Something New Ch. 01 - Exploration

I got twisting into a sissy crossdressing fetish from Tumblr back in the day. I used to dress in my wife's lingerie, watch sissy hypno, chat with men. But I needed more. So as a "gag gift" because I totally wasn't serious just joking, I bought a small butt plug.

My wife thought it was hilarious and was so into it all. She even insisted on plugging my ass every time we had sex.

One day I forgot to do laundry for my work clothes and I didn't have any clean underwear but my wife had an idea.

"You can wear some of my panties"

I was in a rush so I was like, "sure whatever." And she brought back what I thought was going to some plain granny panties but no it was red and silky and lacey. I just rolled my eyes.

"That's all I have left..."

We both know that she has a whole drawer of neutral panties. But fine she was doing a bit and I was going to go along with it. So I put them on and got dressed for work and left. When I got home she was all over me and insisted we shower together. And of course she brought the butt plug. But it wasn't the same, this was metal and bigger. Apparently she went out and bought the sizing set. This was the next size up.

"I loved the idea of you wearing my panties all day today. I even played with myself while you were gone. I just had to go out and buy a bigger set. Do you wanna try it out?"

I'm a little nervous, to be honest, but I nod my head. My wife obviously giddy drops to her knees, which she never does, and takes my hardening dick into her mouth while reaching underneath and probing my hole. To my surprise and my wife's glee I am getting hard quickly as she's probing my ass with the medium size butt plug. I feel it stretching me out until it breaks the seal and sucks it right up inside me. I groan and she looks up at me and asks how that feels.

"It's a lot of pressure. Just give me a minute to settle."

"Can you feel it behind your balls? On your g spot." As she knocks on the plug reverberating inside of me.

I nod my head as I shutter and tell her "I don't think I can take the next size just yet."

"How about a bet? If you take the next size up I will let you cum all over my face."

I am shocked she hasn't let me do that since high school. But I dread to hear the catch. She grabs my dick and starts slightly jerking it as she presses her thumb on the jewel of the plug in my ass.

"But, if you can't you have to wear my panties again all day tomorrow and one of the butt plugs"

I mean how could I not take that deal." Alright you're on."

My wife smiles with absolute glee. And grabs the biggest butt plug. Now looking at it closer I'm starting to get nervous again. We get out of the shower and head to the bedroom.

My wife pushes me onto the bed and starts fishing out the plug in my ass. It takes a bit because it's really tight there. I'm still rock hard. I get up on my hands and knees and raise my butt into the air waiting.

I feel more lube being spread on my stretched asshole than I feel it. Something cold pressing against my hole. My wife is pushing and pushing but it's not going in. I try pushing back onto it but it's just so big I can't get all of it. I ask for more lube but it doesn't help.

"Looks like someone is spending another day in panties. And I got just the pair. "

She leans over me and reaches under me and starts milking my hard dick. Then I feel something warm pressing against my hole. It's the medium plug. She's putting it back in while milking my dick. Once she gets it in again she starts pulling it back out.

"I'll make another deal with you, if you wear this plug all day tomorrow and the panties I pick out you can still cum on my face when you get home."

Excited, I nodded my head emphatically. Seeing my agreement she presses the butt plug into my ass and leaves it. Then rolls me over onto my back and mounts me. As she lowers her weight down I feel her tight wet pussy gripping my hard cock and the pressure from the butt plug being pressed deeper into me. She grinds on me and bounces on my prick, thumping the plug into the mattress.

"Can you feel it baby? Can you feel the plug in your ass every time I bounce on you."

I nod my head, unfamiliar with this sensation and realizing that I'm about to cum a lot sooner than I expect.

My wife, noticing my concerns, doubles down and leans over me presenting herself to me for me to take over. I wrap my arms around her and squeeze hearing her moan. As I buck up into her I feel myself clench around the plug in my ass. And it just makes me cum faster.

Realizing I don't have much time I hammer into my wife's tight wet pussy. A grab her ass cheeks and use them as leverage to fuck my wife harder. Then I explode. A combination of squeezing the foreign object in my ass and the warm embrace around my cock. I physically shutter. My wife just lays there on top of me feeling me shoot every last drop of semen into her wet hole.

"I'm sorry baby I couldn't hold it any more"

"Don't worry about it, that was amazing."

She rolls off of me and I waste no time taking the butt plug out of my ass. It was really hard to get out. My asshole squeezed around it like a vice but I finally got it moving and it finally broke the seal and I involuntarily squeezed the rest of it out. I climbed back into bed with my wife and we cuddled up and fell right to sleep.