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27 Year-Old Virgin?

"Emily falls for her friend"

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1.5k words 1.5k words

Emily gasped when he entered her. This was unlike anything she had ever felt before. It’s not that she had never been penetrated, she had been playing with toys since she was in college. She’d even had a girlfriend who fucked her into oblivion with a strap-on dildo and she could not have imagined anything that felt better than that – until now.

This was different, she’d never been with a man before. In truth, she thought she was a lesbian and would be until the day she died. She’d had some amazing sex with the women she’d been with and had even been in love with one or two. But something about this guy was different, she couldn’t figure out if it was his looks, his physique or his kind manner, but she knew the day she had met him six weeks ago, she was attracted to him.

They hadn’t actually dated, just had some mutual friends but it seemed every time they were in the same place together, they would end up talking. She’d told him she was gay and he told her he wasn’t but neither of them seemed to be the least bit bothered by that fact. Then it happened.

They had been at a summer party. They hadn’t gone together but were both glad that the other had been there. They laughed and talked and danced and drank and in the wee hours of the morning it was time to leave. They lived fairly close so he asked if she minded if he walked home with her. They chatted during the 10-minute walk and when they got to her door, she realized that she wanted to be close to him. She pulled him close in a tight hug and then tip-toed up and kissed him. The rush that went through her when he responded surprised her and she knew then that she had to find out what a man felt like inside her. So she invited him in.

No sooner was the door closed behind them than she was pulling at his t-shirt. She gazed at his chest, her gaze falling to his six-pack abs beneath. “Wow,” she breathed as her hands passed over his chest before she took his hands in hers and placed them on her breasts.

“I know I said I’m gay,” she whispered, “but I want you to make love to me.” A trail of clothes fell behind them as they fumbled and stumbled their way to her bedroom. By the time they fell onto her bed, all that was left was their underwear. She pushed him back on the bed and pulled his briefs down over his hips to find a neatly trimmed cock standing firm above his abdomen. She stroked it with the tip of one finger before looking up at his face with a smile.

“Here goes!” she said before opening her mouth and taking him in. His groan signaled his approval as she engulfed him, her lips and tongue trying to mimic what she had seen in the naughty movies she watched when no one else was around. Taking herself off him, she looked up and whispered, “I’ve never done this before, tell me if I’m doing it wrong.” He smiled back and said she was doing just fine before laying his head back and pushing his hips upward to urge her to take him back into her mouth.

His hands found her hair and he guided her to take him deeper. She protested, coming off him, “I’m new at this,” she said. “Let me do it my way.” He nodded and released her hair as she opened her lips and took him in once more. She tried to go a little too deep and gagged a couple of times, her eyes tearing up as she did. Then she felt his hands in her hair again but this time they guided her off his hardness and urged her up along his body until they were face to face.

“My turn,” he whispered, she felt his strong hands roll her onto her back and he began moving slowly downward along her body, using his lips and tongue to seek out those spots that made her react to his touch. His breath was hot against her skin as his lips brushed ever so lightly between her belly button and the top of her opening, now glistening with desire and anticipation.

She thought to herself, “I can’t believe this is happening!” and she felt his tongue flick at her clit. Her hips twitched involuntarily as he massaged it, eventually latching onto it and suckling on it as his tongue danced across its tip. His fingers probed her opening, first one, then a second entering her velvet wetness. She let out an involuntary moan, “Mmmmmmmmmmm,” as he probed inside her, searching for that magical spot that would make her squirm with delight. “There!” she cried when he pressed against it, “Right there!” and his touch sent her higher toward that peak of ecstasy.

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Then suddenly he stopped and moved up along her body, his lips retracing the path they had taken on their trip south. “Why’d you stop?” she moaned and he just smiled in response. He shifted so that one thigh was between her knees and they parted willingly, a mix of excitement and concern flooding through her as she anticipated what was going to happen next. “You have something, don’t you?” she asked. He nodded and moved away from her to retrieve a small foil packet from his wallet.

Handing it to her, she ripped it open and rolled the latex sheath over his length, bending down to kiss the head before moving over him and straddling his hips. “I can’t believe I’m doing this!” she whispered as she positioned herself to feel the end of his cock at her entrance.

“Take your time,” he said softly, “if you want to stop, just stop.” He smiled up at her and his hands found her face, pulling her down to kiss her. She moved her hips a little and lowered herself onto him, enveloping his hardness in a single long slide until his pubic bone bumped against hers. That’s when she gasped.

“Oh my!” Never had she felt so completely filled, it seemed to reach all the way to her very core. She had taken longer and thicker things inside her but this was different, those were inanimate, this was a living thing, warm and pulsating with his heartbeat. She held still for a moment, savouring the feeling of him inside her.

“You okay?’ he asked her, she just nodded her head and smiled before opening her eyes and staring at his.

“Perfect,” she answered. She rose up slowly, feeling the plump ridge of its head massaging her g-spot as it passed over it. She felt a slight resistance as his glans reached her opening and she knew that it was time to move her hips down again, her eyes rolled back in her head as his length penetrated her fully once more and the blissful feeling of fullness captured her. “Ooooohhhh,” came the soft sigh and she began rocking her hips so her clit was massaged by his pubis.

It wasn’t long before she felt her orgasm begin to build. The rocking of her hips increased in pace and intensity, so much so that on a couple of occasions his cock slipped out of her. A quick reposition and he was back inside her. His hands found her breasts as he pushed her upright, the new position putting more rubbing pressure on her g-spot and her orgasm built higher. A few more strokes and he stiffened, pushing his hips up into her as he came. Through the latex sheath, she felt the pulsing of his shaft and the warmth of his issue as it pooled at the end of it. She dared not stop now and she prayed he would remain hard enough for her to finish what she so desperately craved. Her fingers found her clit and after only a few quick flicks it happened. The sounds from their union became wet and squishy as she came, her fluid flowing over him and down onto the sheet below them. Her pace slowed as her arousal built to its peak and then began to fade.

She allowed herself to enjoy this feeling of being properly fucked before she leaned down and kissed him, softly this time, hoping that through her lips she could convey the satisfaction and gratitude she felt. As their breathing slowed to normal, he had the good sense to say nothing, choosing to wait until she broke the silence.

“That was nice,” she whispered between kisses. He nodded in agreement. “Wow, twenty-seven years old and my first real cock.” She kissed him again, “It won’t be my last!” She laid on top of him and hugged him tightly. “Do you know my girlfriend Kim?”

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Written by CaressofSteel
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