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First time with a real woman but not last.

Tags: straight,
A small town boy's night with a big city girl.
It was a hell of a day for Tom. One of the best he'd had in a long time. He was a week away from graduating from high school and finally getting out of this town. He had grown bored by most of the people, some he realized he just didn't like. But all that was going to change soon when he left for college and he knew he would never come back. It's all he could think about until six today, Tom's not thinking about leaving anymore, he's only thinking about the last five hours. His friend Steve was having a party, it was nothing special, same people at the same house, even the same beer but then she walked in.

She looked so different from the crowd and he knew he had to at least talk to her. It's never been a question about courage with Tom, he gets rejected it's not a big deal, it's a matter of putting yourself out there. If you get rejected ninety nine percent of the time that means you have to ask a hundred girls out a night to get laid. Well worth it but he's thankful he's never had to work that hard for it.

But there weren't a hundred of her. Before now he never even thought there could be one of her. She was tall maybe even breaking six foot, pale alabaster skin with out a single flaw and a stunning head of red hair. He was nervous, he hadn't felt this way in a long time, years maybe since he lost his virginity years ago but she was so gorgeous. He had nothing to lose, he had to talk to her but he had to be smart about it because girls like her are rare, how rare he doesn't know, she's the first he's ever seen.

He musters up the last of the courage he needs to walk over and talk to her, he's got his chance to, no one is talking to her, no one has and he knows why. She's too intimidating. All the guys here have been with girls but this is the first real woman they've seen. Perfect proportions, she couldn't be more than a hundred and fifteen pounds. Breasts that are beautiful but not too large, they draw the eyes in but don't offend.

He gave himself a quick look in a mirror, he knew all eyes would be on him soon, all the guys are leering at this beautiful stranger and all the women were looking at her with envy. They'll all talk when they see him with her.

"Hello, I'm Tom, I have to apologize for my friends here, sometimes they can be terrible hosts, there's no reason to ever leave a guest unattended." She smiles slightly, her lips are so perfect.

"It's ok, high school party what could I expect right?"

"Yeah I know what you mean. Again I have to say I'm sorry, can I get you anything?"

"I'm good right now thank you. I'm Gwen by the way." She raises her hand and shows me a glass of punch that she is holding with perfectly manicured hands. Her nails are just the right length, of course they are.

"I'm in town for Stacy's graduation, know her?"

"Yeah, for a couple of years." Stacy was a nice girl but just another girl from here. She was pretty but nothing too special and unfortunately she knew it. She became a dependable fixture at most parties. Every guy knew that if she was available they could always take her to a side room or the backseat of a car once she had a few drinks, on days that she was feeling bad she didn't even need a few drink. It was a common occurrence. Tom even hooked up with her a few times, he couldn't think of who hadn't.

"I'm sorry but I don't see a family resemblance."

"There shouldn't be, I'm a long time friend of the family."

"Cool in town long?"

"Just till the graduation."


They talked for awhile, telling stories. Really Tom could just not relate to her at all. She was a world traveler, mature and executive some fancy company. He just barely bought his first car and was barely allowed to buy cigarettes. Tom felt so small talking to her and finally she said the words that he dreaded she would say.

"Hey this party has been fun but I think I want to take off."

"Hey it's cool it's getting a little lame."

"You wanna come with me?" He couldn't believe he was hearing this, yes more than anything he wanted to leave with her.


"Cool, I'll drive I found this ok place downtown and it's close to where I am staying."

"Alright but I'm only eighteen."

"It's cool, I'll get you in."

They get in her corvette and they drive off to a trendy new club in town. Tom lies about forgetting his wallet and she makes a joke to the doorman about would she be with anyone under twenty one. They both have a few drinks and mingle with the crowd but soon she gets bored with there also.

"Let's go."

"Already? we just got here." This was new to Tom and even though it was in the same town, it wasn't boring but he realized it was because of Gwen.

"Yeah, now come on."


They get in her car again and she gets into the road.

"Hey I just want to say this is like the most fun I've had in a long time."

"Cool, you're not bad for an eighteen year old, pretty fun."


They pull up to a hotel and she parks her car.

"Bars are starting to empty, you should hang out a bit."

"Sure no problem."

They enter her room. It smells slightly like her. Lovely. They sit down on a couch but leave the television off.

"I've been new in town for a couple of days now and you're the first guy that has peaked my interest."

"In a good way right?"

She laughs. "Yeah in a good way." And then the impossible happened, she leaned in and kissed him. It was a wonderful kiss, she was firm with her mouth but not hard. It was great but it caught him off guard and she could feel that.

"Hey you ok with this, are you..."

"Oh no ha ha of course not it's just different but I want to you know right now with you." He was babbling, he was nervous, again but it was all going well.

"Hey relax, I kinda forgot who I'm with, have you ever been with a girl outside of high school?"


"K well lets go slow, then I think you have some things to learn."

"I've had sex quite a few times for a few years."

"No offense sweetie but I saw the girls at the party, that's good for beginners but lacking in refinement, right now your basically just pounding one slab of meat into another, trust me." She begins undoing her blouse, and then her skirt and then she is completely nude except for her shoes. Every inch of her is the same tone of skin.

"First off don't make it seem that you are controlled by hormones like a caveman. Show some restraint, unless you are both really into the moment, then it's a race." Tom begins taking off his clothes and Gwen helps, guiding the pace of his motions.

"We're in no rush, so just embrace me." He hugs her and smells her sweet scent.

"Use the tips of your fingers to caress my back, slowly but change direction and pace then kiss me where you can. Do what feels natural."

She begins kissing his neck and he does the same but then he moves to her shoulder and then slowly down to her breasts, all the while massaging her back slowly and changing intensities. He hears her moan slightly in approval. He moves up and nibbles on her ear before moving to her mouth.

After a few moments she turns away slightly and whispers to him.

"Good, now same as with your fingertips, gently and change pace."

She moves her hands down and guides him into her. He noticed her glory before. It was devoid of hair except for a small strip that was cut short. Different than the girls from school who just cut everything clean off. He thrust into her, gently at first but then harder.

"Pay attention to everything, not just the voice." She whispers to him. He looks at her face and she smiles and closes her eyes. He increases his pace and she moans slightly and then she tenses her hands slightly and she scratches his back slightly. They might leave a mark but to Tom it feels so good.

He wraps his arms around her and moves her around on the couch. Her moaning is increasing and she stops moving her hands and digs straight into his. He's in bliss and close to finishing, he strengthens his thrusts and focuses them upwards into her. She responds by gritting her teeth and shouting. Just then he releases in her completely, he doesn't stop right away.

He continues slowly. She begins kissing him again and has stopped digging into his flesh.

"That was great. You just graduated to a new level." He laughs at her joke. But she's right. That was his first time with a real woman, he could never go back. Now more than ever he wanted to get out of this town just to meet more women like her, only one more week. And Gwen was going to be here that whole week.
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