A Naughty Night

Cari Christi

I am fortunate enough to be called one of the real hot “gals” at one of Boston’s transgender night clubs. I’ve been “out” dressing up convincingly as a boy converted to sexy girl for two years and people assume I am a lot older than just nineteen. I feel and look quite alluringly sexy and almost always dress in mini dresses, high sexy heels and in long blonde tresses that bring out the Barbie look that so attracts men. Call me a drag queen, slut, tranny or whatever you choose, but I started out as a “straight” crossdresser who never thought that “she” had any interest at all in men.

I learned a lot in those past two years and it was not always intentionally. I keep myself ridiculously slim and my trim body is fully shaven to smooth perfection. My cute nose and fine facial features help my overall look in my very well-practiced make up. Being only five foot five and slender enables me to look believably feminine even in six inch high heels. I am blessed and so fortunate to live my dream as a weekend “woman” who so loves to be femininely sensual and attractive while meeting folks at the club.

It all changed when I naively allowed myself to be convinced to go on a date with a man a year and a half ago. I really didn’t think I was attracted to men in any sexual way. My date talked me into modeling some lingerie he bought me and of course one thing led to another. How dumb this blonde was to not realize that wearing sheer sexy, feminine lingerie for a man in his bedroom wasn’t the ultimate invitation? To my surprise I will confess that I ashamedly enjoyed it far more than I wanted to admit to myself.

I now understand that sometimes I dress just for that reason. I admit that I love men and to attract men is exciting to me when I am dressed. You might say I am a “straight woman!” I like to be a pleaser for a man that I find attractive and attractiveness to me is more about that person’s ability to connect with me rather than looks or appearance. I’d rather a plain looking, sensitive and thoughtful older man than some pushy young stud. Most importantly I believe a man needs to know just how to please a woman!

Recently I had gone almost 3 weekends without being able to be my fem side due to studying for college exams, so when I went out Friday night I was lit up with a combination of eagerness, arousal and what I might call lascivious need. I felt so feminine yet wanton and I just knew I how much I “needed” the loving attentions of a capable man. I had to be careful though in a place like this!

I am honestly not usually forward or improper, but every now and then what is perhaps my true erotic suggestive side emerges. If I want a man, I can dress, behave and find myself being sensual on both the inside and outside. Tonight would be that kind of night. There was always the danger yet it provoked a strange excitement.

Most people don’t know how dangerous that transgender world can be. I have no less than two friends who were murdered by a sicko who once prowled transgendered girls in the clubs and on the streets of my hometown of Boston. Many men also get what the Transvestite Call Girls call “buyer’s remorse” who panic when they realize they might be gay or something they suddenly regret. A “girl” must be careful, offer no surprises, and have an outstanding sense of reading people.

That made the danger of showed up in the club in a never more suggestive manner than I had ever dared in a public place to be both risky and risqué! My appearance was so outrageously sexy then when I met “Jack” he asked to take this picture of me on his cell phone. He showed me the picture and we laughed about what and how clear my manner of dress apparently “had to say” to anyone who looked at me clothed in the minimalist manner in which I had presented myself.

 “I walk into the bar and the first thing I see is this blonde bombshell in a see though dress showing a sexy black bra and backless thong panties. She is in six inch white high heeled sandals and has the poutiest red lipped smile I ever saw! I must admit I so want to take you home because that’s the message you are sending out – at least to me girl!”

His bluntness and frankness made me laugh and I appreciated his honesty when he bought me a drink. I also had to admit to myself that I was immediately finding myself quite attracted to him. I knew almost instantly that this man and I would be together as lovers as soon as we could make it happen. He knew that about me as well.

The drinks he bought me and our sensual conversation just made the anticipation that much better! It’s hard to imagine just how liberating it felt knowing that we were going to have sex together. I found it so exciting and so naughty that we were openly and honestly discussing our likes and dislikes as “lovers” here while toasting each other at the bar.

He asked if I liked sucking cock and I blushed. I smiled, looked him in the eye, winked, and said “I’d love to suck your cock handsome!” His smile and surprised reaction had us laughing and as comfortable as any two would be lovers could be. Anticipation is almost as blissful as the real thing and when he put his arm around me we kissed and we were soon on our way.

By the time we got to his house, he knew he was in for a treat and so did I! I had admitted my sexual likes and dislikes to him and he wasn’t fibbing about having a nine inch cock either! I didn’t have to get out a tape measure when I got down on my knees and unzipped his pants on the living room floor! He was all he had claimed only I felt he seemed a bit modest and humble about his huge, thick, oversized member. Perhaps this was another reason he was so quietly confident! His wondrous cock seemed stunningly overwhelming and never ending! I was drawn to it like a moth is to a flame!

I wasted little time tasting him while coyly looking up at his face. He was already quite pleased and I had him moaning in seconds. He tasted marvelous and I was as eager as any young “girl” could be in the hope of pleasing a man. In moments I had much of him in my mouth and throat and in spite of his huge size I was focused on the goal of deep throating every single inch of him. I knew that I could. I had been taught well by my first lover. He was as well-endowed as Jack!

Back “then” I was a lot less than enthused about sucking cock. Now though, it just made all the sense in the world to me. I love pleasing a man this way and I believed a good girl should do just that. Keeping a good man happy is a girl’s purpose. Jack moaned and told me what a “good girl” I was and I paused from my “duties” to briefly to smile and to seductively tell him just how right he was! Soon I put my throat to work with the relaxation techniques I had been taught. Soon I found my nose was meeting his pelvis and my chin was pressed right up against his balls. His huge nine inch cock was all the way in my mouth and throat! Jack was astounded, delighted and quivering with joy and I was proud to be a truly good girl!

When I suck a man’s cock I marvel at how hard I get as well. It is almost like I was sucking my own cock because I get so incredibly hard and stimulated that I drip and drool down there. It just reminds me that I have such pure delight and enjoyment in oral pleasure giving. I’ve been called a lot of things while doing this to a man and I truly enjoy hearing even some of the most decadent and scornful terms a man may use during my efforts. Being such a “Naughty Whore” is how a girl keeps a man from cheating on her and how she keeps him in her bed! If only more women understood that!

There is a selfishness and a level of self-control that limits my zeal to please a man fully orally. That pleasure to me involves more than just cock sucking. Having a real man fuck me is just what I so lust most for. It was almost a year and a half before I admitted that reality to both myself and then to my girlfriends from the bar. Now I would quietly go about a little more manipulative seduction so I could find that huge, delicious man cock inside my very needy, cute, shapely and very willing ass!

I stood up, a bit wobbly in my high heels and pressed myself against his tall, firm, hairy body and hugged him. He pulled off my dress and while I hastily helped him get naked. Soon the floor was covered in clothes as he took me by the hand and up the stair way to his bedroom. I was already smiling in my heart! In but heels, bra, and my famously naughty backless panties, I was ready to be fucked by this gloriously well endowed, hot and very sexy masculine man! I felt like such a “girl” in spite of having seven inches of manhood straining and pulsing in my panties!

His bed was inviting and we were soon atop the white throw locked in an intense kiss. He moved atop me and spread my legs. “Condom please Jack!” I blurted. Suddenly I realized Jack was a little less sensible than I thought. I had condoms in my purse if he didn’t have any. But I might have to start carrying extra-large perhaps in the future! Fortunately he got up and found one in his dresser. He didn’t need help with it but I loved what he decided to do next!

Jack placed me on my back and bent me backward. He almost tore off my panties as I helped keep them from tearing. With my high heels now helplessly pressed back by my ears he began licking my anus as my own cock strained in delight. I get so turned on by analingus that I can easily orgasm. I am wired a little different that most people in that I can orgasm anally from either oral stimulation or from deep and powerful penetration. It is stunning and beyond belief in power and delight for me.

Jack was so big that he allowed me to be on top to start our fuck session. I faced him, spread my legs and tried my best to mount and center myself over his huge, pulsing organ. Thanks to the thorough licking my ass had been given by Jack I found his entry possible. A man this size is not easy for me but I slowly sat further and further down on him as Jack patiently waited for me to find comfort.

Soon I was slowly riding him and he began gently thrusting upward. My cock was hard as a rock and now bouncing up and down on his pelvis. I was in heaven and we were only beginning a love dance that would be as intense as any in my young experience. Jack drew me forward as we kissed and as he guided my waist up and down on his endless thick shaft. “Oh Jack!” I mumbled. “You feel so good!”

That signaled Jack to ask me to get on my knees. On the bed I complied and he mounted me from behind and took hold of my waist and hips. Suddenly his strokes were fast and frenetic and my shrieks and high pitched squeals sounded pained and beyond belief. His huge cock was punishing my prostate deep inside me. I begged him to stop because it hurt so badly. Fortunately Jack understood and paused deep inside. Somehow he slowly twisted and manipulated my insides so that his cock went deeper and beyond my prostate. Soon the pain had ebbed.

Jack went back to fucking me as I began reveling in the glory of having a huge man ravish me in the way I so loved and desired. Now I was begging for more and jack did not disappoint. I turned and noticed that beside the bed the entire wall was mirrored. This pretty, blonde “girl” was being ravished in the ass by this huge stud and his huge cock would disappear and then reappear in but a fraction of a second. The scene was incredulous and it was hard to believe that the pretty girl had a cock that was bouncing as frenetically between her legs as his cock was pounding “her ass”.

I was getting crazed by the intensity of being so thoroughly used and pounded yet I was thrilled beyond belief. Soon his pounding drove me from my knees and onto my stomach. His fuck strokes continued as I struggled to breathe with my face buried in the pillows. Incredibly though this was heaven. Jack was the ultimate stud!

Jack slowed for a moment and turned me onto my back while skillfully remaining inside me. He kissed me while slowly pumping his hard pulsing cock deeper into my depths. Now with my legs bent back to my ears I was helpless. His lips greedily were meeting mine as I was holding on for the ride of a lifetime. His searching tongue swirled in the depths of my mouth as I swooned and began to tear up in the most helpless joy that I had even known.

This was crazy. This was just too much. I knew I was a goner and the explosion began deep in the place where his huge cock was pounding me. When I erupt in anal orgasm my whole body participates! I quiver all over and my insides spasm. My sphincter shudders and contracts wildly making my lover more than aware of what is happening. These tremors and contractions squeeze my lovers cock so uniquely that he knows I am beginning my orgasm.

Jack was so moved that he too began to moan deeply, then gutturally, as I knew he too was on the way to orgasmic relief. A “girl’s contracting sphincter can also move a man to the end point. It always seemed to happen with the men with whom it had been carnally. This though was incredulous as I saw stars and was dizzied beyond belief. I was so overwhelmed with pleasure that I cried out into his greedy mouth as Jack too shuddered in the madness of what was a very mutual and powerful shared orgasm.

I felt so helpless and so loved as I felt his entire body shudder and quake. The powerful need a man has when fucking a “gal” is incredulously intense as are the moments of climax. I don’t know which is more powerful for me – the orgasm or the spiritual pleasure of knowing that I have sexually pleased a man “as a woman”. The joy in my heart is every bit as immense and the joy his huge cock has brought to my electrified feminine self.

When it was over we kissed passionately. Motionless and exhausted he was still atop me and inside me. My arms were still wrapped around his back and ass and I just didn’t want to let go. Jack smiled. “You are amazing! You are a very good girl!” I smiled broadly savoring each of his words. “You are a very good man yourself Jack! I said sincerely. “You sure know how to please a girl!” We laughed and hugged. This was rapture rarely found in the world of trannies and their admirers.

I could have left to go home but he asked me to stay. The answer was easy! There was no way I’d let this stud out of his bed tonight. My heart had been filled as much as my insides had been! I have talked to other “gals” like me and when a man acknowledges the sensuality and femininity of a transvestite in the wondrous manner that Jack had, our happiness is both physical and spiritual. Jack had made me feel and “be” his girl and I could never feel more feminine and loved.

He was as skilled and as talented the second, third and fourth times we made love. The morning was unforgettable too! Jack is still on “my list” and we are a couple of convenience! We sometimes meet at his place on weekend nights for sensual times that have expanded into marvelous fantasies. I don’t have to dress in extremes to insure a great time on those nights! I just show up naked in my high heels and fur coat and we enjoy a “quiet” night together in his bedroom…. But I’ll always wear something special just for him! I am after all – a very good girl!



Cari C



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