[FM] I lost my virginity to a DILF

Sex is something that has always made me a little uneasy to talk about. So this is a little bit therapy for me, as much as I want you all to also enjoy what I write.

I guess by way of introduction, my name is Taylor. I’m 22-years-old. Im 5’5, blonde, and have DD implants. I was blessed with itty bitties, and while I know that might be what some guys go for, it was a point of insecurity for me growing up and in college. So when I had saved enough money, I got myself some boobies and my body confidence shot up.

I went through all of high school without much of a dating life. I had crushes, of course, but I was definitely what most would call a late bloomer in the looks department. I had braces and big thick glasses, and I was on the thicker side. I’m pretty much opposite now: a gym membership, Invasalign, and contacts will do that for you. It helps that I also learned how to apply makeup and style my hair so it was less, well, poofy.

Anyway, that’s pretty much me. I don’t have much of a sex life. I can count on my hands the number of people I’ve had sex with to date, so I’m probably less experienced than many people reading this, but some of my experiences have been pretty unique and exciting so I figured I’d share. If you’ll have me.

This is getting a bit rambly. Sorry.

I didn’t abstain from sex on purpose. I wasn’t looking for the right guy or anything. I was just . . . kind of a dork.

In college, after my boob job—I was 20– I became good friends with James, a 6’1 jock type with big brown eyes and just incredibly sexy. I was so into him, but like every other guy, he just looked right through me. He started dating another girl and we stopped hanging out.

I was depressed. Fortunately, one of my friends convinced me to go out to the mall with her and some of her friends. One of those friends was a slightly older man named Harvey. Harvey changed everything for me that night.

Harvey isn’t exactly the kind of man I thought I would lose my virginity to. For starters he was nearly a decade older than me, recently divorced, with two kids. He was cousins with one of my friend’s friends. Though he certainly was easy on the eyes. He was tall, and clearly quite muscular. And I may have glanced at his bulge . . . Ok, and his ass, which I wasn’t dissatisfied with. I couldn’t help but imagine being the object of his passion.

Going into that night, I would have never entertained even fantasizing about a man much older than I, unless that man’s name happened to be George Clooney or Brad Pitt. But once I started to get to know Harvey, I knew I’d be jilling off to the thought of him that night – that is, if we hadn’t fucked instead.

Harvey was outgoing, kind, happy, driven, and overtly sexual. For whatever reason, he seemed to like me too. I had it bad for Harvey, which led to me doting on him more with each drink. I’m such an idiot—I’m sure he thought I would be such an easy lay. And I was, for him anyway.

We didn’t pay much attention to anyone but each other at the mall. We’d go into stores together and goof around. It was just so easy, being around him. We told each other about ourselves and, how we knew the friends we were with that night. I found out that after his divorce, he was just looking to have some fun. He wasn’t too interested in giving his kids a new step mom.

The kids were sleeping over at his ex-wife’s house, which made his house pretty empty.

It got a little awkward when we brought up our sex lives. Mine being virtually nonexistent other than my vibrator who I affectionately call B.O.B (battery operated boyfriend), I was tempted to lie about it, but I didn’t. I ended up telling him I was a virgin. Better to be proud of it then ashamed, I thought.

“Is that by choice?” Harvey asked.

“Not MY choice,” I laughed awkwardly.

“It wouldn’t be my choice for you either!” Harvey said instantly.

“Oh,” I said, blushing wildly and pretending to be interested in some shoes at one of the department stores we wandered into. I didn’t know what else to say and changed the subject.

We stayed there until the mall closed. Harvey was walking me to my car in the dark after we split from everyone else.
Harvey parked just a few spots down from where I was, so we continued in the same direction until I reached my car, at which point, I hugged Harvey goodbye. I lingered in his arms a little longer than any respectable woman should have. If he made a move, I had already decided that I’d have sex with him.

Then he spoke up.

“Taylor?” He said.

I looked up at him, and connected with those big brown chocolate eyes.

“Would you like to come back to my place?”

I smiled. “Yeah,” I said. “Yeah, I’d like that. I’ll follow you.”

As Harvey got into his car, I was soaking wet in seconds. I hopped in my car and followed Harvey just ten minutes or so until we pulled into the driveway of a cute blue house in your typical suburb neighborhood.

We entered the house into the living room, taking off our shoes and coats. With those off, Harvey stepped toward me, barely an inch from my lips. I pounced. Full on make-out mode, as I practically started dry jumping him, while we kissed.

In that moment, I had never wanted a man inside me more in my entire life.

“Where is your bedroom?” I gasped, breaking our kiss.

His hands still cupping my ass, he said through heaved breaths, “Right upstairs.”

We went back to making out, only now we were doing it while stumbling up his stairs while I unbuttoned his shirt. With it fully undone I caught my first glimpse of his abs and chest—pure masterpiece. I froze, I think in a combination of desire and nerves. He was no college boy. He was a man. He took the shirt the rest of the way off and tossed it to the floor, took my hand and led me into his dark bedroom.

Harvey turned on a lamp by his bedside, illuminating his room, then beckoned me to his king-sized bed and sat, smiling nervously. He took me in his arms and I melted again.

“Not very fair that I’m the only one missing a shirt, is it?” Harvey said seductively.

I kiss him again, and felt his strong hands squeezing my breasts, which made me even wetter. I may have been a virgin up to that point, but it wasn’t the first time I’d let a guy touch them.

“Mmmm,” I moaned in pleasure to his fondling.

I finally pulled my top off, getting it up over my head and then tossing it to Harvey’s floor. I may have let a guy touch my tits through my clothes before, but this would be the first time a man had actually seen them. Well, besides my surgeon, I guess.

Harvey watched in trance as I reached around my back and unlatched my bra, then discarded it with my shirt. My tits bounced a little in the soft glow of the lamp light.

“Wow. Absolutely gorgeous.”

I blushed at Harvey’s compliment. “Thank you,” I responded.

“May I lick them?” He asked.

“S-sure.”

Without further fanfare, Harvey leaned forward and began sucking on my right nipple as he fondled the other with his fingers. It felt amazing. After my surgery, I lost complete sensation in my nipples. I’m glad now that it didn’t stay that way because Harvey’s tongue was so so good.

“Ooohhh, wow!” I exclaimed under the barrage of Harvey’s tongue, and repeated.

I watched as Harvey released my tits and began to kiss down my stomach until he got to my jeans, which he quickly undid and pulled off my legs (thank GOD I shaved them) leaving me in only my pink panties.

I squirmed as Harvey’s fingers reached inside my panties and immediately began to explore my slit until he found my slick opening and pushed inside, another first for me. He fingered me briefly before withdrawing once more, hooking his thumps along the sides of my underwear and pulling down.

Being totally naked in front of a guy for the first time is completely nerve wracking. But I put on my brave face and Harvey seemed to appreciate the view.

“Take off your pants,” I insisted.

“Why don’t you do it, sexy.” He retorted.

He stood up and I sat directly in front of his crotch now and trembling reached out to unbutton his pants. I was better than I thought and quickly had them around his ankles.

He stood in his boxer briefs now and his bulge was even larger than before. I pulled those down and came face to face with my very first cock. It was pretty. I know that sounds silly, but like, objectively speaking, his cock was pretty. It was long, straight, and so thick. I couldn’t help but reach out and slowly stroke the entire length of it, entranced.

“Oooohhh,” Harvey moaned loudly at my touch, as I beat him off.

He was pulsing in my hand and it just looked so tasty. I knew just what do to—all the porn and Cosmo articles had prepared me for this moment. I settled my hand on the base, leaned forward and took him in my mouth.

“Fuuuccckkk!” Harvey cursed, complimenting me as I did my best to suck his cock, careful to not let my teeth touch his member.

I pulled back for just a moment to ask, “Am I doing good? It’s my first time with the real thing.” B.O.B made for decent practice, but I could never tell if I was doing it right, since my vibrator couldn’t really tell me otherwise.

“Fuck yes! Keep going!” He responded.

I then resumed blowing this DILF as he stood in front of me. His hands found their way onto my body, one clutching the back of my head while the other reached and found my breasts while I salivated all over his pretty dick.

I could tell that Harvey was holding back, I’m sure he was used to more experienced women, but he was patient. And I was enjoying it.

Sucking my first cock had gotten me extremely aroused, and I don’t think that my novice skills were going to be enough to make him shoot his load anyway. Plus my jaw was getting super tired, so his next comment was almost a relief.

“I want to fuck you so bad.” Harvey said through gritted teeth.

I nodded my head with his dick still in my mouth then pulled off. I had never been this turned on before and I was beyond ready to give up my V-card.

Harvey gently pushed me onto my back on his bed and positioned himself between my legs, then lifted them on either side of his shoulders. As he edged the big bulbous head of his dilf cock inside of me I squirmed. It was uncomfortable, but not unwelcome. B.O.B. made sure of that, but B.O.B. was neither as long nor as thick as Harvey.

I watched as inch after inch of Harvey’s dick disappeared inside me as his body joined mine, like a puzzle piece. He pushed forward until he couldn’t push any further and I felt his testicles rest against my ass.

I did it! Goodbye, virginity; hello, Harvey’s dick. Fully inside of me, he leaned forward, over me, folding my legs closer to my head, and pushed himself as deep as possible into my wet kitty. We both moaned in unison and then kissed. His skin felt good on mine. His chest on top of my tits.

I adjusted my legs and wrapped them around Harvey’s ass. My pussy had grown accustomed to his presence, and it felt amazing.

Harvey rested his head on my shoulder and my face was burrowed in his neck. His scent, his cologne, was intoxicating, and his slow hard thrusts inside of me were bringing me closer to my first sex induced orgasm.

“Oh my God!” I moaned, sinking my fingernails into Harvey’s back.

We made out and fucked, and clung to each other and enjoyed the feeling of his dick in my pussy. Harvey thrust into me faster and faster.

“Oh my GOD!” I cried.

“You like it?”

“I like it! Oh God, yesss! Fuck me! Fuck me!”

I held onto the beautiful man above me as he repeatedly pushed his cock inside me and I continued taking the Lord’s name in vain.

“Faster! Fuck me faster!” I begged.

He did just as I asked, pumping harder and more quickly, only now I began to fuck him back, lifting my hips to meet his.

Our moans got louder as the slapping of his balls against my skin increased.

“You’re so tight!” He groaned.

I’ve heard a lot of horror stories of people’s firsts. And I was honestly anxious. But this was everything I had hoped for. Nothing too serious. A man who knew what he was doing, and some really, really hot sex.

We were both covered in sweat, but it didn’t matter.

“Harvey, please! Don’t stop!”

He was absolutely drilling me into his mattress now, and I was on the precipice of my climax and Harvey could tell.

“Do it!” He ordered. And that’s literally all I needed—permission.

My legs quivered then straightened as my climax washed over me.

“I’m cumming!” I announced.

I was in heaven. I couldn’t move, couldn’t think, couldn’t breathe! And Harvey was fucking me through it. He had so much stamina!

It got pretty loud in that bedroom—his skin slapping against mine, him groaning against me and muttering my name.

“I’m going to cum!” He announced, swiftly pulling out of me, leaving me empty. I froze, I didn’t know what to do. So I lay there like a fish gasping for air as he hovered over me, dick in hand, and began shooting thick white ropes of warm cum onto my tits. There was so much of it, and my boobs were absolutely covered in spunk when he finished.

Harvey collapsed next to me on the bed, and I fell asleep with a smile as his cum dribbled down my breasts.

Source: reddit.com/r/gonewildstories/comments/wyk4zd/fm_i_lost_my_virginity_to_a_dilf