Spanking

Your thoughts are interrupted by Jordan snapping his fingers. "Come on stand up, lets see how you look."

You comply with the order, standing up you walk over to the full length mirror in your room, seeing yourself you are shocked. 'I look like a sissy version of how Jill did hers for prom, She called it a cottagecore-Glam mash-up, she was so proud of this look. Shit, she made him get this as tattoo'd semi-permanent? How did I not notice that, I thought he was just experimenting.', Eyelashes long and curled, your eye liner is winged, eye shadow is blue with a white star on each lid, lip gloss making your lips pouty, and foundation matching skin tone, all topped off with blush making your cheek bones more pronounced.

"Now you look like the pathetic sissy you are. Just like how I looked." Jordan takes a picture of you before leading you back to the bed and making you sit down again. "Now for your final punishment." Jordan seems hesitant but steels himself before speaking again, "Its a simple thing but I think it will have the emasculating effect I want and take the fight right out of you. But I want to hear your reactions when it happens."

He pulls out a small rope, with what looks like a beads in the middle, it gets wrapped around the dolls head, you can feel your mouth being **** open. It stays like that, 'This must be what a ball gag feels like.'

He snaps his finger and you can make sound again but with your mouth stuck like this it only comes out as "GGMGMMGNN"

The doll is then flipped over onto its back in legs dangling off he left and as he winds his right hand back.

The vertigo is insane for a second as you feel both like you sitting up and bend over a hard surface, before resolving into you only feeling and seeing from the dolls perspective. "GGGGHHH" It was still your human mouth that made noise.

"Cry out for me darling, I want to hear you as I make sure you learned your lesson."

*SMACK

"GGGGGGHHHHHH"

*SMACK

"GGGGGGHHHHH"

This continued for what felt like hours, every few minutes he would stop and run a hand through your hair, whispering, "I know pet, it hurts, I don't like doing it to you, but you won't learn if i go easy on you." and other sweet nothings until your tears stopped.

*SMACK

"GGGGGGHHHHH"

*SMACK

"GGGGGGHHHHH"

It repeated in that pattern until it finally stopped, when your cries turned into moans.

You had gotten home around 11am, by the sun it had to be late afternoon.

You don't know if Jordan did something else to you or if your mind just had enough and broke, but the pain had turned into pleasure, even more so when he started to massage the sore area through the doll.

On some level of your mind you noted that at the very least here, you associated pleasure with pain and both with Jordan.

"OOGHGOHHH"

You let out your loudest moan, that's when he stopped.

Jordan sat you up facing him. Eyes still seeing from the doll. "See that's a good girl, took the fight right out of you. Now lets get you cleaned up and ready for your reward, I almost didn't want to give it to you, but you did the Salon&Spa without any complaint despite your actual discomfort so I think the punishment plus modifying the reward should be fine, I'm a merciful mistress, aren't I?"

He looks at you expectantly.

"UUUHMMMM" You moan, trying to make a sound somewhere in the ballpark of, 'Yes Ma'am".

"There we are. You can learn. I was going to do this in the bathroom so you didn't have a mess to clean up, but I think that cleaning up after this will be good for your character."

He puts the doll in his shirt and snaps his fingers, if he had breasts it would be between his cleavage. It feels warm like a hug for a second before your back in your body fully.

"Take your panties off and lay on you back."

You do what your told, fully cowed by this point but still scared of what was to come.

As you should be. Jordan pulls a strap-on out of his bag. "Did you know, oh who am I asking, you're 'mister oblivious to my friends suffering'. Well, back during one of the times you and her had broken up, I tried to move past you but Jill decided she wasn't done with the fun. Remember how I'm actually bi? Well she acted like she was going to date me, let me take her out and then back to my place, where she degraded me so much for not being you, I couldn't get it up, then decided if I couldn't get her off she would take care of us."

You couldn't describe how horrifying that was to hear and your body was locked in place as he got the strap on secure to himself and climbed on the bed ready to mount you. Only thing you could do is attempt and fail to cry out.

"She did to me what I'm about to do to you. All the while she would talk about how this strap-on was the same size as you, and how much she missed your cock, and how sorry she felt for me having given up on you that I would never feel it. She just so happened to pull out a pic she had on her phone of you without a shirt, brought her face next to mine and whispering how she was going to miss laying on it, my face unable to look away as she fucked me to her orgasm, while looking at you, she made me cum like that. She left my house right after, saying it was a great night but she didn't feel like we could work out, 'turns out I'm not into sissy, i mean femboy, bottoms'. SHE left me with a strap-on in my ass and covered in my own cum, and feeling like a failure as a man, as a boyfriend, and even as a femboy. I was a mess and after crying and cleaning myself up, I blamed myself."

Jordan had the toy at your hole but hadn't added any lube, you screamed as loud as you could, hoping to remind him.

He pulled the doll back out of his non-existent cleavage, took a mini lube packet and squirted the whole thing into the doll's rear.

You immediately felt full and like there was fluid leaking out of you, then he licked the doll before saying a word your mind wouldn't record, and your cock was raging hard again like the other day. A second later Jordan slammed home.

Your screams echoed in your bedroom as Jordan relentlessly assaulted your prostate.

You were getting closer and closer to cumming, that's when Jordan started working you into a new position, you couldn't fight him and any which way he put your body the muscles would work to keep you there.

"I bet you never figured out why Jill kept breaking up with you, at least besides fucking with me, I was a side project really."

By the time he had you where he wanted, your cock was pointed directly at your own face.

"It was because she wanted to hook up with other guys, but didn't want to lose face, so she blew an argument or whatever out of proportion, broke up, started fucking the guy or let him pay for stuff, what ever she wanted to use him for, then let it be heard through the grape vine she might take you back is you tried hard enough, see you were already like me, we were both in her eyes unsuspecting bitch's to be used, you a cuck and me a sissy."

You didn't last long, even with everything you were feeling from what he told you.

"GGGGGHHH" you felt emotionally and physically empty but he kept going, making sure every drop was milked out of you.

A lot got in your mouth and with how you were locked in place you only option was to swallow it, trying to spit it out just made you ****.

You tried to beg for mercy but with your mouth held open and the sounds you could make muffled, you don't know how he understood.

"I'm not done with you yet, you still need to know what its like to be used, remember how Jill would call you her puppy? Well I'm your mistress now, and you are going to be my pet till I say otherwise."

He continues fucking you for over an hour making you cum again, before unbuckling the strap-on and leaving it in you before finally letting your body lay down full on the bed.

"You're welcome for your reward pet, now lay back as I get mine."

Somehow you're still rock hard when he takes off his bottom and panties, showing a cute chastity cage, before climbing on top of you.

"I waited so long for this pet. Try to enjoy it."

With that Jordan lowers himself onto your cock, moaning as he goes.

Its tight and hot, you are helpless to resist, your body doesn't listen to you.

Despite how sore you are and how empty you feel, your body tries to build up an orgasm.

He rides you like Jill did when she wanted to treat you, except with his faster bouncing rhythm and how his cage is pressing against your abs, he's enjoying it more.

Your body tried to cum but all that happened was the contraction of muscles and pain like a cramp.

When he came he let out a squeal and collapsed on your chest. His cum dribbling onto you."MMMmmhmmm pet you are amazing."

After catching his breath and getting up, and starts to collect his thing, but leaving the strap-on in you. "I'd love to stay and cuddle but that would lessen the lesson. Maybe next time if you're good enough I'll stay with you after, but that's for good girls not bad boys" he calls while heading to the bathroom. Its not long before you hear him leave the house.

Your mind is a confused mess. The state he left you in was not helping.

After what feels like eternity of laying there, covered in cum, strap-on in your ass and silently crying, some minor relief comes.

Your body relaxes and you are finally free to move again. Your emotions are running wild, the emptiness and humiliation Jordan described was there, but so was a bit of warmth, a longing for more affection, and a sense of knowing he was in charge and a warm feeling thinking about him. That last one was the most confusing part. 'I should hate him, I am straight, I am straight, I SHOULD HATE HIM, I AM STRAIGHT!'

A insidious part of your mind had a response for that. 'If you had paid attention this wouldn't have happened, if you knew your girlfriend like you thought you did you could have caught her...' It went on and on about how it could be your fault. 'And maybe I am straight but letting him enjoy me is the least I can do right, besides you liked part of it, even if only a little.'

Repeating the mantra turns into a self hate spiral while you clean up everything, the first step of withdrawing the strap-on and feeling the invisible lube flood out onto the bed leaves you crying harder than you have in awhile.

You try to push away the shame and false pleasure that were **** on you.

You fail to do so and they harden into a knot of self blame and fearful guilty pleasure.

It takes forever to clean while crying but Finally its all clean or in the wash, aching you pass out from exhaustion, tears still falling down your face and light sobs shake your body as you grab, and white knuckle hold, your spare pillow for some semblance of emotional warmth.

When you wake up its dark out, your stomach growls reminding you it had been awhile since you ate. Getting up is painful, both emotionally and physically. Walking hurts but you manage to get to the kitchen, grabbing food, and returning to your room. 'Can't deal with the family right now.'

Looking at the flowers Jordan gave you earlier, you start to cry again, 'I've never been given flowers, heck I've never been given anything buy someone I've been with, Its so thoughtful.'

A second later that insidious part of your mind, that's growing stronger, adds 'I didn't deserve this. It may have been mostly Jill's fault but it was my responsibility to fix it now and I've been fighting the closure he needs every step of the way.'

Laying back down with your food you start to nibble, knowing you should eat but the idea less appealing with those last few thoughts.

'Maybe I can fix one small thing right now.'

You grab your phone, checking for any messages.

Seeing none you text Brit. -Hey Brit thanks again for all your help today.-send

PIng*-Anytime hunny, you sounded freaked out when Jordan and I talked, is everything ok?-

Its late but thankfully she responded fast. -Yeah just nerves, was embarrassed, by the time I got home I felt silly and Jordan took care of it.- send

-That's OK hun, I know its scary, especially for guys, you two make such a cute couple.- send

-Yeah he is adorable, hes really sweet.- send,

'Its mostly a lie but I think it will make them both the most happy.'

You don't know how Jordan knows everything that happens but you just assume he's somehow also reading your conversations.

PIng*-OMG, I know right, If I wasn't ace, I would have snatched on or both of you up, I'm so happy for you two! Hes been crushing on you for years, always said you were worth waiting for.-

-Really, I had no idea.-

PIng*-yeah he asked me for advice and I told him to go for it, I know Jill hurt you both but to see you both healing, Its a big step for a boyfriend to go through all this just so they know what their partner has been through, I'm so proud of you. Jordan has been crazy about you. You should have seen how happy he was when he told me you and him were a thing.

'It wasn't true before but it is now, I want to give him closure. Then we both can move on.'

-I bet, and yeah it is a lot more than I thought I signed up for but I'll see it through. Again thanks and goodnight

Ping*-Night.

With that done you felt a little better but still like a piece of garbage, but you were finally able to fall back asleep, tears gone but still clutching the spare pillow for dear life.

♥Chapters are posted early on my Patreon, normally two chapters ahead or more over there, Link in Bio. It also has the most recent updates for the game I'm working on. ♥

♥Newly added is Feminization support it you want to become a Femboy, Sissy, or any other flavor of fem.♥

♥I also stream under the name Gemini_Kiss and make NSFW captions on reddit (username gothdreams) and the patreon discord.♥