After-work quickie

Alex clenched his jaw as he drove home from work. It had been a frustrating day, and he wanted to be able to relax and get his mind off of it.

He turned the corner, onto his street, and his heart plummeted to his toes and skipped a beat when he saw his Owner’s car parked outside his house.

All thoughts of work were instantly far from his mind.

He knew what this was, he’d known it was coming, and he knew what would be expected of him.  Forcing his body to obey him, he pulled into the garage as his Owner got out of her car.

As expected, the passenger side door opened as well.  A strange man got out, and together, the two of them walked into the garage.

“Hello, slut,” his Owner said cheerfully.  His face flamed at the pet name, at her using it within earshot of someone else.  She was showing restraint, she always did when there were others around, but he knew her well enough to read the giddiness in her eyes.

“Hello, Mistress,” he replied quietly.  Her being giddy usually meant difficult and degrading things for him.

She approached him and hugged him tightly, and he could feel the excitement radiating off of her.

“My friend wants to use your mouth.  Let’s go inside.”

The casual, matter-of-fact way she said it was jarring in and of itself.  She could’ve been talking about what she had for lunch.

“I ate a club sandwich, and you’re going to eat a stranger’s cum.”

His heart was racing as he led the way into the house.  He was acutely aware of the unfamiliar presence behind him, walking beside his Owner, as they walked toward the door.

He fumbled with the keys.

“Having trouble, little girl?” she asked playfully, her hand on his lower back, sliding down and groping his ass.  “A little distracted?”

Somehow, he managed to get his door unlocked, and the three of them went inside.

He’d barely closed and locked the door before she was behind him, pushing him against it.  Quickly, she unfastened his pants and slid them down, exposing the women’s panties underneath.

“See?” she asked the man with her.  “I told you he wears them every day.  He’s such an obedient bitch.”

“His ass looks damn sexy,” the man replied.

“Doesn’t it?  It’s so perky.  Feel it.”

Alex lowered his head, his face hot with embarrassment, as he felt unfamiliar hands on him, roaming across his body, sliding underneath his panties, dipping between his legs.

But then, his Owner grabbed him by the arm and turned him around.

“Get on your knees, slut,” she ordered.

Wordlessly, he knelt down, cringing as he heard the unmistakable sound of a pants zipper.  He kept his eyes down, not wanting to look at what was in front of him.

He should’ve known better.  “Look at it,” his Owner said, lifting his head up.  “Look at what’s going in your mouth.”

Reluctantly, he forced his eyes up, his stomach tying itself in knots when he saw the hard, dripping cock only inches from his face.

He felt his Owner’s lips on his ear as she crouched behind him, firmly holding his wrists behind his back.

“Open your mouth, little girl,” she murmured.  “He’s going to fuck it.  And when he cums, you will not swallow until I say you can.”

His body almost seemed to act on its own, obeying her command as the cock was pushed into his mouth.

The man wasn’t gentle.  But then, Alex hadn’t expected him to be.  He held Alex’s head with both hands, thrusting deep and hard into his mouth.  Even when Alex gagged, he didn’t stop.  And his Owner kept a tight grip on his hands, keeping him from struggling.

Thankfully, the man didn’t last long.  His thrusts became more frenzied, his grunts more animalistic, until he plunged his cock into Alex’s mouth, as deep as it would go, moaning as his cock pumped Alex’s mouth full of cum.

Alex wanted nothing more than to be allowed to swallow, but obediently waited, hoping she’d be merciful and wouldn’t make him wait long.

“How does it taste?” she asked.  She moved closer, whispering into his ear, only loud enough for him to hear.  “You’re a cum dumpster,” she told him, the softness and gentleness of her tone a stark contrast to the words she said.  “Nothing but a pair of holes for real men to fuck.  Get used to the taste of cum, little girl.  This is the first of many.”

Her hands roamed across his chest, pulling him back against her.  “Swallow,” she commanded.

Relieved, he obeyed her, shutting his eyes tight as he forced his body to comply.

“That’s my girl,” she whispered approvingly.  She held him against her a moment longer, her arms wrapped around him, then suddenly released him and pushed him hard.  He fell forward, onto his hands and knees, as she rose to her feet.

“Come on, let’s go,” she said to her companion.

And they left, without another word to him.

Past the point of no return

You have come here
In pursuit of your deepest urge
In pursuit of that wish which till now has been silent…
Silent…

I have brought you
That our passions may fuse and merge
In your mind you’ve already succumbed to me
Dropped all defenses, completely succumbed to me
Now you are here with me, no second thoughts
You’ve decided…
Decided…

Past the point of no return
No backward glances
The games we’ve played till now are at an end
Past all thought of if or when
No use resisting
Abandon thought and let the dream descend
What raging fire shall flood the soul?
What rich desire unlocks its door?
What sweet seduction lies before us
Past the point of no return
The final threshold?
What warm, unspoken secrets will we learn
Beyond the point of no return?

M’kay, so my geek was showing there for a second.  But there’s not a whole hell of a lot out there more fitting right now.  Andrew Lloyd Webber knows his shit.

Tonight was fun.  Like, seriously fun.  Like, a million different kinds of fun.

Like, whoa.

So there’s this adorable sissy I own.  And earlier this week, I’d decided that he was going to take a big step forward today.

He was going to suck cock.  No big deal, there.  He’s done it before.  But this time, he was going to finish, and swallow.

Not a huge difference, right?

Heh, heh…

Poor Sounder.  It was a rough week for him.  Yesterday and today were the worst, of course.  I really turned up the fear factor, and gave him quite a bit to think about.

Oh!  And on… Thursday, I think?  While he was at work, he asked, “Did you ship something to me?”

“No, why?”

“I got a delivery notification.  I’m not expecting anything.”

Well, cool.  I didn’t think anything else of it, until later that night, when I asked what had been delivered.

His response was, “Yeah, God or whoever’s in charge definitely likes you more than me.”

I laughed.  “Why do you say that?  What was in the box?”

“Lingerie I ordered 6 months ago, and it never showed up.”

Ooooh, really?

I was intrigued.  Particularly when he was hopeful that it wouldn’t fit.

But, because the entire Universe works tirelessly to accommodate me, I received a text a few minutes later, after he’d tried it on.

“Of course it fits.”

“Is it pretty?”

He didn’t answer with words, but his answer was more than enough.

2017-05-07_23.27.53

Holy shit.

Like, ho-ly shit.

Um, yeah, it’s fucking pretty.

So yay!  He had amazing new lingerie to wear while he swallows cum.  And damn, that is some fucking hot lingerie.

I was even more excited.  I couldn’t wait for Sunday to get here.

So today, Kazander and I pulled up to Sounder’s house and knocked on the door.  He let us in, and I think my whole face lit up when I saw him, dressed up, his hair and makeup done, wearing one of my very favorite pairs of his panties, a pair with no back.

Actually, there’s a picture of him wearing that pair on his blog, along with some other incredibly sexy pictures.  And of course, I have it right here.

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I love these panties on him.  So pretty.

Dude, he was just so damn hot.  I didn’t wait, I barely dropped my purse and my bag on the floor before putting my hands on him, pushing him against the door and groping him.

I turned to Kazander.  “I love these panties on her.  They make her ass look so perky, don’t they?”

“Yeah, they do.  She’s fucking hot.”

And I just have to go on a quick tangent.  Because, while Kazander and I aren’t really “there” sexually with each other, he has become a really kind of amazing partner when it comes to Topping others.

I mean, he’s inexperienced as fuck, of course.  He struggles to find that balance between pushing limits and crossing lines.  As we were talking about how we wanted the night to go, I had to hold him back more than once, and remind him that if we break our toy, we won’t be able to play with her anymore.

But it’s awesome, it really is.  It’s so much better to have to hold someone back than it would be to try and encourage someone who just isn’t into it.

So I was excited, and turned on by how Dominant Kazander was through the whole thing, and how easily he fell into that role.  The two of us, sharing and using Sounder together, is pretty damn amazing, actually.

And Sounder really is such a fun toy to play with.  He was so nervous.  I’d been fucking with his head for days, and I wasn’t gentle.

I wasn’t gentle today, either.  I had him bend over the arm of the couch, his ass exposed and waiting.  Of course we were going to put things in it.

But I was nice, I went with something small (instead of the largest toy I have, which Kazander had wanted to use).  Kazander stood next to me as I eased the vibe into Sounder.

And once it was in, I asked Kazander if we wanted to do the honors.  He said, “Of course,” and took the vibe, fucking Sounder with it.

I stepped to Sounder’s side, putting one hand on the back of his neck and the other on the small of his back, really driving home the fact that it wasn’t my hand fucking him.

Poor Sounder, he was so tense, trying so hard not to enjoy Kazander fucking him.  And for a few minutes, he succeeded.  But then, Kazander and I could hear his soft, occasional moans.

It was so much fun, it was so hot watching Kazander fucking him with the vibe, and watching Sounder enjoy it.

Kazander wanted to fuck him with more than the vibe, though.  He tried pretty hard to convince me to let him fuck Sounder right then and there.  And for half a second, I considered it.

But no, that’s the next step.  I wanted Sounder to taste cum for the first time.  I wanted him to actively make Kazander cum, feel him shoot his load, and consciously swallow it.

Being fucked will, in many ways, be harder for him to handle than sucking cock, but there’s a level of passivity there.  All he’ll have to do is bend over and stay still.  Hell, I could tie him down, even, and take away his choice in the matter.

The end result would still be the same, no matter which hole we used.  Sounder would have a man shoot his load into him.  He’d officially be my sissy cumdumpster.

But with a blowjob, he has to be the one to do it.  He has to make himself my sissy cumdumpster.  He has to make the conscious decision to obey me, to do this thing he really doesn’t want to do, to make me happy.

Sure I could tie him down and let men use him.  And I will.

But not the first time.  Not tonight.  Tonight was going to be all him.

We went upstairs, and I happily showed Kazander the beautiful, pink, lacy sissy bed that Sounder sleeps in.  And then Kazander sat down on that bed, took off his pants, and waited expectantly while I told Sounder to get on his knees.

I pushed Sounder forward, holding Kazander’s half-hard cock and sliding it into Sounder’s warm, wet mouth.  I didn’t even have to push hard, or tell Sounder to open his mouth, like I have in the past.  Sucking cock is starting to come easier to him, I think.

He’s a very good cocksucker.  Kazander didn’t last long.  He came, his cock throbbing as he shot his load into Sounder’s mouth.

And Sounder, the obedient, darling slut, didn’t spill a drop.  I watched him, Kazander’s cock still in his mouth, forcing himself to swallow.  The look on his face was just absolutely precious.

Afterward, Kazander put on his clothes and went out for a cigarette, while I stayed there with Sounder, him on all fours on the floor.

“You’re a cumdumpster now,” I told him, my hand between his legs, rubbing his p-spot.  “And you’re going to cum with the taste of his cum still in your mouth.”

He didn’t take long, either.  I let him up, told him he could change, and that I’d meet him downstairs.  Kazander was ready to leave (we’d taken separate cars because he wanted to get home quickly).

But before he left, I asked him what he thought of Sounder’s mouth.

“It was great.  She’s a talented cocksucker.”

And it was funny.  I said, “You know what we should’ve done?  I should’ve had you cum yesterday.  Or this morning.  So you’d last longer.”

He nodded.  “I was thinking the same thing,” he agreed.  “Oh well, now we know for next time.”

I grinned.  “Thinking about next time already?”

He shrugged.  “I’m never going to turn down a blowjob from a hot slut.”

He left, and Sounder came downstairs, and he and I settled on the couch to watch a movie.  I sat there, my arm around him and my hand around his neck, and he started pushing forward against my hand, wanting me to choke him harder.

At one point, he even took my hand, pressing it harder against his throat.

And for the record, it really doesn’t take much to make me go from normal to turned-the-fuck-on.  Like, not much at all.  Sometimes, all it takes is a hand on mine, and an unspoken request to be handled more roughly.

My hand went between his legs, rubbing his p-spot again.  He spread his legs, leaning back against me, squirming and moaning as I rubbed him to an orgasm.  And then another.  I didn’t stop, I didn’t give him time to rest, I just kept going.

With my other hand, I fondled his breasts, but when I finally pinched his nipple, and heard him gasp, “Yes, please yes,” I intensified everything.  Combining the pleasure and pain, it didn’t take long for him to cum again, pushing hard against me and crying out, still writhing uncontrollably.

I’d never seen him that turned on before.  The way he moved was different, his voice was different, his mannerisms were different.  And it made him bolder.  At one point, he slid off the couch, kneeling at my feet.

“May I?” he asked.

“Of course.”

He bent down, kissing my feet while I ran my fingers up and down his back.  But, while I certainly enjoyed that, I wasn’t done making him cum, and pulled him back up on the couch with me.

I actually lost track of how many times he came.  It was definitely more than five, and it might have been more than ten.  And holy hell, they were intense.  It was so damn hot to watch. His back arched, practically screaming, clinging to me, his legs thrashing as the sensations overwhelmed him.

And I still wasn’t done.  I got off the couch, lying him down flat as I sat beside him, still rubbing his p-spot with one hand, the other around his neck, and now I could choke him even harder.

He came again, one last time, arching his back so high, I was worried he might hurt himself.  But he didn’t, he lied limp on the couch, panting and gasping, still squirming just a little.

“Are you alright?” I asked, grinning.

“I don’t know… I can’t handle it.”

I laughed.  “That’s a good thing.”

I got up to wash my hands.  After a moment, he managed to pull himself to his feet.  I walked up to him, and he wrapped his arms around me.

“That… That was… Just mind-blowing,” he murmured.  “Earth-shattering.”

“I can see that.  Was it enough to make up for earlier?”

“That part actually wasn’t as hard as I thought it would be.”

“Well good, see?  You’re a true born sissy.  It all just comes naturally to you.”

Any other time, he, being that perfect mix of sweet and sarcastic, would’ve had a sarcastic answer to that.  But this time, he barely managed a half-muttered “uh, huh,” before pulling me close again and resting his head on my shoulder.

But he seemed really unsteady on his feet.  “Come on, let’s sit back down.”

We sat back down, I pulled him close and put my arm around him, and he rested his head on my shoulder.  And really, in less than two minutes, I realized he’d fallen asleep.  The poor thing, so worn out, so overwhelmed.

I sat back, resting my head against his, letting him rest while I watched the end of the movie.  Then, I woke him up, and he walked me out.

I think he’ll sleep well tonight.

And when he wakes up in the morning, in his sissy bed, he’ll remember exactly what it felt like to kneel at the edge of it, obediently swallowing cum.  And he’ll know that there’s no coming back from that.  For the rest of his life, he will never not be a sissy cum dumpster.

Past the point of no return
No going back now
Our passion play has now at last begun
Past all thought of right or wrong
One final question
How long should we two wait before we’re one?
When will the blood begin to race
The sleeping bud bursts into bloom?
When will the flames at last consume us?

Past the point of no return
The final threshold
The bridge is crossed, so stand and watch it burn
We’ve passed the point of no return

Being sick

Isn’t enough to keep an eager cockwhore from being an eager cockwhore.  As I found out the other night.

I’ve been fighting the biggest bitch of a cold that last couple of weeks.  I haven’t felt up to playing at all.

But it had been too long since I’d seen my sissy, and Sounder has been suffering from the same cold.  After a couple of weeks of trying to stay as far from other people as possible, the idea of spending time with him, cuddling, enjoying each other in all our sickly glory, sounded amazing.

I didn’t even bring my toy bag with me.  Neither of us were up for a session.  But watching TV on the couch with a glass of wine was absolutely within the realm of our capabilities.  And for once, I didn’t have to worry about quarantining myself from all human contact.

I got to his house, walked in, and gave him a hug.  He was dressed in boy mode, but when I reached around, I felt the bra band across his back.

Which made me immediately smile.  Even sick, he still thinks of me.

He poured my wine, gave me my Christmas gifts (which became the inspiration for my new absolute favorite insult, “four-day-old tampon slime.” God, I fucking love this chick), and we sat down to watch a show we both love.

I wrapped my arm around him and pulled him close, running my other hand across his chest.  It seems like only a moment passed before my fingers went, almost of their own accord, to the buttons on his shirt.  Once they were undone, I couldn’t help but grope him under his bra (I mean, I’m sick, infirm, and weak.  Of course I couldn’t resist such an attractive temptation), teasing his nipples to little buds, then pinching and twisting them until the pain made him wince.

The way he moves…. you guys have no idea how hot it is, the way he moves.

Next came the button and zipper of his pants, and I reached in, fondling his clit and grinning to find that Tammi Lynn was already wide awake, bursting out of his pretty, lacy panties.

Funny enough, suddenly I found myself feeling quite a bit better.  I rubbed his P-spot, biting his neck and ear, whispering to him about the way it’ll feel when a man first pushes his cock into Sounder’s tight, pink pussy.

“You’ll try not to like it,” I told him as he squirmed and writhed and gasped underneath me.  “You’ll try to keep yourself from loving it.  But it’ll feel so good, having him deep inside you, pounding his cock into you.  You won’t be able to stop yourself, you’re too much of a whore.  You’ll want it.  You’ll push back against him, begging him to go deeper.  Faster.”

I put fingertips of my other hand against his lips.  “And when you feel that second cock push its way into your mouth, all you’ll be able to do is suck it hungrily, wanting it to fill you up just like the other one is filling you up.”

He gasped, parting his lips, and I shoved my fingers in his mouth, forcing them down his throat while I massaged him, while I watched him get closer and closer to the edge.

“You’re going to cum with a cock in each hole,” I whispered.  “You’re going to cum hard and often, and every time you do, it’ll just make you want them deeper inside you.  Come on, show me how much you want that cock in your mouth.  That’s a good girl.  Show me how eagerly you’ll suck it.”

He didn’t disappoint. Writhing on the couch, one hand between his legs and the other fucking his mouth, whimpering and sucking, his hands balled into fists, he came to the thought of being spitroasted by men, his illness, for the moment, forgotten.

I couldn’t help but laugh.  “Being sick isn’t enough to keep such a greedy sissy down,” I said, giving him a moment to recover before rubbing him to another orgasm. Or three.

Sure, we watched TV.  And it felt good, especially as achey and cold as I’ve been, to feel his warm weight against me like that.  It felt especially good to see how easy it is to wake up the slut in him, even when the rest of his body just isn’t feeling it.

My slutty, pathetic, adorable, hungry sissy.

And part 2

For years, forced bi was a hard limit for Kazander.

Then the idea of cuckolding was introduced.  And at first, it was never thought of as something we’d actually do.  It was just something we talked about for fun.  With that in mind, Kazander felt more comfortable getting into the fantasy of it when we were playing.

Humiliation is his biggest kink, so humiliating him by telling him that I’d never let his cock enter me again, that I would find a real man to fuck me, and make him watch, became one of his favorite things.

Eventually that escalated to me humiliating him by telling him I wanted to make him suck cock, and then to humiliating him by telling him that I would make him get fucked by a man, to know what it feels like to be fucked by a real man.

But of course, we both knew that this was just fantasy.  Hard limits and all.  I don’t fuck with those.

But what he didn’t realize at the time was that, by talking about it in the “heat of the moment,” to turn him on, I was actually conditioning him to actually want it.

Now again, this was a hard limit, so I didn’t initiate that.  That was his choice, he was the one who told me he was comfortable with it.  I, being the sweet, innocent, obliging person that I am, took that and ran with it.

As I am occasionally wont to do.

Fast forward…. Oh I dunno… 4-ish years, maybe?

Forced bi became a soft limit.  Something he was willing to do for me, but reluctant as fuck about it.  That’s the way he was the first time Sounder sucked his dick.  He was really almost at a freak-out level leading up to that, and it took every bit of the control and influence I have over him to keep him calm-ish.

But he discovered that night that maybe he didn’t hate it as much as he thought he would.  Oh, he still didn’t like it, that’s for fucking sure, but he realized it wasn’t really worth the anxiety he felt leading up to it, and sure, he’d be willing to do it again.

I’m serious, y’all.  It is exhausting being right all the time.

So good, that’s something I can work with.  And ever since then, I’ve been subtly working on him, training and conditioning him to becoming a man who would not only be eager to have his dick sucked by Sounder, but would take on a Top-ish role with him, and help me humiliate him.

Basic behavioral modification.  Super easy stuff.  Something I learned working with autistic kids, and it works just as well on grown men.  Kazander never even knew I was doing it.

So this time, there would be no reluctance, no hesitation, he would be perfectly willing to grab Sounder by his hair and force his cock into his mouth.  He even had a couple ideas of his own to humiliate him.

And in that respect, he’s actually meaner than I am.  Like, I had to hold him back on a couple things, to ensure we wouldn’t give Sounder a heart attack.

Fast forward to this past weekend.  After spending the first part of the afternoon feminizing Sounder, I was ready for Kazander to arrive and do his part.

Kazander got there, and we spent a few minutes chatting.  I asked him what he thought of Sounder’s appearance, and he said, “Very pretty.  Turn her around, I want to see her ass.”

Which, of course, I was delighted to do.  I turned Sounder around and pulled his dress up, exposing his black, lacy panties.  And then of course, I told Sounder to turn back around so Kazander could see the front.

It was an awesome night.  We went into the bedroom, and I pushed Sounder to his knees and stuffed Kazander’s cock in his mouth.  Both Kazander and I humiliated him while he sucked, and I got some lovely pictures and a great video.

And I feel it’s important to point out the fact that Sounder was rock hard and dripping during that.

But as hot as that was (and dude, it was fucking hot), the absolute hottest part of the night actually happened before.

I wanted to sit on the couch.  We all sat down, with Kazander and Sounder on either side of me.

For a moment, Kazander and I just talked about how feminine and pretty Sounder was, and when I mentioned Sounder’s growing breasts, he didn’t hesitate at all in reaching across me to grab one.

Then, Kazander turned to Sounder and said, “I want to see you in something sexy.  Go take off the dress and put on some lingerie.”

Sounder got up and asked me which he should wear (he has a collection of sexy, feminine lingerie).  I told him to surprise us, and he turned to obey.  When he came back, he was wearing a sexy, lacy little number that I love seeing on him.

Which was awesome, because it matched his panties.

I told him I wanted him to lie across Kazander’s and my laps.  We adjusted our position, and then he did as he was told, with his head on Kazander’s side, and his feet on mine.  I pulled his panties down, moved my leg so he couldn’t brace his weight on his knees, and spread his ass, exposing that tight little hole I love abusing.

“Look at her pussy,” I said.

“Looks nice and tight,” Kazander said, grabbing a handful of Sounder’s ass.

“It is,” I replied, getting a finger wet and pushing it inside him.  He gasped and moaned softly as I fingered him.  It was so hot.  “You should feel,” I told Kazander.

The only hesitation in him that night came at that moment, when I told him to put a finger in Sounder.  But all it took was a smile from me and a hand over his, and I guided his finger where I wanted it.

And then Kazander was fingering Sounder’s ass.  And really, once he got it in, the hesitation disappeared again, and he was right back to where I wanted him to be.  We started comparing Sounder’s ass to his girlfriend’s, wondering which would be tighter.  I pulled Sounder’s cock out from under him and started teasing it.

He looked so cute, sprawled across our laps like that, half naked, with his panties around his ankles and a man’s finger inside him. And Kazander was so damn hot, getting into his role with enthusiasm and being every bit as mean and degrading to Sounder as I was.

That was the hottest part of an incredibly hot day, and I cannot wait to do it again.

For sale?

So I received this particular gem about a month ago.

Jen.
Good evening. I’ve been an avid follower of your blog for some time. The dynamics you create with the men who serve you is something I find fascinating.
I am particularly intrigued by the path you’re leading Sounder down, and what you’re doing with him. That dynamic is fascinating, and I enjoy reading about it, and the things you do to him. I understand that he’s never been penetrated by a man. If you don’t mind, I’d like to ask your indulgence while I illustrate a fantasy I thought I’d never have the opportunity to fulfill.
I have always craved power and control over others. That craving, I’m sure, has had quite a lot to do with the level of success I’ve achieved in my life. But there’s something about sexual control that appeals to me on a completely different level. The idea of forcing someone to bend to my will is highly erotic. This idea has morphed over the years into a fantasy involving nonconsensual sex, of overpowering someone or rendering someone completely helpless and having my way with him. I am not homosexual, but for reasons beyond my understanding, this fantasy has always involved forcing myself on a man, rather than a woman.
You’ve said that Sounder has never been penetrated by a man, and is reluctant to make that happen. The post he wrote very clearly illustrates his general mindset, and the way his reluctance and fear drive you to lead him deeper. Being in a position of leadership myself, this is something I can appreciate. So there is something I’d like to propose to you.
I would like the opportunity to purchase his virginity from you, and use him to fulfill my fantasy. I will be staying in town for the rest of the week. There is a specific way I’ve envisioned this, but of course he is your sub and it’s open to negotiation.
I would like having him brought to my room, blindfolded, with his hands tied behind his back, fully clothed. I would like to forcefully remove his clothes, so he would need a second outfit to wear. And of course you’re welcome to be present through the whole thing. I know you value him and want to make sure your property isn’t harmed. To that extent, I also have recent medical records I am willing to show before I touch him, to prove that I am drug and disease free.
Once his clothes have been removed, I will proceed to penetrate him. You’ve said a couple times that he is very strong, so it’s unlikely I will be able to overpower him without him being bound. Hence the reason for having his hands tied behind his back. But that’s not to say I wouldn’t want him to struggle at all. A large part of what draws me to this fantasy is the aspect of penetrating a man against his will. Souder will be welcome to struggle just as he would if this wasn’t a controlled, planned event.
I don’t have much interest in his mouth. If you want him gagged that’s fine, although I would prefer him not to be gagged, and able to say whatever he wishes.
I  a businessman, and I of course would never expect something for nothing. I would be willing to pay you for the use of your sub, and for his virginity. I’m willing to pay $250 for it, up front of course. And after I’ve finished with him, I will leave the room for a time, to allow you to help him recover, and take your time in leaving. I’m unfamiliar with the protocols for aftercare, but understand that it’s important and should not be neglected, particularly after intense sessions like the one I’ve described.
Please respond at your convenience if this is something that interests you. I would like to thank you for your time and consideration, and wish you a pleasant evening.
Regards

The idea was an intriguing one, but I told him no and didn’t give it much thought.

Until yesterday, when it came up in conversation with Sounder.  I told him the gist of what this gentleman had been looking for.

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Well I think it would be fun…

Those of you who were clients of mine in Alabama can definitely understand why that price was so insulting.  I charged $200 for a session.  Just a regular, plain session.  Why would anyone think I’d give up something far more valuable for only fifty dollars more?

I told this man that I wouldn’t even consider something like that for so little, and that I was shocked at his nerve in suggesting it.  Sounder’s virginity for $250?  Are you kidding me?

That’s like asking to buy the Mona Lisa for a few thousand dollars (it’s worth almost 800 million, in case you were wondering… I kinda have a thing for da Vinci).  You’d be laughed out of the country for suggesting something so ridiculous.

And really, Sounder’s virginity is a valuable commodity.  He’s never been penetrated by a man, he doesn’t want to be penetrated by a man, but his desire to please and obey me overrides his reluctance.

I can see how that would give a man with a rape fantasy a unique opportunity to fulfill a fantasy he would not otherwise be able to fulfill.  Sounder is about as close to “unwilling” as you can get without crossing the line into actual nonconsensual sex.  It’s about as close to realism as you can get without breaking any laws or violating any moral code.

I get that.  As a lover of consensual nonconsent, I adore situations where a boy is forced to do things he doesn’t want to do.  I have my own rape fantasies, and my favorite porn videos involve (believable) roleplay rape scenarios.

So I get it.  I understand the appeal.  And, for this gentleman, I can even tell him why he wants to force himself on a man, rather than a woman.

It has nothing to do with your sexuality.  It’s a dominance thing.  It’s an alpha-male thing.  Especially for someone who craves control and power, what more effective display of power is there?

Gay, straight, or in between, it doesn’t matter.  The attraction to this kind of fantasy has nothing to do with sexuality.  It has to do with dominating another man.  It’s the ultimate display of dominance.

I’ve known a couple of straight or straight-ish Doms who owned male slaves.  When I first met a man like that, I didn’t understand it at all.  Why would he own someone he’s not sexually attracted to?  Why, if he’s not gay or bi, would he choose to own men, rather than women?

He explained the dominance, and the way he views D/s.  For him, he would never dream of Dominating a woman.  In fact, he was married to a Domme, and while he was in no way her sub, she more or less ran things.

For him, it was an alpha-male thing.  He explained that there was no greater feeling in the world than forcing himself inside a reluctant man, making that man accept him.  He was brutal with his subs, and regularly fucked them raw, ruthlessly held them and just pounded his cock into their mouths, he often went ass to mouth, he completely and utterly violated them and degraded them.

It was fucking awesome.  And it made me extremely jealous that I don’t have a penis.  Even now, imagining Sounder being brutally violated that way by a man makes me jealous I don’t have one, and can’t do it myself.

Oh, but don’t get me wrong.  Watching him being used like that by another man will be indescribably hot.

So I get it.  I know that attraction, I can relate to that attraction.  I can understand the appeal of a man like Sounder and the unique opportunity he represents.

But $250?  For Sounder’s virginity?  Hell fucking no.

He has never had a man inside him.  Ever.  In his life.

The very first moment that a man pushes the tip of his cock into Sounder’s hole, that will be gone forever.  You’re only a virgin once.  Only one man on the planet is going to be able to take Sounder’s virginity.  And if I’m going to give it to a stranger, it damn sure won’t be for $250.

I have expensive tastes, ladies and gentlemen.  And I have a boy on the other side of the country who misses me.

There’s no way I would sell something as valuable as Sounder’s virginity for that little.  And it is valuable.  Once he loses it, it’s gone forever.  He will never again be able to say that he’s never been fucked by a man.  For the rest of his life.

But I do know that just because something is valuable doesn’t mean that it’s in high demand.  So I’m curious to know what the demand for a reluctant man’s virginity is.  Is that something many men would want?  Is it something they would pay for?

It’s definitely interesting to think about.  Very intriguing.

 

Sounder Speaks – A guest post written by the sissy

As Domina Jen said, “just a tiny little pill.”  Not only was this the title of the blog post I had feared was inevitable, but it was representative of how the past several months have gone.  Feminization was never something I had expected, nor was it something I even knew much about, but it started in this same “just a….” fashion and before I knew it I was popping a tiny little pill out on its corresponding day and swallowing it down with a daily vitamin.

“Just a pair of panties” turned into “no more men’s underwear,” while “just try this dress on” evolved into “with the exception of work, women’s clothes only.”  The well-timed texts of “sweet girl,” which seemed playful enough given the physiological impossibility of that truly applying, were soon replaced by the tiny little word of “sissy.”  The realization struck hard; there were no physiological barricades to that title actually applying.

Playful left the building on that infamous night She handed me that first pill.  All of the side effects, which She was kind enough to detail at great lengths, seemed to pale in comparison to the one vision of that small white pill between Her finger and thumb.  All of the tangible fears couldn’t hold a match to what the first pill represented.  Understandably that must sound illogical, but I knew once that bridge was crossed and pill #1 was dissolving in my stomach it would follow in the footsteps of every other step.

As I suspected, minutes after pill #2 began working its way through my system, the fear transitioned to something far more puzzling for someone who had not imagined feminization: “Shit, what if this doesn’t work?”  You see, I don’t like failing at anything, and when you add the additional layer of detecting the enthusiasm Domina Jen had for the process, I began hoping for the results to be even more significant than the details She had used to scare me.

As of this writing, twenty-four hours have passed since Domina Jen studied and prodded me until She confirmed what I had thought, that the pills actually are working.  It was a relief, but it was also a realization that all of the texts that had haunted my mind were going to come true in due time as well.  Then, of course, there was the task that leads us here; after realizing how easily flustered I became when She updated me as to how many people had read the tiny pill post, naturally the next step was to ask me to contribute to the blog as a follow up to the very post that had crushed my nerves just days ago.

No matter what I have prepared for in my head, Domina Jen has a keen ability to take a difficult situation and morph it into something far more unfathomable.  For those of you who have been regular readers to this blog you know of Her requirement that Her perspective boys partake in a bisexual activity.  Now, it is not my “thing,” but I have engaged in it before so I wasn’t all that intimidated by it.  Sensing that, She made the declaration that my particular action would involve the additional layer of doing so while dressed as a sissy.

The buildup to that moment was a level of fear that my body had never encountered before.  Of course, detecting this, She was kind enough to regularly check in to let me know just how many hours I had remaining until it happened.  I’m a very self-aware person and I could feel the trembles, and I was fully aware that I was grasping for and fumbling over words as She applied the makeup to me.  None of that compared to the moment She left me standing alone in the room as She went to retrieve Kazander.  As I stood there staring at the ground listening to every step outside the room my head felt like it was a reflection in a magnifying glass while my stomach was enduring an extreme, never-ending descent on a roller coaster.  Right up until the moment She pressed his cock into my mouth , and I realized it was no longer about me.  That was what She wanted, and knowing She was not going to allow me off easy drove me to meet Her challenge and deliver what She wanted to the best of my ability.

So She continues to increase the pitch on the face of each mountain She leads me up, only to watch me step off the cliff once my mind reaches the plateau.  As She has mentioned, Her next desire is to up the wager on the bisexual action to full-on being fucked; well, truth be told, Her preferred picture to paint for me is being fucked by 4-5 men during one time.  Some of you can probably understand the terror in hearing the cliff notes version of conversations She has as She actively recruits the 4-5 men.  She has me so paranoid of the event that I literally pace in front of my windows waiting to catch a glimpse of Her car pulling up the driveway, hoping to see only one head in the car.

There is an important distinction between stepping off a cliff and being pushed.  None of this has been against my will; this isn’t 1492 after all.  We have crossed lines that I didn’t know I had, simply because I never imagined these lines ever being in front of me.  As has been alluded to here, I’ve been dealing with a perfect storm of health issues that have minimized my ability to withstand the type of kink my world had been centered on.  Although some more “balanced” people would disagree, by opening the door to this new world, Domina Jen has actually done an amazing thing for me.  She gave me something to embrace and dedicate myself to, that injuries really do not preclude my fullest participation.

That is not to say that it hasn’t turned my mind inside out, and that I don’t lie awake at night staring at the ceiling, fearing what could come next.  But isn’t that one of the great facets of having a kinky lifestyle?  I have a Pavlovian response to the text message indicator on my phone, men’s underwear seems foreign, the porn I watch would make my former self blush and turn away. 

So one little pill has evolved into 15, a cock in the mouth is no longer good enough, shopping for men’s clothes is pretty much off limits, and “sissy” no longer stings.  The fears will continue to increase with each “ohhhh you know what….” text and I’ll continue to have the same approach to visiting this site as someone would while opening a pressurized can of Anthrax an inch away from their face.  But that is the path, and this is my role, and far be it from me to take it lightly.

 

The Adventures of Bi Guy and Sissy Slut

For years, we had the same conversation, over and over and over and over again.

“I’m not bi.  It’s going to make me freak out.”

“You’re not going to freak out.  You’ll be fine.”

“Maybe I will, and maybe I won’t.  I admit that part of it turns me on, but I’m not bi.  I don’t know how I’ll react to something like that.”

I know how you’ll react.  You’re going to enjoy it a lot more than you think you will.”

“You might be right, but you might not be.  I might have a major freakout.  I just won’t know until it happens.  And if I cum, it’ll be even worse.”

“Then you won’t cum the first time.  You’ll be fine.”

“How can you possibly know that?  What makes you so sure?”

“Because I know you.”

I can’t count how many times we’ve had this conversation.  When we first met, forced bi was a hard limit for Kazander.  Over the years, it went from being something that completely disgusted him to something that was humiliating enough that he found the fantasy hot, but the idea of actually doing it was still not even close to being up for discussion.

Then, shortly around the time we started looking at cuckolding as a real option, and something that we felt we could go through with, the idea of forced bi came up again.

He was hesitant, and reluctant as hell, and we spent hours and hours and hours talking about it, but it finally officially moved off his hard limit list and became a soft limit.

It took another year to make it actually happen.  Part of that is because he doesn’t usually have the typical Sagittarius rush-into-decisions, risk-taking trait, but the Capricorn slow-and-steady, analyze-every-damn-thing-before-making-a-move trait.

And, completely off-topic, but when you factor in the Sag’s fear of commitment with the Cap’s need to take decisions involving commitment painfully slowly, you start to understand why I lost patience and bought him a ring and proposed to him after four damn years.  I’m an Aquarius, after all.  Arguably the least patient sign of the zodiac, depending on who you ask, and notorious for making broad, sweeping, life-changing, can’t-go-back decisions at the drop of a hat (and yes, I’ve done that repeatedly.  And I’ll probably do it again, which I’m sure my Capricorn boys will just love).  I don’t do slow.

So that was part of the problem.  And he was very concerned (justifiably so) about making sure he was in the right headspace for something like that.  I understand that.  It’s a big wall to climb.  It’s not something that was easy for him to do.

But the reluctance was the biggest part of the reason why it was so hot to me.  I mean, don’t get me wrong.  Watching two bi or gay guys together is hot, and I’m way more into BDSM porn between two bi or gay men than I am into BDSM porn with two bi or gay women.

But it’s the reluctance, the forced part of “forced bi” that I love.  I love making a man do something he doesn’t want to do (and the topic of consensual nonconsent begs a post of its own).  Making a straight man do something with another straight man is not just sexy to me because it’s two guys, but because neither of them really want to do it.  It’s the ultimate rush of power for me.

Because I can tie a man down and do plenty of things that he doesn’t want done.  I can take his choice away, take away his ability to stop me, and that’s all well and good (and extremely hot, in its own right).  But with forced bi, there has to be action.  He has to actively submit, to choose to obey me, to choose to do something he really, really doesn’t want to do.

Which, for a straight man, makes it all the more humiliating.

So when I met Sounder, who listed himself as bi, that’s immediately where my mind went.  Then, I discovered that he’s not exactly bi, in that he’s not attracted to men and has zero interest in doing anything with men.  But his previous Mistress made him suck her boyfriend’s dick, and while he certainly didn’t want to do it, he did it to please her.  To obey her.

And he immediately had my complete attention.

So, not only did he have experience with forced bi, and knows he won’t react badly to it, but he’s reluctant as hell, genuinely doesn’t want to do it, and would be completely humiliated by it.

Perfect.

So I arranged for Kazander and me to go over to Sounder’s house, and Sounder would suck cock while dressed as a sissy, and Kazander would have his first real bi experience.

They were both nervous, but alcohol and small-talk took at least a little bit of the edge off.  And then I took Sounder upstairs to get him dressed.  Really, he makes such a pretty girl.

He was already wearing the panties and the stockings, as usual.  So I had him get the new lingerie he’d purchased (without being told to, by the way) and put it on.

And holy shit, y’all.  He looks fucking sexy in it.  I mean, he showed me a picture of him wearing it when it first arrived, and he looked damn good in the picture.  But the picture didn’t do him justice.

Next came the wig.  And I couldn’t help myself.  He was right there, in the room, dressed like that, and looking sexy as hell.  I reached into his panties and rubbed his hole with one hand, while teasing his cock with the other.

“You’re going to be a sissy cocksucker,” I told him.  “There’s no going back from that.”

He was rock-hard.

Once he was dressed, I took him into the bathroom to put his makeup on.  I only did the basic stuff.  I was in a hurry to bring Kazander into the room, to make him get a blowjob from a man (well, sort of a man).  I’d been wanting this for years.

Finally, Sounder was as ready as he was going to be, and I went down to get Kazander.  He came into the room, where Sounder stood, waiting, dressed in wig, lingerie, and makeup, and looked at me.

I could tell he was nervous.

It was adorable.

I told him to take his pants off.

He obeyed, reluctantly.  Slowly.  But finally, he was ready.  I pushed Sounder to his knees and told Kazander to sit at the edge of the bed.

As reluctant as Kazander was, Sounder was really reluctant.  Kazander’s had years of me working on him, preparing him for it.  Sure, Sounder had done it before, but never as a sissy, and it wasn’t all that high on his list of things he wanted to do, anyway.

I pushed him close to Kazander, and grabbed Kazander’s cock.  He was about to get his first blowjob in years, but he wasn’t hard.  Yet.

I knew a nice, warm, wet mouth would change that pretty quickly.  After all, at the end of the day, a man’s mouth feels exactly the same as a woman’s.

For a moment, I held Sounder there, between Kazander’s legs, rubbing Kazander’s cock across his face, drawing that moment out for a bit.  Because once I put Kazander’s cock in Sounder’s mouth, there would be no going back from that.  Kazander will have gotten a blowjob from a man, he would have taken pleasure, gotten hard, and been turned on by a man.  And Sounder will have taken his first major step toward being a full-on sissy.

Sounder was so reluctant.  He kept his eyes shut tight, his lips pressed firmly together, and I had to push him closer and closer to Kazander’s cock.

Finally, I told him to open his mouth.  Slowly, hesitantly, he obeyed, and I pushed Kazander’s cock into it.  They both sort of cringed at that moment.

It was adorable.

It didn’t take long for Kazander to start getting hard, and I pushed Sounder down on his cock until he gagged.  Then I pushed him down on it again.  And again.

Once he started dry-heaving, I let him catch his breath for a moment before urging him back between Kazander’s legs and letting him continue sucking.  That’s when I turned my attention to Kazander.

He was lying down, and I lied beside him, one hand on Sounder’s head, urging him to take it deeper, and started kissing and nibbling Kazander’s neck and ear, reminding him that he was getting his dick sucked by a guy, and he was liking it.

It was hugely, amazingly, unbelievably hot.

And when Kazander sat up and put his own hand on Sounder’s head, pushing him down, I thought I would cum all over the floor.  At one point, he even ran his fingers over Sounder’s back.  And mentioned that Sounder has a cute ass (and it’s good that he thinks that, since he’ll be inside it sometime down the line).

So someone is quite a bit more bi than they thought they were….

Hey, look at that, I was right.

Which is awesome.  Back when Sissy was around, we’d talked about the possibility of him subbing to both Kazander and me.  Which I had never thought was an option, until Kazander seemed quite interested in the idea.

And that opened up a whole new world of possibilities.  If he was willing to try Domming a boy with me, there were a million places we could go with that.

But it never happened with Sissy, and the mood passed, and Kazander lost interest in the idea.

So it’s definitely good to know that it’s an option again.  I think it’ll take some time for him to really get comfortable with the idea.  Alcohol played kind of a big part in how quickly he warmed up to it.  Sober, he might feel differently.  But it’s certainly more of a possibility now than it was two days ago.  That’s hugely exciting.  I think it could be a lot of fun to dominate someone with him.  It would be a pretty awesome bonding experience for the two of us.

And I was right about Sounder, too.  The entire day, he was a mess, worried about what he was going to have to do.  Although, as reluctant as he was to actually suck on a penis, it was more the significance of the act, and what it meant, that messed him up.  He was going to be seen dressed as a girl, on all fours between a man’s legs, a true sissy cocksucker.  It made everything we’d talked about feel more real.

Not that he doubted me before.  But it’s one thing to talk about how I’m going to turn him into a cocksucking whore, and another thing to actually do it.  Until now, it had just been harmless (he may not agree with my use of that word, but we’ll go with “harmless”) fantasizing and talking.  Actually being made to dress up in front of a man and take that first step was a whole different thing altogether.

But, as it turns out, it was surprisingly easy to be seen by another man while dressed up.  He had expected it to be rough, but it wasn’t.

And then, even the act of sucking Kazander’s dick was easier than he thought it would be.  Granted, he has done it before, but that doesn’t mean that he ever liked it, and it felt different this time, with the added element of the forced sissification.

But, as it turns out, he’s just a natural cocksucker.

What a surprise.

See this?  This is my surprised face.

So one is way more bi than he thought he was, and the other is way more of a natural sissy than he thought he was.

Double win for me.

Most of the pictures I took are just for me and my boys, not to be posted here.  But there is one I especially liked, and can share.

 

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They’re so cute together, aren’t they?