Although I'd never been with a man before, my online chats and contacts usually ended up being with men - they seemed to be so much more horny and available than women. Either I was doing something wrong or women weren't into online sex all that much! Anyway, for years it's always been a hobby, an indulgence if you like, never turning into real contact, just a fantasy that I look forward to playing out whenever I get the chance.
I'd consider myself pretty much straight but curiously have always enjoyed the feel of lingerie and hosiery on my skin. I used to wear my mother's when I was alone in the house and the feeling of sexuality charged through me like an electric shock. I loved to lay naked on the bed in a pair of her suspenders, stroking the sheer nylon as I masturbated, always cumming very quickly.
That was years ago now although my online contact had, like I say, edged more towards the men who seem much more responsive. I'd also thought about what it must feel like to suck a cock, a thought which also turned me on immensely. I knew too from fingering my bum just how nice it would feel to have a cock in there!
Lately I've been talking to a man, well a transvestite, online on a gay website. Our chats have been getting increasingly erotic. He's a 'slut' in that he has no standards, just wants to dress as a woman and be any man's whore. The thought turns me on incredibly as I have also fantasised the same thing from time to time. Anyway, this man turned out to live only about half a mile away and I was constantly wanking off imagining going round to his house. What was even more of a turn on was that his wife knew he did this with men! She wasn't too interested but let him do it.
One night we were talking online, I was alone in the house and naked on the bed with my laptop. He was asking if I would ever come round for real. I made the usual excuses as I'm far too nervous for real meets and loved the fantasy element. I did however let him into my latest fantasy. His TV name is Jackie and I'm Jim. I asked him if he'd be interested in my fantasy.
'I'm a slut and will do anything for your cock, Jim,' he pleaded.
I was hard as a rock from him saying this, so I said, 'Well, darling Jackie, I have fantasised about you so much lately. What makes me cum really hard is the thought of you sucking me off while I wear your wife's lingerie. Would you be up for that?' my heart pounded as I waited for a response. Would he let me wear them? Would it turn him off?
'Yummy, that would be lovely! x' he replied. I thought 'Wow, this is sexy!' his agreement made me so horny I started pulling my shaft, imagining the scene.
'Are you free now?' he asked.
Now I was trembling, thinking this horny scene could be real and I was only a 10 minute walk from his house. 'I am darling x,' I replied, still with no real intention of following through.
'Then come round now please, darling Jim. I'm SO desperate for your hard cock in my mouth xx.'
I couldn't believe this was happening but a wave of lust overcame me and I allowed myself to believe I would meet him for real. 'What's your address, Jackie?' I asked. I had no reply for a minute or so. '?' I prompted.
Then after a few seconds Jackie said, 'Would you really come round? Aren't you a timewaster?'
I was hurt but he was kind of right. I was mad now as well as turned on, a weird feeling. I replied, 'For you darling Jackie, anything. Tell me your address and I'll be round in 10 minutes.'
'If you don't turn up then I'll never speak to you on here again,' he threatened. 'I don't give my address out to timewasters,' he added.
This threat pushed me over the edge. 'Jackie honey, you know I won't risk not having our horny chats in the future, if you tell me your address I promise to come round,' I pleaded, with butterflies in my stomach.
Another long delay, then Jackie replied, 'OK Jim, my address is 14 Swithern Terrace. You know where it is?'
At last I had Jackie's address, and I certainly did know where it was! I could be there in 5 minutes, never mind ten! I asked Jackie, 'OK, I'll be round ASAP. Do you promise to be discrete and do you promise to be as feminine as you can? xxx.'
I was still uncomfortable about meeting a man and wanted to make sure I could pretend he was a woman, albeit with a nice fat juicy cock!. He replied, 'Of course, Jim, there's nothing I love more than being a horny, sexy feminine woman. Get round here now, I want you! xxx,' and with that he signed out of the chartroom.
'This is fucking it!' I thought. I was literally trembling with excitement and desire. I was about to meet this hot sexy woman (I decided now that I would start thinking of him as a woman as much as I could) and wear her wife's lingerie! I raced to the bathroom to give my cock a thorough wash, I wanted to be perfect for her. While I was at it I also washed my bum hole, just in case.
The walk to Jackie's house seemed to take forever but soon enough I was at number 14 and pressing the doorbell. I could see her approach through the frosted glass, my excitement mounting. She opened the door and greeted me silently with a large smile. I think she was pleased with me! She motioned me in and closed the door. We stood face to face, she was nervous but not as nervous as me. I was just one of her many men now, although the newness of me obviously had her excited.
I looked her over and was pleased at how feminine she was. A hot, lusty MILF but with a bonus down below. Her long dark red hair spilled down onto her shoulders and the heavily made up face pouted at me with big, luscious lips. The hunger in her eyes was turning me on so much 'H..h..' I stuttered, trying to say hi.
She just leaned in and kissed my ear, whispering, 'Like what you see, darling?'
She stepped back in the hallway and motioned me upstairs. 'Let's get you upstairs and properly dressed,' she purred. I followed her up in a trance, my heart racing and cock straining in my trousers. We went into the bedroom and she told me to lay on the bed while she did me a little show. What a show! I now appreciated her feminine curves and lovely figure, she turned her back to me and slowly gyrated her hips and arse.
She was wearing a dressing gown, which she let slip to the floor, revealing a pair of long, lovely legs and a wide, curvy apple like bottom. I was in awe, it was one of the nicest I'd ever seen. I let out a gasp and stroked my cock, trying to fight the urge to cum in my trousers. She was wearing lacy black suspenders and small, black frilly knickers. She turned round to face me, her lips open and tongue circling them seductively. Her hands caressed her pushed out boobs, tummy and hips while I watched, entranced - this was incredible, I felt so lucky and liberated to be here. 'Oh, Jackie,' I said, 'I'm so glad I came, you are absolutely beautiful!'
I could see the bulge in her panties now, her cock looked big and thick, my perfect fantasy. She told me to strip naked, I said, 'What about dressing me up Jackie?'
She replied, 'That can wait, I want you now, as a man. You're staying here all night. There's plenty of time for that,' she demanded.'
'But..but,' I protested but was cut short when she let her cock out of her pants, the semi erect shaft hanging there like forbidden fruit. 'I'm staying all night,' I agreed, my mouth watering at the sight of her majestic bulging column.
I undressed as quickly as I could, my exposed flesh seemed to tingle at every nerve, I'd never felt so alive. Jackie told me to lay down, which I did, my now fully erect cock standing up like a flagpole. She got on the bed and knelt at my feet, kissing my toes, gently at first, before taking them greedily into her mouth while her hands stroked my inner thighs and calves. The sensation was incredible, my cock throbbed and ached with pleasure as she made love to my toes, I was breathless with anticipation of what my cock would feel like in her sensuous mouth, if I was to be so lucky.
Now she turned her attention to my thighs, stroking, squeezing and kissing them like a woman possessed. 'Oh my god, I love your legs, Jim,' she gasped, 'open them wide for me darling.'
I obliged immediately and she dove in, licking my inner thighs, right up to my balls. 'Jim, darling, can I suck your big cock like the slut I am?' she asked coyly.
'Of course you can, Jackie,' I just managed to breathe between gasps of lust.
'Talk filthy to me, Jim, it turns me on so much,' she pleaded.
I thought for a few seconds, this was a new idea to me, then said, 'Jackie, you beautiful woman, I'm about to explode, get your slutty pretty mouth around my hard shaft now.'
That seemed to do the trick, she engulfed me greedily, taking me all the way in, my length entering her throat with every incredible gulp, I was almost ready to cum then I had an idea, as her big fat cock was pressing on my leg. I wanted her in my mouth too.
'Jackie, 69 with me,' I pleaded. She seemed hesitant to release my cock from her mouth but the lust in here eyes told me she wanted it as much as me. She got on her knees, turned her back to me and straddled me, her lovely bottom was lowered to my face and I grabbed hold of her hard, thick cock, the first I had ever touched apart from my own. It was so warm and firm and sticky with sweat, it felt amazing just in my hand.
As I smelled her musk I pulled her into my mouth. I had to open so wide to get it in and now I felt like a slut and understood Jackie's need to be one too. She moaned and pushed further in as I gobbled her up.
As if things couldn't get any better, I felt her hot mouth envelope my own cock again, taking my full length down her throat. I did the same to her, gagging myself on her sex but loving it all the same, the sensations were incredible, her tongue and throat caressing my shaft and cock head while her own juicy length invaded my throat. I squeezed her arse hard, one cheek in each hand. Fuck, it felt good.
Overtaken with lust, I spanked her arse hard, which she loved, moaning onto my cock. I could feel myself ready to cum, that familiar feeling of the start of orgasm, this sent me over the edge and without thinking I instinctively pulled apart her arse cheeks, still with her cock deep in my throat, and rammed a finger in her tight hole. The feeling was so amazingly sexy I moaned loudly and felt my orgasm come, I shot what felt like a bucket full of cum into her lovely mouth, shouting, 'Oh, Jackie, take my cum you whore, take it all,' while still fingering her gorgeous bum hole.
She greedily gobbled me up even more than before, and quickly stood up, her shaft leaving my mouth. She turned to face me with a mouth full of cumin sat on my chest. Her balls bouncing on my chest as she wanked her huge hard cock. With a scream of delight, she came all over my face, slapping her cock end on my cheeks and almost spasming with delight.
Wow. We looked at each other for a few seconds, both of us totally drained by the intensity of our first lustful encounter. We both had each others cum in our mouths. I knew what was coming next. She lay on top of me and gently and sensuously kissed me deeply.
Our cum mixed in our mouths as we kissed and caressed each others bodies. The contrast was amazing - just a moment before we had been lust filled animals, sucking and cumming and throwing our bodies at each other, now we were like two lovers, gently caressing and warming each other with our hot bodies. I stroked her legs and bum, relishing the smoothness whilst kissing and licking her lips, tongue and face, covered in our cum.
We feel asleep on top of each other like that. I awoke about two hours later, almost forgetting where I was but then I saw her. Saw Jackie's sleeping body next to me. Her beautiful figure outlined by the glow of her alarm clock. A warmth and happiness washed over me, followed immediately by a growing sense of lust. The night wasn't over yet, but I'll save the rest for part two.
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<a href="http://www.lushstories.com/stories/crossdressing/my-first-time-with-a-hot-sensual-lady-.aspx">My First Time With A Hot Sensual Lady - With A Lovely Cock</a>