Dianne’s Here!

I'm in chastity more often than not though that is all Megan's decision. Sometimes she just rolls a die to decide LOL. I enjoy how it works me up and keeps me aroused for days.

We usually sleep together unless she's sleeping elsewhere with someone else.
 
There aren’t hard and fast rules. Up until the last couple weeks, she would strapon fuck me 2-3 times a week until I came, usually without touching my clit. I’m caged about 50% of the time normally. Sometimes she makes me, other times she gives me the choice. The more deeply I am Dianne the more natural it is to be caged and not get that arousal bulge.
 
How's the week gone? Still caged or did Megan release you? How have you and Megan been dealing with the break up with Heidi?

Would you say your in Dianne headspace most of the time these days? Do you ever regret your journey?
 
So Megan is visiting family this week and Dianne has some “me time”. I’ve gone out as Dianne with Megan a few times, trying to find some cock for me (or us to share). Best I got was starting a handjob on a guy that I intended to suck but then his wife called and he fled.

So while Megan is away I decided to try some less risky adventures. I’ve been shopping in person as Dianne at Soma, Victoria’s Secret and a few other places like Torrid which is more Megan’s sizes but I can find some things there and they are super accepting. I can report that I was accepted everywhere and recognized as a crossdresser in all but one place. Lovely times talking with the sales girls and saleswomen and even some other customers. Tried lots of things on and heated up my credit card a bit LOL but I now have more of a real woman’s wardrobe to live in. (Okay yes and some naughty bits too…if you have a Lion’s Den near you try it out! I found something very realistic to feed my cocksucking cravings as well as a silly pair of high heels)

This will teach Megan not to leave Diannr alone with credit cards! 😉
 
So Megan is visiting family this week and Dianne has some “me time”. I’ve gone out as Dianne with Megan a few times, trying to find some cock for me (or us to share). Best I got was starting a handjob on a guy that I intended to suck but then his wife called and he fled.

So while Megan is away I decided to try some less risky adventures. I’ve been shopping in person as Dianne at Soma, Victoria’s Secret and a few other places like Torrid which is more Megan’s sizes but I can find some things there and they are super accepting. I can report that I was accepted everywhere and recognized as a crossdresser in all but one place. Lovely times talking with the sales girls and saleswomen and even some other customers. Tried lots of things on and heated up my credit card a bit LOL but I now have more of a real woman’s wardrobe to live in. (Okay yes and some naughty bits too…if you have a Lion’s Den near you try it out! I found something very realistic to feed my cocksucking cravings as well as a silly pair of high heels)

This will teach Megan not to leave Diannr alone with credit cards! 😉
I was in VS today and bought a couple of pairs of panties. I wasn't nervous or anything, however I wasn't bold enough to ask for a bra fitting, which I really need.
 
I was in VS today and bought a couple of pairs of panties. I wasn't nervous or anything, however I wasn't bold enough to ask for a bra fitting, which I really need.
You definitely should ask for one. Back when Dianne was in the closet I would go to VS and other stores with lingerie and always ask for help with sizes to wear lingerie and bras. So fun having women and young women measure you. Or having them show you how to lace a corset while you are standing there in said corset and panties! Lovely times.
 
You definitely should ask for one. Back when Dianne was in the closet I would go to VS and other stores with lingerie and always ask for help with sizes to wear lingerie and bras. So fun having women and young women measure you. Or having them show you how to lace a corset while you are standing there in said corset and panties! Lovely times.
I wasn't aware of that...and they didn't mind or give you an odd look or two?
 
Autumn is here and I'm slowly adding to my wardrobe with cute sweaters and skirts. Definitely will have more clothes than Megan soon. LOL.

The neighbor closed their pool a few weeks ago. I've had a fantasy about them, well, him, that I wanted to share based on how they let me come over and swim as Dianne several times in my one piece suits and bikinis. I don't know if Megan wants us to use codenames all the time but let's call the husband Tom and the wife Sara.

---

"We'll be closing up the pool this weekend," says Tom. He was sitting at the table by the house when I stepped through the gate between our yards carrying my towel, a clutch, and wearing my oversized sunglasses. Still nervous coming here, I was wearing my most risque swimsuit: bright pink, thong backed, high on the leg and with a little structure to give me incredible cleavage.

I put my towel and clutch down on the lounge chair next to the pool and slip off my sandals.

"That's a shame. It's been so wonderful being able to use the pool. I can't thank you enough for sharing."

"You're welcome anytime, Dianne," he says with a smile as I glance over at him, turned sideways so he sees my busty silhouette. I smile a little as I can already see his cock in his swim trunks.

I step over to the pool and dive in. It took me a long time to be confident enough of my breast forms but the ones I bought most recently are a perfect match to my skin, glue on smoothly and securely, and move and look just like breasts. Now I feel totally free to move like Dianne, my steps, my turns, how I sit all becoming naturally so feminine.

While I'd intended to get a proper swim workout, the thought of getting a different kind of workout is all I can think about.

I come to the edge of the pool, swimsuit glued to my sculpted curves. "Sara out for the day?"

"Visiting her sister. All week." Tom has a little grin. We've been flirting ever since Megan and I came over and had the talk about Dianne and asking to use the pool. I know he's had his eyes glued to me every time I swim, either sitting at the table or watching from his bedroom window. I would bet he was jerking off as he watched me.

I step out of the pool and make a show of drying off, special attention to my breasts and making sure my cock is still contained by the wide front of the swimsuit. I take a seat at the table with him and we both have a view of the pool and his beautifully created and private backyard. The air is thick with sexual tension as we start glancing at each other and then just look at each other.

"All week, you say? So she's not here now?"

"That's right. Just you and me."

"Was there something you wanted to say to me? you know, now that we have complete privacy and can be very open?"

He stands up and steps over to me. His cock is clearly erect in his swim trunks and he's larger than I'd hoped for. He adjusts the swim trunks to let his cock out and it hangs oh so heavy in the air in front of my face. I smile with my mouth and my eyes. My eyes drift to his cock, the one I've dreamed about and masturbated to many times.

I slip my fingers around the shaft, enjoying the heat and weight of it. At least 9 inches long and thick! My long pink nails show nicely against his skin. I gently start to stroke him.

"You are so beautiful, Dianne. The perfect woman..." he breathes, secrets he's kept so quiet finally coming out. "I've wanted you since the first time I saw you..."

I kiss the head of his cock and he gasps. Using my tongue, I give him little licks as I take my time exploring him the way I've fantasized about. Nuzzling him. Leaving little traces of my pink lipstick. Tasting his musk and arousal. Caressing his balls, so heavy with cum. When I finally slip the head of his cock past my lips he groans.

His cock is too thick to get much into my mouth, so I keep stroking him and focus on licking and sucking the fat mushroom head. He is leaking delicious precum like crazy and I suspect he won't last long. I decide better to taste him now and enjoy round two much longer. I speed up my stroking and suck his cock, my cheeks bowing inward, moaning and using my saliva to make everything slick and feel great.

"Oh God, Dianne! You're gonna make..." He doesn't even finish the sentence before I feel his groin contracting and the first jet of cum paint the inside of my mouth. I moan in genuine desire as more and more cum fires out of his beautiful cock. I let it fill my mouth and then pull back, running the rest all over my face, wearing a big grin.

When he finally subsides, I look up at him and open my mouth so he sees the pool of cum threatening to spill out it is so full. I lock onto his eyes, close my mouth, swallow, swallow, swallow, and then show him my empty mouth. His grin is huge.

"We're not done, are we?" I ask, enjoying the taste of his cum still coating my entire mouth. He shakes his head and shows me a little blue pill which he pops in his mouth to dry swallow. I stand, my body brushing his.

"I want to fuck in her bed," I state, suddenly feeling deliciously dirty. He loses a little color but can't refuse me. They'd given us the tour months ago so I walk in the house ahead of him and straight to their bedroom. The room is a bit of a mess though I enjoy seeing Sara's clothes and underwear around. I climb on the bed on all fours and wiggle my ass at Tom.

"See something you like?"

"Oh fuck yeah!"

I laugh and get off the bed and pull close to him. My hands begin to explore him. He has a bit of a Dad Bod but is still fit enough to be very sexy. His hands return the favor, gripping my round ass (which I've worked for a couple years to create!) and eventually to my breasts. He is cautious as he caresses and gropes them.

I slip the shoulders of my one piece swimsuit off to free my breasts. "Don't hold back. I love feeling you touch my breasts." My breast forms have erect nipples. His hands explore and the glue making the edge of the form and my skin disappear works perfectly. I can see in his mind they are real and hell they half feel real to me too. I can't feel his lips around my nipples as he begins to lick and suck them but I nearly can.

It doesn't take long for the little blue pill to kick in and his swollen cock is all mine. I look in their nightstand drawers and luckily find lube. I slather his cock, enjoying the process as much as he is. I'm already lubed as I'd hoped this would happen.

Returning to the bed on all fours, I back up to the edge and bend my shoulders to the bed top, angling my ass up for him. His hands grope and squeeze my full bottom, playfully spanking me before fishing the thong of the swimsuit out of the way. He slips in a finger, surprised as his easily and slick it moves in.

"I'm so wet for you... give me that cock!"

(Stopping so I don't run over the size in one post, to be continued)
 
He lines his log up and I feel the press of the head to my hole and gasp. It feels so huge for a moment I can't imagine it fitting. But Megan has trained my pussy well and I'm a size queen so we have some pretty big dildos. Not this big but close. He gives some pressure and I just focus on how amazing it will feel when he invades my pussy and fills me up. The room is quiet as I slowly relax.

"Ohhh!" we say in unison as the fat head of his lubed cock slips inside me and half the shaft follows in one smooth thrust.

"Oh my god you're huge!!!!" I blurt, eyes closed, feeling every sensation of being stretched, filled, invaded, and gloriously fucked by a real cock. "Gimme all that cock!"

He grips my hips just the way I dream of and starts pumping, working his monster deeper and deeper. I grip the bedspread so I can push back and after a minute, he makes it all the way in. I feel like I'm taking cock up to my stomach he's so big, my ass stretched wide open. I'm in total heaven and my own cock is fully erect in the swimsuit.

The fucking begins and I moan in utter pleasure. He is eager and strong, taking me just like I want to be taken.

We fuck like that for longer than I can keep track of before he turns me over, grabs my ankles, and goes all the way in again with one thrust. My body shakes as he bangs me, my breasts rolling, my eyes half closed. I feel like a total slut and fuckdoll.

Even with the blue pill, he doesn't last forever. He finally yells and stiffens, his balls doing their best to come up with another large load of cum to deposit deep inside me. I moan and sigh in pleasure at the feel of it.

After a minute, he pulls out of me and steps back. I get a flash of inspiration.

"Get on your knees."

His mouth opens then closes. His Viagra cock twitches, still hard, and he slowly kneels in his bedroom. I get off the bed and stand in front of him. I release my cock in front of his face. It is puny compared to his but my whole five inches is very hard now and dripping.

"Isn't this what you really wanted to do to me?" I ask, mischievously.

He opens his mouth to answer and I slide my cock into it. His lips close on it with the instinct of a cocksucker and he goes to work. He's inexperienced and hesitant but eventually is acting like a porn star slobbering and sucking me. After everything, I won't take long either but I try to hold back, just enjoying him on his knees as I look down past my breasts.

"Are you a good cocksucker?" I tease as I fondle his hair and he licks, sucks, and kisses my throbbing cock. He doesn't reply, his motions are all he needs to say.

Remembering various erotica I've read for years, I pull my phone out of my clutch and take pictures of his sucking cock. His eyes go wide but he doesn't stop.

"You're gonna make me come baby," I purr and he gets more enthusiastic. "Swallow every drop of my cum, sweet cocksucker..."

And I erupt. I don't fill his mouth or last like he did but the pleasure washes over my body as a moan, wave after wave of orgasm. Dutifully, he sucks and swallows it all.

Finally, he sits back on his haunches, blinking at what he's just done. I arrange myself.

"Going to take a last dip. Joining me?"
 
Dianne, we miss your and Megan's updates! How are you guys doing? Has the excitement of your new dynamic worn off at all or you just don't share as much with us anymore?
 
Hello eveyone!

I’m Dianne and I joined Lit a few weeks ago. My wife, Megan, is already here and encouraged me to join. I was born male, discovered I was a sissy, fought that for years, got married, and finally dared to confess to my wife what I needed: wear women’s lingerie.

My dear, wonderful, amazing wife responded with empathy and not as much shock as I expected. She later said that it made sense, I’d been subconsciously trying to be discovered since we were dating. It’s taken therapy for us but we’re still together. Her acceptance triggered a huge change for us. She had her own blooming after I convinced her to cuckold me and get the sexual satisfaction she craves. As I wrestled with my obsession with panties and wanting to be a girl sexually, she’d been wrestling with sexual attraction to women as well as men.

While I don’t see sex reassignment surgery in my future, I am trying out living as Dianne when I can which includes here on these forums. I apologize if I act or express myself as a genetic girl but I am exploring my feminine identity and want to inhabit when I can. Not trying to dupe anyone and apologize now in case I cause or allow confusion of what is in my panties. 🙂

So I’d love to meet lovely friends to talk about our sexual selves so please stop by to greet, chat, (and proposition me 🤣) here.

(while I have been working hard for almost two years now to be able to be seen in public as a woman when I wish to, I am not comfortable sharing pictures and will constrain my play to these forums. Appreciate your understanding)

💋💋 Dianne
Greetings, Salutations and a humongous G'day from me. Hope you have an awesome and liberating time here.
 
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