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...

The Absolutely, Positively True Story of Chrissy, Part 3: Chrissy Makes New Friends

If you're just now joining our story, here are links to Part 1 and Part 2 of the story.  Those will get you caught up to this part of the story.

When we last left our story, I was in a failing marriage but discovering my true sissy self.  Holy crap has a lot changed since then...   Sorry.  Getting ahead of myself.  Where are my manners?

So this went on for a little while.  The wife would go out and I'd play dress up.  I'd dress up in the lingerie and slutty outfits I had bought for her and rush down to the computer to pretend to be a whore for random men online. It was around this time that I picked the name "Chrissy" for my sissy self. I liked the way "Sissy Chrissy" sounded and I figured that there probably aren't a whole lot of CEOs, scientists, and doctors who go by Chrissy, but there are definitely strippers, trophy wives, and bimbos that do. I got so into my role as "Chrissy" that I even took some pics of myself in my wife's lingerie and shared them with a few select men online. I felt so fucking hot. I remember one of the outfits I took pics in looked like this:

Remember this outfit - it will come up later...

Pretty soon the pretend wasn't enough.  I signed up for an online BDSM dating site and started chatting with a married couple about 30 minutes away.  (In my defense, at this point I had twice busted my wife lying to me about her whereabouts and had pretty much figured out she was shacking up with someone.)

I would mostly chat mundane things (the weather, politics, pets, etc.) with the wife Debby (not her real name) but I would chat all kinds of trashy sex stuff with the husband (Dave - also not his real name.) Debby and I talked about going lingerie shopping together but Dave's hard and fast rule for people they met online was there had to be a face to face meeting with both of them - kind of a getting to know you thing. Since I was still married it just didn't seem right so we all agreed that maybe it would happen "some day" and left it at that.

A few weeks later, for my birthday, my wife moved out and moved in with her boyfriend. Thanks, honey. (See, I told you she was messing around behind my back.) She took most of the stuff she wanted but thankfully for me - her lingerie box wasn't part of that.

Seriously though - I had ALL of the lingerie!

I now had all of the lingerie, the panties, the thigh highs, etc. and all of the uninterrupted free time a sissy could want. I spent every last free moment in the basement, dressed up and playing online, desperate to try it in real life.

I reached out to Dave and Debby and we set up a time to meet. I packed a bag of all of my favorite lingerie pieces and drove the 30 minutes to their house. I was very nervous but also insanely excited. I was almost hoping we would get to dressing up and playing immediately but Dave very gently made it clear that he was in control and if I wanted to play I had to do it by his rules. We sat at their dining room table, having a few drinks and just chit-chatting about every random thing as my duffel bag of lingerie sat in the corner screaming to me to be worn.

After several drinks and what seemed like an eternity Dave turned to me and said "Well, I see you brought a bag. Why don't you be a good lil sissy and go try on some outfits for us?" No one had ever called me a sissy before and it took me back a little. I tried to reply but the best I could muster was a weak head nod. My face went flush as I crossed the room to my bag. I picked up my bag and brought it to the kitchen table.

"Here?" I asked.

"Not here, sissy. I want to see the whole package all at once. Debby will show you to the bathroom."

I followed Debby to the bathroom. She flipped on the light and as she turned to go she smiled at me and let loose of a little giggle. I quickly stripped out of my boy clothes and slipped into my cute "Lil Miss Muffet" outfit. It didn't reveal much but I was nervous and the thigh high stockings showed off my legs beautifully.

I stepped awkwardly out of the bathroom, trying hard to walk like a girl in my wife's clear plastic stripper heels. (Excuse me... MY clear plastic stripper heels.) Debby was the first to see me.

"Awww. Sissy. That is just too cute on you."

I was able to stammer out a "Thank you" as my head was reeling. These were the first two people to ever see me dressed as a woman. I had feared laughter or ridicule but Debby's reaction started to put me at ease.

Dave looked me up and down and motioned for me to spin around. I did my best twirl for him and Debby giggled again. He then told me to bend over, giving him a full view of my white lace panties.

"Hmmm. Nice. What's next?"

I went back to the bathroom and put on my white see through panties and top with red accents and matching ankle socks. I felt VERY exposed but I figured if they were going to laugh at me (or worse hurt me) they would have done it by now.

No, I did NOT fill it out like she does.

Debby smiled. "That's fucking hot, baby." I twirled for Dave and even did a little dance for him, hoping he'd like what he saw. "Fucking hot is right, babe. Let's see what else you've got, sissy."

I went back to the bathroom again. This time I put on a pink lingerie set with attached garters. My very hard cock strained against the fabric of the panties and I did my best to tuck it in. 

Over the top of that I put on a schoolgirl outfit because, well why not?!?  I spotted some of Debby's perfume on the counter and thought I might as well so I sprayed a little on me. If I felt sexy before now I felt downright electric.

I went back out to the dining room, twirled for Dave and bent over for him to examine my sissy ass and panties without being told.

What happened next was completely unexpected. Maybe I should have seen it coming, but I really didn't. After taking his time looking me over Dave simply said "Come here."

I walked over to him slowly and stood next to him. He ran his hand up the back of my thigh and lightly caressed my mostly-exposed ass. I jumped at the sensation of his rough man hands on my ass. 

"Was this really happening?" I thought. I briefly considered fleeing to the bathroom, grabbing my boy clothes and running out of there as fast as I could. Debby sat back in her chair and took a long sip of wine, clearly enjoying her man feeling up their new play toy. Her relaxed attitude calmed me a little although I stayed rooted to the spot.

"Sit," was all Dave said as he spread his legs and patted his thigh. I froze in place, until he wrapped his arm around my naked waist, swung me around his leg and plopped me into his lap. He drew me closer and I could feel his growing erection rubbing against my upper thigh. He leaned in and smelled my neck. "Seems like someone been's trying your perfume, Debby. Makes me just as horny as when you wear it..." I looked over at Debby, feeling guilty for stealing her perfume but she just smiled and nodded approvingly. 

"I'm sure she smells wonderful," Debby cooed, as she raised a hand to her breast and touched herself through the fabric of her blouse. 

Dave ran his hand over the tops of my thigh highs, probing further up my leg, past bare skin until he landed on the fabric of my panties. "Seems like someone is pretty excited over here," he laughed as he lightly ran his fingers over the tip of my very hard cock. I jumped again but didn't pull away.

My head was in a daze as I took stock of my situation: Here I was, in a stranger's house that I had only met in person an hour or two earlier, wearing thigh highs, heels, lingerie, and a schoolgirl outfit, sitting on the stranger's lap, feeling his cock press against me with his wife calmly sitting across the table sipping wine and playing with her tits. ALL of this was wrong. This was not how straight, still-technically married men behaved. 

And yet, I was euphoric. It seemed so wrong but it felt so right. I decided to just go with the night and see where it took me. 

I wish I could now tell you about all the crazy sex we had that night, about how much I learned and how Dave took my sissy virginity right there on the dining room table. Sadly, this is not Penthouse forum and they received a phone call right then - their recently-moved-out 21-year old son was on his way and would be there in 15 minutes. Playtime was over.

I sprang up to get dressed. Debby stopped me. "Hold on a second - I have an old pair of jeans that don't fit me anymore that would probably look fantastic on that tight little ass of yours."

Debby came back a few minutes later and told me to try them on. I took off the schoolgirl skirt and tried on the jeans. They fit perfect and my ass did look fantastic. "Can I borrow these, Debby?"

"Shit, sweetie, you can keep 'em! Sorry to end our night like this!" Debby kissed me on the cheek and then hurried me back to the bathroom. I kept the jeans on (as well as the lingerie underneath) and put my button-up shirt on over my lingerie top. I quickly packed my bag and got ready to go. 

Debby gave me another kiss on the cheek and hugged me good-bye. I turned towards Dave, knowing that a handshake was probably not in the cards, but honestly having no idea what came next. He stepped in, wrapped his big arm around my waist and almost lifted me off of the floor. He smiled and then kissed me. One hand slid down to grope my ass while the other held the back of my head. I don't know if I could have struggled free from him as he roughly shoved his tongue past my lips. All I know is that I didn't want to. We were not kissing. I was BEING kissed, by a REAL man, and it was clear that I belonged to him. I submitted, and melted into his arms, letting him - if only for a brief moment - have his way with me.

"Until next time, sissy. Until next time." He set me down and handed me my bag. I turned and left.

EPILOGUE

Ok, so I know that wasn't a very sexy ending but that isn't exactly where my night ended. Obviously I was VERY horny at this point and on my way home I thought I'd check out the local strip club. At the time this particular club had a peep show booth where you could watch a girl get naked and masturbate if you wanted to. I figured that or maybe a lap dance would help me work out my frustration with how my night ended with Dave and Debby. 

When I got there (still wearing women's jeans and lingerie under them) I saw there was an adult theater. "Hmm... porn on the big screen? Maybe that will do the trick," I thought. I paid my $5 and went in.  

The room was very dark and "theater" was an exaggeration. There were 3 rows of love seats and a big TV hanging on the wall of a fairly small room. There was one older man sitting in the second row on the right. Other than that the room was empty. I sat in the back row on the left, and the older man briefly glanced over his shoulder at me before turning back to the TV. I watched the movie for a few minutes before I realized the man was masturbating. Suddenly, I was intrigued. 

Very similar to this...

I undid the top 3 buttons on my shirt in the hopes that if he turned around again he'd see my lingerie top. Never looked at me. I made a big show of taking off my shirt completely. Nothing. It wasn't until I moved to the aisle seat of the second row and pulled down my jeans to expose my lingerie, garters, and thigh highs did he notice. 

He looked over as I rubbed myself through my panties. He was now watching me as much as he was watching the TV. I decided to put on a show for him, rubbing myself, arching my back, and grinding my ass into the vinyl seat of the love seat. He seemed to be waiting for an invitation so I smiled at him and nodded my head.

That was all the invitation he needed because he was on me in a flash. He stood in the aisle next to me still clumsily stroking himself. He began pushing on my shoulders until I knew what he wanted. I dropped down to my knees until I was at eye level. With another man's cock. 

He hastily shoved it into my mouth, not leaving any room for the subtle nuance of easing into my first blowjob. Ever. His 4" cock wasn't much to write home about but I could feel him getting harder in my mouth. He began pumping quickly, basically masturbating his cock using my mouth instead of his hand. He held the back of my head and pumped faster. For the umpteenth time that night I tried to process just exactly what was going on, and how it was such a departure from what I had expected. Here I was, girls' jeans around my ankles, kneeling on a hard concrete floor in thigh highs and lingerie, with a stranger furiously fucking my mouth. 

His pumping paused briefly and then - just as fast as he'd put it in my mouth, he pulled out. In one smooth motion he put his cock away, pulled up his pants, and scurried out the door. I was stunned to be honest, that I was so bad at sucking cock that he had felt the need to leave that fast. All of my talk online had been just that and I was not an amazing cocksucking whore. 

I got up and sat back on one of the love seats, leaving my jeans around my ankles, my lingerie exposed to anyone who might come in. I watched the pornstar on the big screen take a facial as the cum ran down onto her huge fake tits and just then - truly no more than 15 seconds after Mr. Fast & Furious had bolted out of the room -  I noticed it. A salty and acrid taste in my mouth that had not been there before. 

And it dawned on me: that older man, my first official blowjob, had shot his load in my mouth. He didn't cum much, and he didn't drown me in it like you hear about, but he had emptied what was left in his balls in my mouth. I had given my first blowjob, and I had made my first cock cum. I swished around what little bit was left of his cum in my mouth, trying to savor the taste and the moment. But I had done it - regardless of anything else that happened or didn't happen in my sissy journey I was officially a cum-guzzling, cocksucking sissy. And I fucking LOVED IT! 

And yes, just for good measure, I swallowed what was left in my mouth.