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My first time encounter with a ladyboy - sex story


My first time encounter with a ladyboy



I had been eyeing her up across the bar for about 20 mins when she finally noticed me. She flashed me a cheeky grin and I could feel the front of my pants start to tighten. I told the bartender to bring her a drink and when he did she looked over and sucked on the straw in the most suggestive way. I had my suspicions but I still didn't know for sure. She picked up her drink and made her way over to my table, sitting down straight away. Again she flashed me that wicked smile.

"See something you like?" she asked.

"Yes I do," I replied with a smirk of my own.

"Oh really?" she continued. "You are very direct, I like that."

"Well, when I see something I like I go for it!" I said.

"You do know what I am?" she asked with the faintest hint of shyness.

"I wasn't sure," I said, "But I'm glad I was right."

She moved and sat beside me in the booth, her hand instantly dropped between my legs and started rubbing my inner thigh. I sipped my beer and lowered my hand to the top of her mid-thigh length skirt. We both stroked each other's inner thigh and I started to feel the precum leak from my painfully aroused cock. I could tell she was getting just as turned on. She leaned in and whispered in my ear...

"Men's room, now."

With that she stood up and walked away.

My heart was pounding. I stood up and walked to the men's room. When I opened the door she was standing there in a pink frilly bra and matching panties. I closed the door behind me and she started kissing me, probing my mouth with her hot tongue. I undid the button of my pants and released my throbbing cock from its confinement. The head was slick with precum and I was so turned on I knew I wasn't far from orgasm. I stroked my wet cock while she continued to kiss me deeply. She wrapped her hands around my neck and the tip of my cock rubbed against her belly button. Suddenly I felt it coming. Just in time I grabbed the elastic of her pink panties and pulled them towards me. At that moment my orgasm washed over me, and a hot thick jet of cum spurted from my cock and into her panties. I continued to stroke my engorged rod and spurt after spurt of hot sticky cum shot from the tip of my head and into her (by now) very wet pink panties.

As my orgasm subsided I looked down and saw it for the first time. Peeking out from a puddle of my cum was her hard little cock. There was so much cum in her panties it looked like it was floating on a sea of seamen. She was rock hard but still only about 2 inches, a perfect boi cock. I closed her panties and the flood of cum spread and started to drip out and down her legs. Her panties were dripping cum. I started stroking her girly clit through the cummy panties and straight away she started moaning. I could tell it wouldn't take much. I slid a hand down the back of her panties, her ass was wet with my cum. Gently I slid a cum covered finger between her ass cheeks. As I continued to stroke her cock through the moistened fabric the tip of her girly cock peeked out from the waistband of her dripping panties. As I slowly inched my finger into her tight boi pussy she couldn't take any more and erupted with a hot gushing spurt of her own. Her cum shot out of her panties and all over my still hard cock. I continued to work my finger into her pussy. She whimpered the sweetest sounds as hot jets of girl cum bathed my man meat. I could feel the heat from her cum as it washed over my cockhead.

Eventually her orgasm subsided. We stood there dripping in each others cum with our cock heads gently dribbling the last drops of our love juices on each others softening cocks. Slowly she removed her cummy panties and slipped them in my pocket.

"I have an idea for what we can do with these when we get home," she said.

I smiled.

We hopped in a cab and were at her house in 10 mins. As soon as we got in the door she took my hand and led me into the bedroom. She started to take my clothes off and I did the same to her. As soon as we were naked she took the cummy panties from my pocket.

"Your turn," she said.

She bent over and proceeded to put the panties on ME!

"Hmm," I thought. "This could be interesting."

I went along with it and she slid the panties up my legs and eventually put them in place, tucking in my semi-hard erection. I could feel the cum inside the panties basting my cock and it made my erection grow, straining against the moist fabric. I looked down and could see her tiny cock was painfully hard, pointing straight up at me. It looked so sweet and delicious so I dropped to my knees and took it into my mouth. Even though it was rock hard it felt soft in my mouth and I could still taste the traces of her cum on it. I licked around the head and slid her all the way into my moist warm mouth. My own cock had grown fully erect by now and was really straining against the tight panties. The result of this was that the cum within them was spreading further and rubbing all over my tool. While my tongue worked on her cockhead my fingers found her sweet rosebud.

I knew what happened last time I touched her there and I was hoping for a similar response. Wearing cum soaked panties, on my knees, sucking cock, it seemed the only natural thing to do next was swallow a mouthful of cum! However, she had other ideas. As her orgasm approached she pulled me to my feet, and began frantically stroking her girl cock. She pulled the panties open and released an enormous spray of cum into the panties, all over my rock hard cock. Now I knew what she meant by "your turn". Her ejaculate kept coming. For a small girl with a tiny cock, she sure had a lot of cum. She filled the panties, bathing my cock in her warm thick juice. I felt like my cock was going to explode, it was so hard. Having someone cum all over my cock is the most erotic feeling I have ever experienced. Her cum was so thick and hot, it clung to my cock, penetrated under my foreskin and dripped down between my legs. I felt like such a cum slut, and loved it.

When she was done she closed the waistband encasing my throbbing cock in her cum filled panties. She told me to lay on the bed on my stomach. Without hesitation I did as she asked. When I lay down my cock moved in the puddle of cum and rubbed against the fabric of the panties. She straddled me from behind, pulled the panties to one side, lubricated her finger with cum, and inserted it into my ass. I writhed on the bed, pushing back against her finger and forward into the panties and the puddle of cum. I didn't take long for me to reach the orgasm of my life. I thrust my hips back and forward one last time and unleashed a massive load of cum into the flooded panties. Our juices mixed together and leaked out all over the bed. I screamed as jet after jet of cum shot from my cock, I may have blacked out for a second.

When I came around I was lying in a pool of cum, with a soft cock tucked snugly into very cummy panties.

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