Losing Virginity To Each Other

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Middlewomen sets up crush's first time together.
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Prologue

"Relax Megan!" Jamie said for the third time since she had turned on her computer. "We're over 18, we can see this." Jamie and Megan were having a sleepover at Jamie's house while her parent's were in Mexico on their wedding anniversary trip. So far in the three hours they had been together they had broken half of Jamie's parent's rules. No porn, no alcohol, and no pillow fights! Already they were down to their soaked panties as they watched a porn video on the internet. Jamie's 35C cup breasts could be seen through her white bra as she stroked herself. Megan stopped to lick her fingers clean and to turn up the volume. "UUGGGHHHH!" suddenly startled Megan turned to see Jamie climaxing on the white carpeted floor. It was too much for her and she let out a loud moan and climaxed as well. Afterwards Jamie jumped to her feet and her breasts bounced up and down like soccer balls as she went to get towels to clean up their messes.

Ben laid his head on his pillow as he fantasized about Megan, his crush of which he had since eighth grade. He stroked his large cock as he imagined her stroking it for him. With her red hair falling over her perfect breasts she squealed with delight as he moaned and sent a stream of cum flying at her face. "OHHhhh." He let out a quiet moan as he cummed. He had been looking for the right moment for him to ask her out for the past two years now, but had never had the nerve. Truth be told he was scared of being rejected by her.

It was December and the winter break was only a day away. Of course, nobody could focus on schoolwork since it was the last day of school before break. Even the basketball team, of which Ben was on, had trouble focusing on the game. The cheerleaders, Megan and Jamie, were both present at the game in their cheering outfits which showed their perfect bodies magnificently. This game could make the team undefeated for the first time in a decade. At half time the score was tied 43-43. As the cheer team went onto the court, Ben couldn't help but stare at Megan and Jamie. Both of which he liked, but Megan was the one he wanted. "Hey, Ben!" One of his teammates yelled next to him. "Are you staring at Jamie and Megan again? Just ask one of them out!" he added in a quieter voice.

"No, I'm not staring at them!" Ben replied quickly trying to hide his embarrassment and the bulge in his shorts.

"Whatever, deny it if you want." His teammate replied as he shrugged. The second half started and Ben was put in for the last ten minutes. By then, they had lost their lead and were five points down from winning. Within eight minutes they had gained a one point lead. Then the opposing team swished a three point and now had the upper with less than thirty seconds to spare. Ben passed the ball and waited for a pass at the top of the key. It came and in the final moments of the game he swished his three point shot to win the game. To Ben's ultimate delight his two favorite cheerleaders came running up to him breasts bouncing like the ball he had been holding.

After the game Megan and Jamie changed in the girl's locker room. "That was an incredible shot Ben made wasn't it!" exclaimed Jamie with a dirty grin.

"Yes, it was wasn't it." Megan replied with a worried look on her face. "What are you planning?"

Oh, nothing. It's just that I think HE deserves a special award." Jamie said. Megan's eyes widened and her breasts perked up as Jamie told Megan her plan.

Later on that day Ben received a call from Jamie asking if she could come over for a study date. Ben's parents had just left for a convention in Las Vegas so he said ok. To Ben's surprise Megan showed up in a miniskirt and a very revealing top. Ben felt his member begin to rise as she walked in and said that Jamie was coming over soon, but had said to go over now. It was all Ben could do to hold his member in when she bent over and gave him a very nice view of her panty covered ass. "I'll see you upstairs." She said sexily as she swayed her way to the top of the stairs. Ben was knocked out of his dream state as his doorbell rang again. Answering it he found Jamie dressed down to very, very short cutoffs and a nearly see-through tank top that was two sizes too small for her. With her dark brown hair down around her breasts she looked a goddess.

"Sit." She ordered as she began to unbutton his shirt.

"What. What are you doing?" he gasped as she sat into his lap and leaned back to let him see her braless breasts. He gasped. Pulling Jamie into his lap he looked into her eyes and they gave him all the confirmation he needed. He pulled off her tank top and as her breasts fell back into place he began to fondle.

Suddenly a thump upstairs made him turn to look toward the stairs. Poking her head and partially covered body out of Ben's parent's bedroom Megan wagged her finger for him to follow. He, of course, followed and so did Jamie with a sexy grin on her face. When Ben turned the corner into his parent's bedroom he saw his fantasies come true. In his parent's bed was Megan wrapped over in the covers with her 35D cup breasts barely covered. He felt his pants being undone from behind as Jamie pulled his pants down to reveal a fully ready 11 inch cock. He heard a gasp from Megan. Ben had forgotten that Megan was also a virgin and that this would be a special night for all three of them. Jumping into the bed he pulled the covers down embraced Megan in a long, passionate kiss before she bent down and began stroking his cock. Jamie leapt onto the bed from behind and he fondled both of their breasts, one with each hand. He was in heaven.

Five minutes later Megan was lying under him. "Are you sure?" he asked again.

"Yes I've wanted you ever since we first met. Now put that into me." She squealed. Ben was only too happy to comply. Pushing his cock his met her resistance and she nodded slowly and he pushed ramming all the way home. His cock was in heaven and only a sharp moan from Megan could be heard as she felt herself being stretched by a real cock.

"OHHH GOD YES...BEN ...YES...KEEP GOING...I'M GOING TO CUMMM!!!!!!!!!...." Megan gasped and yelped. Ben increased his speed and gasped as he felt his cock begin to convulse. He was cumming. He was cumming inside his crush's pussy. His dreams come true. Megan was thinking the same thing or something along the same line as she began to scream, "OHH GOD YES...I'M CUMMING...DON'T STOP....YES...YES...YES!!!!!!...." Ben collapsed into her breasts as he recovered from such a terrific climax.

Jamie moaned and then gasped as she climaxed from masturbating while watching them. "That was incredible." She simply stated. Megan was smiling and kissed Ben again.

"Do you think you can still satisfy Jamie too?" Megan asked while glancing down at the cock still buried in her.

"Come here Jamie." He said as he pushed her into the same position as Megan next to her. "OK, ready." Her eyes and pussy were enough. He rammed home yet again. Savoring that these two gorgeous women were with him.

"I'M CUMMING...DON'T YOU DARE STOP....FUCK ME...FUCK ME....!!!!!" Yelled Jamie as she convulsed. Ben fell between the two fucked women and laid his hands across them. "That was incredible." Both of the eyes moaned. It was there they fell asleep. Each satisfied and well ready for round two.

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