The Trans Ultra Collection Vol 2

by Ursula Lovelace

  The director patted me on the back as I got off the bed. “Believe me, I’ve worked with guys who could barely remember their lines. You’re practically Marlon Brando in a work like this.”

  “You did great, Jake,” June added, placing the paddle on the dresser. “You’re a real natural at wearing a dress!”

  Indeed, the soft fabric of my dress was to die for. Andy didn’t skimp out on making sure the company’s wardrobe was stocked with high quality clothing. I wouldn’t mind taking some of it home.

  “Rest up, Jake,” the director said, shutting down the set. “Tomorrow is the big day!”

  By that, he meant the sex scene.

  It wasn’t like I was a virgin. No, I was just new to being pegged by a woman. I’d have to do it on camera no less.

  I had jumped out windows before for a movie but having sex on film was a whole different ballgame. It was strange being a porn performer instead of a stunt performer. I was front and center of the stage. I didn’t have to wait to do my part.

  It did come with its perks. Other than the steady paycheck, Andy made sure I was always comfortable on set. I got frequent breaks and free lunch. I never got the star treatment for getting set on fire for a stunt.

  While the actresses on set could act mean for a scene, they were sweet when the cameras turned off. I didn’t work with Mandy and Sarah but I did have lunch with them. I generally spent more time with Mistress June for work.

  The two of us were heading up a new production. With Frank out of commission, I was the new lead to ‘School Daze 9.’ It was a long running series where a young guy would dress up as a school girl. He usually ended up getting caught and punished. I was the guy in question and June was the roommate I stole my clothes from.

  There were also a number of other male performers. Unlike me, these guys were real pros. I didn’t see them much during filming but they seemed nice enough during our coffee break. I got on better with them than most of the actors I met on mainstream films.

  Frolic Pictures tended to have a handful of actors on staff and hire the rest on a contract basis. They must have been desperate to hire a guy like me on such short notice. Not that I was complaining.

  In fact, wearing a girlish dress and makeup was easier than I had ever imagined. The frilly clothes fit me like a glove and the makeup crew knew how to doll me up perfectly. That said, I wasn’t quite ready to have my first real sex scene on camera.

  “First time, jitters?”

  I turned to see June with a teasing smile. I didn’t bother to lie to her. “This is my first sex scene on camera. What the hell am I supposed to do?”

  She giggled. “Relax, I’m a professional at this. I’ve fucked more guys with a strap-on than I can remember.”

  I sighed. “That’s supposed to help me relax?”

  I wasn’t just doing this for the money. I was mainly doing it to be with June. On and off stage, the woman was beautiful and charismatic. Still, I wasn’t so keen on the idea of being pegged by her.

  “The whole thing is simple,” she continued. “You’re already on the enema treatment. We’ll also have you do a few exercises with a plug to warm you up. Believe me, you’ll barely feel it go in once we’ve prepped you.”

  I wasn’t as convinced. “If you say so…”

  She sensed my hesitation. “Just follow my lead, Jake. Once you get used to pegging, you can literally do it blindfolded. In fact, I’m certain you’ll love it.”

  “Love it?”

  “It doesn’t make you weird for liking it,” June said with a laugh. “I’ve fucked plenty of straight guys with a dildo and they loved it. Some of them even had girlfriends. They even tried pegging with them!”

  I felt my body seize up at the thought. “Is there anything else we can do to prepare?”

  June took out her car keys. “There’s only one way to prepare. Let’s practice.”

  An hour later, I was in June’s bedroom with lube dripping out of my ass. When the woman finished preparing me, she put on a strap-on dildo. It was the smallest in her impressive personal collection. Nonetheless, it was quite imposing for a beginner like me.

  With my ass thoroughly lubed up, June positioned herself behind me as I got on all fours. “Don’t inhale, Jake. Exhale since the air is going to be knocked out of you.”

  I took her advice and exhaled. In the next moment, I felt the small dildo enter me through my rosebud. A silent gasp escaped my lips as it further penetrated me.

  She stopped thrusting in and said. “Good, get used to its girth.”

  I was thankful for the fact that she had slicked my ass with lube. Otherwise, I would’ve been in a world of pain. As it was, her dildo stretched my asshole without bruising it. Soon, I felt pleasure ripple through my body from the point of impact.

  June steadily thrust into my ass. The woman was no novice as this. She knew just the right speed and pressure to enter me with.

  I had never gotten so hard before in my life. My cock was ready to go off and I had barely touched it. I never thought of myself as into kinky sex. Yet, having June peg me from behind was natural as breathing. It felt so naughty and all the more right for it.

  I was happy that we were in the privacy of her apartment bedroom. Otherwise, my voice could reverberate all over the place. June grunted with me but her cries were controlled. This wasn’t her first time deflowering an anal virgin like me. She had fucked plenty of men on and off camera.

  I was thankful for the fact that I had such an experienced teacher. Otherwise, I would barely be able to process what was happening. June’s thrusts were steady and slow. Each movement shook my body with calculated pressure.

  I drooled senselessly onto the floor as she fucked me. I wasn’t sure how I could keep going on. Indeed, my cock felt like it would erupt at any moment. “June, I’m going to cum…AH!”

  She continued to drill the dildo into me as I came. “Cum for me…”

  My cock sputtered its load onto a handy towel below me. June and I trembled together from the force of my explosive release. Her thrusting movements stopped as she held onto me.

  Down below, I came like a firehose. I drenched June’s towel with my sticky cargo. Whenever I felt like I was finished, I immediately followed up with another load. When it finally let up, I reached down to stroke my cock and drain it of its last few drops.

  I couldn’t believe the erotic rush I was feeling. I had done countless death defying stunts in my life. I had braved fire and a dozen other hazards for the sake of moviemaking. None of them gave me the same high as getting pegged in the ass by a woman.

  Satisfied, June withdrew the dildo and took off her strap-on. “Did you like it?”

  I blushed. “I loved it.”

  Afterwards, she plugged my ass with medium sized butt plug. Although I was sore, I was loose enough to be fitted. June told me this was a warm-up for the real deal tomorrow. She would use a regular size strap-on dildo on me for the filming. The one she used on me wouldn’t do it when making porn for the big leagues.

  “Think of this as a dress rehearsal for the real deal,” June said, pulling out a much bigger dildo than the one. I watched her shake it in her hand. “Don’t let it intimidate you. You’re more than ready for it.”

  Sore yet happy, I left her apartment to prepare for the filming tomorrow. There was no going back after that. I would be a full-fledged porn star. At least it paid better than being a stuntman.

  For better or for worse, there was never a dull day on set.

  “Okay Jake, this is the big one,” the director told me with glee. You would think he was making an epic Hollywood film instead of a fetish porno. “June is going to help you get in better touch with your feminine side. She’ll start calling you Jenny.”

  I nodded along and rolled with the wacky script. “Right, I’m Jenny.”

  June pulled out the school girl outfit I was supposed to wear. “You’ll look lovely in it, Jake.”

  I still had some nerves but Andy came and slapped
me on the back. “How is my new star doing?”

  I flashed a smile at my new boss. “I’m adjusting.”

  Andy took me to the side for a moment. Then, he opened up a cooler full of liquor. “Good, I’m glad we got this production back on track. You don’t know how much trouble you’re saving me. Here, have a drink?”

  I chuckled before taking a small glass of bourbon from him. “You sure I should drink before a scene?”

  “Drinking on set is part of the job requirement,” he laughed, pouring himself some whiskey with some ice cubes. “It steadies your nerves.”

  I took a swig of the bourbon. “Strong stuff.”

  “You’ll have a bit of a hangover after work,” he replied. “But you’ll be happy to have a little liquid courage to strengthen you up. Trust me, you need all the help you can get with Mistress June!”

  Andy left me alone to prepare for the filming. While the alcohol helped, I was more motivated by the presence of June. Our earlier pegging session had been a wonderful experience. I couldn’t believe how much I liked having it up the ass. I could believe how much I loved having a gorgeous woman fuck me.

  Nevertheless, I had to get dressed for the scene. By now, I was an expert at putting on women’s clothes. I could put on stockings and hook them with a garter belt with my eyes closed. The rest of the outfit was just as easy. It was comprised of a tight blouse, a miniskirt, and a pair of dainty heels.

  The only help I needed was with putting on makeup. Thankfully, Frolic Pictures had some of the best makeup artists in town. Within ten minutes, they had practically transformed me from a red-blooded man to someone who could pass for the fairer sex. It was a much better experience than getting coated with flame proof jelly before a fire stunt.

  A pair of women twirled me around in a chair and applied makeup on me. They were old pros at this. Unlike me, their hands didn’t tremble when applying mascara.

  I was stunned at the face I saw in the mirror. Between my wig and makeup, I barely recognized myself. My appearance was softer and more inviting. While the wig did much of the work, the blush helped bring out my cheekbones.

  I was envious of the studio’s wardrobe. Most productions I had been on never had the need for such extensive assortments of outfits, dresses, and costumes. Frolic Pictures, however, was productive enough to require a multitude of clothing, wigs, and heels.

  It was like some sort of candy store for fetish wear. They had everything you would ever want in every material and color. I saw wigs of every shade, including green and blue.

  I looked at some of the dominatrix gear. It was all black leather with studs and belts. It stood in sharp contrast with my colorful outfit. My dress was somewhat modest while being tight enough to accentuate my curves. I had kept in pretty good shape for my work as a stuntman. The stockings were a comfortable fit against my toned calves. The fashionable pair of heels I wore bumped up my height. I was almost as tall as June.

  The dress I wore made me look like the girl next door. I had never been much of a hairy guy to begin with but I had taken care to groom my body hair. My body was as smooth as that of a supermodel. It helped that the company paid for my spa treatments.

  My favorite part was the lingerie. I loved having a silky thong rest up against my groin. In comparison, it made my boxers feel like a potato sack. A stuffed bra completed the look and filled out my blouse. The whole set fit snuggly against my bare skin.

  When I looked in the mirror, I didn’t see a washed up stuntman. Instead, I saw a sexy yet delicate girl with star power. She wasn’t some throwaway extra in a movie. This young woman was the centerpiece of the whole event.

  Chapter 5

  As I finished dressing, I heard someone approach me from behind. It was June with a half-smile on her face. “Any first time, jitters?”

  She wore a dark leather outfit that highlighted her sexy body. The leather shone under the bright set lighting. It made it seem like there was a constant spotlight on her.

  “Not when this isn’t my first time,” I replied. She had done a number on my ass the other day. Now, I was properly loosened up for the main event. “I’m ready as I can ever be.”

  Her expression softened for a moment. “It’s nice talking to you, Jake.”

  “It’s nice getting talked to,” I replied. That got a giggle out of her. “You must be friends with a lot of people in this industry. I’m pretty boring in comparison.”

  She shook her head. “Most men tend to get weird about me being a dominatrix, even if they are also performers. It’s why I like to keep my professional life separate from my personal life.”

  “Seriously?” I asked rhetorically. “How long have you, well, been in the business?”

  “Five years,” she answered. “For much of my life, I wanted to be in control without realizing it. I experimented a bit in college and got drawn into the scene. I did this as a job in order to improve my skills. What better way to become a dominatrix than to do it for a living?”

  It made me think about how much I enjoyed cross-dressing. For much of my life, I was like every other testosterone driven man. For my work as a stuntman, it was a requirement. I needed to get in touch with my manly, aggressive side to do stunt work.

  Now, I was seeing a part of myself I never knew had ever existed. I loved my new clothes and hated the fact I would have to hand them in after the filming finished. With my new paycheck, I could buy my own wardrobe and get in touch with my softer side. I knew how I was going to treat myself after work.

  June helped tie a small necklace behind my neck. Her fingertips were cool against my hot skin as she clasped the hook. As good as the money was, I did this to be with her.

  “If you have second thoughts, you can back off, Jake,” she replied. “This type of work isn’t for everyone. Andy cycles through a lot of actors, especially for roles like these. There won’t be any hard feelings if you want to drop out.”

  Even if I wanted to, it felt wrong to turn tail and run. Everyone was counting on me to perform. Andy had really stuck his neck out for me by giving me a steady paycheck. I chuckled at the thought of running away. “After a training session like that, this is a cakewalk.”

  “People say that we’re not real actors,” June said with a half-smile. Her words were completely sincere. “But we put a lot of our blood, sweat, and tears into this craft.”

  “Sometimes, a little too literally.”

  She giggled. “Yes, sometimes we do that. Let’s get this show on the road.”

  Taking my arm, June led me to the filming set. It was a large bedroom that stood for June’s room. With my dress and wig, I felt just as home in it.

  The director wolf whistled at me. “Well, if it isn’t the belle of the ball! How are you feeling, Jake? Or should I say Jenny?”

  I laughed. “I’m getting used to it.”

  In fact, whole crew was staring at me in awe. I wasn’t used to being the center of attention. Stuntmen were a dime a dozen on set. Now, all eyes were glued to me. Some of the men were slack-jawed at me.

  Andy looked at me with pride. “There’s my new girl! Now, let’s get to work.”

  The director went over the basics of the scene. “Good, you’re here. We’ve all read the script.”

  I nodded. “This is where I start turning into Jenny.”

  “We’ll get to have so much fun!” June chimed in. She toyed with a strap-on dildo with her hand. “You’ll be in very good hands.”

  I took a deep breath. “Let’s get started.”

  Within minutes, I was on a bed in front of June. I looked as girlish and dainty as I could possibly be. I kept my hand on my lap like a proper lady.

  On the other hand, ‘Mistress June’ looked like a bona fide seductress. She still had her dominatrix getup. Her leather thong fit snuggly against her sexy body. A large strap-on dildo protruded from her groin.

  She reached out to touch my lips with a fingertip. “Open wide, Jenny. Those plump little lips of yours are getting a workout ton
ight.”

  I started down at the strap-on harness between her legs. The dildo was utterly massive compared to the one she had fucked me earlier with. “Yes, Mistress.”

  “Good girl,” she said coldly. I was lost in my performance. I didn’t give as much as a glance at the camera. Nothing beat method acting when it came to this. “Are you read for me to fuck every little hole in your body?”

  I watched as she stroked the dildo between her legs. “Yes, Mistress.”

  “You want this cock, don’t you?” she teased, placing a hand on the base of her dildo. “Beg for my cock, Jenny.”

  I didn’t skip a beat. “I want to suck your cock!”