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Are You Serious?

Gemma's dare leads to more fun than expected.

Brad looked at the girl in astonishment. She was in her early twenties, very pretty and, at that moment, looking shocked at what she had just asked him. They were in a busy bar, he didn’t know her and she had just asked him one of the strangest and most provocative questions he could imagine coming from a stranger. “Are you serious?” he questioned.

“Yes.” She swallowed. “It’s a dare. I was dared by my friends to come over and ask you.” She indicated a group of girls in their early twenties who were looking over at them, giggling themselves silly and shuffling out of his gaze.

“Look, I’m sorry. I should’ve told them I wouldn’t do it.” She avoided his eyed and started to turn away.

Brad caught her arm gently and stopped her. “It’s okay. I know all about dares.” He smiled warmly at her and let go of her arm. “So,” he lowered his voice so that his friends couldn’t hear him, “they dared you to come over here and ask if you could hold my… penis while I take a pee?”

She nodded, still uncomfortable with the notion.

“What’s the forfeit if you didn’t ask?” Brad asked.

“First one to back away from a dare has to buy drinks all night.” She swallowed. “I, er, I really can’t afford that this week. So, I… well, I came and asked. I’m sorry.”

“Don’t be.” Brad laughed slightly. “It’s okay. I’d probably do the same in your shoes.” Her features softened as he smiled at her. She had a lovely face, small nose, big eyes and a mouth that smiled easily. Her hair was black and just long enough to show some natural waves, and her slim figure was hugged in a dark red sleeveless dress. Brad thought there was something familiar about her but couldn’t put his finger on it. Eventually he figured she was just someone he had seen around town.

“So, because you’ve asked, does that mean you’ve avoided the forfeit?”

She shook her head and looked at him through squinting eyes. It was obvious this was not the most comfortable thing she’d ever done, even though Brad was trying to put her at ease.

“Well, you can’t go back to them and pay for their drinks all night, that wouldn’t be fair.” He glanced over at her friends, all of them looking slightly inebriated, which she didn’t at all. “You want me to go and have a word with them?”

“No. No,” she urged. “It’s okay, I’m a big girl. I can handle it.”

She neither looked all that big nor ready to take the knocks as Brad looked down into her lost puppy eyes. He sighed as he wondered how to help her out. He knew there was one obvious way, but searched his imagination for another before he made the offer. “Look, rather than you get stiffed paying for their drinks, why don’t we just do what they want? I don’t mind, it’s no big deal for me. I’m Brad by the way.” He offered her his hand.

She shook his hand and said meekly, “Gemma.” She looked at his face while she considered his words. “You’d do that for me? You wouldn’t mind?”

“Sure,” he smiled, “it’s not a big deal.” Looking around the crowded bar swiftly, he bent towards her and said, “I don’t know where we’d go though. Not like we can just walk into the washroom, is it?”

Gemma nodded in agreement and looked around also. “I know. I didn’t think for one minute we’d get as far as actually needing somewhere to go.”

Brad’s lips pursed and his teeth pulled on them as he thought through his options. It was almost with a sigh that he said, “It doesn’t have to be right here does it? We can leave the building can’t we?”

Gemma thought for a few seconds, then shook her head slowly. “The dare was to get you to let me. No one said anything about where. Have you got an idea?”

Brad explained that his office was only two blocks away. He had a key. “There won’t be anyone else there at this time of night though, so I’d understand if you’d rather not. Hell, we’ll just walk into the washrooms here and go for it if we have to.” He laughed. It was a challenge to him now.

“It’s okay.” Gemma’s lips smiled thoughtfully, appreciating his effort and attitude. “We can go there.”

“Nice bunch of friends you’ve got there.” Brad made some conversation as they walked to his office. “Are they always like that, or was this a special treat for you tonight?”

“They’re my older sister’s friends really,” she explained. “They thought it was pretty funny that I didn’t have much money and they wanted to have a few laughs at my expense I guess. I didn’t think it was very fair but they’ve had a lot more to drink than I have.”

When they got to the door of the offices, Brad unlocked it and held it open for Gemma to enter the reception area. As he locked the door again she stood and looked slightly nervous. “Look,” he offered, “I’m sure you can go back now and tell them you did it. I’ll back you up and they’ll never know anything different.”

“It’s okay. I’ll go through with it. It was my dare after all. And anyway,” she half-smirked at him, “now that we’re here, away from them, I’m kinda curious, you know?”

Brad raised his eyes in a “God help me” way and led the way over to the men’s washroom. Once inside they stood facing each other, neither quite sure whose move it was.

“We’ll just use one of those shall we?” Brad nodded towards the line of urinals along the wall. “You want me to… get it out for you?”

There was no mistaking the embarrassment as Gemma’s face started to redden, but still determined to see this through, she nodded and took a step towards him.

Brad took a deep breath and pulled down his zipper slowly. It was almost like he expected her to stop him at any moment. She didn’t. When his zip was as far down as it would go, he reached inside and pushed away his briefs, grabbing his cock just as he had done countless times before as he prepared to pee. It came out with his hand and hung down in front of him as he let go.

“Wow.” Gemma said as she watched him. “Can you believe we’re actually doing this?”

Brad felt the first twitches of the inevitable erection as she examined him with eager eyes. Trying to avoid the awkwardness of a hard on, he encouraged her, “If you just want to hold it and point, I’ll start whenever you like.”

With an uneasy edge to her movements Gemma reached out and gently took his flaccid member in her hand while Brad shuffled a little closer to the target. Her fingers felt warm on him and even though her movements were minimal, he felt the familiar heat of a hard on rising faster than he was comfortable with. It required a monumental piece of self-control to relax enough to start the stream of water that at first spat and then flowed easily from the end of his now semi-hard cock. Brad gave a huge sigh of relief as he drained.

“It feels amazing.” Gemma couldn’t take her eyes off Brad’s cock as she gently pointed the stream around the urinal, exerting her control. At first she thought he was just going to get hard, but when he started to urinate she put the enlargement down to the urination. “It’s like I can actually feel it flowing through. Cool.”

Brad closed his eyes, enjoying both his own relief and Gemma’s delight. As his stream subsided he opened them again to find Gemma smiling down at his cock, still firmly in her hand as she shook the last drops from him. She looked up, beaming at her handiwork but not letting go of him yet. The innocently delighted look on her pretty face got to him and this time there was no stopping the sensation as he started to twitch in her hand.

“You know, if you keep holding me like that… well, I’m going to get all excited.” His tone was almost encouraging her to let go, something she showed no signs of doing.

“Really?” She looked down at his hardening cock. “So cool. Do you mind if I watch?”

Brad shook his head and gave a short laugh. It wasn’t like there was a whole lot he could do. “Sure. Enjoy.”

Gemma’s hand didn’t leave his cock as it continued its rise. Brad felt the softness of her fingers keep him wrapped as he got bigger, tight enough to feel the change in him but not restrict his hardness in any way. Once or twice he thought he felt a small movement from her like she was starting to stroke him, but all she was really was feeling along his length as he hardened. He looked down and watched as he twitched again and again in her hand, each time rising a little more.

When he was fully hard and standing straight up from his zipper, Gemma used both of her hands to gently trace the sides of his cock and around the head. He suspected she knew what she was doing, but whether she did or not, it felt great.

“Wow.” He could hear the smile in her voice. “That was great. I’ve never watched that before. It was great of you to let me see. Does it feel nice?”

“Sure does.” Brad nodded. “I think your hand had something to do with that though.”

“Oh, sorry.” Gemma pulled away her hand. “I didn’t mean to torture you. You’ve been so nice to me and all.” She looked up at him and smiled, a little awkwardly this time. “Look, I don’t what you to think I’m slutty or anything, but, you know, since you’ve been so nice to me, maybe you’d like me to… you know, take care of that for you?”

Brad managed not to grin as he replied, “Well, now that you mention it… that would be nice. This whole thing has really turned me on.”

“Me too.” Gemma admitted as she knelt down to take hold of him again. “I started to get all flushed when you were getting hard. That made me so horny, watching you get up.” She started to unbuckle his belt without asking and then pulled away his pants and briefs. As his cock sprung up higher than ever, Gemma allowed her hand to slip under him and feel his balls. “These feel pretty full, probably could do with losing a load.” She laughed as she began stroking him long and slow.

“Probably.” Brad swallowed as the feeling of her attentions started to run around his body. “It was awesome, you holding me like that. There was nothing I could do to stop getting hard. I just kept thinking about what you would look like without that dress.”

Gemma looked up from his cock and a wicked look crossed her face. “You want to see?”

Brad had barely nodded when she reached around for her zipper and pulled it down. Facing him, she eased the dress off her shoulders and let it slip down to her waist to reveal a black lacy bra that held up a lovely pair of boobs. Then she eased the dress over her hips and down to her feet, this time letting Brad catch his first view of the tiniest black g-string he had ever seen. She looked gorgeous.

Brad was about to say so when she took a step towards him and started to pull away his shirt. Moments later he stepped out of his pants and was naked in front of her. He reached out and touched her breasts one after the other while Gemma fumbled with the catch of her bra and let it fall away. Her nipples were already erect and pushing straight out from her pert breasts. He reached over and placed his whole hand around her breast, moving his palm over the nipple and squeezing her.

Gemma had taken hold of him again and was now pumping his hard on steadily while he played with her boobs. She eased out of his hold and got back down on her knees in front of him, holding his cock between her hands almost like she was worshipping it. “I’ve been dying to do this ever since I saw it.” She quickly took the head of his cock into her mouth and started sucking hard. Her tongue ran over him eagerly, around the rim and all over the head while he closed his eyes and enjoyed the sensation of the best mouth that had ever tasted his cock.

There was no doubt Gemma knew what she was doing now as she held him firmly in one hand, sucked and licked on him, eased her mouth up and down on him and squeezed his balls gently with her other hand. Taking her mouth off him for just a few seconds, she wrapped her arms around him to grasp his ass cheeks while she flicked her tongue all over the head of his free-standing cock. In between licking him, she started to take the tip back into her mouth again and let her tongue caress the smooth skin of his cock’s head. Each time she withdrew, she did it slowly, making sure she created lots of sensation around the rim as she did. It was beginning to drive Brad wild.

“If you want me to come in your mouth, it won’t be long now,” he breathed. “But if you’d like me to give that hot little pussy of yours some attention, why don’t you let me have a look?”

Without saying a word Gemma took her mouth off him and started to slip her g-sting off. When it joined the rest of their clothes on the tiled floor she turned away from him and bent over as far as she could go, opening her legs and offering him his first view of her pussy from the rear.

Brad gave her ass a playful slap as he stooped down to get a better look at her pussy. He reached between her legs and parted her lips with his thumbs. As he revealed more than a hint of pink he heard Gemma gasp and he slipped his forefinger deep into her soaking hole.

She knew she was going to come as soon as she looked down through her legs and saw his hard cock wobbling in front of him as he knelt to look at her. Feeling him open her lips and probe her, knowing he was watching every little detail while he did so, she felt the familiar tensing that prefaced her orgasms. When she realized that she had never climaxed as quickly as this before, the whole incredible encounter took control and exploded all over her body.

Brad was surprised to feel her pussy contract so quickly after he started to explore her, but as soon as he did he let his finger find her clit and slowly massage it as she came. At first all he felt was the gripping of her pussy on his finger, but then she lifted her head a little and almost shouted through her panting, “Oh fuck.” She came back down, her hands resting on her shins while he massaged her pussy.

Still breathing heavily, she slid to the floor and turned to face him, immediately reaching out for his cock and starting to stroke it. “I have never come that quickly.” She beamed. “Never ever. But I have to ask you one more favor now.” Gemma gently started to lie back on the floor, pulling him by the cock to join her. “I want you inside me. I’ve enjoyed seeing that cock tonight, but now I want to feel it.”

Gemma’s face had turned from the pretty party-girl of earlier in the evening, to the raw look of a wanton passionate woman, desperate for his cock. Brad looked down at her eager face and wonderfully tight body as she drew him to enter her. She was so wet and swollen with excitement it took no effort to slide into her, deep and long. Brad hardly had time to savor how the inside of Gemma felt warm and tight when her hand started moving over his back and buttocks, encouraging him to pump into her.

As he worked up his rhythm, Brad glanced at Gemma’s face, lost in a trance of pleasure as he rode into her. He tried to bite her nipple as he moved in and out but only managed to suck on it with the movement of their bodies. Looking down between them and seeing his cock disappearing time after time into her pussy was the last thing he saw before his climax began taking over him.

Gemma had never felt a guy who used his cock as well as Brad did. He had eased up from her on his arms and was varying his strokes into her, sometimes fast, sometimes long, the feeling of not knowing what he was going to do next was blowing her mind. He was trying to take her nipple in his mouth each time he withdrew his cock and now he had slowed up and was tensing and grinding hard into her pubic area, teasing his orgasm as high as he could and bringing her closer and closer to a second.

She heard a gasp from him as he made another deep thrust and knew she was about to be flooded with come. For five or six long, slow, thrusts Brad spewed hot fluid deep into her. She watched his face contort with pleasure as his body unleashed its pleasure and felt his legs shake, wringing the very most out of this moment.

As Brad collapsed on top of her, Gemma started to feel the juices oozing from her pussy. She smiled at the thought of his beautiful cock, his full balls and the delivery they had just completed. She could feel herself close to another climax though and eased herself out from under him. Not wishing to ask for any more favors, she reached down and started to finger herself as Brad sat up next to her.

She had never ever masturbated in front of a guy before, but the heat of the moment had her lost as she started to unashamedly pleasure herself while Brad looked on. She had one hand pulling on her nipple and another buried deep in her pussy when he offered to help. “Here, let me do that.” Brad let her continue to massage the inside of her pussy with her fingers but took over rubbing her clit.

“I’d like to see you come again,” he encouraged her. “You’ve been watching me all night, watching me get hard and getting me so hot for you. Now I’d like to see you come again.”

Gemma didn’t need any extra encouragement as she was already feeling the start of her climax work towards her fingers from deep inside her pussy. “Oh God, this has been so incredible. No one’s ever made me come like this.”

Her face was blank and lost as Brad felt her stiffen against his fingers and her breathing become a series of short pants and grunts as she came for the second time in only a few minutes. “Oh my.” She brought her other hand down to press harder on his hand as it worked her clit as her orgasm gushed from her again.

She fell against his shoulder when the moment subsided, their naked bodies alive but tired from the intensity and never noticing the cold tiled floor they were on. Gemma was smiling and shaking her head after the most incredible experience of her life.

Brad was grinning as he helped her up and they stared to gather up clothing. Gemma was still breathing heavily as she dressed, looking over as Brad tucked away his beautiful cock. “Well, I guess I know all about what happens when you hold a guy’s dick while he’s peeing now… and a bit more besides.”

“I guess you do.” Brad pulled up her dress zipper for her. “I hope the dare was worth it.”

“Definitely worth it.” Gemma leaned over to brush her lips against his. “Now all I’ve got to do is think of a reason we’ve been gone so long. It’s not like I can tell my sister I let her boyfriend fuck me.”

Brad froze half-way up his shirt buttons. He looked over to Gemma again and saw the resemblance that he had dismissed as familiarity earlier: how could he have missed it? He’d never met Ashley’s sister because she had been away at college, due home any day…

“You mean… you’re…”

“Ashley’s sister. Yes.” Gemma looked unfazed by the revelation. “It was Ashley who dared me to ask you. She was hiding when I came over to you. She thought it would be funny, and I don’t think she thought I would go through with it. Or that you would for that matter!”

“Yes,” he started to recover and wonder what he was going to say to Ashley, “mind you, it turned out to be a lot more than funny.”

“Yes.” Gemma smiled at him. “It turned out to be the best fuck of my life.”

Despite the new problem he’d been posed, Brad couldn’t find a reason to disagree with her.


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