After our Mario kart dare ended with Jill and I hooking up for the first time, calling each other up to fuck or full around became a part of our daily schedule. One day while I was in class I got a text from Jill telling me to meet her at the park where we play tennis and to bring my gear. As I was typing a response she sent me a video with a message that said, “I bet you won’t open this in class. P.s. Make sure you have headphones in before you hit play.” She ended her text with a winky face, and as soon as my professor turned his back I slipped one of my headphones into my ear and hit play.
Jill was sitting completely nude on her bed filming herself in the mirror that hung on her closet door. She gave a sexy wave and wink and then began reaching for something just out of view of the mirror. Within seconds she had her tennis racquet in her hand, and it was obvious that she had put a brand new white grip on her handle. My cock started to stiffen as she placed the base of her handle at her wet entrance and she let out a shuttering moan. Suddenly the video cuts off and I was left rock hard from the short video.
A few minutes later, to me it felt like hours, my professor ended his lecture and everyone shot out from their seats in a hurry to leave the lecture hall. I ran to my dorm and slung the door open to find my roommate, Rocky, hanging out on his bed typing away on his laptop. Rocky grew up in the same town as Jill and I, and we’d been great friends for as long as I could remember. Growing up people always thought he was my younger brother because we looked so much alike, the only major difference between us was that he was about five inches shorter and a bit leaner than I was.
He glanced up at me from his homework and said, “You look like you’re in a hurry.”
“I’m on my way to meet Jill,” I said as I peeled off my jeans and threw on a pair of shorts.
“Looks like you can’t wait,” he chuckled as he nodded towards the obvious tent I was pitching in my boxers.
“Shut up,” I laughed back, “you’d be the same way if you got the same video as I did a few minutes ago.”
“What the hell is that supposed to mean?” he called out as I hurried out the door.
Fifteen minutes later I was on the court with Jill ready to play ball, and ready to get back to her place where the real games would begin. “How’d you like the video I sent you?” she asked while she dug around in her bag. Before I could answer however, she pulled the same white gripped racquet from the video out of her bag. She looked down at my crotch as my dick began to twitch from the memory of her inserting the handle into herself. “Apparently you liked it quite a bit. How about we place a little bet? If you win I’ll let you watch me fuck my racquet live, but if I win then you have to suck my toes when we get back to my dorm, before I take a shower.”
“Whatever you say, but I promise you right now, there’s no way I’m going to lose.” We started playing and it wasn’t long before Jill had accepted her defeat.
“Holy shit. I don’t think I’ve ever seen you play so well before. Where the hell were those skills when we were still in highschool?” she said panting.
“I told you there was no way you were going to beat me today, so about that bet-.”
” I know,” Jill said still out of breath, “let’s go so you can claim your reward.”
“No.”
She looked at me confused by my response, “What do you mean know? I thought you wanted to watch?”
“Oh I’m going to watch you,” I said, ” but we’re not going anywhere.” Realization dawned on her face as she comprehended what I was saying.
“No way! We’re in a public park and there are people around!”
“So? You never said where I was going to get to watch you.”
Jill looked at me, and finally a smirk formed on her face, “Fine, but I’m not taking my tennis skirt off,” she said as she lowered herself against the net post. She moved her hand down and pulled her skirt liner to the side. She looked around one more time cautiously before reaching for her racquet that was set against the net next to her.
She carefully positioned the handle at the entrance to her pussy and slowly inserted her grip into herself. Jill let out a muffled moan as she began to slowly move the racquet in and out of her self. “Fuck!” she breathed as wet sloshing sounds mixed with her panting.
She began to pickup the pace and one of her hands reached up towards her breasts. Her nipples, hard from her arousal, stuck out visibly from her sports bra. She opened her eyes for just a second and glanced around to make sure nobody was watching, and then in one quick motion she pulled her bra up letting her beautiful tits bounce freely. She began to pick up the pace as she worked the racquet while her other hand pinched and twisted her hard nipples.
“Fuck! I’m cumming! Oh fuck! Oh fuck!”
“Oh fuck!” I heard from behind me just as Jill began to convulse, a large wet spot beginning to form underneath her.
As I whipped my head around, I saw Rocky standing no more than ten feet away from us.
Source: reddit.com/r/sexystories/comments/r68uww/mf_highschool_teammate_turned_fwb_in_college_part