I hadn't been around horses growing up. It wasn't until I turned 24 that I tried my first riding excursion. I fell in love with it immediately. I loved the outdoors and the company of such gentle majestic creatures. I became very good very quickly and due to my small stature, a friend hooked me up to try out being a jockey. I loved it and found myself spending quite a bit of time at the track. In just 10 years I had become a professional jockey!
I was mostly a loner at the track and didn't spend much time with the other jockeys. I tended to favour solitude due or the company of close friends due to other developments. Most of my personal time was now spent as a woman.
I had started an ongoing relationship with a man I met on the internet. We had an intense sexual relationship full of experimentation and lust. Together, we had travelled, had threesomes with other T-girls and other Daddy studs, and role played any scenario we could imagine. Still our relationship remained casual and based mostly on our complimentary desires rather than cupid's arrow.
It was at the track that cupid's arrow struck in the form of a big cowboy type worker named Ray. Ray was 55, about 5'11 with dirty blond hair and a bushy moustache all with a peppering of grey. A thick bush of chest hair parted his shirt which clung to his well worked pecs. He had a thick, toned body and his blue work pants hugged his muscled ass. I also caught a glimpse of a large bulge that worked it's way down his pant-leg. The sight of Ray had left me breathless! I think I must have blushed whenever he said hi because in his presence I felt like a little school girl getting attention from the high school football hero. Soon I was turning down dates with online friends and spending nights alone fantasizing about Ray. I realized had a big crush on this guy!
Opportunities to get to know Ray were not plentiful. He worked behind the scenes doing the really backbreaking work caring for the track and the animals. I didn't have the guts to approach him and didn't even know if he was gay. I did know that he didn't have a wife or girlfriend but he worked such long hours that it wasn't surprising. I had never been presented with the challenge of trying to seduce a man and I didn't know where to begin. Fate as it turned out was going to guide me and give me every opportunity I needed, ready or not.
I had decided to start doing my workout at the jockey's gym in the evening because it was almost always empty. I don't mind dressing a little flashy in the gym because the few people there pay no attention. My gym outfits always are butt hugging Lycra numbers that compliment my firm body. My workout is largely cardio except I weight train my glutes to help keep my cheeks big and round. I wasn't conscious of being watched but as I knelt on all fours doing mule kicks, a pair of sexy blue eyes were admiring my butt and liking what they saw. I didn't have a clue that Ray was behind me working out on the bench press until all 3 gruelling sets were completed. I was shocked when I turned around and saw him there. I could of swore that he had only started doing presses when I turned around but he was red. I realized he was uncomfortable so I gave him a wide genuine smile and greeted him "Hi Ray". I turned red and felt like I'd laid it on too thick. "Hi, uh Kori right?" "Yes that's right" I smiled and laughed a little uncomfortably "I've never seen you work out here before" "This is the first time. It's really great though because there's hardly anyone here and the facilities are great!" "Most jockeys are so concerned about weight that they only do crazy diets and cardio. All of these weight machines go to waste" "Well I like to keep a fit body. I don't do the crazy jockey diet stuff. I do like to keep a good cushion for the saddle though" I chuckled as a pat my ass "It sure has paid off he chuckled"
"Thanks!" I giggled
I did the rest of my workout with renewed vigour. I lost track of Ray but knew I'd be hitting this gym every night from now on. I did my stretches and decided to hit the shower. When I got there, Ray was showering and didn't see me come in.
My body is hairless and my little mound of pubic hair sculpted. There is no mistaking that it is intentional and bod I resisted the urge to watch Ray shower and went about washing my long hair. I hoped while I twirled around pretending to have soap in my eyes he'd take the opportunity to take in my toned, tanned smooth body. When I opened my eyes like I guessed I had caught him watching. He moved quickly to act like he had turned to wash out his pits and be turned away from me. His cock, half rigid and easily 9 inches trailed behind long enough for a glance. I hoped he wasn't embarrassed. I decided to exit first so he wouldn't feel like I was going to see his semi-hard-on. I did have one little treat I wanted to leave him with though. When he did come out I was standing with my back to him drying my hair. I wanted him to have another chance to look at my bod but I wanted to send a little message too. That's why I wore my red satin thong. When I saw his shadow approaching I made sure I was leaning over combing out my long hair where I couldn't see him in the mirror. I'm pretty sure he'd taken a good look and when I turned around I acted startled and said, " Oh Ray, sorry I didn't know you were there." "Oh it's ok sorry I snuck up on you I guess" "Any big plans for the weekend?" "No we're prepping the track for Sunday" "Oh that's no fair" I kind of pouted and he gave me a big smile I gave him a big smile back "great talking Kori have a great weekend!" "You too Ray, It's really nice to meet you" I gave him a smile with just a hint of bedroom eyes and turned around to continue preening my hair. I wished I would have had the guts to ask him out but things were promising. I vowed that if he gives me just one clear message I will take the plunge and try to get with that stud.
The next week when I went to the gym Ray was there and we continued subtly flirting. I knew he was liking me and probably wanted to take me right there. What I didn't know was how comfortable he was with his feelings and whether he would act on them given a chance. We grew more comfortable each night and showering became a trade of each showing and admiring the other's body. Still it was a game with neither of us having the guts to come right out and ask the other out. I kept hoping for the day when in his way he gave me the sign I needed. He had began using the locker next to mine so we could chat as our conversations had become deeper and more interesting. I had grown to love Ray's company as a friend and he mine. I had also began playing a little game of show and tell to try and encourage a sexual relationship. I think when he saw my lacy red garter-belt in my open gym-bag on Wednesday he got his idea. Thursday I came to the gym and Ray was already there working out. In the change room he had left his bag open by my locker. A magazine was poking out and as he guessed my curiousity about all things Ray led me to look. My mouth dropped open to see a porno mag of older men with little twink bottoms dressed in lingerie. The featured pictorial was a "girl" with features much like mine getting thoroughly drilled by a big hunky man. It was all I could do during our workout and shower not to make my move. I had it for Ray so bad and I wanted to close the deal in a special way. The plan I had formulated was not discreet but for the last couple evenings we'd had the whole track let alone the gym to ourselves.
On Friday I was in the shower when Ray showed up. He looked disappointed that I wouldn't be joining him for the workout. I explained that I had an errand to run before 7 but I wondered if he'd like me to meet him after his workout and we could hang out this evening. His disappointment quickly changed to an excited grin. "I'd love to Kori!" He looked distressed that he'd answered so enthusiastically "Great Ray, I'll be back at seven-thirty!" I sounded almost girlish and rubbed his elbow while I spoke. I don't think he felt self-conscious now, he had a huge tent in his shorts! I realized my little cock was at attention too and buck naked in the shower! We smiled at each other and almost kissed. We broke it off thinking better of being this public now. Neither of us wanted it a subject of the track gossip line. I reached up and rubbed his shoulders and he patted my bare bum. Then he went to the gym to work out and I went to get ready for our first date!
I love the feeling of anticipation when you know you are going to get intimate with someone for the first time. I don't think you can ever completely guess by a person's public personality what their sexual personality will be. The unveiling of that mystery can be either magnificent beyond your dreams or a complete let down. I felt strongly that Ray was going to be magnificent, but I was biased because I had such a crush. I showed up back at the gym having checked around to see who was still at the track. I hoped no one was there because anyone who saw me would have learned allot about my private life in one glance. I had planned to ride with Ray up to a secluded lookout point to have a bottle of wine and watch the sunset. I had a nice thick blanket that we could sit on and a couple of pillows. I had prepared one of the big trail riding horses and loaded up his saddlebags before I changed. My outfit was sure to cause a reaction of some kind. I felt confident he'd love it. I wore a strippers tear off black g-string with a pink bow at the top of my ass crack. I love the statement this makes to men who top me. The bow seems to say "I'm giving myself to you and you own my body for your pleasure". Over that I wore a black lacy garter
belt just like the red one he already knew I owned. Thigh high lace top stockings completed the set. I don't bother with a bra because I haven't augmented my breasts and don't plan to. I had completely made up my face and curled my hair into big sexy locks which were bundled up into a ponytail with little ringlets framing my face. I wore a very formal Victorian riding jacket with tails and riding boots,cap and gloves. I had the traditional turtleneck riding shirt under the jacket. I left the pants at home!
He was dressing when I walked into the change room. The look on his face was priceless! I smiled and looked into his eyes giving him the sexiest bedroom eyes I could make. "Ray I was wondering if you might like to accompany me up to the ridge for a romantic sunset" I purred. His arms were already around my gently stroking my buttocks under the tails of my jacket. My arms were draped around his neck and we gently kissed. "I'd be honoured miss Kori" He purred into my ear in a deep manly voice. "I'd watch a million sunsets with you! " We kissed again and he leaned back taking in my appearance. Shaking his head he said, "I hope you'll consider joining me for sunrise too" I leaned in and gave him another kiss and smiled "Our horse awaits sir!" He nuzzled into my neck and kissed my cheek the whole ride to the top of the ridge. He tied the horse and gave it water while I spread the blanket and poured some wine. I had a flashlight on hand in case we were low on moonlight returning. He held up a glass and toasted me "To new love" he said I blushed and repeated "To new love" Then I was in his arms lost in a kiss while his hands firmly caressed and explored my body. We were both breathing so heavy and intense. I noticed I was whimpering and sighing unconsciously. He had kneeled and leaned back with me straddling his lap. I was off balance and being supported by his hands holding my butt. I trusted him to hold me while I undid his shirt and ran my fingers through his hair and his sexy chest. Never had I felt such overwhelming lust with anyone as I felt with Ray. He fell back and I fell forward on top of him. We both giggled and I leaned my forehead gently to his. We kissed passionately him fondling my butt and rubbing my legs while I continued to rub his chest. His fingers had worked there way to my asshole and he was massaging it gently with two fingers. He had worked his way there so subtly and naturally that I was already in the full throes of delight when I realized what he was doing. "oh Ray this is a dream come true!" I could hardly get the breath to make a noise between whimpering and moaning. " I wish I could dream such a beautiful dream as this Kori" He moaned back in a deep voice. I moved off and kneeled beside him in such a way that he could keep playing with it. Then I undid his belt and took out his enormous cock. It was even bigger than my first lover's cock and he had a giant! Luckily I've worked out some moves for pleasuring such a big dick and went to work licking up the shaft. I made a big schlopp noise as I sucked hard on the head and let it pop out of my mouth. Then I let some spit run down it so I could jerk him off while I looked him in the eye, "God baby, your cock is so gorgeous" I whimpered to him "Oh Kori, you're sexy little thing. God you make me feel like a king!" "Ray you are my king, from now on baby if you'll have me" It is easy to give a great blow job when you have fallen in love with the man you're blowing. There was no pleasure I would deny Ray. If he told me to do something I would do it without question. The days where Ray had to ask were over. I gave my all to him and I knew my reward was going to shoot down my throat soon. While I cradled his balls and deep-throated him sucking as hard as I could as my lips slid back and forth on his cock, he as found a spot just above my asshole that was driving me insane! I don't know if that is some part of the prostate or what but in a little spot just above my asshole Ray found a G-spot. Just as a big shot of cum was filling my mouth from my gorgeous new Daddy's cock his massage gave me the wildest orgasm of my life! I was still trying to drink down his cum but had to let the last few jets coat my face while my legs shivered and I shot out jizz of my own. He caught it in his hand and brought it to my mouth letting me lick it off his fingers and rubbing the mixture of our cum into my glossy lips. I collapsed onto him with my head down by his cock and him gently rubbing my but t and we lay that way to watch the last glimpse of sun give way to a massive starry sky. After a while, we decided to head back, pick up some of his things and go to my house where he would be my guest for the weekend. I felt no self consciousness at having been a total slut for Ray. I just wanted to give him more and more. I desired him like I've never desired anyone. I realized for the first time in my life I was in love and with the way Ray gently kissed me as we got ready to drive to my house and into our relationship, I knew I'd found a man who loved me too!