The Obstacle Course

by JF Freedman

  “I’m going to show Roy my room,” she’d told her mother. She had her own room at her grandparents’ she was there so much of the time.

  Her mother didn’t care. Now that the recital was over she didn’t have to play-act around Melanie anymore. If anybody noticed they didn’t let on when I followed Melanie up the stairs to the third floor and into her room.

  I was sitting on her bed while she laid in my lap. Our mouths were all over each other, my free hand working its way up the side of her leg, along her stocking. When I got to her bare leg and started for her underpants, she grabbed my hand.

  “No,” she said, “that’s too fast. I’ve never done this before. Here, up here.” She put my hand on her tit, over her bra. The front of her dress was down and her bra was out, a dark-blue bra like her dress. It was stiff and shiny, I knew she’d never worn it before, like everything else she was wearing. Even though she was sucking on my tongue like a fiend, I also knew that she’d never had a boy put his hand on her tit either. She sure was liking it, though, she was squirming all over me, I could feel her ass pressing down on my dick through the material. This girl was hot as a pistol, it was like she had an entire life of stored-up sexual desire inside of her and now it was exploding out.

  “They all want to know what?” I asked.

  She kissed me some more, her hands all over my neck, my hair, inside my shirt. Her mouth was soft—big soft lips, soft tongue. A born makeout queen, breaking free from inside that prissy old-fashioned life she’d been living for fourteen years.

  “Know what?” I repeated. I worked my hand under her bra, onto her bare tit, onto her nipple, which was standing up erect. I started massaging it gently and that really got her moving all over me, her legs sliding around, her toes curling and uncurling in her stockings.

  “Know what?”

  “How I … oh God, oh God, I’ve never felt anything like this before!” She grabbed me by the hair and looked me serious in the face. She had a wild look in her eye.

  “How I got you!”

  I sat back, my hand resting on her breast. Jesus, what a bitch! Here she was, the nicest girl I’d ever met, definitely the hottest girl I’d ever been with, in ten minutes I’d be finger-fucking her, she’d stop me and stop me and then she’d let me because she wanted to all along but had to play the game, here all this was happening and she was feeling shitty about herself. I hate that kind of garbage, it made me think about poor old Vernice and other kids I know, boys too, who think that because they’re a little bit fat or not so pretty in the face they’re doomed forever.

  “Roy,” she said, putting her hand on top of mine and moving it around on her tit again, “don’t stop.”

  I started up again, real gentle. Her eyes closed and she started moaning softly.

  “That’s their problem,” I told her. Theirs and her mother’s and everybody else who only saw what she looked like on the surface.

  She smiled up at me, her eyes still closed.

  “I love you, Roy.” She pulled my mouth down to hers and frenched me so deep I could practically feel her tongue stroking my tonsils. “You’re the best thing that ever happened to me.”

  I kissed her back and slid my hand inside her panties. She didn’t even mock-protest that she was trying to stop me.

  “I have to go to the bathroom.”

  “Me, too,” Melanie said. “I’m sticky all over from you.” She was grinning like crazy, like Eve must have the first time she ate the forbidden fruit.

  “Where’d you learn to talk that kind of trash?” I teased her.

  “Other girls. But I know it’s mostly lies, I know that much.”

  No shit, I thought. Ninth-grade girls are just like ninth-grade boys.

  I’d been finger-fucking her for about ten minutes. She had sucked her breath in hard when I first put a finger in, just one index finger, she was plenty wet but she was tight as a drum, obviously she was a virgin, she probably had never had anything in there in her life, not even her own fingers. It took me a good five minutes to squeeze a second one in there, but that’s all she was going to take. I thought about Ruby, my colored hooker. I could’ve put my whole fist inside of her if I’d wanted to. Forget that shit now, this girl was going to give me all the loving I could handle and then some, she’d do anything I wanted.

  “Next time,” she’d said breathlessly. “You can come to my house, my mother’s hardly ever there.”

  “When?” I had panted, so horny I thought I’d shoot my load right in my drawers.

  “Next weekend?”

  “Yeah.” I’d do it on my way over to the admiral’s, and on my way home, too. I thought about Burt and all those guys who were always talking about getting it. The difference was, they all talked about it, while I was going to, the real thing, and for free, not with some hooker, although I’d liked it fine with Ruby, she’d taught me more that one time than I could’ve learned from doing it a thousand times with girls my age. The only problem was, I wouldn’t be able to tell them about Melanie, not her actual name. She was too nice a girl; I could never do that to her. They wouldn’t understand anyway, if they saw her they’d just think she was a plain girl, certainly not worth writing home about.

  The only thing was, which I have to admit was eating at me even as I was thinking about it, was that I didn’t know if I actually would fuck Melanie next weekend, even if she let me. It didn’t feel right somehow—she was too inexperienced, she’d never even kissed a boy, practically. Fucking Melanie this early on would be like taking candy from a baby.

  Maybe I’d change my mind when the time actually came, but next week seemed too early. We could make out like crazy for a whole bunch of times, until I was sure in my own mind I wasn’t going to do a wham-bam-thank-you-ma’am on her and then never see her again. Once I was sure of that, then we could fuck all day and night and I wouldn’t have any guilty pangs about it.

  We got off the bed. She looked at herself in the dresser mirror.

  “Oh, God! If anyone sees me like this I’ll die!”

  She did look pretty raggedy. Her lipstick was smeared over half her face, her hair was a mess, her clothes were all wrinkled and undone.

  “I’ve got to clean up,” she told me. “You, too.”

  I looked at myself in the mirror, next to her. It was the usual look you get after you’ve been making out hot and heavy for a half-hour. She didn’t know the look, never having done this before.

  “You can use the guest bathroom at the end of the hall, on the floor below,” she said. “My grandparents’ bedrooms are on that floor, so be careful they don’t hear you, my grandmother might be old but she’s got ears like a hawk. Just don’t let anyone see you, especially my mother, that’s all I need. I’ll meet you downstairs in ten minutes,” she added in this real flirty tone of voice, giving me one last soul kiss and pushing me out of her room. We’d been together two times and she’d gone from being a shy wallflower to a red-hot makeout artist. It’s incredible how easy that is once you know somebody wants it from you like you want it from them.

  I tiptoed down to the second floor, making sure I wasn’t spotted, not only because I had her makeup smeared all over me, but also because I had a hard-on like an elephant, even with my hand in my pocket it stuck out like I had a ruler in my pants. I didn’t know what the admiral and Mrs. Wells would think, but I didn’t want to take any chances. Melanie was this nice girl they liked, they didn’t want her corrupted by some hood from the wrong side of the tracks—Mrs. Wells especially. Even though she was being much nicer to me, I remembered all too clearly the way she’d put me down when she thought I wasn’t listening. I was doing good all around, I didn’t need to fuck anything up.

  Melanie had about creamed in her jeans when I’d told her I’d gotten into Farrington, up there in her bedroom before we’d started making out.

  “Oh, Roy,” she’d squealed, “that’s great, that’s so great, why didn’t you tell me earlier?”

  “It was your big day, I d
idn’t want to steal your thunder.”

  “It’s a big day for you, too, it’s even bigger for you. Oh, Roy, I’m so proud of you.” She’d given me a kiss on the mouth, the first of many. I knew she wanted to do it with me, she didn’t need any excuses, but telling her about Farrington hadn’t hurt.

  “You’ll look great in a uniform,” she’d said.

  I’d thought about that, how cool it would be. Their uniforms were modeled after the Naval Academy’s; it would be like I was a midshipman-in-training.

  “There’s a great girls’ school nearby, Agnes Walker,” Melanie had told me. “Some of my friends have gone there, they say it’s neat, you date boys from Farrington. I could transfer, we could both be there.”

  “Yeah,” I’d said, “that would be great.” I got a little uneasy when she’d said that, not that it wouldn’t be great, hot and cold running pussy any time I felt like it the way this girl was going, but she was pushing mighty hard, pretty soon she’d be telling me what kind of engagement ring she wanted. It’s like my sister, she’s finishing eleventh grade and if the right boy comes along she’ll get married the day she graduates. That’s not a life for me, I’ve got a whole career ahead of me to worry about. Still, it’s nice when someone wants you as much as Melanie wanted me.

  After I finished washing Melanie off my face and combing my hair I took a look at myself in the bathroom mirror. It wasn’t perfect—a trained eye could see what I’d been up to, but like my old man says, it was good enough for government work.

  As I left the bathroom I could hear voices drifting up the staircase from downstairs—the admiral, Mrs. Wells, old Admiral Prescott and Melanie’s grandmother, Melanie’s mother. And Melanie, she was already down there, I must’ve been daydreaming in the bathroom, remembering her taste in my mouth. I felt kind of nervous as I walked down the long, musty hallway towards the staircase, because I wasn’t comfortable up here by myself in old Admiral Prescott’s house. I wasn’t part of this house, part of the lives of these people. I was not here because of myself, but because Admiral Wells had brought me into his home and I’d met Melanie because of that, and she’d invited me to her recital because she’d fallen for me, and for that reason they had to be nice to me. And even though Melanie Prescott had just told me that she loved me and had let me put my hand inside her pussy and was ready and willing to give her cherry up to me next week even though she was only in the ninth grade and hadn’t had a real date in her life didn’t make up for my not being part of this. I was an outsider to them, and I always would be. Even if I married Melanie Prescott and lived in this very house, I still wouldn’t be one of them.

  That was okay, though, because a lot of what they were was bullshit to me. I didn’t want to be like them, I wouldn’t mind being rich and shit like that, but not all the rest of it. Not the boring parts.

  Partway down the hallway was an open door leading into a bedroom. As I walked by, I stopped for a second and glanced in. I didn’t have any reason, I was curious was all, maybe I wanted to see how different it was from what I knew. Or maybe I was just being my customary nosy self, which is closer to the truth.

  There were the usual items, chests of drawers, lamps, a bed—all the best quality, even my untrained eye could see that—and clothes thrown on the bed. A woman’s clothes, like whoever’s room it was had been trying different dresses on until she found the one she liked. My sister’s room is like that, half her clothes are on her bed most of the time.

  Melanie’s mother was using this room, I realized, she would sleep here overnight some of the time, the times when Melanie was staying here with her grandparents, since she wouldn’t want to be alone in a big old house, especially if her daughter wasn’t there. She probably kept several changes of clothes here because of all the fancy affairs they must’ve put on—I could see her lugging out a bunch of dresses and trying them all on, one after the other, deciding which one was best for the occasion. She would’ve brought some from her own house, too. She was that vain kind of woman, I could tell—she’d take forever figuring out what she should wear so people would look at her; especially men. Trying dresses on all day, putting on her makeup, all that vain shit women do. I’ll bet she made Melanie help her, too, she’d tell her “I want to look good for you, darling,” when what she really wanted was to look good for herself, and just as important, better than her daughter, even though it was her daughter’s big day, not hers. I remembered her holding my hand before the recital, trying to flirt with me right in front of Melanie, to steal her daughter’s thunder.

  The thing is, she was kind of sexy, for an older woman. I’d noticed her figure when Melanie had introduced us, I couldn’t deny that. She was the kind of woman who made you look at her, that was what she was all about. She had to be horny as hell, being divorced from Melanie’s father (who had humiliated her by leaving her for a younger woman); she was probably on the make for every man around, even if he was only fifteen and her daughter’s date. Of course, that could’ve been my own fantasy: guys’re always fantasizing about fucking a mother-daughter combination, that’s one of the ultimates—I’ll bet some of Ruthie’s boyfriends have even thought about fucking my mom. She probably would, too, if she thought she could get away with it, the way my old man treats her. Serve his ass right.

  I shouldn’t go in that room; I knew that. I should haul my young ass downstairs before they started wondering where I was. But now I’d built this fantasy in my brain about Melanie’s mother, about the two of them naked together, with me in the middle. It was being with Ruby that did it; ever since then I’d been thinking about older women.

  Melanie’s mother’s clothes were calling to me, lying there on the bed. I wanted to touch them, just for a moment. Maybe part of her smell would be on them. Something. I’d just take a quick look, pick up one dress.

  That was bullshit: a pair of undies is what I wanted to pick up, a stocking. Something with the touch and smell of her sex on it. I still had this raging hard-on from having made out with Melanie, and sex was the only thing on my mind. What I really wanted to do—I hated to admit it but I had to—was jack off into a pair of Melanie’s mother’s panties. I’d do it real fast, be rid of my boner in thirty seconds, I’d stuff the panties in my pocket and nobody would ever know.

  I picked up a pair. They were real silk, a light peach in color, they practically slipped out of my fingers they were so silky and slippery. I moved away from the bed, towards a corner of the room, turned my back to the door and reached for my fly.

  Then I saw it, sitting on top of her chest of drawers, hidden behind a picture in a gold frame, a picture of a baby girl. Melanie as a baby, it was the same hair. If I hadn’t been standing inside the room I wouldn’t have seen it, because it couldn’t be seen from the hallway.

  The it I am referring to was Mrs. Wells’s silver statuette, the one that had been stolen. The one I’d seen old Mrs. Prescott pick up. I’d known that old bitch had stolen the statuette from the giddyup, and now here it was.

  Forget about beating off. My cock went limp so fast it was like it had never been erect at all. I tucked it back in and zipped up my fly.

  I didn’t know what the fuck to do. I could go downstairs and tell on her to the Wellses, but then I’d have to admit I was in her room, and what was I doing there? I was going to tell them I wanted to masturbate into a pair of Melanie’s mother’s underpants? I couldn’t say I’d seen it from the hallway as I just happened to be strolling by, because that was impossible, even if it hadn’t been hidden behind the picture frame it was too small to be seen from there, you’d have to have better eyesight than Superman.

  Ratting on old Mrs. Prescott would cause a huge stink. Everybody would be embarrassed as hell, Melanie most of all. She’d take it personally, like somehow it was her fault, like if I hadn’t been up there corrupting her it would’ve all passed over. Today was her special day—first she’d knocked people over with her piano playing, and then she’d made out for the first time in her young, i
nnocent life with the boy of her dreams. It would kill her, finding out that her grandmother, who took better care of her than her own mother, was not only a common thief, but had stolen from Beatrice Wells, her best friend.

  I should never have gone in this room in the first place. I should’ve learned my lesson back there in the Smithsonian, with Darlene and Danny. But I had, and it was too late to turn back.

  I picked it up, hefting it in my hand for a second. It was heavier than it looked, real silver. Mrs. Wells wouldn’t have anything phony in her house, that I knew.

  “What are you doing in here?”

  I spun around. Old Mrs. Prescott was standing in the doorway, staring at me.

  “What are you doing in my guest bedroom, young man?” she demanded in a loud, harsh voice. She didn’t sound like a singing little bird now, she was barking like a dog. Her face was all red and splotchy, the way people’s faces get when they’ve had too much to drink or they’re mad as hell.

  “Nothing,” I mumbled under my breath. I was holding the statuette in my fist. It felt like a burning rock.

  “You thief!” she screamed at me.

  “No, no, I’m not … you got it backwards, lady.” I was fucked, now everybody would find out, Melanie’s day would be ruined, I’d never see her again, Admiral and Mrs. Wells wouldn’t be able to be friends with the Prescotts anymore. All because this old bitch had stolen from her friend, and I’d been a nosy asshole and found the fucking evidence. What pissed me off more than anything, besides getting caught where I shouldn’t have been, was her calling me a thief, when I was holding onto the very thing she’d stolen.

  “What’s going on?” Admiral Wells was all of a sudden in the doorway next to old Mrs. Prescott, and Mrs. Wells, and Admiral Prescott, and Melanie’s mother, and Melanie. The whole shooting match, standing in the doorway, staring at me.