Caption of the Month - XI

Are any of us surprised?  Good god, this caption...this finality of it...the fear that must be gripping that poor sissy when she realizes her mistake just an instant too late!

Re-Blog Wednesday - 50

Retro Caption - 21

I can't remember where I got this one, but I've always loved it.  Just something about the power of the girlfriend, and her forbidding the sissy to cum, even when he's having his ass fucked.

Cap of the Week - XLVII

There are times where I just need someone to remind me of my place.  This caption encapsulates those times.

Sissy Review - V

 

 

April’s review is coming courtesy of Courtney's Clean Caps. This is another blog I’ve been frequenting for a while.  Having gotten its start around 2012, this site has the rare honor of being (to my knowledge at least) 100% original content.  Not bad for a blog.  Of course, there are multiple writers, so that makes it a lot easier to pull this off, but original content is something should always be applauded.  Courtney’s blog is pretty much 100% captioned images, though they have branched out into Amazon self-publishing, lately (and good for them, anyone that can make a buck off of sissy-dom deserves to).  The captions are the longer-formed story-types, that often involved some element of forced femme, and/or punishment.  Often, these captions involve some kind of sibling rivalry and some level of age-regression (more on that in a minute). 

 

I do, however, have a couple of issues.  First of all, the format is…not the best.  It’s still better than that eye-assaulting pinterest style, but each caption has a separate page dedicated to its image.  Again, it’s not the worst, but it can be time consuming if you’re…I dunno…trying to catch-up on 2-3 weeks’ worth of captions.  Also, the age-regression thing is…not my thing.  It can be done quite well and with great effect, however, there are times when browsing Courtney’s Place that I feel like I’ve been added to some NSA watch list.  The images skew a little too young, sometimes.  Maybe I’m an old prude but…well, actually, I’m not.  I run a fucking sissy-blog for god’s sake.  When your material makes me feel uncomfortable about seeing it, you might be approaching a line.  I’m not saying Courtney’s a garbage sex offender, I’m just saying she treads into territory that makes me uncomfortable.

 

One final point of note: Apparently, Courtney is an actual, biological female with an interest in the sissy-world.  A bit of a rarity, I find.  Rock on, sister!

 

Update Schedule: Multiple times per week

Typical Posts: Captions, Self-Published Amazon

Typical subject: Feminization, Punishment, Sibling Rivalry, Age Regression

Extra Points:  100% original content, updates frequently

Paid content: Self-Published Amazon Books

Would like to see more...content that won’t get me red-flagged by the federal government.

Final Rating 3 out of 5 (Perfectly Legal) Age Regressed Brothers

 

 

Re-Blog Wednesday - 49

My Life as a Sissy Maid XXII

Cap of the Week - XLVI

I love this cap so much it's ridiculous!  The subtle sensuality of him slowly sliding up the skirt, the last minute reluctance of the sissy...and the inevitability of what's to come, whether or not she's ready...or into it...

A Little Something for the Gurls at Home...

For those of you sissies who need to practice swallowing.

Re-Blog Wednesday - 48

Technically, this should be a "Like," but I think you'll forgive me.

Sissy Vid - 5

Here's a thing I haven't done in a while.

Via: Xvideos

Cap of the Week - XLV

Goddamn, I love the story of this caption!  Being forced to be the "entertainment" for a bunch of horny men!  Makes me drip pre-cum in my panties!  Great job from Pleasant Princess Candy!

I 💓 Hypno Gifs - 17

Re-Blog Wednesday - 47

Gotta say, that's a 4, for me!

Retro Caption - 20

Here's another old favorite that I've had for so long I honestly don't know where I got it.  If anyone knows, let me know and I give credit.

Cap of the Week - XLIV

Holy shit, what a great pic!  I just love how sure of herself she is!

Sissy Biography - V

Some time would pass before the subject of the panties would be reopened.  If I remember correctly, my, then-girlfriend and I were drunk in our room.  The subject of sex was being discussed, and we were being very frank about what we were into.  At the time, I was much more into bondage and S&M than I am now (depending on how you define the terms, of course), letting her know that I was into both dominating and being dominated (the latter would overtake the former later in life).  We kind of experimented with D/s stuff in the past, mostly her having to obey me when I gave orders, but nothing too serious.

It turns out that she always had a hankering for watersports…golden showers…While I appreciated the honesty, that fetish was a hard line that I refused to cross.  I can get into almost anything with the right frame of mind, but when it comes to bodily waste, I have a real, deep physiological reaction.  That is a fetish that has and shall remain unexplored for me.  I explained the notion and apologized to her, but held firm.  She understood, but wanted to revisit the subject at some point in the future.  Then, she gave me an oddly playful look.

 “So…tell me about your panties, again.”

"What do you mean?”

“Do you really just like the feel of them?”

I sputtered.  She had laid it out so plainly for me.  The big moment was here again.  The question was whether I going to run away, like I had in the past.  If I dodged the question now, would I get another chance?  What do I say?

“Well, I do…” I said, silently cursing my weakness.

She cocked her head to the side, saying nothing, but keeping her playful look.  I was trying to avoid eye contact to allow her to move on, but it was obvious that she was waiting for me to continue speaking.   The pressure of the silence quickly became too much for me.

“Well, I guess I, uh, also like um…wearing panties,” I managed to stammer out.

“I knew it!” She said, her voice full of satisfaction.

I hung my head, my confession had taken a toll, and I couldn’t bare to look at her.  My penis, however, began to spring to life.

“So, would you want to wear my panties?” She asked, her voice somewhere between mocking and curiosity. 

I gathered enough energy to raise my head to look at her.  She was looking me directly in the face, her green eyes and teasing smirk making me quiver.

“…yeah…” I said, breathlessly.

She walked over to the dresser and picked out a pair of white cotton bikini panties.

“Tell you what,” she said, “close your eyes.  I’m going to grab some things.  When you hear the door close, put these on, and put on that shirt of yours I like.  Then, kneel in the floor until I get back.”

I stared wide-eyed at her, barely registering when I held out my hand to take the panties, their soft, cottony weight draining my head of blood, and closed my eyes.  She quickly rummaged through the closet and, after a few moments, she walked out the door, closing it behind her.

My eyes snapped open and dropped my pants, taking the time the time to feel the soft white cotton slide up my legs.  She didn’t give me any direction on what to do with my now incredibly engorged penis, so I left it untucked, pinning it into place with the waistband of the panties, almost cumming at the friction it created.

The shirt was a hunter-green button-down that brought out my eyes.  She loved that shirt.  I imagine it made a weird picture, me in my button down, rock-hard erection sticking out over the waistband of a pair of simple, white cotton bikini panties.

I knelt, directing my eyes to the floor in front of me, and I waited.  Everything in me wanted to grab myself and stroke myself frantically, but I held on, trusting that the best was yet to come.

One minute went by.  Then, five.  Still no girlfriend.  I was beginning to wonder whether the whole thing was just a vicious joke at my expense when the door creaked open and then closed.

I looked up and saw that she was dressed in a fire red negligee, and had a flogger she had bought at Spencer’s Gifts.

She crossed the distance to me, looking at my panty-clad penis.

“Untucked?” she said, a little confused.

“You didn’t tell me what you wanted,” I said.

She chuckled, and told me to stand up.  She leaned in to kiss me, but stopped a hair’s breadth away.  I remember being able to feel her breath on my lips.

She then reached down, feeling my scrotum through the panties, and rubbed the underside of my shaft in one long, sensuous stroke, from the bottom all the way to the tip of my penis, my eyes rolling back as she did so.

She spent a little bit of extra time stroking the head, smiling as I breathed in deep ragged breaths. 

She then rubbed her index finger around my tip before placing her finger in my mouth and telling me to suck it.

It was the first time I had ever tasted my pre-cum, its sticky sweetness taking me by surprise.  She chuckled as she worked her finger in and out of my mouth before taking it back and collecting some more pre-cum.  This time, she held her glistening finger inches from my mouth, as if waiting for something.  I gave her a look, and she turn her head and smiled.  I knew what she wanted, and leaned forward to place my lips around her to suck it clean, again.

“There you go, suck it,” she said, in a throaty whisper “You like wearing my panties, don’t you?  I can tell.”

I nodded and breathed deep.

She withdrew her hand and reached into my panties, grabbing my cock, her warmth sending electricity throughout my body.  She leaned in close, her mouth to my ear, and started pumping me slowly.

“So, what do you want to do in my panties?” She whispered.

I couldn’t answer; I could only breathe ragged breaths.  By this point, there was no intelligible thought in my head.

“What do you want to do to me in your panties?”

“Fuck...” I breathed, an exclamation rather than a statement of intent.

She let go of my cock, and I groaned in disappointment.

“You have to tell me what you want,” she said, looking me in the eye.

I tried to speak, but all I could get out was, “Jesus, I can’t…”

She smiled, and said, “I know what you want.”

She then knelt down and pulled my cock into her mouth, the wet warmth inviting a whole host of new sensations.  I didn’t last long, her licking, bobbing, and stroking led me to a fever pitch in probably less time than it takes to tell it.  I was powerless to do anything except feel the sensations that her mouth afforded me, eventually erupting into her. 

She gave a moan of pleasure as I came.

I came long and I came hard, jet after jet firing into her mouth.  When I finished, I could barely focus my vision. 

She stood up and leaned in for a kiss. 

Somewhere, deep in the back of my head, echoed an elated disbelief:  Was she really going for it?  Was she really going to do this—kiss me with a cum-filled mouth?!  Was my girlfriend really about to force me to taste my own cum for the first time after sucking me off while I was wearing her panties?!

She stopped just short, again, gave me a taunting smile, and swallowed.  No small part of me felt disappointed.

“Maybe that’s taking it too far,” she said.

I still couldn’t answer, suffering from some weird erotic whiplash of the past few minutes.  She stepped around and stood behind me, whispering in my ear.

“Drop your panties and take off that shirt.  You can put on whatever you want, but I need some attention,” she said as she lay down on the bed, propping herself up on the headboard, waiting for me to follow her directions.

I unbuttoned my shirt immediately, and pulled down my panties, my spent penis winding itself down.  She said to put on whatever I wanted, and I knew exactly what to pick: her pair of hot-pink string-bikini panties.  I had always admired them from the moment I saw them, and had worn them more than a few times when I knew I was alone.  The thought of wearing them in front of my girlfriend would probably be enough to get me completely hard, again.

I quickly pulled the panties up my legs, letting the elastic strings rest on my hips.

“I knew that’s what you’d pick,” she taunted.

I stiffened at her words, and turned to face her, a look of smug satisfaction on her face.  She motioned for me to join her, pointing to the foot of the bed.

I followed her directions, and put one knee on the mattress.

“Did you tuck this time?” She asked.

I felt my pupils dilate when she said it, and shook my head.  I reached between my legs—my flaccid, used penis threatening to spring to life at the scene—and positioned it back, between my legs.  I took the time to admire how the hot-pink panties fit against my newly flattened crotch, and felt my cock-head rub against the fabric as I shifted my weight, a surge of electricity flowing through my body. 

“Are you coming?” Asked my girlfriend.

I began crawling over to her, working my way across the bed, but she put a hand on my shoulder to stop me.  I looked at her in confusion as she guided my head between her legs, lifting her red negligee up to her hips, revealing black satin panties.

She was ready for me, her scent wafted through the air and directly into my face.  I lean in and kissed her through her panties, before pulling them down her legs and tossing them onto the floor.  She gave me a flirty look before she slowly lowered my head in-between her legs.  I licked, I prodded, I worked every bit of her that my tongue would allow—worshipping her, breathing her in.  The more I worked her, the more my penis worked the fabric of the panties, enlarging me, sending me shockwave after shockwave of pleasure as I worked her to orgasm like a proper panty-wearing sissy-slave.

Eventually, her body tensed, her back arched, she squeezed her legs around my head and grabbed handfuls of my hair in her hands, letting out a long, raspy moan.  I continued working her until her body relaxed and she let go of my hair.

“God, thank you, baby,” she said, reaching down and pulling my head in for a kiss.

The kiss was long and deep and passionate, with the level of affection one can show only after an intense climax.  While we kissed, I felt her hand at the front of my panties, rubbing my flattened crotch, before tracing along the string waistband, and working its way under to where my cock had been tucked.  She felt my immense hardness through the panties, and gave a quick squeeze, rubbing it slightly.

“We might need to get back to this in a minute,” she said, mid-post-coital breath.

“Yeah, please,” is all I could get out as my head swam in the sensation of her hand working me through my panties.

“Just give me a minute,” she said before drifting off into a deep sleep.

I lied down next to her and quickly followed.  When I awoke, it was pitch-black outside in the dead of night.  It took me a while to realize that I was still wearing nothing but my girlfriend’s panties.  It felt like I was as hard as when I went to sleep, though my cock had freed itself from its tucked prison.

I snuck off to the bathroom and admired myself in the mirror, noticing my penis sticking out over the waistband of the panties.  I looked down at myself, seeing a glistening spot in the moonlight.   Reaching down, I collected a finger full of pre-cum, watching the rope stretch from my finger to the cockhead until it finally broke, and brought it to my mouth, letting a small groan escape my lips.  I continued feeding myself my pre-cum until it was gone, and briefly considered masturbating, but decided against it, in case my girlfriend had other plans.

I went back to the bedroom and went back to sleep.  When I awoke, my girlfriend was gone, as was any trace of what transpired the night before, even the black panties I tossed onto the floor had disappeared.  She had gone to work that morning and cleaned up the bedroom while I slept, still wearing her hot-pink panties.

I had to get to class soon, so I reluctantly pulled down my panties, and got ready for the day, leaving behind a fantastical night of sissydom, wondering and hoping what the evening might bring.

Re-Blog Wednesday - 46