bed with three guys at once people believe you when you say you've tried most conventional things, and that made it hard to win an argument with her about sex.

Even as inexperienced as she was, Stacey had a plan when Geoffrey pulled into her parent's driveway and switched off the car.

"Looks like no one is home," he said thoughtfully, but Stacey was leaning over and wasn't listening.

"I guess I'll see you...hey, whoa Stacey? Oh...ohhhh..." Geoffrey stuttered into silence as Stacey quickly pulled his pants down and gave his cock a long, wet lick. It sprung hard pretty much straight away, so she took it into her mouth and gave it a suck, testing him out, slowly seeing what worked for them both and what didn't. With each bob of her head she went a little lower on his shaft, but could only manage to take him halfway. Geoffrey apparently thought she needed some help and started to push down on the back of her neck, making her go a little further but gagging her slightly.

Stacey pulled back, took a breath, and tried sucking him again, but Geoffrey just pushed the back of her head down and choked her again, this time causing her to come up coughing painfully.

"Oh shit sorry, Stacey," Geoffrey said panicking. "I-I didn't mean to."

"It's ok..." she said wheezily. "I'm just, er, new to this."

"So am I," Geoffrey said quietly. They looked across from one other and suddenly they were kissing hard, their mouths finding each other and somehow making out, a slip of the tongue here or there. Stacey found herself trying to clamber across and sit in his lap, but her bottom hit the wheel and the horn went off, scaring her. She quickly attempted to sit down in his lap and accidentally sat right on Geoffrey's cock, almost bending it and eliciting a sharp cry of discomfort from him as she flopped back over the handbrake and into the passenger seat.

"Oooooh sorry! Sorry," she cried, flapping her hands. Stacey looked up at the darkened house and a thought came to mind.

"You know, my parents aren't supposed to be home for a little while...why don't you just...come inside?" she said seductively. Geoffrey looked up with a hopeful gleam in his eye.

"Yeah?"

"Yeah."

"Ok, definitely...let's go!" he said, getting out as quickly as he could while still in a bit of discomfort, hitching his pants back up. Stacey got out as well, taking his hand and dashing to the front door with her keys.

Once they got inside Stacey led Geoffrey to her bedroom, shutting the door and turning her bedside light on, lowering the output for a bit of mood lighting. She turned around and sat on the bed, Geoffrey joining her before she tugged his pants down again and lowered her head into his lap.

"Now don't push my head down, ok?" she said strictly. Geoffrey, unable to believe he was in her room, nodded enthusiastically.

"Ok sure, I won't," he promised. Stacey smiled and lowered her mouth over his cock again, giving it a few short sucks to get it extra hard and wet before bobbing her head a little slower, giving his cock long, tender sucks. She twirled her tongue around the head of his cock, trying her best to keep her teeth away from him and to make him happy. Geoffrey rested his hand on her head, but at a warning moan from her he slid it down her back to lift her shirt gently, rubbing her bare skin.

"Stacey...I want you," he murmured. Stacey paused with Geoffrey's cock in her mouth and thought about it. She was loving the pleasure this gave her, and she wanted some for herself. She had no real limits on when to have sex, just that it had to feel right.

I guess I'll know in a minute or two.

"Ok."

"Wait, really? You want to??"

"I want to...try," she said timidly. Geoffrey lifted her head from his lap and kissed her lovingly, then stood her up and shimmied her jeans down, and as she kicked them off her feet he pulled down her panties as well. Geoffrey stared at her pussy, the first one he'd ever seen, with awe. Stacey was neatly trimmed and had dark brown pubic hair, and her legs were shivering slightly with anticipation. Geoffrey stood up as her panties slid right down to the flor and she stood there, wearing just her shirt and her socks, before he gently laid her down on the bed, dropping his own pants and moving over her.

Stacey looked down between her legs and saw Geoffrey's long, hard cock poised at her pussy ready to go. She was nervous, very nervous, but she wanted to feel him in her, so she reached out and held his bumcheeks in her hands, pulling him forward.

"Gently," she whispered, as Geoffrey leaned over her and thrust forward. She felt the tip of his cock penetrate her folds, then slowly ease further into her until he was half inside her pussy. It felt a little odd but amazing. Then Geoffrey pulled back and thrust in a little deeper and Stacey started to get scared.

"Geoff no...wait!" she said, and thankfully he stopped straight away. Stacey loved the feeling of his cock inside her, but it was about to go one step too far.

"I'm sorry, I can't," she said, stroking the side of his face. "I want to, I desperately do, but we can't...not yet." Geoffrey nodded and pulled back, making Stacey whimper as he slid out of her. She felt so empty without it.

"I'm sorry Stacey," said Geoffrey. "I didn't mean to upset you."

"No! No Geoff, you didn't, trust me I'm as frustrated as you are...I want to do it I just..."

"...just not right now," Geoffrey finished, lying beside her. Stacey lay on her back, the heat between her thighs driving her mad.

"What else could we do? I want something!" Stacey closed her eyes, frustrated. It had felt so good having him inside her, she desperately wanted more, wanted him to go deeper...

"Well, maybe we could, you know...do anal?" he said timidly. Stacey opened her eyes and looked at him, lost for words. She hadn't really thought about it much and it definitely wouldn't have been her first choice.

"Anal?"

"Yeah, you know, in the butt..."

"I know what it is!" she said, stalling for time. Stacey hated to take another leaf out of Bree Weatherly's book but by all accounts anal felt really good if done properly. By now though her legs were wet with desire and any chance to be filled by Geoffrey was looking like a good move. She bit her lip and sighed.

"Okaaaay, but you HAVE to be gentle to start!" Geoffrey nodded eagerly and stood up as she reached over to her bedside table, getting out a small bottle of massage oil. It was basically lube, so Stacey squirted a little onto his cock and rubbed it gently, loving the feeling of it in her hand. Then, feeling a tiny bit silly, she squirted more into her hand, reached down between her legs and rubbed her asshole, gently poking a finger into herself. It felt super weird, and she wasn't sure if she could go through with it, but she got on her hands and knees anyway, positioning herself at the edge of the bed.

"A little closer, right on the edge of the bed," Geoffrey instructed her. Stacey wriggled back so her shins were off the bed and her knees were on the edge and looked back at him timidly.

"Like this?"

"Yeah. Wait, lower your chest, make your ass stick up." Stacey did and felt him move between her legs, getting nice and close to her. She was even more nervous than before and gripped the sheets tightly, feeling Geoffrey's penis rub her from behind. He reached down and gripped it so he could aim it at her hole, and very lightly pressed against it.

"Ready?"

"Yeah," she mumbled. Stacey felt the head of Geoffrey's cock push against her anus, then gasped as the tip suddenly penetrated her.

"Wait! Leave it there, just wait."

Geoffrey paused, letting her get over the initial contact. She took a deep breath and nodded, clenching her jaw as the shaft of Geoffrey's cock slid into her tight hole. It was rough and she felt stretched beyond belief, biting back a moan of discomfort.

"Uhhh, so warm, so tight," Geoffrey moaned from behind her. Stacey waited for him to stop but he didn't, he just kept pushing his cock deeper inside her, until eventually she couldn't take it any further and Stacey threw her head back and cried out.

"Ahh, that's too much, no no no TOO MUCH!" she gasped, reaching back to put her hand against his leg. Geoffrey stopped and eased his cock back a little bit, afraid of hurting her.

"Are you ok?"

"Y-yes, just, not so deep," she breathed.

"Ok," he said back, gently pulling out of her. Stacey started to feel a little better until he eased back in, faster than he did the first time, but at least he didn't slide quite as deep. Stacey pressed her face to the sheets in front of her and reached back, parting her cheeks to try to make it feel better.

Geoffrey looked down at the image of his shaft in Stacey's tight anus, her painted nails holding her rosy soft cheeks apart to take him inside herself, and it drove him crazy with lust. Her asshole clenched a little around him and he took that as a sign to move again, thrusting his cock back and forth inside Stacey's ass. His hands rested on the small of her back, rubbing up underneath her shirt and caressing her hips as his cock slid in and out a little faster.

"Oh wow, Stacey, this is so good," Geoffrey moaned. "You're so tight." Stacey moaned into the blanket, turning her face to one side to look over at him as he pounded her. It hurt, but not as bad as when he started, and the rhythm they were making, the feeling of his cock inside her - just knowing that he was fucking her, even if it was her ass - was so hot she couldn't help but get more and more aroused. One of her hands let go of her asscheek and she spread her legs a little to slip her hand between them, rubbing her wet folds gently.

As Geoffrey sped up just a little bit his balls began slapping her ass, even though he wasn't pushing as deep as possible, and Stacey's fingers quickly became coated in her own juices as she played with herself. She rubbed her clit furiously and over and over in her head the thought about all the girls in the porno DVD's she loved watching.

He's fucking me. He's fucking me. He's FUCKING me. Give it to me Geoffrey. I need this so badly. Yes, oh FUCK yes. Fuck me. Fuck my ass, my hot virgin ass. Oh God. Harder, harder...

"...harder..." she moaned out loud.

Geoffrey was stunned, but he knew how tight she was and that he couldn't hold on for much longer and started to move quicker still, his hands holding her in place as he thrust into her ass. Each time he pulled out her hole contracted around him and her body was rocking with each thrust back inside, the sexy painted nails of one hand gripping the soft flesh of her asscheek while the other fingered her own pussy. Geoffrey leaned back and fucked her hard, feeling his release coming up fast.

Stacey realized he was getting rougher as well, and as while it spiked her lust even higher she could feel herself beginning to slip off the edge of the bed with the motion of their fucking. Trying not to let the feeling between her legs fade away, she grabbed hold of the sheets and shuffled her knees a bit further up on the bed, but she started slipping back down towards Geoffrey. She tried again and stretched one knee up higher, letting her balance precariously but mercifully away from the edge, keeping his angle into her perfect as her hand worked her folds again.

Geoffrey held Stacey tight and started to thrust faster and shorter, stabbing into her with real urgency. He could feel his release coming and the more she squirmed and writhed in front of him the more he wanted to blow inside her. Stacey abandoned her attempts at fingering her pussy and gripped the sheets, trying desperately to keep her lower half away from the edge of the bed, afraid her knees would slide off and she would fall back against Geoffrey, impaling herself down on his entire cock. Geoffrey didn't seem to notice and leant over a little, his arms wrapping around her belly and holding her close to him. Unfortunately, the extra weight on the small of her back made her slip much closer to the end of the bed, and even as she dug her fingers into the sheets she felt one of her knees slip off completely.

"Oh shit Stacey, I, I think I'm...AAA-AAAHHHH!" With an extra hard thrust both of Stacey's legs slipped completely off the bed as Geoffrey pushed himself deep into Stacey's ass, his weight forcing her flat onto her belly as his cock sprayed cum inside her. Stacey's eyes shot open as her asshole felt like it was being ripped open by his entire length sliding as deep as he could go into her. She tried to push herself up off the bed with her hands, crying out loudly and kicking her legs on either side of his body, the shock and pain of his cock sliding in so deep making her tear holes in the bed sheets she was gripping. She felt his warm cum entering her, every painful throb of his shaft as it pumped his massive load into her ass, her tiny hole straining from holding his massive member. The base of his cock pressed hard against her soft cheeks, which were red and raw from being slapped by his thighs. Geoffrey gripped her hips and pressed his chest against her arched back, mistaking her reaction as a sign of pleasure rather than discomfort.

"Oh ow ow ow ow ow!"

"Ohhh fuck Stacey, ah, ah, ahhhh..." Geoffrey's cock eventually stopped having spasms and they lay down, Geoffrey on top of Stacey, his shaft still buried painfully deep in her asshole. He was panting hard and holding her tightly, his whole weight keeping him firmly inside her. Stacey twisted her head so the side of her face was pressed against the mattress and looked back at Geoffrey, who seemed completely ignorant to her anxiety.

"Ummm, babe, it...kind of really hurts when you stop moving...and you're deep in there like that..."

"Mmm...oh shit! Sorry Stacey!" Geoffrey exclaimed, leaning up on his hands and unintentionally pressing the head of his cock in hard for a moment. Stacey grimaced and heard a loud "plop" as his shaft was pulled out of her, the walls of her ass burning a little.

"Is that better?" he asked. Stacey nodded, although it still hurt like a bitch. Geoffrey tried to casually lie down next to Stacey, cuddling up to her a little. "So...that was interesting, wasn't it? I've been aching to cum for so long...there was so much of it!" He gave her belly a soft squeeze and kissed her cheek, but as he did Stacey's eyes opened wide.

"I, I think I need to go get cleaned up."

"Yeah, me too, who knows when someone might come knocking!" Geoffrey said, his arm around Stacey's slender waist. Stacey looked at him, shaking her head madly.

"No, Geoff, as in I need to clean up, right now!" At that very moment he squeezed her again and she gave a very embarrassing fart; it sounded wet.

"Oh, OH! Umm, right." Geoffrey instantly let Stacey go and watched as she inched across the bed, trying noticeably to keep her thighs closed. It looked like she was going to make it, then as she reached the edge and stood up she gave another little fart and squealed, horrified, reaching back with one hand to cover her asshole and squeezing her butt cheeks together as she walked as quickly as she could for the bathroom. Unfortunately a thick line of cum had already trickled out beneath her fingers and was making its way down the back of her thigh as she slammed the door shut.

Geoffrey, feeling decidedly awkward, started getting dressed and tried to ignore the very loud and unladylike sounds coming from the bathroom before he heard the toilet flush. A minute later Stacey opened the door and walked back out, still naked from the waist down. Her backside hurt, she couldn't quite walk naturally and she was feeling confused about everything that had just happened. Part of her wasn't sure if it had been the right decision, not wanting to remember this as her first time having sex, but she was definitely glad she still technically had her virginity.