Finding My Boyfriend's Dildo

The best thing that ever happened to my sex life was finding my boyfriend's dildo in his sock drawer.

I was 22 at the time and while I had enjoyed the two years I'd spent with Gavin, the sex had started to feel a bit pedestrian, especially considering my high sex drive and overactive imagination.

I was a girl quickly developing into a very good sense of my own blossoming horny self--a pastor's daughter turned liberal college feminist, though I think a lot of that was still somewhat hidden below overalls and snug sweaters and "ah, shucks" girl next door vibes. it was something that lived in my increasingly racy thongs and porn searches and bath-time masturbation sessions.

Gav probably knew what an unleashed hottie he had brewing in me, but I think maybe he was also a little afraid of my late bloom into kink and sexual freedom. I was still the innocently curious Taylor Fitch.

He had met my straight-laced parents which included my Calvary Chapel Pastor Dad and my AYSO weekend halftime snack queen Mom, and he knew I was still slightly living with both feet in two different pools of water. He was careful with me, as much as he adored me, and I was apparently still peeling my interesting onion of a boyfriend.

I had recently cut my hair into a risky, blonde bob that screamed Michelle Williams chic, and I held up the plastic, six inch cock, which was sculpted and shaped just like an actual penis, veins and all.

I stared into the mirror above his dresser and giggled at the toy in front of my perplexed face, framed by my brand new haircut. My hair style was daring. My mother would gasp if she saw my new cut. My father would gasp if he knew I was dating a guy who liked ass-play. And that had to be my assumption, right?

This was not a toy he'd ever used on me. Our shoebox under the bed had a couple of toys we had occasional fun with, and this was not in that well-known rotation.

I had never seen this fake, flesh-covered dick before.

I was flabbergasted.

Did he?

I wondered suddenly.

I don't know why I did it but I brought the cock up to my nose and sniffed it.

The faintest smell of ass. I smiled.

There was the tiniest whiff of shit, cleaned heavily with the Bath and Body Works soap in our shared apartment bathroom. 'Apple Butter Blossom' with just a hint of 'Boyfriend Butt.'

"Caught brown-handed," I thought. I laughed out loud in the empty apartment.

Gavin wouldn't be home from his classes for another few hours and my mind was suddenly racing.

Either my very masculine, straight-presenting boyfriend was sneaking over another girl while I was out of the apartment and fucking her ass with a hidden toy...

...or...

...he was fucking himself. And had never told me.

I was ninety percent certain I knew which was one was true.

The instant thrill that jolted through my body when I thought of my boyfriend doing that to himself was unexpectedly wonderful and I was horny from it immediately. I could feel the warmth between my legs.

I looked at my phone to see if he had texted me. I knew I had my run of the place for the next hour at least.

I glanced over at his desk where his open laptop sat hibernating.

I knew I shouldn't. I knew this was morally crossing a line.

But I needed to know. My brain and my pussy NEEDED to know. He's the one that was hiding a dildo after all.

I pulled up his internet search history as I leaned up, barely perching my ass at the top of his desk chair. I was on a mission now. I had to know for sure. I was also strangely excited by it all.

But there was nothing.

No Pornhub.

No Literotica.

No saved Tumblr pages with fantasy-driven images.

Even I had those.

I sighed a frustrated sigh. My pussy was not finding the evidence I was hoping for. How did he not watch any porn? That wasn't possible. I'd caught him at least once when coming home. We'd talked about it, but never watched any together. So...why would he delete it? Unless he was embarrassed at the categories he was choosing. But it didn't make sense. I found plenty of search history for everything else he looked at.

But then as I was about to give up, I realized that his laptop had both Chrome and, almost hidden as a logo in the very right corner of his screen, the Safari icon. Like it had been dragged almost out of sight unless you knew it was there, hiding just to the bottom right of the recycling bin.

I raised an eyebrow. Why did he need to store the shortcut in a barely visible spot like that? Unless...

I clicked it open and scrolled up to the history, and this time my kinky boyfriend was outed immediately.

WOW.

He had both Pornhub and Xhamster page searches that seemed to scroll on forever. Video history as recent as yesterday included bi mmf porn and cuckolding porn and pegging porn. He watched tons of videos of cock hypnosis and a category called 'babecock,' which was basically just compilations of sexy girls shown side-by-side with all sorts of hot cock action as a soothing female narrator described the nasty gay things she wanted the watcher to engage in. That was fucking hot to me. I even found Literotica history from the 'First Time Gay' category and even some 'Gay Daddy' content. Gay seduction was a popular topic for him too I realized. So was pegging. So was bisexual. He was a very busy boy. I laughed and got a warm buzz knowing all of these things turned my guy on. So many secrets were buried in these searches. I was immediately his Freudian observer. Gavin was obsessed with the idea of cock.

I also noticed a very heavy focus on anal penetration. Lots of bareback cock in lots of submissive asses. He didn't seem to watch a ton of blowjob videos even though there were definitely some guys that were made to suck cock and even strap-on cock. Mostly he was obsessed with watching men made to submit. Strong men, bent over and taken. Slutty men, spreading their asses for new cock.

I was growing slowly more aroused imagining my overtly straight boyfriend getting off to all of this gay porn. How could he never tell me any of this? That was my first thought, but then almost immediately I understood and I knew the myriad of reasons.

I was still the pastor's girl from back home. I was still very straight-laced in how I came off. Maybe he thought I'd freak out and break off our relationship? Maybe he was scared I wouldn't accept his vibrant curiosities?

This wouldn't be the same as him finding lesbian Literotica pages on my phone (of which there were plenty). Society truly was fucked up like that.

But I didn't give a damn. I was just horny. This was undeniably hot. The more I thought about it the more I realized just how crazy sexy I found it. My boyfriend. Dreaming of cock in his straight ass. Thinking of how it would feel to be filled by a man.

My Gavin, who I had a medium quality sex life with, was hiding some very naughty interests from me and I wanted to know so much more.

And that's when my scheme began to form.

As with all gracefully executed plans, timing would be everything.

In the thirty minutes remaining before he got home, I closed up his laptop and left everything exactly as I had found it. He couldn't know what I knew. Not yet.

I went out to the living room couch and grabbed my own MacBook and began to put the dirty wheels in motion.

First, I purchased a highly-rated strap-on cock from a sex toy website I frequented. It was a silky, powder blue harness with a six-inch dildo that had more girth than Gavin's. I bought four, soft sex restraints, and even purchased him a jock strap that looked a lot like the ones some of the boys in the videos he watched wore. A girl could dream after all.

And then, the rest of my week was spent doing my dutiful research. Whenever he was away at class and I was home, I'd dive back into his internet search history and devour all of what he had been watching. I loved his naughty kinks.

There were numerous things I had to pull off now, but my sudden horniness at the plan I had hatched carried me onward with a zestfully dedicated intention.

I snuck a couple pictures of Gavin's ass one night after the covers had slipped off his naked buns (we'd had sex earlier and then drifted asleep). His ass looked good in the low light and I had never noticed how truly juicy a butt he had. It was like mine. I bit my lip as I stared.

I fantasized about watching another guy fuck him. Fuck that was becoming so hot to me. I was very into Gavin's secret kink. I just hoped he was really into it too.

Sometimes curiosity isn't serious. It's just curiosity. I had to be careful.

He had a much busier class schedule that week when it came to projects due and I was luckily in a very easy stretch where I was able to be at home much more to plot.

I continued to scroll back in his video and erotica searches and I'd started to treat him as a case study in sexual exploration. I crawled into my boyfriend's mind like an FBI profiler. I had to get everything perfect...I knew this much.

He watched so much MMF porn where the girls seemed very in charge of orchestrating the boys activities together. I noted that. He needs a bandleader.

"Is that what you want, Gav? You want me to make you take a sexy cock?" I said maniacally one afternoon, while enjoying a seltzer on our second floor apartment patio. I had his laptop in my lap and I was balls deep into my reading. I was theatrically becoming his bottom-scheming Bond villain: 'Boypussy Galore.'

In my digging I found lots of stories about the idea of breeding, and men taking ownership of other men simply with their sexual power. He was clearly very into the idea of having a man cum inside his ass. That much was obvious.

I quickly started to get the idea that what Gavin needed was a level of direction and seduction and acceptance. He was never going to seek out dick on his own. His favorite porn and sex stories all centered around a strong female or male antagonist forcing a man to submit to his nastiest gay desires.

I loved that. I could do that for my Gavin. I could make him love cock. I could orchestrate his anal demise.

I was damp again in my booty shorts just thinking about my devious plans for that Saturday night, only two nights away.

Gavin and I had a free evening together without any huge tests or projects to worry about and we were finally gonna get to go out and enjoy each other's company.

I took out my phone and checked which DJ or band would be playing at our favorite local bar.

Then I opened up the Grindr app that I'd downloaded a couple of days prior. I'd downloaded a picture of Gavin's naked ass, but from the side so that it technically wasn't nudity, and the profile bio had been a simple one. I'd been very direct.

"I just discovered my straight boyfriend is hiding some serious gay anal sex fantasies and I'd like to surprise him with his first cock on Saturday night."

I got hundreds of responses in days. So many guys were delighted at the kink of the setup.

The ones who looked like the types of normal, non-psychopath, recently-tested dudes that fit the vibe of the men in Gavin's videos, I quickly began private message convos with.

I whittled away the candidates who hadn't been tested recently, and I asked for cock pics of course. I was shopping for a cock worthy of a first-time fuck. I loved my boyfriend and I wanted to make what he probably thought was a ridiculous pipe dream into an actual pipe reality.

I laughed at the ridiculousness of this, but like, how fucking amazing would it have been if a person who had loved me this much had been able to hand-select the perfect cock for ME when I lost my virginity?! Rather than that stocky chub that had railed me in an In-N-Out parking lot for three un-glorious minutes after a losing baseball game, only to immediately ask me if I had cum.

Yes. Buckets. So good. Woot.

This could be real for him. I could snag him a really hot cock. And I was being sent some prize stallions to select from.

God bless the simplicity of the male sex drive and Grindr.

I settled on a guy in his early 30's who was mixed race. He had the chiseled jawline of Henry Golding and his whole body was built like a 24 Hour Fitness trainer. Later of course, I would find out that he was a trainer...

...at 24 Hour Fitness.

Whatever. All that mattered was that he was masculine, easy-going, and his cock was a fat, seven-inch pole that looked like a champion fraternity dong. I'd fucked a couple of guys like this after escaping my Christian home life, and I always came home walking a little sideways and smelling like an Abercrombie dressing room. Gavin wasn't fully aware of some of my own early college proclivities like he'd thought. I just didn't feel like fully explaining my post-church-girl slut needs before we'd met.

And yet, here I was, fully ready to help him plow through his. I giggled again as I messaged back and forth with Oliver. That was his name. He said to call him 'Ollie' which worked for me.

He had lots of questions of course and I dutifully answered them all, though I might've left out the fact that Gavin had no idea about any of it.

The white lie I told him was that my boyfriend knew I was bringing over a cock to take his ass for the first time on Saturday night. I'd be tying him to the bed and helping him realize himself, even as I pushed past his fears and reservations.

Oliver loved all of this. He was very turned on by the idea of getting to take a curious guy's cherry for the first time. He said that was a big kink for him...turning straight guys.

I loved that. That was another storyline that Gavin was obsessed with on Literotica.

"Perfect," I told him. He was the exact candidate I was looking for.

"My cock is big...you should probably buy some poppers for him for his first time so it doesn't hurt too much," he said.

Poppers? I had asked. I didn't know what those were. I had no clue what he meant. Did Gavin need a crappy chain restaurant appetizer to enjoy big dick? I chuckled.

He quickly explained the amyl nitrates and their affect on anal sex for bottoms and I loved that. I had no idea there was any such thing that existed. He told me which sex shops I could buy them from and I thanked him and made a note to go and grab some that next day.

The plans were set for that Saturday night and I finished getting everything together and ready. I could hardly wait to put my plans in motion.

When I saw Gavin that Saturday afternoon I kissed him hard and we made out for a few minutes on the couch, playing with each other lightly.

"Hi babe! I'm excited for date night!" He yelped to me. I smiled. If he only knew.

"Oh honey, me too! This week has been so exhaustingly lame," I lamented.

We took a relaxing nap with the sliding door open for the breeze, and then had dinner at a local burger spot we liked. We went home and got ready and I got all dolled up for him in an outfit I knew would get him going. My flared navy skirt and cute button-up yellow blouse were the perfect vibe. I did my makeup and my nails and grabbed some proper heels. I wore the sexy black strap-on undies under my skirt. The ring that was built into the front felt dangerously exciting pressed against my pussy. If he only knew.

Behind the scenes I was messaging with Oliver to make sure he understood everything for later that night.

This was the craziest thing I had ever planned but if I pulled it all off Gavin would have the night of his fucking life.

We went out to the bar and flirted and played and danced. We did shots and shared a pitcher of beer and then we stopped into another one of our favorite dive's and by the time the night was getting later we were both appropriately tipsy. Gavin was a little more drunk after I had carefully ensured he have more of the beer than me.

As we played pool in a dark corner I came up behind him as he tried to focus on a particularly difficult shot. I ran my hand down his back and caressed his ass cheek.

I watched my boyfriend flutter his eyes as he flubbed the shot.

Gavin leaned up and grabbed me by my waist.

"Mmm, babe," he said, and we kissed.

I could feel his hard-on press against me and it stayed that way as we continued to tease and touch all through our foreplay heavy game.

I particularly teased him every time I arched my ass back towards him. A few times he ran his hand up under my skirt to fondle my booty, which he was obsessed with.

The night already felt more exciting than our more recent encounters had been. The energy was different.

"I'm gonna make you be my naughty boy tonight," I said to him confidently, as we kissed after a face-scrunching shot of whatever the well was. He had no idea.

"Oh yeah?" He smiled at me sheepishly. He was drunk and he was cute.

"Yeah," I countered, showing him I was serious. I was smiling, but in a more intentional way. I could feel the allure of my planned seduction starting to wash over me. I couldn't stop staring at his ass in his jeans. I couldn't stop thinking about taking him with my strap-on. My secretive boyfriend and his curious ass.

"You gonna be my bad girl tonight?" He asked, running his hand over my ribs through the thin blouse, and caressing the side of my breast in my lacy bra.

"Yeah, baby. I'm gonna be very bad...just you wait and see," I ran my hand over the outline of his hard-on and he teasingly traced my fingers off the protruding denim. He had to adjust himself as he laughed in tortured glee.

"Well...we should probably just go then, yeah?" He asked, completely forgetting the game as he half-joked. I know he would've.

"Naw...you need to buy us another shot and another beer and then you need to finish this game because I'm about to beat you two-out-of-three." It was true. We were tipsy, but we could also be drunker. And I was dying from the foreplay alone. It was only 11.

The next half hour was amazingly fun. We did our shots, drank down our final lagers, and danced to shitty juke box music. Honestly, bar people were obsessed with the same ten songs. I carefully maneuvered my balls into those greedy holes like an experienced pool shark. There is just something about knowing you're about to watch your boyfriend lose his anal cherry that revs the competitive feminine engines.

I sent him a kiss across the table as my eight ball clattered into the corner pocket I had called, and soon we were grabbing our things and heading for the door. We were turned on. We were in heat.

We strode out of the bar like two people who know they're about to do very naughty things. And the rest of the bar probably knew it too.

He had his arm around my shoulder and I had my hand in his back pocket. My cute boyfriend. I squeezed his ass as we exited out onto the street and felt the warm, summer night air kiss our skin marvelously.

We grabbed a Lyft and arrived back at our college apartment five minutes later.

Tequila sodas were made in the kitchen with sloppily sliced lime wedges, and we traded turns in the bathroom as I got some music playing.

When Gavin came back out he asked me if I wanted to go to the couch and I said yes. We kicked off our shoes and toppled over.

We made out on the sofa like two high school kids. Were were horny for each other.

I grabbed my weed pen from out of my pocket and had him take a big hit. Then me. Then him again.

We were stoned. We were drunk. We were horny.

He tried taking my blouse off and I let him. My laced black bra was on display. He got excited when he saw it. I raised my eyebrows at him.

"Mmmm, baby, what's this?" He asked excitedly.

"Well, remember, tonight is gonna be a very naughty night," I reminded him with a very sexy minx of a look on my face.

He stared to run his hands up under my skirt but I slapped them away.

"Follow me, baby," I told him, and I walked him down the hall.