From Porn to Reality

My boyfriend Josh and I had just moved in together after dating for two years when I used his computer for the first time.

He wasn't home and my computer had crashed for some reason; it kept freezing and I was terrible at technology, so I gave up after half an hour of fiddling with it. I figured he wouldn't mind me using his—after all it wasn't like he was home and wanting to use it. I did the usual; checked my email, looked at Facebook, updated my status, browsed Amazon to see if there was anything new out that I wanted to read.

And then, because I'm naturally curious, I checked my boyfriend's favorites.

Most girls knew that their boyfriends looked at porn. I always assumed. In fact, Josh and I had watched a few pornos together—or started to, before we ended up getting distracted by doing our own thing. But it wasn't until I was looking at my boyfriend's favorites that I found out he'd been hiding something from me.

Josh was obsessed with anal sex. Every single porn site said Anal, Anal, Anal ... There was a folder labeled Toys that had link after link of things meant to go in the butt. Plugs, wands, vibrators, different lubes... I was in shock. I had no idea that this was what my boyfriend was into.

Then I found a link to the stories that he liked to read. I hadn't realized that Josh was much of a reader when it came to porn; he'd always been a very visual person. But the more I read, the more I thought I understood why he liked them. There was a lot of description. Lots of physical sensations described that you can't get from just watching a video. Going back and playing one where a girl was getting stuffed up her butt suddenly seemed a lot sexier now that I had phrases like "erotic stretching of her tight cavity" and "the slightly painful, mostly pleasurable desecration of her most forbidden hole" running around my head. What shocked me the most was how many of the stories said it felt good .

It was also pretty clear from the stories that my boyfriend was very into the girl getting it in the butt, rather than the other way around.

I’d never thought about having anal sex before. In fact, Josh had never touched anything more than my butt cheeks and neither had any of my boyfriends before him.

I always assumed that it would hurt—that's what everyone said, right? So why were there so many stories about how much women enjoyed anal sex? I’d thought anal- sex porn was just for men, that the porn stars would fake it feeling good because that's their job, and guys could whack off to it, leave their girlfriends alone and everyone would be happy. But I clicked on a couple of the bio pages for the authors of the stories and a surprising number of them were women. People, who said they were women, were leaving comments on the stories about how much they enjoyed anal sex and what plugs they used to get themselves prepared. Then I found an instructional story about how to make it enjoyable for the woman.

Lots of stretching of the hole, apparently, which made sense.

I started wondering what it would feel like. I read more stories. They were getting me hot and bothered, I had to admit. The dirty descriptions, the lust for something forbidden... the incredible intimacy of allowing someone into your most private area. Reaching down into my pants, I rubbed my clit, wriggling in the seat as I read story after story about women losing their anal virginity, about anal aficionados gleefully taking huge cocks up their butts, about small, medium and giant toys being wedged up people's asses. I was getting more and more turned on, my fingers working harder against my clit as my pussy got sloppy-wet. Then I clicked back on one of the movie links, carefully watching the woman's face as she took a fat cock up her butt.

I didn’t see even a hint of pain. Was anyone that good of an actress, that even if something really hurt, they wouldn’t show it at all?

"What are you doing?"

I jumped in my seat, shrieking with shock and horrified embarrassment. Josh was home. Early.

My panicked gaze looked at the clock as I tried to pull my hand out of my pants, turn off the suddenly loud porn, and close out every window I've opened while I realized that he wasn’t actually early at all.

I'd been reading about and looking at anal sex for hours. So, embarrassing myself further, I now fumbled around the computer, though I wasn’t sure what the point was.

He could clearly see what I'd been looking at, and now that my hand was out of my pants, I was acutely aware of the smell of my pussy on my fingers.

Finally closing out the last window, I turned his computer chair around, my beet-red face staring down at the floor.

"Sorry... Sorry. I… My computer wasn't working, and so I thought you wouldn't mind if I used yours and… I didn't… I wasn't… I didn't mean to, but I just stumbled upon some of your, uh, stuff. Some of your… Anyway, so I was looking at it… Oh my god I'm sorry." I covered my face with my hands, feeling tears spark in my eyes. Especially when I could clearly smell my arousal coating my skin.

I was so embarrassed. And horrified. Not to mention terrified that he'd be mad at me for looking at his private stuff. What if he felt like his privacy had been violated and decided he doesn't want to live with me anymore? Or worse, that he wanted to break up completely?

“Were you playing with yourself?”

I snuck a peek at him. He looked caught between angry and horny. Pissed and hopeful. I wanted to nudge him toward horny and hopeful… much better than pissed at me.

“Yes,” I whispered, keeping my voice low so that he had to lean in to hear me. “I was reading the stories that you have saved and they got me really hot. And then I started watching the pornos… and they got me really hot too. I’ve been looking at them for hours. I completely lost track of time.” My voice is husky, throaty. Seductive. Normally I just jump Josh when I want to get some. I don’t think he’s ever seen me shy before. Reluctantly desirous. I can see his pants tenting.

“What turned you on?” The tone in his voice was definitely veering toward hopeful.

I felt a small flutter in my stomach. Did I really want to do this? If I was honest with myself, it’s not just that I didn’t want to lose Josh. I was also downright curious at this point.

“The butt sex,” I answered, squirming a little. My hands were in front of me, holding each other and twisting. The whole situation was so uncomfortable and I was so horny. “The way the stories said it felt good. Thinking about it makes me feel like I’m being so bad… naughty. I started to wonder…”

“You started to wonder what?” he asked as my voice trailed off. There was a desperate edge to his, the kind a person gets when they think their dreams are about to come true. Which, his definitely were.

“What it would feel like if you put things in my butt,” I whispered huskily.

“Oh Jesus, Penny.” Josh moaned, reaching for me. His arms went around me, hard and demanding, and he kissed me. Deeply. Passionately. His mouth seemed to want things from me that I was terrified to give, but also afraid not to. I kissed him back, my response fueled by my own desperation and passion… my needy curiosity.

“I’m not sure I want to have butt sex,” I said, pulling away. “But I wouldn’t mind playing… and if it doesn’t hurt, then maybe…”

“It won’t hurt,” he promised recklessly. “We’ll do everything right. I’ll make you feel so good.” Then he kissed me again, bending me back in his arms with the force of his passion. I’d always thought Josh and I had a pretty great sex life, but the stark need in his body was something new to me.

“Go sit on the bed,” he directed, letting me go. Nervously, I did as he said and watched him rummage around in his side of the closet, eventually pulling out a box that had been covered with old sports equipment.

“What is that?” I asked, as he carried it over.

“A whole bunch of stuff I thought I’d never get to use,” he replied, winking at me.

I smiled nervously back at him.

He set the box down on the floor next to us, totally in tune with my response. “It’s okay baby, we’re gonna take this slow.”

I felt like an inexperienced virgin as he pushed me back onto the bed, kissing me hard. His hands moved under my shirt, kneading my breasts, pulling on my nipples which he knew were super sensitive. My pussy gushed in response, something inside my body relaxing a little. I trusted Josh. He would never hurt me, not even to fulfill a fantasy of his.

We were making out and I was getting into it, nibbling on his lip and sucking on his tongue in the way I knew he liked. My legs hung off the edge of the bed and he stood between them, leaning over me, hands up my shirt. I wrapped my legs around him and pulled him against me, rubbing our crotches together. Josh’s cock was like a steel rod in his pants.

Swiftly, he pulled my shirt off and undid my bra, freeing my breasts. As his mouth fell on my sensitive nipples, his hands began to undo the button of my jeans. It wasn’t long before my pants and underwear were both gone, and he was groping my ass. The tip of his finger pressed against my virgin back door, rubbing gently.

It felt… wrong.

Good.

Scary.

Exciting.

I humped my hips against him, rubbing my wetness against the hard bulge in his jeans. I was going to cream myself all over his pants if this kept up. The suckling of my nipples was driving me crazy.

Then Josh let them go, to my disappointment and relief, and knelt between my legs. His eager mouth sucked my pussy lips, sliding his tongue up and down my wet slit, flicking my clit with the tip of it. I moaned and wriggled as he pushed my legs up so that they were bent at the knees, which were now above my chest. Although this opened my ass to him, he didn’t go there immediately. Instead, he teased my hot, wet, needy slit. I was a quivering pile of anticipation, needing an orgasm and at the same time scared of what he might do to my exposed anus.

When he moved his mouth down there, his tongue licking at the sensitive spot, I gasped at how good it felt. Strange and perverse, but good. I shuddered, my body shaking with the overwhelming need to come and the strange pleasure of my boyfriend’s tongue on my final frontier.

“Oh Josh,” I moaned as his tongue pressed against my hole. It ached, somehow, deep inside of me. My pussy felt empty and needy. “Oh fuck me, just fuck me please.”

“Shhhh,” he said. “I’m enjoying this. Aren’t you enjoying this?”

“Yes Josh, but I need to come,” I pleaded, keeping my knees high in the air. His tongue lashed my anus, tormenting me wonderfully.

“Be a good girl and you’ll get to come soon,” he said soothingly. I heard him doing something in his lap and then felt something slick and hard pressing against my crinkled hole.

“Josh,” I said, my voice quavering.

“Just relax Penny,” he crooned. “We’re going to take this slow.”

I groaned as my backside opened up for him, the pressure on my tight ring was too much to bear and the tip of his finger slipped inside me. Automatically I clenched, biting my lip. There was a short, sharp pain when he first pushed in, but now it didn’t hurt. It just felt uncomfortable. A strange, stretched, full feeling… It was just like the stories said. Except that this was just one of his fingers, I couldn’t imagine his dick not hurting.

“How does that feel?” he asked softly, all care and concern.

“Strange,” I answered. “Not bad… but strange.” I gasped as he pushed his finger deeper. “Oooooo… God Josh, that feels so weird.”

“Good weird?”

“Yeah, I guess.” The truth was… it felt erotically forbidden and kind of very good. Gently he pumped his finger back and forth, fucking my ass with a single digit. I could feel his hot breath on my pussy, which was now even wetter than before. I couldn’t deny that I was starting to enjoy this. The stretching of my tight hole was so incredibly intimate… Knowing that he was watching himself finger-fuck my ass, the view right on eye-level for him, was even more so.

“Fuck baby, your ass is gripping my finger so tight.”

I groaned again as he delved a little deeper, past his second knuckle. I could feel every bump and ridge on the digit as he pushed it into me. My insides automatically clenched down but his finger was so well-lubed that he pushed right past my tight barrier. The sensation is thrilling and uncomfortable.

“Oh Josh!” I gasped again, writhing as he started licking my pussy while his finger moved back and forth in my most intimate hole. I felt decadently naughty, the kind of bad that I hadn’t felt since I was a little kid doing something that I knew I’d get into trouble for if I got caught, but that I just had to do anyway. As he ate my pussy and finger-fucked my ass, I felt my orgasm building. The sensation of him inside my virgin hole just added to the pleasure, the full feeling intensely erotic.

When he slid a second finger in beside the first, I yelped as my tight ring stretched to accommodate it. It seemed to take a lot less time than it had for the first one, and then he had both of them moving back and forth inside my ass, filling me up as he sucked on my clit. I was moaning non-stop now, my orgasm building in my pussy and in my ass, the full feeling in my stomach making the sensations seem stronger and deeper in my body than ever before.

My whole lower body clenched down, convulsing as I came. Josh’s slick fingers weren’t at all stopped by my squeezing hole, they kept pumping in and out and the erotic glide made me thrash with ecstasy as my pussy exploded. I could feel my orgasm spreading heat through my entire lower region, from my waist down through my thighs, the extreme pleasure overwhelming.

As I started to come down from the wonderful high, Josh continued his ministrations. I groaned. It was hard to stop the aftershocks of my orgasms when he was still penetrating me like that.

“Baby, baby, come fuck me,” I begged him. “Just come fuck me.”

“Hold on,” he said. He removed his fingers from my ass and my entire body finally slumped and relaxed.

I heard more noises; it sounded like he was opening a box. I kept my eyes closed and concentrated on how good I felt. My butthole still felt a little strange… stretchy and maybe a little uncomfortable. But kinda good too. The way my pussy felt after great sex.

Something hard and insistent nudged against my tight bud and slowly pushed into me. I cried out as he filled me with a toy. It wasn’t wider than Josh’s fingers, but it stretched me out again, and my anus snapped shut around it, gripping the base of the toy tightly.

“What is that?”

“It’s a butt plug.” Josh stood between my legs, stripping quickly. The plug was heavy and full inside my hole. My ass kept tightening around it, testing its determination to stay inside me. It seemed very determined.

Josh helped me wriggle back—which jostled the plug in my backside and made me squirm with the new and pleasant sensations it created—until I was fully on the bed. He fell on top of me, his eager cock going straight for my overheated and ready pussy. Oh God… With the plug already inside me he felt so much bigger as he pushed in, the ‘full’ sensation quadrupled.

“Fuck you’re tight,” he groaned, reaching down past my thigh to grip my butt cheek, pulling the flesh out of the way until his fingers found the tip of the plug. Twisting and pulling, he made it move inside me as he forced his cock deeper into my pussy.

“Oh Josh!” My nails dug into his shoulders as I moved beneath him. The throaty moans coming from me were raw and carnal. Both of my holes clutched at their loads spasmodically. I was filled to the brim, bursting with sex and erotic intent, brazen with a plug buried between my cheeks as my boyfriend pounded me into the mattress.

The plug moving inside me with his thrusts only increased my enjoyment. When I came again, it was even more intense than before. I screamed my orgasm, digging my nails into Josh’s back as I arched beneath him, my insides rippling around the plug and Josh’s cock, the exquisitely forbidden sensation of a full ass making my culmination all the more sweet.

Fortunately, Josh didn’t last through my orgasm. I was pretty sure that if he’d kept thrusting at me after I came again, I would have passed out from the sheer ecstasy. But my writhing body, the anal play, it had all gotten to him on an intensely fulfilling level and he creamed my pussy as I bucked beneath him, groaning his own completion. I was pretty sure we were both picturing what it would be like when he came in my ass.

As we caught our breath, Josh kissed me, slowly rubbing his hips against mine as we shuddered out the last of our orgasms.

“Did you like that?” he asked. He stroked my ass cheeks, and I could feel the tips of his fingers nudging the plug in my butt.

“Yeah,” I admitted, kissing him back.

“God, this is so hot.” He nuzzled my neck. “I can’t wait to be inside of your ass.”

His words sent a shiver of anticipation and anxiety through me.I kind of couldn’t wait either.

At Josh’s request, I left the small plug inside of me for several hours. And I let him be the one to take it out. The sensation of its removal left me feeling sore and empty. That night, before bedtime, I laid on my stomach and let him use his fingers to play with my ass. He thoughtfully also inserted some into my pussy and fingered me to a fantastic orgasm.

The next afternoon he insisted on plugging me again. I was starting to get used to the full feeling of a butt plug inside of me. That night, during foreplay he stuffed my ass full of beads on a string, and pulled them out in the middle of my orgasm, creating the most intense wave of ecstasy I’d ever felt in my life. I still wasn’t entirely sure that I hadn’t blacked out for a minute.

By the end of the week, he’d talked me into letting him put the medium-sized plug in my ass. My tight hole stretched and it was uncomfortable at first, but he made it up to me with fantastic oral sex. The full feeling in my ass, the twisting of the plug as his tongue worked over my pussy, all contributed to a fantastic explosion of delicious ecstasy.

The medium-sized plug took some getting used to, but the feeling of having it jostling around inside me ended up turning me on. I jumped Josh’s bones almost every night.

A few days later, I finally agreed to let him deflower my ass.

“I want to be in control,” I reminded him nervously.

“Absolutely, baby. Whatever you need.”

Yeah, he’d agree to anything to get inside my ass. In fact, his obsession with it had become rather flattering. He knelt behind me, while my hips were propped up with a pile of cushions on our bed, using two fingers to lube up my hole.

I closed my eyes and concentrated on the erotic feeling of his fingers sliding in and out of my ass. The constant anal play got me off, but I was still a little scared. That his fingers caused no discomfort helped. Heat started building in my pussy the more he fingered my asshole, and I started pushing my hips back against him.

“Okay,” I finally said. “I think I’m ready.”

Quick as a whip, the head of Josh’s cock pressed against my tiny hole. It felt monstrously huge compared to me.

“I’m holding still,” he said.

That was our agreement.

“You just move when you’re ready.”

Experimentally, I pushed back against him. The groan he made was very nice… The sharp stab of erotic pain was less so. Sure, it felt good in some ways, but it also hurt. I eased away again.

Josh was being great, very patient. He didn’t even sigh with disappointment. If he had I, might have said ‘fuck this’.

Instead, I took a deep breath, carefully relaxed my muscles, and pushed back again. This time it was a little easier and I was able to push past that first sharp jab of pain. One more deep breath and I felt his head pop inside the tight ring of my anus. Josh’s quick gasp let me know how much he liked that. I wiggled a little, adjusting to the sensation of him in my ass. It was very different than the plug… I could practically feel the heat emanating from the head of his cock as I squeezed it. Josh’s hips jerked and he pushed inside me. Then it was my turn to gasp.

“Sorry, sorry baby,” he said immediately, pulling himself back out. I was sure doing so took monumental effort. What a sweetie.

“It’s okay,” I reassured him. “It didn’t hurt.”

In fact, it gave me the courage I needed to push back a little more, feeling his cock pressing into my lubed hole. Thank god for all the preparation he’d done on me. I was actually able to enjoy the feeling of my ass opening up for him. Once I had several inches of him in me—about as much as the plug—I let myself slowly pull back off of him.

Oh! Wow.

That was a weird sensation. The feeling of his cock receding from my tight anal cavity was not like being fingered. As the sensation of fullness was dragged back, it felt like having air drawn out of my lungs. I pushed back onto him, almost clinically analyzing the way it felt. Josh’s fingers dug into my hips and he groaned again.

Well, he’s certainly enjoying this.

After another minute of rocking back and forth, working his erection into my tight hole, I realized that I was too. There was something deliciously naughty about what we were doing. And intimate.

The feeling of Josh’s cock in my ass was almost indescribable…

A penis could become so rigid and hard, and yet the surface of it would always be silkier and softer than any toy. As much as the quivering of my ass muscles was massaging him, the soft stroking of his skin against my taut tunnel was massaging my insides. I felt full with him there, as if an unknown part of me had been ignorantly neglected; I hadn’t missed it before I’d known it existed, but now that it was there, it felt right and I didn’t want to leave it alone and untouched ever again.

I loved the sensation of him in my ass, the hot lubricated glide of his cock through my tight, clutching ring, the intimate sensations that we were giving each other.

When my ass cheeks finally pressed against his body, I deliberately clenched down with my inner muscles, engulfing his entire cock with a rippling spasm of sensation. Inside me his hard shaft jerked and rubbed, his hips pressing against me as he instinctively tried to bury himself even deeper.

“Oh fuck… Penny, you have no idea how amazing this feels.”

“Oh yeah?” I asked playfully as I pulled myself forward, then slammed back. The slight pain in my sudden movement was more than worth Josh’s reaction— his clutching hands and ardor-filled moan. In fact, that flash of hurt in my ass actually turned me on even more, the building ache in my pussy somehow fueled by the jolt.

I reached beneath myself and begin rubbing my clit as I started rocking back and forth in front of Josh. I was sure he meant to let me have control, but I could feel his hips start to move…

“Oh!” I cried out.

He stopped immediately. “Are you okay? Did I hurt you?”

I groaned. The wonderful feeling had ceased when he’d stopped moving. “Keep going! Fuck my ass, Josh, just please fuck my ass!”

Those were the magic words. Suddenly, I had one hundred and eighty pounds of male fantasy pile-driving into my rear entrance.

And I loved it. The sweet intensity of his need, the way he took control of me from behind, the ravaging intimacy of giving up my ass to him. I relished the feeling of his cock pounding me, pushing past my squeezing hole. My fingers worked feverishly over my clit, the orgasm building between my legs spurred by the steady anal-fucking my boyfriend was giving me.

Josh rode me from behind and I gripped his cock with my ass for all I was worth as the hot need between my legs built to unbearable heights. The full sensation in my backside seemed to spread heat through my entire lower body as my insides tightened and released. I kept rubbing my clit, crying out my passion as I came, my butt shuddering against the invading cock.

That was when Josh lost complete control of himself and thrusted hard, practically impaling me on his dick. It was now rock-hard, like a plug of steel up my tight hole, and I could feel it jerking inside of me as he groaned, and ground himself against my butt cheeks. My insides convulsed, and I cried out again as I stopped rubbing my clit because there was too much overwhelming sensation already going on. But the pleasure didn’t stop. I was still orgasming as Josh unloaded into my ass, completing my defloration.

Finally, he collapsed on top of me, his hard cock still deep inside my no-longer-virgin backside. We panted in unison, slowly coming down from our bouts of ecstasy together. Josh nuzzled my back with his face and I twitched at the odd feeling of him shrinking inside of my ass.

“Ooooo careful,” I moaned as he started to pull away. “That’s a little sore.”

Josh caressed my ass as he slid out of me. I could feel my hole closing up again in relief.

“Are you okay?” he asked.

“Oh yeah,” I said. I turned my head slightly to smile at him. “In fact, I think—after a day or two of rest—that I’d like to try that again.”

My boyfriend’s face lit up like I’d just announced year-round Christmas.