Category: Smut Page 2 of 5

Microfantasy Monday – Role Reversal

On December 14, 2009

On a happier note, here’s a MFM! Not as much a “reversal” as “exploration” but I think it falls under the general category, and it’s what I wanted to write, so there you go.

The idea behind Microfantasy Mondays comes from Ang of Sweltering Celt.

This week’s theme: role reversal.

Though we have talked about genderfuckery this is the first time I’ve expressed the more vulnerable side of me, the one I’m still working on figuring out my own self. I went all out with this one, which seemed like a good idea at first but as I waited at her door I couldn’t help but wondering if she would laugh at me. She didn’t.

The minute she saw me I could see the recognition in her gaze as she looked me over, supporting my gendered choices with a sweep of her gaze and a bite of her lower lip. I saw her take in my black slacks and crisp white shirt over a chest flatter than she had ever seen on me, and the fedora that covered the top of my bright red hair.

My still slightly nervous smile became more of a cocky grin when I saw the recognition quickly overcome by lust and I made my way into her apartment. I quickly pushed her against the wall and tangled my fingers into the soft auburn hair on either side of her head, taking her lips with my own and asserting myself against her. I could smell her, spicy with a hint of vanilla. I was already intoxicated by her and aching for more.

I pressed my pelvis against her so she could feel my cock, an unfamiliar bulge against her thigh. Knowing it was there made me want her lips around it. The silicone was feeling more like my flesh every moment as my excitement mounted. My lips moved to her neck my hand slipped under her skirt to find her cunt, no panties just as I had instructed. She mumbled something about having dinner all ready for us, but I had a different hunger to sate first.

The First Night: Getting Down To Business

By Tai Fenix Kulystin

On June 4, 2009

In a Love: Marla, Identity: Queer Intellisexual, Introspection, Polyamory, Smut

Found via The Alexa Collection.

“It’s business time
You know when I’m down to my socks it’s time for business
That’s why they’re called business socks ooh”
-“Business Time” – Flight of the Conchords

“There’s nothin’ wrong
With me lovin’ you
Baby, no, no
And givin’ yourself to me can never be wrong
If the love is true”
-Let’s Get It On
(which has a special place in our relationship, as Jack Black’s version of it is all of our ringtones for each other)

This is the fourth installment from my NYC/DC trip continued from The Beginning: New York City, The (Un)conference: Getting to D.C. & Sex 2.0, and The Meeting: Kissing At Red Lights.

There are many aspects of our first time that are a blur, but I remember playing with her breasts quite a bit, licking and sucking on her nipples and flicking them with my fingers.

I remember her bra and shirt being taken off, then going for her cunt beneath her jeans, at which point she protested that she couldn’t get completely naked before I had even taken off anything. I chuckled and told her that wasn’t going to happen, she tried to get her hand under my skirt, I pulled away and continued to molest her until I acquiesced and took off my shirt and bra then slipped out of my skirt as she took her pants off.

Most else after that is a big happy endorphin-rushed blur. I remember when I first slid my hand across her cunt lips, felt her wetness, found her clit beneath my fingers and sunk my fingers into her. I can still see the way she writhed, how her body arched and shook as she came from a stimulation so simple as a thumb on her clit and two fingers inside her.

What amazed me the most was how casual it all felt, how right, how perfect. Nothing felt forced or unnatural, fucking her came as easy to me as breathing, and I wanted to do it as often as I breathed. There was no time with her that I did not want to push her down and enter her, feel her coming beneath me as I kissed her or played with her nipples.

Once I had fucked her and made her come a few times, she excitedly rolled me over and got out her Pure Wand so she could introduce me to it. All I can say is: holy fuck. I knew I needed a Pure Wand but I didn’t know how much I NEEDED a Pure Wand. It was both hot and amusing because the six steel rings through my inner labia kept jingling against the steel of the Pure Wand and she either started singing Jingle Bells or just alluded to it. See what I mean about comfortable?

I was having a hard time coming, which often happens to me. This was extremely frustrating for us both. I have since postulated that the more aroused I am the more difficult it is for me to come, which seems counter-intuitive but somehow seems to also be true. I take not being able to come as simply a sign that I was way too aroused for my own body to handle.

My inability to come combined with my intense desire to fuck her and make her come at any given time ended up meaning that she didn’t fuck me as much as I fucked her. I didn’t mind as much as she did, though, because I was mostly frustrated at my body and much preferred to spend my time exploring hers. This wasn’t really fair to her but I have promised she will have the chance to make it up to me this coming weekend.

Once we fucked sufficiently and were coming down we called Onyx immediately to see how he was doing and check in. He mentioned he wasn’t sure if he would be able to handle hearing us on the phone with each other, but there was much talking, many professions of love, and many Facebook games played (we are all addicted to Mafia Wars and My Zoo and couldn’t resist playing them during breaks in fucking).

We both had our Big Foot storage bags with us and we dumped them out on the bed, effectively covering half the bed with sex toys! While we didn’t use all of them we certainly got a lot of mileage out of most of them.

As Marla said in her post, “while time seemed to stop, my stomach did not,” once we could tear ourselves away from both fucking and talking with Onyx long enough to figure out what we wanted to eat it was already past 11 and most places were closed for delivery. Room service was out of the question due to expense so we ended up ordering a pizza, the only thing we could find so late for delivery, and after burning up many calories the best way possible and having not eaten since noon for me and earlier for her it was possibly the most delicious pizza I have had in quite some time.

We talked with Onyx again after pizza and got super tired, deciding that sleep was in order. We snuggled, eskimo kissed (which I do a lot and love to do), caressed, and eventually I started rubbing her cunt again until she came. I just couldn’t take my hands off of her!

At some point the blindfold came out and she instructed me to lay back because we were going to play a game: Guess That Dildo! It was quite fun, actually, though I still couldn’t come. She fucked me with dildo after dildo while she rubbed my clit, I rubbed my clit, I used Gigi on my clit, and while I was feeling it and definitely aroused it just didn’t happen. Needless to say we were both disappointed and frustrated.

The game did lead to me exclaiming “my cunt reads dildos like braille!” Which I was highly amused at saying, as I guessed every toy correctly except for Ella simply because I forgot that she had brought Ella with her. I think I fucked her again at this point, because if I wasn’t able to come at least one of us should, dammit! After that we turned off the lights, snuggled up, and joked and eskimo kissed our way to sleep.

Just as she said in her post, because I can’t think of a better way to say it: “Waking up next to her the next morning was the closest thing to perfection I have ever felt. Sunday is another post, for another day.”

Last Friday

By Tai Fenix Kulystin

On April 30, 2009

In Identity: Top, Introspection, Sex Blogging, Smut

So many things have been happening in the last week, and I don’t think I will have the time to write about them all individually even though I want to. Since I’ve been bogging you down with worrysome and insecure poly-related posts I’m going to start with an experience outside of the triad: last Friday, when Kyle and Coy Pink came to visit (though this is mostly about Kyle).

Back at the beginning of March Kyle drove up not too far to Seattle to meet us for the first time. He wrote about it here, I failed to write about it even though I had the intention to. I don’t remember why I didn’t write about it, I think I may have been experiencing mad writers block at the time or something, who knows, though his re-counting of the evening is pretty flawless so you should go over and read that first.

Then, Kyle decided to head up here last Friday. When we got together in March CoyPink was unable to make it as she had prior plans and I, like a dolt, had forgotten to ask her to come until a few hours before Kyle was supposed to show up. I’m good like that. Anyway, this time CoyPink was able to come, though not until a little after Kyle was going to arrive. No big deal, we were excited she could join us, though she ended up missing most of the night’s excitement! Not that what happened after she arrived wasn’t exciting, but there was no beating involved… but I’m getting ahead of myself.

Kyle has written about this visit as well, with far more detail to leading up to occurrences than I will probably give, so you should go over and read his post on last Friday, it’s pretty long, but I’ll be here when you get back. Go on. I’ll wait. Honest.

Did you read it? No? What are you waiting for? Seriously.

Well, if you read it you read it, if not you’re missing out. Anyway. Roxy (who, for those of you who don’t know is Kyle’s long-distance love) contacted me on twitter before he arrived and asked if I would be willing to give his package a squeeze and tell him it was from her. I responded that I would not mind doing so in the least, while trying to appear willing but not overly eager. Kyle is a great guy, but I don’t know him that well, so I was a little awkward and kept trying to think of ways to do it in a somewhat subtle manner, of course Roxy didn’t need it to be subtle.

She also informed me that he may be instructed to kneel at our door when first arriving, but didn’t know how evil she was going to be yet. I knew from that it would be a very interesting evening, but I figured Kyle would have to do a few somewhat embarrassing things at her request to begin with, and then we would all just do our thing. I didn’t expect any play or really anything to go beyond a few simple instructions to get a little redness in his cheeks. I was a little wrong.

Kyle ended up arriving late. He let me know he was going to be late beforehand, and I wasn’t surprised (from his tweets I thought he left later than ideal to be right on time, not to mention parking around our apartment is a bitch), though Roxy decided to use that as a reason for his first instruction. He was to ask to kiss our feet to make up for the offense of being late.

I wouldn’t deny him his ability to perform for his Love, so I offered him my bare feet to kiss, and took a couple pictures while he was doing so for him to send to Roxy. He did the same for Onyx, though he donned his boots for Kyle to kiss. When Kyle was done I walked over, slipped my arm around him, and squeezed his packy through his jeans informing him that he wasn’t the only one who Roxy had requested something from and that the squeeze was from Roxy. He seemed a little flustered, which was lovely, and I thought that would be the end of that.

I was putting the last touches on dinner and we all were chatting when she included further instruction, for him to ask us how to further make up being late. Onyx was far more comfortable requesting things at this point than I, as I could put myself more easily in Kyle’s shoes and was trying to figure out the balance between good embarrassing this very new friend of ours and what might be crossing the line. I overanalyze, we all know this by now.

Kyle offered to help serve dinner, Onyx agreed, and so Kyle went about fixing a plate for him and presenting it to him, which Onyx made him do over again with enthusiasm and excitement. I felt badly, as I’ve had to do the same in the past and it’s always really annoying.

We ate, and chatted, and again I thought that was going to be the end of it. Both Onyx and I had remarked to Roxy that Kyle was being very good and fulfilling his duties. I admit I was a bit hesitant, and still am, about commenting too much/too little and I think I ended up on the too little side. In addition to all this, I was also texting with Marla and I knew she was feeling excluded and alone, so I was trying to manage everything all at once which ended up in me being a little more distant perhaps in everything than I meant.

We were having seconds when the next instruction came, “please do offer your ass and beg for a spanking.” I was somewhat surprised, as was Kyle I think, though apparently Onyx wasn’t. Onyx informed Roxy of Kyle’s reaction to the instruction: groaning and tossing his phone on the floor!

Onyx decided that since I rarely get to get out my beating desires, as he is not into pain or me beating him at all, I should be the one to fulfill this instruction. I decided to finish my seconds and send a text to Marla regarding what was going to happen (which I found out later didn’t send) and so Kyle was instructed to kneel on the floor until he was needed.

I was thinking about the best way to do everything, and decided getting out my Liberator Ramp would be a great idea to position Kyle on. It pretty much doesn’t enable the bottom to drop their ass, and means I can get at all the good spots all the time, so I figured it would be a good idea. Onyx got the ramp, Kyle got positioned, and I pulled out most of my impact play toys.

From Kyle’s post: “At first it was kind of weird, I mean, we’ve only hung out once before and now my ass was in the air waiting to be beat. But Scarlet is very good and we got into our rhythm pretty quickly.” I agree, it was a little strange, but once we got into it I think we both had a really good time, as evidenced by the pictures that we took and the happy post-beating stupor that Kyle ended up being in. Kyle and Roxy have praised me multiple times on my beating technique, apparently Kyle has raved about it to her and promised to show it to her when next they meet, so I must not be too bad, right!?

I used just about all of my impact play toys, with the exception of the rose crop and the black rubber whip, you can see the implements below:

From L to R: Black Suede Flogger, Black Rubber Whip, Rose Crop, Cheetah Fur-Lined Paddle, Rabbit Fur and Leather Flogger, Bark and Bite Paddle, Small Red Acrylic Cane, Large Red Acrylic Cane, Wide-Tipped Riding Bat.

There are a lot of great pictures of the beating, but I think this one is my favorite of the ones Kyle posted:

I had a lot of fun, and I know Kyle, Roxy, and Onyx did too. It was a great experience that I’ll also be happy to repeat should the opportunity present itself. I didn’t really see it as sexual, but I put play with friends in a separate category than play with lovers, and separate out the sex from bdsm, because they’re not completely entwined just mostly. I do feel like I’ve seemed distant with both Kyle and Roxy when they’ve tried to engage me and I blame it on my general social awkwardness rather than anything else.

Not long after the beating was over CoyPink arrived with brownies. We all settled down, chatted for a while about various things including me whipping out a bunch of my sex toys because I do quite love talking about them and I really don’t get that much opportunity too, hopefully it didn’t seem like I was bragging or showing off too much, haha.

After not too long we all headed out to the bars, we went to one which was just too loud and a little too crowded. We decided it would be best to go to one where we could actually hear each other and engage in conversation. We all talked about our relationships and poly and all sorts of other things, and we all drank and generally had a great time.

Kyle and CoyPink are rapidly becoming good friends, especially CoyPink who I have been able to see more often (as makes sense, more time together = more familiarity/comfortability/etc.). We should be seeing them both again this Saturday, too, for the Seattle Erotic Art Festival, though I doubt any beatings will occur this time.

Tendency to Tease

By Tai Fenix Kulystin

On April 24, 2009

In a Love: Onyx, Smut

From art-or-porn via img2.voissa.com

I’ve always enjoyed teasing, in many ways it’s a display of power. The ability to work someone up over something, get them desiring whatever it is I’m offering, and then taking it away, usually with the intention of offering it again. That push-and-pull, back-and-forth testing of how far you can go before tipping the other person over the edge is simply delicious.

It’s all about manipulation, but with me it’s manipulation with the end goal of pleasure for both parties instead of anything else negative. Sometimes it’s just gentle coaxing, but the other night I definitely had a distinct goal in mind.

I hadn’t really teased Onyx in quite some time, and I’m not sure what came over me. We were lying in bed and I wanted him to fuck me. I started stroking him, teasing him slightly, and he told me he was tired and that if I wanted to be fucked I would have to get on top. While I’m not opposed to riding him by any means, that wasn’t what I wanted at that moment, I wanted to be taken.

I pouted, protested, and continued stroking for a bit before stopping. I gave a heavy faux-sigh and said that was fine, we just wouldn’t play at all. I had made sure that he was already hard at this point, in the state where he needed me to continue almost as much as he needed to sleep. He acquiesced, we lay there a few minutes more, and then I began stroking him again.

He groaned and arched into my fingers, his cock swelling even harder beneath my knowledgeable fingers. I stopped stroking and played my fingertips along the underside of his cock, pressing against the area right under the head where it meets the shaft. Then I stopped all together.

His hand reached for his cock but I batted it away, stopping him from stroking himself now that he was hard and aching for more. I tsk’d and told him that he was tired and needed to sleep. His other arm was beneath me as I had been cuddled up against him when we started. I effectively kept him from touching himself while I used my other hand to tease his tender flesh.

My movements were quick and deliberate, making sure to bring him up to a fevered pitch before stopping and letting him stay there, squirming and needy, but unable to do anything about it. I juxtaposed those movements with slow soft caresses which drove him mad, just lightly touching his hard throbbing flesh, sliding my fingers across sensitive skin. He fought me, but not too hard. He can easily overpower me when he chooses, but he was loving the exquisite anguish I was producing as much as I was.

We continued like this for quite some time, until the teasing was too much to bear and he growled, slipping from my grasp, grabbing me and moving behind me. He slid into me easily as I had grown wet through my own teasing of both of us. From behind he grabbed my hair as he savagely thrust into my needy cunt, giving me exactly what I had been desiring.

He fucked me hard, quickly, and it wasn’t long before he was coming inside of me, both of us grunting and growling our pleasure into the otherwise silent room. We stayed like that, locked together with me on my knees, both breathing heavily as I focused on the muscles of my cunt, squeezing around his softening cock as we both slowly thrust to keep ourselves connected.

He slipped out of me and settled down next to me, both of us happily fucked and contented for the most part. His hand found my now very wet opening and began to thrust, touching me just the right way as my fingers moved to caress my clit.

Microfantasy Monday – Silence

By Tai Fenix Kulystin

On April 21, 2009

In Smut

The idea behind Microfantasy Mondays comes from Ang of Sweltering Celt.

This week’s theme: silence.

Technically I’m posting this on Tuesday, but I don’t care, hopefully you don’t either but if you do: too bad.

I parted her legs with the insistence of my hand and gave a few soft slaps to the soft mound that lay between them, hearing her gasp. My lips curled into a smile in the darkened theatre. We were the only ones in this row near the back, but there were many others in front of us that could easily hear anything above a whisper, depending on the scene on the screen.

One hand deftly unbuttoned and unzipped her pants, the only layer between my hand and her tender parts, giving another harder slap as a loud crash came through the speakers. She was squirming beside me, I could tell she was looking at me but I kept my gaze fixed forward, slipping my hand down and finding her clit with my fingers.

Slowly I began to rub, building up the intensity, just as the action on the screen lessened and the scene shifted to a heartfelt talk, one of the ones that wraps up what the big issue is. Leaning over I quietly hissed “Be sure you’re silent, little girl, you don’t want the other people knowing just how much of a slut you are, rubbing back against my hand in a crowded movie theatre.”

I heard her whimper as she trapped her lower lip between her teeth and gave me big eyes that showed her inner conflict. At that moment my fingers began rubbing faster, building her need to a higher level. The need to cry out to release the tension in her was almost unbearable but she would keep quiet. She knew the reward for keeping quiet would be far greater than the momentary satisfaction of moaning aloud.

Microfantasy Monday – Growth

By Tai Fenix Kulystin

On April 13, 2009

In a Love: Marla, Smut

The idea behind Microfantasy Mondays comes from Ang of Sweltering Celt.

This week’s theme: growth.

This is not so much fantasy, but it’s very micro.

A week ago we were nervous, unsure of what was okay to say and what was not. We had the same desires we do now but were keeping them quiet, letting the idea of them saturate our minds but only disclosing parts. Torturing ourselves and each other with uncertainty.

Each day we get more comfortable, share our words more easily, or desires flow from our lips and fingers as we despise being so far apart. Nearly three thousand miles away our thoughts still turn to the other even without yet having met face to face.

We dream and long for the time when fingers can be thrust into aching holes, wrapped around soft throats, and sucked on by eager mouths. When toys and fingers and mouths can be used to discover all the right places to make the other moan, writhe, and come. When nothing separates us but air, or not even that.

A week ago we had all these desires but weren’t sure how to express them. We didn’t have the permission yet from ourselves, or the coaxing from the other to explore how we fit together. Now we do.

Microfantasy Monday – Cards

By Tai Fenix Kulystin

On April 6, 2009

In Gender Galaxy, Smut

The idea behind Microfantasy Mondays comes from Ang of Sweltering Celt.

This week’s theme: cards.

We were still sitting across from each other when the last of the other players left the room. I watched as she slid one hand through her hair, bit down ever so gently on her lower lip, and shifted in her seat. One leg was crossed over the other before she leaned forward ever so slightly, the front of her dress gaping and giving me a healthy dose of cleavage as she stared at the five cards in her hand.

I moved to rest my right hand on the rim of my fedora, tracing it with my finger as I watched her, enjoying our costumes and our current privacy. We had decided that if we were going to sponsor a game night we should make it fun, encouraging everyone to dress up was her idea, but the three-piece suit and fedora had been mine knowing seeing me in it would make her weak in the knees.

Suddenly standing I moved to her in two fast strides and pulled her to her feet faster than she knew what was happening. I had waited until after our guests started arriving to let her see me in my outfit, and she had been casting smoldering glances in my direction all night. I requested she femme up tonight, wearing a dress I picked out for her, matching heels, thigh highs, and pearls. No panties.

I pressed my body against hers, turning her so her back was against the table, sweeping aside the cards and poker chips on it as I pressed her down onto her back, moving over her and slipping my thigh between her legs. I kissed her with all the passion and intensity the last few hours had built in me. Literally knocking her off her feet and onto the table.

My right hand moved under the hem of her dress and slowly slid it’s way up her thigh while the other moved to caress and pinch one of her nipples. Finally finding her between her legs I quickly pushed two fingers into her wet heat, pumping them in and out as I moved my mouth from hers for a moment to say “You’ve been wanting this all night, haven’t you?”

Microfantasy Monday – Morning

By Tai Fenix Kulystin

On March 23, 2009

In a Love: Onyx, Smut

The idea behind Microfantasy Mondays comes from Ang of Sweltering Celt.

This week’s theme: A perfect lazy morning.

Too-bright sunlight offends my eyes as I blink in the late morning light.

Letting out a soft groan I stretch and roll over onto my back reaching over to find his hand I clutch it to my chest before my head turns, gaze catching up a second later. I watch him for a few moments before rolling over yet again, this time putting his arm beneath my head and snuggling up into the crook of his arm the way I love to do.

Perfection is how we fit together.

A contented smile curls the corners of my mouth, looking up into his sleeping face as I move my lips just slightly to the left and sink my teeth lightly into his exposed nipple, trying to be gentle since he’s not as much of a fan of pain as I am.

As I watch him stir my hand slides down his side only to rest just above his cock, stroking there softly, teasingly, before moving to kiss him good morning.

Microfantasy Monday – Flame

By Tai Fenix Kulystin

On March 9, 2009

In Smut

The idea behind Microfantasy Mondays comes from Ang of Sweltering Celt.

This week’s theme: Flame.

“Touch it.” She giggles, nervous, but I persist. “Touch it.”

I watch her as she looks into my eyes, sees the seriousness there, realizing I’m not just teasing her. As she reaches her hand out toward it her tongue darts out to moisten her bottom lip, teeth right after it, tugging at the soft skin that I am aching to touch.

She smiles and glides her fingers through the flame once, knowing that the middle of the teardrop-shaped heat will not burn her fingers, only slightly hesitant because of that. Each movement of her hand is graceful, it seems to float up and around in fluid motions. I envy her hands.

I grin as she bites her lip again, her nervousness all the more adorable. She was the one who asked, who had been curious about trying it since she saw me doing it at the last play party, who had mentioned to me that she would like to try it some time that same night. She had tried to be nonchalant when she suggested it, too, but I could see the places her facade had cracked, showing the nervous girl behind it.

She has already taken off her top, my hand gestures for her to lay down and again she moves like a dancer, lying on her back so that I can have access to her abs and belly to roll my hot stick across. I take my torch, steeped in alcohol, and bring it to the teardrop fire her fingers were so recently caressing. In a burst of light the flame is transferred and I hear her gasp.

The Best Laid Plans

By Tai Fenix Kulystin

On March 6, 2009

In a Love: Onyx, Sex Blogging, Smut

Found at Romeo Tees (yes, it’s a shirt you can buy! I want one)

I love anal sex. I really don’t say that enough on here I think. I love giving it, receiving it, just about anything about it. Well, I don’t like when it’s messy, but I don’t get upset when it is because that’s part of it. Obviously when you’re playing with the backdoor there is always the possibility of shit, and while I’m not into that I just roll with it and always keep tissues handy. Wendy Blackheart actually has a wonderful post about shit and anal sex called shit happens on her awesome anal-sex oriented site Ask the Ass Bandit, but I digress.

Onyx feels much the same way as I do about anal sex. In a way it’s one of the things that brought us together, or at least was a big part of our relationship, as much of our online relationship was played out in an anal sex channel on irc.bondage.com. He’s actually quite an anal slut when the mood strikes, as I am. We both enjoy giving and receiving, which makes it that much more fun.

Despite both of us loving anal we don’t do it as often as we might want. It takes quite a bit of preparation and forethought, which we don’t usually have when we fuck. Usually it’s just an impulse when we do it and not planned out.

The last few nights we’ve been talking about me fucking his ass. Ever since I got Brando, really, we’ve been talking about it, though not talking about me fucking his ass with Brando because that prospect was a little too intimidating. Neither of us have the courage to take Brando anally yet, though I think it’ll happen sometime, but that’s another story.

Since we’d been talking about it for a while, last night while we were settling down to bed, Onyx brought it up again, and I told him to go get the required assistants, specifically one of my harnesses and whatever dildo he had a preference toward. He came back with Boy Butter, my Hardcore Harness, Bandito, Celestial Perfection, and Tantus G-Force Wand. The last one isn’t harness compatible, but is great for fucking with because of it’s extended handle.

I did a few things to clean up and then instructed him to get on the bed (futon). He knelt and then moved to all fours, moved a pillow under his chest to facilitate his position before letting his head fall to the bed, resting on his hands. As I watched I slipped the Celestial Perfection into my harness and then slipped the harness on. I wasn’t going to fuck his ass right away, I would first use my fingers to open him up, but I wanted to be ready to fuck when we got there.

My Rubber Whip was lying on the floor in front of him, so I instructed him to hand it to me. I lightly began slapping his ass with the whip, trailing the soft falls across his back, and lightly teasing his balls with the strands. He’s not big into pain, and though the whip can sting if used hard, I was being sure to be light, using the sensation play to heighten his excitement.

I lubed up his ass and my finger with the Boy Butter and began working it in and out, slowly and surely, as he moaned and writhed before me. I added a second finger, then a third, adding little bits of lube each time a new finger was inserted. I remarked on how much of an anal slut he was being, and occasionally stroked his cock or massaged his balls. Whenever he started to tense I made him squeeze his ass around my fingers and then release completely.

When I added a fourth finger he tensed and pulled forward so my fingers pulled out, letting me know that had hurt. I worked back up from one again and added more lube before adding the fourth finger, but was able to get all four in easily that time, and he liked it. He was pushing back against the fingers as I moved them in and out. I asked him how many fingers he thought I had in.

“Three?” He asked curiously.

“Nope. Four.”

“Wow.”

I grinned and moved them a little more intently in his ass, my other hand squirting a bit of the lube onto my cock as I did, getting ready to fuck him with the silicone that was now transformed into my pearly white cock.

I had already made sure the curve of the cock was going to be at the right angle to get at his prostate, so I started slowly inserting. He pulled forward suddenly, letting me know that it hurt for some reason. This also popped my cock out of my harness, which was annoying, the base is pretty thin and went right with him when he jerked his hips. I added more lube, tried again with the cock out of the harness, and again it hurt. We tried a third time, got farther in, but it just wasn’t working right.

We paused for a few moments and decided to try Bandito instead. I loosened the harness so I could slip Bandito in, during which time one of the straps came undone completely because I had pulled too hard (it has tighteners like the ones on backpacks to make the shoulder straps longer/shorter) and I had to take it off and lace it back the right way before putting it back on again.

While I was doing that, Onyx remarked that perhaps the position was the issue, and decided to move onto his back instead. I went and grabbed my sling which helps the bottom keep their legs in the air more easily so that he would be more comfortable in that position.

I again started with my fingers while stroking the lube into my Bandito with my other hand, getting him back to the point of being open for my cock before going to insert it. It hurt again. We decided that maybe he hadn’t cleared his backdoor completely, though he had gone before we started to try and avoid this problem, so he went into the bathroom to do this.

He came out a bit later, claiming something wasn’t quite right, and we should maybe wait for another time. I’ve had the same experience before, having anal be unexpectedly painful and just not feel right, so I understood. We cleaned up, snuggled a bit, and ended the night with me getting fucked doggy style instead, though not in the ass.

Even when you’re thoughtful and ready for anal, sometimes it just doesn’t work for whatever reason. We will try again, though, soon, and next time it’ll work. Or so we hope.