Midlife Glitch (May/December Romances Book 1)

by Boswell, Ben

  We were both wary around each other, the consequence of our confrontation, such as it was, a few days earlier. Or maybe we were feeling something else. I don’t know.

  I had certainly thought of her, sexually, now several times. Hard not to. Once that barrier was broken, the reality of her mesmerizing beauty was impossible to deny, especially when she was prancing in yoga pants. I get that they are comfortable and she wasn’t wearing them to tempt me, but man, what kind of brilliant demon invented the damn things?

  And yet, I thought I had it under control.

  ***

  Wednesday at dinner, Ashley seemed particularly pensive.

  "Can I ask you a question?" She said suddenly.

  "You mean besides that one?" I replied. I was in full cool dad mode.

  She gave me a smirk and called me on it. “Really?”

  I laughed. "Okay, got me. Sure, go ahead."

  She hesitated and then took a deep breath.

  "It's about that night. The night I was outside your bedroom."

  I felt a weird surge of panic. I took a deep breath. "I told you, it's not a big deal. It's just between us."

  Cool dad, feeling his cool slipping away.

  "I know." She paused and blushed. "It's just, well, Joanne really seemed to enjoy herself."

  I laughed, a little uneasily, but didn’t see an easy way to disengage from the conversation. I stumbled forward. "I should hope so. I mean, it's supposed to be fun, unless you're one of those 'just for procreation' people."

  "Well, yeah, but I mean, does she... you know... enjoy it every time?"

  I was taken aback. This was a very personal line of questioning. And unexpected. I decided to answer. She obviously needed to talk something out. "I don’t know for sure. I think so. I hope so. She's never complained, and she's not shy about saying what she wants. But I imagine she sometimes has an off day, or maybe I do."

  We were both silent for a moment.

  My curiosity was killing me. Why would this gorgeous eighteen-year-old care about my sex life?

  "Why?" I asked.

  She blushed again. "Well, it's just, I've never...."

  As she answered, I immediately regretted my question. Where was I going with this?

  "Oh. Well, look, you're still young. You don't need to rush it. There is nothing wrong with waiting until you find the right guy."

  My words came out in a weird rush, cool dad pabulum, admixed with an unmistakable desire to extricate myself from an awkward conversation.

  She looked at me quizzically, then a glimmer of understanding crossed her face. She shook her head. "No, no, I'm not a virgin. I mean, I'm not, like, a slut or anything, but I've had a couple of boyfriends."

  I smiled despite myself.

  “What?” she asked defensively.

  I’m sorry. “It’s just, the way you phrased it, virgin or slut….”

  She nodded. “Yeah, right. It’s sort of the boxes they put you in.”

  And suddenly, we were having a real conversation.

  I nodded. “I think it is especially hard for women. Young women in particular, you know.”

  “I’m not really worried about that,” she replied. “You know, people say all sorts of stupid shit. But I guess, I dunno, I’m just hoping that, well, it’s ever for me like it is for Joanne.”

  "Oh...." I hesitated. "Well, I don't really know. I mean, I hear some women having difficulty, you know, achieving climax. I guess it takes time, you know, learning about your own body."

  "No, that's not what I mean either. I can get myself off," she replied with bracing frankness.

  It was my turn to blush as the memory of her writhing in passion flashed in my head.

  She continued, "No, I mean, I've never been able to with my boyfriends. I just never quite get there."

  "Well, that takes time too. Joanne and I have been together a long time.” Why had I stressed that word so obviously? “We know each other pretty well. You'll find the right guy. If you have a strong emotional connection, it's easier, I guess."

  She regarded me pensively, but I could tell I hadn't quite satisfied her curiosity.

  "Have you talked to your mom about this? Your friends?"

  She laughed. "God, I could never talk to Mom about this. She'd pack me off to a convent." It was my turn to laugh. Trent was an old friend, but he'd somehow managed to end up marrying a born-again Christian. "And my friends. Well, half of them are virgins, and the other half are always bragging about their boyfriend and their crazy sex lives. Virgins and sluts, right? I'm pretty sure it's bullshit, but it's just not something I wanna talk to them about, you know?"

  I nodded. "I wish I had more answers. All I can say, I guess, is be patient. It'll happen."

  She smiled. "I guess.... Well, thanks for listening."

  We sat in silence for a few minutes. "So what do ya think? American Idol tonight?"

  She shook her head. “I think actually I’ll just lay out by the pool tonight.”

  “Okay then, baseball for me.”

  ***

  I did try to watch the game. I really did. But when I caught glimpse of Ashley walking by in a skimpy, black bikini, a towel draped over her shoulder, my ability to concentrate plunged. I couldn’t see her from the sofa in the family room, but I knew if I just walked over to the big bay window, I would have a perfect view of her.

  I tried to focus on the TV, but my eyes just kept drifting over the window. Back to the TV. Wait, when had they scored a run? And back at the window.

  I probably should check on her, right? I mean, they say not to let people swim alone. Just a peak to make sure she was okay. I chuckled at my own pathetic rationalizations.

  Yeah, I was a happily married man, and yeah, she was young enough to my daughter, but I’m still a man, and it was still just a peek. So I rose and approached the window slowly, like I was sneaking up on it.

  And there she was, a teenage girl, texting on her phone. So prosaic, and yet so enticing. Her slender legs, creamy thighs, the perfect flatness of her stomach, her impossibly generous cleavage when she turned to her side.

  I thought about her fumbling about with her ham-fisted boyfriends who were unable to get her off. God, it really was pearls before swine.

  I shook it off. I needed to stop being an asshole. She was just a kid. A pretty kid, but just a kid, and I needed to get my mind out of the gutter.

  I went back to my sofa and the game. I really have no idea who won.

  ***

  Friday morning when I dropped her off at the subway, she mentioned that she might be a little late. Her office was having an afternoon cocktail reception.

  She called at 6:30pm and said she'd been invited out with some of the other interns. She sounded as if she'd had a few. I groaned. I was responsible for her, but I also didn't want to be overbearing. I said okay, but told her not to be too late.

  She called again at 9:15pm. This time she was definitely drunk, slurring and giggly.

  "Can you come get me?" she asked. "I'm at this, um, party thing, and I'm not sure how to get back."

  I agreed and she texted me the address. The place was a little off the beaten path, in a residential neighborhood. It took me almost thirty minutes to get there. She was waiting out front by herself when I arrived.

  "How'd you get all the way out here?"

  She rolled her eyes. "Some guy. Said it would be a fun house party, but turns out it, it was just his roommates drinking." Her voice was throaty, slurred. She obviously had more than a few.

  "Oh."

  "He's getting drunk inside, and didn't seem eager to stay sober enough to drive me home after I told him I wasn't interested in seeing his room." She seemed disappointed it had come to that.

  "Sorry about that," I replied without thinking.

  "What?"

  I chuckled. "I guess I'm just apologizing for all men, or something."

  She laughed and put her hand on my shoulder. "Thank you for picking me up."

  Our eyes met
. One second, two seconds, three. For a moment, I was tempted to lean over and kiss her. Instead I cleared my throat and looked away.

  "I guess I better get you home," I said, putting the car in gear.

  I could feel her looking at me. The sexual tension was almost palpable. I tried to ignore it, but I couldn't. The truth is, I wanted her. Wanted her badly. I'd been thinking about her from the moment she'd arrived in our house, walking around in her short shorts, clingy tees. She wasn't even trying to be provocative. She was just dressing like a normal teen. Even in her work clothes, she just exuded sexuality. And then I'd seen her masturbating… we’d talked about sex… and I just couldn't stop thinking about her. And now, we were alone together. She was drunk and eyeing me frankly, provocatively.

  But it couldn't be. It had to stay just a fantasy.

  I swallowed hard. "Ashley, we just can't do this," I began. I turned to glance over at her and.... She was asleep.

  I drove home the rest of the way in silence, unsure whether I should be relieved or disappointed or maybe both.

  I pulled into the driveway and she woke up groggily. "We're home," I announced.

  She grunted. I think she'd have been just as happy to sleep out in the car at that moment.

  I walked over to her side and opened the door, helping her to her feet.

  "You going to be okay?"

  "Yeah, just tired," she groaned.

  She took a step and immediately stumbled. I reached out to catch her before she fell, and swept her into my arms. I lifted her off the ground. She was as light as a feather, just a dainty little thing. She wrapped her arms around my neck, her head resting on my shoulder.

  "Thank you, Uncle Danny," she said softly, sleepily.

  I chuckled. She hadn't called me that in years. Not since she was a little kid.

  I carried her up to her room, and laid her on her side on the bed. I slipped off her shoes, and draped a thin blanket over her. Then turning out the lights, I snuck away downstairs.

  I started to replay the evening in my head, but it was just too painfully awkward. Thank God, I hadn't tried to kiss her. And, thank God, she'd been asleep when I'd started to explain why we couldn't be together. I could almost imagine her reaction, appalled, disgusted when she realized what I'd been thinking.

  I poured myself a scotch, a double... well, maybe a triple, and downed it quickly while watching Sports Center. Then still in the grip of self-loathing, I went to bed.

  I lay there for a while, the booze seeping into my bloodstream, clouding my head. Ashley, Ashley, Ashley, Ashley.... She was all I could think of. I slowly stroked myself, eyes-closed, thinking of her, until finally the Scotch carried me off to sleep.

  Chapter Four

  I awoke in the dark to the sensation of movement in the bed. Fucking cats, I thought, immediately realizing it wasn't them. I jerked back startled.

  "It's only me," she cooed softly, her face nuzzling into my neck.

  I glanced at the clock. 2:36am.

  "Are you okay?" I asked.

  "Mmm, hmm," she moaned, kissing my check, her hand snaking down under the covers to rub my crotch.

  "What are you doing?" I asked groggily.

  "I want you," she said simply, now leaning over me to kiss my cheek.

  That jolted me awake.

  "Ashley, you're drunk," I suggested as gently as I could.

  "A little," she admitted. "But I know what I want. I've been thinking about it for days." She slid her hand under the waistband of my PJs and firmly stroked my cock.

  “You want it too,” she added, feeling my hardness.

  I did want it. But I knew we couldn’t.

  "No, we can't do this," I said, reaching out to push her away.

  It was then I realized she was naked. Totally nude. Not a stitch of clothing. Trying to separate us put my hands on her breasts. I recoiled and she sprang back toward me. I tried to take her by her shoulders, but she wrapped her bare legs around me, and sucked my thumb into her mouth.

  "No, stop!" I ordered, trying again to escape her clutches. She just giggled.

  I know it seems crazy, but between not wanting to hurt her and not wanting to touch anything inappropriate, I was having a devil of a time separating the two of us. And, of course, my body couldn't help but respond to this nubile creature writhing against me.

  Except, of course, that wasn’t it, not all of it. I could overpower her… if I wanted to. Without hurting her… if I wanted to. I could flee… if I wanted to. And I wanted to. But not enough, because the truth is, the feel of her lithe body against mine, that silky hair whipping across my face, her silly little giggle as we wrestled ineffectually… it was intoxicating. And yet, I knew it was wrong.

  I stopped struggling and tried to calm myself.

  "Ashley, stop it. We can't do this."

  She nuzzled in close again, kissing my neck, her erect nipples pressing against my arm.

  "You're right, we can't," she breathed as she sucked on my ear lobe.

  "This is wrong!"

  "Yes, so very, very wrong," she moaned as she ground her pelvis against my leg. She was mocking me.

  "Ashley...."

  "Shhh." She took my hand and pressed it down between her legs. "See what you do to me?" she cooed.

  Her muff was drenched. Is there anything better able to break down a man’s willpower than a wet pussy? How many men have thrown it all away in the intoxication of it? She rubbed my hand up and down her slit until I could feel the heat and wetness within.

  She'd worked her other hand back into my bottoms and was again stroking my cock, which was now rock hard, almost painfully so.

  She kissed me on the lips. Lightly at first, but after a few moments it turned into a rough, wet embrace, her tongue jamming deep into my mouth. She'd let go on my hand, but I was still rubbing her snatch. She was so fucking wet. My finger slipped between her lips, partway into her steaming cunt.

  Then suddenly she rolled onto her back and pulled me on top of her. She was surprisingly strong, or at least her excitement made her seem that way. This time, I didn't resist. She wrapped her arms around my neck and kissed me hard. Mostly by instinct I fumbled with my PJs and wrenched them down about mid-thigh.

  I stabbed my erection blindly toward her. Once, twice, on the third time, it found its mark, the tip splitting her wet cunt. She gasped softly. Without a pause, I entered her slowly, not stopping until I was buried completely inside her.

  "Oh God, you're big," she moaned.

  But it wasn't that I am so big; rather, it was that she was so fucking tight. I'd forgotten what an eighteen-year-old pussy feels like; it had been so, so many years since I’d had the opportunity to experience one. But it is heaven on earth. My cock felt like it was enveloped in a compression sleeve. It was so snug that fucking would have been impossible if she hadn't also been so incredibly wet. And the heat. It was like an oven.

  I wasn't even thinking about her enjoyment. I wasn't thinking about anything, really, except that amazing sensation as I fucked her tight, wet hole with long, slow strokes. I have no idea how long that lasted. I was completely lost in the moment.

  And then suddenly it was like a thousand fingers gripped my cock, squeezing it in waves up and down the shaft. I opened my eyes to see her looking up at me, wide-eyes, her lips in the shape of a perfect "o" as she moaned her pleasure.

  I was sweating. We both were. I raised myself up on both arms and looked down at her. She was breathing heavily, her perfect breasts rising toward the ceiling with every gasp.

  I pulled out and got to my knees.

  "No, don't stop, please," she begged.

  "Don't worry. I don't want to stop either," I replied as I ease off my PJs completely.

  I caressed her slim, toned legs and placed her ankles up over my shoulders. I slid a pillow under her ass, and then scooched in close. I rubbed the tip of my cock up and down her wet snatch, making her squirm in anticipation. Then I entered her again, and she let out a delicious little mewl
of pleasure in response.

  She was just a tight as before, her pussy clinging to my cock as I slowly slid in and out.

  From my kneeling position, she was spread out before me. Her golden hair was splayed across the pillow, her hands tracing circles over her belly and chest. Her breasts were jiggling with each thrust.

  I looked over at her dainty, little, feet resting on my shoulders. I'm not a foot guy, but I couldn't help it and sucked her toe into my mouth. She giggled, and I laughed as well.

  I caressed her legs, tracing my fingers along her inner thigh. Resting my hand on her damp, blond muff, I let my finger brush against her swollen snatch. She shuddered and I started rubbing her clit in small circles. She moaned loudly, her hips now gyrating, rising upward to meet my thrusts.

  "Oh my God, oh my God, oh my God," she squealed, her voice rising higher and higher as she arched off the bed impaling herself completely on my shaft. The thousand fingers squeezed my cock.

  She dropped back heavily onto the mattress. I started thrusting again, but she reached up and put her hand on my belly.

  "Just a second," she gasped. "I need a break."

  I pulled out and lay down next to her. She was breathing heavily, almost as if she'd run a sprint. Her hand reached down and firmly stoked my slimy cock. I took the opportunity to caress her body, cupping her firm breasts, and tracing the nipples with my fingertips.

  "Did you yet?" she inquired after a few moments.

  "No, but...." I was going to tell her it was okay. That we didn't need to continue if she was done.

  "I want you to," she cut me off. "How do you want me?"

  I knew the answer right away, but I hesitated for a moment in answering. I didn't want to break the spell. This was something Joanne didn't like to do. But then I went for it.

  "I want you on your hands and knees."

  "Mmmmm, okay," she chirped happily.

  Her eagerness to please was almost as sexy as her tight, little body. Almost. She got on all fours, and I knelt behind her. It was an amazing view, her long blond hair streaming down her back, her body tapering from her shoulders to her tiny waist, and then flaring again to an absolutely perfect, firm, heart-shaped ass.