Mandy's Day Out

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Amanda experiences full sex as a woman for the first time.
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I am a transvestite with a chosen name of Amanda. I have been fortunate enough to have experienced some of the things that other women wannabees and some women can only fantasize about. I only hope that fate is kind enough to me again in the future and that I can experience those forbidden pleasures that are enjoyed and taken for granted by those lucky enough to be female!

For as long as I can remember I have always enjoyed dressing as a girl, experimenting with makeup and trying on a new frock, skirt or top. My wardrobe and accessories have grown over the years and I now have a vast collection of outfits as well as wigs, and false boobs. I am also lucky enough to have a very special female friend named Hannah who continues to guide and encourage me in my desire to be as feminine as a woman like myself can be. The enjoyment of dressing alone had far predated any desire to have sex as a woman and I hadn't really thought about it until my early twenties. I think the thoughts first started teasing with my mind when I worked away on occasions with different groups of guys. We all lived in one accommodation block and there seemed to be a constant stream of porn films each evening on the lounge TV.

It was whilst watching some of these "classics" during the early '80s and sat with a big group of guys that I can remember starting to feel a little jealous of the pretty female models. All of the attention they were getting, not only from their co stars but from the guys in the room with me! How many guys had a hard on because of her? How many had a hard on because they wanted to be her? Well there was at least one who longed to be her! After this experience the desire to not only dress but the desire to be treated as a girl during sex just grew and grew. I wear a skirt when I can and I love everything that entails, so why not just enjoy other feminine pleasures occasionally? Just be the girl I am!

A little while ago I was lucky enough to arrange a meet with another transvestite woman with whom I had been chatting online and one of her tranny girlfriends. The date was set and as it approached I could feel myself becoming more anxious, nervous and excited. What would I wear? How would I feel dressed as a woman with others? What would happen? One thing was certain; Alison had certainly inspired me with confidence and had been very sweet and friendly during our chats. It had been hugely satisfying to have girl to girl conversations ranging from make up to the weather! My mind was set I was definitely going to meet her.

On the morning of our meeting I still had no idea what I was going to wear. I selected a large travel bag, and carefully selected half a dozen of my skirts, these ranged from tarty mini, long black, to full 1950s poodle with layered lace petticoat. Also into the bag went various blouses, panties, bras, lingerie, stockings and tights. I packed two wigs, one short one long and my false boobs and makeup bag. I chose two pairs of shoes, one pair of flat court shoes and the other a gorgeous and very sexy pair of high heels in black patent leather.

Throwing the bag into the back of the car I drove towards the town where Alison lived, I didn't even have her address but I had her phone number and she informed me that she would give me her address when I got to a certain landmark in her town. I realized that this was a safety precaution and that she was probably as nervous as me.

On arriving in Alison's home town a couple of messages were exchanged and I was soon outside a smart house in a residential suburb. Would I be able to walk up the driveway with my bag of girls' clothes and accessories? Would I have the nerve? A further message was received by text saying she could see me and that I should come on up to the house. Without hesitation I grabbed my large bag and headed up to the front door.

The door was opened by a very pretty transvestite who I recognized straight away as Alison from her photo in the chat room. She wore a short black skirt with black stockings heels and a white blouse. She was tall, thin and very attractive with shoulder length black hair. Standing behind her was another transvestite girl named Hayley who was also very attractive in her black Lycra mini skirt and white blouse and heels. Hayley had short blonde hair and her makeup as was Alison's was very professional.

I was welcomed in and was shown to the stairs and a room in which to change. I climbed the stairs feeling both anxious and excited as I unzipped my large bag. I decided almost straight away to wear my 1950s rock and roll outfit. This consisted of a black blouse, bright yellow full circle poodle skirt with poodle design in sequins. This would be complimented by a four inch elasticated belt, fishnet stockings and black heels. Beneath this I chose to wear one of my black bras with black mini French knickers or boy shorts and matching suspender belt as well as a white lace petticoat with over twenty five yards of nylon to puff out the skirt. I also chose my short black wig.

I stripped off and slowly got dressed, pulling the black panties slowly up over my shaved legs and around my hips. Next I slipped into my bra and false boobs before fastening my suspender belt and slowly rolling the stockings up each leg. At about this time the door knocked and a smiling Alison handed me a steaming cup of tea which certainly got rid of any apprehension left in me if at all there was any left at this stage.

After a quick sip of hot sweet tea I popped on my blouse, followed by my petticoat and then my favourite and most treasured skirt. I sat and applied a little make up before arranging my wig and popping on my high heels. I looked at myself in the mirror and wondered what my host Alison and her friend Hayley would make of me. I made towards the door and slowly descended the stairs towards the lounge.

As I entered the lounge I was greeted by the two sweet women who had greeted me earlier. Both commented on my appearance and choice of outfit and we had a short chat about our clothes and make up. I felt totally relaxed in the presence of the two girls. As we all sat in the lounge Alison suggested we watch her new shemale DVD and wondered if we Hayley or I would like to see it. Within moments the television flickered into life and a group of women appeared on the screen.

Alison sat to my right and Hayley to my left upon the sofa in the very comfortable lounge. I can't remember for how long the movie played but before long Alison and I were looking into each other's eyes and our lips met. As her lips met mine I felt a spasm jolt through my body, our tongues entwined and lips played in long deep slow passionate kissing. The feeling was electric as our hands explored the lines of each other's bodies over our clothes. As we kissed I felt dizzy with pleasure, I could feel my hands running up and down her sides then over her breasts and all over her hips and stocking clad legs.

Spasms of pleasure shot through my body and very soon my hands were slowly moving up her nylons and up and under her skirt, over her stretchy tight panties. As we kissed my hand slowly explored further running over her swollen gorgeous balls and her rock hard cock. I was in heaven.

We kissed and caressed and in the heat of passion I was aware that I had pulled up her short skirt and was pushing my hand into her knickers. At the same time I was aware that Hayley was stroking my leg whilst watching Alison and I frolic in deep passion. Still kissing like only excited new lovers can Alison's long athletic cock was in the grasp of my hand. Slowly and softly I stroked her hard wet warm cock backwards and forwards in a soft carousel type motion as our tongues danced.

I slowly withdrew my lips from Alison's and very naturally started to kiss down her blouse, kissing her tummy through her skirt as I continued to slowly wank her gorgeous tool. Whilst going down on Alison I was aware that Hayley had her hand well up my skirt foraging her way into my knickers. Hayley took hold of my solid cock and she began to slowly wank me. By now my feminine instinct was in total control and I naturally kissed the tip of Alison's cock. I began by teasing her beautiful hard purple tip with short, slow kisses and licks, running my tongue down the shaft whilst gently squeezing her beautiful shaved balls. The scent of hard hot wet cock driving my womanly desires to place my cherry red lips around her, taking her deep into my mouth naturally as a woman I long to be.

Meanwhile I could feel Hayley pushing up my skirt and petticoat. Her hands were running up and down my legs, which naturally opened in response. Alison moaned in pleasure as I sucked her gorgeous stiff shaft, my tongue swirling around the swollen head as I took the full length in and out of my mouth like a slut on heat, so willing to please. Hayley soon had my knickers off and around one leg and I felt a warm wet tongue and her soft lips run the length of my own stiff cock as she went down on me, sucking me slowly, softly and passionately as I continued to suck Alison.

After about ten or so minutes I slowly withdrew my lips from Alison's cock and sat up. I can only describe the feeling I have whilst sucking cock as one of delirium. My head spins and I feel dizzy with pleasure. For me it is one of the greatest pleasures I have experienced and hope I can get better at it as I become more experienced in the female role.

After I had sat up, I immediately moved onto the floor, swapping places with Hayley who moments before had been between my open legs sucking me. Hayley moved onto the sofa sitting next to Alison. Both began to kiss as I took hold of both girls' cocks, slowly wanking each with equal attention. It didn't take long before natural instinct directed my lips around Hayley's thick uncut rod. As I sucked Hayley, I was able to run my tongue under her foreskin as her cock moved in and out of my mouth, something else new to me as I had only sucked circumcised cock up until now. Soon both girls were on their feet in front of me their skirts around their waists. I knelt on the floor in front of both with two fabulous erect cocks in my face. Just like the girls in the porn films I sucked and wanked each in turn, enjoying every second of total pleasure. I felt like I was the luckiest woman in the world.

I don't know how long this went on for, but after a while I was gestured up and Alison took me by the hand towards the stairs. Once at the top of the stairs I was guided towards a bedroom and a large double bed by the two girls. I knelt onto the edge of the bed as Hayley maneuvered herself in front of me, her gorgeous stiff cock waving about in front of her black mini skirt. Alison was standing at the bottom of the bed putting on a condom. As Hayley moved in front of me on her knees on the bed I again took hold of her cock and wrapped my lips around it. As I sucked Hayley in front of me I could feel Alison's hands rubbing my ass and then a spasm of pleasure as a wet finger start playing around my ass as she slowly and gently started to finger me and prepare me.

As I continued to suck, my head bobbing back and forth up and down and around Hayley's throbbing thick cock Alison's fingers moved slowly inside me sending shivers of pure pleasure throughout the length of my body. Suddenly, I felt what I knew to be a hard cock toying around my ass. Alison moved it up and down between the cheeks of my bottom, teasing me as she paused occasionally as I sucked cock like a true tart.

I didn't have to wait too long before I felt the hard purple head of her cock slowly pushing into me. The slight pain I felt initially was outweighed by the feeling of delirium of living through my feminine desires. Slowly, Alison thrust deeper and deeper into me as I sucked her friend. Although I have been lucky enough over the years to become proficient at giving a decent blow job with the help of two decent guys I had never experienced full sex as a female, something I had always longed for. What a way to lose my cherry, being the girl in a spit roast. I still can't believe my luck!

Alison held on to my hips as she slowly and gently fucked me. I can truthfully describe the pleasure as the most satisfying sexual experience of my life. Spasms of pleasure shooting through my body with every thrust. Very soon I was comfortable enough to buck back onto her cock, meeting her strokes and matching this with Hayley's thrusts into my mouth. The pleasure continued to build until I felt an explosion deep inside as my muscles or g spot or whatever went into a complete and utter overdrive. In the end I had no control over the most powerful orgasm I have ever had, electric spasms off and on causing me to lose all feeling and control whilst experiencing total pleasure. As a result of my orgasm I was by now flat on my tummy on the bed, still sucking Hayley. Alison managed a few more deep thrusts before moaning in pleasure as she came, as she did so slapping the cheeks of my ass. She pulled out leaving my ass in a state of numbness. Hayley gestured for me to stop as she moved away and off the bed.

I lay on the bed face down for a minute or so, burnt out from the total sexual satisfaction I had experienced. Hayley was putting on a condom and once it was on she gently slapped my ass which I raised towards her by going onto my knees. Her cock entered my swollen lubed ass easily and I was fucked doggy style for about fifteen minutes with my skirt and petticoat around my middle. By now Alison had cleaned herself and was sat on the bed beside me. As Hayley fucked me Alison gently squeezed my balls and slowly wanked me. Again I felt my reward building deep inside as my ass once again exploded into orgasm. I lost all control of my legs and flopped onto my front as Hayley finished me off.

I suddenly realized that I had just experienced the two most powerful sexual orgasms of my life and that I would have been more than satisfied if it were to end there. I rolled onto my back as Hayley straddled my face in order to 69. Her cock eased naturally into my mouth and I could feel her take my by now semi cock into her mouth. I was also aware that Alison was kneeling at the bottom of the bed. Each girl took turns in sucking me as Hayley gently fucked my mouth. Both girls continued to suck me in turn, squeezing and licking my balls. I could feel myself building up to cum before shooting a hot stream of cum into one of the girls' mouths. Suddenly I felt Hayley's cock pulse deep inside my mouth, I was under her total control as she had her weight on me. The first gush of cum shot deep into my throat, taking me by total surprise. Hayley continued to spurt and I was worried I might drown in cum as she came so much for so long I felt as if I couldn't swallow it fast enough! Luckily for me the torrent eased and she slowly rolled off me.

Hayley and Alison had enjoyed a long slow kiss after I had come into Hayley's mouth. It was only fair to share some of the treat I had just experienced. After slowly kissing both girls slowly and passionately for a minute or so each I collapsed on the bed in a heap, exhausted. My make up messed up, my lipstick smudged, my knickers still around one leg!

I showered had a lovely cup of hot tea and said goodbye to the girls.

For days after my experience I felt a nice warm little ache deep inside my ass. I also realized that I really did enjoy having sex as a woman more satisfying than any other experience I have ever had and that I had experienced total sexual satisfaction!I could even enjoy this total satisfaction without touching my cock making it redundant unless my partner wished to play.

So, my resolution from now is to enjoy more time as Mandy, wear nice clothes and be a woman when I can!

Bring on a boyfriend! Boys I'm waiting!

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3 Comments
AnonymousAnonymousover 7 years ago
I want a man's cock too

I'm a crossdresser and even though I've been with other CDs but I much prefer having a real masculine hunk of a man feed me his cock and fuck my man-pussy deep and hard. I love being called a "sissy bitch", a "faggot cocksucker", etc because that's what I really am.

I'm looking forward to reading more of your stories.

AnonymousAnonymousabout 13 years ago
A girl needs a man'c cock

I'd much prefer if it had been two muscular hunks. A feminine girl needs real male cock.

Anna

AnonymousAnonymousabout 14 years ago
Great

Loved it!

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