Tryst of Truth

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A trip to the dark side of town.
2.5k words
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I never measured up as a man. Try as I might, I couldn't match the masculinity of those around me. Women saw me only as a nice boy, never as a man. Eventually, I began to question myself, to question my own masculinity.

I found myself, yet again, walking downtown looking at all the happy couples and feeling absolutely un- wanted. I realized I wasn't the masculine ideal, but I still felt I was fairly good looking. I dressed well, shaved and showered, and still couldn't find a girl to go out with me. Hence, my walking downtown living vicariously through others.

I eventually walked into a bar on the corner. It was quite dark inside and it took me a moment for my eyes to adjust. When they did, I saw several people basically staring at me. Not wanting to look awkward, I strode up to the bar and sat on the stool to order a drink. I began scanning the room and learned that I was the only white guy here. Not the only white person, but the only white guy. I felt intimidated immediately, even more so than usual. I returned my attention to my drink, which had arrived, and tried to avoid all eye contact.

Looking into the mirror behind the bar, I was able to continue viewing my surroundings without being obvious. I saw white women in the arms and laps of black men, and a few blacks couples, sitting in booths and around tables. I also caught the looks from a few large black men eyeing me as if I were a slab of ribs.

It was in one of those moments that a tall black woman sat next to me. I was startled by her touch on my thigh, as she asked me to buy her a drink. Shocked and scared, I said, "yes," before the word even registered on my mind. She smiled, called the big bartender over, and ordered herself a cocktail. Of course, I paid.

"What brings you out here tonight, Sugar?" she asked me.

I explained that I was just walking around and accidentally came in here. I also told her I would leave as soon as I finished my drink. I didn't want any trouble.

She chuckled, and said, "You don't have to leave, Sugar, we're all friendly here. My name is Tanya. What's yours?" As she wrapped her full burgundy colored lips around the straw in her cocktail, to sip her drink, I was held hypnotically in her eyes. "Bill," I replied.

We began to relax and stuck up a conversation. She continued to call me "Sugar" or "Sweetie" throughout the night, but I didn't mind. Once in a while she would use my name, calling me "Billy" even after I told her my name was, Bill.

Tanya's hand found its way to my upper thigh many times, occasionally stroking back and forth, causing my penis to stiffen in my jeans. She didn't seem to notice, so I avoided looking down at her hand so as to not draw attention to my situation.

As Tanya and I talked, I became oblivious to the rest of the bar patrons. We drank steadily and my world only consisted of her and I. Before I realized it, it was closing time. Sadly, I feared I would have to say my goodbye's and never see her again. But Tanya surprised me, giving me her number and requesting that I call her, "soon. Real soon."

I stood up to leave and found that I was quite drunk. Tanya and another man helped to the door. A powerful kiss by my Nubian goddess, sent me on my way. I didn't get very far before I had to sit down. Slumped against a building wall, I tried to assess my situation. That was when I saw Tanya leaving the bar in the arms of a rather large black man. I was defeated.

Two days passed before I had the nerve enough to call Tanya. She answered on the third ring, "Hello?"

"Hi, Tanya. It's me, Bill. We met the other night..."

"Billy! What took you so long, Sweetie?"

I told her what I saw that night and wasn't really sure she wanted to hear from me. She explained that the guy was just a friend, nothing to worry about.

"I've been waiting for your call, Sugar. I was hoping you would like to go out with me sometime."

"Sure I would," the words jumping out of my mouth.

"That's good to hear, Sweetie, because I was hoping to fuck you."

The statement caught me completely off guard. It was all I thought about since meeting her, but I never expected her to agree to it, never mind mention it.

"You still there, Sweetie?"

"Uh, yeah," was all I could manage to say.

"Good. How about Friday? Pick me up at 8."

"Where?" I asked, regaining a little bit of my senses. She then gave me her address.

Friday came after an excruciatingly slow four days. I put on some nice jeans and a button down dress shirt, making sure I looked my best. I drove to Tanya's address.

She was waiting for me on the street corner dressed to kill. She wore a red leather mini-skirt and a white blouse tied just under her breasts, which were on display in a satiny red brassiere. Her strappy red heels were at least five inches tall, which would make her tower over me. I stood at 6 foot three, she was nearly 6'6". All my excitement was lost, however, when I saw the burly black man from the previous night next to her.

As I pulled to a stop, Tanya and her friend got into my car. She explained he just needed a ride to the club, then leaned over and whispered in my ear, "Don't worry, you're still getting fucked tonight." This comment relaxed me, and we were on our way.

We returned to the bar we met in a few nights ago and ordered drinks. Tanya's friend went off to a bar stool alone while we found our way to a somewhat secluded booth. Tanya wasted no time kissing me and her tongue was fully in my mouth. She asked me to suck her tongue as she thrusted it in and out of my mouth.

Our passionate embrace was getting hot and heavy, really fast. Already i was fully erect and breathing heavily. Tanya took my hand and slid it between her legs to rub her wet pussy. I couldn't believe I was getting so lucky.

I wasn't sure how much time had passed, when Tanya's friend, Darryl came over. He pulled her close to whisper in her ear, so I made my way to the bathroom. I got several looks as I made my way across the bar. Once inside the lighted bathroom I understood why.

My lips were smeared with Tanya's burgundy lipstick. My mouth looked like a porn star after giving a blowjob. I tried to clean up as much of the ways smear as I could, but still my lips seemed somewhat stained. I walked back to find Tanya sitting there alone, waiting for me.

"Everything okay?" I asked.

"Everything is fine, Sugar," she replied. "Darryl's friends didn't show up and he wanted to make sure he wasn't left behind."

I felt my stomach lurch upon hearing that. I took my seat next to her and immediately felt her hand on my thigh. "Really, Sweetie, everything is fine."

We began making out again like two lustful teens. Tanya had me in her grasp, and I didn't want to leave her embrace. We drank, danced and kissed a lot. Time flew by and I was getting drunk. Before I knew it, Tanya was leading me out of the club. I was too drunk to drive, so Tanya gave my keys to Darryl. I was too out of it to protest.

I found myself in a bedroom, flat on my back with Tanya on top of me. Slowly, my senses were returning and I realized we were about to have sex. My hands became more furtive as the anticipation grew.

"Slow down, Sugar, we have all night." She raised up on to her knees, straddling my abdomen. Her skirt was hiked up to her waist, as she untied the blouse from under her breasts. I just lay there watching her. "Oh, Sweetie, we're gonna have some fun." She locked lips with me again.

In the ensuing moments, Tanya was completely naked, her glistening body splayed out on the bed. She pushed my head down to her pussy, and commanded me to lick her. The short hairs of her bush tickled my nose as I began licking my first pussy. Tanya directed my tongue with hers on the back of my head and with her strong thighs. I knew I hit a good spot when her thighs tightened around my head.

"That's the spot, Bitch," she cried out. I wanted to reply to that, but my mouth was full and held in place. "Yeah, Bitch, eat my pussy!"

My mouth was filled with a salty wetness as Tanya finally released me. "That was so good, Sweetie. You're a great pussy licker."

"Why did you call me that?" I asked Tanya.

"Call you what, Sweetie?"

"Bitch. Why did you call me a Bitch?"

"Because you are, Sugar. You're my Bitch." She smiled broadly. "Now, let's start fucking."

I began to inch myself up her body, ready to lose my virginity. Before I could achieve the ultimate pleasure, Tanya stopped me.

"Not yet, Bitch." I paused as Tanya held me up. "I wanna fuck you, but you're not ready."

"What? What do you mean?"

"I want you to be my Bitch. You do want to be my bitch, don't you?"

"I-I guess so," I stammered.

"Great!" she exclaimed, and sat up. Taking me by the hand she led me to the bathroom and had me sit on the toilet seat. "I want you to be my girlie bitch," she explained as she started to apply make-into my face.

I sat there in a daze and allowed her to make me look like a girl. When she finished with applying the make-up, she handed me the red satiny bra and panties she had been wearing all night. I was robotic as the garments encased me. After the lingerie came the red mini-skirt and blouse top, tied just the way she wore it. The spikey, strappy heels followed. I looked in the mirror, when Tanya stepped out to get something, and thought I looked silly, but this was what Tanya wanted.

She returned with a wig of curly red hair and two silicone orb like objects, which she placed into the cups of the bra. After the wig was affixed, I saw the girl Tanya made of me.

"Okay, Bitch! Now we're ready to get fucked!" Tanya exclaimed. Her eyes were filled with lust, and I shivered in the knees. She led me back to the bedroom and had me sit on the edge of the bed. Her naked body was in such contrast to my fully clothed attire.

She walked to a closet and with her back towards me, wrapped a belt around her waist. It wasn't until she turned around that I saw the big, black strap-on. I felt my eyes pop out.

Tanya sauntered over to me, with the big rubber phallus swinging between her thighs. Stopping in front of me, she said, "Get on your knees and suck my cock, Bitch."

I slid off the edge of the bed and fell to my knees. I wasn't entirely sure why I did it. Tanya held the dock in front of my face and commanded me to suck it, again. I slowly opened my mouth and took it between my lips. I feebly fumbled my way with taking the fake cock in my mouth.

"That's it, Bitch, suck my cock." Tanya said with authority. "You're a natural cocksucker. I knew you would be."

I looked up at her with my eyes after that last comment, the phallus still between my lips. Tanya held my face to her cock and began thrusting in and out of my mouth.

"You'll be a fine assed bitch when I'm done with you," she proclaimed. "Keep sucking, Bitch."

My jaw began to get sore as she continued face-fucking me. Drool dribbled out the sides of my mouth and down my chest. Tears walked from my eyes and my knees ached. Still, Tanya berated me and called me "Her Bitch." I felt humiliated, although I was still aroused.

The bedroom door opened and Darryl walked into the room, catching me on my knees, dressed like a girl, and sucking on a cock. Our eyes met and I froze. Tanya began laughing and Darryl started to strip. I was completely confused and scared.

"Darryl is my man," Tanya began, "and he is your Master."

I tried to shake my head in disagreement, but she held my head tight, the dildo still lodged in my mouth.

"You are our white sissy bitch," she went on, " and you will serve us both." At which point she pushed me off her cock.

I tried to object, but found it difficult to voice my complaint. My throat was as sore as my jaw and my voice was hoarse. Darryl walked over toward me, as Tanya held me down by my shoulders. His large, black member swayed in front of my face.

"No teeth," Tanya warned me sternly.

Darryl held his cock in front of me, waiting for me to open my mouth. Tanya's fake cock lay on my shoulder, wetly, reminding me of my position. Tears filled my eyes as I meekly parted my lips.

His warm flesh filled my mouth and gradually expanded in size as I sucked on his salty man-meat.

Both of them now called me names, like, "Bitch," "Slut," and "Cocksucker." All the while Darryl's cock filled my mouth. I began to realize that I had to submit.

Tanya pulled me up by my hips to a semi-standing position. With my mouth still engulfed with Darryl's cock, Tanya slipped her hand under the skirt I wore and slid the panties aside to expose my ass. I knew what was about to happen, but I was powerless to stop it. I screamed in my throat when she pushed the black strap-on cock through my tight hole.

True to her word, I was indeed getting fucked, in more ways than one. The two of them dragged me to the bed, where I was subjected to rigorous sucking, fucking and name calling. And, through it all, I was still stiff.

When their lust was sated, i was tossed out of the bed. I laid on the floor, immobile, looking for my clothes, but couldn't find them. As if reading my mind, Tanya leaned over and whispered in my ear.

"You're wearing your clothes, Sweetie. Go on home, now."

I stood up and wobbled on my heels towards the door, when I heard her say, "We'll call you." I walked through the door nodding my head, knowing they would and knowing I would answer. I was the white sissy bitch to a powerful black Master and Mistress.

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AnonymousAnonymousabout 6 years ago
More needed

I agree that there could be more to Bill's feminization, like was he trained to drink cim, did he suck other guys from the club, was he trained to dress as a girl going to the club

SissiBobbiSissiBobbiover 6 years ago
good idea

Good concept but skimpy on the details. Much more could have been made iof the feminization of Bill and of his eventual acceptance of his role as their sissy slut. The story could easily go longer with further episodes of Bills feminization.

AnonymousAnonymousalmost 7 years ago
Lucky Bill

Loved the story only wish there was more focus on the feminization of Bill and his submission to the sexual demands of that big black stud. But then I am a feminized collared cock hungry Sissy,so no surprises there lol

Kisses xox

Sissytits Linda Crystal

FailedscoutFailedscoutalmost 7 years ago
Great Short

This was a very enjoyable and fresh short story, Of course I wish it would have been a little bit longer with a bit more detail but that's only because it was so good. Hopefully you will make up for it in the next couple of chapters ;-)

I hope to see more of this story and more from you.

Thank you for writing and posting here,

AnonymousAnonymousalmost 7 years ago
That was actually pretty good

That was one of my favorite stories in a while, good job

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