With apologies to TexMan324 who suggested the theme.
All characters are 18 unless noted to be older.
Just a couple of days before senior prom, tight end (football player) Alan was naked and eating out Josie, his girlfriend and the “head” cheerleader in his bedroom. Alan’s best bud, and the team’s quarterback, Stan walked in on them. Josie, who had previously enjoyed “not-so-little-Stan” asked “big Stan” to join them on the bed, saying: “you know where to stick it.” Stan knew a really good place. But his idea of where it should go didn’t coincide with Josie’s, and after she came Josie decided she didn’t appreciate Stan’s appreciation of his tight end’s tight end. Causing her to storm off.
Didi, Alan’s 35 year-old “knockout” mom had just come home from grocery shopping. She passed the half-naked Josie rushing out. The upset teenager was getting herself dressed as she stumbled down the hallway and through the living room. Alan and Stan, who were both naked, stumbled out of Alan’s room pursuing Alan’s girlfriend. They stopped when they saw Didi.
“Don’t just stand there with your dicks in your hands, boys,” Didi said, “give me a hand with the groceries.”
As the two carried the brown paper bags into the kitchen, Didi– who was very perceptive and very supportive– asked Alan what was wrong. He told the story, and Stan added to the narrative the fact that they rented a limo– and three, Stan, Alan, and Marcie will be an odd number– Didi gently stroked “not-so-little-Stan” and asked if she could come.
“Now?” Alan asked, confused.
“No,” she said, continuing to stroke Stan’s stiffening rod, “to prom.”
“You’d… really… want… to?” Stan asked, slightly distracted by Didi’s touch.
“Sure,” Didi said, blowing her son a kiss, “I was too busy taking care of an infant to go to my senior prom.” Then she knelt.
“It would probably be best if Marcie was officially my date,” Alan said.
“Oh… ka… ay…” said Stan.
“Mrrumf,” was Didi’s reply.
After finishing off Stan, Didi French kissed Alan, and then went to change for her job as bartender at the Dew Drop Inn.
The next evening Marcie came over and Didi helped her “spice up her outfit a little.” Didi modeled a couple of cocktail dresses for Marcie, who chose a really skimpy one that showed off Didi’s more than ample cleavage. When the guys walked in after picking up their tuxedos, the dresses were in a pile sitting on the coffee table next to Didi and Marcie who were engaged in a happy soixante neuf on the living room carpet.
“Your mom is sooo cool, Alan,” Marcie said, her face shimmering with pussy juice.
At the dance, the four saw Josie, who had come with someone that none of them knew. Basically the only gal who hadn’t found a date two days before prom. By the middle of the evening, the four were dancing in a conga line while all the others were waltzing or watching. The chaperones were all drunk. Days later some thought, but weren’t certain, that they had seen Didi and her son swapping spit. Alan with his hand up his mom’s hemline playing with her ass.
If they hadn’t been playing grab-ass and joking about who was going to do what to whom and in what order the three teenagers would have seen a tear forming in Josie’s eye as they walked past her to share a joint with the “vice” principal in the parking lot.
On their return Didi whispered to Josie: “you can come too if you do everything that I tell you to.”
Josie nodded. After a little more dancing the five climbed into the limo for the ride to the hotel.
Didi had the limo stop at the Dew Drop Inn for a couple bottles. “Take off your underwear,” she said to Josie as they stopped.
“Here,” Didi said to the driver, handing him two pair of panties, “collateral, so you will be sure I’m coming back.”
As the driver was wondering what in the hell Didi meant, at Stan’s urging, Marcie gave the driver her panties as well. When Didi returned she had a small bag with two bottles and a pair of handcuffs with fake pink fur.
The five checked into the hotel, Josie with her hands cuffed behind her back. The clerk looked at the handcuffs.
“My son’s girlfriend,” Didi said, “I take being a chaperone seriously.”
The four teenagers nodded solemnly.
Taking the elevator up to the sixth floor, Marcie and Didi were kissing and making out with each other and undressing Josie in the car, then down the hallway to the ice machine and into the room.
A couple of minutes later the glasses were unwrapped, the bottles were open, and the tuxedos and dresses commingled in a big chair by the window. Josie was naked but still cuffed.
“I told my mom I’d call if I was out late,” Josie said, gesturing to the phone.
“Don’t worry, I’ll speak to her.” Didi said.
Marcie, sitting on Stan’s face, dialed and handed Didi the handset. Didi was riding her son’s shaft, as he idly toyed with Josie, as she spoke.
“Hi, oh… Just a silly teenage spat… We are all here at the hotel… No… Don’t worry Mrs. Greyson,” Didi said, sounding somber. “We have two rooms… I’m staying with Josie and Marcie and I won’t let any of them do anything that I wouldn’t do.”