Warning this story contains graphic descriptions of sex between gay men.
I first started crossdressing at age 10. I can remember loving the way it made me feel but not knowing what it meant. I somehow knew it was something I better keep private. I hadn't yet really developed an interest in girls or men, I just got very excited in sexy clothes.
I had my first dream about a man when I was 14. In my dream I was in a cozy,rustic room dancing around in front of a very distinguished looking older man who sat gazing appreciatively from a comfy armchair. A fireplace crackled gently beside us and provided the soft light which reflected off my tanned, smooth skin. I wore only a black garterbelt,stockings and high heels. My long brown hair was done in big luxurios curls and big gold hooped earings hung from my ears. I even remember the rich eyemakeup,blush and lipstick which complemented my big brown eyes,blushing cheeks and pouting lips. What I remember most is a feeling that ultimately guided me to the story I'm about to tell.
I have always been a small man, I stand only 5'6 135 lbs as an adult, as a teenage boy I was less than 5'. The man in my dream was tall-6'4 220lbs and powerful looking, yet it felt as though little me in my heels and stockings, had this sexy stud totally in my power. It wasn't until my 30's that I realized that this was the very type of scenario I needed to complete me sexually and find hapiness.
My first time with a man was in my early thirties. I met him on the internet and found it very easy to communicate my desires and fantasies to him. I couldn't believe how well our fantasies meshed as though we had been pre-destined as partners. He was tall,fit and nearing 50 and liked to wear leather. After me chickening out several times we finally got together and I had my first gay sex. It all went by like a dream,but I found myself hung up with doubts and unable to completely let go. Luckily my lover was very skilled (and well hung I might add) and he was able to make up for my passive behaviour. He gently and effortlessly placed me in different positions and guided me through a wonderful first time. I came several times yet left convincing myself (lying to myself) that although I had enjoyed it, it was just experimenting and I wouldn't pursue it further.
My second time was with the same man but we only got to forplay before I chickened out. That time I felt guilt and shame because I had been cultivating a heterosexual relationship and felt like I was cheating. We parted as friends but I had convinced myself that I should stick to girls and keep men in my most private fantasies only. The problem of course was that I could never give all of my sexual identity to a hetero relationship either. Keeping that big a piece of your sexual identity secret makes you a cold unsharing lover. One by one relationships with women started off good and would fizzel out when my feminine side would drag me into a depression. So many times I didn't want to be touched by anyone but my secret gay lover. In my mid thirties after a painful, emotional breakup I decided not to date for 1 year and sort my head out. It was in this year that I struck it rich. I won't bore you with the details but my whole life changed. I had enough that I would never need to work another day in my life and I could have anything I want. But there was only one thing I found myself thinking about, and I set out to create the conditions I needed to give myself to my desires. I also re-established communication with the man who had taken my virginity. Over the next months I made strong commitments to my feminine side. I took up yoga and got a personal trainer. I had my body hair removed professionally and started tanning sessions. I grew my hair long and lush with the help of a stylist. Best of all I bought absolute privacy in a secluded cabin up north. The two story cabin was on a lake. On the top was the open kitchen, living room and master bedroom both with a fireplace. The bottom floor was a recroom with bar,fireplace and glass opening on to the patio. There was also a guest bedroom on the bottom floor. Our relationship continued to build on the internet. I knew he would want to get together soon, he didn't yet know about my cabin and how much I had already prepared for our third meeting. I had aquired a dream wardrobe of lingerie, sexy dresses and jewellry and I had even had chaps, a leather vest and biker hat made specially for him. I was ready.I propositioned him to come to my cabin for a week. He immediately accepted and it was underway. The day he was to arrive came quickly. That morning I did yoga and cleaned the cabin. I then started preparing dinner so I could throw it in the oven later. I layed out my evening wear. For lingerie I had chosen a black garterbelt,stockings,4" stillettos,a black satin thong with side tear offs, a red sheer halter top, and a tight short black mini-skirt. I poured a bath and relaxed in bath oil. It was 4:00 he would be here in 4 hours. After my bath I did my hair and makeup, dressed in my lingerie and admired my look in the mirror. I had truly accomplished the look I wanted, a very classy slut. I finished dressing and checked myself again. "Look out fella I'm going to rock your world" I said aloud and went out and put the food in the oven. It was 6:30. He showed up a little ahead of schedual. I was ready and didn't mind as I was so horny I could have jumped him then and there. He stopped and gave me a wolfish grin when he saw me. "You look delicious!" he said in a sultry tone. I thanked him and we kissed lightly. I gave him a brief tour of our love nest and then served dinner. After dinner I asked him to wait for me in the rec room and pour us some drinks. I grabbed a big satin pillow, the suprise gift I had for him,and a bottle of cherry cheesecake flavoured lubricant and went down to join him. I set the pillow down beside the armchair which sat next to the fireplace. I stashed the lube nearby and met him by the bar. He grabbed my ass, guided me up to him and we began necking. I took the drink he had mixed me and we toasted, "here's to life affirming sex" I said and we drank. I then took him by the hand and guided him over to the armchair. I sat him in front of the fire and went over to put on some music and dim the lights. The sexy r&b started and I went to him. I shimmied out of my dress and halter top and began to sway and spin right in front of him like a lap dancer. He looked me up and down with lust and began to pinch, spank and caress my smooth body as it swayed in front of him. I felt so sexy and powerful as well as very turned on. I also felt as though we were the only poeple in the world at that moment, cacooned in our rustic lovenest and isolated by miles of snowy forest. I undid my thong, let it drop and went about stripping him. As I took off his clothes I licked and gently carressed his muscular body. He was loving every minute of it and cooing words of appreciation in return. When I had him stipped naked, he grabbed me and pulled me on his knee. He began fondelling and caressing my legs and ass. I decided it was time to show him I could be aggressive too. I grabbed his hard thick 8"cock and started sliding it up and down in the crack of my ass. I clenched my buttcheeks and started jerking him. Soon I was sliding up and down on his lap jerking his big cock off with my ass. He was going wild, but not as wild as me. I had to stop before I came. I had plans for this man. "Honey for the rest of this week I want you to feel free to take charge and enjoy my body as you wish." I said in a breathy voice," but for now I want you to sit in that chair, do nothing and let me take control." He smiled and lounged back in the armchair. I took the satin pillow and plopped it in front of him so I could kneel comfortably. I then licked and kissed my way from his toes to his mouth, neck and back to his toes again. After gently sucking his toes I began to go to work on that 8" by 5" cock of his. I smiled naughtily at my stud and fliped my long brown curls over my left shoulder I grabbed his cock at the base and began swirling my tongue up it like it was melting ice cream. He moaned and cooed as I stared in his eyes, licked up his shaft and swirled around his head. I went down and sucked, licked and kissed his balls. I stuck my tongue in his ass and pulled back when I noticed he was about to cum. I started sucking hard on his head and popping his big cock in and out of my mouth. He was lost in pleasure and was talking dirty to me. "Oh yeah Kori suck daddies big cock oh you look so sexy my little boytoy!" I grabbed the lubricant, dumped a bunch in my hand and started jerking him off." My god my hand doesn't even get around it!" I remember marvelling. I set out to lick and suck off every tasty drop of lube off his glistening dick. The lubricant made it easier to deepthroat and I started bobbing, sucking my mouth down his shaft and pulling my head up while I kept sucking. I'd wet his cock with a big load of spit and suck it off the end like it was a big wad of cum. Then I gently blew a stream of air up and down his big shaft. He seemed to love my sense of drama. I rubbed him around my lips a flicked my tonge on his big head. When I'd feel his balls tighten up, I'd back off a bit and resume when he started to relax. I kept him on the edge of cumming for an hour this way. I had never been so wildly turned on. My inhibitions had all gone and I was stripped down to my desire. Every breath was like a hot wind and I was ready to cum. I smiled sexy for him, looked him in the eye and jerked him off into my mouth, sucking and licking as I did so. Soon he was spraying big jets of hot cum in my mouth and on my face. I squeeled with pleasure as I spilled my own cum all over the satin pillow. "Thanks stud I needed that" I said still breathless from my orgasm "My god Kori, that was the best blowjob I've ever had thank you!" "I have one more present for you" I cooed and handed him the leather gear " I think you should go slip into this and take charge of this situation stud." I winked and kissed his cock. He went to change and I refreshed our drinks.
He came back looking big and butch with his cock standing at attention again. He took the drinks out of my hand and set them aside. He held be close and stroked and needed my ass, kissing and licking my neck, rubbing my back. Then he picked me up, and placed me on all fours on the eairmchair, my head facing the backrest. He stuck his tongue up my ass and I went wild. I squeeled and after only minutes I was cumming again, my legs quivering. He picked me up and lay me on the satin sheets of my big bed. He put on a condom and lubed his cock. Next thing I knew my legs were in the air and his head was pushing at my pussy. I relaxed my muscles and he popped in. My eyes must have rolled in my head as a sharp pain consumed me. I managed to relax again as pain was replaced by a gentle but persistent pressure building in my ass. He was slowly working his big cock in. It began to feel good and I wimpered. Soon my legs were hooked around his waist and he was gently sawing in and out. The pressure of that big cock in my ass never let up and I felt so in his control. My lust was reaching a boiling point and I began talking dirty. "Oh yes leatherdaddy! fuck me good make me your little whore!" He responded by moving me over on my side, lifting my leg and entering from behind. I rubbed his balls gently and cooed while he kissed my neck and ran his hand all over my body. It felt like hours past in this position before he sat up on the edge of the bed, made me straddle his lap with my back to him, and began bouncing me up and down on his cock like I was getting a ponyride! I was squeeling incoherently and it wasn't long before I came again! He layed back on the bed and had me straddle his waist facing him. I was so much smaller than him he could just pick me up and set me where he wanted. I loved this feeling of being under his control. He had me jerk off his cock in my asscrack. As I rubbed my asshole up and down his shaft I played with his nipples. Soon his cock was up my ass again and I was riding on top. He picked me up, set me on all fours, grabbed a handful of hair and started driving me home. "Oh my god yes! fuck me hard stud Fuck Me!" I was lost in paradise. I could here the bed squeeking with our intense fucking. At one point I fell forward off the bed doing a handstand while he grabbed my hips and pulled me back on his cock and back on the bed. I looked back at him with lusty eyes and stroked his balls. His fucking got even more intense. "Oh cum for me stud! show me I make you feel good! cum in my ass! please daddy!" He let out a primal moan and pulled me down balls deep on his cock. I could feel it spasm against my prostate and a deep intense orgasm began to build. I came so hard I cried for a while afterward. But they were tears of satisfied joy. Afterward we hopped in the bath together with a couple of drinks and froliked like newlyweds. I slipped into my baby doll and we went back to the bedroom. Needless to say it was a sleepless night full of sexual adventure. In the next week we bonded like the rogers and astaire of the bedroom. It was a week full of things to write about and I look forward to telling more. Thank you stud for your patience and the beautiful nights we've shared. Love Kori :)