Cissy meats Sissy

I saw him at Macy's buying panties, I approached him and said quietly "I think you'd look cute in the lacy pink boy shorts".
"Oh, they're not for me" he said blushing as he put the panties he was holding back on the shelf.
"Oh really, I bet you're wearing panties right now" I giggled. I could tell by the look on his face I was right. "Why don't you let me help you shop"? I asked.
"You would do that"? he asked smiling at me.
"Sure, we can go to my house after we shop and dress you, if you"d like"? I told him.
"We could do that"? he whispered.
"Sure we can" I assured him.
"I would like that" he said excitedly.
"I'm Cissy, whats your name sweetie"? I asked as we continued to shop.
"I'm Brian" he answered.
"What's your girly name"? I asked .
"I don't have one" he said.
"I spell Cissy with a C" I told him. "Lets call you Sissy too and spell it with a S" I suggested, as we headed for the checkout counter.
"I'd like that" he giggled.
Once we arrived at my house I had Brian strip while I readied a bubble bath and laid out the clothes we had purchased for him. Just as I had suspected we he took off his pants he was wearing a pair of black bikini panties. I showed him how to use a disposable douche before he bathed, I helped him shave his legs, his cock, balls and ass, then his pubic area leaving a landing strip. His chest was hairless, he shaved a small amount of hair from his armpits and he was smooth and ready to dry off and dress. I helped him put on the red panties, bra, and garters he had purchased at Macy's. We completed his outfit with nude nylons and a very short, very tight little black dress.
"You're sooo cute" I giggled as I did his make up for him, "but we need to take care of that bulge in your dress. Kneeling in front of him I pushed his dress up and sliding his panties down allowed his cockette spring out. "You wouldn't want this to stop you from getting your man, some guys are funny about girls having big clitties" I giggled. "We can't hide it when it's sooo hard" I teased then went down on it.
"Oh god Cissy" he moaned quickly unloading in my mouth.
"Yummy" I giggled as I showed him how to tuck. "You're a girl now, the boys won't know unless you tell them.
"I don't understand Cissy"? Sissy replied with a puzzled look on her face.
"Well Sissy, some guys wouldn't let you suck their cocks if they knew you weren't a real girl" I instructed.
"I'm not gay, I don't want to suck guys cocks" she snapped back horrified.
"Oh Sissy there is nothing gay about a girl sucking cock, it doesn't matter weather your a real girl or a tgirl" I told her.
"I think I just want to be a girl for girls" she said.
"That's ok too Sissy" I purred as I pulled her to me and kissed her probing her mouth with my tongue. "That would make us lesbians" I giggled as I pushed backwards causing her to sit on the edge of the bed. Kissing her again I pushed her skirt up and pulled her panties down her legs and over her feet. I slid to the floor between her legs and started to lick her sweet little boypussy until it was sopping wet, I moved back to her cockette that had gotten hard again and started sucking it, as I did I slipped a finger into her pussy.
"Oooooh Cissy" she moaned as I worked my finger in and out in time with my mouth sliding up and down her shaft.
"Is it good for you sweetie"? I cooed sliding a second finger in and rotating them in her, loosening her hole.
"Oh yes" Sissy squealed as I slipped a third finger in before moving back up to her mouth to kiss her again. On my way up I lifted my skirt and slid my panties to the side freeing my clitty, then removing my fingers slid it into Sissy's pussy. "What are you doing Cissy"? Sissy screamed as she did her best to back away from me.
"I'm going to make you a woman" I panted as I buried myself balls deep in her pussy.
"You're a guy, you got a cock" Sissy said in a terrified voice.
"I'm a tgirl and it's my clitty silly, doesn't it feel good in your pussy"? I giggled trying to ease her fear. "Now just relax because Mommy's going to fuck her little girlyboy" I said pumping my clitty in and out of her cute little boypussy.
"Please" she sobbed.
"Oh Sissy you don't have to beg sweetie, Mommy loves fucking her little girlyboy" I purred as I continued to fuck her.
"But I'm not gay" Sissy sobbed.
"Of course not silly you're a lesbian" I giggled, "and besides I can see you like it", her cockette was very hard and danced between us as we fucked.
Sissy moaned loudly " it's soooo good Cissy" as pleasure took over her body and she started to meet my thrusts. I fucked her hard for several minutes then suddenly her cockette started to spew "oh god fuck me" she screamed. as her cum splashed on us.
"Time to become a woman" I breathed in her ear, my clitty pulsing and filling her with my hot cum.
"YES Cissy cum in my pussy" Sissy screamed grabbing my ass cheeks and pulling me deep inside her as I emptied myself into her, then collapsing on top of her we slept.
100% (38/0)
Categories: AnalFetishFirst Time
Posted by cissyneals
4 years ago    Views: 1,358
Comments (9)
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1 month ago
Super hot! Love Shemales!
11 months ago
sooo sweet
1 year ago
great story when can we meet and go to Macy's
1 year ago
Good story
2 years ago
hmmmm i love cross dressing its a rush of adrenaline
2 years ago
i shop on line nowadays for most things, especially lingerie, but i kind of miss the thrill of going into a store's lingerie department.Usually the sales women were very courteous, especially the younger ones, but there were times when they liked to humiliate the sissy. To hear women laughing as i blushed; well, why DO i shop on line? i secretly loved it, even when a woman i knew recognized me.
3 years ago
Macys bold way to get feminine clothes baby. West Hollywood is better more selections for transexuals, but your story was hot and I know that Cissys cum was delicious mmmmm.
4 years ago
sounds like a lot of fun...
4 years ago
Well that was so good it got me all horm=ny had to jack foff to finish the story thanks