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Tranny Gangbang

byStephanieSeymour©

Angie had me on my back on the hotel bed with my legs spread and my ass propped up on a pillow. She was between my thighs and nudging the head of her cock against my bunghole. I reflexively puckered up. Angie smiled and pulled back.

I still couldn't believe what I was doing. This wasn't supposed to be happening. I was a red-blooded, straight, all-American male. Or at least I thought I was. Yet I had allowed a transsexual to talk me into trying anal sex.

It was tough to say no. Angie looked like she had just stepped off the pages of Penthouse magazine. She had an angelic face and devilish double-D tits. Her body was absolutely smooth. Nothing about her looked manly. Except, of course, the 10-inch cock she was ready to shove inside me.

Angie started tapping her prick against my hole, knocking without coming in. Her tits jiggled ever so slightly. Without thinking about it, I gradually relaxed my butt muscles. For a split second, I forgot that I was about to cross a line that no straight man should go near. Angie sensed my defenses going down and pushed herself inside me.

I heard myself say, "Uh!"

An electric charge shot through my body. Goosebumps popped on my arms. Angie began to slowly pump me. My brain could barely process the exhilarating mix of pleasure and pain.

Angie began to pick up the pace. With each thrust, she drilled deeper inside me. The longer the stroke, the more I wanted. I began to moan, not caring whether the couple in the next room heard. Angie was soon burying her prick inside me every time she thrust her hips forward. Her balls slapped off my ass cheeks. My cock had never been so hard.

I saw her jaw drop open open and knew what was happening next. Angie took one more stroke and shot her load into me. I'll never know how much she came, but it felt like a gallon. She hunched over me, dangling her tits in my face as she squeezed out every last drop.

Then she pulled out and flopped on the bed next to me. She was breathless. A thin sheen of sweat glimmered on her forehead in the bedside light.

"Holy fuck," I said.

I could literally feel myself vibrating.

"Look at this," I said.

I held out my hand to show Angie how it shook. She laughed.

"I hope that's a good kind of shaking," she said.

"Oh, yeah," I said. "That was fucking amazing."

"I knew you'd like it," Angie said, "and we're just getting started."

Let me back up for a second. I need to explain how something like this could happen to a guy like me. A guy who played college football, eats his steak rare and pumps ear-drum crushing heavy metal into his headphones while lifting weights.

I was staying in a Marriott about 20 minutes from O'Hare airport in Chicago. My company had a few clients in the area, and my boss wanted me to check on them to make sure they were happy with our products. On my first night in town, I went to a sports bar just off the hotel lobby for dinner. I was watching sports bloopers and licking hot sauce off my fingers when a beautiful, busty blonde seemed to appear out of nowhere and asked to join me.

This kind of thing might happen to other guys, but it was a first for me. I was taken aback.

"Uh..." I said.

"I understand if you want to be left alone," the beautiful blonde said. "It's just that I'm here alone, and my friends don't arrive until tomorrow. I could really use some company."

There was something about her voice I found irresistible. It was huskier than most female voices but still feminine.

"How could I say no?" I asked with a sly smile. "Please, have a seat."

I was in a booth against the wall, and she sat on the other side of the table. We made small talk about where we from, how awful our flights were and how glad we were that we didn't have to visit Chicago in winter. It didn't take Angie long to ask if I had a girlfriend.

"Not really," I said.

"How about a boyfriend?" she asked.

I laughed.

"No," I said. "No boyfriend either. How about you?"

"I've got boyfriends and girlfriends," she said, while putting her hand on top of mine. "And I'm hoping that we can be friends."

A woody started to grow in my jeans.

"Come sit next to me," Angie said. "I want to tell you a secret."

She patted the cushion next to her. Trying to play it cool, I casually slid out of the booth and went over to her side. I sat close enough for our elbows to touch. Angie took my hand and put it up her skirt. No one could see because it was under the table. The place was empty anyway, except for the waitress and bartender.

As my hand glided up her smooth thigh, I waited for my fingers to land on some labia. Suddenly, I was holding a tree trunk.

I'd never thought about what I might do in a situation like this. Surprising myself, I gave a friendly squeeze. It was totally instinctual. If I'd have thought for even a second, I probably would have run.

But I didn't.

"Let's go up to my room," Angie whispered.

So that's how it all started.

The day after she popped my cherry, Angie and I each had our separate schedules to keep, but we made plans to meet later that night. I felt my phone buzz in my pocket around 4:30 p.m. as I weaved through interstate traffic, trying to make it back to the hotel before the worst of rush hour hit.

I fished out the phone and looked at the screen. It was a text from Angie.

"Mind if I bring some friends tonight?" she asked.

My mind raced. Who could these friends be? Would they get in the way? Or did Angie have something unbelievable kinky planned?

Before I could decide, I looked up and saw the brake lights. My heart jumped. Traffic in front of me had come to a standstill, and I was still zipping along at about 70 mph. I stomped on the brakes with both feet. Rubber squealed on the pavement. The rental car stopped with barely an inch to spare before ramming in to the back of a Buick. The driver looked into the rear view and shook his head.

I normally would have flipped him the bird, but my thoughts were elsewhere. While waiting for traffic to move again, I typed "sounds like fun" and hit send.

When I got back to the hotel, I sensed something was odd as I walked through the lobby to the elevator. I couldn't quite put my finger on it and chalked it up to the anticipation of another night with Angie. At the elevator, I hit the up arrow and waited for the doors to open. A beautiful redhead walked up with her suitcase on wheels trailing behind her. She had huge tits under a loose white blouse and long legs sticking out of her tight, black miniskirt. I did my best to check her out without being too obvious.

When the elevator door opened, I stepped aside and said "after you." The voice that came back at me was way deeper than I expected.

"Thank you," the redhead said.

My mind was blown. It seemed impossible. Here was another transsexual who looked as perfect as a female model. We rode up the elevator in awkward silence as two strangers always do. The redhead got off before me. She flashed me a flirty smile on the way out.

Angie sent me a text about two hours later, inviting me to her room, which was two floors down from my room. My heart thumped as I sprayed on cologne and headed out the door.

When I found Angie's room at the end of a hall on the 10th floor, I heard some giggling on the other side of the door and nearly ran. Getting fucked up the ass once could be written off as curiosity. But doing it twice would seem to cross another one of those invisible lines.

"Fuck it," I said.

When I knocked, Angie responded with mock wonderment.

"Whooooo is it?" she asked.

"Pizza delivery guy," I said, joking back.

Angie opened the door wearing a lacy, red bra with matching panties and black high heels. She held the door wide open, making no effort to conceal her nearly naked body in case anyone should pass by.

"I sure hope you brought more than pizza," she said. "'Cause we're fucking horny."

"We?" I asked. "Who is 'we'?"

"Get in here," Angie said.

She grabbed my shirt and pulled me in the room.

As the door slammed shut behind us, I could hardly believe my eyes. Sitting on the edge of the hotel bed was the redhead from the elevator a couple hours earlier. A black-haired beauty wearing a pink string bikini was kissing her neck.

"Meet Ashlee," Angie said.

The redhead waved lazily, clearly gone in a lust haze. I waved back.

"And the girl warming up Ashlee is Amy," Angie said.

Amy detached herself from Ashlee's neck and smiled at me.

"Hi," I said.

"You look shocked," Angie said. "I hope everything is all right."

"Everything is perfect," I said. "I was just wondering if you all had, uh, you know."

"Dicks?" Angie asked. "Are you asking if weall have dicks?"

"Exactly," I said.

"You're going to have to find out the HARD way," Angie said.

She planted a wet kiss on my lips and then shoved me toward Ashlee and Amy. Ashlee, who was still wearing her sexy blouse and skirt, took the cue to stand up. She grabbed hold of my shirt and tore it open. Buttons went flying. The shirt was ruined, and I didn't care.

Ashlee shoved me on to the bed. I fell to my back. Ashlee started sucking my left nipple, while Amy worked the right. Angie watched with a wicked grin.

The nip action was amazing, the best I'd ever had. My cock was poking straight up at the ceiling, making my khaki pants look like a big top circus. I started to moan.

"He's ready to suck," Angie said.

She slid her panties to her ankles and then kicked them to the side. Her prick was already hard. Ashlee and Amy rolled aside. No one had to tell me what to do next.

I slid off the bed and shrugged off my shirt as I knelt in front of Angie. Her dick bounced with the rhythm of her heartbeat. As I opened wide, I tried to remember everything I could from the best blow jobs chicks had been kind enough to give me.

No teeth and lots of eye contact were important. I knew that much. So I looked up and pushed my head forward. My wet lips slid down Angie's pole. As I pulled back, I dragged my tongue along the veined bottom of her cock. I started bobbing my head. With each down stroke, I took more of her schlong into my mouth. But she was so big that I could barely fit half into my gullet without choking.

Angie wasn't satisfied with half of a blow job. She grabbed the back of my head and made me swallow the whole salami. I gagged so hard, I thought my eyeballs were going to pop out of my skull. Angie let me pull my head back, and I inhaled deeply through my nose. But just as quickly, she pushed my head back down again. I quickly adapted, allowing my throat muscles to relax. Angie started fucking my face.

It didn't take long for her eyes to roll back in her head. I knew what was coming, and I braced for it.

The cum shot into my mouth like one tsunami after another. I couldn't hold it all in my mouth. Little streams dribbled out the corners and onto my chin. When Angie squeezed herself dry, she pulled out.

"Don't swallow," she said. "Ashlee wants a taste."

I held the cum in my mouth. Angie stepped aside. Standing behind her were Ashlee and Amy. Both had stripped naked except for high heels while I was sucking Angie. And like Angie, they were both completely feminine, except for their hard cocks.

Ashlee stepped up to me.

"Show me," she said.

I opened wide to give her a look at the jizz pooled in my mouth. She grinned and nodded approvingly.

"Now stand up and kiss me," Ashlee said.

I did as instructed. Ashlee took me into her arms while placing her open mouth over mine. Our tongues played like dolphins swimming in a salty sea. We each swallowed about half.

The cum must have driven her mad because she had a fiery look in her eyes when she broke off the kiss. She suddenly shoved me hard, catching me off guard. I stumbled and landed flat on my back on the bed. Ashlee giggled. The girls swarmed me, all three of them tearing off my shoes, socks, khakis and boxer shorts.

Angie got a pillow to prop up my ass, while Ashlee squeezed a dollop of KY Jelly onto her fingers. I spread my legs and let her lube me up. Ashlee stuck a finger up my ass and started working it back and forth to loosen me up. It didn't take long for me to be ready.

Angie slid in next to me on my right side, while Amy took up position to the left. They each started sucking a nipple as Ashlee lined up her cock with bunghole. She didn't tease me like Angie had when she broke my cherry. Ashlee just slipped it inside me. She gave me all 8.5 inches at once.

"Oh fuck!" I shouted.

These three girls-- two on my nipples and one in my ass-- had found a way to send me into a sexual bliss I never knew existed. A truck could have driven right through the hotel room, and I wouldn't have cared. It was that good.

Ashlee worked herself into a frenzy. Her wild-eyed look let me know that I was hers whether I liked it or not. As she pumped my ass, Ashlee reached down and put one hand on my throat. She slowly tightened her grip. I suddenly found myself unable breathe. I instinctively tried to push her off me, but Angie and Amy kept my arms pinned, even as they sucked my tits.

Everything started to go fuzzy around the edges. I felt myself fading. But just a second before I would have slipped into darkness, Ashlee released her grip. Air rushed into my lungs, just as she blasted her cum into my ass. The sensation was out of this world, like a million fireworks going off in my brain.

I was still catching my breath when Ashlee pulled out.

"My turn," Amy said.

Ashlee and Angie looked at each other with a knowing smile.

"It's Amy's turn," Ashlee said. "You know what that means."

Angie gave a big, exaggerated nod.

"Doggy style," they said in unison.

"Oh, fuck off," Amy said teasingly. "You like it your way, I like it mine."

"You're such a guy," Angie said. "Only guys like it doggy style."

Amy flipped her the bird.

"Suck it," she said.

Angie playfully licked her lips.

"Bring it," she said.

They all giggled, as I rolled over onto my hands and knees.

"I like this one," Amy said. "So obedient."

She slapped my ass cheek hard. Then she spread open my crack with her fingers and dove in head first. Amy licked up Ashlee's cum, which had begun to dribble out of my hole. I was so horny by now that I had to fight from shooting my own, even though no one had touched my cock.

When Amy came up, she got into position behind me with her hands gripping my hips.

"I love sloppy seconds," she said.

Then she plunged her cock inside me. Of the three girls, Amy's prick was the widest. It felt like a lightning bolt shooting up my ass. The electricity leaped up my spine and radiated out to my arms and legs. Even though it was painful, it was a good kind of pain. I now understand what women meant when they say "hurts so good."

Amy went at me with with a passion, taking a long time to pull back and then slamming herself forward again. I could tell she had become extremely worked up while watching her friends fuck me. It didn't take Amy long to cum, probably a couple dozen strokes. She shot with a grunt. I could feel her warm goo filling my insides.

When she pulled out, I noticed for the first time that Angie had positioned herself on her back on the other side of the bed with her ass propped up on a pillow. She was lubing up her bunghole with KY Jelly.

"OK, baby," Angie said to me. "Your turn. You've earned it."

I slid between her thighs. Her hole sucked in my cock like a tractor beam. She took a deep breath as I entered her. It was the first asshole-- male or female-- my cock had ever been inside. I loved how tight it felt. Three pumps inside her velvety love nest was all I got before shooting my load. I had never cum so hard in my life. No exaggeration, I almost passed out.

We all laid together on the bed in silence for a while, basking in the afterglow of kinky group sex. I finally had to ask a question that had been swirling in the back of my brain but finally bubbled to the surface.

"How is it possible that three gorgeous transgender girls could all be at this hotel at once?" I asked.

The girls giggled.

"You really don't know?" Angie asked.

"No," I said.

"Porn convention," she said. "The biggest names in tranny porn are here at this hotel for a three-day convention that starts tomorrow."

My mind went back to the lobby earlier in the day. I finally made sense of the odd sensation I'd had. All the women in the lobby had something vaguely masculine about them. I rolled my eyes.

"Could this week get any weirder?" I asked.

"I don't know," Angie said. "Ever try on one of these?"

She tossed a lacy, black bra onto my face.

"Not yet," I said.

"Maybe you should," Angie said.

"Yeah," I said. "Maybe I should."

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