Ethan's Grace - Anal Edition

This is a short stroke-story based on characters in a series called "Amazing Grace". It is not necessary to read the other series in order to follow this story, but if you want more background on the characters, you'll have to look there.

Thanks in advance for your support and comments.

Ethan's Grace -- Anal Edition

I'd been working her up to it.

I started by getting her to tell me what her hangup was with anal sex. The last thing I needed was to step on that land mine. It was a botched attempt; a half-ass ... yep, pun intended ... effort at something that shouldn't be that difficult to accomplish. I've always been astounded by how many guys fuck this up.

The thing is, it's not for everyone. A good buddy of mine once said that it was a lot like cotton candy. It looks enticing from a distance and it tastes good, but it's hardly worth the effort to make it, or the mess afterward. I thought that sounded like a fair analysis. He wasn't the brightest individual, but he got that one right.

I don't spend a lot of time speculating why I want to do it. I just do. It's not something I need to do on a daily basis, but I want her to be willing to give it to me that often, if that's what I want. And because this was so difficult for her, I wanted it even more. Maybe I'm just an insecure prick who needs a reminder of his partner's devotion. Or maybe I just crave that level of intimacy with Grace. Either way, I'd made my decision, and I was willing to make the effort and deal with the mess to get my cotton candy.

It helped that our sex life was great. And active. I'd associated everything we did with sexual pleasure for her and she was responding like one of Pavlov's dogs. It was working out great for us. And when she was like that, I could introduce practically anything to her and she'd be open to it.

God, I love this woman.

Case in point, Grace was starting to become a greedy slut about having her pussy licked. I've never known a woman who hasn't. I would've curbed that behavior right away if it hadn't been for the fact that she'd only just gotten over having this done to her and this was still real new. I can sort of understand her enthusiasm. It was like after getting blown for the first time. I wanted it all the time. And I like pussy, so this didn't really pose a problem for me. In fact, I saw real value in it as a means to an end. The next time she was squirming and panting, silently begging for me to finish her with my tongue, I simply slipped my finger past her anal ring before giving her what she craved. She was so horny, she couldn't have cared less.

It got so I was doing it every time I went down on her. I'd take it a little further each time until it just became part of the whole routine. When it progressed to the point of rimming her anus with my tongue, I thought she was going to climax from that alone. It was a pretty encouraging sign.

Grace has her share of hang-ups. Don't get me wrong, she's getting better, but when it comes to anal sex, there is still a strong association that is hard to overcome. Like a lot of girls I've known, somewhere in the recesses of her mind she believes it's wrong. Dirty. Not something nice girls do. The best way I knew to convince her that I didn't think of it that way was rimming. It was working. And with that hurdle mostly out of the way, there was only one more to go.

Grace's late husband had guilted her into trying anal sex for him. She didn't recount the details, but I can just hear his pathetic argument as he was pressing his hard, dry, dick against her puckered hole. And when the searing pain shot up her spine from being penetrated with hardly a warning, she understandably freaked out. I accidentally sat back onto a protruding railroad spike when my buddies and I were fucking around on the tracks in high school. I about shot into orbit when the nasty thing bumped my hole. I almost beat the shit out of Derek for laughing his ass off about it. Anyway, I have a healthy respect for that sort of sensitivity.

But it doesn't have to be that way. And if it hurts, then you're not doing it right.

I just needed to convince Grace of this.

I'd been toying with the idea of whether or not to initiate a discussion with her on the topic. This was one of those cases where it sounded like the right thing to do, but it didn't feel right. It's not that it was too awkward a subject for me to handle, and I thought she'd listen okay; it's just that I thought it might set us back quite a bit. She was making such beautiful progress as it was. So, I skipped fully disclosing my plans for the next step.

I'd brought up the topic of vibrators a few weeks earlier to see where she stood. She'd never owned one or used one in her life. It would've been hard to believe had I not already been aware of her limited sexual experiences, and been the one who introduced her to clitoral orgasms. Our short conversation went well; she was open to the idea of me using one on her. I pretty much knew she would be since I brought it up with my face planted between her open thighs.

What I failed to mention to her was what type of vibrator I wanted to use on her. Minor detail.

It was a Wednesday night of no particular significance. I'd had the vibrator in my possession for a couple of weeks, hidden in a drawer. Actually, I acquired several, but only one designed specifically for anal.

I'd bought a large frozen lasagna so I'd have leftovers for lunch. Baking it in the oven was going to take a couple of hours, which would give me plenty of time to play. I could've waited until a few hours after dinner, but the risk there was that she'd be somewhat tired and not quite as into it. As it turned out, my strategy worked.

Grace was shedding her work clothes by the time I finished placing the lasagna in the oven. She had a pair of shorts in her hand.

"Not so fast." I caught the wrist holding the shorts and pulled her to my chest. "We have some time before dinner."

I steadied her head and dipped my face to her neck, biting and sucking her flesh. I knew how sensitive her neck was, and how just one kiss could turn her mood in an instant. She swallowed hard against my lips and croaked, "What do you have in mind?"

"I want dessert first."

One thing about my girl was that she was turned on by dirty talk. Probably a product of being an erotic writer, herself.

"I've been craving my slut's pussy." She gasped and mewled. "All I could think about during work today was your sweet juice dripping down my chin as you came on my tongue. Your hot, delicious flesh all around my face, my nose buried in it until I'm drowning. Covered in your musky scent."

I slipped my hand down into her panties and curled my middle finger until it was sliding past her outer folds. She was already growing slick from my words. It always amazed me how fast that worked.

Grace widened her stance to allow my finger access without me asking for it. She was such a natural submissive.

I fingered her wet cunt for several seconds before withdrawing my hand from her panties. She whined and cut herself off quickly, knowing how much I hate whining. I chose to ignore it for the moment. Addressing it would cause a detour. I'll add it to her next punishment.

"I want to blindfold you." That was my way of asking for her consent.

Grace's eyes widened to saucers as she nodded.

"Take off your bra and panties."

I stood less than a foot from her as she slid her panties down her legs and stepped out of them at the same time she reached around her back to unclasp her bra. I could've done it, but she gets so worked up from me watching her undress. I look at it like it's hands-free foreplay.

I reached out and tugged at her right nipple until it became obscenely rigid. Then her left nipple. They were too perfect the way they protruded. I suggested she get them pierced when we first met, but I'd since changed my mind. They were perfect the way they were. I was starting to have some very bizarre fantasies about them that involved them being pristine.

"On your back. On the bed. Grab a hold of the headboard and wait for me."

She scurried off as I headed to the closet to change clothes. Blood circulation to my stiffening dick was being cut off by my tight jeans. I also wanted to go over the mantra in my head one more time.

A few days earlier, as I was working this plan out in my mind, I realized that I was going to need some serious willpower to stick to my plan. Once I inserted that vibrator in her ass and made her come, I was going to want to fuck her. That was fine, but in the heat of the moment, it would take everything I had to make myself remove that vibrator first.

I fucked a girl like that just one time. Feeling the vibrator through that thin membrane as you're fucking a wet cunt is like nothing else. It makes the cunt tighter, too.

Damn, but it's heaven.

I knew it was going to be even better with Grace. But, she wasn't ready for double penetration. If it turned out to be even the least bit uncomfortable, it would blow everything I'd worked for up until that point. It wasn't worth it. I'd rather wait. So, every day I was repeating this mantra in my head so my dick wouldn't make a decision I couldn't live with. Again. Face it buddy, it wouldn't be the first time your dick fucked up.

Once I got my clothes off, I decided to just stay that way. There was no point in getting another change of clothes dirty.

I immediately noticed Grace licking her lips as she saw me approaching. I did consider changing my course to fucking her pretty mouth first. That way I'd be unloaded as I completed my task. But the flow didn't appeal to me. I performed better when I was horny and I had a schedule to maintain. It was imperative that she climax with the vibrator in her ass. Before dinner. Stick to the plan.

As I was tying the blindfold, I couldn't help but notice all the signs of her arousal. The tiny points on her chest, her flushed cheeks and neck, her gooseflesh-lined skin. Her arms trembled as she gripped the iron bars of the headboard as if she were trying to break them. I took a moment to savor it all while she couldn't see my face.

Being the dominant in our relationship meant that I had to remain stoic most of the time. Calm and collected. In control. Sometimes when I was anything but, inside. With Grace, this was becoming so taxing.

I loved her. I was obsessed with her. The amount of possessiveness I felt for her was consuming at times. I'd spend entire chunks of my day devising the next thing I wanted to do to her. With her. For her. If she had an inkling of what I had planned, she'd probably freak out.

Just gazing at her lying there in total anticipation of my next touch, my next word, my lips and tongue on her skin, made me want to lose it. It was my own masochistic pleasure to torture myself like that. I could only do it while she was blindfolded because I knew the look on my face would scare her.

I made myself turn away from the bed and walk toward the chest of drawers where I had hidden the toy I needed. The restraint was a good exercise for me. For the addictive, obsessive part of my personality. And it always made me feel stronger. Better than any therapy money could buy.

I held up the orange device and mused. Why did they make it glow-in-the-dark? Is there a huge market for that particular feature? I shrugged and sauntered back to the bed, taking deep breaths as I did so. I was making a conscious effort to slow down while my dick urged me to hurry.

I pulled a hand towel and a tube of lubricant from the bottom drawer of the nightstand. I hadn't bothered to hide those things, Grace knew they were there. It wasn't as though I hadn't made it perfectly clear that I was going to take her ass someday. She knew that. I just didn't feel it was a good idea to apprise her of every step of the plan.

I lifted one of her legs to climb up onto the bed, and then pressed both her thighs up by her sides so she was folded in half. In the future, I'll just bind her legs like this. Once she gets used to being anally penetrated.

Her musky scent was strong. Dizzying, in fact. I held her thighs firmly in place and dipped my face to hover over her wet center. I blew along her wet folds and Grace released a cute, high-pitched moan in response.

I so love to tease her.

"Keep your knees up like this for me." I released her thighs and her legs stayed in position. "Good girl."

I needed my hands free to work with the lube and vibrator. I tucked the edge of the towel beneath her spine and placed the objects on top of it with my palm holding them in place as I lowered my face and extended my tongue to her slit.

She flinched with the first touch of my tongue. I languidly moved it in circles over the fleshy tissue, just getting her to relax. Her thighs parted more and her knees sunk deeper into the mattress next to her sides as her muscles released tension. That's it, baby. Relax.

I kept my tongue soft and slow as I circled her clitoral hood. Her tiny bulb was already peeking out like a turtle from its shell. She gasped as I circled it. It was still too sensitive for direct contact.

As my tongue worked her, heating her up, I unscrewed the cap of the tube and squeezed a bit onto my middle finger. She'd be used to this part by now, having made it a ritual.

When my finger pressed against her rosy bud, she automatically released the air in her lungs with a sigh. It helped the insertion a great deal. I hadn't instructed her to do it, it was just something she learned from our many sessions.

My finger slid inside without hesitation. Hot. Tight. I stiffened my tongue and swiped her clit directly to check her progress. She hardly flinched. The added anal penetration really helped get her going faster. Her clit was now almost fully distended.

I probed her ass with my finger as I continued to lick her pussy. I was careful not to concentrate my efforts too heavily on her clit just yet. I didn't want her to come before I'd had a chance to use the toy. After just a few more minutes, I felt she was ready.

I removed my finger from her anus and she sighed. It about made my heart explode with happiness. She wanted more. Someday I'd make her ask for it. And if I got my way, eventually she'd beg me to fuck her ass.

I squeezed a dollop of gel onto the end of the vibrator and used my finger to smear it around. The device wasn't very large; the head of it was maybe 1 1/4 inch in diameter, while the base was only an inch around. The length totaled 2 1/2 inches. It would feel slightly larger than my index finger going in, and then the shape and narrow base would allow her anal ring to nestle around the object comfortably.

There were literally hundreds of choices on the internet. From designs that gradually increased in size at the base, to beaded models, and eggs. I spent hours reading reviews before choosing this model of vibrator. I also picked out an assortment of dildos to use later. I can't wait to use that glass one.

I pressed the head of the vibrator to her hole and she exhaled again. Good girl. I swiftly pressed the head past her ring before she could realize it wasn't my finger and tense her muscles. It slid easier than I imagined it would and the whole process took less than two seconds.

Her breathing labored for a second and I picked up the cue. My tongue stiffened and began to work in earnest on her clit. When I heard a distinct change in her breathing again, more back to what I'd expect from her, I clicked on the vibrator.

"Oooooohhhh!" She yanked at the headboard and lifted her head from the pillow in surprise.

I gripped her thighs to keep her from straightening her legs and sucked her hard clit between my lips. Just as I had hoped, she climaxed. It was explosive, judging from her screams and the amount of thrashing she was doing.

I released her clit and held her in place so I could watch her hole contract with each wave. Sucking at the air like a fish out of water. My cock twitched its complaint and a fresh wave of adrenaline coursed through my veins. Fuck, yes.

I flicked off the device and eased it out before she'd finished her contractions. Then I was on her. In her. Fucking her with the newfound, adrenaline-riddled intensity of a teenager.

Grace screeched beneath me and for a second I had to search my memory to see if I'd remembered to remove the device. A second later she announced that she was coming again, and I realized that it didn't matter. She was alright. Better than alright.

And with that, I unloaded everything I had.

***

I worked her with that vibrator for the next two weeks. It became almost a nightly routine. I graduated from licking her pussy while using it, to fingering her clit with it inserted, and onto fucking her with it without the vibrator on while making her come with my fingers. I made sure she finished each time.

Her entire demeanor on the topic was changing. I don't think she even realized how flirtatious she was becoming with her ass. She'd gotten so she would bend over at the waist to remove her pants and then wiggle her ass in my direction. If I didn't have a goal in mind, I'd take her over my knee for being such a shameless slut and teasing me like that. There were plenty of things I could do to that ass that wouldn't exactly be pleasant for her.

I'd been starting to pay attention more closely to her bodily functions. Her cycle. She was fairly regular. There were routinely two times of the day when she released her bowels. Either one hour after dinner or in the morning before work. My go/no go decision would be solely based on whether or not she visited the bathroom after dinner.

Time to make the final preparations.

I slipped an ear syringe in the shopping cart at the grocery store, along with a mild soap designed for genital cleansing. Then a pack of condoms. I caught her curious expression, but couldn't tell if she figured out the usage for them or not. If she asked, I was prepared to talk about it. If she didn't, I knew that it was because she figured out what it all would be used for and had no further questions. She was a naturally inquisitive person and rarely left questions unanswered.

We went to bed that night with the items prominently displayed on the bathroom counter and no questions asked.

I had everything ready to set us up for success. Physically she was prepared to handle it. I had added a second finger to our play and worked her up to being finger-fucked pretty hard. And even though she routinely came, I kept my own expectations in check. There was a good chance that I would come from our first anal and she wouldn't. I had to be okay with that, despite my intense desire for her to finish. It was, after all, a big step. Then it dawned on me the one thing that I hadn't done to prepare her. I hadn't set her expectations. It was time to talk.

We rode to work together and stopped for dinner on the way home. At the restaurant, we talked about our day, what had happened at work, etc. We didn't go anywhere fancy, just a quick dinner and then home. When she was finished in the bathroom, I pulled her into my arms on the sofa, threw a blanket over us and muted the television.

"There's something I want to talk to you about."

She twisted around and looked up at me with an alarmed expression. "What's wrong?"

"Nothing's wrong. Relax, baby."

She sighed and half-smiled, not entirely sure of my intent.

"We've been sort of working toward doing something major and I want to know how you feel about it. I want to know what sort of expectations you have about it."

"Anal sex?"

"Yes. Anal sex."

Grace smiled and shrugged. A mild flush warmed her cheeks. "I've sort of been wondering when it's going to happen."