tagTranssexuals & CrossdressersPleasure in the Park

Pleasure in the Park


I'd ridden that ride a thousand times.... But I just kept getting back into that huge queue line.

I was at the local theme park riding the newest addition to the ragtag assembly of attractions, the Master Exploder. It was the craziest coaster I'd ever dared step my foot into. Everyone else loved it just as much as I did; it could take 30 to 45 minutes just to get on the thing.

Little did I know that that queue line was going to give me one of the best experiences of my life.

I was sitting there, reading the newspapers I'd been smart enough to bring to make the wait a little more bearable. It took me a while to notice, but the couple behind me in line had apparently decided to kiss each other deeply every time the line stopped moving. It was getting harder and harder to pay attention to the column I was reading while they were having a go at each other, so I was getting more ticked off at them every time the queue shifted. After the seventh time they'd locked lips, I'd had enough. I spun around and said, "You going to get a room, or are you just waiting for me to join the action?", not at all expecting them to take the latter option. Satisfied I'd proven my point, I turned back around. But before I could get out my article, the girl I'd yelled at spun me around 180 degrees and quickly shoved her warm tongue into my shocked mouth.

I had no idea what to say or how to react. Let me explain: I'm not exactly the model of manliness. I'm 5'8", with no protruding muscles to speak of, and the only hair you could find on me is on my head. So nobody had really just started full-blown kissing me deeply in public. It was quite a surprise for me. My cock soon responded by making a tent in my pants.

After what seemed like forever, she pulled out of my mouth, grabbed my hand with a firm grip and said, "Follow us." I didn't really have much choice, so I did. We soon exited the park and hopped into the couple's car.

As we were heading to wherever they were taking me, I finally noticed some detail about the couple. The guy was everything I ever wished I could be: 6 feet tall, muscular, and full of facial hair. And the girl - drop dead gorgeous. At least 5'6", with five-inch pumps complementing her dark blue skirt, blouse, and opaque-white stockings, with the tops just peeking out underneath the hem of her skirt. I could feel my pre-cum staining the boxers I was wearing.

We finally arrived at a hotel where I was swiftly dragged into a room. I was offered a drink, and I accepted. Everything was a bit blurry after that; I do remember somehow losing my pants and a pleasure-filled blowjob. But I soon passed out.


When I finally came to, it took me a while to figure out where I was. All the memories started flooding back to my head as I sat up... Or, at least attempted to. I soon found that I was both hand- and leg-cuffed to the bed, forced to lie spread-eagle.

"Oh, so Sleeping Beauty finally wakes," a female said with a giggle. I looked toward the source of the voice to find the girl who had seduced me at the theme park.

"Where am I? And why am I tied to the bed?" I asked.

"Oh, silly. You're in Wonderland - or, at least, you will be... Once we're done with your transformation." She giggled again. "I think you'll find your body is already a bit... different."

I looked down at my body. Only, it wasn't my body at all - right there before my eyes were two perky tits concealing a skinnier body, wider hips, and thinner, more feminine legs. The only thing revealing that I was a male was the very erect cock with its purple head begging for attention.

"Holy shit! What did you do to me?!" I panicked. I started struggling more with my restraints, but they wouldn't budge.

She giggled. "Oh, I just gave you some instant hormones to make your body better. You shouldn't struggle like that. You might break something, and then Jack, my hubby, might not be so gentle... Besides, why are you freaking out? Your shaft seems to be telling a different story." She giggled again as she stood up and started stroking my 5 inches. "Oh, and another thing... If your man-pussy is hurting, it's because there's a surprise already inside. But don't worry; you won't be too loose for what's to come." She grinned as she walked out of the room.

She soon came back and unlocked the cuffs from the bed, but left one on my wrist so she could guide me wherever she pleased. "The dressing room is ready for you now, sweetie," She said seductively. She used her free hand to tease my erection even further. "We're going to make you so pretty that you might never want to get out of Wonderland."

I already knew what was going to be behind that door. When I walked in, I found a huge assortment of girl clothes that would rival a name-brand fashion outlet. The girl walked over to the racks and pulled out an Alice in Wonderland dress, frilly sky blue panties and bra, white thigh-high stockings, a garter belt, and some Mary Janes with three-inch heels. She didn't give me a wig; the instant hormones had grown my hair out a considerable distance.

"Now be a good girl and let me dress you up," She said. Once again, nothing else I could do. I stepped into the panties and she pulled them up; they did a fairly good job of hiding my erection. Next, she put on my garter belt and bra, and slowly pulled up the silky opaque stockings. She teased my cock every chance she could with a stroke or a lick. She pulled the Alice dress onto me and put my blonde hair into a silky ponytail. I stepped into the Mary Janes and took a few steps around the room to experiment with my new-found height. She had already done my makeup when I was knocked out. When I caught a glimpse of myself in the mirror, my erection strained even harder to burst free as I saw this beautiful woman staring back at me. I didn't want to admit it, but I was starting to like this; I even liked the heels and how they caused my tight ass to jut out even further.

"Think you might turn some heads, Alice?" She giggled. "Well, you've already turned mine. Come with me." I followed her into the bedroom where I was forced to my knees and blindfolded. "Put your hands behind your back and put your legs together, Alice," She said. I did as I was told. The handcuff still located around my wrist was taken off and I was tied at my wrists and stockinged ankles with some rope, which were then tied to the bedpost. "I bet you'll like this," She said sexily as she forced something into my mouth and locked it around my head. From what my tongue could tell me, it was a plastic cock-binky that consistently shot a warm liquid down my throat. At first I was disgusted, but the hormones -- and my own, secret fantasies -- changed something in me, and I began to suck that thing as hard as I could, being as feminine as possible. I gulped down every drop wholeheartedly. My cock was aching with the need to do the same thing as the binky, only inside of my lovely captor.

Apparently I was concentrating very hard on sucking every drop out of that binky because I didn't hear the footsteps of the person who came to take it out of my mouth. "Ooh, you are one hungry, naughty little girl," my captor giggled. "I hoped you saved some for me."

She took my blindfold off and I gasped. Before me stood my captor, only looking five thousand times more drop-dead gorgeous than she was the last time I'd seen her. She was dressed in a spandex striped pink dress with a pair of cat ears and a frilly cat tail. Her lovely legs were encased in stay-up stockings that were similar to the dress in color and design with a pair of five-inch heels on her feet. I couldn't believe my eyes; it was the Cheshire Cat, sexy-costume style. This was going to be one of the best days of my life.

"The Cheshire Cat always had a thing for Alice," She said with a grin. "Now's her chance to show Alice how much. But first..." She turned to the door to greet the man that had been with her at the theme park, Jack. My face quickly grew warm as I blushed, realizing that he probably knew who I had originally been. "Cheshire Cat brought a partner to help her."

They both walked to where I was tied up and loosed the rope so I could stand up, but left the rope around my ankles and wrists. They picked me up and took me to another room where there was some sort of BDSM contraption. They placed me down on it and locked my wrists and ankles into handcuffs that were welded to the steel plate on the floor that held up the whole thing. Next, they pulled down my panties and locked my still-pulsating cock into its own miniature handcuff. I nearly squealed with pleasure as my balls and shaft reacted to the pressure of the cuff wrapped around them. I couldn't move even if I wanted to.

"Are you ready, Alice? 'Cause Cheshire Cat and her friend are ready to make this the best night of your life," My captor said. A pause. "I asked, are you ready?" She started tapping her stockinged foot, looking very impatient. I finally realized she wanted a response. "Yes, Mistress," I replied, realizing there was no hope getting out of this. I was trapped, and I had to do something that should be utterly repulsive but at the same time was making me so exhilarated with anticipation -- I had to take Jack's cock in me. "Nope -- that's not good enough," she said. "You need to ask for it. Now, Alice, be a good girl and ask Jack to do what both you and he want him to do."

I blushed even more. This is so humiliating... I thought, But hasn't this always been one of my fantasies -- to be dressed up like a woman and taken like one? My girlfriend would never want to do this with me... So why not take the opportunity now? I took a deep breath and said in my best young, innocent girl voice, "Jack, please take me. I want your cock inside of me. I want you to ram my tight ass and fuck my mouth with your shaft. I want to be your and Cheshire Cat's plaything for as long as I am in Wonderland. Please take my cherry."

Without hesitation, Jack went to my rear, unzipped his pants, and hiked up the skirt of my dress to reveal my frilly panties and my virgin ass. He quickly moved the panties out of the way and the woman pulled out the small butt-plug to lube up my tight hole. A jolt of pain shot through my body as he forced his huge cock up my man-pussy, which was quickly replaced by sheer pleasure as he set into a steady rhythm, occasionally giving my prostate something to jump about. Groans escaped my lips as the combination of him fucking my ass hard and my cock unable to move as I was moved along with him brought pre-cum to my shaft's tip. Suddenly, my open mouth was filled with something large, warm and juicy. I looked up to see who was filling my other hole with their cock -- and to my astonishment, the owner of that huge cock was the Cheshire Cat. She was ramming her wonderful body into my face and giving off the sexiest look possible all the while. I was enjoying this way too much to care anyway, so I just closed my eyes in my silent pleasure, a constant rhythm of cocks moving in and out of my holes while mine was spewing my sperm all over my stockings and the steel plate I was kneeling on all fours on. We each came at least two times before Jack and the Cheshire Cat switched positions. Every time they shot their load into me, I gulped down all I could while the rest flowed out of my mouth and down my face. I felt the hot liquid escaping my ass as well, but Cheshire Cat pulled out and ate up all the cum I missed on my face and licked around my man-pussy, keeping the juice from staining my stockings further. After Jack came again, he left the room, and the Cheshire Cat and I were left to wallow in our pool of cum and pleasure.

"I never knew that a cat could fuck so well doggy-style," I said between gasps of ecstasy, "but I'm sure glad I found out."

"This kitty isn't just good for filling holes," She replied, and after cumming again, she pulled out and unlocked the cuffs so I could stand up and stretch my legs before she kneeled on all fours in a similar manner to my earlier position. She pulled up her dress to reveal her lovely ass that was already bare because her panties had found their way around her ankles. "She's good at having hers filled, too."

My cock quickly sprang up again as I lubed her ass and my shaft with some cum I found sprayed all over the floor. She grunted several times as I shoved it into her very tight she-male pussy. Our groans filled the room as we both came a few times. I dutifully licked up the cum dripping from her cock and the drops sprayed on the hardwood floor I hadn't already picked up, and then she did the same for me. As we laid there in a very hot 69, I said, "It's a good thing I'm on vacation; my girlfriend and bud's would probably be wondering where I am right now."

She giggled. "Oh, silly... Why would they wonder? They already know. Where do you think the third part of our trio went off to?"

As I realized with horror what she meant, Jack went to the door and opened it. Outside stood my girlfriend and two of my friends from high school. My girlfriend was dressed up as a very sexy Mad Hatter, and looked as if she'd already had some fun, as her makeup was a little messy and dried cum covered her face. She looked at me and smiled.

"Well, well, well... What have we here? My old roommate from high school has done a very good job of making my boyfriend a lady, don't you think? But it looks as if she's been a very bad girl... Tisk tisk. I guess we'll just have to show her how to really treat her mistresses and their friends. Don't you agree, boys?" She said as my friends dropped their trousers revealing two huge cocks and looking at me devilishly. I gulped, but again my cock told a different story as it sprang to life in another erection.

"Wh-What are you guys doing here?" I asked worriedly. For some reason, I was still talking like a girl.

"Oh, do be quiet," My girlfriend said as she shoved her strap-on dido into my gaping mouth. "We must teach you how to be good, Alice, and we can't do that if you're talking. So I suppose I'll just have to keep your mouth filled like the cock-sucking bitch you are would want as we teach you." The girls giggled as the guys jerked themselves off for a bit, moving towards me and the Cheshire Cat to pleasure themselves with our holes.

The end.... Or is it?

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