Breaking in a Virgin

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I was 28 and he was 18 when this happened. I’m 33 now.

One sultry Friday night, Rebecca headed for the club scene after work. She didn’t have a boyfriend and was new to the city so not much else to do. Chose a happening club just a short distance from her condo. Live band, lots of guys and girl her age, it was rocking. She had shed her business attire for a leather mini, a sexy lingerie style top and boots. She called it her “get laid outfit.”

She had long dark hair, a tanned body and ample cleavage. She showed it all off. No bra at all when clubbing. She was about five foot five inches tall and had large breasts that jiggled in her outfit. Most men found her alluring and certainly attractive. Her audacious flirting didn’t hurt either.

She entered the club and got a drink at the bar. She passed on a couple of guys but one guy confidently walked up and started chatting.

“Sexy outfit,” he said. He was about six foot tall in a suit without a tie. Blonde hair, lean body, and a Rolex. He looked her age. “Wanna dance?”

“Sure,” she said, downing the drink. “Love too.”

They danced a couple of numbers then a slower song started. His hand was pretty much on her ass. She didn’t mind. He was kinda sexy. Confident. He did press her close. At one point he was behind her in a sexy dance and moved one hand up her inner thigh and another across one of her breasts. He was making her horny. He must’ve been too since she felt his hardness on her leg.

They sat down and made small talk. He lied and said he worked in finance. She pretty much believed it at the time. They danced again and made out in a booth. He copped quite a few feels of her boobs and even rubbed her pussy a little through her silk panties. She felt his cock to see how big he was. Maybe eight inches. He was comforting and knew what to do. Nice kisser. Rick was his name.

“Want to go to my place?” he asked. “I promise I’m not a weirdo or anything.”

“I live just a few blocks from here. How about my place?”

“Sounds good.”

She wanted to get fucked. He seemed probably good at it. They walked to her condo a just a twenty minute walk Etiler escort away. He liked the development. When they got in the elevator, he kissed her deeply and put his hands up her lingerie top feeling her boobs freely. She hesitated some when he tried to take her panties off and said to wait. He did.

They got in her condo and started making out on the couch. He kissed well, deep and passionate, and quickly was licking her beaded nipples. He pulled her panties over her knees and put a finger in her pussy and thumbed her clit. She had her hand in his pants stroking his underwear-covered cock. It was about eight inches.

“Want to go to my bedroom? More comfy.”

“Yes, love too. I must say you’re very sexy. Hottest woman I’ve met.”

“You’re sexy,” she said with a giggle.

She took off her boots and mini and he go undressed and they slipped under the silk sheets. He loved her full boobs and licked and kissed them a lot while playing with her hairy, but trimmed, pussy.

“I like it,” she said.

“Thank you.”

She moaned as his ministrations on her pussy became more intense. He had slipped a couple of fingers inside. He had manicured fingernails so two fingers fucking her pussy was more than okay. She moaned as he kept his suckling on her nipples. Her juices flowed on his fingers. He kept massaging her clit with his thumb. She was close to cumming as her breath got more labored and she was moaning softly.

“Oh, God, I’m so close to cumming. Please don’t stop. Stay right there.”

“Okay, baby.”

Her body tensed and she moaning loudly grabbing his head tight to her swollen breasts. Her thighs squeezed on his hand and she came hard on his fingers getting her juices all over his hand. She grabbed his hand.

“Let me taste myself.”

It startled him. He had never been this far really with a woman. Making out was one thing. Sex was quite another. He was rock hard though. Hopefully she’d take the lead he thought to himself. A blowjob he hoped. Maybe even she’d swallow. The heavy petting and her cumming to his touch gave him a nervous energy he hadn’t felt before.

She Beşiktaş escort took the lead and kissed him then slid down him and engulfed his cock. He arched his back and lost his breath while she put it all in her soft, velvety mouth. It was cold in the condo but warm in her mouth. He was a little thick but more just long. Easy blowjob for her.

He just sat their moaning, “Oh, God” while she played with it. She looked into his eyes but he kept looking up. She didn’t know but it was his first blowjob. Had a handjob but not from a nude woman or one several years older than him. He wasn’t sure where to put his hands.

“Put you hand on my head,” she asked, sucking his cock. He did. Gentle. “Nice cock. Close to cumming?”

“Oh, yeah.”

She sucked a little rougher and faster massaging his balls too.


He tensed then jerked violently and shot a load in her mouth. His head stayed back. He had cum like a rocket blasting off. She swallowed it then came up and kissed him. He kissed her deeply but he felt nervous to her skin. She moved over and laid back, lit a cigarette.

“You okay? You came real hard.”

“Oh, that was…something. You’re so beautiful.”

“I try to be.”

He called her beautiful several more times. She sensed he wasn’t near her age of 28. Guys blew their load in her mouth in five minutes before though not like that. He still had no idea what to do.

“You have a condom?” she asked.

“What? Oh, yeah, I do. In my wallet.”

“You too nervous to do this?”

“No, not at all. I’m sorry. Haven’t been with a girl like you in awhile is all.”

“You cum tasted nice.”

“Oh, thanks.”

He was like a kid looking for the condom she noticed. Hope he’s not a virgin she thought. I need a good fuck. She extinguished the cigarette. He was back fumbling with the condom wrapper. She felt his cock.

“Hard enough to fuck?”


“Can I ask a question?”

“You a virgin? Too damn nervous not to be.”

“Umm, yes, I am actually. I’m good at the making out part but..”

“I thought so.”

“How Taksim escort old are you?”

He gulped. Nervous she might not fuck him. “Umm, eighteen.”

“I’m 28.”

“Oh, wow. I’m sorry.”

“It’s okay. I just don’t know if I should be the one to take your cherry. It should be special.”

“You are special. Most beautiful woman I know.”

“I need a good fuck but you have to be sure.”

It turned her on realizing she didn’t know, blew him and swallowed. Might be fun taking a virgin. Fuck his brains out as sorta revenge for lying to her.

“Rebecca, I am. Really.”


He sighed.

“We’ll take it slow.”


She took the wrapper and put the condom on his cock. He was rock hard. She put him on top of her.

“Just go slow and easy. Once you get the hang of it, then go faster. If it comes out, don’t worry. It happens.”

“You’re special, Rebecca. Doing this for me and all.”

“It’ll be more special soon.”

He moved his head sideways. It would. She slid his cock in her.

“Now, push forward and get the feel.”

“Oh, God, this feels good.”

“It does.”

“Move back and forth and get a good rhythm. If you feel yourself about to cum, stop.”

He did. He fell out a few times yet he learned quickly. After about ten minutes, he let go and came hard. He just lay on her. He apologized. But, he got hard again quick. He was finally fucking her well. Well as could be asked of a virgin. They kissed and he lasted about twenty minutes. She came and tightened around his cock.

“That’s beautiful,” he said then came in her. “Oh, God. Oh.”

He stayed on her and sucked on her nipples and they kissed. He grew limp and fell out. They went to sleep and fucked again in the morning. In the shower she said, “Not a virgin now.”

“No, thanks to you.”

“Just remember, this is no strings attached. Don’t fall in love. I’m too old for you.”

“Okay. It was great while it lasted.”

She decided against work that morning and they fucked four more times before he left. She gave him a few nude pictures of herself and her panties. She later saw him at the same club. Hopefully, he’d remember all she taught him. He was hitting on some lady she knew that was in her mid-thirties. Her secretary. That fling lasted eight weeks. Too bad she was married. It still makes me laugh.


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