Day 6: Friday-Night Date With Debbie
Just before Jimmy knocked on Debbie’s apartment door, he thought, No way around it: Dinner and a movie are gonna cost me fifty bucks tonight. Which isn’t cheap.
This idea was underscored when Debbie came to the door. She was wearing a fancy blue dress, jewelry, and fancy high-heeled shoes.
Jimmy sighed. Make that sixty bucks that I’m going to be spending.
Debbie looked great in her fancy clothes. This was mainly because by Friday night, Debbie had perfect, waist-length hair, and Debbie also had the body of a dance instructor.
But two things were out of place with Debbie’s outfit. Debbie had black hair and olive-dark skin, so usually she wore dark makeup—but tonight her lipstick and nail polish were both fire-engine red. Jimmy didn’t spot the other thing till she started to walk next to him—
Jimmy exclaimed, “You’re not wearing a bra!”
Debbie gave Jimmy a sexy smile. “Yeah, I feel a little racy tonight.” Then she asked with a worried expression, “Is that okay? Going braless?”
Jimmy sighed. “Sure, Debbie, that’s fine.” Make that seventy bucks or higher.
Debbie stopped walking toward Jimmy’s car. When Jimmy stopped walking and turned to face Debbie, she took his face in her hands—
“Is something bothering you? Please tell me.”
Fuck it. Be honest. “I’m a college student, Debbie. I’ve taken out student loans. I don’t have a lot of money. But you’re dressed for a New Year’s Eve party, and you clearly expect me to spend money tonight like it’s New Year’s Eve. I can’t. I’m sorry, maybe we should cancel the date.”
And then I start looking for a new girlfriend.
But Debbie surprised him. She walked right up to him, kissed him on the mouth, then said, “I don’t want to cancel our date.” She kissed him again. “I want to be with you.”
Then Debbie flabbergasted Jimmy: “Tell me what you want, and I’ll go along with it.”
Debbie did not sound sarcastic, so Jimmy got honest again: “How about ‘dinner’ at Jack In The Box, and we get the ‘movie’ at Grompet Video?”
Debbie smiled. “Ohmigod, that sounds like a plan.”
Jimmy offered to let Debbie change out of her fancy clothes. Debbie replied, “Do you like seeing me like this?”
“Are you kidding? You’re hot and classy both, Debbie!”
“That’s all I need to know,” Debbie said. She gestured toward Jimmy’s car. “Let’s go.”
Both the employees and the customers stared when Debbie and Jimmy walked into Jack In The Box. If Debbie was bothered by being way overdressed for the place, she gave no sign.
Grompet Video had Blu-ray DVDs for rent, no surprise. But Grompet Video had been around long enough that it also had (a few) Betamax videocassettes for rent. Tyudlurm University’s Film Studies majors kept Grompet Video in business, even after Blockbuster Video had gone bust.
Jimmy and Debbie had been in the store for two minutes when Debbie murmured, “See those two girls over there?”
One girl had pink hair; the other had blue. Pink Hair was trying to sell her companion on the genius of Quentin Tarantino—while smiling too much and standing too close. Blue-Haired Girl smiled and stood close, right back—while claiming that Federico Fellini ran rings around Tarantino.
Debbie asked next, “Do you think those girls are pretty?”
Jimmy gave the safe answer: “It doesn’t matter. I think they both play for the other team.”
Debbie said, “As I was getting dressed, the thought occurred to me: Since I care deeply for you, it’s selfish of me not to want you to get all the sex you can. Even when that means you fuck other women.”
Jimmy stared at her.
Debbie continued, “I don’t believe it yet, not in my heart. If you walked over and got those two girls’ phone numbers, I’d feel jealous. But I can’t say anymore that jealousy is right.”
“Let me see if I have this straight. You’re saying it’s okay with you if I’d fuck other women?”
“A little part of me says it’s okay if you enjoy other women. But most of me still says, Don’t you dare!”
“Gotcha. But let me know when that little part of you, the unjealous part, becomes the big part, okay?”
Jimmy thought he was making a joke, but Debbie nodded.
Jimmy let Debbie pick out the movie. She chose The Pitch-Perfect Games—
“Twenty-four teenaged singers compete in an especially brutal a cappella competition. The heroine volunteers to replace her sister, who has laryngitis.”
Back in Jimmy’s dorm room an hour later, the movie was playing, but neither Jimmy nor Debbie was watching it. They were kissing like the world was about to end.
What was especially amazing to Jimmy was that Debbie was not trying to control Jimmy’s groping and caressing of her bra-free tits through her dress. Instead, Debbie was moaning through the kiss.
It was Jimmy who eventually broke the kiss.
“Wow,” said Debbie, “I am so much enjoying kissing you.”
“I guess so,” Jimmy replied. “Your face is pink.”
Debbie looked down. “I’m not the only person here who’s having fun.” She was talking about Jimmy’s hard-on.
Jimmy smiled at her. “Let’s see if you’re having fun too.” His hand slid up her thigh.
Jimmy expected for Debbie to slap his hand away, but she did not. Seconds later, Jimmy found a possible reason why.
“Whoa,” he said, “you are really wet.”
Debbie did not respond with words. Instead, she grabbed the back of Jimmy’s head and mashed her lips against his.
Debbie moaned, while she kissed Jimmy, while Jimmy fingered her.
Jimmy ordered, “Tell me what you want, Debbie.”
“I want ... I want—I don’t know what I want! I want you to fuck me, but that seems so selfish! I should be giving you what you want!”
Jimmy said, “I want to fuck you too. But first, I want to get you naked. Stand up.”
Jimmy got a surprise when he got her dress off. Gosh golly, but Debbie was wearing a garter belt and stockings inside her panties!
Jimmy did not hurry at taking Debbie’s panties off. He spent a lot of time licking and stroking her bare tits, and sucking on and pulling on her nipples. Debbie moaned.
When Jimmy slid his hand inside Debbie’s panties and started to finger her, she started to thrust her hips against his hand. She was still hot and wet.
She murmured, “Oh please, oh please, I need you to fuck me, oh please, I’m yours, oh please...”
Jimmy said, “Then I guess I should get undressed, huh?”
Debbie grinned. “I’ll help!”
Not quite a minute later, Debbie was pulling Jimmy’s tighty-whiteys off. Jimmy’s throbbing, twitching cock was exposed to the air.
“Oh my,” Debbie said. “Can I?”
With no more encouragement than this, the same Debbie Smith who had many times gone Full Diva over Jimmy’s one request for a blowjob, now sucked his cock like a drunken sorority girl. Debbie’s mouth got him happy, then she got him hard, then—
Jimmy expected Debbie to stop the blowjob once he was hard enough to fuck her pussy. But Debbie kept going.
“Debbie, I’m going to—I’m going to ... oh god.”
Jimmy came in her mouth, and it was glorious—until she pulled her head off his dick and looked around in a panic. Soon she was eyeing the stack of paper towels that was by the dorm-room sink.
Jimmy knew, to five decimal places, what she was thinking.
“Gosh golly, Debbie, forget spitting into a paper towel. Get back on my dick and swallow me!”
Amazingly, that was exactly what Debbie did next.
She swallowed him as he came. She kept sucking him till he got semi-soft, then she sucked him some more till he got hard again.
“Stop, Debbie. I’m gonna fuck you now.”
Debbie stopped the blowjob and lay down on Jimmy’s bed. Her pussy was slurpy-wet when Jimmy fucked her.
Debbie screamed into his shoulder whenever she came. Many times.
Just as with the blowjob, pistoning Debbie was glorious for Jimmy; his dick felt million-dollar tingles for a long time.
It was the perfect end to a $13.68 date.
It was, by far, the wildest sex session that Jimmy had ever had with Debbie Smith. But compared to what happened later with Debbie, this was like a “date” of Jimmy dancing with his great-grandmother’s roommate in the retirement home.