A feminine sissy body

What’s sexier than a sissy slut?

Last time I was with Sounder, I noticed something while he was lying on his back, on his pink sissy bed, wearing his pretty lingerie.

He really is looking more and more feminine now that he’s been taking the birth control for awhile. His body looks softer, rounder, with more pronounced curves.

I can already see his tits under his clothes even when he’s wearing his boy costume. And it was so awesome when I realized that his boobs had gotten that big. We were out, having a couple of drinks after work, and he was wearing his normal professional work clothing.

At one point, he stretched in the chair, and I could plainly see the outline of his breasts under his shirt.

It was unbelievably hot.

Of course, that was a while ago, and his body has only gotten more feminine since then.

The most recent things I’ve noticed are his waist and hips. He really is developing a fucking sexy hourglass figure.  I love that I can see that subtle curve in his waist now.  And the longer he’s on the pills, the more pronounced those curves will become.

I mean, look at this picture.  If you didn’t know that this is a biological male, you’d totally look at this and assume it’s a pussy under those panties.

20180227_203342123552114.jpg

My sissy is getting closer and closer to permanently crossing that line between masculine and feminine.  She’s getting closer and closer to becoming more girl than boy.

I’m so excited to see how his body continues to change.  Aren’t you excited to see how his body continues to change?

Purple!

So I had to buy a new strap-on after my toy bag was stolen, and settled on a new harness and purple dildo.

20180107_175439

This purple dildo

And as it happens, Sounder bought some new lingerie to surprise me with. Which was purple.

20180107_172634

Isn’t she sexy?

So we’re color-coordinated, isn’t that fun?

And holy shit, my sissy looks amazing with things inside of her.  It makes me want to put even more things inside of her.  Bigger things.

Like my fist.

Yeah, that would be hot as hell.  Let’s make that happen.

The good bottle or the bad bottle?

I love games. Don’t you love games?

I totally love games.

I might have thought of a new game. Figuring out logistics will take some work, but it’s possible.

So Sounder is going to be fucked by Kazander. This we all know.

I was talking to Sounder about that today, specifically about how much of an eager sissy cockwhore he is with me, and how much he dreads being fucked by a man.

What, Jen? What would be awesome?

I’m glad you asked.

Okay, so Sounder has never had a real cock in him. He has no idea what that feels like. He doesn’t really know what to expect.

So here’s what I’m thinking. I’ll tie his wrists to his ankles and lay him on his side.

Like this, except with rope and on his side

And I’ll blindfold him, so he can’t see anything.

Then, either Kazander or I will come up behind him and enter him, careful not to touch him except for the cock.

And then, once one of us is inside him, he’ll have to guess who it is.

We’ll have to be careful, though.

Because if he feels a strap-on harness or bare skin, he’ll know who’s in him. He also knows my touch, so if one of us grabs or touches him, he’ll know.

I’ll have to use a new dildo, too. One right about the same size as Kazander’s cock, that Sounder has never seen. Preferably one of the ones that are supposed to feel realistic.

With him tied up like that, we should be able to get almost all the way in him without touching him.

Hopefully. And that’s where I wonder if it might not be feasible. There’s such a tiny margin of error. If he feels or senses or hears anything else, it’ll tip him off.

But if it goes right…

All he’ll have to go on is the cock inside of him.

If he guesses right, we’ll spitroast him, with me fucking his pussy and Kazander fucking his mouth.

If he guesses wrong, we’ll switch. Kazander will fuck his pussy and I’ll fuck his mouth.

And of course, I love the idea of Kazander being the one in him, and then when he makes his guess, I’ll take the blindfold off, and he’ll look up to see if he guessed right.

And he’ll look up to meet the eyes of the man whose cock is inside him right at that moment. Not only will he realize that a man’s cock is penetrating him for the very first time, but he’ll look up and meet Kazander’s eyes, as he feels his cock filling him up.

Whether or not he guesses right, that could be a fun moment.

Of course, if he guesses right, that means Kazander will pull out of him and start fucking his mouth. So he won’t have to be fucked by a man, but he’ll still be facefucked by one, and he’ll still have to swallow his load, and he’ll get to experience ass to mouth for the very first time.

But then again, that may be too easy. Sounder is very much aware of my love of a good mindfuck. And putting Kazander in him is definitely something I would do, just to fuck with him.

So he would likely expect that.

And besides, it would also be amazing if I’m the one in him, and he guesses wrong, and realizes that he could’ve had me fucking him, and instead he gets to deepthroat my cock (which was just in his pussy) while a man fucks him.

But he may expect that, too. Because putting Kazander in him is the obvious choice. He knows I’m not going to go for the obvious choice, so he may expect that it’ll be me in him.

In which case I’ll definitely need to put Kazander in him.

Really, it’s less about trying to determine what’s inside of him by the way it feels, and more about what he thinks I’m going to do.

It’s like that riddle in Sherlock and Princess Bride.

Did I put my cock in him, or Kazander’s?

“Did I give you the good bottle or the bad bottle?”

You know, except no one dies, and we spitroast a sissy.

How many times will I go back and forth before settling on the answer? What do I think he’ll expect me to do? What does he think I’ll expect him to guess?

Like I said, I don’t actually know if it can be done, but if it can, you’d better believe that’s what I’m going to do, and it’ll be so much fun!

Sissy porn stash

It’s been a busy couple of months, but no matter what else is going on, I always make time to enjoy just how sexy and photogenic my sissy is.  And luckily for me, I have my very own personal sissy porn stash.

The last couple of months have been a bit wonky as far as both of our schedules go, but usually, if I’m not there with him on Sissy Sundays, Sounder makes time during the day to take pictures for me.

And they’re beautifully edited, so delightfully slutty, and unbelievably hot.

The pictures I take of him are pretty fun to look at, too.  I’m never ever going to not enjoy seeing him with something inside him.

20171228_023507.jpg

Case in point

I mean, just look at that gorgeous, perky ass.  It just begs to be filled.

My favorite, though, is the stuff I can’t share here.  Particularly the videos I’ve taken of him.

Like the first time he came while straddling me, riding my cock.  That’ a fun video to watch.  Or the most recent one, of him on all fours in that sexy lingerie, fucking himself on the dildo, arching his back and pushing against me, wanting it deeper inside him.

The holidays have messed with my ability to fuck that sexy, slutty, eager ass of his.  But it happens, real life tends to get in the way of kinky fun occasionally.

And at least I have some amazing porn to look at until I can throw him down onto the bed, push his legs back, and ram my cock into him over and over again.

A good, thorough fucking

It had been awhile since I’d been able to give Sounder a real fucking.  We were both eager for that to change.

And from the very first moment I bent him over the island in his kitchen, and slid a finger in him, he was every bit the eager anal whore you’d expect a sissy to be.  Pushing back against me, humping himself on my hand, wanting to be filled up, it was really hot.

I always love watching him squirm.

It was especially hot once I got him in the bedroom and started putting toys in him.  I will never get tired of watching him fuck himself on whatever’s in him.

20171105_185154

I can’t wait to take a picture like this, but with a real cock inside him, instead of a toy.

At first, he was so tight.  It had been too long since I’ve really had my way with his pussy, so I was gentle.  I started small and gradually worked my way up in size.  Because I’m so totally nice like that.

All I know is that he’s going to make a man very happy when I put a real cock inside him.  And how awesome are backless panties?  The more he wears them, the more I love them.  So sexy, so convenient.

I don’t even have to undress him, all I have to do is bend him over.

When I finally switched to my strap-on, the look on his face as I filled him up was priceless.  It had been awhile since he’d had anything that big in him.

I turned him onto his back, pushed his knees up, exposing that tight, pink ass, and rammed my cock in.

He looks damn good with something in him, by the way.

I don’t think it was a full minute before he came.  And then came again.  And again.

We’ll definitely have to work on his stamina.  He starts getting exhausted and raw after about ten orgasms.  He’ll have way more than that when he’s fucked by half a dozen men.

Eventually, though, I had mercy on him, and decided to play with my clothespins, instead.  You know, because I’m nice like that.

20171105_185727

Super nice

He really is so adorable when he’s in pain.  And the best part about clothespins is that they hurt more coming off than they do going on.  Makes it easy to drag out the pain, really savor those reactions.

And he’s got a new hypnosis recording to listen to every day.  I’m going to brainwash him into a mindless sissy fucktoy.  He’s going to dream about being gangbanged, he’s going to crave men’s cocks in him.

Eventually, it will even seep into his everyday life.  He’ll be at work and see a hot guy, and an image of that guy bending him over his desk and fucking him will flash through his mind.  He’ll imagine what that man’s cock will taste like.  What it’ll feel like to have it throb in his mouth as it shoots down his throat.

Just a quick flash.  But they’ll start happening more and more, until that’s the norm, until he doesn’t remember what it feels like not to picture men fucking him.  He’ll forget what it feels like not to crave a man’s dick inside him.

It’s going to be so much fun, it really is.

Facials are fun

So I’ve had the worst luck with electronics lately.  For the last two weeks, I’ve been without a computer.  But it finally got in, yay!

And there’s a lot to be happy about.

In two weeks, I’ll get to see Southern again.  It’s been a couple of years since I’ve seen him, so I’m looking forward to that.

And, for those of you who check out Jessie’s blog (and all of you really should), you may have noticed a fun little game I played with him, where he had to send a text to Kazander, asking him to cum in his mouth.

Fun stuff, it really is.

So he sent the message, and a few days later, Kazander and I pulled up to the house.

I was beaming from the moment we walked through the door.

Jessica was dressed in her gorgeous corset, backless panties, stockings, heels, her hair and makeup done.  She looked sexy as hell.

Her face looked so pretty, I just had to stick a penis in it.

And Kazander is quite the Top, as it turns out.  When we’d talk about how we wanted the evening to go, I often had to remind him that we could push Jessie, we could have all sorts of fun fucking with him, but we had to exercise some restraint, as well.

We had to toe the line between intense and too intense, but we couldn’t violently shove him into the deep end with no warning.

“Dear, if we break our toy, we won’t be able to play with her anymore.”

You know, balance.

But as I’ve said before, I’d much rather have to hold him back than try to pull enthusiasm out of someone who’s just not feeling it.  The fact that he’s sort of taken this and run with it is a million kinds of freakin’ awesome.

And he has the benefit of having been my sub for 7 years now, so he knows me, he knows the kinds of mindfucks I like, and he knows the general flow of how I like having sessions go.  His biggest kink is humiliation, so he’s very experienced in the field of receiving it.  Since he’s got the switchy tendencies, he can take what he finds hot when he’s in the submissive headspace and turn it around when we’re with Jessie.

So now I have someone to help me utterly humiliate and degrade my sissy.  Which is a huge, massive bonus for me.

We sat down on the couch, and I had Jessie get on all fours at our feet.  Only a moment later, Kazander’s cock was in her mouth.

I was determined to make it last longer than last time, though.  I wanted to really savor the experience.  I wanted to draw it out a bit, and let all three of us enjoy it.

Well, let two of us enjoy it, anyway.

That morning, and the previous night, I’d had Kazander cum.  Normally, I enjoy keeping him chaste and denied, so he doesn’t last very long when I do let him cum.

Last time, that (combined with Jessica’s exceptional cock-sucking skills) resulted in him cumming too quickly.  I made sure to prepare so that didn’t happen this time.

It was so hot watching Jessie suck Kazander’s cock, watching her head bob up and down as she deepthroated him.  She’s definitely been practicing.

After a moment, I knelt down on the floor next to her and reached behind her, rubbing her clit.  Her p-spot has always been so sensitive, and I wanted to see if rubbing it would have an effect on her cock-sucking.

You know, for science.

She started squirming, arching her back, pushing her ass out against my hand, very literally humping my hand while she sucked his cock.

I grinned and looked up to Kazander when I heard a soft moan come from her.  “Does this make a difference?” I asked him.

“Oh yeah,” he replied.  “Whatever you’re doing, she likes it.”

My hypothesis was confirmed.  Gotta love science.

It was so hot watching her, squirming and writhing and moaning, her moans muffled by Kazander’s cock.

One of the things Kazander had suggested earlier was giving Jessie a facial, and cumming on her face, instead of in her mouth.  I was intrigued by the idea, but didn’t really think much of it.  We’d already settled on making Jessie swallow his load.  I didn’t see a reason to change the plan.

But when Kazander told me he was getting close, I suddenly changed my mind.

“Stop,” I told her.  “Lie down on your back.  He’s going to cum on your face.”

So she did, obediently lying underneath Kazander, her head between his legs, her eyes closed, while Kazander jerked off onto her face.

And she looked so pretty with his cum all over her face.  But then again, she’s a sissy, it’s pretty common knowledge that they always look good drenched in real men’s cum.

She wasn’t done, though.  Before she could move, I reached down and rubbed it all over her face, then put a cum-covered finger against her lips.

“Open,” I said.

Reluctantly, she obeyed, and I pushed my finger into her mouth.

“Suck it clean, that’s a good girl.”

Kazander went to get himself cleaned up, and I had Jessie sit at my feet, rubbing Kazander’s cum all over her face and making her suck it off my fingers.

The awesome thing was after a few seconds, that reluctance disappeared, and she leaned against me, enthusiastically sucking and licking my fingers clean.

Like a good little cumslut.

And honestly, that was my favorite part of the whole thing.  Just the way she completely embraced that sissy mindset, the way she eagerly sucked the cum off my fingers, it was just so damn fucking hot.

My precious sissy whore.

After Kazander left, I let Jessie come up and sit next to me on the couch, and rubbed her clit some more.  She came again and again, with Kazander’s cum drying on her face, and the taste of it in her mouth.

There was a funny moment, though.  We all know she can’t cum like a man anymore, she doesn’t even squirt.

Every time she came, she looked down to Tammi Lynn, tucked away in her panties.

“Are you checking to see if you squirted?” I asked after the third-ish time.

“Hoping I had,” she answered.

“Hoping you’d squirted?  Why?”

“Because then at least there’d be something to get the taste out of my mouth.”

“Oh, you mean the taste of another man’s cum?  Was that what you meant?”

“How’d you guess?”

And naturally, I found that just wildly entertaining.

My sissy bitch was hoping she could cum like a man, so that I would feed it to her, to get the taste of Kazander’s cum out of her mouth.

That’s where her mind went.  That’s the solution she came up with for how to get the taste out of her mouth — using her own cum to do it.

I mean, how awesome is that?

My precious sissy is growing up.

A fun conversation

I do love when other people help me come up with ways to humiliate Sounder.

As it turns out, Kazander is pretty good at coming up with awesome ways to humiliate Sounder.

We were talking about him over the weekend, discussing things like how good he is at giving head and how cute he squirms when he’s being fucked.  I lamented the fact that no one other than me has seen just how cute Sounder squirms, and Kazander shrugged, saying, “Let’s change that.”

You know, that is just a capital idea.

But you know what would be more fun?  If Sounder is the one to ask Kazander to fuck him.

That would be so much more fun.

Except that’s not enough.

I want Sounder to be the one to initiate that conversation.  So I gave him Kazander’s number and told him that, in order for me to play with him again, he has to text Kazander and ask him to come with me, and put his cock inside Sounder.

Naturally, Sounder isn’t particularly thrilled about this fun little game of mine.  Being fucked by a man is going to be rough just on its own.  Having to be the one to ask for it to happen, to ask the man to fuck him, to take his virginity, is just icing on the cake.

It’ll be such a fun conversation.

Isn’t this an awesome game?