Today is the day

I've never taken a boy's ass with a strap-on.

Seriously.

I've come close. Real close. I had the head of my big purple cock inside babyboy's very tight ass. One thrust of my hips and I wouldn't be writing about this cherry of mine. But I was using the harness and dildo a former girlfriend and I had purchased together. We had selected a length and size we'd both enjoy vaginally. I never thought for a moment I'd use its ample length and girth on an ass let alone a male ass.

The truth is I don't feel compelled to play with every ass I come in contact with. And although I maintain a theory that every male is an ass slut or an ass slut ready to happen, I haven't played with many trained for regular ass play.

They all have tight little pseudo virgin asses. None could have taken the girth of my purple cock.

I have enjoyed watching a few of them suck it, pushing my big purple cock deep into their throats.

And then I broke the harness on the girl. *sigh* Good times.

The purple dildo remained in my toy bag and occasionally made appearances in play such as when I tied my sub to a table and forced him to suck it, then masturbated with it before I forced him to suck it some more.

*sigh* Good times.

Could I have bought another harness and a more reasonable sized cock and fucked a boy's ass before now? Sure. But the truth is I have enjoyed the anticipation of taking a boy's ass for the first time.

Perhaps I've nearly romanticized it. I've waited so long and I want it to be with the right guy at the right time.

I can't even type that without giggling at the ridiculousness of that idea but it's probably true. I've been "saving myself."

And today is the day.

From submissive to boyfriend. Can a D/s relationship survive?

While straddling the boy, I thrust the nipple of my right breast into the his mouth and leaned into him, smothering him with my double D’s. He sucked furiously and, as he began struggling and thrashing as his oxygen ran out, the thought running through my head was “MINE. MINE. MINE.”

As I ground my hips into his, “MINE. MINE. MINE,” was all I could think.

As I raped his mouth with my tongue, as I gripped his cock so hard he winced in pain, “MINE. MINE. MINE.”

Only he’s not mine.

He doesn’t greet me by kissing my hand anymore. He doesn’t call me Mistress. He doesn’t do a dozen little things anymore because he isn’t MINE.

But the primal part of me that enjoyed owning him doesn’t seem to know that. That part of me that screams MINE even now, more than three weeks after we ended our D/s relationship as we try to patch together something that somewhat resembles dating.

I’m not the only one having these same internal conflicts. My best friend, Miss Apryl recently broke up with her collared, 24/7 slave that she'd been with for 9 months and has experienced difficulty transitioning from D/s to dating. She had so much trouble with it that she no longer has any relationship with him, in fact.

“I was just thinking we might be able to date without D/s. That was fucking stupid. I can't go back. When I found out he was jerking off without permission I nearly lost my shit. And that was after he moved out,” Miss Apryl recently revealed. “Even before that I didn’t like that he was no longer sitting to pee and every time he plopped down on the sofa, I was SO irritated.”

While their D/s relationship was in effect, Miss Apryl’s slave was require to sit every time he urinated and had to ask permission to sit on her furniture. These little rituals, like me requiring my sub to always greet me by kissing my hand, were small but meaningful reminders of their submission and indicators of their respect for us.

And we miss them.

I recognize that when non-D/s relationships evolve, it is not always without incident. This I know only too well as my friends with benefits relationship with my FMT evolves into a friendship that’s more emotionally intimate yet devoid of the yummy benefits I’ve enjoyed so much over the past two years. I’m struggling with the transition and that’s probably another blog altogether.

But I feel like the battle to turn a D/s relationship into a dating relationship is probably a lot different. Miss Apryl hypothesizes that this is probably because of the ownership element of D/s and as I reflect upon the feelings of MINE MINE MINE I’m having in regards to my former sub, I tend to agree.

"Trying to date after D/s feels like the relationship is going backwards," Miss Apryl said. "And when you have that level of commitment, you can never go back."

Moving in and moving on

I recently moved in with my FMT. I'm renting his guest room. We're not LIVING TOGETHER.

It's a temporary thing. It works for now. It helps us both out.

We're still friends with benefits, my FMT and me. In fact, I think we've increased the friendship factor.

But the fact of the matter is, I'm living with a guy I have a history with, one that I have enjoyed fucking.

This didn't go over well with my sub.

I've never made a secret of being polyamorous. My sub knew it when he contacted me and knew that I've been seeing other guys since we've met.

So a week ago I was surprised when he admitted to feelings of raging jealousy and then verbally attacked me and my lifestyle choices.

The short version of our break up is this: he can't handle me being polyamorous.

Somewhere along the way, he'd fallen in love with me. It wasn't planned. It just happened. And he'd dealt with his insecurities and kept his jealousy under control until I moved in with my FMT. Then something in him snapped.

Somewhere along the way, I'd fallen for him too. How could I not? I enjoyed him in every way - kinky and vanilla. The play was phenomenal AND I loved spending time with him outside of the bedroom. He's smart and witty and I enjoyed his company as much as I craved his submission.  He was a guy I could almost picture building a life with.

Until he snapped.

He's not poly. He doesn't get it. He can't handle it.

It's unfortunate. It's tragic, really. I've waited so long to find a sub I connect with. One who could satisfy my needs, D/s and otherwise.

If he was a cuck, he'd be perfect.

We're at a stalemate, my (former) sub and I. He can't handle even the thought of me with other guys. I'm polyamorous.

I'm a glass is half full kind of girl so I have to admit it's probably for the best that if this was going to be an issue, it's good that it came up now. As sadistic as I am, I don't relish hurting someone emotionally and clearly I was doing that to my sub.

I just had no idea that by moving in, it meant that I'd be moving on.

Edging

For those of you who may not know, edging is bringing someone up to the point they're ready to cum but not letting them orgasm. If you've been reading my blog a while, you know it's one of my favorite ways to exert control.

Edging a guy has become somewhat second nature to me, even when that guy is not submissive. I did it with 9 and I do it with my FMT. Both enjoyed it. Only my FMT admits it easily though. It's probably because he's not all wound up in the Dom mind set.

My FMT is what I call pseudo vanilla. He's kinky by vanilla standards but not lifestyle D/s. That's not to say he doesn't understand the lifestyle though. He had a pretty fair grasp on the subject before we met almost two years ago and has picked up a few things just from being around me.

He "gets it" but enjoys joking like he does not. He tries, on occasion, to give me a taste of what I do to subs. "I want you to feel what it is that you do your poor subs." Yes, he considers himself some kind of advocate for all male subs as if it's his job to right all the wrongs against them. And it never fails to get a rise out of me. No one could ever say my FMT doesn't know precisely how to push my buttons.

Earlier this week we were enjoying the benefits of our friends with benefits relationship when he suddenly switched gears on me. This man who seems to live to see me orgasm suddenly stopped mid thrust just as I was about to cum.

Right at the edge.

"What the fuck?!?!"

"What?" he smiled as he started fucking me again.

"You just ..." I lost my train of thought as my orgasm immediately began to build again. I heard him moan a little and knew it was in response to me tightening around him. I was ready to cum.

And then he stopped.

"Oh my God. Really??? Seriously??" I playfully smacked his face.

"Really?? Really??" he mimicked, then snickered.

"You can't do that."

"Do what?"

"You can't just stop like that?"

"Like what?"

"You can't just stop fucking me like that!!"

He laughed. "Oh can't I? Why not?"

"Because you can't!!"

"Oh yeah? Isn't that what you call edging? Hmmm? Yeah?"

"Yes but ..."

"See? See what it's like?"

"No, I don't like it!"

"Well, that's what it's like when you do it to guys! It's not very much fun, is it? IS IT?"

At this point I'm laughing. Here is this vanilla guy, the biggest proponent of edging I've seen from a guy who doesn't submit, trying to "teach me a lesson" about how terrible edging is.

Here's the thing. I really did hate it.

Now like any woman, I enjoy a certain amount of teasing, during foreplay especially.

Teasing, yes. Edging, no.

Hell fucking no.

Making the List - Top 100 Sex Blogs of 2010

Friday night I was perusing twitter when I ran across a link from @writingdirty's Jack Stratton regarding the list for the Top 100 Sex Bloggers of 2010. Though I'd been thrilled to learn I was nominated, I'd actually forgotten about the list and was unaware of when the results would be posted.

So Friday night I was relaxing with my bestie, Miss Apryl, her slave and my sub when I read the news. I AM #30!!!

No, it wasn't like I got a call from the Academy or something. I wish I could say it was during something terribly sexy but it wasn't. Miss Apryl was making oatmeal cookies and the boys were watching TV.

All three of them got to see the Lilyana happy dance, we toasted with freshly baked oatmeal cookies and then the rest of the night all four of us worked into the conversation as often as possible reference to me being #30 on the Top 100 Sex Bloggers of 2010.

Yep, that's how I roll.

I tell you all, my readers, this story for a couple of reasons.

There was some outrage at who was named #1, Alexa DiCarlo. Do your own research if you're interested, but the short story is that it was revealed that Alexa was not the female sex worker she presented herself as. "Her" blog was removed from the web, in response to the accuations, I'd imagine.

As a sex blogger, I understand protecting your identity. We expose a lot of ourselves in our blog and we don't need someone stalking us. What we're doing isn't critical. We aren't curing cancer here, we're writing about sex. And we're doing out here on the interwebs where you can basically be whoever it is you want to be.

And if some guy named Pat wants to say his name is Alexa and that he's a call girl, hey, he can do that. For me personally, knowing that doesn't make me want to read "her" stuff but it probably doesn't diminish the hotness of "her" blog for others.

But let me tell you about Lilyana.

I am who I say I am. I'm a lifestyle Domme in my thirties who lives in Las Vegas. But there is more to me than just what you read. I reveal what I feel like needs to be revealed in order to tell a story effectively. You don't need to know what I do for a living or about my family life in order to read and appreciate what I do in my kinky life.

The boys I write about are real. I protect their identities as I protect my own, but they are very real.

My stories are all real. Whenever I write about a scene with a boy (or the girl), they read it and ALWAYS tell me that's how they remember it too. Yes, I could embellish for the sake of the hotness of the story, but quite honestly, it's just too much trouble. For me, the truth is more than hot enough.

Yes, I realize it would be so much hotter to say that I received a call from another hot sex blogger right in the middle of some amazing scene with a hot boy, but that's simply not what happened. I found out I'd made the list while the hottest thing happening was the oven baking some really delicious cookies. And I'm ok sharing that.

I am who I am and I write about what actually happens to me. If that makes me Listworthy, then I'm glad. It is fun for me to know you actually want to read about it.

On planning and satisfying cravings

In many areas of my life, I'm very much a planner. I like to schedule things. I like to know what I'm doing, what comes next.

But when it comes to playing with a submissive, my scenes are never planned in detail. I allow them to evolve naturally at my whim. I can be as sadistic as I am sensual and my mood very much dictates in what direction I steer a scene.

Sometimes, though, I'll want to do something that has logistical requirements. In the case of Forced bi with fireboytoy and pk, I had a finite period of time in which to execute the scene AND I needed to draft another person to assist. I can't just decide I want to force a boy to suck cock without having another cock around. It's got to be a planned thing.

Other times, I have a specific craving that simply must be satisfied.
 
Earlier this week, my sub and I had an opportunity to play. We've spent a lot of time together recently and have played quite a bit, but much has been impromptu. In other words, it's been mostly unplanned play that occurred no where near my toy bag, no where near my rope.
 
I've enjoyed every moment of this "stolen" time together, but there's something extra sexy about playing when you've been looking forward to it, anticipating it, even *gasp* planning for it.
 
My sub knows me well. He knows I don't like to plan details of a scene. He often teases me about it. But I did let him know I wanted to do rope. That I was craving it.
 
He'd arrived at our hotel suite before me and was happy to report that there was plenty of bondage friendly, sturdy furniture. Upon my arrival, I evaluated what I had to work with and settled on the big table like desk. My sub pulled it into the center of the room where I could have plenty of access to all sides of it, and him, once he was tied to it.
 
While he changed into a very humiliating pair of fru fru panties, I slowly unpacked my rope and other toys, pausing to consider my options and snickering at my own wickedness.
 
I tied a length of rope to each wrist to create cuffs I could use to tether him and then bent him face down over the desk, lenthwise, so that he was stretched across the smooth wood and almost on his toes. I tied each rope to a leg of the desk securely and then slowly circled my tethered prey. I giggled at the view of his ass, bent over the table with the ultra feminine thong, its ruffle around the waist almost a skirt, and heard his wince muffled against the wood of the desk.
 
Sliding my hand between his legs I found his cock hard from the humiliation of the panties and in anticipation of what was to come.
 
Or maybe it was my laugh. It seems that my laugh is his kryptonite. But that's probably a whole other blog.

I left him there while I retrieved a towel, lube and a butt plug.  I donned one rubber glove with a snap and pulled his pretty panties down.

"With your panties down around your knees like this, you reminded me of a naughty little girl about to get a spanking," I said as I applied lube to his asshole. He whimpered in response.

I played with his ass until he was gasping and then inserted a butt plug and pulled his panties back up to keep the butt plug in place. I continued to tease him, relishing every whimper, every moan, and then I switched gears.

From my toy bag I retrieved the fairly large purple dildo I used with my strap on until I broke the harness on the girl last spring. I used the flat base that acts as a suction cup on smooth surfaces to stick it to the desk in front of my sub's face but not before I'd smacked him in the face with it, taunting him with the length and girth.

"Suck it."

Tied across the desk with my big purple cock in his face, he looked up at me with big brown eyes, wincing in the way that makes me so so wet just before starting to lick it slowly. I watched him closely, holding the base as he teased my dildo with his mouth. Impatient with his prudishness, I grabbed the back of his head and forced it down on the dildo until his lips touched my hand. He gagged a little, making me even wetter, and I taunted him with talk about sucking real cock for me one day.

His whimpers, gagging, wincing and rapid breathing turned me on so much, I had to do something about it. I moved a comfortable chair directly behind him, yanked the dildo out of his mouth and made myself comfortable. With one leg draped over the arm of the chair I pushed the purpled dildo into my wetness easily not bothering the stifle the moan that errupted.

My sub tried to turn to see me as I described how good the big cock felt inside me but my ropes kept him virtually immobile. Watching him struggle to see me made me even more excited.

I propped one foot up on his ass but not before I used my toe to push the butt plug just a bit deeper in his ass. I laughed at the view - my foot on his obviously manly ass, butt plug clearly visible between his butt cheeks as he's bent over wearing pretty panties.

I knew how badly he wanted to watch me masturbate. We'd discussed it several times. I'd taunted him with it before, IMing him or texting him, teasing him with the knowledge that I was masturbating and he couldn't watch.

There we were in the same room and he still couldn't watch. And it was killing him.

Having him bent over for me, in rope, using him as a foot stool as I masturbated with a perfectly sized dildo turned me on too much. Though I savored every moment, he wasn't struggling to turn and see me long. I tried to put it off, to delay my orgasm, but I came pretty quickly.

I put the purple dildo, still wet with my juices, in front of his face and watched him clean it thoroughly and eagerly.

Yes, he was allowed to satisfy of his craving too. His craving to taste me.

Poly by permission

I’m poly. This is no secret to the boys I see, vanilla or kinky. It can’t be. It’s a part of who I am.

When I began seeing my sub almost two months ago, we discussed polyamory. He’d been a live-in submissive to a married Domme whose husband was a Dom and also had a live in sub, so he’d experienced poly. However, he’d never been allowed to see anyone but her, never experienced how it is to maintain multiple relationships himself.

As a Dominant, I realize I’m perfectly within my rights to ensure my sub doesn’t see anyone else while they are with me. What’s good for the goose doesn’t necessarily apply to the gander.

But I’m also fair.

Early in our relationship I let him know I’d be open to allowing him to date but that he’d need to ask first.

“So let me get this straight. You’re poly and I’m poly by permission.”

I laughed and said yes.

So yesterday the subject arose and he asked permission to date. He is seeing me date other guys and wants to experience polyamory himself.

My first instinct was to react with "MINE MINE MINE" like a child who has been asked to share her toys. I can't help it. But after a little discussion, my reasoning prevailed and I agreed. However, I advised him there would be parameters.

Of course he’s going to have rules.

1. You may spend no more than 30 minutes a day on dating websites corresponding with and screening potential dates.
2. An hour or less before any date, you must masturbate, cum and consume your cum. Unless you are in chastity at the time or doing a special assignment for me, assume you have permission to cum in this scenario so you don’t need to ask. However, you should text me and let me know you’ve done it.
3. No kissing on the first date.
4. You must wear panties on your first 3 dates.
5. Text or call me after each date. I don’t expect a report unless I ask but I want to know you’re home safe.
6. I own your orgasm. If you plan to have sex, you must ask permission.
7. Ensure she’s clean. ASK.
8. Use protection during sex.
9. You can’t take anyone on nicer dates than you take me.
10. You may not submit to anyone else.
11. She may not leave any visible marks on you.
12. You should keep me updated as things progress so that we can decide when it is appropriate for her to learn about your lifestyle and me.
13. I am your number one priority. I get first dibs on your time.

The idea of the rules isn't to make dating difficult for him, though reading over the rules one might assume that's the case.

Hey, if I'm going to share my toys, it's going to be on my terms.