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Kaye - My First Pride

"I go to my first Pride event and have my first experience with a trans woman."

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Competition Entry: Pride

I glanced at my reflection in the mirror as I left the flat. I was wearing khaki shorts, a red t-shirt and a grey hoody. I tidied my short, brown hair and slung my camera bag over my shoulder. It was a bright, clear day, so I grabbed my sunglasses and headed out into the sunshine.

I was single again, but instead of moping around, I had decided to get out, try new things and generally try to make the most of the summer. Today, I was going to Pride for the first time, hoping to get some good photos of the parade. It was mid-July and, while there were a few clouds in the sky and a light breeze, it was still hot enough that the hoody came off and got stuffed into my bag almost immediately.

I made my way down the high street, where people were already setting up camp for the parade. At one point, a cute Asian guy with colourful patterns painted across his smooth, bare chest, put a rainbow scarf around my neck and kissed me on the cheek. Now, I had always considered myself to be straight. I’m an open-minded person, don’t get me wrong, but I had never really been attracted to any male friends or celebrities growing up. Recently, however, I’d found myself more open to exploring some unfamiliar fantasies and urges, and that young man caused a few of those urges to stir within me at that moment. Unfortunately, he disappeared into the crowd to continue handing out scarves and I didn’t see him again.

Eventually, I found a spot on some stairs that would give me a good view of the parade.

“Nice camera,” said a voice. I turned to see a young woman with shoulder length blonde hair standing next to me.

“Thanks,” I said. She was also clutching a camera; an older, more battered-looking one than mine. She was about five-foot-seven, wearing large sunglasses, a red and white tank top, denim shorts, knee-high rainbow socks and purple shoes. Oh, and she had also had a run-in with the cute guy with the scarves. We exchanged the usual awkward small-talk as we waited for the parade to start.

“My name is Kaitlyn,” she said. “My friends call me Kaye.”

“My friends call me Sam,” I said. “’cause that’s my name,” I finished, lamely. She laughed and I couldn’t help but notice that she had a very cute smile.

“Have you been to Pride before?” she asked.

“No, this is my first time,” I admitted. “You?”

“This is my third,” she said. She explained that some of her friends were in the parade and she was meeting them later on. “Mind if I tag along with you until then?” she asked.

“Sure, I could do with a guide,” I said. “So,” I said, cautiously, after a while, “if it’s not too cheeky a question to ask…”

“You’re wondering why I’m here?” she said, a hint of accusation in her voice. “You assume because I come to Pride that I must be gay or something?” I floundered for a while before she took pity on me. “It’s OK,” she said smiling. “I just like winding people up. If you must know, I’m trans.”

“Really?” I said, my voice full of genuine surprise.

“Does that bother you?” she asked.

“No, not at all,” I said, “I just… I… I never would have guessed...” I floundered again.

“It’s OK, I’ll take it as a compliment,” she said, sticking her tongue out in an adorable way. “That’s not something I normally blurt out to people I’ve just met, by the way,” she went on, “but if I can’t be honest about it today, of all days, when can I?” It would turn out that there was another very good reason why she wanted to tell me this fact before the conversation got any further, but we’ll get to that later!

We continued to chat as the parade went past and we both took loads of pictures. There were so many people from so many different backgrounds. Some had their faces painted, others had dyed their hair. Some wore outfits adorned with balloons and scarves. Lots of them carried rainbow flags, some of which bore the logos of local businesses large and small. Kaye pointed out her friends, who were in the marching band from a local army regiment.

Of course, I know the history of Pride; how and why it all got started. There were a handful of banners with phrases like “Remember Stonewall” on them. And I know there is still a lot of ignorance, intolerance and prejudice out there, but on that day I didn’t see any animosity; no protestors, no acts of hatred or aggression. All I saw was happiness and kindness and love in all its forms. It was an amazing day, aided by the perfect weather.

“You know,” Kaye said, once the parade had passed, “the day isn’t really over. If you want to capture the whole event,” she nodded towards my camera, “then you need to come to the park with us.” I didn’t object and she led me off along the street.

We met up with her friends, who had ditched their instruments and found some feather boas to accessorise their uniforms. Together, we made our way over to where a few bands that I hadn’t heard since the 90s were playing on a large stage in one corner of the park. Several rounds of drinks were bought and I was really starting to enjoy myself. I even danced with some of her friends, but Kaye stuck pretty close to me the whole time.

After a while, Kaye and I left the group, grabbed some snacks from the street food stands and made our way out beyond the crowd. We found a spot under a tree on the edge of the park and sat in the pleasantly cool shade. We talked for hours. I can be a bit awkward, especially around new people, but there was something about her. I don’t think I had ever met anyone - from anywhere on the gender spectrum - who was so easy to talk to. It turned out that we had a lot in common. She was doing a different degree, but she had some of the same modules with the same lecturers who had taught me. We also had similar taste in music, video games and movies.

I was curious about her transition but was hesitant to ask. However, she seemed quite happy to talk about some of it. She told me that she had been Kaitlyn ever since she had arrived at University. She had wanted to start a new life in a new city and hinted at a difficult and confusing adolescence, but I was pleasantly surprised to hear that her parents and her best friends had been very understanding and supportive.

“Sorry, you’re probably sick of answering dumb questions about all this,” I said after we had finished a discussion about pronouns.

“Meh, it’s fine,” Kaye said. “To be honest, I don’t really talk about it most of the time. I was introduced to most people here as a woman so, as far as they’re concerned, I am one. Which is exactly what I wanted.” She went on to explain how she had been on hormones for a couple of years before she moved away.

“So, what does that actually mean?” I asked.

“It causes a few changes, but... well, most importantly,” she said, smiling, “it means that these are real.” She grabbed her breasts and squeezed them. The neckline of her top was pretty low and this wasn’t the first time that day that my eyes had been drawn towards her cleavage. Her breasts were probably a b-cup and they certainly looked real enough.

We sat under the tree for a while, chatting and watching the world go by. There were all kinds of couples wandering around, holding hands or sitting with their arms around each other. The atmosphere was incredible.

“So why did you come to Pride then?” Kaye asked, eventually.

“Well,” I said, “it’s something I’ve never done before and I was… curious.”

“Now, when you say ‘curious’...?” she said, with a certain amount of anticipation in her voice.

“Funny you should say that,” I replied. I explained about how my sexuality had seemed more fluid recently. I’m not sure why I told her, I’m not sure if I could have told any of this to any of my other friends. I just felt really comfortable around her and it was great to finally say some of it out loud. “Not that I had any ulterior motive for coming here today or anything,” I babbled. “Other than getting loads of likes on Instagram, I mean.” There was that adorable smile again.

Sometime later, we headed back to the food vans and returned with two enormous burgers. After eating far too much, we lay on the grass next to each other, groaning theatrically for a while, before continuing to talk about life, the universe and everything.

At one point, she shifted position, moving closer to me, and her finger brushed the back of my hand. I wasn’t sure if it had been accidental, so I cautiously turned my hand over and slid it towards hers. She placed her hand in mine and felt a tingle of excitement as our fingers intertwined. In the background, a local guy with a guitar was on stage doing an acoustic set. Soothing music drifted across the park, adding to the romantic atmosphere. Kaye turned onto her side, her head resting on her hand, and I turned my head to face her. She had taken off her sunglasses, so I was finally able to take in the details of her appearance. She really was very beautiful. She had a cute, round face and whenever she smiled her cheeks dimpled and her large, green eyes sparkled. If I thought about it, I could kind of picture what she might look like as a guy, but I’ve subsequently discovered that you can do that with a lot of people. Her hair was sandy blonde with what looked like natural highlights and she had one errant strand that she had to keep tucking behind her ear, which I found adorable. Her skin was pale and she had freckles across her cheeks and nose. She wore a minimal amount of makeup around her eyes and lipstick in a subtle, reddish shade.

I could feel the excitement; the tension in the air. I subconsciously licked my lips and a few moments later hers were pressed against mine. I had expected it to feel somehow different or unusual, but all I felt was the same rush that I had felt during half-a-dozen first kisses before.

We made out for a while, then broke apart and she cuddled into me, putting one leg over me, possessively. It may have been my imagination, but I thought I could feel the unfamiliar, but not unpleasant, sensation of her erection pressing against my thigh. I was pleasantly surprised at how arousing it was, being able to feel that she was turned on and knowing that it was because of me. With the way her thigh was placed, I’m sure she could feel how aroused I was too.

After a short, slightly awkward silence, the conversation continued for some time as the sun went down, interrupted by the occasional kissing session, until Kaye sat up and wrapped her arms around herself. Her exposed skin was covered in goose pimples. The sun had pretty much set, but it didn’t feel that cold to me.

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“You’ve really got the hang of this whole woman thing, haven’t you,” I said, without thinking, then panicked that I’d said something inappropriate. Fortunately, Kaye just laughed.

“Yeah, I suppose I have,” she said.

“Here,” I said, rummaging in my bag.

“Thanks,” she said, wrapping my hoody around herself.

The acoustic guy had finished and a DJ had taken over, increasing the volume and rhythm of the music. There was some activity behind him as the organisers got the stage ready for the evening’s entertainment.

“I might head home,” Kaye said, probably dropping a heavy hint that went straight over my head.

“Oh, uh, okay,” I said. “Where is home anyway?”

“I’ve got a flat on Park View,” she said.

“Ah, cool,” I said. “That’s on my way home. I could walk you back. If you like?”

“OK,” she said, smiling.

We gathered up our things and headed away from the park. The conversation continued, perhaps a little more awkwardly, as we made our way through the city centre. After a while, I reached out my hand and she slid her fingers between mine again. I was surprised to find that I was a little nervous. I found myself looking around anxiously. There may have been some funny looks from passers-by, but that might have been my paranoid imagination. We still had our Pride scarves on, but there wasn’t any way for anybody to tell that we were anything other than a ‘normal’, heterosexual couple. I can only imagine what it must be like for gay couples; did they feel this anxious and exposed all the time?

Eventually, we stopped outside a row of houses.

“Well, this is me,” she said.

“Ah, OK,” I said. There was a long pause.

“Thanks for today,” she said, “it’s been really nice to hang out with you.”

“Yeah,” I said, awkwardly. “Thanks for being by Pride Guide.”

We hugged and she held on to me for quite some time. When the hug broke, she stared up into my eyes.

“Do you want to... you know... maybe hang out again sometime?” I said, stupidly, to break the silence.

“Well, we could hang out some more right now?” she said, her eyes twinkling.

“Urm, OK,” I said. She kissed me, harder this time, then took my hand and led me inside.

My eyes were drawn to her curvy ass in those tight denim shorts as I followed her up the stairs. She stopped on the first landing and turned, wrapping her arms around me and kissed me, passionately. I pushed her back, pinning her against the wall with my hands at her waist and kissed her even harder. I felt light-headed, probably because most of my blood was nowhere near my brain; all I knew was that I wanted her. She reached down and grabbed the bulge in my shorts, causing me to moan. My hand made its way instinctively up towards her chest. Her breast certainly felt real enough!

We were shaken from our reverie by the sound of a door closing and managed to disentangle ourselves just as a young woman descended the stairs from the floor above. Kaye had gone bright red. She fumbled for her keys, said an awkward ‘hello’ to her neighbour and clumsily fiddled with the lock. I followed her inside and she closed the door, leaning back against it as we both started laughing.

We kicked off our shoes and I followed her into the living area, which was a small space dominated by a couch and a large TV. She dropped her phone on the coffee table, where a game controller and a couple of empty bottles had been abandoned.

“Sorry about the mess,” she said, moving to pick up a blanket from the sofa.

“Don’t worry about it,” I said, wrapping my arm around her and pulling her back into a kiss. The blanket fell forgotten from her hand. My t-shirt and the hoody were quickly discarded.

We collapsed onto the couch and it wasn’t long before she had loosened my shorts and her hand had slipped inside my boxers. Her shorts were too tight to get my hand into, so I unzipped them and pulled them down, causing her cock to spring free. It felt slightly strange to wrap my fingers around someone else’s erection for the first time, but I was loving it. I could feel the warmth of her between my fingers; feel her throbbing and straining to my touch. It was so incredibly exciting to know that I was the reason she was so hard.

We were both so horny but neither of us wanted to break apart from the kiss. We continued more and more passionately, each rubbing the other’s cock faster and faster.

She came first. The sound of her gasping and moaning as the orgasm built up was so incredibly sexy. I felt her body trembling, felt her cock throbbing between my fingers and a small amount of cum - a side effect of the hormones, I learned later - seeped onto her belly. Making her cum turned me on so much; I probably would have cum immediately if her pace hadn’t slowed during her orgasm. Once she had calmed down, she pulled my cock out and my hand moved up, lifting her top and exposing her breasts. I caressed her through her bra as we continued to make out and it wasn’t long before I came too, firing spurt after spurt of cum across my chest. We slumped sideways and nestled up together on the sofa.

Eventually, Kaye got up, slid out of her loosened clothes, and walked away in just her bra and panties, which were a matching set; red, lacy and partly see-through. She definitely seemed to have curves in all the right places and her underwear hugged those curves perfectly. She returned with some tissue and we cleaned ourselves up, but not until she had licked some of my cum from her fingers seductively.

She returned again with some drinks, and then we slumped back against the cushions, both mostly naked. I offered to retrieve the blanket for her, but she told me to just put my arms around her instead. We didn’t even turn the TV on or anything, we just lay there, fingertips occasionally circling on each other's exposed skin, and talked for hours and hours. Kaye’s phone buzzed at one point and when she picked it up to check it, I noticed the time; 2 am.

“Bloody hell, is that the time?” I said.

“Woah, yeah,” she said.

“I can head off if you want,” I said. I didn’t want to leave, but I didn’t want to seem presumptuous.

“Stay,” she said, simply.

A little while later, we made our way into the bedroom. Instead of turning on the main light, Kaye went over to the bed and switched on a string of fairy lights that were wrapped around the headboard. The room was small; containing just a queen-sized bed, two bedside drawers and wardrobes along one wall. It was a fairly standard student room, decorated with posters and photos of Kaye with her family and friends, but it looked homely and almost magical in the light of a hundred tiny LEDs. We lay down on top the duvet, staring up at the patterns on the ceiling, which changed as the lights twinkled, and chatted for a while before things started to heat up again.

This time, we took our time. We made out for several minutes before our hands began to explore each other’s bodies. I unhooked her bra to reveal her small but perky breasts. She slipped her panties off and slid them down her long, smooth legs. I slid my shorts and boxers down and scooped off my socks. Finally, we were naked together. I took a moment to admire her figure. Her body was so incredibly sexy and seemed totally feminine, apart from the obvious exception. Her eyes sparkled as they scanned my body in return. I’m no gym freak, but I eat fairly healthily, keep my hair trimmed and generally try to look after myself, so I’m quite comfortable in my own skin.

This time, it was her turn to lick her lips and my turn to lean in. My hand started to slide down towards her cock as we kissed, but before I could reach it, she shifted position and climbed on top of me, straddling me. She started grinding back and forth so that our cocks rubbed against each other as she kissed me. Then, she sat up and took both cocks in her hand, stroking them in unison. I watched in fascination as they slid together between her fingers. Hers was smaller and thinner than mine, but not by much. It was so exhilarating to feel the pressure and the heat of someone else’s hard cock rubbing against my own.

She seemed to know instinctively how to tease me, taking me to the edge of orgasm and back several times and making me even hornier, which I wouldn’t have thought possible. After the third edge, I couldn’t take it anymore. I grabbed her around the waist and gently-but-firmly pushed her off me. I climbed on top of her, kneeling between her legs, and began to kiss my way down her body, osculating across her breasts before taking each nipple into my mouth, and then continuing down across her abdomen. Her groans and whimpers drove me wild. I already had her cock in my hand and was stroking it before my lips finally made contact.

“I’ve never done this before,” I said, kissing my way across her skin from her balls up along her shaft.

“Don’t worry, I’m sure you’ll- Oh!” she moaned as I wrapped my lips around her head. I tried to think about all the blowjobs I’d had before and what I really liked. I teased her balls with my fingers as I focussed on sucking the first few inches and licking the tip. Her flesh felt warm between my lips and she tasted surprisingly pleasant; the flavour of skin with just a hint of sweat and cum, but not in a bad way. Definitely not in a bad way!

I got revenge by taking her to the edge, then backing off as she became more vocal and her cock started to throb more and more. I repeated this several times until, finally, I relented and she came in my mouth. I felt her cock pulsing between my lips. Again, there was only a small amount of cum. It’s often described as sweet, but that’s not the word I would choose. It wasn’t unpleasant though, kind of like hot, salty gravy. I swallowed it and kept kissing her as she began to soften, until she became too sensitive to take any more.

We rolled over and she took up a new position, lying on her belly between my legs with her bare feet in the air. I watched as she expertly worked my cock with her hands and mouth. Once again, she brought me to the edge of orgasm several times. It was incredible and I still remember it as one of the best blowjobs of my life. I felt the pressure building again and this time, as she maintained eye contact and moaned encouragingly, I came in her mouth and she swallowed it all. The orgasm was incredible and it took me some time to recover.

When my orgasm had finally subsided, she moved up to kiss me. Then, with barely another word, she turned out the lights, we manoeuvred ourselves under the duvet and she cuddled into me with her head on my chest.

“Wow,” was all I could say.

“Yeah,” she said, happily. We chatted lazily for a little while, but we were both in a state of post-orgasmic bliss and it wasn’t long before we both fell asleep, naked in each other’s arms.

-----

So, that was my first experience of Pride. It was the start of a beautiful friends-with-benefits-ship.

Now I come to think about it, I don’t think I ever did get that hoody back!

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Written by SamHarper
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