There’s Nothing Like a Toy in Your Ass to Make Playtime Even More Fun

I had no idea how sensitive my asshole was until one night when I was making love to my new girlfriend, Jennifer. We hadn’t been doing anything that kinky—I was on top of her, between her thighs, thrusting my cock in and out of her slippery cunt. Then, without warning, she snaked a finger between my cheeks and jammed it into my tiny back hole.

Totally overwhelmed by the most intense feelings of pleasure I’d ever experienced, I reared up and cried out. Then I sank my dick back into her pussy right before my balls exploded. My shaft pulsed wildly as my boiling cream shot into her body, and her muscles contracted around me as she came as well.

Afterward, I told her how incredible that had felt, and she replied that it had only been a test. Then she introduced me to her hidden cache of playthings, which included butt plugs and dildos, and even a strap-on cock that made my asshole throb with anticipation. “We’ll take this slowly,” she said, seeing me stare wide-eyed at the lifelike plastic dick.

We began our explorations the very next night. Taking out her box of toys, Jennifer pulled out an item she thought I could handle. It was a slender, three-inch butt plug with a flat, round base at the end, and my cock hardened instantly as I imagined how it would feel in my ass.

We both stripped off our clothes and climbed into bed. As I lay on my stomach, my erection pounding beneath me, I waited for my girlfriend to introduce me to pleasures greater than I’d ever known before. This plug was pretty large, and I knew that it would stimulate nerve endings that I couldn’t have even discovered without her help. First, she lubed up her fingers, and then she wiggled them into my ass to prepare me for the toy. I moaned loudly as she thrust in and out and then sighed with disappointment when she pulled away. That feeling was short-lived, however, because after coating the rubber plug with lube, she pried apart my ass cheeks with gentle fingers before she started working it inside.

I shut my eyes as the toy slowly filled my rear hole and wondered how I’d ever lived without it. I bucked my ass up toward Jennifer to let her know how good it felt, begging for more. But that was all there was, and sensing that I was ready for a bigger plug, she pulled this one from my ass and quickly replaced it with one that was larger. Longer and fatter, this new plug filled me more completely. My sphincter closed around the narrow bottom, the flat base now the only thing keeping my ass from sucking the entire thing deep inside.

“How does that feel?” Jennifer murmured, and all I could do was groan in response because I was so overcome by the incredible sensations emanating from below my waist. She rubbed circles over the plug’s base with her fingers so that the pointed tip massaged me from inside, and soon the sheet beneath me was soaked with the precome that dripped copiously from the tip of my dick. Unable to control the movements of my body, I ground my hips hard against the mattress, my arousal mounting by the second.

I turned around so that I was lying flat on my back, and the weight of my body pressed the toy deeper into my ass. Then there was even more pressure as Jennifer climbed on top of me and lowered her pussy over my dick. I raised my hips up off the bed to drive myself deeper into her cunt, but I missed the pressure of the plug so I dropped them down again. I kept my cheeks pressed against the mattress as my girlfriend began grinding her cunt down on my cock in an effort to drive herself to orgasm. That also served to increase the sensations that were sparked by the plug stretching my butt.

I reached up and kneaded her breasts as we shared some incredibly earth-shattering sex. The thick toy in my ass felt so sexy, and I wanted to find some way to thank Jennifer for introducing me to such delights. That’s when I remembered the tiny fingertip vibrator in the box of toys on the nightstand next to the bed. So I let go of her tits, reached over, and fished the vibe out of the box. I slipped it on and flicked the switch, feeling it come to life. She was too busy writhing on top of me to notice, so when I pressed the buzzing toy to her clit, she jumped and her eyes flew open.

A huge smile spread across Jennifer’s face upon seeing—and feeling—what I was doing. Her body began jerking, and as her movements grew more erratic, she pressed down, nudging the plug inside my ass. Soon I was jerking, too, my cock pounding into her cunt as her ass cheeks bounced against my balls. Keeping my vibrating finger pressed against her button grew difficult, but I persevered in order to give her the utmost pleasure, and from the noises she was making, I think I did a good job.

Our screams and moans grew louder as we fucked into oblivion. It wasn’t long before we reached orgasm, both of us coming extremely hard, thanks to the toys. That little vibrator packed a whole lot of power, more than I would have imagined, and I considered all the possibilities as we cried out our release. In my orgasmic haze, I thought about the strap-on dildo that I had yet to try. It was even thicker and fatter than the plug that had just then made me come so hard, and as my sated girlfriend slumped over my body, now wet and sticky with my cream, I decided that I wanted to try it soon.

I didn’t end up waiting very long. The next night, Jennifer showed up at my door clutching a large bag. She wrapped her arms around my neck as soon as I let her inside, and then my pants were around my ankles and she was on her knees sucking my cock. Her hands went right to my ass, though at first all I felt was surprise because I’d been expecting her slender finger, and what I got was intense vibrations against my tight little crimp.

My hips lurched, sending my stiff dick even deeper down her throat, and she sucked hard for a moment before pulling away both her mouth and the buzzing toy. “That’s for last night,” she said, her voice husky with lust and her tone light. I smiled as I pulled her up and then quickly undressed her as she pulled other stuff from her bag. “But I know this is what you’ve been waiting for,” she continued, pulling out the very same strap-on I had been longing to try out.

We didn’t even leave the foyer. Jennifer strapped the lifelike phallus around her waist, and it was strange at first to see a dick jutting out from beneath my girlfriend’s stomach, but I got used to it as I considered how good it would feel. Then she pulled a tube of lube from her bag and coated the shaft and head of the toy with a liberal amount, but I had to wait as she slipped her hand beneath her belt and stroked her clit for a moment. Her eyes closed and she bit on her lower lip, and though I was impatient for her to fuck me, I have to admit that seeing my girlfriend pleasure herself was very arousing.

Finally, she got down to business, telling me to turn around and bend over the small table where I throw my keys and mail. After I’d pushed everything to the floor, she got behind me and spread my ass cheeks wide. When I felt her fingers at my hole applying a generous amount of lube, I knew that everything I’d done before was just practice. This, however, was the real thing.

Then the bulbous head of her cock was prodding against my anus and soon sliding inside me, slowly and insistently, inch by inch. My muscles opened to accept the rubber intruder, which was soon completely buried. I hadn’t realized I’d been holding my breath until it came out in one huge blast, and then I sucked in more air when Jennifer pulled the dildo back out. My asshole closed around it in an attempt to stay its exit, but it couldn’t hold on because of the slippery lube. And thank God for that, I thought to myself as my girlfriend began fucking my ass.

She bucked her hips wildly, pumping the hefty toy in and out of my butt. My cock repeatedly bumped the table in front of me, and my balls boiled as my ass pulsed around the toy, and then my entire body began to shake when Jennifer reached down to massage my heavy sac. I thought about stroking her clit so that she’d feel as good as I did, but I couldn’t because the ass-fucking had rendered me immobile save for the clutching of my ass.

Turns out it didn’t matter; Jennifer had taken her pleasure into her own hands, so to speak. As she drove her fake dick in and out of my butt, she kept her finger beneath her belt, rubbing it over her tiny button until she was close to coming herself. With everything that was going on, it did not take long; in a second, her body was undulating wildly, which caused the dildo inside my ass to move every which way but loose. I thrust back against her hips, locking the toy up against her cunt as I exploded, sending a huge load of semen onto the parquet floor between my feet.

When we were done, Jennifer held on to my hips and slowly pulled out of me. I sighed at the empty feeling as a little more come dripped from the tip of my dick. Then I turned around, took her in my arms, and held her close, the hot, slippery dildo pressing against my thigh.

She wore the strap-on the rest of that night and on many occasions afterward. However, all good things must come to an end, and Jennifer eventually relocated because of her job. However, she left me some of our favorite toys, so whenever I get the urge—which is often—I just pull out a plug, vibrator, or dildo, insert it in my ass, stroke my cock to orgasm, and think of all the fun we had.

—Mr. Peter J., Tallahassee, Florida