Jack had been driving kids to a number of different social events in the affluent suburbs outside of town for about 6 weeks now. The goodwill he had made from the first few times he had hooked the guys up with a motel room, coupled with the $20 referral bonus, had given him some great opportunities to enhance his private porn collection. Plus his boss liked the extra hour or two of limo time he was able to bill to the parents. Aside from the initial straight fuck video he had taken of that first couple, Mike and Katie, he had added another regular fuck, a couple giving each other oral and even an anal session with a young girl who claimed she was only allowing her date to fuck her in the ass because she was "saving" herself for marriage! But tonight's fare was starting out to be one of the stranger ones that he had taken.
Normally it was the guy that came up to him and told him he had gotten Jack's name from someone and could Jack hook him and his date with with a room for a while. But tonight it was the girl that approached him. She was certainly pretty enough, although she seemed a bit more muscular than he liked, but the dress she wore was totally hot. She had on a short pink strapless prom dress that contrasted nicely with her deeply tanned young body. Following behind her, almost like a puppy dog, was this nerdy looking boy, wearing a wrinkled suit that looked a size too big on him. She walked up to Jack and announced "Hi. I'm Grace and this is Ian. I guess you must be Jack. I've heard how much fun the other kids have had with you as their driver." Jack was a little startled at how forward Grace was and wondered how a kid like Ian ever managed to snag her as his prom date. Grace handed Jack a small bag and asked if he could hold onto it for her for later - you know when she and Ian were alone. Ian seemed a little intimidated by Grace's comments, but he flashed Jack a weak smile then stared at Grace as she got into the back of the limo. Jack was able to see Grace pulling her dress down, but it was clear from the astonished look on Ian's face that she had flashed him. Ian stumbled into the back seat and Jack closed the door, then put the bag in the trunk and didn't think much of it at the time.
When that got to the dance, Grace told Ian to go inside and get them something to drink because she needed to talk to Jack about the "arrangements for later". Ian nervously walked away, glancing back at Grace time and again, as it he still couldn't believe he was at the prom with HER, which left Jack wondering again what the heck was going on. This was not your usual boy-girl pairing. Jack was honestly wondering if this kid was some kind of savant in the bedroom - putting all his book smarts to use to get laid. But his train of thought was interrupted when Grace asked Jack if it was OK if several friends joined them tonight. Grace's question shook him a little. Was this going to be some kind of sexual double date - two fucks for the price of one and was he going to get them both on tape? Jack thought about it for a little bit and the business man in him took over. He said "Yeah. Sure. But it will cost you a little more for the extra people. How about another $50? And, of h yeah, I still gotta check it when you are done to make sure nothing get damaged - I mean with the extra people partying in there.". It seemed almost sinful to him to get paid for making those special videos for his collection, but Jack thought "Why not - this way she thinks that the room is legit."
Grace giggled and said that she was sure she and her friends would be willing to pay the extra as long as all of them were in on tonight's festivities. There was something in the way she said it that made Jack wonder what she meant, but by the way Grace talked, this sounded like a VERY interesting night ahead. Grace said she would have the extra cash when Jack came back to pick them up later. When he asked if she needed anything else for the evening - drinks, munchies, condoms - she just laughed and pointed to the trunk. "Whatever I need is in the bag I gave you. Just make sure you don't go into it before we get to the room. If you can keep your hands out of it, maybe I'll show you some pictures afterwards." Jack just smiled, nodded, and uttered the single word "OK". He did not want to let on that he would have way more than just a few pictures from tonight's activities when the night was over. He could keep his curiosity in check until later when he could watch the drama unfold.
Normally it was the guy that came up to him and told him he had gotten Jack's name from someone and could Jack hook him and his date with with a room for a while. But tonight it was the girl that approached him. She was certainly pretty enough, although she seemed a bit more muscular than he liked, but the dress she wore was totally hot. She had on a short pink strapless prom dress that contrasted nicely with her deeply tanned young body. Following behind her, almost like a puppy dog, was this nerdy looking boy, wearing a wrinkled suit that looked a size too big on him. She walked up to Jack and announced "Hi. I'm Grace and this is Ian. I guess you must be Jack. I've heard how much fun the other kids have had with you as their driver." Jack was a little startled at how forward Grace was and wondered how a kid like Ian ever managed to snag her as his prom date. Grace handed Jack a small bag and asked if he could hold onto it for her for later - you know when she and Ian were alone. Ian seemed a little intimidated by Grace's comments, but he flashed Jack a weak smile then stared at Grace as she got into the back of the limo. Jack was able to see Grace pulling her dress down, but it was clear from the astonished look on Ian's face that she had flashed him. Ian stumbled into the back seat and Jack closed the door, then put the bag in the trunk and didn't think much of it at the time.
When that got to the dance, Grace told Ian to go inside and get them something to drink because she needed to talk to Jack about the "arrangements for later". Ian nervously walked away, glancing back at Grace time and again, as it he still couldn't believe he was at the prom with HER, which left Jack wondering again what the heck was going on. This was not your usual boy-girl pairing. Jack was honestly wondering if this kid was some kind of savant in the bedroom - putting all his book smarts to use to get laid. But his train of thought was interrupted when Grace asked Jack if it was OK if several friends joined them tonight. Grace's question shook him a little. Was this going to be some kind of sexual double date - two fucks for the price of one and was he going to get them both on tape? Jack thought about it for a little bit and the business man in him took over. He said "Yeah. Sure. But it will cost you a little more for the extra people. How about another $50? And, of h yeah, I still gotta check it when you are done to make sure nothing get damaged - I mean with the extra people partying in there.". It seemed almost sinful to him to get paid for making those special videos for his collection, but Jack thought "Why not - this way she thinks that the room is legit."
Grace giggled and said that she was sure she and her friends would be willing to pay the extra as long as all of them were in on tonight's festivities. There was something in the way she said it that made Jack wonder what she meant, but by the way Grace talked, this sounded like a VERY interesting night ahead. Grace said she would have the extra cash when Jack came back to pick them up later. When he asked if she needed anything else for the evening - drinks, munchies, condoms - she just laughed and pointed to the trunk. "Whatever I need is in the bag I gave you. Just make sure you don't go into it before we get to the room. If you can keep your hands out of it, maybe I'll show you some pictures afterwards." Jack just smiled, nodded, and uttered the single word "OK". He did not want to let on that he would have way more than just a few pictures from tonight's activities when the night was over. He could keep his curiosity in check until later when he could watch the drama unfold.