The Absolutely, Positively True Story of Chrissy, Part 4: Chrissy Goes Shopping

Welcome back, everybody! If you're just now joining us, you should probably start with parts one, two, and three - hard to follow the story if you just jump in in the middle!

So when we last left our heroine (that's me, I'm the heroine of this story), she had just given her first blowjob and swallowed her first load!

'Cause spermies are a girl's best friend

Shortly thereafter I was divorced (yay!) and living on my own. Sadly, she took the box of lingerie with her to her boyfriend's house. *Sigh* What a waste! I sold our house and moved into a great little bachelor pad - 2 bedrooms and because of the location - NO NEIGHBORS!

I slowly began to rebuild my collection of girlie things and living alone without neighbors gave me plenty of time to play dress up.  I ordered mostly online (Thank you, 3wishes.com !!) but eventually I worked up the courage to go lingerie shopping in town, although I always told the clerk it was "for my girlfriend."

If it seems like the same pose over and over again, that's because it is. Sorry. (By the way, the skirt in the third pic was also a gift from Debby...)

Playing dress up was fun, but I yearned for more. One day I was browsing through the local lingerie/sex toy/novelty shop looking for some new outfits when the clerk approached me and asked if I needed help finding anything. I'll never know what came over me but I hesitated for a second and then turned to her:

"Yes, I'm looking for some new lingerie for me. I really like pink but I'm open to anything."

"Oh..." she said. "For, um, you, huh?" She looked me up and down, and my face flushed red. I wanted to climb through the floor. I was only able to manage a slight head nod as I looked at the floor, avoiding eye contact and feeling smaller by the minute.

"Wow," she said. "That's fucking hot. Come with me, babe."

She led me around the store picking out lingerie for me, pulling stuff off of the racks and asking what I thought of it, explaining why she thought it would work for me.

"Here try this on. This will look good on you."

She handed me an outfit that looked like this:

She brushed past me as I stood frozen in place and she unlocked the dressing room.

"Well?" She asked. She giggled and said "C'mon, baby. There isn't anybody here. And if someone walks in I'll knock on the door so you know to stay in there. Now let's get moving."

I hurried into the dressing room and shut the door. My heart raced as I held the lingerie in front of me. Was this happening? Did I really tell another person my secret? And her reaction was unexpected. She was actually cool with it.

I quickly stripped off my boy clothes but left on the pair of pink panties and lace-top thigh highs I was already wearing. I slipped into the lingerie the clerk had picked out for me and I started to fasten the suspenders to the thigh highs. I heard her call out through the door "Let me see you when you're dressed. Then I'll be able to point you in the right direction." I couldn't believe that she wanted me to show her what I was wearing, and I was nervous about someone I knew walking in but my growing erection was a clear sign that I was going to do whatever she told me to do.

When I got the last suspender clasped I cracked the door of the dressing room, peeking out just a tiny bit.

"Well you are a nervous little bunny, aren't you?" she teased as she crossed the store to me. "First time out shopping for yourself? Like, actually, shopping for yourself, and not lying about it being for your girlfriend?"

I nodded and she giggled. "Doesn't it feel better to be honest about it? Isn't this more fun?"

I nodded again and smiled as she swung the dressing room door wide open.

"Let's get a look at you, shall we?" I was exposed to the entire store, which was thankfully still empty, but I could see the door which meant anyone walking in would see me. I was still nervous but the excitement and what I've come to call the "sissy frenzy" - when I'm in sissy mode and Chrissy takes over trying things and taking risks I would normally not - had taken over and in that moment I was willing to be exposed.

The clerk thumbed through the items she had hung up outside of the dressing room and picked out another outfit. "That's good but I think this will be better - try this one on." She handed me another pink outfit to try on and closed the dressing room door.

This outfit left me even more exposed, and when I was done I poked my head out again. She came and examined me like someone shopping for a new car, and then she told me to spin. As I spun around I could feel a slight breeze from the A/C on my very exposed backside.

"Hmmm, I like it, but I think we can do better. Let's put that on the maybe pile. This seems more like your speed." She thrust another outfit into my hands and shut the door.

When I came out she looked me over again. "Yup, this is the one. The pink gingham works well for a sissy like you - innocent yet... trashy." 

We spent almost the next hour with her picking stuff out and me trying it on, and then she'd give me the once over. Other customers came and went (with me hiding in the dressing room). At first I was insanely nervous, but towards the end I was just annoyed every time someone would interrupt my play time! 

I ended up spending WAY more money than I had planned that day, buying several outfits, accessories, and a pair of pink heels. As the clerk was ringing me up I casually asked "Do you guys work on commission?"

"Aw hell no! I wish! No, sweetie, I just enjoy playing dress up with my girlie boys. Have fun with all of your new stuff! You're gonna look totally hot!"

I couldn't get home fast enough to prove her right!

EPILOGUE

So, it's not related, but this happened around the same time so I'm including it here. 

Umm, remember back in part 3 when I told you to remember a certain outfit because it would come back up? Remember? This outfit:

You know where this is going, right?

So...

I'm minding my own business one day and the ex-wife calls. 

Her: "Hey, um so Mike [the ex's new husband] was going through the old computer and found some pictures."

Me: "Okay..."

Her: "Pictures of you..."

Me (still not getting it): "Okay..."

Her: "Pictures of you wearing my blue and white lingerie outfit in the basement."

Me: ...

Her: "That is you, right? There's no face in the pic but it's clearly our basement and it looks like you."

Me: ... 

Her: "Why were you wearing my lingerie and why were you taking pictures?"

Me (My heart is racing and I'm freaking out and I have no idea what to say or how to get out of this...): "Ummm, I was bored..?"

Her: "You were bored? So you put on my lingerie?!?!?"

Me (wanting to scream down the phone that at least someone was finally wearing her lingerie but wanting this awkwardness to end in a hurry): Uh, yes. I was bored. Sorry. I've got to go. 

Her: Uh, ok. Bye?

Me: Bye. *click*

I'd love to tell you we talked about it again and she was secretly turned on and there was a crazy threesome with Mike and all kinds of hot sex but that's not the way life really works. So, my ex-wife has seen me dressed in her lingerie. So has her new husband. Thankfully we don't run into each other very often...