Thursday, April 15, 2021

New Pics

 I took some new pics today since I was feeling sexy. Thought I'd share them with you! (Please ignore the mess in the background!)

Monday, December 14, 2020

A Weekend Away, ch 01

 This is a fictional story I started writing for Literotica, and I thought I would share it here. It's in multiple parts so I'll add them as I can.



My wife Tiffany had been hinting for a while about my birthday surprise. She wasn’t great at keeping secrets, and I normally figured out her surprises in advance only to have to act surprised, but this time she was being super cagey. She asked if I would be able to leave work at noon that coming Friday so I figured we were going out of town for the long weekend (Monday was a holiday) – probably to a quaint B&B for a romantic weekend, or maybe even to the city to check out one of the swingers clubs we’d found online.

Ever since I had come out to Tiffany about my desire to crossdress and revealed “Chrissy” to her, our already-good sex life had morphed into another level of hedonistic pleasure. After some time for her to process it, she was supportive of my crossdressing and being a sissy. What started as us fantasizing about what we would do with another man who could dominate and cuckold me while satisfying her desires quickly became a reality. We joined a swingers dating website and began playing with a few couples. I found a couple of men to play dress up for. She found a man to be her “boyfriend.” He wasn’t interested in seeing me dressed up, so she would fuck his brains out and then come home to me.   Some of our hottest lovemaking was when she came home full of his cum - which I would obediently slurp from her dripping pussy - before we fucked like horny teenagers. We had talked about checking out the swingers clubs in the city but had never found the time to make it work. I was hopeful that this was her plan, so I cheerfully took Friday afternoon off from work.

“You got tomorrow afternoon off, right?” Tiffany asked me Thursday morning on my way out the door to work.

“Yeah. Why? What do you have planned?” I asked her.

“None of your business. That’s why it’s called a surprise,” she shot back as she ran her hand over my ass and then rubbed me through the front of my slacks. “You still park in the garage at work, right?”

“Yes. Why?!?”

She pulled closer and whispered in my ear “Don’t. Worry. About it.” She then moaned lightly in my ear and I could feel my cock begin to stir under her touch. Clearly, I would be getting absolutely nothing done at work for the next day and a half, and she giggled knowing she had gotten in my head.

I probed for more details Thursday night, but this woman who wasn’t always great at keeping the surprise was suddenly throwing out confusing details and disinformation liked a trained CIA operative. However, I knew if she was working this hard to keep her secret, that it wasn’t just a romantic getaway at a B&B and had to be the swingers clubs we had so often fantasized about. I spent Friday morning fantasizing and daydreaming about all the naughty things we could get into, what it would be like to see my wife in a writhing, naked ball of humanity and enjoying every minute of it. The time finally came and I’m pretty sure my feet didn’t hit the ground between my office and the exit to the parking garage next door.

I crossed the parking garage towards my car and saw an attractive woman in business attire step out of a black Lincoln Navigator. She looked authoritative but sexy – hair pulled up in a bun, dressed in a black pencil skirt and a white blouse, black nylons and black heels. Her outfit accentuated her curves well without being over-the-top slutty and her glasses added to her air of authority and intelligence.

“Chris.” I thought I heard her call out. I’m not Chris, I thought to myself, but Chris is probably a lucky guy. I continued walking and wondered if maybe I’d see this hot woman – or someone like her - at the swingers club in a few short hours.

“Chrissy.” I heard her call out this time. I might have misunderstood her the first time. Hearing my sissy name called out loud made my heart jump a little but I knew absolutely no one outside of my wife and our few partners knew my secret so I was positive she wasn’t talking to me. I kept walking past her and nodded in an awkward why-are-you-looking-at-me-and-yelling-a-random-woman’s-name way.

“Chrissy!” she yelled and I looked at her over my shoulder. “Yeah, I’m talking to you, sissy.”

My head was swimming and my whole body froze as I heard the s-word. I slowly turned to face her.

“Um, my name’s Greg. I’m not sure who you’re looking for,” I tried to reason as the gears in my brain ground to a halt.

“No,” she said as she walked over to me, “your name is Chrissy, and even with your boy clothes on I can see you’re a little sissy bitch. Now get in the car. You’re wasting my time.”

I stood there looking back and forth between her and the black Navigator, not knowing what to do next. After what seemed like forever the sound of my text alert made me jump and I quickly grabbed my phone to check the message.

You should probably do what she tells you to, CHRISSY. It was from Tiffany. So this – whatever this was – was the surprise. And it appeared they had timed this very well.

I swallowed hard and cycled through all of the possible scenarios in my head.

“Shouldn’t I just follow you? If I leave my car here people will wonder why my car is still here,” I told her, still under the impression I had any say in the matter.

“It’s taken care of. Give me your keys and get in the fucking car. NOW.”

I handed over my keys and started toward the SUV. She followed close behind me and I saw her signal to the SUV out of the corner of my eye. A large muscle-bound man with a large tattoo on his forearm hopped out of the front passenger seat and she threw my keys to him. When I got closer, I could see the tattoo was a 1940s-style pin-up girl – a cute brunette winking back at me as she fell out of her underwear. He opened the rear door and ushered me inside, my new female “friend” climbing in behind me. I watched as the large man closed the door and then walked towards my car, got in, and drove off. I hoped my car insurance would cover him in case he got in an accident, but I was pretty sure I didn’t have random-stranger-involved-in-kidnapping-the-insured coverage. I sat in the middle in the back seat, another very large man seated to my left.

“Go,” the woman commanded the driver and the Navigator pulled out of the parking spot. Then she turned her attention to me. “Look at me.”

I turned towards her and folded my hands in my lap, feeling slightly claustrophobic between her and Cap’n Muscles to my left.

WHACK! When I had turned to her she hauled off and slapped me across the face. I was not expecting that at all, and my head reeled for a moment as I’m pretty sure I saw cartoon stars or birds.

“Don’t ever waste my time or keep me waiting again. Do you understand?” I nodded slightly and even though it didn’t really hurt, my eyes watered a little at the shock of it all. “My name is Sydney. You may call me Mistress Sydney, Mistress, or Ma’am. I understand you have a birthday coming up and this is your present. You will do what you are told to do, and you’re gonna fucking like it, right?”

I nodded again, looking deep into her eyes and seeing that it would be best if I did what I was told.

“I have talked extensively with your wife about what kind of things you like and what your limits are. You will not be given a choice about what happens to you, and there will be no safe words. I own every inch of you until Monday evening. You will be my little sissy bitch to play with as I see fit. If you are ok with that we’ll begin. If not you can get out and go home.”

“But my car is…” I started to sputter when WHACK! She slapped me across the face again.

“Yes or no, sissy?” I couldn’t tell if she was enjoying this or not, but she was certainly serious.

My eyes welled up a little more and I looked at the floor in case I would get another slap for starting to well up. The muscled man sitting next to me grabbed me roughly by the chin and forced me to look her in the eyes. “She’s talking to you,” he grunted.

“Yes,” was all I could muster.

“Yes what, whore?”

“Yes, Mistress Sydney.”

“Yes, Mistress Sydney, what, slut?” She teased.

“Yes, Mistress Sydney. I will be your little sissy bitch.”

“Beg me. Beg me to be my little sissy bitch and maybe I’ll allow it.”

My cheeks grew even redder as I was being humiliated by this dominant woman in front of both the driver and Cap’n Muscles. There was no salvaging any masculinity now and it was probably best to accept I had no control over my situation. My shoulders slumped and the man to my left let go of my chin.

“Please, Mistress Sydney, please, ma’am, please I want to be your little sissy bitch. Please?” My voice went up on the last “please” and I cringed at just how effeminate I sounded.  

Sydney chuckled under her breath. “Of course you do. I knew you were going to be a compliant little sissy whore.” She turned towards the front of the SUV. “Did you get all of that, Tiffany?”

That’s when I heard my wife’s familiar giggle come over the speakers of the SUV. “Oh, yeah. Loud and clear. Happy birthday, and have fun, sweetie! Oh and hey – Sydney – try not to be too rough on my little sissy bitch. You break her you buy her!”

My wife, my new friend Sydney, the driver, and Cap’n Muscles all shared a good laugh and the driver ended the phone call. Holy fuck. Tiffany had heard everything. She had seen me dress up, and she had seen me suck cock, even watched while I got fucked once, but she had never heard me beg for it like that before. She wasn’t great at dominating me because she was never sure exactly how far to push me and it was something she wasn’t comfortable with. I respected that but she knew it was also something I enjoyed. If she couldn’t be the one to do it, at least she apparently liked it when someone else did.

“Well then, now that that’s out of the way, shall we begin?” Sydney purred at me, clearly relishing her role and relaxing into it. She reached into the seat back in front of her and produced a pink fuzzy collar with a little bell attached and a pink leash. Even though I was not resisting, the man to my left held my head with two hands as Sydney slipped the collar around my neck and fastened it. She attached the leash with an ominous CLINK and gave the leash a good tug – pulling me towards her – to make sure it was secure. The man to my left turned my head towards Sydney and she quickly applied bright red lipstick. I caught a glimpse of myself in the rearview mirror, still in my work clothes, with a hot pink fuzzy collar around my neck and bright red lipstick on my lips. I looked – in a word – ridiculous.

I only had a moment to contemplate how silly I looked when Sydney handed the leash to the man on my left and instructed “Be a dear and suck Roger’s cock, will you?” Before I could even begin to process that the man on my left, aka Cap’n Muscles, was named Roger, my neck was yanked down and I found myself staring at the head of his cock. (When had he pulled his cock out? Had his cock been out on display this whole time?)

I started timidly, licking slow circles around the head of his cock. He was only half hard so I was able to wrap my lips around him and get all of him into my mouth. He could tell I was having trouble with access so he unbuttoned his slacks and pulled them down with his boxers. I could feel him getting harder in my mouth and I could feel my own erection growing. Sydney reached into my lap and grabbed my erection, sighing when she did.

“Ah. Is sissy enjoying the cock in her mouth? Makes your clitty hard, doesn’t it?”

“Mmmhmm” was all I could mumble around Roger’s growing cock. As he grew harder I was having trouble fitting him in my mouth.  He wasn’t massive but I was at a bad angle. I think Sydney must have sensed that and pushed me towards the floor. I complied and slid down onto the floor while Roger readjusted to give me a better angle. He grabbed the back of my head and pulled me off of his cock.

“Lick my balls, sissy. Put my balls in your slutty mouth.”

I did as I was told and began to tongue his ballsack. He was mostly shaved but I could feel the rough hairs on his scrotum scrape across my tongue. He jerked his cock and slapped it against my forehead.

“Look at me when you lick my nuts, whore. Look at me and let me know how bad you want my load.”

I was becoming lost in the moment and blurted out, “Yes sir. I want your load, please, please cum for me.”

My desperation elicited a chuckle from Roger and the driver. Roger pulled up on the leash and drove his cock back into my mouth, making me gag. He slipped my leash under his foot and used his foot to put tension on the leash, using it to make me bob up and down on his dick. The little bell on my collar was making an embarrassing jangling sound and I thought I heard the driver humming something, although I couldn’t place the tune.

“Jingle bells, jingle bells, jingle all the way, oh what fun it is to ride with a sissy that’s fucking gay!” the driver sang out and both he and Roger erupted in laughter.

“Dude,” Roger called out, “don’t make me laugh when I’m tryin’ to nut in this little bitch’s mouth. You’re fucking with my rhythm.”

Roger abandoned the leash altogether and grabbed the back of my head, pumping in and out of my mouth, occasionally bottoming out and pinching my nose closed until I struggled for air and my arms flailed helplessly. His grunts intensified and I could tell his orgasm was building. My eyes were watering from all of the gagging, and I realized I was moaning involuntarily.

“Ok, sissy,” Sydney spoke up, “he’s going to cum on your face and you’re going to let him. You’re gonna let him paint your face like the whore that you are. IF you understand me, moan like a little bitch.”

I moaned louder and shook my head up and down as best as I could. Roger tensed and held my head in place as he began to shoot his load. The first few blasts went down my throat but Roger quickly pulled out of my mouth and sprayed the rest of his seed on my face. I closed my eyes and stuck out my tongue getting splashed over my left eye and all over my tongue, chin, and cheeks. When he was done Roger rubbed his cock all over my face, smearing his cum everywhere and getting some into my mouth. For good measure he slapped his dick across my still-red cheek and then slipped it back in my mouth.

“Go ahead, sissy, clean off his cock,” Sydney told me as if she had just told me to unload the dishwasher. I licked the last bits of cum from Roger’s cock, licking up and down the full length of his softening cock and even giving his balls a little bit of attention.

“Wow,” said Roger, “when they go back to lick your balls again that’s when you KNOW they’re a complete whore.”

Roger and the driver laughed again but Sydney was all business.

“Thank Roger, sissy,” Sydney instructed me.

“Thank you, Roger,” I meekly blurted out, avoiding eye contact.

“No, really thank him, and look him in the eyes. Thank him for honoring you with his orgasm. He could have blown his load on a face much prettier and sexier than yours. Thank him for sharing his cum with you.”

My cheeks flushed red but I had a feeling hesitating was only going to make things worse. I turned to him and could feel even more masculinity oozing away as he looked down at me. “Thank you, Roger, for giving me your cum. It was an honor to pleasure you, sir. I hope I satisfied you.”

Roger burst out laughing again, and I got even redder, finally breaking eye contact when I thought that I might actually cry for real, and not just from being slapped or gagged.

“Now sissy, come sit next to me again.” Sydney patted the seat next to her and I did as I was told.  “Look at yourself in the rearview mirror.”

I couldn’t quite bring myself to do it, so Sydney lifted my chin with her finger, holding it there so I could see myself in the rearview mirror. “You see that mess? Smeared lipstick, cum dripping from your chin and drying in your hair. Eyes welled up with tears. Take a long, hard look, sissy. That’s you. That’s the real you that you hide under boy clothes. That’s the real you that’s destined to be a fucktoy for real men. That’s the real you that’s just dying to get out. Well don’t worry, sweetie, Chrissy is going to get to come out this weekend. Just you wait.”

“Yes, Mistress Sydney.”

With that she ran her finger up through a glob of Roger’s jizz on my chin and slid her finger into my mouth. I sucked her finger into my mouth, eager to taste more of Roger’s seed. Eager to accept. Eager to slip further into Chrissy’s world. Eager to submit to this woman I had just met.  

Saturday, June 13, 2020

The Absolutely, Positively True Story of Chrissy, part 5: Chrissy Goes Deeper

This is the story of my sissy journey that got me to where I am now. If you're just now joining the fun, it would be a shame if you missed parts one, two, three, and four.

Part 4 left off after a particularly fun time lingerie shopping (as well as a post-script of getting busted wearing lingerie by my ex-wife and her new husband.) Sometime around part 4 or 5 is when I also started this blog and began making sissy captions.

Shortly after my divorce I started seeing someone. Because of a lot of circumstances, we were off and on (and off and on and...) When we were actually together we were good together (and the sex was amazing!), and when we were broken up I spent more time going down the sissy rabbit hole. My spare bedroom closet began to fill with dresses, and corsets, and costumes, and stockings, and heels, and oops! Chrissy had to spill over into the second spare closet. If any of my friends had been the least bit nosy and opened either closet door my little secret would have quite literally been out of the closet!

Around this time I played around with a little phone sex domination and a couple of escorts who were willing to dress me up in person. I wasn't living as a woman full time (nor did I want to), but any time not spent at work was usually spent dressing up and playing online.

This was one of the favorites!

I still had an account on the BDSM dating website and eventually met Bud. Bud loved sissies and loved to go to the local gloryholes to get sucked off by sissies. Eventually we made plans to meet up... at my place. Like I said, my "bachelor pad" was secluded and private without any neighbors. In retrospect I know what a bad idea it was to invite this stranger to my home, but the thought of being his little sissy bitch overwhelmed my better judgment.

It worked out with our schedules that he was able to come over on a random weekday afternoon. I had taken the day off from work to have enough time to get ready. I shaved my intimate areas, and I shaved the upper parts of my thighs so that I would be hairless except for the part of my legs that would be covered by thigh highs. (I was afraid to shave my legs completely in case someone would notice when I wore shorts.) I did my best to follow an online "pornstar makeup" tutorial (I'm sure I looked ridiculous) and I put on my french maid costume,  a blonde shoulder length wig, black thigh highs with little white bows, and pink high heels.

It was this exact French Maid costume (with pink heels)

Bud found my secluded apartment and texted from the parking lot. "Ready yet, slut?"

"Yes, sir. Come on up."

A moment later there was a knock at the door. My hands trembled as I unlocked it and stood behind the door, using it as a shield. He stepped in and shut the door behind him, leaving me exposed to the relative stranger standing in my living room.

"Nice," he said, looking me up and down. "You are a hot little sissy, aren't you?"

Bud was bald and a little shorter than me normally - with my 5" heels I was much taller. He stepped toward me and grunted a little, clearly enjoying what he was seeing.

He began to grope me, grabbing my ass, running his hand up and down my thighs, and lifting my skirt all while rubbing his crotch through his jeans. I was a piece of meat to him and he was busy inspecting the goods.

"Bend over," he said as he pushed on my shoulder, barely giving me time to comply before he was going to make me do what he demanded. I bent over at the waist, sticking my ass up in the air. He grabbed and squeezed and then put his hands on my hips, grinding his hardening cock against my pantied ass.

"Come here," he said as he pulled me towards the couch. He pulled a digital camera out of his pocket and began to snap pictures, posing me like his own personal sex doll.

When he had all the pics he wanted, he unbuckled his belt, unzipped his fly and let his jeans fall to the floor. His cock was about 6" long and straining against the fabric of his boxers. He took my hand and slid it under his waistband. I wrapped my fingers around his cock and it jumped at my touch. He pulled me closer and leaned it to kiss me. He held the back of my head while his tongue roughly probed my mouth. This was not a romantic kiss but rather his way of laying claim to property, and my clitty grew hard in my panties at the thought of being owned.

He let go of the back of my head and began to push me down. "On your knees, slut. Suck it. Suck my dick, whore." The name calling and manhandling made my head light as I dropped to my knees in front of him. He pulled his cock out over the top of his waistband and pushed it towards my mouth as I got to my knees.

I took his cock in my hand and kissed the head, his precum making my lips slick. I slowly licked the underside of the tip flicking my tongue over the end of it. I then began to lick slow circles around the head as he let a soft moan escape from his mouth. "Mmmm that's it, slut. Tease my cock."

I wrapped my lips around the head of his cock and swirled my tongue around a few times. He put his hand on my head and began to push more of his dick into my mouth. I took it as much as I could like I had practiced so many times with my toys. He slowly pumped in and out of my mouth, telling me what a good little cocksucker I was as he worked more and more of his shaft into my mouth.

"Are you a tease or are you a good cocksucking whore?" he asked as he pulled down his boxers and stepped out of his jeans, leaving him naked from the waist down. My only answer was a moan around his cock as he kept pumping. "Huh? What are you? Say it, bitch." He stopped pumping and pulled his cock out of my mouth, turning my head to face him.

"Tell me what you are."

I hesitated for a second as he stroked himself with one hand and held my head with the other.

"Say it."

"I'm a cocksucking whore."

"Who's cocksucking whore?"

"I'm your cocksucking whore."

"That's right. Now prove it." In one smooth motion he guided his cock back into my mouth and pulled my head down, driving his dick all the way down my throat and pressing my face against his pubic hair. I immediately began to gag and my arms flailed uselessly as I suddenly struggled for air. He pulled all the way out again and as I caught my breath he slammed into my mouth balls deep again, gagging once more.

He pulled back again, leaving just the tip in my mouth.

"Look at me, slut. Look at me while I fuck your face."

I looked up at him only to find out I hadn't noticed him pick his camera back up off the back of the couch. CLICK!

I had been able to hide my face in the other pics he took, but there was no hiding now. He pumped in and out of my mouth, pausing occasionally to take another picture or get a better grip on my head. His groans became louder and his pumping faster. He dropped the camera again so he had both hands free to hold my head.

"Oh, yeah. Fuck yeah, you little slut."

He had to be getting close.

"Oh shit. I've got a big load for you - been saving up for days."

All I could do was moan my approval and shake my head yes as this stranger's balls bounced off of my chin.

"Fuck! Yes! Ah FUCK!"

He stopped fucking my mouth and held my head in a death grip as I felt the first wave splash on my tongue and down my throat. He continued to pump load after load of hot cum into my mouth and as hard as I tried I couldn't keep up. His cum ran down my chin and neck and made the fabric of my maid uniform stick to my chest. When he was done emptying his balls into his little cocksucker he pulled out and smeared the cum on my chin around my face with his cock. I finished swallowing what was in my mouth and started to wipe the cum from my face and neck.

"What the fuck are you doing? I put my cum there for a reason. Leave it. You got any beer?"

"Um, yes, sir."

"Then go get me a beer, slut," he demanded as he spanked me on the ass and collapsed on the couch. I assumed I would just give him a blowjob and he would leave but it appeared he was staying for a while. I brought him a beer and he told me to sit next to him on the couch. I sat down and he let his hands roam all over me. As he drank his beer he stroked my clitty through the fabric of my panties and continued to eye me like a piece of meat.

After 15 minutes or so, he very bluntly demanded "Lick my balls."

I paused. Dressing up in lingerie and pretending to be a girl was fun. I even enjoyed giving this man a blowjob and liked the feel of his cock in my mouth. But I had never signed up for licking anyone's hairy balls. Just... ewww... no. The thought had never even crossed my mind.

He pushed me to my knees again as he stood up over me, stroking his cock. He held my head again as he stroked his cock and lowered his balls onto my face. They had a slightly musky odor - not dirty, but also not fresh from the shower.

I wanted to tell him no but he was clearly in charge. I took one and then the other into my mouth while he stroked himself over me. This was a part of being a sissy that I truly didn't like, but the fact that I was completely submissive and not in control was also a huge turn-on. Soon he was hard again and had me alternating between sucking his balls and sucking his dick.

He worked faster this time, stroking hard and fast while I licked and sucked his balls. He slid into my mouth again and began to drive his cock into my throat, making me gag and getting his cock sloppy wet with my saliva. As his pumps, strokes, and grunts became more desperate he pulled out of mouth and stroked his cock over my face.

"Oh, shit. You ready for this, slut? I'm gonna paint your face. Beg for it. Beg me to cum on your pretty little sissy face."

"Yes, sir. Please cum on my face."

"What do you want, whore? Tell me want you want."

"I want you to cum on my face. Please."

"Louder, slut. What do you want?"

After years of jerking off to porn and always fantasizing about giving some hot girl a facial, the realization that I was about to get a facial broke something in my brain. I didn't just want this, I craved it down deep inside and had to have it. I was willing to do anything for this.

"Please please please. PLEASE cum on my face. Please, sir, please."

The wanton urgency in my voice must have done the trick because he began to unload all over my face.

"Please, sir, I want your cum. I want it on my face. Please, please cum on my face."

When he had finished unloading, he pressed his cock to my lips and I licked the last bits of cum from the head, gently sucking to get every last bit of his cum. Then I let it fall out my mouth and onto my chin.

"Damn, you really are a whore, aren't you?" he chuckled as he got dressed. I stood up to see him out the door, and he grabbed my ass one last time. "Next time, I'm gonna fuck that little sissy ass, understand?"

"Yes, sir."

He left, and this time, instead of even attempting to clean up, I left his cum right where it was. I looked in the mirror and looking back at me was a trashy used whore. I liked what I saw.

Tuesday, May 7, 2019

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 onetwo, 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, !!) 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!


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?


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...

Saturday, May 4, 2019

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.


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.