tagTranssexuals & CrossdressersCrossdressing at Pride Ch. 04

Crossdressing at Pride Ch. 04


Sorry for the long delay! But I'm back with another chapter... Please read the other chapters first to know what's going on and as always I love your feedback-don't stop!


I ended up hanging out at Albert's house for more than a week. A week spent trying on as many hot outfits as I could find, from slutty short skirts to gorgeous ball gowns, from tight leather to soft velvet and with all kinds of heels, wigs, jewellery, makeup and - of course - lingerie, to top it off. A personal favourite ensemble was a little black dress with daring mesh panels, a black bob wig, stockings and black leather over-knee boots. My goal was to wow Albert every single time I tried on something new, and I almost always succeeded. New outfits would almost always result in sex. I made him cum several times a day, usually with a hot blowjob and sometimes by letting him fuck me. The latter was something I was careful with, as his large size still made it a little painful for me, so I didn't want to let him do it too often, as hot as I found it.

We also got along very well on a personal level. We shared quite a few interests, such as cooking and photography, and I loved how confident with himself and cultured he was. Despite only meeting him through a weird shared fetish, I was developing some feelings for this guy and I think he was doing the same for me. After a week, though, I felt we were 'running on empty' a little, so I decided to head home for a while. We agreed to meet up again in a few weeks, as Albert also had a business trip to go to during that time. However, before I left, he gave me an extra key to his house, telling me I was welcome to try on any outfits when he was gone.

At home, it felt weird not to walk around in heels at all all day, or to not wear any makeup or hosiery. I honestly missed it. It had become part of who I was. Thus, I snuck over to Albert's house one saturday, just to enjoy my hobby again. First it was time to do some grooming, so I shaved, washed and primped until I was the perfect canvas for my erotic dreams again. Then, it was time to get dressed. Within about an hour, I had figured out a hot outfit: a beautiful black overbust corset and matching thong bustier, under which I wore gorgeous net tights. I checked myself out in the mirror, and realised two things: First-I looked super, super hot. My proudest asset, my well-shaped bubble butt, came out perfectly with net tights over the cheeks and the little g-string in the middle. Second-this was almost the classic 'Plaboy bunny' look. All that was missing was some bunny ears and a white collar. I set up to find it, but no luck. Desperate to get the look right, however, I took off the outfit and cycled to a costume shop, where I luckily did find both as a costume set. I got back, slipped on the outfit again along with shiny black heels, a blonde wig, smokey eyes and bright red nail polish and lipstick.

I checked the mirror again, and I'm pleased to say that I had excelled myself. This was my greatest outfit so far, by a large margin. Albert had to see this. I grabbed my phone to take some pictures, but none of them did the outfit justice; they were both too blurry and the angle was necessarily too awkward to capture it well. I got another idea. I knew Albert had a small photography in his attic, complete with screens and a tripod for his professional-grade camera. I went up there, figured out the camera's self timer and got to posing. I took about a hundred pictures, posing in every way I could think of: standing, sitting on a chair, lying seductively on the floor, front to camera, back to camera... For the last set, I lost my inhibitions completely. I turned my back to the camera, and slowly and seductively took off the corset and let it drop to the ground. Next, I slid down the thong with my butt towards the camera, which kept snapping all the while. Finally, I took off the tights and made a few nice barenaked (but for heels) shots, still with my back to camera.

I put the outfit back on, and got behind my laptop. It took a while to figure out what to send, but I ended up with a nice set of favourites. The opening shot was one of my back facing the camera, hand on hips, butt nicely in view. Then came a couple of nice, vanilla frontal pictures, standing up, sitting down and lying on the floor. The last few pictures were the set of me stripping slowly . I sent the pictures to my phone and then on to Albert one by one via Whatsapp. After the first one, I sent a message: 'Guess who's in your house?? ;)'. I waited for the double-check to know he had received it, which came quickly, followed by the checks turning blue to show that he had seen it. I saw that he was typing a response, but I didn't wait to send more pics. Finally his message arrived: 'Holy shit!!' followed by some lecherous emojis. I then proceeded to send the little striptease set. He took a while to respond to that, then finally his message arrived: 'Want to skype?'.

I turned on Skype and waited for him to call. When his video opened, I could see he was sitting in a nice hotel room, wearing only a bathrobe and looking very hot indeed. We chatted for a little while, but i soon saw that his right arm was moving around quite a lot off-camera.

'You dirty man, are you playing with yourself?' I said. He smiled, then pushed back his laptop so I could see his glorious large cock peeking out through the robe.

'So what if I am?' He asked seductively, 'You got yourself looking this hot, and you're expecting me not to get aroused?'

I giggled. 'Of course not, and thank you...You like it?"

He held his hard cock up to show how much he did. "Why don't you show me a little ass?"

I obligingly turned around on the chair to give him a good view. I shook my butt a little and rubbed it with my hands, then gave myself a playful little slap. Albert's moans and jerking sounds came through the little speakers of my laptop.

"Mmmm... such a great little girl ass... I wish I could grab it right now..."

"Really?" I asked, slapping again. "What would you do with it?"

His jerking motion accelerated. " First I would grab it and rub it because it's all mine".

I felt myself getting hard now, and started to rub against the front of the thong, my butt still to the camera as I sat on my knees on the chair. "And then?"

He jerked harder, then suddenly stopped. "Wait, I have an idea... go downstairs to my bedroom. In my nightstand drawer, there's a little surprise for you.

Excited and curious, I got off the chair and ran down to the bedroom, my heels clicking on the hardwood floors all the way down. I was afraid it wouldn't be obvious what Albert had meant, but when I opened the nightstand drawer it immediately was. There lay before me a large, purple dildo with realistic contours and veins. Ok, interesting... I also found some lube, which I brought with me back up stairs.

I triumphantly shook the big fake dick in front of the camera. "Ahhh... You found it. It's a lifesize replica of mine, I had it made about a year ago just for fun but now we can finally put it to use." His hand moved back to his now half-flaccid member. "That's going to be my surrogate cock while we have a little fun."

I giggled and got down in front of the camera. Holding the dildo upright on the desk, I moved my mouth to the camera and gave the tip a quick, coy kiss.

"Go on... you love sucking my big cock, don't you?"

I flitted the tip of my tongue around his cock head in small, flighty circles. Then, slowly, I ran down the length of the shaft and back up again. My own cock was throbbing, almost snapping out from under the little g-string.

"Why don't you slide it into your mouth?" he suggested, jerking in slow, hard motions. I leaned over and slowly slid it in.

"Mmmm... Yeah... Take that big cock in your mouth, my little blowjob queen..."

I sucked it like it was really him there, my other hand sliding down into my panties to jerk off.

"Suck it... You suck it so well... I wish I had your mouth over my cock so badly..."

I was now hitting a quick rhythm, the rubber cock going deep down into my throat. I was super turned on, the only thing wrong was the chemical taste of the dildo.

"I want to cum in your mouth... Do you want to taste my cum?" I moaned hard in approval.

"My little cock slut... I'm gonna cream in your mouth so soon... Give you all the delicious cum you want..."

He was talking a lot more dirty than he normally did, but I was into it. His dominance was what turned me on most about our lovemaking.

"Wait... " He said. "I wanna see you naked too. Why don't you do a little striptease, like in the pictures?"

I laughed and got up. Removing the chair, I started to dance sexily for the camera, swinging my hips and rubbing my hands over my body. Slowly, I zipped out of the bustier and slid it off whilst still covering my 'breasts' with my arm. I had a little surprise for him as well. After another few little dance moves, I took my arm away and revealed the little black nipple tassles I had found earlier while looking for and outfit, and put on more out of curiosity than anything else.

"Mmmm... nice... I was hoping I'd see those... Now, how about that little thong?"

Turning my back to the camera, I started swinging my hips again and rubbing all over my thighs and butt, before finally grabbing the top of the little G-string and slowly sliding it down. Then I stepped out of the heels before sliding out of the tights. I put the heels back on and fell back into the chair, finally revealing my naked form before my lover.

"So hot... I want to play with your little clit. Why don't you do it for me?"

I slid my hand down and got to work on myself, staring lustily at my man's big dick as I massaged my smallish one.

"Mmm... I want to suck on that juicy little clit... and rub it with these big hands until you cum hard."

I was getting more and more turned on.

"Why don't you play with your pussy as well a little?"

I grabbed the lube and leaked a little on my asshole. I then got to gently massaging it as I continued to stroke my cock. Glad to have shaved and washed well earlier, I then slightly slid in my middle finger.

"Oh god... So hot when you do that..."

I went deeper and deeper, then moved another finger in, then another.

"Mmmm... Now, you didn't make me cum with your mouth yet, so you know what that means..."

I did... I grabbed the big dildo from the desk and turned on the chair again, my ass facing the camera.

"Good girl... You want to get fucked, don't you? You're scared of this big cock, but you still love when it's inside of you, don't you?" I moaned in agreement as I gently pushed the head of the dildo against my hole. He summed it up perfectly, really.

"Now, I'm not there but I'm still going to fuck that little ass hard. And soon, it'll be my real cock inside you again, shooting you full of hot cum."

The dildo slid in, and I started rocking it back and forth gently. My other hand was jerking my cock hard.

"Yess... Deeper... I want all of my cock inside you." He was jerking hard as well. I moved it harder and harder, feeling filled up and slightly uncomfortable but also mega turned on. Finally, I heard a loud cry through the speakers and turned around to see Albert shooting his load all over his stomach. Taking it as the go ahead, I jerked a little harder and also shot all over the chair.

I took the dildo out and cleaned up as we recovered from our earth-shattering orgasms.

"That was incredible..." I said.

"I know... I've had quite a lot of real sex that didn't come close to the fake sex we just did" Again, I couldn't help but agree.

"When are you back?" I asked.

"Wednesday, around 9. When can I see you?"

I giggled. "You'll see me soon enough, don't worry".

I was forming another little plan...

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