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Chapter 23 by Jaylyn28
How do I look in Jenny’s clothes?
Better than I expected
It soaked into everything so shirt, shorts and boxers are all done for the weekend. Looking at the options I find a reasonable baby blue pair of panties. I don’t get any ass coverage as it rides up on me, I find it weird that it fits perfectly on me. Would have assumed some differences between Jenny and myself but when this whole ‘mixup’ was planned from the beginning and the clothes were tailored for me. I didn’t know so I just stood perplexed as I saw my small crotch get hugged by these panties. Hoping a skirt would hide the metal bulge of my chastity cage, I get a simple shirt black skirt. It hugged my form but not too tight to expose anything, that and because the cage was a flat one I didn’t have to worry in the end. Everything was set up in already set outfits so with the skirt was a white band crop top. It felt weird to have this on and weirder how I noticed I was so naturally hairless. You had to look hard for any of the small hairs on my arm and my stomach didn’t have anything.
Head low income back out and say, “sorry for spilling a little of the sauce. Think we will be able to still have a good dish.” I come back and the plates have already been served. On top of that Nathanial snuck in some aphrodisiac **** into my drink that he poured me.
“Hey man it’s all good and damn. It is weird to say this but I got to recognize how you kinda rock this look. Seems Jenny’s fashion works well on you too.” Blushing I rush to sit down. Not knowing what to say I just quickly grab my drink and take a big sip.
“Haha, yeah I guess so. Sorry if seeing me dress up like a girl is weird or I look bad. Not my intended wardrobe.” The taste of the drink is pretty good, a white bubbly wine to pair with the white sauce pasta is really good.
“Hey slow down there. Wait. We aren’t going anywhere so why not. Let’s have some fun and drink what we want.” Filling me back up to full with this spiked wine he sits down and we have our first meal. It is late on Friday with the sun down fully. I can’t see much outside so my focus is naturally pushed towards Nathanial. What makes it so weird for me is I start to notice all of the muscles his arms and shoulder have. Like I have seen his social media posts where he only has a bathing suit on but to be in person across from him at the dinner table is another thing. I find myself… admiring him. His dark smooth skin blends in well with his outfit. Nathanial takes notice of this.
“Hey man, you need to eat some to go with all that wine you are drinking. Plus if you drink me up any more you might get drunk off me as well.” He sounds so natural with this weird semi flirting. Or is he just fully flirting with me? “I am only joking, you can look all you want. And just don’t even think about the clothes you are wearing or think it is weird. You look good and we are just two friends, or well I hope by the end of this weekend we are.” Nathanial pushes the envelope by even pulling off his shirt which floors me. Mouth a little agape and the **** taking full effect I can feel the twinges of pain from the cage keeping me unable to be erect. His chest and body are perfectly molded almost. How he has just enough chest hair without it being overwhelming I catch myself checking out my girlfriend’s ex. I am checking out Nathanial and I can’t stop.
Post dinner fun
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Befriending my girlfriend's Ex
Story of cuckholdry and feminization
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