First Time With Crossdressers
Introduction:
I discover I’m turned on by crossdressers and search some out in my local area. The night turns out much kinkier than expected, but I learn to love it.
For once, I actually decided to look at some of the other categories on the streaming sites I’d visit. So many things came up under fetish. Some of it I don’t get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn’t my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been dominated, it was always me taking control. The female domination videos were getting me hard for the most part, but at times they were a little extreme. Nobody was shocking my balls!
“What the hell,” I said aloud. “Is that a guy? It has tits.”
Curiosity got the best of me and I clicked the shemale video. What appeared to be a woman with long black hair and large breasts entered the room in only black rubber panties and thigh high boots. She shook her ass in the face of a guy that was sitting on the couch, moving it within an inch of his face. He turned her around and started rubbing the panties. Slowly a bulge grew and it was obvious through the thin material.
“That looks like a fuckin chick. Jesus. Amanda Hart?”
I opened a new tab and looked up more videos of her and I was mesmerized. She was usually in control and feeding her cock to an eager male, though there were a couple of her with another shemale. My cock was throbbing at the site of a woman with a dick.
“Amanda is a girl, she just has a dick. Still has tits and the look of a woman. That’s not too weird I guess.”
I moved the cursor back to my original tab, looking at more fetish videos and saw one involving a crossdresser.
“That’s kind of similar but no tits. Maybe I won’t even like it”
The crossdresser, clearly wearing a red wig, was sitting on a bed with a cigarette dangling from her plump ruby lips. Her hands slid down the vinyl maid outfit until reaching the bottom. She grabbed onto it and lifted it up, revealing a hard cock. The crossdresser started stroking her cock, slow at first, then furiously until she shot a big load of sperm into her gloved palm. It glistened off her vinyl clad fingers. I watched intently as she lifted her fingers to her mouth and licked every bit of cum off of them.
“Shit. I’m hard as rock. She’s very passable, looks like a girl but doesn’t even have boobs. Is this gay?”
Panic set in as my mind raced, thinking about whether or not I was into guys. I couldn’t think of a single guy that I found attractive. It had never even crossed my mind.
“Okay, shit, I’ll just look at some gay porn and see if that does anything.”
After watching a minute of clearly gay males sucking each others dicks, I had my answer. My erection fleeted once the video was playing. Apparently, I just have a strange attraction to shemales and passable crossdressers. It was something new but I wasn’t as freaked out about it. Upon research, a lot of guys are fascinated with shemales but have no interest in sex with other men. It was a relief.
Over the course of a week, I looked all kinds of shemale porn, occasionally enjoying amateur crossdressers having sex. The more I watched it, the more I craved having sex with one. I’d never had a cock anywhere near me other than my own so it was something new, but I wanted to try something different.
There were several shemale personals sites. I found it hard finding a shemale in my local area so I moved onto crossdressers. It seemed more likely that I’d be able to find one of them, and I was right. Within days there were several messages in my inbox. One was a bit of a travel so I wasn’t sure if I wanted to do that. XDress49 was a bit too old for me. The one that really intrigued me was CdLtx. Considering that it would be my first time, you’d think I would have gone with a single person but I couldn’t help but reply back to the couple with the user name CdLtx. They were both 25 and crossdressed regularly. Both Carrie and Ali were incredibly attractive, fairly tall with light brown hair that went past their shoulders. They looked similar but Ali’s hair was curly and she had a couple tattoo’s on her right arm.
“They look really hot. Let’s see what they wrote.” I started reading their message aloud, “My girlfriend and I have been flirting with the idea of having sex with another person. We were intrigued to find out that you had never been with a girly boy before and we would love it if we could be your first. You also mentioned you wanted to try to be the submissive one. That wouldn’t be a problem because we tend to switch, though usually Carrie dominates me. We know where Henson is, we live within 10 minutes. We could come to your place if you would prefer, but it would probably be easier if you came here. To answer your last question, yes we do own several pieces of latex, along with leather and vinyl. It’s okay if you aren’t up for anal as long as you are contributing. Let us know when it would work out best for you, Ali.”
I sat there looking at the screen, excited and a bit nervous. My weekend was free so I emailed them back and let them know. There wasn’t anything going on for them after 4 pm on Saturday. It was set.
When Saturday rolled around I was very anxious. This was something completely new for me. When I arrived at the apartment they were very nice and talked to me like a friend, probably trying to calm me down. It was hard to concentrate considering they were already dressed up for the occasion. Carrie had her hair pulled up tight and she wore a black leather corset with a tight little skirt. I loved her boots, they came up just past her knees. Ali had a vinyl cop outfit on, accompanied by wrist length latex gloves and knee high boots.
“Do you mind if I smoke?” Carrie asked politely.
“Not at all, I actually have a smoking fetish as well.”
“Really,” she smirked as Ali held the lighter to her cigarette, releasing thick smoke into the air.
“Do you like my police uniform,” Ali said as she stood next to me. I nodded my head and then the switch flipped. She grabbed my hair, tugging at it. “Good, not that it matters what you think little boy. Get on your knees.”
I knew it had to start sometime, but I expected a warning. There was little hesitation as I dropped to my knees.
“Good boy. Did you know that I have nothing on under my sexy little vinyl outfit? Nothing under there but my hard cock.”
I stared up at her, noticing a bulge in the vinyl, which made me harder than I already was.
Carrie spoke up, “So the boy likes to watch girls smoking cigarettes? I want you to keep your eyes on me while I take deep drags on this, but don’t you dare forget about Ali.”
Ali looked at her in approval, then back to me with dismay, “Lick my vinyl, right here where my cock is.”
She pressed the outfit against her body so the bulge was even more noticeable. As my tongue swirled around it, it kept pushing out. My eyes stayed focus on Carrie as she exhaled smoke towards me, calling me a little slut.
“Time to lift up the vinyl little slut and take my cock. You like it?”
“Yes, it’s nice and thick.”
“You want it in your mouth? You seem so fucking eager.”
“Yes, I’d love it in my mouth.”
Without hesitation, she shoved her prick into my mouth, slamming the head into the side of my mouth. Her cock rammed at my cheeks as drool slid down my chin. I’ve never had one in my mouth and she wasn’t being gentle. Regardless, I tried as hard as I could to keep up. Carrie walked over behind me, her boots echoing throughout the room. Her hand gripped the back of my head as she shoved me forward, choking on Ali.
“Yeah, keep it up slut boy. I love when they can take a good face fucking.”
It was distracting, trying not to choke on her, but I still found myself extremely hard.
“Carrie, you look like your ready. I see how excited you are. Lift up that skirt for me. Mm, such a nice cock. I think it’s time baby.”
All of a sudden, my pants are being grabbed and ripped off. I don’t think much of it until she takes my boxers off to, demanding I get on all fours. With Ali’s prick in my mouth, I kept yelling out,” No anal! Said no anal!” The girls laughed as I tried to pull my head back. Ali grabbed me by the hair and pulled me forward, sliding every inch down my throat.
“I guess I’ll be nice and spit on his ass since he is an anal virgin. Looks like he is enjoying that blowjob he’s giving, don’t you think Ali?”
Ali laughed, “He is fuckin loving it. Come on baby, put it in him. Fuck his ass hole.”
Spit hit my ass crack and dribbled down to my hole. She slid a finger inside of me, pushing saliva in, which made me jump forward. This isn’t what was expected and I was freaking out. I’d never had anything up there and I certainly wasn’t expecting this to happen. I cried out as Carries cock pushed it’s way inside of me. It didn’t go easily but with a few hard pushes, she was able to thrust deep into my rectum. Tears rolled down my face. The pain was excruciating.
“Mm, this boy has such a tight ass, Ali. I’m going to fill it up too.”
“Lucky boy, he is going to get cream in his ass and mouth. Keep sucking boy, you know you love it.”
Other than the painful entrance, I found myself somewhat enjoying the feel of her dick sliding in and out of me. I said I wanted to be dominated and they weren’t lying when they said they would do it. I had a cock sliding in and out of both ends and my cock was hard as hell, ready to erupt.
“Be a good boy and maybe Ali will give you her golden treat.”
I wasn’t sure what that was but the surprises so far weren’t completely terrible so I stopped fighting as much. Ali pulled out of my mouth, gripped her prick with her gloved hand, slapping it on my tongue. To prove I was willing, I didn’t make her force me, I willingly took the cock into my mouth. It slid down my throat slowly, poking at the back of my throat, making me gag for a moment. She removed her prick and started jerking so I opened my mouth wide, waiting in anticipation for my first cumshot.
“Give him a big load baby. Shoot it in his dirty mouth. I’m getting real close to filling his ass up. This little bitch is going to be full of cum.”
Carrie continued to ram me viciously. Thank god, my ass was starting to get used to it because she wasn’t letting up. Her balls were smacking into me with each thrust as she slapped my ass, digging her nails into me.
“Hey slut boy, you want our cream? You want that cum in your mouth and virgin ass?”
I was so turned on that I really wanted it and replied, “Yes, please. Give it to me.”
Carrie slowed down a bit, thrusting less, but even harder as Ali moaned loudly. I opened my mouth as wide as I could, closing my eyes. Warm splashes hit my face, dripping from my nose while other shots went into my mouth and on my lips. The taste was better than I had imagined it would be. I licked Ali’s cum covered cock clean.
“Mm, so much cum baby. Fuck, I’m ready. Here it come slut boy.”
I was still taking in the moment from the blowjob cumshot when Carrie released a big load of her sperm inside of me. Her thrusts slowed down rapidly as she made sure every last drop was released.
“Well, Carrie, do u think he was good enough for my golden surprise?”
Carrie smiled as she pulled her half hard cock from my anus, “I think he’s earned it.”
“Close your eyes bitch and open wide.”
It was unclear to me what was coming until right before the stream hit me. My mind put the pieces together but it was too late. The hot stream of piss was splashing across my face and dripping down into my mouth. It was shockingly enjoyable. I would have never thought I’d enjoy something as strange as that but it felt so good.
“Good boy,” Ali said as she shook the last droplets into my mouth.
Apparently, I enjoy a lot more things than I thought I would. This opened up my eyes in a whole new way. Perhaps there were other kinky things out there that I had dismissed, but may actually love. Maybe these girls were my gateway to another world.
“Can we do this again,” I pleaded, erect and wanting more.
They looked at each other for a moment, then Ali spoke up, “Can you continue to be obedient? Are you going to keep an open mind? Because you seemed to be more open to kinkier sex than we thought.”
“After this, I think I’d be willing to try anything.”
