Michelle

I laughed back at her teasing comments. In a sense it was somewhat true. With Michelle being 21, I was almost 9 years older than her. I decided to play along.

"Yeah," I said, faking a yawn. "I think I do need to get some sleep. Maybe you can call another one of your 'internet friends' to pick you up."

"Oh yeah?" she said, moving a little closer. "And then maybe I'll let one of my other 'internet friends' be the first one to fuck my tight little virgin ass?"

I stared at the ceiling for a brief moment before turning my head to face her.

"Well, okay..." I began. "If you really want me to.... then I guess....we can do it."

Michelle could sense the playfulness in my voice and she smiled in response.

"Really?" she asked hopefully.

"Yes. However, I will need a little bit of time to...recover."

"Oh, that's okay," she countered back with a smile. "I'm actually keeping myself pretty entertained at the moment anyways."

After she glanced downward, I followed her line of vision to see her fingers busy at work between her legs. I let out a short laugh before speaking again.

"Wow," I exclaimed. "You are...one...horny...girl."

Michelle just shrugged and cast me a bashful smile. That's when I noticed her other arm behind her body.

"Hey," I said, narrowing my eyes suspiciously. "What are you doing back there?"

"Nothing," she answered with a giggle, unable to maintain a straight face. I sat up and peered down at her body to see the fingers of her right hand tucked in between her ass cheeks. I moved down the bed to get a better look as she continued shamelessly fingering her own ass and pussy in unison.

"You...dirty...little...girl," I said with amazement as I pulled back one of her fleshy cheeks to give myself a clear view of her slender finger sliding in and out of her tight little asshole.

"So," she said, giggling. "Are you ready yet?"

"Oh, I'm getting there."

As I continued to take in Michelle's sexy display, my hand drifted downwards to grasp my growing cock which was already beginning to stiffen once again. She smiled back at me before rolling over onto her stomach and then rising up onto all fours. As I felt my dick grow larger in my hand, my eyes remained locked on Michelle as her fingers continued to penetrate her own pussy and ass in tandem.

"Hold that thought," I said, reaching over to the night table.

I slid open the drawer and retrieved a bottle of lube that I had stashed inside. As Michelle caught sight of the bottle she smiled in response.

"Are you sure you're ready for this?" I asked, moving back into position behind her.

"Yes!" she answered emphatically, dispelling any doubt in my mind.

I grinned as I flipped the bottle open. Holding it up, I then began to drizzle the clear liquid down onto Michelle's ass at the bottom of her tailbone. She let out a faint giggle as the lube started a slow trickle down between her cheeks, making its way to her finger which was still buried knuckle deep in her own ass. As she began to withdraw her finger, the fluid collected around the digit, coating it as she pushed it back inside.

"Oooooohhhh," she purred, sliding her lube-coated digit in and out of her virgin asshole.

I watched with fascination as I squirted some of the lubricant into my hand and began stroking my shaft, covering it with the slippery substance. I moved closer, my cock now throbbing in my hand, aching to enter Michelle's irresistible little orifice. I peered down at her finger, glistening with lube, sliding in and out, forcing itself deeper with every thrust.

I reached down and took hold of her hand, gently prompting her to withdraw. Reluctantly she did so, pulling her finger free with ease. I could almost sense the anticipation building in her body as she waiting. After months of dirty emails and phone sex conversations it was about to happen. I was going to fuck Michelle's ass.

Gripping my dick firmly, I slid the head up and down her wet crack before finding her tight little star. Slowly, I began to push.

"Shit," I cursed, as my cock slipped down towards her pussy. "I think I used too much lube."

Again I tried, only to have my dick slide up in between her ass cheeks eliciting an amused laugh from both of us.

"Okay," I stated with firm resolution. "Third time's the charm."

Holding my clenched fist against her asshole, I slowly pushed forward, butting the head of my cock against her willing but difficult ass. I bit my lower lip with dedicated concentration as I felt her tight hole gradually give way and allow my dick to penetrate her most private of body cavities.

"Uhhhhhhhggggg," Michelle moaned, as my head slipped inside her ass. I couldn't tell it the moan was from pleasure or discomfort.

"Play with you pussy," I suggested, pausing only briefly before pushing more of my cock into her asshole.

She took my advice, but I could sense something was wrong. Her body seemed tense and apprehensive.

"Are you okay?" I asked, briefly halting my cock's anal invasion.

"Yeah," she answered back meekly and unconvincingly. "Keep going."

Again I resumed, using one hand to slowly guide my dick deeper into Michelle's clenched butthole. Perhaps I was a bit overzealous, or maybe she just wasn't ready, but after a few seconds more, she crawled forward off my cock holding her hand gingerly against her recently reamed hole.

"Ahhhhgggg," she cursed in frustration. "I can't...It's...too painful."

Although I was disappointed, I tried to hide it in my concern for Michelle's well-being.

"That's okay," I offered in condolence. "Girls usually have a hard time when they try it for the first time."

Michelle let out a bit of an histrionic whine as she glanced back over her shoulder with a timid, puppy-dog expression.

"But I want to do it sooo bad," she pleaded, beating her hand against the mattress in frustration. "And it...did feel...good. It's just that...."

"I know," I said, offering comfort. "It's okay. In fact, let's try something else."

Michelle's interest seemed to be peaked as I once again returned to the night table beside my bed. This time I rummaged a little deeper to find what I was looking for. Behind the condoms, handcuffs, and blindfolds and other paraphernalia, I found what I was looking for.

"Stay there," I told Michelle, who was now in a side-lying position facing away from me.

From the drawer I pulled a 5 inch long, pink butt plug that I had purchased off the internet some time before. I had bought it for use with a previous female 'friend' although it had arrived too late for us to make use of it. I set it on the bed, as Michelle remained lying on her side, obviously curious about what I had in mind. I then retrieved another condom tore open the package. I noticed that it smelled like oranges. 'It must be from the tropical variety pack I had bought last month,' I thought to myself as I rolled it onto my dick. I applied the lube liberally to both the plug and to my rubber-covered cock before inching back to Michelle's waiting body. As my slippery fingers began to explore her pussy and ass, she sighed contentedly. I coaxed her to roll over a bit in order to gain access to her pussy, which I penetrated with my fingers before replacing them with my dick. Once Michelle's pussy had swallowed my entire length five of six times with slow methodical plunging, I picked up the pink, rubber plug and placed the narrow tip against her noncompliant asshole.

"Oooh," she blurted out as she felt the tapered point poke past her wet, muscular rim.

With my cock completely buried inside her, I began rotating the plug as I slowly pushed it up her ass. As the plastic toy was much more streamlined and quite a bit smaller than my dick, it slid it with little effort. Michelle shifted her body and sighed with pleasure, obviously enjoying the sensation of having both holes filled.

As my hips began to rock with short, quick thrusts, I forced the plug deeper causing her asshole to stretch wider and wider. It was almost completely inside her now as she squealed in ecstasy. The widest portion of the toy soon passed her tight, muscular ring allowing it to clamp down around the much narrower base that then followed. I smiled with satisfaction, seeing the pink, rubber toy completely embedded in Michelle's asshole with only the flat base visible.

"How does that feel?" I asked, rotating the plug around inside her ass. "Mmmmm," she purred lustfully. "So fucking good!"

As I tugged on the buttplug, I began fucking her pussy with increased vitality, pausing every now and then to wiggle the plastic toy around insider her ass.

"Oh yeah!" she called out. "Fuck me! Fuck me hard!"

Again I complied, holding the plug firmly buried inside her as I slammed my hips into her ass.

"Uh! Uh! Uh! Uh! Uh!" she blurted out with each thrust, until I felt her body tense once again.

And it was then that I felt the strangest sexual sensation that I had ever felt. Her pussy clamped down around my cock like a vice. The force was so strong I felt as though she might actually sever my dick from my body. I tried to pull out, but the iron grip of her cunt held me in place until her orgasm subsided. It was only then that I could resume my thrusting, bringing me closer to my second climax of the night.

A few more forceful thrusts, and I slammed my body into hers, groaning uncontrollably as I spilled a thick load of cum into the condom. 'Fuck, I hate condoms,' I thought to myself, as I caught my breath, my dick still buried inside Michelle's ravaged pussy.

Slowly, I extracted the plug from her ass, followed by my dick from her pussy. Michelle rolled over smiling, eyes closed in contentment. I laid back on the bed, leaving the condom on my dick, but setting the buttplug on the night table beside me.

I was now officially tired.

I hoped Michelle, felt the same way, because there was no way I was going to go another round, and I definitely was in no mood to drive her half way across the city to take her home. Luckily, she curled up beside me and closed her eyes.

Soon we were both asleep.

* * * * * * * * * * * * * * When I awoke it was still dark outside. I rubbed my eyes drearily as I glanced over at the clock.

"5:38," I groaned, rolling back over only to find myself blocked by Michelle's sleeping body.

I cursed silently to myself as I struggled to find a comfortable position. As much as I loved "sleeping" with girls, I hated actually sleeping with them. I rolled over and closed my eyes again, vowing to buy a bigger bed.

* * * * * * * * * * * * *

When I awoke next, it was light outside. I could hear the birds chirping. Beams of light were shining through the open spaces in my blinds as I buried my head under the covers to escape back to my isolated world of comforting darkness.

Then I felt a body shift next to me and I remembered that there was someone else in bed with me. I groaned silently to myself, not wanting to engage in the menial small talk that often follows nights of sensuality. For a moment I thought that if I just pretended I was sleeping then she would call a cab and go home.

Ten minutes passed.

Then twenty minutes passed.

Then thirty.

Then an hour. I was growing restless.

I rolled over and looked at Michelle. She seemed restless but sill sleeping. Drearily, I hauled myself out of bed and went to the bathroom, hoping that after a long shower I could return to find her gone with a nice succinct note in her place.

No such luck.

As I came out of the bathroom, a towel around my waist, I was caught by a sudden rush of cold air that reminded me to close the windows before going to sleep. As I made my way down the hall back to the main room, I saw Michelle curled up in the blankets with her head poking out from above the covers, smiling with a sleepy expression.

"Good morning," I said, climbing back into the bed, still a bit damp from the shower.

"Mmmm, Morning," she replied, stretching her arms out in a prolonged yawn.

About 30 minutes of casual conversation then ensued, with neither of us mentioning the events of the previous evening.

"So...." I began, sitting up in bed. "Do you want a ride home?"

Michelle groaned and cast me a pouty expression.

"What?" I asked, furrowing my brow with fake concern.

I knew what she wanted. For some reason girls seem to love morning sex, and I knew right then that I was going to have to give her at least one more orgasm before I could take her home.

"Oh?" I continued playfully. "Is there something else you would like before you go?"

"Maybeeeee....," she replied sheepishly, pulling the covers up to half cover her blushing face.

"And just what would that be?" I asked, crossing my arms over my chest. "I...want to...try it again."

"Huh?" I stammered, completely caught off guard by her response.

"I want to try it again," she reiterated, this time answering with more conviction.

"You mean...?"

"Yes."

"In your...?"

"Yes!"

"Wow," I exclaimed, shaking my head in disbelief. "Umm, okay. Yeah, I guess we can try it again..."

"Oh? So what? Now you don't want to fuck my ass?"

I laughed as I waved off her insinuating comment.

"No, no, no. Of course I want to. It's just that...If you couldn't handle it last night then..."

"Well I want to try," she stated firmly, cutting me off.

I could tell Michelle was used to getting her own way. I tossed my hands up in resignation.

"Okay, then. Let's do it. But first....."

"What?" she asked, her eyes widening with curiosity.

"I think...," I continued, smiling. "I really want you to put my dick in your mouth."

Michelle smiled back. I knew she liked my idea.

Without a word, she moved down the bed, pushing the covers off my naked body. Just the thought of having Michelle's pouty lips wrapped around me once again had already started the familiar rush of blood into my dick. As I settled back into a comfortable position, she placed herself between my legs, lying on her stomach and taking my growing cock in her hand. She gave it a few slow strokes as she glanced up at my expecting face. I placed my hands behind my head, settling back with a contented smile as I watched her plant a soft kiss right on the end of my dick. Michelle let her lips linger there for a moment before slowly allowing them to spread, taking my head into her warm, wet mouth. She finally broke eye contact as her lips descended down my shaft, her tongue sliding down the underside. As she reached the base, where her fingers were wrapped around my cock I could feel her tongue-ring flicking around inside her mouth.

"Play with my balls," I suggested as I watched her pouty, pink lips gliding up and down my wet shaft.

With her other hand, she reached down and cupped my sensitive balls, stroking her fingers along the underside before giving them a gentle squeeze. I winced as she kept squeezing, perhaps a little bit too hard. I was about to ask her to stop when she lowered her head and ran her tongue over my balls, sending a pleasurable shiver throughout my body. I moaned in approval as lips and tongue covered them with soft licks and kisses before returning her attention to my dick.

"Mmmm, you're pretty good at this," I said softly as her lips once again wrapped around my cock.

"Hehe," she giggled, her cute voice muffled by my dick in her mouth. "Thank you."

As she started to compliment her sucking lips with slow, long strokes of her hand I could feel myself swelling in her mouth. I reached down to move a few strands of hair out of her face, giving me a better view.

"I like to see," I explained when she cast her eyes up at me with curiosity.

After about ten straight minutes of Michelle's oral handiwork, I was sufficiently worked up to escalate the situation.

"Okay," said, grabbing a condom from the night table. "I want you to get on top."

Compliantly, Michelle gave my dick a few more strokes before rising up to her knees.

"Which way do you want me to face?" she asked as I rolled the condom onto my throbbing, wet cock.

"That way." I ordered, referring to the end of the bed.

She gave me one more amorous smile before throwing a leg over my body, holding herself in a squatting position directly above my waiting dick. As I held it pointing upwards, Michelle reached down to guide the head into her moist, little hole, slowly lowering her body downwards. Her pussy gripped my cock as I watched her lips sliding down my length. Once she had fully descended and my cock was firmly embedded inside her, I tentatively released my hold on my shaft.

Placing her hands on my thighs for balance, Michelle started moving herself up and down on my dick, showing a remarkable display of leg muscle endurance. The feeling was amazing, as I watched her little round ass repeatedly ascend and descend, her pussy gliding up and down with ease. I noticed her breathing getting quicker as she increased the pace.

"Will you play with my ass?" she gasped, looking back half-way over her shoulder.

"Maybe..." I answered, although I was already licking my fingers in preparation. "...if you say please."

"Please," she shot back with hesitation. "Please play with my asshole."

Those few words turned me on even more and I quickly removed my wet fingers from my mouth and placed them over her tight, anal opening. Michelle purred with gratitude as massaged her tiny little butthole with slow, circular motions of my thumb.

"Inside," she gasped again. "Put it inside."

Again I complied, replacing my thumb with my middle finger, wriggling it past Michelle's tight muscular ring. She tossed her head back in lustful bliss as she felt my finger sliding smoothly into her asshole.

"Oh yeah," she moaned, leaning forward to allow me to go deeper. "That's what I like!"

As Michelle continued bouncing up and down my cock, I held my hand stationary allowing her asshole to slide and down my finger as well.

"Mmmmm," she purred, growing more aroused by the second. "I can't wait to have your dick in my ass."

I felt myself getting close to orgasm.

I'm going to cum soon," I warned, nearing climaxing due to Michelle's twitching butthole tensing around my finger.

"Noooooo," she cried out, stopping all movement. "Not yet."

I was on the brink. I felt as if anymore movement at all would send me over the edge.

"Okay," I gasped, trying with all my willpower not to cum. "Get off. Slowly."

I took a deep breath as Michelle cautiously lifted herself off my cock. As I slipped free, my dick fell to my stomach with a wet "slap". She sat kneeling in front of me impatiently as I waited for my impending climax to subside.

"Okay," I said with relief. "I think we're good."

"Yeah," Michelle said, laughing. "That was a close one."

"Yeah, sorry about that. Now...where were we?"

"I think..." Michelle began, as a mischievous smile appeared on her face. "You were about to bend me over."

"Oh was I?" I retorted in a teasing manor.

"Yep!" she piped out cheerfully before a shy expression once again her. "And..."

"What?" I prompted.

"Could you use the buttplug on me again?"

"Of course! So I take it you enjoyed that last night?"

"I loved it! Although...I still want to try your dick in my ass again."

"No problem," I stated, reaching over to grab the pink, rubber plug and the bottle of lube. "I'll use the plug first though. It should help you relax and get used to the feeling. It'll make it easier when I actually fuck you in the ass."

Michelle could not hide her enthusiasm.

"How do you want me?" she asked, her face beaming with excitement.

"On your hands and knees," I replied simply, flipping open the cap on the lubricant.

As Michelle assumed my favourite position, I covered toy with lube in preparation. A few seconds later we were engaged in a replay of the previous night with my dick in her pussy and the pink, rubber plug buried snugly in her tight little ass.