Midlife Glitch (May/December Romances Book 1)

by Boswell, Ben

  "I'm sorry. I didn't mean to upset you," I said. I reached out and touched her forearm.

  She laughed and wiped away tears. "You didn't. That's just, like, one of the nicest things anyone ever said to me."

  I smiled at her.

  "I need to find an eighteen-year-old version of you," she added.

  "And that's one of the nicest things anyone's ever said to me."

  We finished our dinner mostly in silence, just looking up at each other every once in a while, both of us, I guess, wrestling with our emotions. Part of it was the music in the background. I'm not a big jazz fan. I don't know any of the artists or songs by name, but over the years I’ve put together a playlist of tunes that somehow move me. We were listening to a melodic piece, sax and piano, that somehow fit the mood.

  I held out my hand to Ashley. "Would you like to dance?"

  She smirked. "To this?"

  I nodded. "Give it a try."

  I pulled her into my arms and we swayed slowly together. She put her arms around my neck and rested her head on my chest, my hands encircling her hips. Even in heels she was a lot shorter than me, but she felt good in my arms. I kissed her on the top of the head. She looked up and stood on her tiptoes. We kissed softly at first, then more passionately.

  She ran her hands through my hair. I reached down and kneaded her hard butt. She pressed firmly against me. I could feel her soft breasts, her hard nipples through my shirt. Her dainty hand slid down between us and she rubbed my crotch forcefully, her fingers gripping my rapidly stiffening cock.

  I took her by the hand and led her upstairs. In the bedroom, we kissed and I began to undress her. She was wearing her sexiest underwear, a tiny pink thong and matching bra. She kicked off her heels and lay back on the bed. I uncovered one breast at a time, kissing and sucking her nipples. Then I trailed my tongue down between her mounds and across her flat stomach. I slowly pulled off her thong, massaging her legs. Then I stood back up to admire her gorgeous, young body. She opened her legs wide and spread her pussy for me.

  I stripped quickly and climbed on top of her. She grabbed my cock and guided it inside her. I made love to her slowly, passionately, sharing deep, wet kisses the whole time. She came more than once, her spasming pussy clutching at me as she gasped and sucked on my tongue.

  I rolled over onto my back and pulled her on top of me. She sat up, hands on my chest, and slowly rode me up and down. As she did, I explored her body with my hands, cupping her full breasts, teasing her erect nipples, squeezing her hard ass. I traced her lips with my finger, and she took my thumb into her mouth, sucking on it in time with her movements. She came yet again, while grinding her pelvis against mine. She collapsed forward, her mouth next to my ear.

  "I'm done," she sighed. "Come inside me."

  I grabbed her butt and thrust upward harder. She was gasping and moaning right in my ear, her hot, moist, breath on my neck. I slid my hand between her cheeks, my finger tickling her ass. She moaned louder, encouraging me. I remembered how she’d reacted when I’d tongued her anus. I pressed my middle finger firmly into her butt.

  "Oh fuck!" She growled lustily.

  She started bucking up and down, her sphincter pulsing on my finger. I could feel myself inside her through the skin separating her ass and her pussy.

  "Oh Jesus," I moaned as my body tensed up and I came inside her, squeezing her tight.

  I went limp back on the bed and withdrew my finger from her bottom. She collapsed on top of me.

  "That was... interesting," she said. "A little like getting an electric shock... but in a good way."

  "I'm glad you liked it."

  "I did," she moaned. She started grinding against me. "It's still early."

  I laughed. "Ashley, this is why you need a younger man. I'm cooked."

  "We'll see," she replied with a smirk as she ducked under the covers.

  She swallowed my slimy dong into her mouth and blew me wetly. It felt good, so good, but there was no way I was going to get more than a partial erection, not so soon. But she didn't seem to mind as she continued to work my cock and balls with her mouth.

  I felt her wet finger tickle my asshole. I tensed. I'd never been into that. Latent homophobia maybe, unpleasant associations with rectal thermometers and prostate exams, general squeamishness, whatever. But I was hardly in a position to object given that I'd just shoved my own finger in her ass, and anyway, her lips on my dick had me in a compliant mood.

  She pressed her finger into me. More gently than I had done, but it was still a jolt. It was a little uncomfortable and felt more than a little gay, but the combination of her mouth and tongue on my cock and her finger thrusting in my ass was enough to get me hard, at first just a noticeable stiffening, but surprisingly soon a full blown erection.

  She reappeared from under the covers with a big grin, "see, I told you."

  She got up on her hands and knees, waving her little ass at me. I didn't need any more encouragement. I kneeled behind her and pressed my cock into her steaming snatch. She was sloppy wet, literally so since I'd finished inside her just a little while earlier. It was all over my shaft, on her thighs. I decided to continue our little experiment in ass play. I coated my thumb with our combined juices and pressed it into her butt.

  Just as before, it was like flipping a light switch. She backed up against me hard, over and over, fucking me harder than I was fucking her. I reached around with my other hand and touched her swollen and hard clit.

  She growled and flung her head back, her long blond hair slicing through the air. She looked back me over her shoulder, her expression fierce, feral.

  "You can do anything to me," she grunted through clenched teeth. "Anything!"

  I knew what she wanted. I wanted it too. All that stuff I'd told her about self-respect and not selling herself short and not having to accept porn conventions... all that went out the window in that moment of animal lust.

  I pulled my dick out of her pussy and placed it against her tiny puckered asshole. Any doubts I had about what she wanted vanished as she pressed back against me, taking my cock inside her. I thrust forward, finishing the job.

  She let out a lusty growl and began pumping her ass back and forth, sodomizing herself with my cock. It set me off in a way I’d never experienced before. It wasn’t just the physical sensation of her tight ass pumping up and down my shaft, it was everything: the visual of my cock spearing her tight hole, the taboo of it, and mostly her reaction, lusty, feral.

  I grabbed a handful of her hair and yanked it roughly. With my other hand I slapped her ass hard, harder than I intended. It was like a gunshot. But that only seemed to turn her on more. She reached between her legs and shoved two fingers into her pussy, finger banging herself roughly. I spanked her again and again, back and forth on each of her perfect ass cheeks.

  She suddenly reared up, her back impossibly arched. She didn't even make a sound, but her body shuddered so violently I thought for a second it was a seizure, and then I felt her ass clamping down on my cock rapidly. She took a sudden gasping breath and then fell forward onto the bed. I started to follow her down. I wasn't done. But she put her hand between us.

  "No more," she gasped, "no more."

  I sat back on my heels, surprised at how hard I was breathing and sweating.

  "Did you?" She asked.

  "No, but that's okay," I replied catching my breath in deep gulps.

  "Come on," she said, taking me by the hand and pulling me off the bed.

  She led me into the bathroom. Joanne and I have a big, two person shower, with wall jets and a waterfall showerhead. We turned on everything, real hot and climbed in. She sat me down on the bench and kneeled before me. She cleaned my cock carefully and then took it deep in her mouth.

  She wasn’t in any rush. She took her time, licking me up and down and then swallowing me deep. She sucked my balls gently. Then she leaned into my lap and took my cock between her beautiful breasts, bouncing up and down, fucking me with her clea
vage. She stared up and me, her big blue eyes watching me unblinking.

  I came again, my cock pulsing almost painfully. My jism splashed across her face and dribbled down her cheeks onto her breasts.

  She laughed. "That was more than I expected."

  I couldn't even reply.

  I grabbed a washcloth and began to clean her off. I wiped off her face and kissed her on the lips. I soaped up her breasts and gently kissed her nipples. I stood her up and carefully cleaned between her legs. Her pussy was swollen and very sensitive. Her ass was worse, covered in my handprints, and her anus was an angry red. I kissed both gently.

  I stood and hugged her close, neither of us speaking. Between the wine and the sex and shower, we were both exhausted. We dried ourselves off and stumbled into bed naked, both of us asleep in minutes.

  ***

  I woke up in the middle of the night in the midst of a panic attack. Wracked with guilt I woke her up.

  She gave me a groggy grin, "Oh God, you really are insatiable."

  "Ashley, I'm so sorry. I don't know what came over me."

  "Huh?"

  "Tonight. It... I... I've never been like that. I can't believe how I treated you."

  She smiled. "Did it seem like I didn't enjoy it?"

  "No, but..."

  "No buts. We're two consenting adults. And you stopped the second I asked you to."

  I almost debated the consenting adults part. She was still just a kid, even if she didn't know it. An eighteen-year-old kid, but still a kid. And I was a pervert. A monster. An abusive, perverted monster.

  "No man should treat you that way. You shouldn't let them."

  She reached out and brushed my cheek. "Even if I enjoyed it? Anyway, I know you'd never hurt me."

  "How can you know that?"

  "I just do."

  "We can't do this anymore," I said sadly. "We have to stop."

  "That's going to happen anyway. Joanne is going to be home soon. And anyway, in two weeks I'm off to school. But there's no reason we can't enjoy this for now."

  "It's wrong."

  She sidled up to me, her naked body pressing against mine.

  "Make love to me," she said simply, throwing a leg over my waist and kissing me softly.

  We made love slowly, face-to-face, side-by-side. Her body was warm, soft and responsive. She came beautifully, with a delicate shiver, a big smile, and a small tear of joy running down her cheek. I climaxed as well, and we fell back asleep in each other’s arms.

  Chapter Seven

  Monday morning, we both had to get to work, so we rose briskly and got out of the house. I had a couple of morning status update meetings, then a business lunch, and then a meeting with our accountant. Boring stuff. Except, suddenly it wasn't so boring.

  The first text came at 9:43am while I was watching an endless PowerPoint about trends in commercial real estate inventory. It was from Ashley. For a second I was worried something was wrong, but instead I was greeted by a picture of her holding a sign, "thinking of you" written in cute high school girl loops, little hearts over the "i"s.

  "Me too," I texted back.

  At 10:24, another text. "Got a ten minute pedi on coffee break." It was accompanied by a picture of her sexy little feet and her new, bright red, nail polish.

  I sent her a picture of my loafers.

  10:27: "LOL, my pic was cuter."

  11:13: "I hate wearing a bra," accompanied by a down blouse shot of her cleavage.

  I didn't have time to answer before the next one came.

  11:15: "So, I decided to air them out," accompanied by a close up of one of her perfect, naked, breasts, capped by a beautiful erect nipple.

  "My pants are getting tight," I replied.

  "Pics or it didn't happen," she answered quickly.

  But somehow, no matter how boring the PowerPoint, I figured someone would notice me taking a crotch shot of myself.

  "Guess you'll have to find out for yourself later," I wrote.

  "Mmmm," she texted back.

  12:43, while I was at lunch. Another text from her. "Just noticed I had panty lines in this dress. So I had to take them off." Attached was a picture of cute, white panties in a desk drawer.

  I excused myself to go to the bathroom. I stroked myself to a respectable size and sent her a picture of the bulge in my boxers, my first experience with sexting. "Okay, you win," I texted back.

  1:26: "UNCLE DANNY! OMFG what kind of gurl do u think i am?"

  Then two minutes later, "Just kidding. Getting me hot."

  I went to my accountant meeting, and he started going over our finances and estimated taxes for the rest of the year. I was already more than a little distracted when my phone started vibrating in my pocket with incoming texts. I checked them as surreptitiously as possible.

  2:21: "Can't stop thinking about you. Need to do something about it."

  She followed that with a series of selfies, each about two minutes apart.

  >>A picture of her sitting on a closed toilet, centered on her dress-covered legs.

  >>Same location, but now the dress was pulled way up, showing off her creamy thighs.

  >>Now the dress was bunched around her waist. Her legs were together, but her tight, little slit on display.

  >>Legs spread now, the image centered on her pussy.

  >>Her hand rubbing her lovely snatch.

  >>Her pussy penetrated with two fingers.

  >>Her snatch spread wide, glistening, her fingers slick as they bracketed her clit.

  My blood was boiling with lust.

  "Bill," I said suddenly, interrupting him mid-sentence, "listen, I need to take care of something. I'll call to reschedule."

  He gave me a queer look. "Um, okay Dan. You sure everything is alright? You look a little flush."

  "I'm okay. Just... Look, I'll call tomorrow to reschedule."

  Holding my folder over my crotch, I speed-walked out of the room.

  I got in my car and pulled out my phone and sent a text to Ashley.

  "Come home NOW!"

  She texted back right away, "LOL. Can't I'm @ work"

  "Tell them you're not feeling well. I want you."

  She made me wait five minutes for a reply.

  "Guess you liked those pics?"

  "Yeah, a little," I replied. "Come home now. Don't make me beg."

  "Okay okay, I don't want you to compromise your dignity."

  "Too late," I texted back.

  It was another couple of minutes before she replied, "Okay, leaving now. Usual pick up?"

  "I'll be waiting."

  I drove to the subway station and parked with a view of the exit, going back over her texted pics as I waited. Finally she appeared and strode to the car with a big grin on her face. She climbed in and I drove off.

  I wanted to kiss her hard, but couldn't risk it. Instead I snaked my hand into her lap and between her legs.

  "You're a bad girl," I hissed as my hand found her wet gash.

  "Are you gonna span.... Ooh," she moaned as I shoved two fingers inside her.

  "Are you always like this?" I asked as I fucked her with my digits, my thumb now rubbing her clit hard.

  "Is that what you want to hear? That I'm a dirty, horny slut?"

  I groaned at words.

  "Or do you want to hear that it's all you that's getting me so turned on?"

  I groaned again. She seemed to have an almost instinctive ability to push my buttons.

  "Oh god, you're gonna make me come," she moaned before I could answer. And a moment later, her pussy began pulsing on my fingers as she gasped with pleasure.

  She pushed my hand away and immediately draped herself over the center console, her head in my lap. She pulled down my zipper and fished out my cock, swallowing me deep.

  Road head was another first for me, and it was such a turn on that I brushed aside the alarm bells ringing in my head. This was reckless on so many levels that I couldn't even process it. The risk of an accident paled in comparison t
o the possibility of being seen. We were driving around my neighborhood, and anyone getting close to the car could easily see what was going on.

  Luckily, the streets were quiet and we made it home without incident. I parked in the driveway, and was tempted to let her finish me off, but instead I forced myself to stop.

  "Let's go inside," I growled.

  I fixed myself up as best I could and then she and I walked stiffly to the door, both of us acting as nonchalant as possible.

  Once inside, though, we were immediately at each other. We kissed hard. Then without a word, I spun her around and shoved her face first against the door. I reached down and lifted her dress. She bent at the waist and jutted out her perfect, little ass. I dropped my pants and with a rough thrust buried myself inside her hot, tight pussy from behind.

  I fucked her hard, virtually lifting her off the floor with each stroke. She was gasping and moaning loudly. I reached under her dress and roughly mauled her breasts, gripping her nipples and stretching them out. She mewled in pain, but she obviously loved it, her hand now sliding down to frig her clit as I banged her hard.

  Anyone walking by would have heard the door rattling as I slammed her against it over and over. And if they came closer they would surely hear our intermingled moans, and slap of flesh on flesh. I was so worked up that I didn't last more than a couple of minutes. I came suddenly, hard.

  I felt lightheaded and leaned against the door to support myself. Ashley disentangled and dropped down to her knees, taking my slimy prick into her mouth, teasing out a last few drops of jism.

  "Mmmm, I like tasting myself on you," she cooed.

  That sent a jolt of excitement through me. I shook my head.

  "What?" she asked, rubbing my member up and down.

  I chuckled. "Behind that angelic face, you have a lot of dirty thoughts."

  She stopped stroking me and got very serious, "you have no idea."

  The moment passed before I could respond. She gave me a saucy smirk and took me back into her mouth.

  My phone rang. Since my pants were pooled around my ankles, she was closer. She reached into my pocket and recovered it. Ashley nonchalantly handed it up to me even as she continued sucking me off. It was Joanne.