Being a pretty, petite, believably passable crossdresser makes me a very happy person. I have been dressing up as a sexy girl while daring to go out in public for the past two years since I was sixteen. I have had this urge and desire to dress as a female for as long as I can remember so I have gradually come to accept that I have a feminine side that needs to be nurtured and encouraged.

I have managed to accrue several wigs, dozens of dresses, many pairs of high heels and enough makeup to last me for years! My skill with make-up and my ability to enhance my feminine appearance with all of the details is very advanced for my young age.

I live alone in a one bedroom private apartment near my college in a great northeastern city and I am a fairly normal guy during the week. I so look forward to the relaxation and excitement of transforming myself into the very alluring, believable young lady that I become on the weekend.

I am blessed to be short, slim, and have long slightly sun bleached blonde hair. I look a tiny bit feminine as a guy due to the long length of my hair and my slimness, but no one has ever read me as my male persona when dressed up as Cari.  

In two years as a nightclub “girl”, I have experienced many rather unusual perspectives, to say the least. Being out in public as a boy who has turned himself into a girl can be dangerous yet oddly rewarding. I do however find it to be exciting, as I so enjoy and even lust when I add make-up, sexy woman’s clothing and perfume to my fully smooth shaven, lithe body. The thrilling, sensual result is a convincingly hot and quite sexy gal who has men making regular unwanted advances towards me.

My alter ego “Cari” loves making her stunning appearance in high heels and only some of the sexiest mini-skirts and sensually alluring dresses. I adore being a tempting and attractive girl out on the town on Friday and Saturday nights! It is so much more exciting than being my male self when out on the town.

Clad in silk underthings, short dresses and perfumed smooth shaven skin makes for a very realistic, convincingly authentic girl in my brain. This credible self-belief makes me appear that much more authentic as a female because I believe in my heart that I am a genuine female when all dressed. People that meet me so often reinforce that ego-driven belief especially when they assume I’m all girl.

Practice makes perfect and I am always obsessive about all of the details that it takes to go from a boy to an attractive girl. When a person sees me in all-out feminine drag as the girls say, it is hard to read that I am anything less than female. Being almost model like slim, narrow wasted and well-practiced in everything from my high heeled walking to my deftly feline mannerisms.

I am skilled in speaking and have practiced the mannerisms of a female when I am dressed. Dozens and dozens of people have been amazed when I tell them I am really a guy. So many assume I have had surgery and have had a sex change when in reality I would have nothing of the sort!

In my first year out as “Cari” in public, I learned too quickly about the risks, dangers, and expectations of being a pretty young boy girl in a transgender nightclub! I was often solicited, asked out on dates, and a lot worse. I slowly adjusted to the dangerous Star Wars Bar atmosphere of the clubs. I was convinced that I dressed simply for the love and joy of feeling the wonder of wearing silk stockings, feminine dresses, and sensual lace under things.

In time, I found my fetish might have far greater implications. In spite of my advanced and overtly feminine appearance, I never acted on any of the regular proposals and requests that I so often received from men. I was convinced I was purely heterosexual and a normal guy who loved having a feminine side.

In the transgender world and club arena, it is so hard to maintain all personal discipline. Drinking has a lot to do with comfort and perhaps letting down the emotional and spiritual walls that I have. It was a foggy memory, in the beginning, to say the least. It was an evening where a nice older and man who I’d met a few times before had bought me countless drinks.

I acted in a manner that I never had, allowing myself to be kissed by him and even finding myself responding sensually and emotionally to his touch and advances. He had asked me on a date twice in past weeks and I knew how much he liked me. For some reason the combination of my inebriated state and my genuine like for him found me being more vulnerable than I had ever been.

I had spent a full year in this fast and furious bar scene never acting on any man’s advances. Tonight though, the alcohol had numbed my denials and may have brought out my need for something different at least. Because of the liquor, I was unsteady at closing time in my sexy high five inch heels.

The handsome older man was very much the gentleman in offering to drive me back home. He told me he would take a taxi so that I could get my car back to my not overly distant apartment. 'What a great guy,' I thought. I thanked him for his friendship and he drove me back to my apartment in my own car. His gentle caresses on my stockings on the ride home and his goodbye kiss had me reeling in an odd sort of way.

When I got out of the car I was still woozy and unsteady. I was not in full control and realizing my struggles, he kindly walked me up the stairs to my third-floor apartment. I was so lucky that he was a true gentleman and he even helped tuck me into bed but not before I insisted on wearing my sexy purple sheer baby doll nighty to bed. I must have been out of my mind – even giving him a quick sexy pose modeling it before I practically fell off under the covers and into my bed.

Half passed out, I slept deeply dreaming about feeling the delight of feeling both feminine and pretty. It’s a common dream for me but something seemed different, especially after being so smoothly shaven and so elegantly perfumed. My dream was both emotionally and physically erotic. I found the dream to be as pleasing and exciting as any that I had ever had.

I dreamed that I was being hugged and coddled. I awoke in the middle of the night a little startled at first. My seven-inch male hood was hard and straining while tucked between my legs where I liked to keep it hidden when dressed as a complete and sexy girl.

I felt a pleasing but unusual warmth that seemed to go beyond the feel of my sheer purple baby doll nighty. I was in quite a state of confusion because I suddenly realized that I was not alone! I was being spooned and held closely by a man who I knew from his cuddling embrace was also quite naked. His arms were around me as I had been sleeping on my side! One arm was under my shoulder and the other around my smallish waist. Was this a nightmare or what?

I had apparently told him before I had practically passed out that it was OK for him to, “sleep with me!”

I couldn’t help but feel the reality of his hard manhood rubbing against my panty less derriere. I didn’t know whether to scream, panic or try to escape his hold. My insides felt a strange and unique comfort and my senses were dizzied by his touch and warmth. I actually felt that the feeling of having his cock rubbing against my bottom to be deliciously naughty, incredulously arousing and wonderfully good! What was happening to me? This was insanity.

His simple naked presence was provoking every feline instinct in me. I tried to convince myself that I was simply a woman together in my bed with a man. My mind was spinning yet my body was responding to him as it had never responded before. Perhaps I was simply really a girl because next to him I most certainly felt like one!

 I was a little foggy but I was unconsciously responding to his advances. I was instinctively arching my backside against his huge hardness in a rhythmic rubbing that seemed more natural and erotic than odd. I was acting like a sleazy girl in need. As my awareness increased, I thought back to the evening. I realized that in spite of my drunken state at bedtime, I had foolishly and naively welcomed this man into my bed to sleep. Now I was feeling a rush of desire and need that I had never felt with a man before tonight. 'Was this just a dream?'

It seemed like it just had to be something like that. I never gave in to the men at the clubs. Was my half hungover and perhaps still inebriated condition affecting me in such a way? Why was my cock so incredibly hard and stimulated? Why did I feel so sensual and aroused? Why was I rubbing my bottom against what felt like some kind of huge freakish cock?

It was snuggled so intimately and close to my smooth, round derriere that it couldn’t be real! I was feeling so confused, yet so aroused that I apparently wanted something more. I began to wonder what it would feel like to have that hard phallic member inside even though it went against every belief and conviction that I had believed about myself.

There are crossroads in everyone’s life and I wondered if this was one of mine. I was enthralled by his touch and the manly strength with which I was being held. I felt so soft, feminine and vulnerable in his arms. I began to feel that I wanted to submit to him in the same way that a woman would do. I had in the past played with anal toys because of the pleasure they brought me, but I never equated the dildos and vibrators to any need or want for a man. It didn’t seem to matter in any way now.

Having his cock inside me was suddenly becoming my simple yet lustful desire. I was ready to be a man’s woman. In either a twisted or even normal way, I was more than ready to take a man’s cock into my willing behind.

I reached behind and took his huge cock in my fingers. I was aghast feeling the huge mushroom shaped head and the thick girth of his shaft. This man was long, thick and huge and I was quite unprepared as I rubbed it gently doubting whether I had the capacity or even the courage to try to take it inside my body. He stirred and he suddenly became fully aware and awake. He turned me and kissed me face to face, while suddenly pressing his nude body against mine.

Now, I felt so incredibly feminine and helpless. I was being held forcefully against his nude, hard, hairy body. One strong hand held my bottom and the other the back of my neck. His mouth met mine and his greedy tongue searched my mouth. I was melting faster than fresh snow on a summer’s day.

I don’t quite know why but I knew that I wanted him. For the first time, I was ready to submit to the wants and desires of a man. Years of denial were rapidly coming to an end. He rolled onto his back, taking me with him as I was now atop him. His kiss was wondrous, smothering, overwhelming me and filled with such desire.

With both of his huge hands on my soft, bare ass cheeks I was breathless and in need. I asked him to get a condom. I did want his cock! I had crossed over the line that I never believed I wanted to jump over.  I never thought I was willing to dare!

Fortunately, he carried a condom and found one in his pants pocket. As I modestly lay under the covers I saw his nice manly body and the massive and even freakish size of his hard, intimidatingly over-sized cock. My eyes widened and I wondered if I’d lost my mind until he quickly returned and tore off the covers off me.

He smiled as he exposed my smooth nude feminine body covered in but a bit of sheer silk. He pulled me towards him telling me how hot I looked. He spread my legs and bent them backward. I felt like a gymnast with my ankles by my ears. When his mouth and tongue went right to the opening of my anus he began to rock my entire world!

The experience of having a man go down on my anus orally caused me to be so moved and aghast that I almost orgasmed in seconds. The feeling of being licked there caused sensations so intimate and powerful that I was going crazy. Each greedy lick John gave me made me go into weird quivers that drove me into irrationally wild tremors. It felt like my mind was going to blow up along with my cock from the intensity of the pleasure I was feeling.

I was panting and shrieking from each lick and probe of his tongue. The intimacy of this act was bringing me outlandish pleasure that I never dared even imagine. He began probing deeply into my insides with his tongue and I began shrieking in disbelief.

“Oh God, yes!” I squealed over and over.

There was no stopping him now and he greedily pleasured me. Soon I wanted his cock so badly that I almost asked him to forget his fortunate pause to roll the condom over his massive male member!

Suddenly after seeing his cock inches from me, I called out his name.

“Oh, John!” I squealed. “Please be gentle!” I pleaded.

I was in a panic of doubt due to his enormous length and girth.

“I will,” he simply and confidently assured me.

Fortunately he was patient. He pulled me above him allowing me to try to sit atop him in the hope to give me some control.  He helped center my anus over his massive, throbbing, mushroom-shaped cockhead as I shuddered in fear. Now I was seriously wondering about my behavior.

I was hoping for the impossible to happen and I had this needy, driven craving. I was willing to deal with the pain. I knew it would hurt yet his oral attentions had me so lathered and stimulated that my cock was as hard as a rock and I was more than ready to cooperate completely. The first attempts seemed futile.

After several slips, my opening and sphincter couldn’t possibly seem to stretch that far. John was determined though. John took control and gradually the combination of having John guide my waist, coupled with his gentle up thrusts into my well-lubricated insides caused some progress.

With a sudden pop, I felt the incredibly painful, knife-like experience of having that huge cockhead partially enter me. I whimpered, half crying in the intense pain. Soon John maneuvered his cockhead fully inside me yet the discomfort only increased the pitch of my shrill whining. I felt like I was filled with a fire hydrant. This was only the beginning and I was feeling desperate.

John’s pleas to have me relax first fell on deaf ears. Soon in my desperation, he convinced me to listen. He had me take deep, breaths and stay perfectly still until the pain and discomfort eased some. After a good minute of breathing I finally, for a moment, felt like I was back in control of my insides and emotions.

In gratitude to John, I made the next move, thankful for his patience. I rocked myself down further onto his massive missile as I gasped in a combination of pain, strange pleasure and disbelief. John leaned me forward and we kissed passionately.  He was only a bit inside me but his kiss just brought my need and desire up to the next level.

Soon I was being guided up and down on his pole as his gentle up-thrusts found me being more and more filled. I was wailing in disbelief. My guttural groans were loud and desperate sounding. The pain was immense but my need and the burgeoning pleasure helped drive me downward to feel the wonder of feeling his balls pounding my ass beneath me.

With him fully inside my anus, I finally relaxed more and felt free. I had accomplished what I thought was impossible and John was as grateful as was I. Feeling naughty and now more capable, I began to ride him and watch his face. I was pleasing my man and he was groaning as much as I.

I was so excited that my spring-like bouncing erection was dripping and wet from my own pre-cum. I couldn’t imagine any act more powerful or stimulating than this. I was a pleasure girl riding her man lusting in feeling his balls spank against my ass as our thrusts became synchronic in their perfection. I was no longer in doubt as John rubbed, squeezed, and pinched my breasts as I rode him. His actions just drove my desire further.

I was proudly riding his cock in a heated frenzy and this was my first time. Nothing suddenly could seem more natural to a feminine “lass” like me! Abruptly in but a single movement I was being rolled onto my back. Without any pause, John lifted and spread my legs.

With his cock still deep inside me I was now completely and helplessly his. Being fucked in the ass this way is truly a helpless surrender. His deep thrusts were filled with pain and yet growing incredulous pleasure. My insides and brain were now on complete overload.

John suddenly stopped his intense thrusting and paused. He looked me in the eyes and smiled. “Are you Okay?” He asked with kindness.

“Yes,” I blurted. “Yes!”

John began his hard, forceful thrusting again only now with a fury and rush that seemed beyond comprehension. Now his rapid-fire assault caused loud spanking sounds to echo from the walls of my bedroom. John’s groans were now getting louder and more frantic sounding. I knew he was near but all I could do was hold onto his back and powerfully driving ass as I lay helplessly beneath him as his feline submissive lover.

All of my circumstances seemed inexplicable and so sudden. Even crazier was that I was becoming so moved and so aroused by his powerful thrusting that I knew I couldn’t prevent what was building inside me. Being fucked so mercilessly and so capably had me seeing stars. I began to tremble and shiver. I was feeling little explosions deep inside me. Soon the intensity expanded as my orgasm began to erupt.

It started deep in my anus, then it seemed my entire body was electrified and moved beyond comprehension. My cock began to spew stream after stream of my cum and my well stretched sphincter and body began to spasm in a quaking that made my entire body shudder in a pleasure. It was so maddening that my screams were interpreted by my lover as pain.

Fortunately, John almost immediately realized that I was coming. He felt the intense, noose-like squeezing and milking of his cock from my insides and sphincter. It was easily enough to cause him to also go over the edge into a massive orgasm along with his pretty little girl. The physical pleasure was powerful beyond words, but more than anything my soul would forever be changed. Our night would be full of lust until dawn.

The night included my first oral encounters with a man’s cock. I was shocked at how much I enjoyed the taste and the joy of making a man moan and get hard as can be. It made me hard to be a girl for him pleasing him with my mouth and throat. I realized that being a girl seemed a lot more natural to me in the arms of a man. The dimensions of lovemaking and who I had become had expanded exponentially and it turned out that I was as naughty and voracious a lover. I loved every minute of being a girl for him!

In the morning I drove John back to his car. Our goodbye kiss was almost as memorable as the night. He wanted to see me again and to take me to dinner. I told him I would think about it. Driving back home I realized that I had found something that I never really sought.

The girl-with-extra was happier than she had ever been and it took a special person to guide my direction. I’d also learned that I enjoyed some special things in life that had been handed to me by one very skillful and capable older man who simply knew just what a girl wanted!