How I Became a Total Sissy

I had cross dressed since I was a child and although I tried to suppress it for many years, I always came back to that desire of wearing sexy lingerie, and other women's things. It was a girlfriend named Jeannie, a cute but kind of crazy girl of Japanese descent, who figured the whole thing out and got me to accept myself for what I was. She made me wear her panties, and encouraged me to wear more lingerie, saying it was very sexy. We would have sex while I wore lingerie, and that was all I needed to become a panty boy.

Jeannie had put me in panties and nylons, but now I was going to have my first experience dressing as a full-blown sissy in front of several others, and I didn't really know what to expect. I'd been to gay bars, and had picked up guys who wanted me to give them blow jobs, which I willingly did, but I had never been dressed in anything but panties underneath regular clothing, which the gay guys looked at as almost being normal for a cock sucker.

After months of sucking gay cock, I decided it was time to come out to people as a sissy, but I didn't feel comfortable with people who actually knew me. At least not yet. If I was going to be humiliated, it might as well be in front of complete strangers.

Looking through Craigslist, I found two cross dressers - Sissy Celia and Sissy Misty - who were looking for a third sissy. These two wanted to have a sissy panty boy sex party, and they wanted to bring their wives, Deena and Annette, along with a couple of other girlfriends, to watch their boys pound me, and make videos of the experience.

So on the evening we got together, there I was, hosting, dressed as a totally effeminate sissy in front of six people.

Annette, a pretty blonde about 5' 6" was Misty's wife.

After we were introduced, the first thing she said to me was, "So you're Kristi Sissy, the pathetic panty boy who loves sucking cock." (Giggles from the girls.)

"I am such a pathetic sissy," I replied.

"Well, so's my husband!" she exclaimed, and we all laughed.

"I just love your lingerie," Deena piped in. Deena was Sissy Celia's wife, with brunette hair cut just above the shoulders, and with very large tits. She had a slutty expression that said she was going to enjoy every bit of this.

I couldn't help but blush. I was wearing a pair of very cute pink silk bikini panties, with lacy trim, a tiny bow on the waist band, and ruffles in the back. I had on a short sheer pink nightie with blue trim and ruffled shoulders, and white nylon stockings with blue bows at the top, secured with a white garter belt. I was made up with earrings and bright red lipstick, and my nails were painted the same color. The girls giggled and laughed at me while they pointedly watched my cock rise in my panties and began to throb.

"I feel so sexy wearing frilly, girlie things," I managed to blurt out. "And you all are the first ones to see me dressed like this."

Deena had a look on her face that seemed to say, I would fuck you in a heartbeat, Pantyboy.

"Oh, that is so sweet. And you're such a very sexy sissy," Annette said. "But you are so pathetic!"

I smiled as the girls laughed at me.

Meanwhile, the guys were taking off their pants and shirts, and were dressed in panties and stockings underneath. I walked over to Annette's husband, and smiling at his wife, I began to rub the front of his panties with my left hand, while caressing his back and panty-covered ass with my right. He got hard immediately, and I continued to move my hand up and down his silky panties over his cock.

I pulled down both our panties just enough to free our cocks, (it was nice to see that he was shaved bald like me), and rubbed the heads of the two of them together. He had a lovely slender cock with an upward curve, around eight inches I guessed. Sissy Misty moaned. Did I want him in my ass, or in my mouth?

Watching this, Rachel walked over for a closer look. Rachel, another knock out, had reddish brown curly hair cut fairly short, and a sexy contemptuous smile.

"Are you a sissy faggot?" she asked.

"I like boys and girls," I replied.

"Yeah, I'll just bet," she said. "You look right at home rubbing your two dicks together."

All with that sarcastic smile.

"If you like," I suggested, "I'll lick your clitty before making him cum in my mouth." I was getting more confident in front of them all in my sissy lingerie.

She turned her back, laughing and walked away to set up the video camera.

"Such a sissy faggot," she said.

While Rachel was busy setting up the camera, Janice walked over to me. She was about Annette's height, with dishwater blonde hair that fell down below her shoulders. I could see she wasn't wearing a bra underneath her T shirt, with the logo "I (heart) Oral."

"Don't mind her," she said, smiling. "Rachel really digs sissies...and I do too."

I removed my hand from Sissy Celia's cock, pulled my panties back up and smiled at her.

"And you can definitely lick my clitty before you make that sissy cum in your mouth."

As she said that she began to rub my cock up and down through my panties. I was still hard as a rock and really wanted to cum at her touch. I barely managed to control myself.

"Oooh," she said. "Such a pretty throbbing cock. Mmmm...I just love a cock in panties."

I reached over to the bottom of her shirt, and using both hands, pulled it off over her head. She had lovely B-C cup sized titties, with erect nipples begging me to lick them. So I did.

"Oh, yes Pantyboy...I like that," she said.

I laid her down on the carpet and began to undress her completely while everyone watched. Rachel turned on the camera and began to record. I fumbled a little with the button and zipper of her white short shorts, got them undone, and pulled the shorts down and off. Then I rubbed her camel toe through her white bikini panties. She was already wet. I pulled her panties down, and stared longingly at her shaved cunt, her crack beginning to widen tantalizingly, promising that her labia would open like a morning flower.

I spread her legs open, and crawling between them, placed my lips on her navel. Slowly, kissing and licking, I worked down to her cunt. She had a strong cunt smell, and was dripping her female cum. I licked up the creamy cum from her cunt as I worked up to her clit, relishing her smell.

My tongue found her hoodie, and then the bump inside, and I licked it and sucked it until she started moaning and panting and thrusting her hips into my face. Her labia were fully open now, and suddenly she squirted her cum into my face as I kissed and licked them. But I wouldn't relent, not yet. I made my tongue like a vibrator on her clit, and she was screaming, "Oh, Pantyboy, oh...you sissy Pantyboy!"

I lifted my head and crawled up and placed my cunt cummed lips on hers and put my tongue in her mouth. I pulled my panties down to free my boy clitty, and put it inside her warm wet twat. She gasped, and started thrusting me, her hips slamming mine. I could feel her heart thumping hard against my chest, and realized she was having multiple orgasms.

I knew I had to cum. I pulled out of her twat, and put my cock in her mouth. She turned me over on my back, and making eye contact, began to suck me, rolling her tongue across the head of my cock. I happened to get a glimpse of Rachel watching us, with her blue eyes looking like they were ready to pop out of her head.

Then I exploded. I came hard and Janice took the entire load into her mouth. But she wouldn't stop. She kept sucking and licking, tormenting me, making my cock feel so good it actually hurt. I was moaning and begging her to quit. But she refused.

She made me cum two more times before I got around to the sissies. By then, I was a babbling wreck.

"I just love a mouthful of cum to swallow," she said. "Don't you?"

I was still too wiped out to tell her how much I did.

Twenty minutes or so later, I was partially recovered. Annette and Sissy Misty came over to me as I lay on my back.

"Okay, Pantyboy," she said. "You can fuck a girl, but can you take it in the ass?"

Misty dropped his panties and started lubing his hard dick, while Annette pulled my panties down and took them off. Then Misty got on his knees, spread my legs and put his cock in my asshole as I spread my legs wide, and brought my feet up near my ass to raise my knees. He put it in slowly, until all eight inches were inside me. It hurt at first, but that was over quickly, and I was getting hard again. He didn't thrust hard, he slid in and out slowly and sensually. I had an idea. As he slid out, I would squeeze his cock with my anal sphincter, and as he slid in, I would relax it. He started panting and moaning, in unison with me.

"That's it you sissy panty boy," Annette said with a wide grin. "Fuck my sissy husband good!"

Now Celia was laying beside me, head down toward my cock, with his panties and throbbing cock next to my mouth. I took his cock from his panties and put it in my mouth. I tried to shove my tongue into his cock's eye hole, and he gasped and gave me a taste of pre cum. He started to suck my cock, which was now fully engorged. It was such a feeling to sixty-nine with a sissy, while being fucked by anotherCelia groaned with his lips around my cock as he came in my mouth. I swallowed his load and kept sucking, hoping to drive him nuts. Misty came in my ass about the same time, and I came with him (for the fourth time that evening), straight into Celia's mouth.

The girls all applauded and laughed, as they watched extra cum drip out of our mouths and down our cheeks.

I knew life would never be the same. I was a full-fledged sissy panty boy. A bottom and a cock sucker.