Dylan stripped me of my lingerie like a man unwrapping a gift. Though we'd been together almost six months, he still treated every intimate encounter as if it were our first time.

"What do we have here?" Dylan grinned while lowering the strap of my pink babydoll. As soon as my nipple was exposed, he leaned to give it a teasing lick. His tongue quickly coaxed the peak to hardness.

"You like that?" I murmured. Already, I was saturating my panties.

"So much!" To emphasize his words, he drew my nipple into his mouth and began suckling.

I wanted nothing more than to pull him back with me onto the bed, but I made myself wait. Sometimes I found it amusing that Dylan was consistently the patient one, taking his time in bed, when I was over ten years his senior. My friends thought it was hilarious that I was just shy of forty and dating a guy in his late twenties, yet they were impressed upon meeting him. He was mature and steadfast in a way my ex-husband had never been, and he good-naturedly endured their teasing. They oohed and aahed over his dark curls and large brown eyes, and also the dimple in his chin.

They would have carried on even more had they known about some of Dylan's past sexual escapades. I couldn't help but be a little insecure that he was so much more experienced in bed, but then again, I'd been married for the last fifteen years, with my divorce only recently finalized. My ex-husband hadn't liked to venture beyond blowjobs and missionary sex, so Dylan had plenty to teach me. I'd never come right out and asked him how many partners he'd had, and he didn't volunteer the information, but I guessed the number was vastly higher than my own, which I could count on one hand.

Dylan, however, was never cocky about his sexual prowess, and he never pushed me to try anything that made me uncomfortable. It was because he was so patient and tender, not to mention gorgeous, that I found myself wanting to be wilder with him.

Recently, he'd asked me what I might like for a fortieth birthday present. "I want to make sure I give you something you actually want," he'd said.

"A vibrating butt plug," I responded. Remembering his shocked expression still made me grin.

My birthday wasn't until next week, but I'd asked for my gift early so we could try it out. Now, we were on my bed, and my new toy was on the nightstand, along with a bottle of lube. Dylan had chosen a starter plug, so I didn't find the size intimidating in any way. In fact, I'd already decided that if I really enjoyed having the plug in my ass, I'd go even farther with my anal exploration this evening.

By this point, Dylan had me stripped down to my panties. Meanwhile, he was completely nude. Hiding a little behind my long, dark hair, I studied his erection. Though he was almost seven inches long, his cock wasn't extremely thick. Of course, it was a lot thicker than the plug I'd be starting out with, but I knew I could trust him to go slow.

"You're not getting shy on me, are you, Aria?" Flashing a smile, Dylan brushed my hair back from my face. Then he slid his palm over my left breast, moving lower before settling his hand between my thighs. When he discovered I was drenched, his cock pulsed with his own arousal. "Oh, definitely not shy!" His voice took on that smooth, seductive tone I loved.

A moan escaped my lips at his touch. "Just excited. I can't wait to play with my new toy!"

"Best give the birthday girl what she wants." Dylan cupped my face in his hands, drawing me to him for a kiss. I delighted in the way his lips lingered on mine. As our tongues met for a sensual caress, I grasped his cock and began gently stroking. Dylan's groan was muffled by our kiss, but he soon lost patience altogether, hurrying to yank down my panties. I squealed at his eagerness, which only made him laugh.

Once he succeeded in removing the undergarment, I watched, wide-eyed, as he pressed the damp crotch to his face and took a deep breath. After spending the past fifteen years engaging in mundane, vanilla sex, I was still surprised by Dylan's wanton revelry.

Finally, he retrieved the plug and its accompanying remote, as well as the bottle of lube. I quickly positioned myself on my hands and knees, with my cheek pressed against the bed and my ass in the air. Dylan knelt behind me, taking a moment to massage my buttocks. He often expressed appreciation for my voluptuous figure, and I knew he loved my ass in particular. I grinned when he planted a tender kiss on my left cheek, and then my right.

"Let me know if you feel any discomfort at all, okay?" His voice, soft and gentle, prompted me to quickly agree. The feel of his fingertip smearing lube over my puckered hole sent a delicious shiver through my body. "I'm going to ease it in now." He was careful, so careful, inserting the plug, and my flesh readily yielded. "How's that feel?"

"Great!" I assured him. I didn't experience anything spectacular from having the plug in my ass, but the sensation was far from unpleasant.

"It's all the way inside now," Dylan said. "Still feeling good?"

"Absolutely." As I spoke, I fought back a rising disappointment. While the plug didn't cause any discomfort, it didn't evoke any kind of pleasure, either. I hoped Dylan hadn't wasted his money on what I knew was a pricey toy. What if I had to tell him I didn't enjoy anal play? What if—

Dylan then turned on the plug's vibration, which immediately silenced all doubts in my mind. "Oh, my God!" I moaned. "Ooh, that feels fantastic!"

"I thought you might like that, baby." Dylan guided me onto my back, and as our eyes locked, he gave me a satisfied grin. Then he placed the remote in my hand. "I'll let you decide how much intensity you want."

I dared to increase the vibration, and as the toy hummed away inside my ass, my hips actually began rocking. "I never guessed it would feel so amazing!" The continual stimulation seemed to penetrate far past my inner walls.

Dylan stroked my hair. "It's going to feel even more amazing when I'm eating your pussy."

He wasted no time settling between my spread thighs. Normally, his lips and tongue moved at a slow, sensual pace, exploring my folds until my clit was desperate for attention. Tonight, however, he immediately went to work stimulating that bud of flesh, for he sensed how excited I already was. The moment he began licking and sucking my pearl, my eyes rolled from the intense pleasure of it, which the plug's vibration heightened even more.

"Yes!" I cried, grabbing his hair. He groaned in response, his hands sliding upward to cup my breasts. His mouth sounded almost obscene feasting on my pussy, and when our eyes met, I saw the hot lust in his stare.

I increased the plug's vibration until my spine arched and Dylan had to grab onto me in order to keep his mouth between my legs. My cries grew louder, reverberating throughout the room.

"I'm close!" I panted.

Of course, he could easily read my body's signals, so he knew just how close I was. His tongue moved at a relentless pace, lashing my clit with a fervency that always succeeded in pushing me over the edge.

The first fierce contraction drew a guttural sound from my lips. My ass clenched around the plug, again and again, which intensified the vibrating sensation. "Holy shit!" I managed to say just before another round of spasms seized me. I gripped Dylan's hair tighter while coming hard against his face, my thighs shuddering on either side of him.

When I finally released my hold, he teased my tender, swollen clit with just the tip of his tongue, making me tremble and whimper. Once he sat up, he made a show of licking his lips. Then he gave me one of his sweet smiles, so full of affection that my knees weakened. "I'm glad you like your gift."

I smiled back, still breathing hard. "I love it!" My smile widened to a sly grin as I added, "And now I want you to fuck my ass."

His eyes widened in astonishment. "Wow, I certainly wasn't expecting that!"

"You don't want to?" I searched his face, wondering what was wrong.

Dylan brought my hand to his lips, kissing my palm. "Of course I want to! But I don't want you to rush into something you're not ready for. I mean, that's a small starter plug, and you should probably play with bigger sizes before we..."

Already, I was shaking my head. "I'm ready, I swear! I even, um..." My cheeks flushed deeper as I struggled for the right words. "Before you came over tonight, I prepared for this by making sure I'm super clean, not just outside, but inside, too. If you know what I mean."

His tender smile returned. "I do, sweetheart."

"Then you understand it's not something I've suddenly decided in the last minute. I've been thinking about it." It was hard to express my thoughts coherently with the vibe still going strong in my ass, so I reluctantly used the remote to turn it off.

Dylan caressed my thigh, his expression thoughtful. "I just worry that you want to do this in order to prove you can be adventurous in bed, which is totally unnecessary. I know how adventurous you can be. And I can't help but notice that you asked for the butt plug only after I mentioned I enjoy anal and getting pegged."

I took a breath and let it out slowly. It was true that I'd begun considering anal play once Dylan revealed how much he liked it, but that wasn't the reason I wanted to go farther tonight. "I promise I don't feel pressured," I now told him. "I just want to try new things with someone I trust and love. And if I find I don't enjoy it, I'll let you know immediately."

Beneath Dylan's lingering hesitation, I could discern his excitement. Easing my legs upward, he instructed me to hold them aloft. In this position, I was spread wide and on display. After he carefully removed the plug and set it aside, I expected him to start preparing my ass for a fucking, just as he'd prepared it for the toy. Instead, he leaned forward, bringing his mouth to my hole. I gasped in surprise when he swirled his tongue over my flesh.

"Don't get shy on me now," Dylan said with a grin. Then he resumed licking and kissing me, clearly taking pleasure in the act.

And I had to admit, it felt really fucking good! With his hands, he spread me even farther apart, opening me wider. The sensation of his tongue working its way inside me reignited my lust while simultaneously easing my tension. Soon I was moaning and begging for more, pinching my nipples as my pussy grew sopping wet again.

Dylan lifted his head, wearing that same grin. He was obviously pleased I'd let him do something that made me feel so exposed and vulnerable. Now, he lubed up two of his fingers and began gently inserting them into my ass.

"I need to try to stretch you a little," he said. "Be sure to tell me if it hurts at all."

I nodded, making every effort to relax. The lubrication helped, but I certainly experienced pressure as he spread his fingers apart. He fixed his stare on my face, studying my reaction. Again, I nodded, letting him know I was okay. When I began rubbing my clit, which was still plenty sensitive, he made an encouraging sound. Before long, my need outweighed the discomfort of being stretched.

Once Dylan withdrew his fingers, he gazed at my ass for a long moment while stroking his dick to full hardness. I always loved watching him masturbate, so his self-pleasuring only served to increase my desire. The sound of his quickened breathing carried to me, and I couldn't help but grin.

Yet his expression bordered on serious when our eyes met again. "Are you sure?" he asked softly.

"Very sure!"

Finally, Dylan smiled, for my eagerness proved to be infectious. He used lots of lube while preparing my ass, and I watched him apply some to his cockhead as well. Then he moved to give me a deep kiss before whispering, "I want you on top so you can control the pace."

Though I'd never felt all that confident in the cowgirl position, I understood Dylan's request; I'd be far less nervous if I controlled how much of his cock I took, and how fast.

Moments later, I was straddling him, with his tip right at my hole. "When you start taking me inside," he said, "bear down with your muscles." While he spoke, his palms slid over my thighs. "That'll help you stay open."

"Okay," I whispered.

First, there was pressure. Far more pressure than I'd felt from Dylan's fingers. Fighting back a wave of anxiety, I kept going, making sure to bear down like he'd instructed. When my discomfort threatened to morph into searing pain, I gasped, then froze.

"Don't hold your breath," he reminded me. His own expression was almost anguished, for he hated to see me in pain. "I know the first time hurts, baby, and I understand if you want to stop."

"I want to keep going," I quickly replied. Though I realized I didn't yet have all of his tip inside me, I figured it would get easier once I managed that. "The pain's not unbearable."

As I continued sinking down, I was glad Dylan had asked me to be on top. If he'd been the one moving deeper inside me, I doubted I could have relaxed enough to see this through. Now, I pushed my body to what felt like its limit, and once I grew used to that, I found I could tolerate even more.

The moment I took his cockhead into my ass, I made a sound between a sigh and a laugh. It was the sound of abject relief.

Dylan smiled up at me. "You're doing great, Aria. Keep going slow."

Inch by inch, I accepted more of his dick. By this time, I'd broken out in a sweat, but when I was finally able to settle upon him, with his entire length inside me, the pain had lessened considerably.

"We're going to stay just like this for a while so you can get used to it," Dylan said. "It's totally up to you whether you want to start moving."

I searched his face. He seemed so calm and composed that I had to ask, "How does it feel to you?"

"Goddamn amazing!" he immediately responded. Seeing the unadulterated bliss in his stare made me even happier that I'd done this. He'd given me so much, satisfying my every desire, and I wanted to fulfill his fantasies in return.

We stayed still, simply basking in the sensation for a few minutes. I felt so incredibly full, but the pressure no longer hurt. When Dylan began massaging my clit, I couldn't stop myself from gently rocking my hips. In no time, the stimulation to my clit seemed to coax forth pleasure from all my erogenous zones, which apparently included my ass.

My moans became needy cries as I dared to move faster. Still, I didn't trust myself to ride Dylan's cock while it was buried in my ass. Instead, I carefully leaned forward so I could grab onto the headboard. In this position, Dylan had some room to thrust upward. "Fuck me, Dylan!"

I heard his gasp, and when he spoke, his voice was strained from the effort to hold back. "Aria, I'm not sure—"

"Fuck me!" I again demanded. My own voice made it clear I would tolerate no argument.

While cupping my ass in his palms, Dylan gave a thrust so gentle that it bordered on tentative. 

"Yes! Your cock feels so fucking good!" I wasn't lying; his cock did feel incredible inside me, to my absolute astonishment.

My words served to embolden him. He groaned through his heavy breaths while his hips took on a slow, graceful rhythm. But even at such a relaxed pace, I could tell his excitement was only building.

"Fuck, I'm not gonna last!" Dylan sounded apologetic, which was the last thing I wanted.

"Don't hold back!" I told him. "I want to feel you come inside my ass, baby!"

He let out a growl, never ceasing the pump of his hips. I had no idea if women could have an orgasm from anal sex alone, and I knew I wasn't anywhere close. But my climax was beside the point while I focused on Dylan's pleasure. Just as I loved sucking his cock, I loved offering him my ass.

He cried out before giving a final, deep thrust. I ignored the twinge of pain, instead relishing the way he pulsed inside me as he came. The sound of his helpless moans made me smile with my own bliss.

When Dylan's climax subsided, he gave my buttocks an appreciative squeeze. "My God, you are something else!"

Now I was the one grinning in triumph. He helped steady me while I eased off his dick, and I tried not to flinch when his cockhead finally slipped free of my hole.

I had no time to relax, however, for as soon as I lay at Dylan's side, he slipped an arm beneath me, drawing me near so he could rub my clit while sucking my nipple. My body, still hyper-aroused, instantly responded. It wasn't long before I was trembling, desperate to surrender to his mouth and his touch.

My second orgasm wasn't as powerful as the first, but it still inundated me with waves of bliss. While I came, I could feel his cum seeping from my stretched asshole, which made me feel deliciously filthy.

In Dylan's embrace, I shook and moaned. When he allowed my nipple to escape his mouth, I pulled him to me for a kiss. Though my clit continued pulsing from so much stimulation, and my ass throbbed with a dull ache, I managed a naughty grin. "You know what this means, don't you?"

He lifted an eyebrow, offering his own quizzical smile. "Do tell, Aria."

"Well, now that I'm not totally clueless when it comes to anal, I might be even more adventurous." With my arm around Dylan, I stroked his back, then moved lower. His eyes widened a little when I slipped my fingers between his ass cheeks to tease his hole. "And that means you just might get a pegging."