The Trans Chronicles

Published on Feb 14, 2023

Transgender

The Right Wrong Decision

The Right Wrong Decision

Sometimes when you are upset you should just calm down and wait it out. Other times, a seemingly bad decision can turn out to be great one. Of course it depends on your perspective.

Several years ago I was dating a woman who was completely overbearing. If I did anything that didn't include her, her jealousy would make my life miserable for the next few days. Sometimes it was bearable because she would grudge fuck me. She was rough and would slap my ass or roughly pinch my nipples. I actually liked that sex over what was "normal" for us. At other times it was just incessant bitching that made me want to fucking kill myself!

These not rare events ended one night when I decided I had had enough. I decided to hit the town on my own. I began touring the various clubs while drinking liberally. I had the forethought to leave my car at home and Uber myself around town.

At one in the morning I stumbled out of a club and met my Uber driver.

"Where to?"

"Anywhere that is still open."

Without another word he took off and a short time later he stopped in front of a club called "The Masquerade." I had never heard of the place but strode in confidently. I bellied up to the bar before I ever took in my surroundings. Even when I surveyed my surroundings it didn't dawn on me I was in a LGBT club. There were plenty of men and women in the place and my dulled senses never recognized they were paired up the wrong way, at least from my experience.

I was into my second beer when a lady approached me.

"I haven't seen you here before." she said. "I'm Tamara."

Tamara was tall for a woman. Taller than me. She was also African-American. I immediately focused on her amazing rack. I am a white guy and never dated a woman of color. Not because I didn't want to or wouldn't but I had never been in a position to.

"Hi Tamara. I'm Todd."

"Mind if I join you?"

"Not at all. Can I buy you a drink."

I had decided maybe I might just try to hook up with my first woman of color. I felt my groin stir at the thought. I was pissed enough at my girlfriend and was pretty sure I was done with her.

After a few more drinks it was really late and I decided to give it a try.

"I'm about ready to call it a night." I said.

"Is that a poor excuse for an invitation or are you really just going to leave me languishing on the vine?"

I'm not the best at picking up subtle signals from a woman but luckily Tamara wasn't subtle at all.

"I guess that was a poor invitation." I smiled. "I took an Uber here. Do you have a car or should I make a call?"

"I have a car sweetie. Just point me in the right direction."

It was a short drive to my apartment. When I closed the door behind us Tamara became very aggressive. She took me in her arms and began passionately kissing me. She was strong and I don't think I could have escaped her grasp if I tried. She nearly ripped my clothes off of me and drug me to the bedroom. My clothes lay strewn about in the living room. I found her aggressiveness extremely exciting.

After pushing me onto the bed she began to slowly strip. When she exposed her breasts I could tell they were fake. Whoever did them did a great job but they were fake nonetheless. I touched myself but Tamara told me no. Only partially nude she pulled something out of her purse. Turns out Tamara was kinky. She wanted to tie me up but that is when I got nervous. I thought maybe she was going to tie me up and rob me. She sensed my apprehension.

"Sweetie, you have nothing here I want. In case you didn't notice that was a Mercedes you rode in just a minute ago."

Reluctantly I let her bind me to my own bed.

"You won't regret this honey." She purred as she tied the last strap to my spread eagle ankles.

She then began a sensuous striptease of the rest of her clothes. With her back to me she lowered her panties. Her ass was exquisite. Nice bubble butt you always dream about. When she turned around I yelled out.

"What the fuck!"

"What's the matter?" Tamara was genuinely surprised at my response.

"What the fuck!" I repeated.

"No, what the fuck is the matter with you. You go to a gay bar and think you are picking up a girl?"

"Gay bar?"

"Yes a gay bar. Did you not know or figure it out when you looked around."

"No...no."

"Well sweetie maybe you knew it but just didn't want to admit it to yourself. After all that cock of yours is as hard as it has been since I stripped your white ass at the door."

Tamara was right. Seeing her huge black cock surprised and scared me but I was still excited. Since I didn't offer up any further protest she took that as a sign. She climbed on the bed and straddled my chest. Her rather large cock was right there in front of me. I could smell her "manhood." She reached behind her and took my cock in her hand.

"Doesn't feel so bad does it?" she asked while slowly stroking me.

"No." I meekly replied. "It feels good."

"You like looking at my big black cock too don't you?"

"Yes."

"You want to taste it don't you?"

"No!" I almost yelled.

In response Tamara pushed the head of her cock down toward my lips. "Open that mouth you little pussy ass cock sucker!" The head of her cock pushed against my lips but I wouldn't open my mouth. "Do it now or when I fuck that ass I won't be gentle."

At that point I was honestly terrified. This big black tranny was getting ready to rape me. I opened my mouth to the inevitable. She pushed in and I tasted cock for the first time.

"Baby that mouth feels good on my cock."

I didn't realize it but I was bobbing my head on her cock. It was like I was enjoying myself or something. Moans of pleasure from both of us were filling the room.

"Damn! I didn't think you would be that easy!" She moaned.

This went on for a few minutes before I began to sense Tamara was going to cum. Instead she pulled out of my mouth.

"No, no, no... not yet baby. I'm saving that for your ass."

I lay there helpless. I was at her mercy. She could do what she wanted and she was going to do what she wanted whether I liked it or not.

Again she retrieved something from her purse. It was a bottle of lubricant. She applied it to my ass. For several minutes she probed my ass with first one finger and then two, maybe even three. During this time she would also tease my cock. Sometimes gently sucking on me, other times slowly stroking my shaft or fondling my balls. Eventually she pulled away. I watched as she applied the lubricant to her cock and then climbed between my legs.

"Baby, I'll give you one chance to tell me to stop. I'll untie you and walk out of here. Otherwise I own that ass."

I just stared into her eyes. I believed if I told her to stop she would. At the same time I knew I didn't want her to stop. I felt tears welling in my eyes because I wanted to be fucked so bad. What the fuck was happening to me?!

Tamara pushed he cock toward my opening.

"Yes..." I whispered.

He foreplay with my ass resulted in an almost effortless entry of her cock. She pushed in almost half of her ten inches. I gasped at the sensation of being filled with cock.

"Oh my god!" I moaned. "You feel huge."

"I am baby. You only got about half of it."

"Please..."

"Please what baby?" she cooed.

"Please...fuck me."

She did. At first it was slow but the pace picked up. I could feel more and more of her cock penetrating deeper and deeper. It hurt but felt wonderful at the same time. I was about to cum myself when I heard her.

"HOLY FUCKING SHIT!"

Tamara stopped pounding my ass but didn't pull out. She just looked over her shoulder at my girlfriend and then down at me. "Who is that bitch?" Without waiting for an answer Tamara again began to slowly fuck me.

"Uh!" I blurted out as she pushed ever deeper. "She's...ugh...my...oh fuck...girlfriend."

"Girl, you just gonna watch or you gonna join us?"

Kelly is my girlfriend's name. Interesting that I got this far into the story before I even said it. That should tell you something.

Kelly just stood there dumbfounded. Tamara quickly got her pace back to where it was and I could feel my orgasm building as his cock pounded against my prostate.

"Ohh...fuck yeah...ohhhhh" I moaned as I exploded cum onto my stomach.

"Baby that is so hot!" Tamara said and then shortly after she filled my ass with her cum. Her thrusts became a little less controlled and I yelled out in pain with pleasure.

For a minute I had forgotten all about Kelly but she was still standing there watching us. Tamara got off the bed and stood in front of Kelly. Kelly stared at her in disbelief. Even after her orgasm, Tamara's cock was intimidating.

"You staying or going?" Tamara asked.

"You are a fucking freak!" Kelly yelled at me.

"Staying or going?" Tamara repeated.

When Kelly didn't move Tamara put her hands on Kelly's shoulders and pushed her to her knees.

"If you are staying you need to clean this up." Tamara pulled Kelly's head toward her cock. Shockingly Kelly opened her mouth and began to hungrily suck and lick his cock like I had never seen her do before. I watched and was amazed at how quickly Tamara could recover. Soon she was hard again. What happened next blew my mind more than anything. I watched Tamara grab Kelly by the back of the head and face fuck the hell out of her. She never tried to pull away. Tears poured from her eyes and I actually felt sorry for her. It went on for several minutes before Tamara finally came. Kelly gagged on part of Tamara's load and the rest shot on her face.

When Tamara was done she came over to the bed and untied me. She pulled back the covers on my bed and we climbed into bed together. She pulled me close, spooning me from behind, the heaviness of her cock firmly pressed against my ass.

I heard Kelly leave and have never seen her again. Tamara on the other hand. She uses me whenever she pleases.


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