God I was glad to be home, a two-hour train nightmare. Every stop from Liverpool Street on the 6pm slow train to the dreary little Essex village that was the only place I could afford to rent a studio flat. My only consolation was the bag of goodies I brought in my lunchtime and the anticipation that tomorrow was Friday and my big night in with my mysterious blind date. I had been living in my little studio flat for about a year and I have to admit, after a string of disastrous relationships co-habiting only to get chucked out when it went wrong as they found out I was a transvestite, was fantastic to have my own space especially as I loved to feel feminine and dressed as a woman every opportunity. That day, during my lunch break I had treated myself to a lovely pair of black strappy stilettos with diamante on the toe strap and some very sheer black hold ups. I have thirty pairs of high heels and many pairs of stockings but its that thrill of buying them and getting home and slipping them on to freshly shaved smooth legs and furiously masturbating to a glorious orgasm, that’s what I love and my idea of heaven. I always knew I was gay really, I guess the fact that every time I made love to a woman I had to fantasise about dressing up and having sex with men to cum gave the game away but the first encounters with men weren’t as satisfying as I thought they would be but the men I went with were not very attractive so I guess it’s the same as sleeping with an ugly woman. What I really longed for was a handsome hunk who made my heart race and I would be a total slut for and he would fulfil all my womanly desires but would the dream man ever be real?
I am very lucky really, I am five foot six, 10 stone and a size ten with a small round face and when I have been to way out club or transmission I have got lots of attention from men and positive comments from other girls. I love taking very slutty pictures of myself nearly naked in stockings and heels; this was my inspiration for placing an advert in the county newspaper. It read like so ‘Male 35,TV, Very Slim, Smooth, Feminine, very sexy and attractive seeks photographer for glamour photo session’
I thought that I might just get a few old men who want to wank on me but at least I would get some nice photos of me as I was fed up with trying to take my own photos all the time and them coming out rubbish, but I was amazed to get about ten or so responses and after I had chatted with them on the phone I had set up dates, three of them were going to come round, starting this Friday with a policeman called Simon to photograph me on Friday at eight. They were all under thirty, liked to go to the gym or played sports, had good jobs and were single or so they said but that didn’t bother me. I was a bit over whelmed really. Was I about to fulfil my dream of very exciting gay sex with a handsome man?
Friday dragged on for what seemed like an eternity, got soaked going to the train station, no seat on the train and a full in-tray on my desk and I guess watching the clock, constantly staring at the second hand going round was not helping the day pass. Eventually the day was over and I made my way home, managed to get the 5.00 fast train and a seat all the way home, even the warm setting evening sun on my face as I walked home from the station was giving me a good feeling about that night. I briefly stopped of in the off license to get a bottle of wine and some cigarettes but I was soon home and started running a hot bath and opened the bottle of wine, within five minutes of being inside. Once in the bath I gave myself a long soak whilst sipping a glass of wine and thinking of all the naughty things I would like to do with a handsome muscular man. I was almost in a trance thinking of sucking on stiff prick oozing pre-come until it shot hot spurts of salty cum into the back of my mouth. After a soak I shaved my legs, arms, genitals, bum and face, only took a few minutes as I shave my body every morning but worth it as I want to be as smooth and sexy for my man. I love having smooth skin, its such a turn on and feels so feminine. Once out of the bath and dried myself of, I painted my finger and toenails in the brightest red glossy nail varnish I could find. Next it was foundation and eye make up, blusher and a bright slutty red lip-gloss. My long blond wig went on with some large gold hoop earrings, I felt fantastic. A generous spray of Chanel perfume, I felt so sexy. I slipped on the shear hold ups that I had brought the previous day up my silky legs. I lay on the sofa and began stroking my by now stiff cock and gently fingering my arse. I was in heaven, I just couldn’t help myself and reached for a gold 7 inch vibrator out of my bed side draw, a quick squirt of lubricant and I had it buried deep inside me and frantically slid it in and out as I laid on my back until I sprayed hot cum all over my tummy. Wow, what a powerful orgasm as I lay back with my head spinning and my cock throbbing. I couldn’t wait to have a man inside men doing it for real, just the thought of it instantly recharged my sexual desire and I went to the wardrobe to select something to wear. Very high heels and a very short dress are a must. The stiletto sandals brought yesterday are perfect and a black very short silky nightdress in a size ten that clings to my skinny body would be deliciously slutty. The nightdress only just covered the tops of my sheer black hold ups and my black velvet bra with my little c cup silicon boobs gave me a lovely feminine shape.
Well they say time flies when you are having fun and before I knew it was eight o’clock and time for my photographer to arrive. I nervously paced up and down in my heels waiting. At ten passed came a knock on my door, and with my heart racing rushed to open the door. I opened the door and before me stood a an Adonis, I just melted inside when I looked into his eyes, maybe I was delirious but I just felt my heart leap. Come in, “I’m Tara”.” Hi Tara, he said, you look absolutely stunning, my fantasy woman”. “Thank you, Simon”, I said as he walked into the flat from the hall. He smelt gorgeous and I just wanted to grab him, snog him and suck his cock there and then.
I could not believe this was happening, I felt a deep desire within me that I had never felt before.
Can I get you a drink? I asked as he made his way into my small kitchen, Yes, a beer would be nice. As I walked out of the kitchen I could feel his eyes looking me up and down and grabbed a can of beer from under the table in the living room. Your going to look fabulous in these photos, you are very sexy. Thank you, I said as I walked towards him with the beer. As I approached and handed him the can he reached out and put his hands on my hips, pulled me towards him and kissed me gently on the lips. Wow, what a sensual and sexy kiss, my heart pounded as I looked into those dark brown eyes, I instinctively stroked my hand down the front of his trousers and felt his shaft thickening. He smiled and pulled me towards him again and our lips locked in a frenzied French kiss with our tongues exploring each other’s mouths. My hand was now undoing his trousers and I slipped my hand into his underpants and felt his hot fleshy and by now hard cock and began stroking it. Our lips parted and I smiled at him and led him by the hand to the sofa and pulled his trousers down and sat him down with me kneeling in front of him. I bent forward and took his cock into the back of my mouth and was in heaven as I slid my lip glossed lips up and down, doing what felt so natural. He was moaning in ecstasy as I quickened the pace of my sucking and slurping on his thick shaft. Oh, Tara, I am going to come and his body bucked and he grabbed my head and thrusted in and out of my mouth as thick hot spurts of spunk flooded over my tongue and dripped from the corners of my mouth. Oh god, I enjoyed doing that, I felt so sexy. I felt so turned on. I loved sucking cock as it excited me so much, I couldn’t help myself but grab my own cock and wank it furiously, Simon pulled my hand away from my cock and said wait a moment, you will enjoy this more. Stand up and take your dress off, so I did and just stood in my bra and hold ups with heels, he stood up and he kissed me full on the lips with our tongues in each others mouths, he bent me over onto the sofa and without warning slid his shaft deep into my already lubed arse, I moaned as he entered me deeply and I felt so slutty, he started thrusting his cock deep in and out of me and as he did so, reached round and began wanking my cock, within seconds I sprayed all my cum all over the sofa and could feel Simon pace quicken as he spunked deep into my arse.
It was the sexiest experience of my whole life, we sat and smoked a cigarette and had a drink. Tara, you are so sexy, I loved fucking you, it was so exciting, like something so naughty and forbidden. I have fantasised about it many times.
Me too, I have thought about it non-stop for years and you have fulfilled my sexual fantasy for me, thank you. I couldn’t resist it and leant towards him and gently started stroking his cock. I looked into his eyes and I could feel it stiffen in my hand. We kissed passionately and he was smoothing his hands up and down my shear black hold ups and then pushed me back on to the sofa and took my cock into his mouth. You love this don’t you, you’re a girly little slut and you want to be used,
Oh god, he was so right, within seconds of him sucking my cock seeing his masculine body in front of me I couldn’t stop my self and my cum sprayed out into his mouth. I was in absolute heaven, the most exciting sex I have ever had and feeling the most feminine satisfaction I could have ever dreamt of. Wiping the cum from his lips he kissed passionately, I could taste my warm cum on his tongue.
We smoked another cigarette and chatted for what seemed like hours and arranged to meet again, meet again we did and It was simply horny, I will tell all next time.