The Trans Ultra Collection Vol 2

by Ursula Lovelace

  Derek Grayson had given me a sizeable war chest to wage war with. It also meant that Adam Grayson had lost the financial and political backing of one of his biggest supporters. This was a three way race between Grayson, Jenkins, and me.

  I had also set up a donations website. I put some layers between me and Robin Smith so that the money wasn’t linked to Robert Brown. With how much I was getting in donations, the IRS would probably have a good look at Miss Smith’s financials. I needed to be careful with my paperwork or risk ending up in a white collar prison.

  Regardless, I made sure to let everyone know who Robin Smith was and what she stood for. I made sure my beautiful face was plastered over the streets and the internet. I didn’t have to do much since my growing fan base did much of the legwork.

  A Facebook fan-page swelled to the hundreds of thousands. There were more people following me on twitter than the total number of eligible voters in my district. My message was connecting with people all around the nation.

  My rallies matched the intensity of my online following. Each venue would get sold out within hours. People would camp just to get a glimpse of the sexy, charismatic Robin Smith. I was told that my rallies were becoming a fire hazard from the sheer amount of people attending them. Those that didn’t get in tried to camp outside in order to hear me speak.

  It helped that the media treated me like a sex symbol. I was a breath of fresh air in a district wanting change. Next to an old man, I practically looked like Angelina Jolie running for office. Men loved me and women wanted to be me.

  That didn’t mean I was in for an easy election. Grayson saw my candidacy as an act of war. Even without Derek Chambers backing him, he still had money flowing into him from all over the nation. As a longtime incumbent, he had plenty of campaign material to work with. Despite his scandals, the man had a number of bills he had sponsored or created.

  As for me, I didn’t have a single piece of legislation under my name. I couldn’t tie myself with any Republican programs either. As an independent candidate, I was the enemy of everyone.

  Instead, I had to rely on my looks and my message. I was counting on my popularity versus that of my opponents. Not that Grayson was popular to begin with. This was the area where I could make up the deficit. I played up the age difference by declaring myself as ‘A Modern Representative for A Modern Time!’

  It helped that Grayson looked absolutely ancient next to me. It was why he never scheduled a debate at the town hall. The man said I was not worth his time but I suspected another reason. Even if he could beat me in a debate, the man wouldn’t look glamourous in a photo next to me.

  On the other hand, Jenkins was young and handsome. However, he was a recent divorcee and didn’t have a happy family to parade around for photo shoots. The man was also untested at politics. The people saw the Republican candidate as just another part of a broken system.

  Of course, Grayson and the others struck back at me. The biggest claim was that I was a young, inexperienced woman. Grayson even said I should be disqualified due to a lack of a college degree.

  Well, it was true. I couldn’t conjure up a diploma out of thin air for Robin Smith. However, they quickly pulled that ad after backlash from voters. A good portion of the district didn’t have a college education and thought Grayson was acting elitist.

  As for Republicans, Jenkins was swirling down the drain. In spite of his youth, the man was seen as another corrupt insider. The bill and committees he had linked himself to weren’t popular around these parts. The district had always been hard for them and my entrance didn’t make things easier.

  They were careful not to go too hard on my gender. Polling showed that the women and youth vote was heading my way. Grayson and the others didn’t want to alienate them more than they already had.

  Furthermore, the sitting Representative hadn’t covered himself in glory after shutting down the records office with false embezzlement charges. During his campaign trail, the man was always on the back foot and trying to avoid fielding questions about his scandals. By now, the chickens were coming to roost, especially with my criticisms about his corruption.

  The fact I was a newcomer helped more than it hurt. Sure, I didn’t have any bills under my name. At the same time, I didn’t have scandals or controversies. I knew the other candidates were probing me for any piece of corruption they could hold against me. However, Robin Smith had a clean sheet. Even muckraking reporters were bewildered by this mysterious candidate.

  I couldn’t blame them she didn’t come into existence until a few months ago!

  It helped that Derek Chambers was supporting me. More than his money, his public backing had given me some much needed legitimacy. Other big players followed the leader and shifted their monetary and political support to me. Soon, I had more money than I could reasonably spend on the campaign. All in all, Derek had really come through for me.

  It wasn’t a bad exchange for a blowjob.

  It helped that I was a natural giving speeches and interview. This was surprising since I had always been shy as a man. With a skirt, reporters were dying to hear me give a soundbite.

  I talked about the longstanding corruption in the district. I talked about the jobs that had been lost due to it. It resounded well with the people who had been hurt by Grayson.

  Soon, the race was attracting national attention. For a seat in the House of Representatives, a lot of money was being spent on it. Without Chambers footing the bill, Grayson had to call in every favor he had. Counting all the major players, the tally was closing in on over ten million dollars.

  Despite my popularity, I was still an underdog. As an independent candidate running under the newly minted Justice Party, I didn’t have the history of the other candidates. Grayson still had a merry band of loyalists.

  I started to think of an exit strategy and how to retire Robin Smith. The thought of leaving her behind felt depressing. I had never felt so proud of myself and what I was doing. At least I would have wounded Grayson and brought up his corruption to a national level of scrutiny.

  Until that day arrived, I still had to campaign. I was on the road as voting day approached. Having secured the women’s vote, I focused on areas where Grayson was most vulnerable. Many of his longstanding supporters were looking to jump ship. As it was, Grayson and I were in a deadlock. I would need to win undecided voters to my cause.

  I focused on how much of a disaster Grayson had been to this district. We were the laughingstock of the state due to his corruption. I slammed him on the runaway bill for his legal fees. The man was constantly battling scandals in courts. My speeches got standing ovations from the crowd. I just hoped I would have enough votes for Election Day.

  I wasn’t even sure why I was working so hard to win. I had entered the race to take a stand against Adam Grayson. I wanted revenge against him for hurting innocent people like me. Instead, I found myself believing in my cause.

  The weeks before the big day were some of the busiest days of my life. I went to rallies and then to photoshoots before heading back for another rally. I had to outwork Grayson and the others if I wanted to seal this deal. It helped that I was younger and more photogenic than my opponent.

  I got a boon when I received word that the Democrats were in disarray over Adam Grayson. A number of leaked conversations revealed that many longstanding Democrats disapproved of his various scandals. They weren’t going to swallow their pride and pretend to be team players. Some of them even withdrew their endorsements of him. Nonetheless, polling suggested that he still had a slim lead over me.

  Still, it was a close race for a man like Adam Grayson. I had given more of a challenge than any other candidate. It was going down in the history book as one of the most expensive races in the history of the House of Representatives. Without Derek Chambers backing him, Grayson had to shake down everyone he knew for donations. It seemed like every ad on television was about one of us. There were still a few days until election so we both had cash to
burn for a last minute media blitz.

  I wasn’t sure what I would do if I lost. I loved being Robin Smith. More importantly, people were in love with me and what I stood for. A woman like me couldn’t quietly disappear into the night after a defeat. Nonetheless, defeat was a solid possibility according to polls.

  As for my Republican rival, Tom Jenkins was going to be a footnote in the district’s history. The man’s voting base was more likely to vote for me or stay home than show up at the booth for him. As much as I had wooed Grayson’s voters, I had also won over some of Jenkins’ supporters. The man was just too unpopular with no real message to his name. With a week until the election, his defeat was a foregone conclusion.

  The real race was between me and Grayson. The sitting Representative had never lost an election. In fact, practically all of them had been by a landslide. I was giving him the toughest fight of my life. If I lost against him, then at least I could claim that the margins were close.

  The last minute polling didn’t fill me with much confidence. Grayson was winning the wealthy neighborhoods. However, he was also winning some contested areas by a hair. I didn’t expect to win his core but I needed to win the sections that were balanced a on a knife’s edge.

  It wasn’t all doom and gloom. I was winning some middle-class and working class neighborhoods that had historically backed Grayson. However, they weren’t the most populous parts of the state by headcount. I’d need to tip the scales in more dense neighborhoods within district lines to win the election.

  By Election Day, I had done all I could’ve done. Exhausted, I rented a private suite in an out of town hotel to get away from the media. Win or lose, I would need a long vacation after this.

  I didn’t even bother to watch the news about how the race was going. Instead, I’d pour myself a bottle of alcohol and learn the results through my Twitter feed. I didn’t want to be disturbed by anyone. Only Derek Chambers knew where I was.

  I hadn’t even prepared a concession speech. I loathed the idea of even calling Adam Grayson and congratulating him for his victory. At least I wouldn’t have to deal with reporters. As a sexy woman entering politics, I was like chum to sharks as far as they were concerned. I didn’t know how politicians lived under constant media scrutiny. It was even worse for me since I was a man masquerading as a woman for political office.

  I did catch from my Twitter feed that it was a dead heat with Adam Grayson. The suburban middle-class areas were reporting and were in my favor. None of the networks were calling it either way. It would come down to the wire. I wasn’t sure I’d be able to stay awake that long.

  That’s when I heard a knock at the door.

  Chapter 5

  I got up to see who was knocking. I wasn’t expecting room service. I hoped no reporters had tracked me down here.

  To my surprise, it was Derek Chambers. “Derek? What are you doing here?”

  “Just here for a quick chat,” he said, making his way into the hotel room. Derek had a strange look in his eyes. “I hope you don’t mind.”

  The man had practically bankrolled my entire campaign. I couldn’t refuse him even if I wanted to. “Come on in. Want a drink or some room service?”

  “No, there’s something I want to talk to you about,” Derek said. I worried he had found out that I wasn’t actually a woman. “There’s a discrepancy with your records.”

  “Can’t this wait?” I asked, my heart thundering. He could go to the public with this information. I wouldn’t just be out of the election. I’d be behind bars. “We’ll hear the results any minute now.”

  “It can’t,” he said adamantly. “I know you’re not from around here, Robin.”

  I looked back in confusion. “What do you mean?”

  “Your address,” he replied. “It’s a fake. No one with your name lives there. Hell, it’s being zoned for demolition. One of my accountants found out and told me. What’s the story behind this?”

  The gears in my head quickly turned. By now, I was a skilled politician. I could come up with a believable lie on the spot.

  “I’m technically not from the district,” I answered with a half-truth. “I wanted to run up against Adam Grayson. However, I needed to be a resident in the district for two years in order to run. With the deadline being months away, I needed to make it look like I had been living there for years.”

  Intrigued, Derek sat down opposite me. “How did you pull that off?”

  “There were a lot of people upset at Grayson after he closed down the local government records office,” I explained, crafting my lie as I went along. I tried to look as natural as possible while spinning my tale. “A few of them lost their jobs because of it. I reached out to one of them and he agreed to make it look like I had lived in the district for years. It allowed me to run for office.”

  Derek looked impressed. “Huh, that’s clever.”

  I smiled. “Thanks.”

  “It’s also fraud,” he said, looking serious. “I could land in hot water with the IRS for funding you. Even if you win the election, you could be kicked out of office if someone found out about this.”

  I folded my arms and flashed a smile at him. “I won’t tell if you won’t.”

  He shook his head. “This is serious, Robin. My reputation is on the line. People end up in prison for less.”

  “We’re in this together,” I sighed. It couldn’t end like this, especially with the results approaching. I needed him to keep quiet about this. “What will it take for you to keep quiet about this? I can give you political favors if I win.”

  Derek gave a sinister smile. “I’m going to need a more… personal favor.”

  I recalled the blowjob. My heart sank at the thought of being blackmailed again. However, I didn’t have a choice. “Do you want me to get on my knees?”

  He got up and reached out to feel my breasts. Thankfully, my gel padded bra felt like the real deal. “I want something more.”

  That was a bit of a problem. I may have fooled him with a fake bust but a cunt was much harder to fake. If he still believed I was a woman, then he was in for a surprise if he lifted up my skirt.

  “How about my ass?” I offered, scrambling for ideas. “You get your way with it if you keep quiet about this.”

  Derek didn’t reply. Instead, he led me to the bed and gave my ass a squeeze. Strange as it was, I didn’t mind having him run his hands over my body. By now, I had been a sexy woman for months. I liked it when a man became attracted to me.

  I felt a strange shiver down my spine. When I had sucked Derek’s cock, I had done it to secure his backing. Now, I didn’t care if he was extorting me. I wanted him inside of me.

  It helped that Derek was utterly in lust with me. I knew when a man wanted me more than anything else in the world. As a woman, I had this innate charisma that attracted people to me like a siren’s song. It was how I had gotten so far as politician.

  With casual ease, I turned around, got on all fours, and hiked up my skirt. When I pulled down my panties, I was careful to hide my balls. Thankfully, Derek was too busy unbuckling his belt to notice anything strange.

  With his cock out, he wet his finger with saliva and brought it against the rosebud of my ass. He slicked it by tracing circles around it. I groaned when I felt the tip of his finger enter my ass. “Ah….”

  It felt odd to be penetrated this way. It actually felt nice after a moment. I got used to his finger making its way into my ass before steadily thrusting in and out. Soon, he started to insert another finger into me.

  I got more and more into by the minute. I loved how my tight sphincter fit his fingers like noose. For someone being blackmailed into sex, I was enjoying this ass fucking more than I had expected to. My fingers dug into the bed as I let out another moan. The tension of being caught as a man heightened my pleasure.

  Derek took his cock and stroked it. Within seconds, he was hard as a rock. He wasn’t the only one with a throbbing erection. I was so hard that my cock felt trapp
ed in my panties. I had to resist the urge to reach down and fondle myself. I had never felt so aroused before this moment.

  Finally, Derek began to penetrate my rosebud.

  It was incredible.

  The man’s cock was longer and thicker than mine. It stretched my ass to its limits. As much as I was enjoying it, Derek sounded utterly ecstatic. “God.., Robin, you’re so fucking tight!”

  I could feel every inch of his cock come in contact with the deepest parts of my ass. I was just as lost in the moment as he was. “Fuck me with your prick!”

  We were both locked in this erotic coupling. The pleasure overwhelmed my senses. My body reacted to Derek’s thrusts as if it was on autopilot. My rosebud grew tighter and tighter as he probed deeper and deeper.

  With my ass clamping down on him, the man was the highway to an orgasm. Derek gripped my hips and thrust into me wildly. “I’m going to come, Robin!”