First Time with a Sissy

"Hey, Paul. You won't believe what I did last night!" My best friend Anthony said with a very big grin on his face. I knew from that grin that I was going to be in for a wild story.

"What?" I grinned.

"Remember how I told you that I wanted to hook up with a crossdresser or sissy?"

I nodded. Anthony had recently told me about his fascination with crossdressers and sissies after he had come across a hot sissy porn video that had completely blew his mind. He shared the video with me and I was surprised at how much I wanted a sissy too!

The video was of a brunette sissy with a big ass who was having sex with a big muscular man. The sissy worshiped the man's cock like it was the last cock on earth! Her mouth moved over every inch of it and she made him come quickly. A big load of cum filled the sissy's mouth and she had opened her mouth to show the camera before swallowing it. The man's cock was still so very hard so the sissy got on all fours and he fucked her. His balls slapped against her as he fucked her hard. The sissy looked at the camera the entire time and moaned in such a sexy way. The man fucked her until he came and when he pulled out of her asshole, there was so much cum that came out with it. It was the hottest video that I had ever seen!

"Well, last night, I downloaded this dating app that is strictly for sissies and men that want to hook up with them," Anthony grinned. "I matched with this sexy sissy named Janet. Look, I'll show you!"

Anthony pulled his phone out of his pocket and showed me the dating app which was called "Sweet Sissies" in pink cursive letters. He brought up the profile of the sissy and my eyes widened. She was very beautiful with a lovely curvy body.

"See! Isn't she hot?"

"Very," I said as Anthony flipped through her pictures in her profile. I could feel my cock getting hard as I looked at her.

"She came over to my place last night after we matched and chatted for a bit." Anthony paused for what I knew was to keep me in suspense.

I laughed. "Come on, man! Go on!"

Anthony laughed and then that big grin came to his lips again. "I swear I had the best sex of my life! Janet got down on her knees right when I opened my door and took my cock out. She sucked me so good that I came in like 30 seconds!"

I listened with rapt attention. My cock was throbbing as I imagined that very hot sexy on her knees sucking Anthony's cock. "And?"

"We both got naked and she had her tiny cock in a chastity cage. It looked so hot that I went down on my knees and licked it," Anthony grinned. "I licked it for a moment and then I moved my mouth to her ass and ate her out!"

"Wow!" I said with wide eyes. "How was it eating her ass?"

"Amazing! Delicious! Every great word you can think of that was how it was!" Anthony said in a loud voice. "I ate her ass until her clitty, which she called her cock, came. There was a few drops of cum that spurted from it. She said that she did never came a lot anymore since putting her clitty in the chastity cage."

"What did you do next?" I asked. My cock was throbbing so much that I could feel precum leaking out from my slit.

"She asked for me to fuck her asshole. She leaned against the kitchen counter and I looked at her ass for a moment. It was so bubbly! When I put my cock in her asshole, I instantly came!"

"No fucking way!" I shouted in surprise. We were both in Anthony's apartment but I was sure that his neighbors were wondering what the hell was all the shouting about.

Anthony laughed. "Yes, way! Her asshole felt so good when I went inside of it that I came again! My cock was still hard though after I fucked her and I swear it was like.... heaven. I fucked her until I came again. I swear I shot a big load of cum in her!"

I stared at my friend with awe and a hint of jealousy. I wanted my own sissy to have sex with! "God, that sounds fucking amazing! I want a sissy too! Right now!"

Anthony grinned. "Let me see if Janet is available tonight and if she has any sissy friends that she can bring with her tonight."

"Oh, you were seeing her again tonight?!"

"Yeah. This time, we were going to take turns eating each other's assholes before fucking."

"You lucky bastard!" I shouted.

Anthony laughed and then began to type in the app. My cock was moving around in my shorts from how excited I was. There was precum continuously leaking out now from it.

"Okay! I told her about you and she said that her friend Millie wants to meet you. They are both going to come over right now," Anthony said.

The largest smile that I had ever smiled spread out across my face from how excited I was. "Yes!" I shouted again. I was going to have my first sexual experience with a sissy!

Janet and Millie arrived thirty minutes later and as soon as I saw Millie my cock bulged in my shorts. She was so very sexy! She had long black hair, light brown eyes, and small cute lips. She was thin but had a nice chest and a round ass. She smiled as she looked at me.

Anthony introduced me to both of them and then he and Janet went to the couch and began to make out. I was amazed at how they didn't waste any time getting to it!

I was a little shy now but when I turned and looked at Millie, she pulled me close to her and kissed me! Her lips were so soft as they pressed against mine. We kissed for a moment before her hands went to my pants and she pulled them down. My hard cock came out and she took in her hand.

"Mmmm!" I moaned as we kept kissing. My hands went to her boobs which was soft before I moved them to her ass. Her cheeks felt so great against my palms that I gave them a gentle squeeze. Millie giggled and then she went down to her knees before me. My heart was beating so fast in my chest as I watched her take my cock in her mouth.

"Fuck!"

Millie began to suck my cock with her lips moving up and down the length of it. I heard moaning from the couch and I saw Anthony eating Janet's ass. She was on all fours on the couch with Anthony behind her with his hands spreading her ass cheeks a part. His mouth moved fast on her asshole.

Millie played with the head of my cock with her tongue which caused so much of my precum to trickle out into her mouth. Her eyes were on me the entire time and I felt so mesmerized by those beautiful brown eyes.

She kept sucking my cock until I could not take anymore and I told her that I wanted to eat her ass before I came. Millie smiled and quickly took off her skirt and I saw that she had a very tiny cock which was erect. She turned around and bent forward with her hands on her ass cheeks. I watched as she spread them a part and my mouth began to water as I looked at her cute pink starfish.

I got down on my knees and quickly put my tongue on her asshole. Millie moaned and spread her cheeks even more. I lapped at her asshole making it so very wet from my saliva.

"Mmmm! Yes, baby!" Millie moaned.

There was a lot of moaning coming from the couch and when I glanced over, I saw that Janet was eating Anthony's asshole with him in the doggy position. Janet's ass crack was wet from Anthony's saliva.

"Oh yes, go deeper, honey!" Millie shouted.

I licked harder and deeper at her asshole. It was so delicious that I wanted more of it. I inched my tongue inside and Millie let out a loud cry. Her body trembled hard and her asshole began to wink against my tongue.

"Fuck! I'm coming!" Millie cried out.

I kept licking at her asshole as it winked hard and long against my tongue. It took a while before she finally stopped coming. When I took my mouth off of her, I saw that pretty asshole was dripping my saliva.

"Oh god! That was amazing!" Millie moaned. "I want to ride your cock!"

I got to my feet and sat on the couch behind Janet who was still tonguing Anthony's asshole. Millie walked toward me and I saw cum dripping from her tiny cock. She had ejaculated from my mouth on her.

"I am going to ride you so good, honey!" She straddled me and then slowly guided my hard throbbing cock into her asshole. We both moaned as I went inside of her. She was quite tight and the pleasure of it was so amazing!

Millie put her hands on the back of the couch and began to bounce up and down on my cock.

"Fuck! You feel so good inside of me, honey!" There was so much pleasure written across this sexy sissy's face. I put my hands on her ass cheeks and gripped them as she rode me.

Next to me, Janet had finished eating Anthony's asshole and was now riding him in reverse cowgirl. She was riding so fast that they both were moaning very loudly.

"Oh yes!" Millie moaned before she leaned down to kiss me. I thrust into her as she bounced on my hard cock. I cold feel my balls beginning to tighten and I knew that I was going to blow my load quite soon. They were filled to the brim with all of my white salty cum.

"You like this, honey?" Millie grinned as she rode me faster.

"Yes! Fuck yes!" I shouted as I thrust faster into her. Her asshole was gripping me so tightly. My balls slapped against her with each thrust into her.

"I am going to come!" I groaned as her ass bounced so fast on my cock.

"Come, honey! Empty those balls for me!" Millie moaned. She was now riding me so very fast.

I heard Anthony cry out as he came inside of Janet's asshole. She moaned and kept riding him fast.

I gripped Millie's cheeks even harder and thrust like a madman into her tight asshole. My balls tightened and then I cried out.

"FUCK!"

My cock twitched inside of Millie's asshole and then started to spurt out my cum. I bucked with each spur. Mille kept riding me fast and I even felt her asshole tighten even more.

"Goddamn!" I shouted and she pulled my head to her chest and held it there. She ground her hips on me as if trying to milk out every drop of my come. I trembled hard and panted against her.

"Yes, honey. Give me all of that come. I want you to fill up my bussy with all of that come!"

Hearing her call her asshole, her bussy made my cock throb so hard inside of her. I was sure that I spurted out a very thick and long rope of cum into her. It took a while before I finally stopped emptying my balls inside of her. I was sure that there was not a single drop of semen in my balls.

I leaned back and looked at her and saw that she smiling down at me. "God, that was amazing!" I said with joy.

Millie kissed me and began to move her hips on me causing my cock to get hard again. "Ready to go again, honey?"

I smiled and spanked her nice round ass cheeks. "Hell yeah!"