I Dare You

A moment later, her coffee arrived, and the waiter disappeared. She sat there, thinking about the evening so far. Well, this wasn't a typical weekend for her. She was definitely going to be sore in the morning. But she hadn't met Gail's dare. Too bad.

She must have had a sad look on her face, because the waiter wondered back, asking, "Everything ok, miss?". Shelli nodded, but the waiter asked if he could sit down. They started talking about the city, different people that came and went from the café, and just how quiet it was. His name was Bob. He was a musician, but working in the café helped make ends meet. They continued to talk, and Shelli realized they had a number of things in common. Including, interestingly, that neither were "attached".

"Look at the time!" he suddenly exclaimed. "It's 12 o'clock. I've got to close up and throw you out of here. Too bad."

"Ya." Shelli thought for a second. "You know any place we could go to keep talking?" "Everyplace around here is either closed or full up by this point at night," he replied. "We could have another coffee at my place, but I don't suppose you'd be interested in that. It's not like we've known each other for a while." Shelli was beginning to wonder if she wanted to get to know this guy. So, she said that she would be interested and they headed to Bob's place, just above the café, which was how he got the job.

They sat and talked. Eventually the conversation turned to relationships. Bob had had a run of bad ones, and figured that he was doomed to not finding anyone who wanted to get "close". Shelli certainly couldn't figure out why. He was good looking, interesting and wasn't full of himself. "I'd be interested," she said, before she knew what she was saying. Bob looked at her, a bit surprised she had said it as well.

Shelli was on autopilot by this point. She had pushed across the couch to kiss him, but ended up bowling him over, her landing on top of him. They both started to laugh, at which point Shelli said, "Let's give it a try". She planted a kiss on him that stated to boil his blood.

She remembered it all vividly, as Bob continued to lick at her. She was so enjoying this -- more so than any of the previous 4. Shelli's body began to shake from deep within. Lifting her head and arching her back, she tensed as she came. Bob pushed the dildo into her, helping her through the climax.

It was a strong, intense orgasm -- Shelli's pussy clamping down on the dildo. She screamed out, the feelings were so strong. But Shelli was also exhausted and as she fell back onto the bed, she also fell, almost immediately, to sleep.

It was dark when she awoke. Not being sure where she was, she came to with a start, sitting upright, breathing hard. Suddenly, she realized there was someone beside her. Then she heard Bob's voice, "It's OK. You fell asleep, so I figured you needed it". His arm eased her back to the pillow.

With that, Shelli started to cry. After asking and prodding, she told Bob everything: The dare, the other 4 guys, and the fact that she might like him. She figured she was going to be thrown out. But Bob just gave her a hug.

"So, one short, huh?" he asked. She nodded. After about 10 minutes, Bob said, "That's too bad. Can I try to make you feel better?" She rolled over and he kissed her on the forehead. But instead of having sex, he rolled out of bed and left the room.

Shelli rolled back on her side and lay there, wonder what was going on. But about 5 minutes later, she heard him come back. In the dark she thought she heard 2 sets of steps, but it must have been a mistake. She felt Bob get into the bed behind her, lifting her leg to gain access to her pussy. His rock-hard cock brushed up against her leg, as he guided it to her. "My turn to cum, now," he whispered. She was definitely game. Then he asked, "So, you want to finish your dare?"

Confused, she said, "I want you right now." With that, he pushed, his full hard-on sliding into her. This guy was not only long, but wide! He pushed twice, then slid his member out so his head was just touching her lips. "Put it back," she pleaded.

"OK, but I'm going to give you a chance to get me AND finish your dare, if you want. Don't be afraid, I had John come over. He's my next door neighbour. If you want, he'll stay. If not, he'll just leave." With that, he thrust back into her, and pulled out again.

"S,s,s,stay," she stammered. She could feel someone climb onto the bed in front of her, and felt a leg near her face. Reaching up, she found another mammoth cock, just inches from her. She wrapped her hand around it, and began stroking.

"Eat it," she heard, not sure which of the two men had said it. Shelli lifted her head and extended her tongue, running it along the bottom of the shaft. She worked her way from the end to the base of his dick, then back to the end. Just as she reached the end, he opened her mouth. Bob must have known what she was doing because he picked that exact moment to dive back into her pussy. She jammed her mouth forward enveloping John's cock. She'd never had to open her mouth so wide before.

As Bob continued to pound on her, he reached around and grabbed her tits. She knew that this was a recipe to make her cum. This caused her to quicken per pace on John. Each time she would dive down on him, then as she pulled back, her tongue would run over his length, finally swirling around the head of his dick, just the way Doug liked it.

Shelli started to cum, her body tightening up for the 6th time this evening. As it did, the muscles in her pussy clamped down on Bob's member, and very shortly afterwards, pushed him over the edge. Shelli had never felt anything like it. It was like a river being dumped into her. Bob's pumping started to slow, as he wrapped his arms around her.

But John's dick was as hard as ever. Shelli took one hand started playing with John's sack. After a while she started stroking John, even as she teased and played with his cock in her mouth. She knew what it was doing to him. She could feel it. He started to swell. Just as he came, she pulled him from her mouth, stroking him furiously - his juices spraying her tits and chin. She felt John lean forward, and kiss her on the forehead.

"Thank you," Shelli gasped.

"No, thank YOU," was the reply. John then disappeared into the dark. Shelli heard the apartment door close, and she knew they were alone. She went and cleaned the spray off of her, coming back to bed when she'd finished washing.

"So, did you like that?" Bob asked, snuggling up against her again.

"Oh ya"

"You want to see me again?"

"I'm not going anywhere right now," Shelli replied.

"OK," said Bob. "You know, we can do this alone, or you can have John over whenever you want'

Suddenly Shelli discovered she was glad she'd taken the dare. Not only had she found out she liked not being so selective, but she'd also found a guy to be with -- or two -- when she wanted! Gail was never going to believe this....or maybe she would!