tagTranssexuals & CrossdressersBet You Didn't See That One Coming

Bet You Didn't See That One Coming

bygriffin57©

I looked down at my cell phone. The two way talk ID popped up. I shuddered.

"Hey baby, come out, come out, wherever you are. Be prepared, cause when I find you; You're going to find out that life is a bitch.!"

My God! What the fuck was happening to me?---------- I've created some kind of a monster! It was just a little joke. It wasn't even mean. I don't do mean. But here I am on the run!

The cell buzzed again. "Come on my sweet. Trina want's to play."

Lord help me! I might not last through the night! I have to be calm. I have to think about what started this whole fiasco. Last Saturday. Yeah, that's it. Last Saturday at the club.

*******************

I don't usually go to clubs, but here I was. I left my car and on the way in I thought I recognized another vehicle in the lot. The sun had just set so I had to look closer. Yup, it was Trevor's blue Prius alright, same 'beam me up Scotty' bumper sticker on the back. Trevor Martin is a co-worker I know. Not well, but we talk occasionally. We know where each other live; actually in the same apartment complex. Maybe we'd run into each other in there. That was cool, but no big deal, if we didn't.

I was just about to enter when I saw this hot chick, on her way out. Me being a gentleman; I opened the door for her. She thanked me in such a sweet voice, but jumped when we made eye contact. She had auburn hair to her shoulders and the famous little black dress, with 'fuck me' high heels. Her dress was tight enough to tell her blood type. Chanel #5 wafted in the air and I was mesmerized by what little I could see of her face. She almost ran to the parking lot. A hard task to do in heels. But the strange thing was that she jumped into Trevor's car and peeled out of the lot.

I was more intrigued with her than the damn club. Trevor got a girlfriend I didn't know about? Enquiring minds want to know. I jumped back into my car and headed for the apartment complex. He lived in a different building, but not too far, so I parked in my designated spot. I found his Prius and placed my hand on the hood. Yup, I think this gun had just been fired. It wasn't a long walk and I took the stairs to the second floor. I knocked, when I reached his door.

'Just a moment', I heard his voice. The moment stretched into 5 minutes. I know 'cause I checked my watch. What was he doing, hiding her? Finally the door opened. He wore a long bathrobe and black socks, looking a little disheveled. His long hair tied in a pony tail.

"Hey Rick; what's up guy?" He seemed more nervous than sheep at a farmers convention.

"Hi Trevor. Just wanted to ask you if you want to go out." I tried peering around him to get a glimpse of the dame I saw earlier.

"Nice of you to ask buddy. But I'm beat! Maybe next time." I could tell he wanted me out of there badly.

"You don't have a girlfriend, do you Trevor?" I wasn't so quick to go.

"Nnn--o." He replied. "W--hat makes you think that Rick?" Trevor acted like he was going to have a seizure.

"I swore I saw a hot chick earlier and she was driving your car." The color started to drain from his face.

"I---'ve been here all night R---ick." He stammered. I glanced down at his feet. I started. What I first thought to be black socks were really women's Hosiery. I reached across, before he could move and pulled on the sash around his waste. The robe opened and revealed a different story. He was wearing a black bra and panty set, complete with nylons and a garter belt. The hot chick was him!

"What were you lying Trevor?"

He turned white and then red. If he turned blue, I thought I was going to have to salute. "Mmmmy -----God. Rick. This isn't w--hat it s----eems!" He back peddled.

"Luuucy. You got some splaning to do." You know; a Cuban accent is really hard.

Trevor back away from the door in total defeat. I walked in and closed the door behind me. He plopped on the couch and held his face in his hands. When he finally looked up he was crying. I suddenly felt like a heel.

"No one has to know Trevor. I won't say a word." Shit anything to keep him from bawling his eyes out.

"Really?" he sniffed. "You won't tell anyone at work?"

"Scout's honor, Trevor. But I think you owe me an explanation."

I sat down in a chair as he spilled his guts. He said he had been dressing up since he was about 12. His Mom worked afternoons and his Dad drank his supper and was out by eight. Trevor was slight so his mother's clothes fit him. At first it was just the heels and then the panties and bra. Before he knew it he was into the whole ensemble, mom's wig and all. He also became very adept at applying make up.

One night his Dad woke up while Trevor was decked out. He staggered out of the bed room and snuck up to Trevor from the back. Dad put his arms around his waste and wanted to know ' Did you dress up for me darlin?' Trevor froze. He was mistaken for his Mom. He told him in his best 'mom' impression 'Yes sweetie. And if you go back to bed; you'll get a real treat.' His dad kissed him on the neck, slapped him on the ass, said to 'hurry up' and staggered back to bed. He was snoring moments later.

Christ; I thought that I was going to have to get therapy after hearing that.

Trevor was more careful after that incident, but continued his fetish. After he got himself a job and moved out his 'hobby' was upgraded and his wardrobe began to expand. He became more comfortable in the role and started going out to clubs. That's where it started getting out of control. Guys started hitting on him and feeling him up.

"I found out that I liked getting treated like a woman. But I'm not that way, Rick. I swear."

I thought about it for a bit. I had an idea. " I want to see you in full swing again Trevor."

"I tell you Rick; I'm not gay!" He stated flatly.

Oh, Fuck, no. He did not just say that! "That's not what I want." I assured him. "I just want to see how well you pass."

Trevor hung his head. "Give me 15 minutes Rick." He murmured.

Twenty minutes later he walked out of his bathroom. He didn't look like a super model but he was kind of a 'girl next door' hotty. He twirled for me. "What do you think?"

"What's your name beautiful?"

"My name is Trina, sweetie." His voice was even great.

"I'll make a deal with you Trina; you do me one little favor and I forget about this completely."

He sobered up. "What do you need me to do?" He was expecting the worst.

'Next week I have to go to a wedding reception for a girl cousin of mine. I need a date."

"Oh no. No no no no way. I told you I'm not Gay!"

"That's not what I want. My cousin is constantly on me about meeting a nice girl. I thought that if I brought you, she would get off my back."

"I don't know ,Rick."

"The family is loaded. The reception is going to be top notch. Great food, champagne, caviar, the works. It's my family, out of town and no one will know you. Free meal, free booze and you get to dress up. You don't even have to dance."

"And you won't tell anybody about my ---'condition'?"

"I swear on a stack of bibles." I was adamant.

"Ok, Rick. I'll go. But, only if you dance with me."

'Fuck! ---Ok." I relented. I told him when It was and what time I could pick him; I mean her, up. When asked what I would be wearing. I was confused but gave out the information.

********************

Time went by and we barely talked at work. I never mentioned our deal and neither did he. Actually it was better that way. I didn't need awkward situations at work. The time for the reception arrived and I went to go pick him up.

Trina answered the door and my tongue just about rolled out of my mouth. I was stunned! "Wow!" My voice was hoarse. " You certainly look the part." She was wearing a green gown that hugged her body in the right places. "Nice dress!" He/She even had cleavage. How the hell did that happen?

"Oh, this old thing." Her voice was low and sultry enough to start a stampede. She wrapped a fur stole around her shoulders and took my arm. "Ready Sweetie?"

I swallowed hard. "Sure." I squeaked.

**********************

The reception was in the middle of dinner when we arrived. My cousin; the bride finished eating and waved. She grabbed her new hubby and came to greet us. I got a big hug, a kiss on the cheek and the third degree.

"Who might this be, Richey?" I hated it when she called me 'Richey'.

"This is my friend Trina. Trina; this is my cousin Monica and her new husband Carl."

Trina got into the swing of things. "That is a beautiful gown, Monica! I love it." The two stepped away to talk as I congratulated Carl on the nuptials. We shot the shit for a moment and the girls came back.

"Richey; Trina is so sweet. Glad you found someone. I was thinking you were becoming a rump ranger." She giggled at her own joke; actually it was more like braying." So, how long have you two been together?"

"Three weeks." I lied. Unfortunately Trina answered at the same time and said 'months' instead of weeks.

The bride was confused. "Is it weeks or months?"

Trina spoke up. "When you're in love; what does time matter?" She cupped my ass cheek and I flinched.

"That's so romantic Richey!. See Carl; it isn't that hard." She admonished. She turned back toward us. "Now you two eat before they take away the food." And they were gone.

I turned toward Trina. " 'When you're in love'. Shit! And leave my ass alone." She actually had the nerve to laughed at me.

We ate dinner. I introduced 'Trina' to all of my family, including my parents, and they all found her 'charming'. The food was cleared away and the DJ appeared. After the Bridal party, and the rest of the introductory dancing was done, the floor was open to all. Trina' took my hand and drug me onto the floor. Thank God I had enough liquid courage in me.

We started dancing a few fast numbers and I heard the DJ say 'time to slow things down a bit'. Crap! My solution was to dance like they taught us in 4th grade. Enough space to hold a basket ball between us. 'Trina' wasn't having any of that.

"If you don't hold me closer Rick, I'll take your mother into the bathroom and show her what I really have between my legs." Damn. I was fucked! I pulled her tight. "Now that's better baby."

We danced around 6 more tunes and I felt like had fulfilled my part of the bargain. 'Trina' pouted, but acquiesced. I went to sit down and talk to one of my guy cousins. My Mom came over after a bit and hugged me. She was beaming.

"Trina, just told me that the two of you are thinking about getting married." I had just taken a sip of my beverage and ended up spitting it all over.

"What?" I uttered.

"Trina said that you wanted to make it a surprise later, but she couldn't wait. She's so sweet." I stared in disbelief. "She told me that you guys were trying to have kids. You know that your dad and I have wanted grandchildren for a long time."

This wasn't going as planned. I looked over and 'Trina' was setting with my Dad. She kissed him on the cheek and they hugged. What the Fuck! Someone thumped me on my back. My cousin Bill smiled at me.

"You're fiancé Trina told me you guys were getting married next June. You lucky dog. You didn't have to keep it a secret from me." If a goat had crawled out of Bills ass, I wouldn't have been more surprised. This was getting way out of hand. Some one else tapped me on the shoulder and I turned. 'Trina' planted a lip lock on me before I could move.

"I missed you sweetie."

"Trevor!" I spoke through clenched teeth.

"Trina!" She replied melodically.

"Ok, TRINA!" I growled. "What are you doing to me?"

"I was just getting to know your family, baby."

"I don't want you to get to know my family, TRINA!"

"When is she going to throw the bouquet Richey? I want to be in the front row."

"Don't call me Richey! And you're not going to catch that Fucking bouquet! Got Me!

Her smiled disappeared. "If you are going to start being mean, you can take me home." She snapped.

"My pleasure 'Trina'. Grab your stole and purse and let's get out of here." I was pissed!

Ten minutes later we were headed home. 'Trina' spoke. "Turn left up here, Rick."

"No way! I'm not turning here." I heard a click and spied a pistol pointed me.

"Feel like turning now Ricky?"

"W---hat's the gun for Trevor?"

"It's Trina, Richey! Now turn left or I'll ventilate you."

I followed directions. We arrived at a house. The lights were off. She kept the gun on me. She stumbled over a crack in the sidewalk and I ran. I went behind the House and through a gate. It was a fenced in yard and a fucking dead end. My cell went off.

This is where we came in. I tried whipping back down the path. Trina was waiting for me, gun in hand. She had me! Within minutes we were inside. She turned on some lights and we walked downstairs into the basement. It was finished in early Medieval. There were chains with manacles attached to the wall. I also saw a padded table with hand cuffs. I didn't even recognize the other types of restrains, but all of it made it look like a dungeon. He/ She was definitely into bondage.

"What's going on, Trevor? What are we doing here?"

"It's Trina, baby and you're taking off your clothes."

"What did you say?"

"Clothes; shuck them Richey!"

I got down to my under shorts. "Over there Romeo." She used the gun as a pointer. In moments I was on a platform of sorts, cover by some kind of carpeting. I was face down and my hands and ankles were shackled. There was the sound of machinery moving. The lower half was bending down like in a drop leaf table. My ass was very vulnerable. Trina moved around front so I could see her.

"Don't bother yelling, the basement is sound proof." As she talked she disrobed. "You see, this a little game I like to play 'cause I need fresh meat for my kinky side." Her dress hit the floor and she stood there, looking much more like a woman, than before. Her bra was the next to come off. Her tits looked real! No wonder it looked like she had cleavage.

Trina was smiling as she wiggled them at me. "Yes they are real baby. Grew them myself with hormone therapy. Of course I have to bind them at work and wear baggy clothes so that no one knows my secret." Her panties came off next, but there was no mystery about the bulge she had. Her cock rolled out of her under ware and almost smacked me in the face. It was huge! Trina was a transsexual!

"I use to be Trevor Rick, but Trina has much more fun." She waved her cock in my face. It started to rise on it's own. "I was going to fuck your face for a while, but my little pet is very hungry and all she eats is ass meat." She moved around me and giggled.

"We can work something out Trina. I'll suggest you for the next promotion at work. I'll give you money, anything you want. Please, for Christ's sake."

She moved behind me. "Oh your going to give me something all right. I'm going to add your cherry to my collection." She slid behind me. My shorts were ripped off my body and I felt her hands on my ass. " Such prime meat baby." She slapped both of the cheeks.

"Please Trina. Don't do this!"

"You'll love it Rick. It's an expanding experience." She smack my ass again. " Now tell me you love me and beg for my pet and maybe; just maybe I'll use some lube."

Shit. What was I to do? She had me over a barrel; literally! "Trina. I love you and---." I couldn't say it.

"And you want my beautiful cock in your ass sweetie." I got cracked again.

I yelped in pain. "Trina. I want your beautiful cock in my ass. Please fuck me!"

"Why Rick; I'm touched by your tender plea. Yes; I will fuck your ass, since you asked so nice." I felt the greasy lube running down the crack of my ass. I felt pressure on my anus. "You are a tight one baby, but all good things come to he who waits."

She shoved and I felt like I had been split open. "Relax baby, that is the key; Relax."

The pain had subsided and she pulled out a bit. Not all the way, mind you and then SLAM. She was buried to the hilt. Over and over, picking up speed.

"This is so heavenly baby. You should feel it."

Make no mistake; I was feeling it! Every fucking inch. Her assault on my back side continued.

"I just love popping the cherries of candy asses like you Baby. I love a good tight, bitch. You want to be my bitch sugar? I'd like to do this all night, but you're so tight I don't know how much longer----I can last."

She stopped her pummeling. " I have to take a breather, Rick. I hope you don't mind."

"Why no. Trina." I spoke through gritted teeth. "Please,take all the time you want." My ass was numb anyway.

"Whew, Baby. You're tiring me out. But you know what they say; 'no pain, no gain." She started pounding me again. " I" thrust "Don't" Thrust "Want" thrust " You" thrust "To" thrust "Forget" thrust "Me".

'No chance of that' I thought. Her pounding reached a crescendo and she screamed. Trina collapsed on top of me, breathing hard. She kissed my cheek. And preceded to release me.

"Don't even think of retaliation Baby. I video taped our little play date and it will be sent to our workplace, if you touch me. Let me know when you want another go round. I'll bring a friend. "

I was free and stood up on unsteady legs. Her bare ass swished as she headed for the stairs. I was raging! I didn't care what would happen. I leaped after her and grabbed her by the hair. She screeched as I drug her back to the platform, which was now flat again. I threw her down and grabbed her ball sack. I pulled her hair and forced my dick to her mouth.

"Start sucking Bitch; or I'll crush your balls! I'm I charge now." Her mouth opened to scream and I shoved my dick in it. She gagged, but started doing as she was ordered. I let go of her balls and forced her head to turn. I took her in hand and face fucked her, until I was hard as steel. Drool pooled out of her mouth and dripped on the platform. I threw her back down and pushed her on all fours. I manhandled her ass for a line up shot.

"No." She pleaded. "I'm a top only."

I laughed. "Time to update your resume 'Baby'." I plunged into her ass. My intension was to abuse hers as she abused mine. I gave her full thrusts and she yelped with every one. The pressure built up and soon I was hammering her. We both shouted as we came in unison. I collapsed on her back as I fought for air. Her breathing was ragged as well. I fell to the side and took her in my arms. Our kiss was deep.

"What did you think, Baby"

"Wow." I breathed.

"Told you that role playing would be fun!" She was right; it was outrageous!

Bet you didn't see that coming!

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