My First Girly Fuck

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My First Girly Fuck

As I awoke my hand rubbed lightly over my rock hard cock. I was wearing my favourite pale pink satin panties and matching bra, my body was completely hairless and smooth and I was feeling very horny.

Aged about 13 I had opened my mother’s underwear drawer and discovered the delightful feeling of ladies undergarments. I remember clearly my desire to slip on a white lacy Playtex control girdle and nylon tights and the feeling that the smooth material gave my young body. As I stroked the bulge in the tights my dick was instantly erect, my helmet was bright purple and after only a moment there was a huge wet cum stain on the front of my mothers tights, cum was dripping down my leg and onto her bedroom carpet. She never mentioned this or the numerous other stains that appeared on her panties tights and girdles during my teenage years, did she know?

Since that day I have regularly dressed to be as girly as possible and now this morning I am in bed next to my gorgeous partner who accepts my need to be feminine and is happy for me to dress. She has helped me to expand my collection of girlie clothes in order that I don’t have to borrow too much from her wardrobe and so the bra and pants are my very own, I gently caress my dick and balls and marvel at the sensation, to this day at the grand old age of 51 I still love the amazing electric tingling feelings that shoot through me. The look I can create with stockings, a basque and falsies turns me on every time I dress. The feel of make-up on my face and the smell of my Chanel perfume drives me crazy.

There are not many weeks when, on my days off I am not to be found glammed up whilst my partner Michelle is at work, finger and toenails painted eyebrows plucked and dressed as slutty as possible.

Yesterday afternoon whilst dressed in black nylon hold-up stockings with wide lacy tops, my huge four and a half inch stiletto boots, chiffon mini skirt the pale pink undies I awoke in today and a shiny boob tube I had done the housework and prepared our evening meal. With everything tidy and the table laid I looked forward to her coming home and finding me. As her car drove up the hill I poured a glass of her favourite merlot, I have left the front door ajar and she steps inside, I kiss her full on the lips, my lipstick smears over her beautiful face and she knows I want her straight into our bedroom. Michelle turns and says, “so Dee are you feeling a little sexy tonight”, this is of course the understatement of the year!

Michelle is a beautiful girl with very large tits; my hand reaches out and cups her right breast, as I gently massage her nipple through her blouse it hardens between my fingers. I fumble with the buttons of her blouse but soon have it and her bra loosened to reveal her magnificent boobs, I lower my head and take her nipple in my mouth, there is now bright red lipstick smeared over her dark pink aureole, I lift my lips to meet her soft wet mouth and we kiss long and passionately. Although I have tucked my cock back under to give a smooth line in my silk pants I feel it stir, as we kiss Michelle’s hands move over my body she is now rubbing my left tit and right bum cheek, this attention is too much and I feel my dick straighten and create a tent effect in the chiffon skirt I am wearing, Michelle reaches for my dick, squeezes it gently and whispers in my ear “oh baby I love this sissy dick and I want it in my mouth now”. With this she slowly sinks down until her face is level with my dick, raises the hem of my skirt and nuzzles gently on the gusset of my pants.
It takes all my concentration to prevent my orgasm from taking me at this moment, my balls are heaving and my left bum cheek is shaking uncontrollably, my knees feel weak. My fingers are gently massaging the top of Michelle’s head as she gently pulls down the lacy waistband of my panties and encircles my cock with that soft sexy mouth, my dick slips into heaven, her tongue flicks over my swollen glands and I know she must be tasting my pre-cum.

Just as my mind thinks that this cant get any better Michelle begins to explore the crack between my shaking bum cheeks. She gently parts them and runs her fingernail up and down my anus; it glides gently as during my earlier preparation I had lubed myself in readiness. The sensations flowing through me were unbelievable, her right hand glided up and down the sheer nylon of my stocking clad leg as the fore finger of her left popped inside my arse. With one thrust the length of her finger was inside, in and out she forced it whilst still licking, sucking and kissing my rigid cock.

On the third entry the muscles in my anus tensed around her finger my balls emptied and I unleashed a huge spurt of cum deep inside Michelle’s mouth, she gagged slightly and withdrew, my second spurt hit her full in the face, dribbling down from her eyebrow into her eye and on down her cheek. She popped me back inside and took the rest of my cum on her tongue. Again she withdrew and opened her mouth to show me the mouthful of white spunk, a tiny drop leaked from the edge of her lip but she swallowed and licked her lips so as not to waste the escaping droplet. She also wiped the glob from her cheek with a finger and swallowed this too.

My orgasm was calming now and I realised my arse was still gripping her finger, as I relaxed she eased it in out again and massaged my cock gently. Bending I kissed her and tasted the salty sweetness of my cum on her lips. In one move I lifted her gently onto our bed turned her onto her belly and reached under her work skirt to remove her tights and knickers. She raised her bum so that I could rim her arse for a moment and then I took her doggy style from behind. Her pussy was soaking and my slightly soft cock slid in quickly. As my balls slapped on her bare arse I felt my stocking tops rubbing against our bodies, the soft chiffon skirt tickled my belly and my dick was hard again to give Michelle what she needed. Fucking her for a few minutes I could feel her body tensing as she neared her orgasm, I reached for her right tit and tweaked her nipple hard and with this she collapsed onto the bed and screamed that she was cumming. I held her as her orgasm racked her body and gently subsided, her head turned and she said she loved our lesbian sessions so much. Wow what a girl, I feel so lucky.

This wonderful session had happened because I am a greedy slut and I crave more.

Yesterday morning once Michelle had left for work I had gone into town to find it.

Wearing a bright blue satin basque with black lace trim and wide suspenders supporting a pair of silver coloured tights, my 36c breast forms filling the top and a thong, which matches the basque, I pulled on a pair of my own loose fitting jeans and a white shirt. The underwear was visible through the shirt but I also wore a jacket and I figured that with this unzipped I could have it open or closed as needed.

At a café in the busy centre of town I ordered a coffee and sat people watching, several guys caught my eye and smiled at me, were they interested? None of them stopped to chat and so I wondered away.

Needing a pee I entered the public loos and was soon joined at the urinal by a black guy aged about 30. He stood close and so I lowered my jeans as much as I dared to reveal my thong and stocking tops. Glancing over I could see his dick peeing a huge spurt into the urinal. I longed to reach over and touch him but was nowhere near that brave. I am certain he knew I was interested but he fastened himself, rinsed his hands and left.

Leaving the loos I walked across the car park, which was strangely empty for the time of day. There was one large BMW in the middle of this area with no other cars around it. From a distance I noted that there was a man in the drivers seat who had made a bit of a flourish with a newspaper that he folded and placed on the dash in front of him as I was approaching his car. We made eye contact and I smiled, he smiled back maintaining our eye contact. I changed direction slightly to walk closer to his car, he looked about age 60ish with smart grey hair and a nice shirt, he was still smiling at me, could something I have longed for for so long be about to happen? As I reached the bonnet of his car I slowed my pace and as I walked past the passenger window I looked directly inside. The driver had his trousers and underpants lowered, his shirt pulled up over his belly and was wanking his cock slowly. and I saw that his helmet glowed. He was still smiling. Walking past the car I made an instant decision that I wanted to speak to him and see what would happen. So I walked around to the drivers window, which was firmly closed but he continued to smile at me, I said and indicated that he should open the window. The look on his face was one of concern; I guessed that he was thinking would I want the same as him. After a moment he dropped the window an inch and said “hi”. I leaned closer and told him that I loved the look of his long cock and would like to take over stroking it for him. He then voiced his concern that he was unsure and wanted to know he could trust me. Instantly reassuring him I said I was out hoping something like this may happen. He smiled again as I opened my jacket, lowered my shirt and revealed my breasts to him, he opened the window fully. Bending slightly I whispered into his ear “I hope you can cope with a slutty tranny whore” My left hand was on his neck as my fingers ran through his hair. My right hand reached through the window and grasped his engorged knob. He gasped and whimpered that he would try to cope!

After a few minutes he told me his name was Jim and suggested that we move to the public loos I had just been to. I told Jim that whilst I was very much looking to have sex with him I was not wanting to have my first experience in a grotty cubicle. With this he quietly said that we could go to his hotel room to which I agreed readily. He told me the name of the hotel and I agreed I’d meet him there in an hour.

Driving home to change into a pair of skinny jeans, huge heels and a lycra boob tube to show off my tits. I covered these with a long coat and with great anticipation headed for Jim’s hotel. Pulling up in the car park I applied some eyeliner, mascara and lipstick and eased into a long brunette curly wig. Oh my god I felt so horny, I hoped that Jim had not changed his mind, I needed that gorgeous cock inside me, I wanted to taste his cum and to kiss those lips. Would he need me to dominate him or would he treat me like a lady, the anticipation was driving me wild. Jim had mentioned that his room, number 35 was accessed from a corridor immediately inside the hotel lobby and that I should not need to speak to the receptionist, even with my huge longing for the sexual experience I hoped was about to happen I was so nervous entering the hotel. At the front door a family of four where leaving with their luggage as I approached, the father held the door and his two young children skipped outside, he gestured for me to enter and I saw him do a double take as he realised I was a tranny dressed as a whore. With a huge smile I walked past feeling his gaze follow me in, his mumsie looking wife tutted and said “come along Mike the girls have gone”. The receptionist was a pretty young blond who glanced up and asked if she could help? My nerves were taught and I felt my face blush, stammering I managed to say “no thank you I am meeting a friend”, and turned left into the corridor as Jim had instructed. Thankfully I passed through double swing doors and left the reception area behind. Looking at the room numbers I calmed and swung my hips sexily down the corridor soon arriving at room 35.

Knocking gently I suddenly felt unsure, could this be a set up, was I about to be trapped alone in a room with a madman who hated cross dressers, should I flee back to reception and the safety of my car but it was too late as I heard movement from within the room and footsteps approached the door. As it swung open Jim was smiling at me, dressed in a light linen suit a fresh shirt open at the collar and soft comfortable shoes he looked the perfect gentleman. “Please come in” he said “I am feeling very rude as I did not ask your name?” Entering his room and introducing myself as Dee I heard Jim breath out slowly as his eyes took in my 4-inch stiletto heels, stocking clad legs and false tits pushing out from my basque.

“Drink?” Jim enquired softly, I turned toward him as the door closed, “in a moment” I purred my left arm slipped around Jim as I pulled him to me and found his slim and firm bum cheek, I looked deep into his eyes and saw raw desire, I relaxed, this was not to be some scary set up but a sex fuelled afternoon of fantasies fulfilled. Our lips brushed gently as I asked for a large red wine and moved further into the room away from Jim. Behind me I heard the wine poured into glasses, I opened the net curtains and looked out onto the car park as Jim handed me a glass of red, taking one mouthful I placed the glass onto the windowsill. Turning to face him I grabbed Jim’s dick through the linen of his trousers and instantly he was hard in my hand, fumbling with the excitement I released his 8 inch cock and stroked the thick veiny shaft, “this whore wants to suck your cock and taste your cum Jim” I purred into his ear, he firmly placed a hand on my shoulder and pushed me down towards the magnificent dick in my hand, I raised his shirt and ran my hands over his firm stomach, “this guy is in excellent shape” I thought. Suddenly he become more authoritative and said “come on bitch get my cock in your mouth now”, I kissed his helmet and tasted pre-cum on my lips, allowing him into my mouth in one long stroke until the length made me gag I began to work his dick in and out. On the third or fourth entry my throat relaxed and he slipped deep inside until my lips were at the base of his shaft and his balls slapped under my chin, I bobbed my head up and down to massage him inside my throat and felt his cock swelling as he moaned loudly and grunted “oh fuck baby, suck me, suck that cock”. I eased his helmet back into my mouth and used my tongue to great effect on the tip; again I tasted his salty pre-cum and felt him throbbing.

All this time my hands were eagerly massaging his belly and bum cheeks and now I spread his arse gently and ran my fingers over his anus probing quickly and gently allowing the tip of my finger to penetrate him just slightly as I did so. Tipping my head upwards whilst still sucking I looked at his face, with mouth open, eyes closed he looked totally wrapped up in the exquisite feelings occurring in his cock and arse, as I watched he must have subconsciously realised and his eyes opened and locked onto mine, “you are one horny bitch Dee” he moaned “and I want to fuck your pretty arse girl, are you ready for some hard cock up you?” I nodded eagerly and wondered if I could really take eight inches of his hard cock up my arse, which had only previously experienced carrots when they looked like cocks and my Anne Summers, Twist toy. This is eight inches long consisting of six balls joined together with a very small bead at the tip building to one about the size of a golf ball, if my arse is well lubed it will all fit inside. However Jim’s huge member starts with a helmet the size of a golf ball!

Whilst I’m thinking all of this Jim removes his cock from my mouth and lifts me to my feet, I realise that we are still in front of the open window and he has been on view to passers by whilst I have pleasured his cock.

A smear of my red lipstick runs the length of his rock hard cock and he tells me “your lippy will be smeared over your love hole very soon baby girl”, he instructs me to bend over and grab my ankles and I immediately feel that huge helmet brush between by bum cheeks, which he grabs apart roughly and presses his member into me. Although I have greased my crack this morning nothing happens for a moment, Jim releases his pressure into me, spits on his dick and pushes again. This time my arse opens and with one unrelenting thrust Jim pushes 8 inches of rock hardness in until his belly meets my bum cheeks, I squeal loudly and beg him to stop but he withdraws fully and rams back in again and again. The taste of salty tears mixed with my black mascara steaming down my cheeks into my mouth make me realise that the pain is subsiding and that as he gets into his stride my body is responding to the rhythmic fucking Jim is giving me. Again I hear him moaning softly and he tells me I have a beautiful body, turning my head I smile, thank him for the compliment and say “it feels beautiful with you pounding my hole like this, please don’t ever stop”.

Jim continues the hard fucking for another five minutes or so throughout which his penis massages my prostate gland and my own dick is now rock hard, whispering over my shoulder I ask Jim to play with my cock as he fucks me so that I can cum with him. Of course he obliges and within moments I feel his rhythm quicken, his helmet swell and his body lose control as he fills his pink ribbed condom with spurt after spurt of warm cum. At the very same time I could hold back no longer and Jims hand was showered with my spunk too, my legs gave way with the ecstasy and I sank to me knees ripping his now softening penis from my arse with a lovely “plop” sound.

Whilst I thought this would be the end Jim had other ideas he removed his condom told me tip back my head and open my mouth, “drink this bitch,” he said “like the real slutty tranny whore you are”. The still warm cum dripped onto my tongue it tasted sweet and salty at the same time, I swirled it around my mouth enjoying the feel and taste and swallowed every drop. As Jim stood in front of me I again took him into my mouth and sucked the last drops of cum from him.

Unsure whether I could stand I tottered up onto my heels and sank down on the bed and slid beneath the cool sheets, Jim moved in beside me and held me in his arms, we kissed passionately and he told me he had never experienced sex like this and how he hoped we could meet again, I readily agreed and asked if we had to leave, “no” he replied, and so we cuddled and chatted for an hour before he fucked me a second time, this time he withdrew and shot a small amount of his lovely cum directly into my mouth.

Recovering my clothes I dressed quietly touched up my make up so that I could walk to my car and left, taking warm sexy memories of the afternoon with me. Jim’s mobile number was added in my phone ready for the next time.

On the drive home my dick remained hard and I knew I would have to shag Michelle this evening when she arrived back from work ……….

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My First Girly Fuck, 9.8 out of 10 based on 6 ratings

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