Blacked Out

I have found that success as a cross dresser is as much confidence as it is appearance. At twenty-five, I have been out in public as a cross-dressing club gurl for several years. Having skillfully developed good looks, fashion sense and a petite body has inspired many wondrous experiences. I am five-foot five and still weigh a slim one hundred and twenty-eight pounds. With shoulder-length natural blonde hair, in high heels and in a tight-fitting mini dress, friends tell me I can turn heads.

My first adventure to a Boston transgender friendly club was at the age of seventeen. The strong feminine feelings that I had inside me drove this behavior. My first experiences were scary, but my desire to dress as a girl was far greater. Eventually I met many people in the club. Some were quite nice and friendly, and some were quite the opposite. I settled in, going out every Friday and Saturday night during my first year of college.

I met an older man who became a trusted friend and protector. For months, he would meet me at the club and buy me drinks all night. Eventually, after a surprise kiss and further exploration, this man changed my perspectives completely. I learned when I dressed as a woman, I had romantic feelings towards men.

At first this was shocking to me. In time he became my boyfriend. Later I would meet a man who I would spend Fridays and Saturdays with. He would become someone I would call Daddy! I reveled in being a man’s submissive gurl. I was his dedicated pleasure gurl for forty-eight hours every weekend!

I would meet a few more likable and even enchanting men over the next five years. I loved the sensual side of myself increasingly. Being in the arms of an older, caring man was my happy place a crossdresser. I was taught all about kinky things. I loved pleasing as a woman. I so enjoyed being a man’s gurl and even his submissive. I had many options if I was honest with myself.

My kinkiness became extreme. I had a Daddy who put me in urethral chastity for hours at a time while we had incredulous sex. Not being able to orgasm in such a device only drove up the joyful madness in my pleasure giving. I would allow myself to be shackled, even tied, and pleasure my man orally or anally in full trust of him. Fortunately, I chose men well!

I had explored my sensual side as much as any cross dresser I knew at my age. A familial trust fund enabled me to purchase a two-bedroom condominium in an upcoming Boston neighborhood. I had privacy, independence, and a good paying Monday through Friday job. Life for me was great and I was always appreciative of my good fortune. I knew how hard some of the transgender girls in the club had to work. Some even worked as prostitutes!

On of one of my regular Friday Night visits to the club, I met a remarkably interesting man. He was handsome, articulate, and a former football player. He had a nickname in the club. People called him Batman. I knew from discussions with my girl friends that his nickname had nothing to do with the fantasy character. I was told that B-man also liked to be called Sweetness, which was a name he liked from college days as an athlete.

Sweetness had a couple of years as a professional football player. He was currently working for an investment company, and he had no trouble generously buying many a gurl in the club drinks. I had met him a couple of times and my friends told me that he was quite enamored with me. I am surprisingly cautious at times. The fact that I had never been with a Black man was interfering with my attraction to him.

Every woman in the bar was infatuated with him. He had a smile that lit up the room and was still in professional player shape. He was outgoing and he asked me if I wanted to play some pool. The club has a single table, and he had already bought me a drink. I could not say no, even though I was not much of a player. I was in a teeny, tight-fitting white, spandex mini dress that showed off my shapely bottom. It would be a bit of a show at the pool table!

He was thrilled that I would join him. I smiled back and winked at him. I was going into my teasing mode more consciously than I would want to admit. He was so funny as we played, and he had me in stitches as he called my shots for me! A little error on my part led to a funny moment. As I leaned over the table unintentionally exposing a bit of panty, he clearly called me out – telling me, “You are so hot, Cari!”

I smiled, knowing that we could leave the place in a hot minute if I had the courage!

He let me win as we finished the game. We went to the bar, and he bought me another drink. He looked me in the eyes, and I was starting to melt. He was warm, friendly, and funny. My inner trust meter was pulsing as much as my own pulsing, expanding tucked masculinity. I liked him and my fears were ebbing. Suddenly the lights went on. It was closing time. I wanted to go with him, but I was still afraid.

I did not want to lose him completely so I asked if we could meet back here tomorrow night. He seemed happy that I was still interested. “I think that would be great,” he said warmly. His response made my night, but I still possessed many fears. Was I not being honest with myself? I had lots of Black friends, but I had never been with a Black man. I had questions of myself to think about!

I went home and stirred in bed. Just thinking about this studly, handsome Black man made me so hot. In my sheer red camisole, I felt lusty and naughty. I could not keep my hands from running over my smooth, hairless skin and touching myself. I realized that my greatest fear was not that he was Black, but what was something beyond that. My fear was from what the girls in the club said about his nickname.

“Batman” or Sweetness, allegedly had a cock the size of a bat! I knew that even as skilled as I had become over the years, a man with a cock that big was out of my league! I had watched porn of well-endowed Black men with transgender girls. I was stunned seeing how some gals could try to take these men on. Even the porn gurls did not do so easily. Amazingly, though, some could.

The next morning, I made my decision about returning to meet Sweetness. I knew that I wanted to, but I had to overcome my fears. I was going to do it. I had always lusted about Black men but never dared. This was my chance. I sensed that he was a decent enough person. If I was unable to be his lover, I hoped he would understand. In trans circles like the club, a date with a man is sex. We both knew it.

I cleaned my condominium. My plan would be to bring him back here. I took a luxurious long bath and shaved myself silkily smoothly. My make up was flawless and I blew dried my flowing blonde hair. I looked in the mirror and felt pleased with my appearance. I had a plan about the rest. We were to meet at nine. I would be on time. It was a cool evening so my thought process and plan might work.

Feeling nervous, I drove to the club, parking in a pay garage nearby. I took the elevator down and walked a half block to the club. I was wearing the five-inch white sandaled heels I wore the night before and my full-length faux fur mink. I walked in the club and the bartender offered to take my coat. I demurred, leaving it on hoping I would see my date.

Fortunately, Sweetness was both thoughtful and prompt. He was sitting at the bar waiting for me.

“You look stunning,” he said smiling.

“Thanks” I said, now feeling buoyant. I moved closer toward him.

“Do you want a drink? he asked.

“No, thanks,” I said with a smile. He seemed surprised. I coyly opened my mink coat, just for him to see inside. His eyes went very wide!

I was grinning. The only thing I wore was a teensy pink G-string panty. Between my legs, it hid the only non-feminine thing on my body! I was naked underneath! I had obviously made my decision, and Sweetness was going to be mine! We were off in seconds, back to my car and off to my condominium. We kissed passionately in the elevator. I was so moved that I felt everything may be all right.

Inside the door we embraced. He slid my mink coat to the floor. I stood before him in obvious vulnerability. I wanted to help him with his clothes, but I hugged him. I had to talk about the obvious elephant in the room.

“Can you be patient with me?” I asked weakly.

“Of course," he said, trying to assure me.

I spilled my fears about his reputed size.

“It is all up to you," he said warmly. He gave me a gentle hug.

I have always never hesitated at this point with a man. I wanted to go to my knees, but I decided to help him with his shirt and then slacks. He kicked off his shoes and he stood in front of me in blue jockeys. I was so horny and so scared. I decided it was time. I looked him in the eye and smiled out of experiences from my past. I was a nervous wreck yet as curious as any cat ever was.

You can’t hide what was obviously covered by his underwear. It was bulging and clearly huge. It was straining to escape his jockeys. I was almost afraid to expose it, yet as I pulled those shorts down his stunning, incomprehensibly huge horse cock was staring me in the face. I took it in my hand and looked up at him. I had every reason to be filled with doubt, yet I was drawn to it like a moth and flame.

I couldn’t even get the fingers of my hand all the way around it. I don’t know if I was more gobsmacked by his thickness or his length. Instinctually I kissed it and licked the tip. He was circumcised and the head of his cock was confoundingly huge! I didn’t think I would be able to get any of it into my mouth, but I was crazed in sudden urges of lust and need. Sweetness was not an ordinary man.

Placing both hands around it, I explored it with my lips and tongue. I should have been completely intimidated but I felt crazed, erotic urges and the need to explore more. I spread my lips wide and only managed to get but the first inch of his cockhead inside my mouth. He was delicious as my need and shamelessness inspired my actions, yet I felt the reality of unease in my stomach.

Spreading my mouth as wide as I could, I was able to somehow get his huge cockhead into my mouth. I began to gently move back and forth on it while trying desperately to take another inch or two into my mouth and the back of my throat. I realized how overfocussed I was when I realized that Sweetness was groaning. I looked up, unable to smile or even moan. His reaction encouraged me as my need to try to envelop more of his monstrous cock surged.

Somehow, I was managing to take a few inches more until his now very hard missile was at the back of my throat. I knew that I was doing well, but also knew that physically, this was the very best that I could do. I was so turned on by my success. My own seven-inch male hood was throbbing inside my pink G-string gaff.

My new lover seemed pleased. “Oh yeah, baby!” he moaned repeatedly. I was beyond thrilled and I never felt sexier and more turned on by giving a man a blow job.

I have had several gifted lovers and was able to learn to deep throat all of them. As much as I would love to do the same for Sweetness, I knew it was physically impossible, though desire had always worked in the past. I was as happy with myself as he was with me. I always wanted a man inside of me when I liked a man. I liked Sweetness a lot and I always saw oral sex as a lead up to more. I was crazed in my lust and as willing as ever to be a woman for this man. To me that meant more!

I stood up and our lips met. Sweetness apparently knew exactly what I wanted. He lifted me right off the floor and carried me like a child. I was crazed by being manhandled by this six-foot-four football player who picked up his one hundred and twenty-pound gurl like she was a child.

He found my bedroom and gently placed me on the bed. Kindly, he looked me in the eye. “Are you ready to give it a try Cari?” he asked coolly.

“Yes, please,” I replied weakly, but with a wink. I was nervous but I knew I was going to try to be one of those porn gurls who could. I wanted the biggest cock in town, and I was crazed and filled with dread at the same time.

“Some gurls like to get on top,” Sweetness suggested. That sounded perfect to me!

I had lubricant on the nightstand next to the bed. I went to work covering his foot-long cock as he lay on his back smiling at me.

“You seem excited,” he said with a grin.

“I am but I’m nervous,” I replied honestly. “I so want to have you inside me, Sweetness!” I said, being the perfect slut. My emotions were all over the place, but I can be a very determined gurl.

“Let me help you?” Sweetness suggested. He pulled my gaff off me, exposing my very hard pre-cum dripping boner. He rolled me onto my stomach and squirted the liquid onto my bottom. He worked a finger inside me and then two, as I moaned like a needy whore! Now it was time. Would it be regret or success? I had always fantasized about such an opportunity. Now it was very real.

What was most wonderful about my new lover was his understanding and patience. I straddled him on my bed. Sweetness first pulled me down to his face for a long, delicious French kiss. I was so moved and was so ready to try to take his incredible manhood into my willing little bum. Straddled atop him, I took that huge member in my hand and rubbed it against my opening. I was tense. Would it be humanly possible?

I pressed against it squirming and trying to relax my sphincter. Just as I thought I was making progress it slipped away. I tried again, then again. The third time, I felt his huge bulging cock head get beyond my sphincter. I felt like I was suddenly impaled by a telephone pole!

I didn’t dare move. I tried to relax. I took deep breaths. I remembered the first time I took a dildo into my anus. Relax, I kept telling myself, relax! Sweetness, who had been motionless, suddenly thrust upward. My eyes widened as I realized he was now deeper inside me. It hurt but when he asked if I was okay, I fibbed and said yes. I knew from when I lost my virginity that in time there was always hope that it would feel better. Right now, however, it was not the case.

I rocked upward gently then downward. Sweetness was gentle. He was up thrusting slowly, and I was instinctually responding. His cock literally felt like it was going through my entire body, yet it was probably in reality but a few inches inside me. I was determined perhaps mostly due to my lust. I was sitting atop the biggest cock in the city of Boston, and I was beginning to find joy in it!

I suppose success breeds success, no pun intended. In gently rocking atop him he was getting deeper inside me. When my bottom met his thighs, I rejoiced! He was all the way inside me. I reacted by speeding my thrusts, and a very willing Sweetness was thrusting upward, almost making me fly into the air yet pulling me back down upon him. We were making love, and my insides hurt and burned, yet the feeling was amazing.

Sweetness pulled me towards him as we kissed again with his incredible member all the way inside me. Tears of joy ran down my cheeks. Suddenly I was being lifted. He guided me with his muscular arms and shoulders and in seconds was on top of me.

“Daddy wants to breed his gurl!” he said, smiling. I was tense. “You are beautiful and so special, Cari,” he said smoothly. His words suddenly changed my mind about the missionary position!

The next hour then became a blur. He fucked me meaningfully at first. He kissed me repeatedly and I swooned and swooned. Then he fucked me with the kind of fury that I never had experienced. He was hurting me and yet I kept grabbing my own cock, milking it to soothe myself from the discomfort. Eventually the pain ebbed. His fury was incredible but the shrieks now coming from my mouth were shrill and impassioned.

The sounds in my bedroom were now frenzied. This bull of a man was also groaning deeply. I was suddenly aware that after what seemed an eternity, he was getting close to orgasm. I dug my nails into his buttocks and held on. I was so moved and so thrilled by the frenzy and deep meaning of it all.

“Daddy’s coming!” he yelled.

“Yes, Daddy!” I shrilled back.

He shuddered and I felt the heat of the sea of his semen filling my deepest insides. I lost it right then and there. I came as though on a switch. My cock exploded between us and my sphincter spasmed around his massive cock, causing him to growl like a lion. I saw stars. I saw nothing. I blacked out. I was stunned and moved like never before.

Together we lay panting, with him still atop and inside me, both of us stunned by what had just occurred. He asked me if I was all right.

I grinned. “Oh yes!” I said with a wink.

I have had orgasms that were crazy good but never one like that! We shared our amazement and knew that we would be more than a one-night stand. He stayed the night and wow, I had an unforgettable night and a new and very incredible Daddy! This guy was truly special, and I had all the footage of our bedroom antics on my security system for posterity! If I have learned anything in life it is to be courageous. I most certainly have no regrets.