*This is a retelling of my husband's first experience with two women. He was just out of high school, long before we met. I love this story and have changed the names (of course) and a few details, but this is pretty close to how my husband recounted the events to me. It's his story, in more ways than one. There is quite a bit of non-sexual background to it, and I include it because I just think it's a great story and I hope I don't lose too many of you while I tell it. The sex at the end gets me hot and I hope it gets you as hot as it got me the first time he told it to me! Oh, and everyone involved is 18 or over.*
A little background-
Jack grew up in a small(ish) Texas town, not exactly in the middle of nowhere, but "you could see it from there". He lived with his paternal Grandmother from the time he was about 12 for reasons we won't take the time to go into here. His grandma lived right on the edge of the rough side of town, and Jack went to school with the kids from the trailer parks and the barrio. He was a bit of a jock growing up, mostly because his grandma made it clear he was not going to be running around with nothing to do ("Idle hands do the devil's work!") and he'd rather spend his time playing football and baseball than working with his uncle hanging drywall or pouring concrete after school. He was an above average player on both teams and was relatively popular as a result. Jack was an independent spirit and his grandma encouraged him to think for himself, but also made sure he steered clear of the kind of trouble that was always available to young men with wild hearts on the "bad side" of town. As a result, he had few close friends and he found himself stuck firmly between the popular rich kids (mostly white) and the poor kids from his neighborhood (mostly Hispanic). He was friendly with kids from both sectors, but not really in deep with either group.
With that out of the way, let's get started-
1986- Mr. Jacoby's civics class, October
Jack walked into civics class and immediately his eyes were drawn to Roxy and Darcy sitting at their usual spot near the back corner of the room. He tried to be covert but he had not yet developed the skill of being able to steal a look and not get caught in the act. He turned and saw Roxy's impressive cleavage evident in her blue denim top. Roxy was a tall (5'9") redheaded Latina with full pouty lips and a body that Sir Mix-A-Lot would help popularize a few years later. She was leaning over the back of her chair talking to her best friend and partner in crime, Darcy, a shorter (5'2") Anglo hottie with feathered hair who was also nicely endowed with a smaller frame, and the lean created a very nice shot of Roxy's cleavage. Jack caught sight of it and stared directly into it, mesmerized. A moment later, Roxy noticed him noticing her tits and made him pay for it.
"Hey Quarterback. Like the view? Like my chi-chis?" Roxy asked loudly in a sexy, teasing voice while pushing her tits together, pushing them out of the front of her tight buttoned up shirt even more.
Darcy and everyone else already in class turned to look. Jack turned red and proceeded to his desk in the next row and two up from the girls as quickly as he could, but the laughter started and Roxy had all she needed to torment the good looking football player.
"Your cheerleader girlfriend ain't got a rack like this one, eh Quarterback?" Roxy teased in her thick Mexican accent. 'Quarterback' was pronounced with every syllable getting maximum attention. Jack would never admit it but he thought her accent was sexy as hell.
Darcy chimed in. "Shit Roxy, she'd give herself a black eye if she tried some of those cheers and jumps with balloon boobies like yours!"
More laughter followed in the class and Jack had to smile.
"Shut up Darcy! It ain't like your titties don't bounce all over when you do jumping jacks in PE!" Roxy said, punching Darcy in the arm.
Jack laughed out loud and the girls both focused their attention to him.
Roxy turned and looked forward towards Jack. "You like watching us during PE, huh Quarterback? In our blue shorts and tight shirts?"
Roxy emphasized 'tight' and pursed her full lips and blew Jack a kiss. Darcy raised her arms and leaned back in her chair, making her ample breasts strain against her Judas Priest t-shirt, and gave Jack her best video vixen look. Jack turned forward and shook his head in disbelief.
"Ohh" Roxy moaned in disappointment "c'mon Quarterback, don't be that way."
Jack stayed looking forward, feeling his face heat up.
"Those jocks are such teases." Darcy said.
"You like to tease us Quarterback?" Roxy asked.
"I'm not a quarterback Roxy. I play linebacker." Jack corrected.
"Odelay! Quarterbacker, Linebacker, Asscracker, whatever!" Roxy replied.
The class erupted in laughter and that is the moment Mr. Jacoby walked into the room.