r/Sissy•
shoebox777

Omg gotta tell ya

NSFWSissy Achievement!

So I’m older I did oral twice on the same guy about 28 years ago. I’m happily married and everything’s fine. I do wear panties every day and I’ve had a panty fetish since I was like seven so long story short I’ve got tons of thongs wear daily. She knows. She doesn’t know about that dude 28 years ago nor does she know about the brazier or all the sissy stuff Anyway got fully dressed for the first time ever! Dress, wig makeup the whole thing. Everything but shoes ( don’t have any). Talk here all the time to guys and have had a BUnCH of flakes fall through but chatted this one bbc stud up all day. We agree for me to come over ( wife’s gone). I get there and the apt address is residential. I’m like WtF??? Really? Well it’s new area I dunno the maps are off or whatever. I start heading home in about halfway we start talking. I said maybe some other time and he goes well. I can come to you so I said tell you what I’ll just come back. Let’s meet on the corner and you take me in so we got to the corner and he just said hop into my truck young slender good-looking probably a 7 inch package he insisted on a condom so that made me comfortable. I was gonna do it without, but I’m glad he did that.

Anyway that first touch was amazing through the pants. ( I’m really doing this!!!). Pulls it out and condom and I brought lube and just touched it dry and was putting lube on hand to get things going and he’s fully hard! He does condom and I bend over the console and all my dildo practice paid off. He loved it. DT many many times with. No issue. Lotta stroking. I took to it like a duck of water. Anyway, about 810 minutes and he comes and he’s vocal, but the best part of the story is that I was fully dressed, but he didn’t want me to be dressed in case we went into the room. He didn’t want anybody to see keep it down low so I took off the wig and the bra and the breast forms and everything and I’m just in sweats and a T-shirt, but I had my white satin thong under that and white thigh highs so he pulls my pants down when I bend over and he’s playing with my panties. He’s pulling on the waistband. He’s putting his hand in my crack and he’s giving me good spanks with a good handful of ass and it was just amazing. I’m doing what I need to do and he’s finally in the back and it was just Unbelievable. So then I go home and I brought a little vibrator with me and I put it in my panties. It was buzzing my kitty the whole way home I get home and my new anal plug starter kit came in so I put in the smallest one lube everything up real good and I kind of have some problems back there so I have to be careful but I think the smallest ones 1 inch and I just couldn’t seem to get it all the way in, but let’s call it 90% in. While watching a video to show you how to do the training. Meanwhile, in the front is my wife’s magic wand so long story short this was the first orgasm with something in the back and I can’t remember the last time I came so much I mean the sheets were just soaked and here I am setting up another date. Lol

Posted Mar 14, 2026, 6:30 AM UTC

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