The Trans Ultra Collection Vol 1

by Ursula Lovelace

  I clinked my glass with his and took a sip. “I’m not supposed to drink on the job. Or get frisky in public with a passenger. I’m pretty sure that’s in the Uber rule book.”

  Charles finished his drink and poured himself another. “I’m sure they’ll make an exception in this case.”

  It felt strange to be the one in the lap of luxury. Sure, I had dolled myself up tonight but this was another level. Worse, Charles was making me hot under the dress. My cock threatened to slip out of the edge of my panties. It made me remember that I was a man cross-dressing as a woman. I took another helping of champagne to cool down.

  Charles filled yet another glass. “You’re the first woman I’ve invited to my suite since I came here, Tommy.”

  I giggled. “Really? What makes me so special? Other than that I know the fastest route to the beach.”

  “That’s a neat skill to have,” he chuckled, leaning in closer. “No, you’re plenty interesting. Much more than you give yourself credit for.”

  I suppressed a shudder when I heard that last statement. I wondered if he had suspicions about my identity. If he was suspicious, then he would probably have called the police and kicked me out. “I doubt that. What makes me so special compared to the other women you’ve met?”

  “You seem so genuine,” Charles said with a soft laugh. He got up and sat beside me on the bed. There was plenty of space for the both of us. “In all my travels, I’ve never met anyone like you. You’re so kind and humble. Most people I’ve met are deceptive and snobbish.”

  “Well, humility is my greatest virtue,” I replied, watching him prop two pillows over each other. He sat back against the bed with his legs stretched. “Hell, I’d consider it a job requirement.”

  Suddenly, Charles placed his glass on a nearby dresser drawer. “I think that’s enough talk. Let’s begin, shall we?”

  I gulped. “Begin?”

  Before I could even react, Charles approached me on the bed and spread my legs. He looked like a jungle cat stalking his prey. The man spread my legs even wider.

  I didn’t know whether to stay or flee.

  Thankfully, Tommy made the decision for me. I instinctively reached down to touch myself. One hand teased my balls and the other kneaded a fake breast, Charles couldn’t notice the bump in my panties if I touched them first. It felt all too natural to touch myself in front of a handsome man I had just met.

  God, it felt amazing.

  What was even better than that feeling was the sight of Charles undressing. I watched as his toned muscles came into view. I gasped when his large cock sprung free from his pants. He was like a living marble statue chiseled to perfection by a master sculptor. The man was much better endowed than me.

  I was drawn to his body like a moth to the flame. He just radiated power and vitality. I knelt down on the bed before him as though it were an act of worship. I couldn’t help but marvel at him. “Charles… God you’re beautiful.”

  Without saying another world, I moved closer to him. My heart thundered in my chest like a live time bomb. I reached out to grasp the base of his cock. Charles leaned back as I felt the wiry hair of his crotch rasp against my hand. It was utterly massive and he wasn’t even fully erect.

  Without the slightest bit of reluctant, I pumped him from shaft to tip. The heat from this pleasurable friction was overwhelming. “This is so hot... Charles.”

  Charles groaned. “Touching you is even better.”

  I remembered how he had touched me back at the bar. It had been the craziest thing I had ever done at that point. He could have easily discovered that I was a man cross-dressing as a woman.

  Now, I was giving him a hand job while my other hand touched myself. I couldn’t help but moan. “God… this is wild. Ah!”

  He was hard as a stone and showing no signs of softening. In fact, it didn’t seem like he was fully erect yet. I continued to play with myself to the rhythm of my strokes. I only stopped when I felt his cock grow taut.

  Charles moved up to undress me. However, I quickly stopped him. “No, I prefer it this way.”

  He smiled and looked at me with his beautiful eyes. The man’s mere gaze gave me the chills. “Of course…”

  Charles seemed absolutely smitten with me. His breathing grew more ragged. His erection was painfully stiff.

  That made two of us.

  I prayed my cock didn’t spring up from beneath my panties. It was a hard ask because I was more aroused than I ever had been before in my life. However, there was no stopping now.

  I shuddered as my prick pulsated with desire. My nipples also hardened under my padding. It was my first sexual encounter with a man but I had taken an immediate liking to it.

  I longed for his touch. My skin felt unusually sensitive. I wished I could undress and have him touch me wherever he wanted. I knew Charles was a skilled lover through our brief foreplay at the bar. I couldn’t stop this encounter even if I wanted to.

  With how his cock twitched, Charles couldn’t either. My lover stood up and approached me. He looked like a man on a mission.

  Finally, he reached out and kissed me.

  As much as I was taken in by this passionate kiss, I couldn’t help but notice my erection making a tent under my skirt. I wasn’t as big as Charles but it was noticeable enough. I prayed that he gave more attention to the rest of my body.

  I didn’t know what he saw in Tommy. It wasn’t like I was a gorgeous woman with a sexy figure. Sure, I always had a girlish built but I wasn’t exactly super model material. Nonetheless, Charles worshipped my body as if I were an ancient Greek Goddess of Love.

  As I locked lips with Charles, he took my hand and brought it to his cock. I stroked it and felt his hardness before moving down to cup his balls. Without breaking the kiss, Charles massaged my fake breasts and caressed my back. They seemed believable enough to him. Even though my lover didn’t touch my sex, I was on the highway to an orgasm.

  The fact I was a cross-dressing man making love to another man was nearly enough to make me come. More than anything else, this felt real in spite of my disguise. Yes, this was lovemaking. It wasn’t rushed or devoid of passion. This wasn’t some one night stand. Charles wanted to take things slow.

  He groped my breasts and ravished my neck with kisses. I looked at him with a dazed expression as I pumped his cock. I didn’t know what would come next. I was lost in the moment.

  Charles finally broke our kiss. I started to lie on my back as he leaned over me. As he stood over me, I reach out to hold his throbbing erection again. It was monstrously large compared to mine in both length and girth. I didn’t know he kept that in his pants when I struggled to hold mine down!

  I lovingly held my lover’s erection. I rubbed it across my face and lavished it with soft kisses. Charles groaned in approval as he caressed my face. I responded by taking the head of his cock in my mouth before pulling it out again. I rubbed the wet tip of his shaft against my face. I spread my legs wider as I enjoyed the sensations I felt. In the corner of my eye, I saw him place a hand on my thigh and trail it upwards.

  My body felt painfully stiff as if I were a wound up toy. His cock cried out to me and I indulged him by sucking its enormous length. Charles seemed to get bigger and bigger without showing any signs of coming anytime soon.

  After a few minutes of suckling, Charles let out a loud groan before placing his hands on my shoulders. He guided me onto the bed and moved in between my legs. I stared slack-jawed at his massive cock as my lover held its base with a hand. Placing it before my crotch, Charles spoke to me with a smile on his handsome face. “You seem so nervous, Tommy. What’s the matter?”

  I stuttered as pure terror flowed throughout my body. He was going to discover my secret. “I-I mean, it’s just that I’m-”

  “It looks this entrance is blocked,” he said with a devious smile. To my shock, he flipped me over onto my stomach. “Why don’t we take a detour, driver?”

  I looked over my shoulder to see Charles hi
king up my skirt. The man winked at me as if to tell me that I was in for a wild ride. Then, he pulled down my panties and exposed my ass. I was in too much of shock to tell whether or not he saw my balls. However, I did get a good view of Charles’s huge cock approaching my asshole.

  Charles prepared me by rubbing his shaft up and down the rosebud of my ass. My body shivered in arousal before I steadied myself. With one swift thrust, he entered me with a groan. I clenched my teeth and threw my head up. My mouth opened of its volition and let out a strained moan.

  My lover didn’t stop to let me rest. Instead, he entered me and only paused to give me time to adjust to his massive girth before venturing deeper. I was utterly shocked at my ability to take in his huge shaft. He was already so deep inside of me that I gasped when I saw that only half of his cock had penetrated me. My toes dug into the mattress as the tip of his cock probed me.

  I reached out to touch his sexy body. It wasn’t to stop him. Instead, I traced my fingertips across his muscular chest before reaching over to his hip. I placed my hands on his side and beckoned him to go further inside my ass. Charles did so with great enthusiasm.

  My lover grunted when he held onto my waist and thrust harder. I stared at the look of passion and determination of Charles’s face. I was nearing my climax from this acrobatic sexual encounter.

  I had forgotten that I was even a man. I was now Tommy, a sexual outlet for Charles. It was as if I were dreaming while fully aware I was awake. After taking him to the hilt, I beckoned him to make love to me. “Yes, that’s it… Oh!”

  Getting used to the feel of my ass around his cock, Charles closed his eyes and let out a growl of complete satisfaction. The hard look of concentration on his face and his soft words made my heart skip a beat. “Tommy… God you’re beautiful…”

  After stopping to gaze upon my sweat covered body for a moment, he went back to steadily thrusting in and out of me. Sometimes, he would almost completely exit out of me with his cock and prolong the sensation. Other times, he would immediately pump back into me.

  My hands grabbed fistfuls of the bed. I would rise off the bed in order to meet the impact of each thrust. I closed my eyes and focused more on the emotion of the encounter than the physical aspect of it. It was as if Tommy was taking over.

  Sandwiched between my body and the bed, my cock was unbearably hard. I was so damn close to coming. Likewise, Charles was on the same path from the sound of his groaning. He pumped into me like a man possessed. I echoed his feverish groaning as I arrived at the apex of my orgasm.

  Charles’s cock felt inhumanly long as he plundered the depths of my ass. My body grew rigid as my orgasm claimed me. His loud groans told me he was having one as well. My voice cracked as I cried and convulsed senselessly on the bed.

  Charles joined in on the fun with his twitching cock. “Tommy… I’m going to come!”

  The man began fucking me with complete abandon. He made long, deep plunges with so much power that he lifted my body off the bed. I watched in wide-eyed wonder as his throbbing shaft piston in and out of me like a machine. Charles gritted his teeth to keep him from grunting. However, passion broke his resolve as he let out a loud groan.

  He broke into a frenzied series of short thrusts. l dug my feet into the bed as he shot wave after wave of his hot come inside my ass. I sensed his cock jerk wildly inside of me like a machinegun firing upon enemies. I couldn’t help but cry out in ecstasy. “Oh… yes… fuck me! Ah!”

  I was caught between confusion and closure. I had never felt such raw passion given physical form. I had always been this shy driver masquerading as a woman. I never imagined I would ever act like such a sex kitten, especially with another man.

  Completely spent, Charles collapsed to my side. We were both exhausted. When my lover caught his breath, he finally spoke the shocking truth.

  “You might be a pro at cross-dressing,” he said to my complete surprise. “But I guess this is the first time you’ve done this. Not bad for a newcomer. Pun not intended!”

  I gasped in disbelief. “How long have you known?”

  “Since the moment I met you,” Charles revealed. “It was also the moment I knew I had to have you. After all, it was a damn good disguise you had.”

  I chuckled. “Not good enough. My name’s Tom by the way. It’s easy to remember.”

  He caressed my face. “But you’re pretty damn good in bed, Tom.”

  Gathering what little energy I had left, I rose and took him in for a passionate kiss. Seconds felt like days as our tired bodies locked lips. Only the fulfillment of our mutual desire caused out to break apart.

  I nuzzled my nose against Charles’s chest as he brought me closer to him. “I should get going. I work on commission after all.”

  Charles responded by embracing me from behind. I felt his wet yet still hard cock brush up against my buttocks. “Thanks for the ride, Tommy. How’s your schedule for tomorrow?”

  I smiled and laughed. “After tonight, I can give you a ride anytime you want!”

  There’s not much that can cheer you up from a messy divorce. There’s probably no other type of divorce. All of them are horrible and soul-crushing.

  In my case, I came home to the sight of my wife sleeping with the pool boy. What followed was a messy separation. Well, before that was a lot of yelling.

  Worse, Olga, my now ex-wife, had gotten more than her fair share from the divorce proceedings. It was like taking half of everything I had earned and giving it to my mortal enemy. Nonetheless, I was happy it was finally over.

  “It’s a fresh start,” my lawyer said, patting me on the shoulder. At least one of us was optimistic about my future. “It’s good that we got this done out of court. Juries and judges are always sympathetic to the wife.”

  I sighed. “It feels like I’m giving up, Tom.”

  “Believe me, you would be living in a courtroom for the better part of a year if you didn’t cut a deal with her,” he consoled. “There was no need to drag this out. You’d lose a hell of a lot more than this if your divorce went to court. You don’t have kids and it was a two-year marriage. Cutting bait is the best move you could’ve made.”

  Tom had been the voice of reason throughout the whole debacle. My lawyer convinced me to pull off the bandage quickly rather than fight Olga in the court for the next two years. Nonetheless, I felt like I had lost an arm and a leg from the whole ordeal.

  I should’ve seen it coming. The signs were there from the beginning. It was all downhill from the honeymoon. Olga and I kept fighting more and more as time went on. Over the past few months, she always had excuses not to see me. Her affair with the pool boy explained her long absences.

  As if it couldn’t get any worse, I left Tom’s office to the sight of heavy rain pouring from the darkened skies. The streets were soaked with rainwater. People raced around the city streets for shelter. It was practically a biblical flood.

  And I hadn’t packed an umbrella.

  I made due by placing my briefcase above my head. I didn’t care if the legal work got soaked. I had already been so mentally punched and spat upon that a little rain didn’t hurt.

  Despite my bravado, I had been heart-broken from the divorce. I had genuinely loved Olga even if she didn’t love me back. When I signed the divorce papers, it felt like I was erasing the past two years of my life.

  I felt directionless as I walked the rain-soaked streets. I had bought a new apartment after initiating the divorce process. Olga didn’t win the old house but I decided to sell it anyway. The place had too many bad memories. However, I wasn’t too eager to head to my apartment just yet. It was hard coming home to a barely furnished apartment.

  At least I had Amy’s Café. It was a nearby coffee shop that I had fallen in love with. I could grab a nice cup of coffee and a freshly baked croissant on the way to meeting my divorce lawyer. I loved nothing more than sipping a nice cup of freshly brewed coffee while reading a book. I couldn’t wait to bury my head into a new book and f
orget my problems at my favorite café.

  Or so I thought.

  Amy’s Café was jam-packed with people. Some wanted to escape the rain. Others were regulars on their break from work. Regardless, it didn’t seem like I could get a seat at the café.

  “I’m sorry, sir,” the barista said. “We’re almost at full capacity. There aren’t any tables available at the moment. Maybe you’d like to take something to go?”

  I sighed and glanced at the line at the counter. It looked like a breadline straight out of the great depression. It would take an hour for me to place my order. “I don’t think I’ll be able to get a cup of coffee within my lifetime…”

  That’s when a nearby waitress chipped in. “Actually, we do have a table available. We’re just giving groups priority to groups and couples.”