by Jason Starr
So Andy acted like Mr. Gentleman at the bar, telling her that crap she seemed to eat right up, about how he just wanted things to “be cool” between them, and then, when he walked her home, he didn’t try to get any. Figuring he’d build up some more trust, he slipped her some tongue, and then, leaving her wanting more, he walked away. In the morning, at work, he decided to put some more points up on the scoreboard, and he e-mailed her some crap about how he’d had a great time with her and he was looking forward to seeing her again. He was bummed when she wrote back suggesting a double date. She obviously wanted her friend to check him out, and he didn’t feel like going on a fucking audition, especially with a girl he’d already cleared the bases with. He felt like if she had a problem with him, she thought he wasn’t good enough for her, then fuck her—let her find some dork who was willing to put up with that shit. But then, thinking about anal sex again, he sucked it up and wrote back that a double date sounded like a great idea. Then, figuring he might as well use this to his advantage, he decided to set her friend up with his roommate, Will the doctor. Girls always thought Will was really good-looking, and if her friend liked Will, it would score points for himself, increasing his chances for anal sex. Hey, it was worth a shot anyway.
Andy came up with a new Katie Porter game plan. He decided he’d keep up the act and go out with her for another two weeks, tops. If he didn’t score through the back door by then, it would be sayonara, baby.
On Monday he sent her an I-can’t-wait-to-see-you-again e-mail. Then, on Tuesday, he IM’d with her for a while, telling her how psyched he was about the double date and more bull like that. On Wednesday, Andy and Will—who was wearing his doctor’s scrubs—met Katie and Amanda at Katie’s place. Andy couldn’t believe how hot Amanda was. Katie had said, “She’s really cute,” but she was fucking smoking. She had a hot body, a pretty face, and had highlighted dirty-blond fuck-me hair. She was wearing a sleeveless low-cut top, exposing her muscular back, but it wasn’t too muscular. It showed she was nice and toned and was an indication that she definitely took care of herself. When Andy introduced himself and shook her hand, she smiled—she was wearing that shiny-type lipstick and her mouth was really sexy—and it bummed Andy out that she wasn’t his date, that he was stuck with nice, wholesome, boring Katie. He could tell that Will was into Amanda, too, just by the way he was acting, but when Andy and Will were alone in the kitchen, Will whispered, “Bro, she is so fucking hot,” and Andy said, “Yeah, don’t expect a birthday present from me this year, dude.”
They went to Mustang on Second and Eighty-fifth and sat outside. Andy had been on some shitty double dates where the two people who knew each other had to carry all the conversation and it was awkward and painful for everybody. But Amanda and Will hit it off right out of the blocks and actually did most of the talking. Andy, trying not to stare too much at Amanda’s great tits, was still jealous as hell. Meanwhile, Katie seemed pleased that Amanda and Will seemed so into each other. At one point, Katie and Amanda went to the bathroom together. When they returned, Katie held Andy’s hand and started rubbing her leg up against his and making goo-goo eyes at him. It was a total switch from the way she’d acted at the movie theater the other night. Andy figured that he must’ve gotten a good review from Amanda and, while, if he could’ve pressed a button and turned Katie into Amanda, he would’ve with no hesitation, he was glad that at least his strategy seemed to be working—Katie seemed to be totally into him now.
Like typical girls on dates, Katie and Amanda left their dishes—Santa Fe Chicken Salads—about three-quarters uneaten, while, like typical guys, Andy and Will wolfed down their burgers. Then, after splitting the check, they took the girls across the street for drinks at Molly Pitchers. They were still having their first round when Amanda and Will started sucking face. Katie was all over Andy, too. When Amanda and Katie took another bathroom trip, Andy and Will conferenced, deciding that the best move would be to get the girls back to their place ASAP. It was already past nine o’clock, and it was Wednesday, a work night. If they stayed at the bar much longer, the girls would start checking their watches or one of them would go, I have to get up early tomorrow, and the chances for getting laid would be KO’d.
Then Katie and Amanda came back and Katie said, “So how much longer do you guys want to stay here?” and Will gave Andy a look like, fuck, we blew it.
But then Andy said, “Come on, the night’s young, ladies,” and Katie said, “We know it is. But this place is kind of boring. Want to, like, go back to your place or something?”
A minute later, they were in a cab, heading uptown. Thank God, Andy’s other roommates were either out or in their rooms and the living room was empty. Of course the place was a wreck and Andy and Will made phoney excuses about how “it’s usually not like this” and said things like “sorry, our roommates are such fuckin’ slobs,” as they went around brushing crumbs off the couches and picking up as much garbage and as many beer bottles and soda cans as they could. The girls didn’t seem to mind the mess, though, and they started talking about how jealous they were that the guys had so much space and lived in such a nice, luxury building. Andy put on some Green Day and cracked open some brews while Will took Amanda for “the tour” of the rest of the apartment. Andy knew that once Will got Amanda into his room, they wouldn’t come out, and they didn’t. Andy and Katie didn’t bother drinking their beers, either, and Andy led her into his room, winding a tie around the outside knob to let Greg know that he was hooking up, and to spend the night someplace else.
Andy just wanted to rip Katie’s clothes off and get to it, and it was annoying as hell that she wanted to talk, going on and on about how great Amanda and Will were together and how glad she was that they had set them up. Andy tried not to let on how pissed off he was, smiling a lot and saying things like, “Yeah, it’s great,” and “Yeah, I know,” while waiting for her to shut the hell up and take her clothes off. Finally, she stopped talking and they were making out and he had her top and bra off and he was about to unsnap her jeans, when she said, “Wait, I want to tell you something else.” This time it was hard to hold back and he let out a frustrated breath and rolled his eyes a little.
“What’s wrong?” she asked.
“Nothing.”
“You just rolled your eyes.”
“No, I didn’t.”
“I saw you.”
“I didn’t.”
“Am I, like, boring you?”
“What? Of course not.”
She seemed unconvinced, but after he insisted that nothing was wrong, that of course he wanted to hear whatever she had to say, she started telling him some dumb story that Andy couldn’t really follow about how her boss had said something insulting about an outfit she’d worn to work the other day, and how she couldn’t stop obsessing about it. The whole thing sounded really stupid to Andy, like typical neurotic, insecure girl shit. Her boss, who was probably a cool dude, had made some passing comment and Katie was blowing it up, getting all melodramatic. But Andy knew he couldn’t tell Katie this. There was no faster way to put a bullet in a relationship—and to not get laid—than to not take a girl’s side in a fight. So Andy told Katie exactly what he knew she wanted to hear, that her boss was a jerk, an asshole, a fucking moron. “That’s great, tell me more,” Katie said, and Andy called her boss a prick, a jackass, a dickbag, a motherfucking shitface, and Katie was loving it.
“Thank you so much, I feel so much better now,” she said, and then she finally stopped jabbering and they started doing it. She got on top but was taking forever. Finally, she made some noise that sounded like she might’ve come, and that was good enough for him. He was kind of tired and was thinking about just coming quickly and trying for anal sex some other time, but then he figured he was here, he might as well give it a shot. He was going to suggest getting some Vaseline but, remembering all the times that had backfired for him in the past, he decided to try a different approach. Yeah, the Vaseline would make it more comfortabl
e, but mentioning that word “Vaseline” always seemed to do more harm than good. Maybe anal sex was something that girls liked to do, but didn’t like to discuss, and the less attention the guy brought to it, the better. Seemed logical anyway. So when they were about to do it doggy style, he figured he’d try to slip it in the other way, hoping she’d be totally into it. Although he wasn’t religious at all, he thought, Please, God, just this one time, and looked up toward the ceiling before he tried to enter her.
“Hey,” she said.
Fuck.
“What?” he said innocently.
“What’re you doing?”
He couldn’t tell—was she being, like, playful?
He decided to cut his losses, not take any chances, going, “Sorry,” like it had been an accident.
Later, while she was sleeping next to him, he regretted not trying to push the issue any farther. Maybe if he’d been playful back, said something like, What do you want me to do? she would’ve come back with, Whatever you feel like doing. Damn, he was such an idiot. Tonight might’ve been the night and he’d blown it.
Around sunrise, Katie woke him up. She told him how great last night had been and he told her he’d had a great time, too. He offered to walk her back to her place but she insisted on going alone, which was cool with him because he wanted to grab some more shut-eye.
“When can I see you again?” she asked at the door to the apartment.
“How ’bout tonight?” he said, thinking that there was no way he wasn’t going to at least try to do her up the ass next time.
“Yeah, tonight sounds great…Oh, shoot, I’m supposed to have dinner with a friend.”
“Oh, okay.”
“But it’s no big deal, I can cancel. I’d love to see you again.”
They kissed goodbye. Andy tried to fall back asleep, but couldn’t. He kept hearing Katie say, What’re you doing? Who was he kidding? There’d been no playfulness at all in her tone. She might as well have said, What the fuck’re you doing? He was just dreaming, thinking she’d ever be into having any anal action. The odds of that happening tonight, or any night, were slim to none.
Andy showered and got dressed. When he went out to the living room area he saw Will in the kitchen making coffee, wearing boxers and nothing else.
“Amanda here?” Andy asked.
“Nah, she just left,” Will said, smiling the way guys smile after they’ve gotten laid. “Bro, you’ll never have to get me a birthday present ever again.”
“How was it?”
“Awesome, dude. We were going at it all night. When we went into my room, I swear to God, she gave me one of the best blow jobs I’ve ever had. You know how some girls try to, like, rush through it? Like it’s a race or something?”
“Yeah,” Andy said, jealous as hell. Katie hadn’t even blown him yet. And why was he dating her?
“Well, Amanda was the total opposite, man,” Will went on. “She took her sweet time. It was like she was, like, worshiping my manhood. I mean, she’d take breaks, you know, and, like, admire it. It was like she was Picasso and my dick was the clay. She was molding me, using her fingers to—”
“All right, I get the picture,” Andy said.
“Then came the Oprah moment, the moment of truth—”
“And the answer is…”
“Wanna give me the drumroll?”
Andy rolled his eyes, then started patting his hands against the countertop dividing the living room and kitchen.
“Swallow, baby,” Will said.
Andy shook his head, smiling. He was jealous, but he was also imagining Will as a pediatrician someday. He knew one thing—he was keeping his own kids far, far away from Will.
“But I didn’t even get to the best part,” Will said.
Andy knew what Will would say, but he prayed he was wrong. There was only so much jealousy a man could handle.
“What?” Andy asked cautiously.
“We did it twice. It was really good. Then, it must’ve been three, four in the morning, and we’re starting to go at it again. I swear, at this point, it felt like my dick would fall off. Then she says, I’m kind of sore, why don’t we do something else? So I thought she was gonna go down on me again, but instead she—”
“No way.”
“Way.”
“Come on.”
“Yep, on the first date! Can you believe that?”
Actually, Andy couldn’t believe it. He felt like God was playing some kind of cruel joke on him. Was he the only guy in New York not getting any anal sex?
“Man,” Andy said, “you better pay me back for this. I’m serious. You better set me up with some nurse at the hospital or something. Someone super slutty.”
“Don’t worry, you’re in, bro, you’re in,” Will said. “But why do you need somebody else? Katie seems really cool.”
“Not so cool.”
“What do you mean? She seems totally into you. She’s really cute, too, and she probably does everything, right?”
There was no way Andy could tell the truth, that he’d barely fucked Katie after dating her all those times. He’d never live it down with the guys.
“Yeah, she is pretty wild,” Andy lied.
“Figured,” Will said. “If a girl’s good in bed, her friends are always good, too. It’s because girls talk about it, you know? I mean about technique. They share trade secrets. So what’s wrong with her then?”
“Nothing,” Andy said. “I just want to change things up, not get too, you know, intense. And she’s kind of a little too slutty, you know? I mean to, like, date. I mean, like, seriously date.”
“Yeah, I know,” Will said. “I like Amanda, too, but I can’t see going out with her more than another few times. When a girl does everything on the first date, you gotta wonder, you know? But I won’t dump her for a week or two at least. Last night was way too much fun.”
Later on, at work, Andy was still trying to get over his jealousy, when he got an e-mail from Katie, telling him how much she was looking forward to tonight. Suddenly Andy felt like he was trapped in boyfriend land. He and Katie had been seeing way too much of each other—what had it been, four dates in the last week?—and for what, some just-okay sex? It was time to back off, become more distant, or, better yet, dump her.
He was about to delete her e-mail and forget all about her, but then, remembering what Will had said about girls exchanging trade secrets, he decided he’d go out with her one more time. But if he didn’t score anally tonight, she’d be history.
At eight o’clock, he went to pick her up at her place. It was raining, which turned out to be key. He was psyched when she said she didn’t feel like going out in the bad weather and suggested ordering in Chinese instead. They’d finished their hot and sour soups and were into their steamed shrimp dumplings when Andy leaned over the table and kissed her. They moved to the couch and he could tell she was really getting into it. Then she looked at him, smiling, and said, “Wanna build up an appetite?”
A minute later, they were in her bedroom, getting naked, then they started doing it. He got on top for a while, then she took over. She was bouncing around really hard, making a lot of noise, then she stopped. She bent over, kissed him, and said, “I like you so much,” and he said, “I like you so much, too.” He could tell this made her really happy because she started bouncing on him even harder. Then she came, her face turning pink and getting all scrunched up, so he knew she wasn’t faking.
Afterward, she collapsed onto her back, catching her breath, then said, “God, that felt great.” Then, a few seconds later, “How do you want me?”
Andy knew this was code. She wouldn’t come out and say she wanted to be fucked up the ass. No, no nice, normal girl would ever say something like that. But after last night, she knew what he wanted to do, and she wouldn’t’ve said, How do you want me? leaving the ball in his court, if she wasn’t ready for it. Yep, this was it, all right—his lucky day. Someday he’d look back on this, the way he looked back
on the day he lost his virginity. He wanted to savor every second of this so he’d remember it clearly forever.
“From behind,” he said.
She turned over quickly, onto all fours.
“I mean with you flat on your stomach.”
She collapsed onto the bed, lying there, waiting for him. He knelt on top of her, knowing that in a few seconds everything would be different. From now on, his life would be divided into two parts—BAS (before anal sex), and A AS (after anal sex). He parted her butt cheeks carefully, but before he could do anything, Katie jerked forward, as if he’d tried to stab her, and said, “Hey.”
He was so caught up in trying to savor the moment that he didn’t even realize she’d said this, and continued what he was doing, until she said “Hey” again, almost yelling.
Then he stopped and said, “What’s wrong?” He wasn’t playing dumb. He’d been so convinced that they were on the same page that he honestly didn’t know what was the matter.
“I think you lost your sense of direction there for a second,” she said.
He wondered if she was being sarcastic, if she really wanted him to continue.
He decided to roll the dice.
“No, I didn’t,” he said.
He was about to try again but she squirmed away and said, “Come on. Stop kidding around.”
“What do you mean? I thought it was cool with you.”
“What was cool with me?”
“You never did it that way before?”
“No. Of course not.”
“Oh, I just thought…”
“That’s disgusting.”
It definitely didn’t sound like sarcasm anymore.
“Oh,” he said. “I just thought it’d be cool to try it one time.”
“Sorry. I’m just afraid it’ll hurt too much.”
“I promise I’ll be gentle.”
“I’m really not into it.”
“Oh, that’s cool,” he said, but couldn’t’ve been telling a bigger lie.