Thursday, August 7, 2008


Get ready, bitch

I had met a lady online named Anna. She was a little older than me and lived in a Nashville, which is about five hours from where I live. She was part of a group that did a little swinging, and while she had encountered other sissies online, she'd never really met any in person, and she was a little intrigued by it. We talked on the phone a couple times, and I told her some of the things I did. She thought it was pretty funny and she wanted to meet me so I made plans to visit.

Once I checked into a hotel and got acquainted with Anna for awhile, I checked into local adult entertainment in the phone book. I've utilized the services of escort girls to come to my room and engage in some sissy humiliation sessions with me before, and we thought it might be fun if I had one come over to do a session with Anna present to just watch. I called one of the services and told them I was a crossdresser looking for some light domination. A woman named Kathy called me back and I told her I had a female friend who just wanted to watch while she dominated me. We agreed on a price, and she headed over.

I showed Anna some of my sissy outfits and modeled some of them while she giggled at me and called me a "sissy cunt" in her sweet southern voice. I was dressed in my bra, pantyhose and high heels when Kathy knocked on the door. I covered myself and let her in. Kathy was very pretty and very nice and professional. We worked out some financial issues, I explained exactly what it was I wanted, and she called in to the service to check in.

Kathy was wearing a skirt with pantyhose and no panties as I requested. I was behind her peeking up her skirt, and Anna was sitting in the corner, giggling, calling me a naughty boy. About that time, Kathy hung up the phone and turned around, catching me. "What the hell are you doing? Get up! What are you doing in these clothes?" I was still smiling, looking over at Anna and her giggling."

She got serious

Kathy grabbed my face and pointed it at hers. She was quite serious. "I asked you, what - are - you - doing - in - these - clothes?" Her voice was stern but she didn't yell.

I was like a little boy caught being naughty. "I... just... wanted... to see what... they felt like?"

Now she lowered her voice in a more intense kind of quiet, almost a whisper. "Oh you did? You wanted to feel what it was like to be a girl? Is that it? You want to be a girl?"

"No, I just wanted to feel the clothes..." I tried to explain.

She quickly grabbed me hard by the wrist. "I'll give you something to feel, little girl. C'mere"

She marched me over to the bed, sat down, quickly yanked my pantyhose down, and pulled me over her lap. Then she started smacking my bottom... HARD!

Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack!

"Owwww!" I tried to put my hand over my bottom.

She quietly and sternly commanded, "Put your hand down."

She started it up again. Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! She would alternate from cheek to cheek.

"Please!" I whined, "I promise to be good!" I again tried to cover my bottom."

"I said put your hand down. Now!"

Again and again we went through this. Anna later told me she couldn't believe how red my bottom had become. I'd never been spanked this hard.

Change of clothes

"Now get up!" she said quickly, "Get those clothes off! Now!" Again, she never yelled, but it was clear she was in charge. I took off my heels, pantyhose, and bra. I was rubbing my bottom with both hands. She again grabbed me by the wrist and marched me across the room.

"You wanna be a fuckin' girl? Let's make you into a fuckin' girl and you can really see what it feels like."

I protested that I had learned my lesson and I didn't want to do it. Kathy told me to shut up while she put a black padded bra and thong panty on me. Next came a black, boned waist cincher with garter. Then she had me sit on the edge of the bed while she put black stockings on my legs. The whole time she was telling me what a hot girl I'd make and how I evidently like wearing girls clothes or I wouldn't have such a hardon. I tried to deny it, whimpering like a pussy boy.

Finally she put my 5" stiletto patent leather pumps on me and had me stand. I stood and covered my bra with crossed arms like a woman would if she had been suddenly discovered undressed. This infuriated Kathy, "Put your hands down! You wanna be a girl. Let's see you be a fuckin' girl. Walk around for us, bitch. " I minced and teetered around the room.

Kathy looked over at Anna. "What do you think? Do you think he likes being a girl?"

Anna came back with a wicked smile, "He's a sissy cunt!"

"He IS a sissy cunt!" Kathy answered. "Now I'm going to spank you again."

"Nooooo!" I whined.

Round two

Again, Kathy grabbed me by the wrist like a child and pulled me across the room, sat down and put me back across her lap. I was already smarting from the first assault on my red ass, and I didn't think I could tolerate much more. Before she even started, I was trying to cover my bottom. She repeatedly ordered me to put my hands down as she started over and over. It only made it worse. Kathy spanked and spanked harder than the first time. It hurt like hell.

I looked over helplessly at Anna, "Please help me. Make her stop!"

Anna, snapped back, "Shut up, you fuckin' bitch!"

And now, your mouth

Kathy grabbed my 10" dildo with balls and held it in front of me. "Now you can see what's it like to suck cock."

"No! I won't!" I pouted.

Kathy answered, "You want me to spank you again?"

I looked over at Anna and reluctantly put my hand on the dick and started licking it. Anna just started laughing, "I don't believe this! You are a fuckin' sissy cocksucker!"

Kathy pushed my head on the dildo and had me bobbing up and down on it as she degraded me. She had me lick the balls and lick up and down the shaft. I was stroking myself as I did. "You really like that, dontcha bitch?" I just quietly sucked the big cock while Anna laughed.

And now, your sissy ass

With that, Kathy took the butt plug laying on the bed and started squirting it with KY jelly and told me to turn over on the bed.

"Oh, please don't do this. I'm really sorry. Please! I won't do it anymore!" I pleaded with her.

Anna jumped in, "He wishes he was a real woman so he could take a real dick inside him."

"I do not!" I answered back like a baby brother. Kathy again told me calmly to turn over as she held the greased up plug in her hand. I begged her not to fuck my pussy.

I continued to beg Kathy as she turned me over. I was now facing Anna who had a menacing smile on her face, and I was now being overcome with humiliation. Anna was going to get to see the look on my face as I was going to get ass fucked. As Kathy slathered the plug up and down my crack with cold KY, I got a disgusted look on my face. Anna laughed and asked in her cute southern voice, "Are ya gettin' your pussy buttered up, hun'? I just let out a disgusted moan.

With that Kathy just jabbed the plug up my ass. She was not at all gentle, and it HURT like hell! I protested, and she told me to be quiet while she jabbed me again. I tried to reposition, and Anna asked me if I was getting my cherry popped. Finally Kathy got it in me and started stroking it in me quickly. She got me up on all fours so I could continue wanking with the dildo in my mouth. Anna just laughed, "I do NOT believe this!"

They were talking to each other and calling me a sissy cunt. I wimpered like one while Anna just laughed. She'd never seen such a display and was truly enjoying the show. By this time, Kathy had called Anna over and was standing next to us. At one point, she was given the dildo to push in and out of my mouth. I think she rather enjoyed the control of fucking a man in the mouth with a big cock and humiliating him in this way.

A little cuckold, just for good measure

At one point, I was wanking and looking at Kathy's pussy through her pantyhose, a view I particularly love. She stared at me back and said, "Look at it!" Then she pulled her pantyhose down. "Go ahead! Look at it! Wank your little dick and look at it! You will NEVER fuck it because I don't fuck sissy boys."

Anna chimed in and said, "He wouldn't be able to do much with what he's got anyway!"

Kathy contined her comments to me, "Yeah, but get a good look at it and wank your little dick, sissy cunt! Sissy cunt! Sissy cunt!"

By now they both kept calling me "sissy cunt" over and over again in unison. It was very belittling and humiliating.

It wasn't too long before I had gotten so worked up that I was about to lose it. "I need to cum," I whined. Kathy sassed back, "Awww, she needs to cum." She took the dildo and held it in front of me. "You know what you have to do then, don't you? You have to cum on this big cock and then you have to lick it clean for us."

"NO!" I whined back like a sissy.

"Then you don't cum. It's as simple as that. You want to cum, you have to cum on the dildo and lick it clean for us, you understand? Are you going to lick it up for us or not? It's your choice. You can cum or not cum, but that's the only way you're going to cum. Don't stop stroking it, sissy cunt! Girls have to eat cum, and you want to be a girl, so you have to eat cum!

Anna was laughing and coaxing me, "Come on, sissy cunt. Shoot your little dick and lick it up."

Kathy was holding the dildo out in front of me. The butt plug was burning in my sore pussy bottom. I couldn't hold it out any longer. I screamed out like a little bitch as I bounced up and down on the butt plug.

Anna reacted, "Oh my god, will you listen to this? He even cums like a girl."

I came and screamed and came and whimpered and came some more. I shot all my sissy cum all over the big hard rubber dick being held out in front of me.

"Did you get it all out, sissy cunt?" Kathy asked.

"Yes," I whined.

She quickly put the dick in my mouth. "Clean it up! Now!"

Anna was laughing again, "Look at this! What a fuckin' cum eating bitch!"

You missed some

I dutifully licked it all up and sucked the dildo clean. I wanted to be a good girl for them and show them I could do it. I slurped the length of it and sucked it completely. By the time I had finished licking it clean that aversion to eating cum started to sink in combined with the shame and humiliation. I looked at Anna who pointed to a big glob of cum on the sheets and said, "You missed some." I let out a moan of disgust. She laughed hysterically as I starting licking it up off the sheets.

Kathy said to me in a motherly tone, "Mama's proud of you 'cause you ate all the cum. You did a good job like good girl." Then her tone of voice changed back into more of a warning, "But every time you put those clothes on, you're gonna get fucked in the ass, and you're gonna have to eat the cum again. You understand, Sissy?"

I nodded in total shame.

Kathy was getting dressed and told me what fun the session was. Anna said she'd never seen anything like this, but she'd learned a few things.

So had I.


Anonymous said...

Wow, Kathy seems to be a very good experienced Domme, or is that usually the standard?


Little Pantyboy said...

Oh, she knew exactly what she was doing. When she left, she said to both of us, "You should let me dominate both of you COMPLETELY sometime." We weren't sure what she meant by that, but we got the impression that this session was leaning toward vanilla by her standards.

Anonymous said...

yet another great story :D

I'm assuming the session didn't quite exactly urhmm cure you of wearing more sissy clothes again eh?

So what next??

trannyslut said...

I fully agree with you !!

Anonymous said...

Sup, fag? Keep sucking cock, you dirty little whore.

I will choke you and force you to suck my manly dick. Then I will cum all over your stupid little faggot face.

Sissies suck the cocks of real men like me.

Anonymous said...

Loved the story I'm a cock sucking sissy just line you and need to be put in my place on my knees in front of a domme woman or real man with a big cock. Ill do anything and everything I'm told. I wanna be made into a real girl and do all that a girl does. Any takers? Let me know

Anonymous said...

Yes im ready u.ur submissive bitch slave is ready for a sissy fag/slave im in i will do anything. U tell me to do

Samantha e.

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