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Crossdresser's first time with a man


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This little true story is about the first time I was with a man and a night that I will never forget. My name is Selena. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in my mother's clothes and feel the soft touch of her satin lingerie, stockings and fur coats on my skin. It's just felt right to me all my life and I guess that's the way I'm programmed.

After many years of just dressing in the clothes I eventually began using make-up and wigs to complete the look and to compliment the wonderful feeling of wearing women's clothes. That evolved to putting pictures of my female self online to be shared with and admired by other t-girls and guys around the world, but that's a story for another day. It was through a photo-sharing website that I made many new online friends who shared the love and celebration of femininity that cross-dressing expresses.

One of these lovely people was a guy called Ben. He was 21, good looking and very polite. He stood out from other guys online who sent me typically desperate, dirty messages with the intention of wooing me without any idea about romance and friendship. Ben was sweet and friendly and we often had a laugh chatting online to each other.

Another lovely T-Girl web friend of mine, Gwen, had often told me about how good it is to be with a man.

She went on at great length about how nice it was to be treated as the centre of attention by a guy; how they doted on you; how they admired you more than regular girls; how lucky they felt to be with you; how they kissed you more passionately than they would kiss a normal girl and how they made you felt so good when they held you so tightly and lovingly that you couldn't even move as you laid in bed ...

She had certainly me got me thinking....I was missing out on a large part of being a girl. So one night while flirting online with Ben I hinted that we should meet up sometime. He said that he was free that weekend and he would love to meet me. It all happened so fast I didn't have time to think so just said yes. That week went so slowly. Every time I thought about Saturday night I felt very nervous and very horny!

I asked him to send me a photo of himself so I knew he matched his profile pic. He sent me a photo of his hard cock! I read the message and instantly my cock got hard. And something happened which had never happened before, my ass clinched automatically as I imagined what it would be like when he would be rubbing that huge cock against my butt ready to enter....

Saturday came and I was so excited! I spent the morning doing my usual routine to prepare myself for becoming as feminine as possible. The first thing I did was have a long hot bath. My body is naturally smooth with very soft skin which I have nurtured since I was a … but naturally I needed to be extra smooth and soft for this hot date. This guy deserved the best experience I could give him and I wanted to put a smile on his face for days and leave him wanting to come back for more.

As I lay in the bath I looked down at my petite feet with pink nail polish on the toes matching my fingernails. The smooth wet legs shimmered from the water and the light on the droplets running down my skin caught my eye.

I looked at these legs and knew that there was nothing to hint at my usual identity as a male. I looked up along towards my crotch where my penis should be but it was naturally hidden between my legs. All that remained was a very small neat Brazilian style patch of tightly cropped bush.

The water glistened on my cute little tummy and my belly button. My body seemed to be completely different way to when I normally cross-dressed and I wondered why that was. I got out of the bath and dried myself off and then it occurred to me. The difference this time was that I was preparing to offer myself to a man for his pleasure and that after tonight everything would be different. There was no stopping it now.

I carried on with my usual routine. I slipped into my 'getting ready' gear. It's all about comfort and femininity while getting ready. I wore a pair of nude shimmer tights, ballet flat shoes, a black bra and a cute comfortable mini-dress. After plucking and shaping my eye-brows I sat down and applied my make-up.

Once the foundation goes on my face I look instantly unrecognisable from my male self. I love that feeling. It's the trigger that tells me that I can release myself completely to becoming female.

I am lucky in one respect with my 'pretty boy' facial features. It does nothing for me in normal life as people, in work and socially, view me as a feminine male but when I dress up the make-up really accentuates the natural feminine features of my face. Although I have never met my mother I am convinced that I look like her but, again, that's a story for another time. Once my make-up was done I changed into my outfit for the evening.

I decided to wear a white mini-dress with black opaque tights and black 5" heels. I love the look and feel of opaque tights. I love how they work well with dresses on any occasion and I adore how great they are for just lounging around home; comfy & very sexy! I chose not to wear knickers as I loved the feeling of the tights on without underwear and I felt it important that I was relaxed whilst I had a guest.

My beautiful blonde wig completed the look. All I had to do now was pour myself a white wine as I waited for my date to come. The buzzer rang and I felt a huge sense of relief to see that the handsome man on the screen of my intercom was the guy from the web profile and not some phoney. Finally, Ben had arrived and the night was about to get a lot hotter.

Ben came to the door of my apartment. He was big, somewhere over 6' tall, with strong shoulders and a friendly, innocent looking face. Normally as a guy, with me being only 5'6", I was naturally intimidated by tall men. Strangely now, wearing 5" heels, I was almost as tall as this guy so did not feel intimidated but I still had to lean up to him to give him a peck on his cheek. That felt so hot!

I led him into my living room and asked him if he would like a drink. He told me I looked beautiful and I felt myself wilt as the words he spoke caught me off-guard and made me weak at the knees. No man had ever told me to my face that I was beautiful and it made my heart beat faster and blush. No doubt about it, he was a charmer! I made him a cup of tea and we sat on the sofa together chatting like old friends. As the night went on I could sense that he was nervous. He told me that even though he was 20 that he had never had an experience with a girl.

I felt sorry for him and asked why. He said that he was only interested in transvestites and that he really didn't have much care for girls. I knew at that point that he was the shy type and that my maturity of 51 years would have to help him to overcome his shyness.

As we chatted I flirted with him, gradually reeling him in. I asked him for his opinion on different shoes I had recently bought as I modelled them for him. We laughed and joked about my height without high heels and I asked him to stand up beside me to compare height. As I stood there he towered over me. I felt so small and demure.

Here I was, dressed as a woman with this real man. There was only one man in my apartment at that moment and it was not me. I was the girl in the situation, without any doubt, and this night was only going to go one way and there was nothing I could do to change the inevitable. I felt something deep inside me change and accept my fate.

I commented on how big he was and put my little hands up against his big hands. He smiled silently, and I knew I was turning him on. I got a little closer to him with our bodies touching. It was then I got a real shock when I could feel his large hard cock erect in his trousers as I flirtingly pressed my body against him. I felt myself helplessly attracted to this fine specimen of a man. Suddenly, he had become the one with the power and I was the pretty little thing with no choice but to surrender myself to him.

I knew how much he lusted for me and I wished to keep that anticipation and build on it until he could not resist me anymore. I cheekily pushed him away and sat back on the sofa in a 'pretend-I'm-not-interested' flirting kind of way. He sat down close to me wanting me more than ever. We sat there almost face to face and I stroked the leg of his jeans watching, and lightly brushing my fingers against, the huge package in his trousers.

I smiled at him and said, almost whispering:

"So what did you come all this way down to see me for?"

"Because you are a friend....a very beautiful friend.... and it's nice to finally meet up with you", he said.

"Is that all?" I asked, "Because right now I think you are really cute!"

I leaned my head closer to his and our lips touched. Immediately, my heart skipped a few beats; here I was on my sofa and kissing a guy and the feeling was electric!! My tongue slipped into his mouth and it tasted so good! He was such a good kisser too, I just wanted more!

My hand moved up his leg and right onto his large cock, now pulsating and bulging under his pants. I half stood up and moved over onto his lap, my slim smooth nylon clad feminine legs straddling his mannish body.

He moved his hands onto my calves and up along my legs and up onto my hips. Helplessly, I rested my elbows on his shoulders, looked into his eyes and smiled. This is exactly what I was looking for but at the same time I thought 'how could this be? I'm not attracted to men!' This was so easy and felt so natural to me.

I kissed him more, deeply and lovingly, surrendering myself to both him and this situation that I've found myself in. I moved my hands around to his strong neck, amazed at how good his cropped hair felt to touch. In all my life I had never known what is was like to feel a man's hair in passion....what was I missing out on all this time?!

I held the back of his head urging him to kiss me more deeply. As our tongues danced it was heaven! He ran his hands around my waist and gently squeezing my butt and I felt like there was nowhere else in the world where I would rather be but there, in his strong arms kissing him.

As we kissed I squirmed on his lap allowing my body to tease his still growing cock. Then it struck me again about how helpless I was right now; here I was 'the girl', teasing this man and luring him to elevate things to something more.

The only thing between his bulging manhood and my girly ass was his jeans and my tights and I felt completely defenceless! I was deeply conscious of how the entire situation was affecting me, and how right this felt.... I loved it and kissed him even more passionately. The night was only beginning....

After a lovely time kissing like teens on the sofa, I slipped back into my heels, stood up and led Ben by the hand to the bedroom. It felt amazing to walk ahead of him, knowing that his eyes were fixed on my body with anticipation as I walked.

I was thrilled at how easy this date was going and felt so excited that even more fun was ahead of us. He glanced around my bedroom:

"You have a really nice apartment" he said.

"Thanks, yeah, but it gets lonely. Nice to have some company for a change", I smiled, as I leaned up to kiss him on the lips enticingly.

"You really should make yourself more comfortable. Let me help", I said as I opened the buckle on his belt while stroking his cock which was now dangling down his inner leg.

He undid his fly buttons and I awkwardly moved his trousers down his legs. His cock bulged through his black boxer shorts and I was amazed about how good it felt to touch. My cock never felt this good when I wore men's underwear and again the sense of submission to this real man overrode my brain and body.

I slipped his boxers down to reveal his manhood. It was huge, 10 inches; thicker at the base with a very large beautiful bulbous head.

I took it in my small hand and was amazed at how a real cock should feel like. It was obvious to me that my little cock could not compare to his and that I was in the natural role as the female and, in reality, should forever be the female as my short cock was effectively redundant.

I lowered to my knees and moved my lips to the tip of his cock which was huge. About the size of a large plum it was bigger than my pretty little mouth. How was this going to work?!

The tip had a large dribble of pre-cum spilling from it which I licked- automatically. It tasted salty and sour, sticky and slimy, weird, like nothing I had ever tasted. It was like ambrosia to my tongue and throat as I swallowed his essence deep into my body to assimilate it with my being making us closer than just friends.

I opened my mouth fully covering his knob and the first 4 inches of his cock, bobbing my head and making my tongue tickle the bottom of his shaft. He groaned from the pleasure of satisfaction after waiting all evening for relief from the anticipation. I licked and sucked like a cock-hungry tease, stroking it and smiling up at him every time I took a breath of air.

I knew that this boy was mine and I wanted to build up the anticipation even more, knowing that a steady build-up would lead to an explosive orgasm for him. Yes, at that point, as far as I was concerned, it was all about him and I was there simply for his pleasure. That would soon change but right now, I was loving every second of it!

I stood up and kissed him on the lips. He tasted and licked every essence of the taste of his own cock from my mouth. I took his hand and placed it between my legs. He rubbed his hand up my inner leg until he found my little cock and hidden testes.

Although my cocklette had gotten hard at various points in the evening I had ignored it for my duty, as I saw it, was to pleasure my man. What I had failed to recognise was that Ben was here to see me not because I was a single girl but because I was a single girl with a cock!

He moved his hand up my crotch in an assertive manner, his fingers squeezing my leg dominantly and his thumb touching my now sunken sack. His manly hands pressed against my ass and taking control over the sensitive area between my cheeks.

There was no doubt that he now owned that property and that I had to give it to him. My little cock instantly swelled as big as it would go, pressing all of its 5 inches out against the gusset of my black tights. I felt embarrassed because this is not a normal reaction for a normal girl.

He loved it. He pressed the tip of his enormously erect cock against my nylon tights and the bulge that had emerged beneath. I looked at his face and his eyes were rolling in his head. I pulled him by his thick neck and urged him to my waiting crotch.

He dropped to his knees and began licking my cocklette though my tights and gasped for air in between licks and sucks. It tickled so much that I shivered with unbridled pleasure.

I rolled the waist of my tights down revealing my smooth erect cock and balls. He put his lips to my cock and slowly moved his mouth down my 5" shaft sucking harder as I saw the only identifiably male aspect about me disappear into his body.

He lovingly sucked, licked and splurted his way through the best blow job I had ever experienced. His hands ran up and down my legs, which made me tingle, while I placed my hands on my hips and shuddered from the ecstasy I was experiencing.

I glanced over at the full length mirror of my bedroom and caught a glimpse of us; a high-heeled, hot blonde receiving oral sex from a strong man giving his all. The moment was there. I looked and felt so sexy and all my senses were on overdrive from head to toe.

My legs felt sore from wearing the heels. Good sore. The short dress and silky nylons which encapsulated my legs made me feel vulnerable. The weight of my blonde hair as it rested on my shoulders. My so-called manhood disappear into his body.

I looked into the mirror and into my own eyes. They were unrecognisable from those of the male persona I believed myself to be most of the time. I felt the blood drain from my head and I felt faint and shaky and at that point. I groaned in pleasure as he sucked harder and bobbed his head faster.

All the love of my body suddenly burst out of my swallowed feminine penis and I squealed with pleasure as I came in Ben's mouth. I fell back against the wall behind me in ecstatic exhaustion as he sucked and licked up every drop of my juice.

He then looked up at me smiling. I looked down at him and with my forefinger led him by the chin up to my mouth and kissed him on the lips with complete submission. His mouth was closed and his lips pursed with a cheeky smile like a naughty boy playing with his food at the dinner table.

I placed my finger over his lips and gave him a stern look willing him to swallow my load. I watched his throat move up as my cum went down deeper into his body. We both smiled at each other then kissed deeply and as he held me tightly in his arms. I completely melted in subservience.

At this point I went to the bathroom to fix my make-up and change. I took off my dress and my bra and reached for the hook behind the door where my black silk baby-doll nighty hung.

I put my hands over my head and it slipped it down my arms, the thin black straps coming to rest on my shoulders and the silk fabric falling and clinging to my body. The pretty black lace detail across the chest accentuated the appearance of a feminine breast which I helped along with a little shading with blusher. I loved this silk nighty.

The silky material shimmered in the light, flowing and feminine, it was also stretchy and clingy so it hugged my figure and felt amazing to touch. The hemline rode high above the knee with just enough to cover my bum so very little was left to the imagination.

I looked at myself in the bathroom mirror and looked as good as I felt, dressed in smooth silky black. These tights felt comfy but I knew that the gusset was going to get in the way so I slipped them off and took a pair of 'barely there' sheer thigh-high hold-up stockings from their pack.

I have always loved stockings and this pair was exceptional. I lifted my leg to the side of the bath and slipped the stocking slowly over my toes. As I carefully moved my heel into the stocking the silky nylon unravelled, clinging to my leg, firstly around my calf, over my knee and ending at my upper thigh with the gel-backed lace-tops sucking onto my smooth skin with a sexy satisfying snapping sound.

The lace-tops were high on my inner thigh feeling very secure yet snug, with just enough of a hint of lace peeping down below the hem of my nighty to get any man's blood flowing! I slipped on a pair of matching black silky knickers for the feeling of extra sensuality and to keep my petite boyish bits in place.

I touched up my smudged lipstick and powdered my face a little then fixed my blonde hair and blew a kiss and a smile in the mirror...prettily and happily I minced back to the bedroom.

Ben was lying back on the edge of the bed waiting in anticipation. His large flaccid cock fell rested on his left thigh. Immediately as he saw me his eyes opened up and he said:

"Woah, you're getting ready for bed I see."

"Yes, well it is getting late", I jokingly hinted, looking down at him knowing that there was no way that he was going anywhere if he could help it.

He sat up and pulled me closer to him, his hands gripping me by the cheeks of my bum as I stood demurely between his spread open knees. 

  • 9 months later...
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