Outstanding in the field

Four years later and I'm back with a new post! Sometimes pictures write their own story, so I wanted to share this somewhere.

Not sure how often I'll post going forward, but will as the urge hits.

So without further ado...enjoy!

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We live in a small town where everyone knows each other and gossip spreads like a weed. So one of my best friends was taken aback when I revealed I'd recently been thinking about gender identities and sexual preferences. And more specifically, how I'd been second-guessing my own.

I timidly asked him if I could give him head, just to see what it was like. He was rightfully reluctant, but I eventually made progress after repeatedly reminding him we could stop at any time, no one would ever know, and he'd be helping me out with my soul-searching.

So he agreed to drive separately to a remote field early one morning. I'd arrive first so I could change clothes and put on some makeup before he ever saw me. When he showed up, he met me out in the field, out of the sight of anyone driving by. 

Without talking, I helped him get his penis out and put it between my lips. He slowly grew as I worked him in and out of my mouth. We must've both enjoyed the sensations of what was happening, since we kept going at it. As an aside, I hadn't expected to make eye contact with him throughout, but yeah, that totally happened which was kinda sweet! 😉

After some time, I increased my pace and urgency, and he came in my mouth. I thought I was ready for this moment, but some spilled on the ground as I gagged a little. Oops! But I tasted everything he gave me, got a feel for his consistency and warmth on my tongue, and then swallowed it down.

I then waited for him to walk back to his car. Once he drove off, I cleaned myself up in my own car and changed back before heading home.

When I next saw him, I thanked him for our rendezvous, I know it took courage on his part. His face lit up and he admitted it wasn't as awkward as he first imagined. He asked me how my journey was going. I smiled and said, "It's going well, I'm definitely learning more by experience! Speaking of which, I really enjoyed our meet-up the other day. What would you say to a second secret date?" 

He said yes...I can barely wait! 

Hiatus

Thank you to anyone that has read my blog, and I hope you've enjoyed at least some of my posts.  

At this time I've decided to take a break from this blog.  

I've titled this post "Hiatus" since I know writing can ebb and flow, and may continue again sometime in the future.

Until then...

Subtle sissy hints

Talking to my wife about exploring my feminine side was one of the hardest things I've done in my life. 

How do you introduce the subject? 

How do you break the news? 

How will she react? 

What if she's repulsed? 

Luckily she listened and agreed to consider what I was saying, and over time was pretty accepting.

The second hardest thing I've done in my life was tell her I'd been thinking about cocks, wondering what it would be like to put one in my mouth. All of the same questions from before came screaming back into my head.

For whatever reason I started dropping hints instead of just sitting down with her and being honest.

For example I asked her, "Sweetie, why don't we take a day trip tomorrow? I was thinking we could take the ferry across the bay and find a hiking trail. It's almost peak foliage."

"Sure, Babe, that sounds like fun. Why don't you look up some trails before we go."

Then while I was preparing the backpack with supplies, I slipped a book into the bottom. Once we were settled on the ferry, I subtly took the book out and waited for her reaction.  She was busy watching the scenery out of our window and didn't take any notice.

That's when I dramatically lay down with a big sigh.  I put my head down by the window with the book covering my face.  

That's when I heard my wife start giggling.

"Honey, is there something you want to talk about?" she asked.

Maybe my clue wasn't as subtle as I thought?  I peeked sheepishly over the book and took a deep breath. It was now or never.

"Actually, there is..."

It's all in the delivery

We ordered supper about an hour ago, so the delivery guy should be here any minute. I look down the road, shielding my eyes from the afternoon sun.

My wife appears by my side from out of nowhere. "No matter how hard you look, sissy, you're never going to find your masculinity again."

She laughs at her own joke as she walks back inside.

Sissy mentality

Putting on panties, a bra, stockings, a pretty dress, and high heels makes me feel feminine.  

Accessories like a matching headband, bracelet, and complementary earrings add those finishing touches.

Carefully applying foundation, blush, eye shadow, mascara, and lipstick helps me appear passable.

But bring out a big cock and I instantly become a submissive sissy slut that's not afraid to get dirty.

Sissy sandwich

"What do you say, sissy?" my wife asks as he enters me from behind.

"Thank you, ma'am, for letting me join you both in bed tonight."

"Oh Honey, it wasn't just my decision.  Use your manners and thank our guest as well."
 

"Thank you, sir, for including me in this moment," I say sincerely.  "I feel very lucky."

"While I agreed to this, it was your wife's idea to fuck you in front of her.  She wanted you to experience this too."

"Oh...yes sir, you're so big.  Uh, yeah, give it to me please," I beg.

The three of us writhe in ecstasy on the bed.  He pushes deeper inside me while my wife's hand finds my limp, wet cage.  

My climax builds as his cock rubs my prostate.  Their bodies press against mine, one from either side.  

My brain finally short-circuits as the sensations are overwhelming.  My muscles tighten, my limbs contort, and I inhale sharply.  I wait patiently to come back down to earth.

Now I see why I was included tonight.  Now I truly understand why she needs him in her life.

Sensitive nipples

"I love playing with your nipples, sissy!"

" I noticed you've taken a new liking to them recently.  How come?"

"Oh...um, they're...I mean when I found how hard they get when I rub them, I just can't stop."

"To be honest, it does feel so amazing.  I guess I never realized how sensitive my nipples were.  Who knew?  Oh, before I forget, you got a box in the mail today.  I left it on the counter.  What'd you order?"

"Oh, it's just your supplements.  You were almost out.  I'll fill your pillbox back up for you."

"Thanks, I really think they're working.  My face is less oily now and my skin just seems softer overall."

"Really?  I hadn't noticed..."

Remembrance: college

The apartment's quiet this Saturday night.  Usually us guys make the rounds at the bars, but tonight I tell my three roommates to go on out without me.  

I'd promised to hang out with my close friend Shannon, who'd been my friend since freshman year and just had a rough week with her boyfriend Jeff.

Shannon stops by shortly after they leave.  She's the only one that I've let in on my crossdressing secret.  She needs a distraction, so I ask her if she wants to help me dress up.  She says yes.

As she's putting the final touches on my makeup, there's a loud pounding on the door.  Peeking through the blinds, I see it's Jeff.  I roll my eyes.

I open the door slightly.

"Can I help you?" I ask him.  The stench of beer permeating from him makes my nose wrinkle.

"Who're you?" he asks, slurring his words.  He double-checks the number on the door.  "I wanna see Shannon."

"We're done, Jeff," Shannon says as she appears by my side.  "I've got nothing else to say to you."

"C'mon Shannon.  You don't mean that."

"Yes, I do.  We're through," she continues.  "I've got no use for you anymore."

"Fine.  How 'bout one last blowjob before I go?"  Jeff, being drunk and at the end of his relationship, apparently likes to burn bridges.

Shannon and I just start laughing at his nerve.  Then a hand cups my ear followed by a whispered voice.  "Have you ever given a blowjob?"

I spin towards Shannon with a look of shock on my face.  Slowly, I shake my head side to side.  This is a harmless white lie as I did give one dressed as a cheerleader and another at a house party.  But I digress.

She tips her head towards Jeff and raises her eyebrows questioningly.  I stare at her a moment, then slowly nod my head.  She mouths the words "follow my lead".

"You know what, Jeff?  We were together long enough, why not enjoy one last blowjob.  Come on in!" she says opening the door all the way.

Jeff smiles triumphantly and ambles inside.  She leads him to my room, where he collapses on the edge of the bed.

 Shannon opens his fly and pulls his dick out.  I see it's already starting to harden.  He doesn't seem to notice I'm in the room watching.

"Yeah, Babe, that's it," Jeff moans as Shannon takes him in her mouth.  Her head bobs slowly as she pleasures him.  He leans back and his eyelids droop with satisfaction.

That's when Shannon waves me over.  This is it, now or never.  I quietly kneel next to her and take hold of his cock as Shannon slides back.

Now that I'm closer I see Jeff has an average length cock, but wow is it thick!  It's still slick from a mixture of Shannon's saliva and his pre-cum.  I lick my lips with cock-lust.

Jeff mutters, "Oh, don't stop, Babe.  It feels so good."

I glance at his face with his half-closed eyes before placing my mouth around his hard-on.  My tongue finds his tip and settles underneath.  I create a vacuum with my mouth and move down his shaft.

I can't believe I'm going down on my friend's ex as she watches.  Also, I realize it's been way too long since I've had a cock in my mouth. 

I pick up the pace as Jeff moans.  I don't know how much he drank tonight, but hope he comes down my throat before he goes limp or passes out.  I really want his load!

I find myself really horny and getting into it.  Moans escape my mouth as I loudly suck and slurp with urgency.  

Jeff's moaning and groaning as well.  I think I even spot Shannon rubbing herself through her leggings out of the corner of my eye.

Suddenly I feel Jeff's hands on my head, pulling me firmly down his shaft. The head of his cock is pressing against the back of my throat.

"Uh...oh, yeah," he utters. His cock starts throbbing in my mouth as I wait for it. Then a spurt of his salty warmness hits the back of my tongue and another shoots down my throat.

He continues gripping my head between his big, strong hands while he waits for his orgasm to subside.  

Without much choice in the matter, I focus on swallowing the delicious nectar so it doesn't dribble out of my mouth. Shannon let's out a gasp as she watches me hungrily take everything he's got.

When he's done he puts his hands behind his head, and sighs contentedly.  

Shannon and I switch places again. She helps him back into his jeans as I wipe a few errant gobs from my chin into my mouth. 

Finally, we help him find his way out of the apartment. Surprisingly, he doesn't have much to say as he leaves.  But Shannon and I are giddy for hours!

Yin and yang

"Oh....uh-huh...that's the spot," she purrs.

With her legs spread before me, I grip her thighs and delve my lips further into her shaved mound.  My tongue finds and softly caresses her clit.

Her body shifts slightly as she places her heels on my back and pulls me even closer.  "Oh yeah, Baby," she moans.  "This is why I keep you locked up.  You understand why, right?"

Of course I understand.   She allows me fewer and less frequent orgasms, but routinely has me pleasure her.  Helping her reach orgasms fills me with lust.  Being denied release, I'm always in a constant state of arousal.  She's the one holding the key to my chastity cage, so I'm forever thinking of her and her happiness.

As she screams in ecstasy I remind myself that although I'm locked in chastity, it really is a perfect balance.  We're still useful to each other, and our marriage has never been stronger because of it.

 

Kitchen gadget

 

I've got to get all these holiday cookies baked, frosted, and out to all the neighbors.  Of all the times, why did he have to pick NOW to pull down my panties and bend me over the counter?

Ooh...well, maybe I can afford to be distracted for another minute or ten.  But I swear, once he finishes, the cookies are as good as out the door!

Adjustments

"Seriously, I don't know what you'd do without me," she said while pulling the nylons up my leg.  "You know you can't go around with your pantyhose all gathered up.  Maybe we need to buy you the next size down?"

"Yes, ma'am.  A smaller size would probably fit better."

"And for goodness sake, stop rubbing your legs together like that!  It looks like you need to use the restroom."

"Sorry, ma'am, it just feels so good.  Whenever I put them on, I can't resist doing it."

"Ugh, you and your sissy ways.  I just don't understand you sometimes.  Oh well, are you ready for our fancy date night in?"

"Oh yes, ma'am, I've been looking forward to it all day!"

 

Many happy returns

They left our house at the same time this morning, her car headed to the office and his back to his place.  Five minutes later, his car pulls back into the driveway.

"Back so soon?" I ask, meeting him at the door.

"Yeah, well I keep thinking about what you've got going on in this house of yours.  I've got to admit it's unusual, but definitely kinky."

"Well, what specifically brought you back just now?"

"To be honest, you've got this gorgeous mouth.  I keep picturing you putting it to good use, if you know what I mean."

"Yes, I think I do, and I'm happy to oblige.  Do you want to do it right here?"

"Well, let's take it inside.  You know what?  You've got a youthful face.  Do you mind dressing up as a schoolgirl?"

"Ah, I see where you're going with this.  I do have a schoolgirl outfit...what good sissy doesn't?" I ask with a giggle.  "Why don't you head into the den and make yourself comfortable.  Meanwhile, I'll go freshen up and meet you there shortly."

I have to admit I don't get the schoolgirl fantasy myself.  But I know it's a popular one with men, so I'm happy to dress up and play the part.  What's the harm if everyone is happy, right?

She drives

 

It's nice when she drives.  

I can just put my feet up,

sit back and relax.

Grinding

It usually starts the same way when she has a guest over.  My wife will excuse herself to the bedroom and return wearing just an over-sized t-shirt.  Sometimes she'll wear panties, depending on her mood.  Then she comes back and sits next to her guest.

At some point she'll turn around on her knees and look out the window.  She'll say something like, "What was that?  Did you hear something?  It sounded like it was outside."  It's usually nothing though.

When we see it's all clear, she'll pull him up behind her and start grinding her ass and pussy against his crotch.  The men always get hard and try to move things along.

That's when she tells them to stop and stay still.  She continues rubbing herself on them for as long as she can.  She absolutely loves to tease, and stretches out the foreplay for what feels like hours.  All the while, I hear her sighing and gasping.

I know she's getting wetter by the minute.  All I can do is sit and watch them grinding and breathing heavy.  I keep undressing them both in this position, visualizing the man entering my wife, taking her sexually.  Soon I feel a wetness in my own panties.

Most of the men have been physically fit; muscular arms, wide shoulders, and narrow waists.  Much more manly than I have ever been.  I know they'll satisfy her needs, which is a good thing.  But I wish she'd just let him pull her shirt up and fuck her already.

I don't think I can take much more of this grinding.

Aftercare

"That was a great suggestion, dear.  Where'd you hear about that again?"

"Mmm"

"I didn't catch that, what'd you say?"

"Uhh...ahh"

"Okay I get it you're not ready to talk just yet.  That's fine.  You know, I feel really close to you right now.  I want us to do this again sometime.   We can discuss later."

"Mmm"

As I come down from the heights of our session, she distracts herself by massaging my back and gently drawing lines with her finger.

 

Amends

“I admit I’ve been kind of hard on you lately,” she says, looking down at me kneeling on the floor.

Am I hearing her right?  This almost sounds like an apology.  Well, as close as I’m likely to get from my wife.

“So you’ve arranged this for me, ma’am?” I ask, looking at the sight growing in front of my eyes.

“Well, let’s just say it’s your turn.  I had my go with him last night.  Actually, we went a few rounds, didn’t we?” she giggles, placing her delicate hand on his broad shoulder.  A sparkle from her wedding ring catches my eye.

“And if you’re really lucky, sissy, you may even be able to taste me when you suck his cock.  Would you like that, Sweetie?”

“Oh yes, ma’am, I’d like that quite a bit.”

“Good, now go ahead and enjoy your treat.”

“Thank you, ma’am!”

Sneak peek

 

It's been a long month of chastity and strict rules in the house.  My wife has completely cut me off from any sexual contact or pleasure.  Not that I mind my denial, but I do miss pleasuring her.

I'm not quite sure what the endgame is here.  I've asked some vague roundabout questions to see if I can figure out what she's up to, but she just smiles at me.  I know better than to ask directly, as she's spanked me recently for less.

Anyway, I've finished my Friday chores and am resting my feet before making dinner.  That's when my phone buzzes.  She's sent me a picture of her bikini bottom pulled away from her body, clearly exposing her closely-trimmed mound.  Underneath she's typed, "missing this?" with a smile emoji.

I recognize it for what it is...a tease.  I'm still no closer to the answer though.  Where's she taking this?  What's her big-picture plan?  I look at the picture again and smile.

I imagine her beckoning me over with a simple wave of her index finger, spreading her thighs as I approach.  I can almost see her slit now, glistening with arousal.  Her irresistible scent reaches my nose and draws me still further inward, I'm officially under her spell.

The sound of the door pulls me out of a daydream.  I blink and take a deep breath before getting out of the chair.  She'll probably want her drink topped off before I start on dinner.

Punished

"Come here," my wife says simply.

"Yes ma'am," I reply.  I walk towards her as she stands by the couch.  I know what's coming, but am still fearful.

"You know the routine.  Assume the position."

I pull my dress up, slide my panties down my thighs, and lean against the back of the couch.  I close my eyes and wait.  I feel her body as she leans over me, her mouth near my ear.

*SLAP*

"That was for not replacing the empty toilet roll this morning."

*SLAP*

"That was for lunch being three minutes late."

*SLAP*

"That was for forgetting to tell me my sister called.  How many does that make, sissy?"

"Three, ma'am."

"Okay, that's enough for now.  I hope my expectations are clear.  Think you can meet them moving forward?"

"Yes, ma'am.  Clear as day."

"Good, sissy.  You may get dressed."

 

Remembrance: discovery

I don't remember the day of the week.  I don't remember the specifics of my family's whereabouts.  But how could I forget the curiosity that led me into my sister's room to try on women's clothes for the first time!  

The dresser drawer full of panties and bras, the closet full of skirts, dresses, and blouses.  The soft and exhilarating feel of the fabrics on my skin, and how the layers felt as they brushed against each other with every movement!

I knew right then and there that a whole new world was opening up to me.  Little did I know this was the sound of the siren's song.  Alison was beckoning me to let her out.  I'm so glad I listened!

Running a tight ship

So my wife has recently become more demanding and strict.  My daily chore list seems to grow longer by the day.  Today's list included laundry, washing dishes, making beds, vacuuming, and cooking meals.  

Every finished task was followed by an inspection.  If it failed to meet her expectation, then I was punished.  Spankings and corner time were her favorites today.

Don't get me wrong, I'm happy to do housework.  However, the lengthy list and detailed reviews are out-of-the-ordinary around here.  

I asked about the changes, and her response is that I've gotten sloppy lately.  She wants me to pay closer attention to details.  She thinks I'll have more pride at the end of the day for a job well done.

Besides, she says idle hands are the devil's workshop.  With more time at home lately, she wants to make sure I'm not getting lazy, or worse, into trouble.  

To that end, she bought a smaller chastity cage for me.  She said mine was starting to seem "roomy".  After I thanked her for the gift, we struggled to get me into it.  I'm smaller than average, but it still gave us a good fight.  A cold shower seemed to help in the end.  It feels cramped now, but am confident I'll adjust to it over time.

Lastly, she's declared that until further notice I am to remain chaste.  No sexual contact with any other person.  The use of toys is also forbidden.  I'm to go directly to her and be truthful about any infractions, which will be dealt with in a tough but fair manner.

These will be trying times, but I know her decisions are coming from the heart.