Midlife Glitch (May/December Romances Book 1)

by Boswell, Ben

  I rubbed my cock up and down her slit until she was moaning, her ass swaying in anticipation. I entered slowly, worried that she might be getting sore or that she her excitement was ebbing, but her soft mewls of pleasure and unbelievable wetness let me know she was up for more.

  It was my turn, so I fucked her harder and faster than before, burying myself into her over and over, our bodies slapping together loudly. I reached around and fondled her full breasts, pinching her nipples until she yelped excitedly. Releasing her tits, I let my hands rest just beneath them so that each thrust caused her erect nipples to brush against my fingers.

  Then I grabbed her ass cheeks, squeezing them hard, pulling them apart so that I could more easily see my cock spearing her tight snatch and her perfect, little asshole pulsing with each stroke. I ran my thumb up her crack, and pressed it lightly against her anus. She suddenly threw her head back and let out a high-pitched squeak as her body shuddered and her cunt spasmed against my cock for the third time. Joanne was always anxious about any ass play, and it was a thrill to be with a partner who seemed to relish it.

  Then as if all her strength suddenly disappeared, she collapsed face down onto the bed. I followed her down and continued pounding into her. In that position, she was amazingly even tighter than before, though so well lubed than I was able to slide in and out easily.

  She looked back at me over her shoulder, her hair a tangled, matted mess, her eyes wide, her mouth open and gasping. She looked nothing if not well fucked.

  “Oh my God, you’re amazing,” she gushed.

  Hearing that was an adrenaline rush. I thrust again, harder, and again, pressing myself into her completely, getting every last millimeter of my prick inside her. She gasped.

  And then suddenly I went lightheaded. I saw colors, and I came so hard it actually hurt for a moment as my dick hole stretched to allow a torrent of cum to escape. And then euphoria as my balls emptied completely, and I collapsed onto her back, my prick still buried in her tight wet hole.

  I gasped to catch my breath, and then rolled off her onto my back. She draped an arm over my chest and looked me in the eyes.

  "I... I... I...." she stammered.

  "I know," I groaned.

  I gave her a little peck on the nose and we both dropped into a dead sleep.

  Chapter Five

  I woke at 5:30am as the sun streamed through my bedroom window. I always forgot to draw the curtains. Joanne usually did that.

  I didn't dare move, or even breathe. Last night had been amazing, and I woke to find myself spooning a naked Ashley, her body warm and soft, and so inviting, her golden hair shining in the sunlight.

  But I was on the verge of a panic attack. When she woke, my whole world would come crashing down. I'd taken advantage of a young girl in my care. If she had regrets, if she claimed rape, who'd believe me? Who could possibly believe that this beautiful eighteen-year-old had been willing to sleep with me, a fifty-four-year-old man? I was old enough to be her grandfather. And had she even been willing? She'd been drunk. Too drunk to give consent? My stomach churned with guilt at what I'd done.

  Even if I avoided jail, my life was ruined. My marriage… dead. My friendship with Trent… obliterated. My reputation… gone.

  I was in paradise for the moment, snuggling this luscious creature, my hand wedged between her breasts, her hard ass against my crotch. But it was an illusion; one certain to turn into a living nightmare the moment she woke, realized what had happened, and jumped out of bed screaming.

  Her breathing shifted slightly, and she let out a soft moan, almost a catlike purr. I braced myself for the fireworks. But she just lay there beside me. And then I felt it, her fingertips on my arm. I didn't dare move, hoping she was still just stirring in her sleep. But then I felt something else. Her ass. Her perfect ass now rubbing slowly against my crotch. It was subtle, but unmistakably sexual.

  Was she still asleep? Maybe dreaming of a boyfriend or Rob Pattinson?

  "Ashley?" I breathed, bracing myself for coming explosion.

  "Mmmm," she moaned in reply.

  She twisted her neck and gave me an awkward over-the-shoulder kiss. Her morning breath was sour, but it was one of the best kisses of my life. Relief coursed through me.

  She rested her head back on her pillow and grabbed my hand from between her breasts, sucking my index finger deep into her mouth. Her ass ground harder against my increasingly stiff cock.

  I pressed up against her, our bodies molded together. She was so warm and inviting, hard and soft in all the right places. As she moved against me, my erection slid between her butt cheeks like a hot dog in a bun. She giggled softly. Ashley slowly pumped her hips, massaging my prick with her butt. I took my hand from her mouth and cupped her breasts, gently tweaking her swollen and sensitive nipples.

  She reached back and grabbed my cock, slipping in between her thighs. I pumped it back and forth slowly, gasping as her labia split and her wet snatch rubbed against my shaft. We moved together languidly, our excitement building. She grabbed my cock head and pressed it inside her, and with a thrust I slid all the way in.

  We both moaned at the same time. It was heavenly, her magical pussy again gripped my cock, and not for the first time I thought about how I never wanted it to end.

  We made love tenderly, my cock buried deep inside her as we slowly moved together. I explored her body gently, caressing her soft skin, tracing her lips with my fingertips. I kneaded her big boobs, rolling her nipples between my thumb and finger. She moaned softly, her pussy getting hotter and wetter around my cock. I slid my hand down over her flat belly, tracing the borders of her downy muff.

  I found her clit and gently ran my finger around her swollen little nub. She moaned delightfully. I rubbed her clit harder.

  "Oh God, you're going to make me come," she sighed in a throaty voice.

  She gasped then and a shiver ran through her body as her pussy repeatedly clamped down on my shaft. When she was done, she reached down and gently fondled my balls. I thrust into her harder, once, twice, three times and then came myself.

  I eased myself out her tight little pussy and looked down at her. She had her head on her pillow, eyes closed, with a big smile on her face. I cuddled her again, neither of us bothered by the wetness between us, and within minutes I could feel her breathing rhythmically as she fell back asleep.

  After a few more minutes, I extricated myself and got up, leaving her there dozing peacefully. She looked like an angel.

  ***

  I took a long, hot shower. My angst had faded away, and now I was feeling oddly buoyant. There is nothing like new pussy to put a spring in a man's step, I guess. The fact that she was a young, stunning creature didn't hurt either. I had long ago reconciled myself to the fact that I would never fuck anyone other than my wife. At least I thought I had, so all came as a surprise to me.

  I stepped out of the shower and checked myself out in the mirror. I still had a full head of hair, although it was more salt than pepper, which was also true about the hair on my chest and my pubes. I was a little soft around the middle, but otherwise in good shape. Good definition on my arms and legs. I stroked my cock a few times. It wasn't a bruiser, but it seemed well proportioned. Not a bad looking guy, I thought, especially for fifty-four.

  Fifty-four... oof. That made me literally three times Ashley's age. She was six years younger than my youngest son. If he brought home an eighteen-year-old, we'd think it was weird. What was I doing fucking a teenager?

  I closed my eyes and pictured her splayed out beneath me, my cock pistoning into her tight snatch. I could feel myself getting hard, and that's why I was fucking her.

  I went downstairs and made myself some coffee. I started to read the paper, but I just couldn't focus on it. All I could think of was Ashley.

  I let my mind roam, just delighting in it. The thought of being forever with such a delicious creature was overpowering. It was crazy, but maybe we could make a go of it. Joanne would kill me in the di
vorce. I'd lose all my… our friends. But I'd still be comfortable and able to make money, and I'd have Ashley.

  And then what? She'd go to a commuter college? We'd have kids at some point, and I'd be changing diapers into my mid-60s? And even if I still looked okay now, how long would it be until she got tempted by someone her own age? Or within thirty years of her own age for that matter?

  I laughed darkly, sanity returning. It was an impossible situation for both of us. I'd become an absurd creature, chasing around young kids when I should be retired while my young, hot, wife was probably fucking the pool boy. And it would be even worse for her. It would be unfair deny her the chance to make a life with someone more appropriate, to have a real college experience, to build a real life as young, poor, struggling newlyweds.

  This had to stop. But I didn't want to hurt her. Was she in love with me? She had to be, or at least infatuated, for this to happen. I needed to let her down easy, to explain why, as wonderful as she was, we couldn't have a life together. I'd have to apologize for taking advantage of her, explain that I'd just been caught up in the moment, but that it just couldn't be.

  I heard footsteps coming down the stairs, and moments later, she padded quietly into the kitchen. She looked ravishing. She was wearing one of my white, tee shirts and nothing else. Her hair was a mess, her blond locks tangled and jutting out at weird angles. She looked amazing.

  She gave me a wide grin and poured herself a big cup of coffee. She took a big sip and sighed happily. Then her smile faded.

  "What's the matter?" she asked. "You look sad."

  I took a deep breath, and launched into my prepared speech. "Ashley, you're a wonderful girl, but this just isn't going to work out. I'm sorry if I led you on."

  She gave me a puzzled look. I plowed on, "I didn't mean to. But we're just... we're just at too different a place in life for this to become anything. And I love Joanne, and I'm..."

  She started giggling. I stopped talking.

  "What? What's so funny?" I asked.

  "You," she replied.

  "Me?"

  "Yes, you, Uncle Danny. What'd you think? That I'm in love with you?"

  "Then what..."

  She approached me and climbed into my lap, straddling me. My cock twitched.

  "Then what do I see in you?"

  I nodded.

  "I see a handsome, experienced lover." She slowly began to grind against me. "A safe fling. Don't worry. I won't tell Joanne and I won't tell my dad."

  "You're eighteen. I'm... not. We can't do this," I said, as much to myself as to her, even though I could feel my growing erection pressing against her through my sweat pants.

  "Your wiener has other ideas."

  I laughed. "My wiener?"

  She giggled. "Oh, I'm sorry." Then she leaned forward, her lips near my ear. "I meant, your big… fat… cock." I was rock hard in an instant. She ground against me harder. "I want it in my hot… wet… pussy."

  My inhibitions vanished in an instant. She rose up on her knees, and together we fumbled awkwardly with my waistband until my erection popped out. She grabbed my cock and eagerly impaled herself on me.

  "Mmmmm, that's good," she cooed as she began to pump her hips.

  I looked into her big, blue eyes. I embraced her gently. This was our third time having sex, but kissing still felt tentative, awkward even. We kissed lightly, little fluttering kisses that very gradually progressed into a deeper, more passionate embrace. In a weird way, the kissing felt even more intimate than the sex.

  I leaned forward and sucked on her ear lobes and kissed down her neck. My hands slid under her tee shirt, and found her breasts. I tweaked her nipples, until she let out a throaty growl, her pussy spasming yet again on my cock, as she wrapped her arms around my neck.

  I reached under her ass and stood up, lifting her up. She was still impaled on my prick as I carried her out of the kitchen and into the family room, repositioning her on her back on the sofa. She wrapped her legs around my waist as I began fucking her in earnest.

  She was gasping and moaning. We both were, but her sounds were an order of magnitude sexier. I kissed her neck. She dug her fingers into my shoulders. She came again, her pussy getting even wetter. I'd already come twice in less than twelve hours, so I wasn't even close yet. Luckily she wasn't close to done either.

  I liked being on top, in control. I varied my pace. Slow, deep strokes mixed-in with quick shallow thrusts that began and ended with my cockhead teasing her clit. She came yet again and looked up at me with grateful, puppy dog eyes. That put me over the top. I exploded inside her.

  We lay there for a long while, panting. Her legs were still wrapped around my waist, and she wouldn't let me pull out, so I enjoyed the sensation of my cock deflating inside her drenched twat.

  "What do you like about having sex with me?" she asked.

  I chuckled. "You mean besides the fact that you're beautiful and, as far as I can tell, insatiable.

  She gave me a pout. "So, what? You're saying you think I'm just a hot slut?"

  My heart sank. I didn't want to insult her. Hurt her.

  "No, no Ashley, that not what I mean.... I mean...."

  She started giggling. "Chill out, Uncle Danny, I'm just teasing you."

  "You're a strange girl," I replied without thinking. "And a wonderful lover," I added quickly. "You're so responsive and so demonstrative. There's a lot of women who are, I dunno, too cool to admit they enjoy sex."

  "I enjoy it with you," she replied.

  I blushed.

  She giggled again. "Are you embarrassed? God, you’re so cute."

  I cleared my throat. "So, what do you like about having sex with me?"

  "You mean besides the fact that you're handsome and, as far as I can tell, insatiable?"

  I laughed.

  "No, seriously."

  She looked at me thoughtfully. "You know, I don't know what the fuck I'm doing. I've only.... I've only had sex five times before this weekend, with just two different boys. My first was Jimmy. He's a friend. Was a friend. I dunno what we are right now. But we were both in the same boat and decided to cash in each other's V-cards. It was okay, I guess. Awkward. You know, not painful like some girls say, but it was super quick. You know?"

  I nodded. "Give him time. He'll get better. The learning curve for boys is steeper at first."

  "Then the second was this guy, Trent. I know… like my dad. What are the fucking odds? He's older. Like twenty...."

  I winced at that. She grinned.

  "He's like the opposite of Jimmy. We hooked up for the first time at a pool party.... At Jimmy's house actually, which is why shit with Jimmy is so weird right now. He saw us ducking into the pump house together...."

  "The pump house?"

  She laughed, a delightful chuckle. "God, I hadn't even thoughts of that. But yeah, right, appropriate. Anyway, he was like the opposite of Jimmy. Super in control, which was hot at first. He put me up on a stack of boxes and just gave it to me hard. I mean, don't get me wrong, it felt good, but he had just one speed. And I don’t know. It almost seemed like I didn't really even need to be there. It was all about him. I gave him a few more chances after that, but it was always the same."

  I nodded again. "Yeah. I hate to say it, but you'll run into that a lot."

  She gave me a pouty face. "Maybe I'll just need to keep you on speed dial."

  I gave her a little kiss on the nose. I liked the idea of being her booty call.

  "Anyway," she continued. "It's totally different with you. You know, it feels like we're dancing together or something. I knew you'd be good. I watched you with Joanne more than once," she said blushing.

  "Your dad would keel over if he knew what sending you here for the month would do."

  She laughed darkly. "No. He'd kill you. Well, if he got to you before Mom did."

  I frowned.

  She laughed again. "Don't worry. He'd kill me too, assuming he got to me before Joanne. So I guess we'll just have to keep t
his our little secret, huh?"

  "That's probably a good idea," I replied quietly.

  ***

  The day passed quietly. I hadn't seen Ashley in a while, and when I check in on her in her room, she was napping peacefully.

  As I went about various household chores, I was happy, almost giddy. I was not under any particular illusions. Odds were this would end badly, very badly. There would be tears, if not blood. But all of that was in the future, and for right now I was sharing my house with a gorgeous, young, woman, who was funny, good company, and who seemed against all logic to be happy, eager actually, to have no-strings-attached sex with me. For a man my age, with a few bucks in the bank, it was better than winning the lottery.

  Late that afternoon, I returned from food shopping to find Ashley in the kitchen on her computer. She was recently showered, fresh faced, looking almost obscenely attractive in just yoga pants and a clingy tee. She helped me put away the groceries and we chatted about nothing in particular, celebrity gossip, movies. We talked about college. She was excited, but a little anxious. I told her a few of my freshman stories. She laughed at what a geek I'd been.

  I made dinner, braised lamb shanks, and she helped me with the homemade pasta. For a little thing, she had a good appetite and thankfully was a committed carnivore. It occurred to me that she'd one day make her husband very happy. The thought triggered in me a small twinge of jealousy, but it quickly passed. That too was in the future.

  I debated opening a bottle of wine for dinner, but then I realized that giving an eighteen-year-old some alcohol was surely the least of my recent sins. We ate, and her second glass got her pleasantly silly. She started teasing me about my minor OCD -- I'd probably moved all of the groceries she'd put away to put them in the "right" place -- giggling at her own jokes. I teased her about being a slob. Her clothes were scattered all over her room. It was fun, oddly comfortable.

  After dinner we retired to the family room and watched TV. We both got a kick from reality game shows. America’s Got Talent. The Voice. That kind of stuff. She liked to pretend she watched them ironically, but she knew way too much of the back-stories for that to be believable.