Age Gap Fling Opens My Eyes

I was never into casual sex before the pandemic. I think because I was afraid of it. I had always viewed sex through the lens of "this is for relationships only." But there was something about being locked up and alone for a year during Covid, that we all began to crave human interaction again, especially touch.

Katie was the one who changed my mind about casual sex. We matched on a dating app and each came out of the gate heavily flirting, dipping into inappropriate territory. After she asked for my number, the sexting and nudes began.

She was almost a decade my junior and in college. As we men know, the thrill of a vibrant younger woman wanting us is rather quite alluring. Having mostly dated women my age or slightly older, I was enthralled by this age gap. Katie was an adult, and could make her own decisions about who she wanted to fuck.

That person just so happened to be me.

Our first date was a walk around the park. We chatted and laughed for over an hour before I invited her back to my place. I made her coffee, but before the pot was full, her lips crashed against mine.

Greedy for physical connection, Katie pressed me against the counter, her heavy D-cup breasts mushing between us. We smiled between kisses at the sheer passion - the need - that each of us felt.

My heart hadn't raced like that in so long. She encouraged me to touch her, so my hands slid down her curves to cup her ass, pulling her against me. Katie moaned in my mouth feeling my erection press against her hips.

"Fuck, I want you so bad right now, but my test results aren't back," she moaned into my ear.

"The minute you're in the clear, you're driving over here so I can have you."

She smiled and kissed me again. Neither of us wanted to stop, but we wanted to be careful. I had never had sex outside of an exclusive relationship, so this was new territory for me.

My last relationship was several years ago. We stopped using condoms and relied entirely on the pullout method. My willpower was strong, surprisingly enough. However, I hadn't used condoms for sex in half a decade, so I couldn't remember which brands I enjoyed.

On my next grocery store trip, I bought three brands of condoms. Overkill, yes, but not being used to the sensation, I wanted to ensure I had options when the time came.

That night, I got a call around 11:00 PM from Katie. She was whispering something, and I couldn't quite hear what she was saying. After a moment, I realized she was muttering with her vibrator pressed against her clit.

"Sounds like someone's being naughty tonight. Wishing I were there to help you?"

"Yes," she whispered. She lived with her conservative parents, so I knew she was being quiet for them.

"I bet you wish you could replace your fingers with my tongue right about now."

She let out a soft moan. The wet noises on the other end of the line began to speed up.

"I can't wait until I make you cum in my mouth. It's going to feel incredible to have you shaking against my face with your legs wrapped around my shoulders."

Katie's breathing grew heavier. "Nobody ever done that for me."

I paused for a moment. "Wait, what? A guy's never gone down on you before?"

"Nuh-uh," she responding, still fingering herself with the vibe against her clit. "I want it so bad."

"What else do you want, Katie?"

The covers ruffled as her legs began to slide around, wanting to feel someone between them.

"I want to feel you inside of me..." Her voice was nearly inaudible. Due to the position of her phone, I could mostly hear the sheets ruffling and her vibrator. "I need to cum."

"Then cum for me, baby. Soon, you'll be cumming in my mouth. I'm not going to stop until you give it all to me, and then, only then, I'm going to fuck you."

Katie slapped a hand over her mouth as a moan almost escaped her. She began to cum hard. I heard the vibrator switch off and imagined her hips thrusting up to meet her fingers.

She abruptly ended the call but followed it up with a picture of her dripping wet pussy. "Sorry, my mom walked by room. Looking forward to letting you taste me."

It was a long week waiting for her test results to come back. Every day, we were sexting. I was the proud recipient of several nudes, just waiting for the day I could have her breasts in my mouth.

During those few days, Katie asked about my kinks. There was only really one thing I wanted to explore.

Me: "I've never had bareback sex and had a partner encourage me to cum inside of them. It's always been off-limits, even with my exes on B. C. I've been really craving to see what that feels like."

Katie: "Oh, well that's only something I'd do in an exclusive relationship. I am on birth control, but I want you to use condoms."

Me: "Yeah, I figured. I bought plenty. But you asked, so now you know."

Katie's big fantasy was having a man eat her out. She also really enjoyed hair-pulling and spanking, all of which I said I'd gladly indulge. And the conversation ended there.

To this day, I don't understand why more men don't enjoy foreplay and literate sexting. Women always complain men just send dick pics and ask for nudes, and they're trash at dirty talk. Perhaps being a writer gave me an edge because Katie loves our dirty texts.

Either way, her denial of my creampie kink wasn't entirely unexpected. I had hoped us both being tested and clean, our dirty talk, and her being on birth control might get me a pass.

Regardless, we were both excited to have sex for the first time in over a year (several for me at the time).

Katie showed up within a few hours. She practically leapt into my arms when I opened the door for her. She was on me before the door shut behind her.

I pressed Katie up against the door, closing it with a soft thunk. Her hands went immediately to my belt. To my surprise, she pulled down my jeans right then and there and stuck my cock in her mouth. Bracing myself against the door with one arm, I touched her face and hair as she pleased me.

The realization of what was happening hit me in that moment. I was hooking up with an eager college girl, and it felt amazing.

"I need to have you naked in my bed right now," I said. I grabbed her ponytail and guided her up to me. Her wet lips pressed against mine, then she pulled away, breathing hard.

"Are you gonna..."

"Yes, I'm going to eat your pussy, and I'm not stopping until you cum. Hard."

Katie leaned forward and kissed me. She reached down to grab my cock, and pulled me to my room.

--

This was a huge deal for me. I've dated women for years who were on birth control but always made me wear condoms. I even had a girlfriend who at one point made me double sleeve. Yeah, it's crazy looking back on it, but I've learned from it and can now laugh about it.

Over time, going in raw became a little fantasy of mine. Nothing crazy. I just wanted to feel what it was like to cum inside my girlfriend. Alas, it was not to be.

However, a few years back, I (30m) met a college girl ten years younger than me on a dating app. We'll call her Katie. She was very forward and dirty, so we started sexting regularly. Then she started sending nudes. Then it was naughty calls while she was getting off.

Finally, she sneaks out of her (super controlling) parents' house and comes over mid-afternoon. The first time we tried to have sex was really awkward. My new (untested) brand of condoms choked off all feeling and circulation, so I struggled to maintain my erection.

To hide it, I took my time to eat her out. It was her first time receiving oral, so the heightened anticipation made her cum quickly. She moaned so loud I thought the neighbors were going to call the police.

She asked me to fuck her, and I couldn't. Not with these condoms. I got nervous, which escalated to a full-blown mental breakdown wondering if I had ED. However, she was amazingly supportive and said we'll try again once I got new condoms.

Two days goes by and we can't stop sexting. We're both even more horny. This time, we talked about our fantasies, and I mentioned bareback and cumming inside (creampies, and not the oatmeal ones). She had an IUD and we were both tested. She said those were for 'boyfriends only,' but she was surprised I'd never had sex without a condom. Basically, she said, "Good for you. A shame."

The next night that she comes over, I have different condoms. She was so tight that I thought she was a virgin. However, these rubbers were too thick and I really only felt pressure. She wanted me to go hard, so I gave her a good pounding. However, the sex felt like nothing for me.

She came with my fingers tangled in her hair pushing her face into the bed. Her ass was stuck up high as I thrust in feverishly from behind.

[I'm now aware that there are thicker condoms to make guys last longer. I don't need those.]

I made her cum once through oral and again through penetration (a lucky girl, so I hear). After she climaxed twice, she climbed on top. She was kissing me slowly and riding me cowgirl as she rode the tidal wave of her orgasmic high.

"You think you're going to cum soon?" she asks.

"Honestly... probably not. These things are so thick I can't feel a goddamned thing except for how tight you are." It felt like I was just getting squeezed, but not in a good way.

And it was in that moment, she seemed to make up her mind about me. Maybe it was the way we talked and flirted and kissed before we ever got naked. Maybe it was because we'd lay in bed for hours talking afterward to learn about one another's lives. Maybe she was just horny.

Katie looked me in the eye as she reaches back to touch my balls. She started fondling them gently to see if that helped. We continued our slow motions for another minute, and then she reached up to hold onto my shaft. At first, I thought she was trying to stroke me.

But instead she slipped my condom off. Intentionally.

She placed the condom on the bed beside me as if it were an offering of love or a big tease. Without even using her fingers, she ground her soaking wet pussy against me until I slipped inside of her pussy - raw.

My breath caught in my throat. Katie sighed in my ear like she just found the missing puzzle piece, and it fit perfectly. Slowly, she continued to ride me. Her DDs were pressed firmly against my hairy chest. Her body was so soft and warm compared to mine. I've had never felt anything like it.

And in that moment, I wanted nothing more than to fill her right then and there. I wanted to be a part of her, and her of me. Part of me saw me claiming her, while another part saw it an equal union of spirits. The horny part of me, of course, wanted to feel it with her.

She whispered quietly, "Are you going to cum now?"

"Yeah," I barely manage to grasp. "I'm close. Please don't stop what you're doing. It feels so good...."

Then, this lovely girl kissed my neck as she pushed me as deep as I can go. She leaned whispered in my ear, "You can cum inside of me if you want.

"What? Really?" I was taken aback, but I wanted it, too.

"I want you to cum inside of me. It's okay. Cum. Please, cum in me..."

Those became the magic words. To date, I have never cum so hard in my life. I whited out, and it took a few minutes to fully regain my vision. Stars exploded as I shot rope after rope of cum deep inside of her - three, four, five times. I had never cum so much in my life. Where is all of this coming from?

It was the greatest and most sexually satisfying orgasm of my life.

Katie had apparently been smiling as she watched my facial during climax. She leaned gave me a quick peck on the lips, and little chuckle escaped her lips.

Katie: "That good, huh?"

Me: "You have no idea." I felt entirely out of breath.

Katie "No," she said while walking fingers up my chest. "I think I do."

She kissed me again, and thus began the wild summer fling with a college girl ten years younger than me. I didn't have to wear condoms with her ever again, and a whole new world of pleasure opened up to me.