I should have been ashamed of myself. At sixteen, Jon was one-quarter my age. And he’s Jon – not ‘Jonathan’ like a grandmother might call him, or ‘Jonny’ like a mother, but ‘Jon’ like an adult. God knows he was more mature than most of the men I knew.
We were sitting together on the couch, watching television. That’s where he slept whenever things weren’t good at home and he crashed here. Sometimes late at night if I was awake, I would steal out and watch him. He was beautiful, with broad shoulders and a strong back. He slept in a t-shirt and boxer briefs. Don’t ask – I just know.
I shifted a little closer, hopefully not too discreetly. He was my grandson’s best friend; that’s how we knew each other. He had his classes, of course, and smart as he was, some school subjects were harder than others so I tutored him in exchange for his doing odd jobs for me. Like any teen, he hated to get up early so I suggested that he shower after he helped me clear the table after dinner.
We chatted about his day, the good and the bad, and he was always interested in mine. I let my hand fall from my lap and onto the cushion between us – he was still too far away to accidentally touch his leg.
I set my empty wine glass aside. I never offered him any and he never asked. I tried to keep drinks that he liked in the refrigerator but he usually just filled a bottle with tap water and that’s what he was drinking that night.
Jon reached his arms out in front of himself and stretched his muscles. When he settled, his leg brushed against my hand. I honestly hadn’t been so excited about a man’s touch in a long time and convinced myself that he did it intentionally. I had stopped asking him about girls at school; he only shrugged when I did. He dated, but there was no special one.
He was wearing jeans, a tee, and socks, and I was still in my skirt and blouse from work. My pantyhose were off and one extra button on my blouse was undone. In my defense, I had always done that when I got home. He didn’t know that I caught him looking at my chest once, and after that, I hoped for him to do it.
Then his hand dropped limply onto mine. I froze. Maybe it was an accident. Maybe he was embarrassed and didn’t want to call attention to it. Maybe I should have acted my age instead of his.
Then he moved just a little. I did too and caressed the back of his hand with mine until we intertwined our fingers, holding hands backward. I sighed and glanced from the corner of my eye. He was smiling.
I scooched even closer and rested my head on his shoulder. I desperately wanted to know what he was thinking but I had learned long ago not to ask men that. Then he pressed his lips against my hair.
“That was nice,” I said and took his palm in mine. He squeezed it and I squeezed back. I tucked my bare legs under my tush and snuggled in. We stayed like that for a while. I hadn’t felt that kind of attraction or affection for too many years.
Jon was probably sitting just like that with a girl his own age not too long ago. Thinking like that made me jealous but also hopeful. I wondered whether he might have thought of me as a date. Would he make a move? I resolved that I would not. I would not seduce him.
I could have taken that moment to the grave and been happy about it. That would be better than having my saggy tits and baggy ass repulse him. They’re really not, not much, but they are when compared with pert and perky, firm and cellulite-free high school girls. Someday they’ll be where I am, but I’ll never go back to what they were.
I would compare. I will. Jon has no gut. His hair is thick and his lashes are long. His hands are strong. His cock won’t need constant attention or blue pills.
“Are you okay? Are you cold?” he asked.
His voice, not quite the bass it would be someday, startled me. “Yes. No. I’m fine.” I placed my free hand on his leg.
“Good, because, you know…”
“I know. I hope I know.” I looked up at him and willed him to kiss me. My lips parted with anticipation but I refused to lean in first. He nodded his head forward, I lifted my chin, and he kissed me. It was a small one and assured. He pulled away and, with my eyes still closed, I waited for the next one. Our lips found each other again and I opened my mouth to invite his probing tongue.
He wanted this. The way he kissed me and the way he held me shouted that he wanted this as much as I did. I broke off and gazed into his eyes the way new lovers do, then pulled his lips back to mine before he could see my eyes well up. He thumped the couch cushion to find the remote and turned the television off.
The remaining dim light came from a small lamp on the other side of the room, and I was grateful for that. Jon’s steady hand squeezed a breast on top of my blouse – he was feeling me up! I don’t know what his generation called it but I hadn’t been felt up for years and it was delightful. Old women don’t get felt up, young ones do.
He inched my blouse out of my skirt and massaged my back above and below my bra. With a snap of his fingers, he unhooked it and the cups fell away from my heavy breasts and stiff nipples. He moved to the front again, took a tit in hand, and we groped each other on the couch that was his bed.
I kept my lips pressed against his, unbuttoned my blouse, and discarded it and my bra to the floor. He took one nipple into his mouth and then the other and back again. I clawed at his shirt and pulled it over his head and tossed it next to mine. I kissed him skin-to-skin, squishing my squishy tits against his hard, almost hairless chest.
“Are you sure?” I asked as I nuzzled his neck.
“About…”
I gave him a knowing look. He knew exactly what I meant.
“Why wouldn’t I be? You’re beautiful. Your eyes are beautiful. You’re sexy as hell. How could I not want you? You’re a real woman and, you know, if you’ll let me.”
He was right. I rubbed inside his thigh to signal my intentions as we necked and I cupped his prominent erection. I unbuttoned his tight jeans and struggled to get his zipper all the way down. There wasn’t much room for me to wedge my hand into his underwear although I tried my best.
I silently mouthed my thanks when he lifted his cute butt and slid his jeans down. I motioned for him to keep going and his boxer briefs followed with a shy smile. My God, it looked hard. I flinched when it flexed to oust another bead of pre-cum. I wet my hand with it and the one that followed and stroked his long, thick cock; it was even harder than it looked. He leaned back and I rested my head against his chest.
“Do you like this?”
His eyes stayed closed as he nodded. “Hm-hm.”
I climbed onto the couch and kneeled on the cushion. I got more aggressive before taking much of him into my mouth. I swirled my tongue around his cock, relishing his savory masculinity and the sweetness of his youth.
He moaned for me and played with my dangling breasts, pushing them up and pulling them down. I wanted this to be good for him. I wanted him to forget the other girls and I wanted him to forget how old I was.
His cock was slick with my spit and I jerked on him again. I kept him slippery and rubbed him faster with the intent to watch it when he came. My pussy was weeping for her own attention but this was all about Jon right now.
“I’m going to lose it,” he said.
I gave him another suck and redoubled my strokes. “Don’t hold back, okay?”
He moaned again and his taught abdomen tightened. I stopped but didn’t let go when he did. I felt his cum as it rose through his cock and marveled as to how high it jetted before splattering down onto his chest. One white creamy spurt followed another until I squeezed the last drops out onto my fist.
My grandson’s friend was spent, obviously happy about it. I was too but not as happy as I would have liked. I wanted my turn and yet funny as it sounds, I didn’t want to seem easy. Suddenly, he yanked me on top of him and hugged me.
“Mary, that was great! Thank you!”
“Careful,” I said, “We don’t want to smear this mess I made.” I swept my blouse from the floor to clean him up but he grabbed my wrist.
“Don’t stain your shirt! Use mine.”
Why I didn’t have a box of tissues nearby for a sixteen-year-old, I’ll never know. “We don’t need to get yours soiled either.” I hoped that I wasn’t getting too dirty when I dipped my tongue into the sperm spot closest to his cock. His wide-eyed reaction showed that he was okay with what I started so I finished, slowly lapping my way up the trail until it was all gone.
I kissed him up and down his torso and played with his privates. I didn’t think I’d have any trouble getting him fully firm again very soon. He laid me onto my back and rubbed me over my skirt. I hiked it up a little and put his hand underneath. I moaned as he pressed the fabric of my wet panties between my lips and I writhed under his touch.
“Would you like to take me to my bed?” I asked. He mumbled his reply but he was clear enough. I was self-conscious about the way my breasts hung – they look so much better in a bra – but his cock strongly, strongly implied that he liked them as it pointed the way toward my bedroom.
We kissed at the foot of the ready bed. I turned my back to him and asked him to unzip my skirt. His hands were shaking a little which made him all the more endearing. I stood in only my panties and hand bra, facing him. He wanted me to take the lead, I thought, so I shimmied my panties to join the skirt at my feet.
His eyes fixed themselves down there which made me wonder about the girls he had been with. They probably all shaved or waxed or whatever was expected of young women his age. Mine might have been the first hairy cunt he had ever seen up close.
I eagerly kissed him, hoping my mouth and tongue weren’t overly anxious. I felt his young cock fill itself, pressed between my legs. I wasn’t the only eager one. He might have taken me standing there if I hadn’t broken the kiss to choose a side of the bed. He joined me from the other side and we embraced under the sheets.
Our hands explored each other’s bodies. His was smooth and muscular which made me the luckier of the two. I rolled onto my back to give him better access to my wet pussy. His fingers played with my pubic hairs before splitting my slit and probing me.
He was good, and I might have let him make me cum that way, but that wasn’t what I really wanted. He took my hint when my leg slid under his, and he climbed on top of me. He lifted his hips a little and attempted to enter me with jittery, gentle jabs. He didn’t know what he was doing.
That I was about to take his virginity scared and excited me. I took hold of his cock and slowly, easily slid it in despite its girth. He moaned and froze. I moaned and humped. His was the stoniest cock that my cunt had had the pleasure of hugging for the longest time and I squeezed my muscles around it the best that I could.
He pulled out a bit and pushed it back in. He was being tender – too tender. I was somewhat ashamed that I had put myself under him for a fuck and not for him to make love to me. As good as it felt, I wanted more. “Don’t be too easy with me,” I told him.
Inexperience be damned, he should have been paying attention to the flooding testosterone telling him to thrust deeper and hump faster. “Do you think I’m too old for this?” I asked with a scowl while pushing him off of me.
“What? No!”
“You do! You think you’ll break me if you fuck me like you do your girlfriends.” I let him stumble over his words, sure that he was trying to decide if he should tell me the truth.
“I, no, you …”
“Then don’t fuck me like you’re an old man!” I grabbed his cock, stuffed it back into my cunt, and gave his ass a hard slap – his tiny, cute, round, firm dimpled ass.
He responded to that and to my encouraging moans and groans. “That’s it – you won’t break me, boy!” Eventually, he found his rhythm and stopped pulling it too far out. My young lover was getting me close. “Don’t you dare stop!” I screamed as I arched my hips off of the mattress. He kept thrusting and I kept cumming with an overwhelming orgasm borne from the sinful wrong of claiming such a young man.
Jon kept fucking me and I kept fucking him back. I wanted to cum again and I wanted to feel him when he exploded inside of me. I wanted full-blown illegal-in-my-state fireworks. I wanted firecrackers popping in my cunt and not the short-fused sparklers that I got from men my own age.
His thrusts slowed and he pushed against me, grunting, until his pulsing cock emptied itself. I got what I wanted – forceful spurts of semen against my walls triggering my orgasm that merged with his. We were drenched in sweat – his, mine, and ours.
He rolled off and I quickly covered up lest he sees my body post-clarity and not through the eyes of a horny young man.
My eyes, however, were fine.
We each glanced away from the ceiling and pretended that we hadn’t caught the other. I wanted to cuddle, I wanted to thank him, I wanted a hundred other things other than the guilt of taking his virginity. I was afraid that he hated me and that he’d tell my grandson. I wanted to do it all again.
“That…you…” he said without looking at me.
“I know.”
“I guess I should get back to the couch. I have school in the morning.”
I touched my head to his shoulder. “You could stay here. There’s room.” I took a deep breath and exposed my flat behind when I climbed out to put on my least matronly nightgown. After a quick pee and clean-up, I returned to find that he was still in my bed. He had retrieved his t-shirt from the living room floor and my blouse and skirt were crudely folded on my dresser.
I re-joined him and we kissed for a while. “We should sleep. Work, school…” I kissed him once more and rolled onto my side, where he gave me the cuddle I wanted. “Jon?”
“Yeah?”
“You can’t tell anybody. My family can’t find out or yours either. I know Nate’s your best friend but he’ll tell his mother – my daughter. Boys brag; men brag.”
“I know. I won’t, I promise.”
“You say that, but it’s important.”
“If I tell, then I won’t be able to come back.”
~~~
I didn’t sleep much. I loved having a man in my bed again, especially one who didn’t snore. I brooded all night over how I should break up with him or how he’d break up with me. Something as simple as a second toothbrush could expose me and I’d need a story to deny it. There must be fifty ways to hide your lover.
Mostly I planned when his next sleepover could be, knowing full well that our relationship had no future after that, or the one that followed, or the one that followed that.
Time crawled in and out of my tosses and turns until a little after five. I’d have to get up in less than an hour anyway but he needed his sleep. I shouldn’t, I forced myself to think as my hand found its way into my panties – my granny panties. I lazily played at first but there he was with the covers down to his waist and I couldn’t help but relive last night. I tossed my panties onto the floor – I didn’t want him to see them anyway.
I wondered what he would think if he caught me watching him as he slept with my fingers up my pussy. I should have gotten up to shower and I was going to, right after I took a little peek. I carefully drew back the covers and saw his cock outlined in his briefs. Morning wood. He might have been dreaming about me and he might not have. I decided to take things into my own hands, so to speak, because I didn’t bother to use my hands.
“Jon? Are you awake?” I whispered as I hiked my gown up, climbed on top of him, and rubbed my pussy against his wood. He stirred and smiled.
“I am now.”
“Shh,” I said as I tugged his underwear down. “You can go back to sleep if you want. It’s early yet.” I wet his cock with my juices and reached to guide him in. “That’s it. Shh. Relax. Let me do this.” I started sitting up but then I lay on him, placing all of my weight on his chest as I ground him in and out of my pussy.
His instincts told him to thrust. “No, no, let me. Oh, yes, that’s it. Like that.” I got him to ease off, mostly, and I used his cock to enjoy a slow, morning fuck and the gradual build-up that came with it. Soon, slow wasn’t what I wanted. I was mashing my clit against the base of his cock as fast as I could until my climactic whimper.
Poor Jon hadn’t cum and I think he was still afraid to move after I told him to be still. I’m nothing if not fair. I tenderly lifted myself away from his meat and replaced my muff with my mouth. “Don’t hold back,” I said between bobs. “I’ve got to get ready for work.”
I didn’t have to lick, suck, or stroke for long. “W-watch out…”
I bobbed faster.
“I mean it,” he puffed.
I bobbed even faster until he groaned and released his load. “You let me do it in your mouth!”
“At my age,” I spouted, “I’ve found that that’s a lot easier than cleaning up the mess.”
I reminded him that he only had a little while to doze before Nate came to pick him up.
“Mary?” He had that look. I knew what he was going to say and hoped I was wrong. “Mary, I love you.”
“No, you don’t,” I stated and left him to go shower. Forty-nine years ago, I would have gushed. I might have said it first. Now, all it did was add to my guilt. He was still in bed when I came out with a towel wrapped around me, and I sat with my back to him to put my makeup on.
He was quiet for a while before saying, “Sorry.”
I didn’t want him to say that either. “Don’t be sorry, but don’t fall in love with me. Turn around, I have to get dressed.” As good as last night was, and this morning, and as young as he made me feel, I regretted what I had encouraged.
“Turn around? You and I just…”
“Turn around or get out.” I looked over my shoulder and removed my towel. “I have plans tonight so you shouldn’t come over.”
“Why don’t you want us to be in love?”
“Because you’re looking forward to the prom and I’m looking forward to retirement.”
“I don’t care.”
“You will. You should.” I detailed every sound reason why we shouldn’t be doing this at all. He twisted back in my direction again. I was half-dressed so at least he hadn’t seen me completely naked in the daylight. I was running late and my grandson would be here soon. Jon tried to kiss me and I shooed him away.
“Get dressed. You don’t love me. You love that I fucked you. You’ll fall in love with every girl who touches your cock and probably already did. It’s the way men are made.”
“You’re not being fair.”
That shook me; My children and even my grandchildren must have said that to me a million times. “Fair? Okay, let’s be fair. Date. I want you to date. Date cheerleaders or library nerds or your mother’s best friend – I don’t care. You bring them here and you lay them on that couch. Every time that you don’t fall in love with each other, then you can come to bed with me. Is that fair enough?”
Jon never answered me. He got dressed and picked up his book bag to leave. He hovered by the door, then dropped his bag at my feet and took me in his arms. I turned my head and played at pushing him away but I eventually let him kiss me – a long, loving kiss.
A knock at the front door made my heart jump – it was my grandson. Thank God we weren’t by a window.
Nate kissed me on the cheek when I let him in.
“Jon! Move it, lard ass! Oops, sorry, Gramma.”
“Lock up when you leave,” I told them as I walked out.
“Love you, Gramma!” Nate called out after me.
“I love you too, Nate.”
“Love you!” Jon copied.
I paused by my car. “I love you too, Jon,” I said to myself.
“Dude!” I heard Nate exclaim, and watched as he shoved his friend. “Go get your own gramma.”
