My Anal Origin Story

It all started with her new vibrator. After a couple years of sporadic use in our not-so-incredible sex life, her faithful old one had finally died, and so off I went to the adult store to replace it. Browsing through the options, I finally settled on one. Nothing fancy, just a simple, metallic blue one, about 6 inches long and about the width of a big permanent marker. Returning home, I presented my acquisition. She took it out of the packaging and looked it over, evaluating my choice.

"It's a little thin, isn't it," she said. "Hell, I bet it could fit in you pretty easily!"

That caught me off guard. It wasn't the reaction I was expecting at all. We were not really a kinky couple, and although I knew she had gay friends from the theater world, it wasn't something we'd ever discussed. I laughed it off that night, but the next day, I was off work, and she worked the morning shift. So I had some free time, and I knew how to spend it.

I went up to the bedroom, stripped down, and laid back on the bed. Grabbing the lube that had been sitting unused in the nightstand, I coated the business end of the toy, and then used a bit more in and around my opening. This was a new sensation, and I was surprised how sensitive it was back there, and how eager I was to continue. I eased the vibe in, slowly, wincing at the first intrusion into my ass. However, when I got it a few inches in, it felt amazing! Stroking myself with one hand, I reached down and twisted the control on the vibe, starting a humming that pushed everything else out of my mind. The vibrations buzzed through me, and I came with a shudder. Afterwards, I lay panting and couldn't wait to share the news later.

That night, after dinner, we sat on the couch watching TV and enjoying cocktails. I took a big gulp of my whiskey and steeled myself for the big revelation.

"Hey, so today while you were at work, I tried something new, and it turns out you were right."

"You did? What did you try?"

"So.. I can take your new toy... you know, back there..." I said it shyly, kind of embarrassed now that it was said out loud.

She stared at me, eyes lighting up. "Really? I want to see, can you do it again?"

Back upstairs, did the whole setup again. Lube on the toy, and started to finger myself, but now with an audience. I could feel her eyes on me, so I closed mine and tried to recreate the moment from earlier. As it slid home again and started pulsing inside me, I began stroking, and felt her hand close over mine, speeding up as I worked the toy in and out. Soon, I felt my balls tightening and the splash of my hot cum onto my chest. I lay on my back, panting, and slowly becoming aware of her watching me still.

"Wow', she said, smirking. "So, you liked it? That looked pretty intense."

"It was, and I did. We should really consider doing this again."

As time went on, we did do it more often. It became a semi-regular thing to have her assist my masturbation with the toy, and sometimes she would initiate it, bringing it out during sex or offering it as foreplay. I didn't always take her up on it, but when we did, I came hard every time, and would enjoy the euphoria from it for a few days after. I think some of it was the thrill of knowing she was enjoying the show when we did it, and the return of thrills to our sex life. But a big part was also that having something in my ass felt so damned good. I continued playing with it on my own, too, and eventually began browsing for porn similar to what we were doing. I quickly discovered pegging, and it became a go-to for alone time. I felt a little embarrassed at how hard and turned on they got me, so I didn't mention it to her right away.

So it continued, the periodic anal play slaking my growing lust for these taboo turn-ons. Eventually, we hit another lull sexually, and after some discussion, decided to expand our horizons again. We decided to go check out the local adult store that weekend for some DVDs and in the meantime, since we had the afternoon free, we went to one of those boutique adult stores for couples to get started. We browsed a bit, checking out the toys and giggling at the oversized ines and the cock-shaped candies for bachelorette parties, then picked out some lingerie for her, a couple scented candles and massage oils and the like. Walking to the counter with our selections,she nudged me and pointed to a strapon dildo and harness kit on display near the register.

"What about that?", she asked, giving me a devious look. Before I could reply, or check it out, the young lady at the register began ringing us up, and we got distracted. On the drive home, she brought up the idea again.

"So... maybe a strapon? Would that be fun? You like my fingers and the vibrator in your ass, want to give it a try?"

I took a deep breath, and replied that it did sound fun, and I'd be up for getting one. We agreed that I would go pick one up after dinner, and also maybe a DVD of some strapon play, to give her ideas and insight. As she reminded me, it would be her first time being the one with the cock.

I went out later that night to a different store and after several anxious minutes of browsing and waiting for gawking college kids to leave, picked one out. It was purple, not realistic looking, and about the same size as my own, so not too intimidating. Pacing the video aisle and shuffling through the cases, I found one video that looked promising, no leather and latex dominatrices, just sexy women fucking their guys, like the videos I'd found online. I gave my stuff to the cashier, accepted his upsell of a bottle of lube, and made my way home, excited and nervous. I'd thought about this a lot, and wasn't sure how she'd feel about it when it went past the hypothtical.

On arrival, she unwrapped the new toy, looking it over and sorting out the details of the straps. Then, she looked over the DVD, laughing when she realized that one of the girls on the cover kind of looked like her. We put the toy upstairs in the nightstand, and went down to the living room for movie night. I grabbed a beer and poured her a glass of wine, and settled into our usual spots on the couch. My chest was pounding, fearing judgment or disappointment, but I did my best to not give it away. We pressed play and got into things. I was definitely enjoying it, and tried to divert attention from my interest with jokes about the décor in the background, or the obvious bad edits. She watched with a more critical eye, occasionally asking me about the action onscreen. We watched guys getting surprised with toys, being asked to suck it, and getting caught playing with butt plugs, followed by vigorous ass fucking and the obligatory cumshot. After two or three scenes, she turned and said she'd seen enough for the night. Did that mean we were heading upstairs?, I asked with a grin. No, it just meant she'd seen enough to get the idea and wanted to process and ponder a bit before anything happened. We switched the movie off, picked a more straightahead one from the cabinet (the heartwarming story of a simple girl from the Midwest trying to make it in the perverse world of adult film). We did end up fucking that night, but no ass play for anyone yet.

A few days later, I came home from work to find her in the living room, wearing a short sundress and a devilish grin, and not much else. She stood up to greet me, took my hand, and led me upstairs, lifting the back of her dress to flash me a naked ass on her way up. Apparently, I was getting laid this afternoon, and I hurried upstairs behind her. In the bedroom, she turned to face me and lifted the front of the dress to show me what else she was wearing: the harness, with the now slightly more intimidating purple dildo sticking out from just below her hips.

Are you ready, she asked, pushing me back on the bed and undressing me. Believe me, I was ready. I lifted my hips as she pulled my jeans down, and my own stiff cock bounced out, ready for things to get going. I lay back and spread my legs as she stroked and rubbed my cock, my thighs, and my ass, grazing a finger across my opening and pushing against it. She rubbed some lube onto my hole, working it in gently, and probing with her fingers. Then, kneeling next to me on the bed, she pulled the dress over her head, leaving the toy swinging in my face. I took some initiative and stuck it in my mouth, licking it hungrily, pulling it to the side to lick her pussy as well, and getting both nice and wet. Soon, she laid back on the pillows her cock standing up and beckoned to me, saying, Ride me, I want to watch you get fucked.             

I straddled her, reaching back to spread my ass open and take it. I slid down it slowly, lowering myself 'til my ass rested on her thighs and my balls were on her belly, and begin rocking forward and back, like she had done riding me before. My ass was filled up, and I was in ecstasy; eyes rolling back in my head. She closed a hand around my dick and began stroking. She cheered me on, telling me it was so hot to watch me riding her dick. Soon, I was bouncing up and down, moaning, and thrusting my hips against her hand, until I began spraying her chest with my cum. Overwhelmed, I collapsed forward into the puddle, smearing it between us in a sticky mess. As the endorphins subsided and reality reasserted itself, we began peeling ourselves apart and reaching for towels to clean up. She grinned at me and said, we're doing this again soon, right?