The Trans Ultra Collection Vol 3

by Ursula Lovelace

  I was thankful I had a light breakfast because my stomach churn. I wanted to turn tail and run but Claire had cornered me. I didn’t know what she had planned for me but I didn’t like the sight of butt plugs and a strap-on dildo. However, I knew retreat was not an option.

  I could lose everything by refusing Claire. She could get me benched from the team. The playoffs were fast approaching and I needed to be there for the team. Furthermore, she was offering to put in a good word for me with her relatives at the NHL. I wasn’t sure if I trusted her but it wasn’t like I had a choice. “I’ll do it…”

  Claire smiled. “Good girl!”

  I nearly did a double take at that. “Good girl?”

  She slapped the riding crop gently against her hand. “Now that you’ve agreed to my terms, you’ll have to address me as ‘Mistress’ for the duration of this session.”

  Claire punctuated her statement by tapping her palm hard with the riding crop. That sent a shiver down my spine. “Yes Mistress!”

  I knew this weird arrangement couldn’t go on forever and forever. Whatever Claire had planned for me would have to end before the rest of the college staff and students started streaming into the ice rink. I’d just have to endure what she had planned for a couple of hours.

  “There will be a punishment for upsetting me,” Claire threatened. “Don’t act naughty or else I’ll have to do this the hard way!”

  I repressed a shudder. “Yes, Mistress.”

  “Now, young lady,” she said, causing me to get confused. “A novice ladies figure skater like yourself can’t go around calling yourself Jeremy. You need a softer sounding name.”

  The woman was talking to me as if I shared her gender. “What?”

  “I know,” Claire said, snapping her fingers. “Jenna sounds perfect for an aspiring figure skater. Yes, that will do nicely. How’s that sound?”

  I was too shell-shocked to argue the point. “It’s good…”

  “I knew you would like it,” she said, before pointing to my clothes. “Now that letterman jacket don’t do for my little ice princess. I’ll need you to take off your clothes.”

  I gasped. “What?”

  “Do it or else I will punish you,” Claire said firmly, tapping the riding crop against her hand. “And you’ll have to explain to Coach Smith why you were so difficult to work with.”

  That lit a fire under my ass. I raced to take off my clothes. I stopped at my boxers until Claire tapped that damn crop against her hand again. Finally, I took off my boxers and covered my groin with my hands.

  I shook from head to toe. Normally, I felt right at home in an ice rink. Now, I was shivering with no protection from the elements. The freezing air bit into my naked skin. My toes were feeling the full blast of the cold floor. I desperately wanted my hockey gear.

  My nudity was compounded with the smug look on Claire’s face. She had all the power here. I may have been a hotshot hockey player but I felt like defenseless baby before her.

  “Chilly?” she teased. I immediately nodded as she laid out the clothing she had pulled from the bag. “I think a nice figure skating outfit will help you appreciate the finer points of this sport.”

  I was desperate for warmth. “I’ll take anything!”

  Claire giggled as she held up girlish figure skating outfit. “That’s the spirit!”

  Chapter 4

  With the cold air nipping at my exposed skin, I was anxious to wear anything. It wasn’t about modesty anymore. I wanted to cover myself up and be warm. It didn’t help when Claire separated my hands from my crotch.

  My erection felt trapped between two directions. I was turned on by Claire’s sexy outfit. However, it was cold as a blizzard in here.

  I blushed when she said. “It’s time we covered you up before your balls freeze off. Here, put on some bra and panties.”

  Claire held out a pair of dainty panties. They weren’t particularly thick but I just wanted something to wear. Nonetheless, there was something appealing about the silky fabric. I quickly put them on and felt it ride up my ass. It had a different feel to it than wearing a pair of boxers or briefs.

  I wanted more clothing and Claire was happy to provide me with some. She used her riding crop to deliver a bra to me. It was simultaneously a nice gesture and a threat.

  The bra was just as high quality as the panties. There was an embroidered floral pattern on the bra. I looked inside and I saw that Claire had padded out the cups. I knew it would give me a bust line when I put it on.

  However, just hooking it on was a challenge. I could take a bra off with ease but the opposite was trickier. I just couldn’t get the straps hooked together. Claire had to step in behind me and help me put it on.

  She rewarded me for my lack of skill by striking me on the shoulder with her riding crop. “Ow!”

  “Silly girl can’t even put on a bra!” Claire teased. “I’ll teach you the finer points of being a girl.”

  Rubbing the spot where she hit me, I found the bra to be rather comfortable. The interior padding cushioned the cups against my bare skin. I didn’t have much time to relax because Claire handed me more undergarments.

  I put on a pair of tight stockings with a garter belt. Once again, Claire had to come in and help me since I didn’t have a clue what to do. Thankfully, she didn’t threaten to hit me again. I found the tightness of the stockings to be rather pleasing. It didn’t impede my movements either.

  It was strange being transformed from an alpha male athlete into a graceful ice princess. Each piece of clothing was another step in the process. The figure skating dress completed the look. It was a loose, pink-colored dress that was soft to the touch. The skirt portion of its flowed with the faintest breeze.

  I gasped when I caught my reflection on the screen of a blank television. I looked like a woman. I had always prided myself on being a tall, athletic man. Yet, a simple wardrobe changed had turned me into someone else.

  If there was one piece of the outfit that belonged to me, then it were my skates. The pair had been with me for the better part of a year. I had even gotten them sharpened yesterday. Despite their dark color, they looked decidedly girly with the rest of my look. Hell, it even felt different to walk around in them with a dress on.

  Claire nodded in approval of my new look. “It’s starting to come together, Jenna. Now, let’s doll you up for the judges.”

  She was making it sound like I had to perform a figure skating routine. I didn’t know anything about the sport. I was the guy you hired if you needed a slap shot with pinpoint accuracy.

  “Pucker up,” she commanded. The figure skater stuck out her bee-stung lips. “Like me.”

  I tried to do my best to mimic her. Unfortunately, my best wasn’t good enough and she struck me with the riding crop. “Ow!”

  “Do it like you mean it!”

  “Yes, Mistress!”

  She touched my lower lip with a finger. “Good, now stand still.”

  Satisfied, Claire retrieved the makeup kit from earlier. I saw lipstick, mascara, and a bunch of other stuff that I couldn’t identify. Hey, I didn’t go around wearing makeup all day. I couldn’t tell the difference between lip gloss and eyeliner.

  Thankfully, my Mistress was an expert when it came to women’s fashion. With casual ease, she applied the various bottles of makeup to my face. She started with some blush and foundation before working her way up to lipstick. I had shaved in the morning so there weren’t any obstacles for the makeup.

  I tried to wait patiently while dying to know how I looked. Claire took her time with my eyes. She used everything from eye shadow to mascara. I felt like a movie star being transformed to play a new role.

  The clothes and makeup seemed to mitigate my naturally masculine looks. I started to think less and less of myself as a jock. By now, Claire had shattered my manly pride into a thousand pieces. This figure skating outfit just added insult to injury.

  Next came the wig. The brown hair looked like the real thing.
Maybe it was made out of actual human hair. In any case, Claire began fixing it to my head.

  After she finished applying the wig, Claire took out a hand mirror. I gasped out loud in disbelief. “Oh my God!”

  “Looking sharp, Jenna,” Claire said, proud of her handiwork. “Now, it’s time to start your training.”

  I didn’t like the sound of that.

  In fact, I didn’t like where this was going. Claire had made me dress up as a female figure skater. She was hitting me with a crop for the slightest mistake. I didn’t want things to escalate any further.

  However, I couldn’t run for the hills either. I wasn’t sure how I could explain to Coach Smith about what Claire was doing. Besides, he was likely to side with her over me. She seemed to be a celebrity due to her achievements as a figure skater. Even as a star hockey player, I was still a small fry trying to make it to the NHL.

  I also couldn’t waltz out of here wearing a dress and a wig. I looked like a complete weirdo. No one would be able to take my claims seriously if I came out looking like a cross-dresser. I had no choice but to go along with Claire’s scheme.

  “OW!”

  I felt a sting of pain across my arm.

  “Pay attention,” Claire chastised, flicking the riding crop with a finger. “As I was saying, I need you to be the epitome of feminine grace. That means you’ll have to act like a girl, Jenna.”

  I didn’t bother rubbing my arm. “Yes, Mistress.”

  “Say it again,” she commanded. “But in a softer, more girlish voice.”

  It was a strange request. However, I wasn’t eager to get hit again. That riding crop stung like a bitch. “Yes, Mistress.”

  Claire gave a sinister smile. “That’s much better, Jenna. Now, I want you to lean over the side of rink. I’ve got a special surprise for you.”

  “Yes, Mistress.”

  The blades of my skates made a clacking sound as I walked to the outside edge of the rink. I heard Claire walking lockstep with me. When I reached the rink, I leaned over it so the upper half of my torso was over the barrier.

  Suddenly, Claire stepped behind me and lifted up my skirt. I felt the cool air of the arena against my panty-clad buttocks. “Now let’s prepare my little skater for her medal winning routine.”

  Then, she took down my panties and exposed my ass. I felt her fingertips begin to rub the rosebud of my ass. It was some sort of clear gel. It was the kind I used to lube up for…

  My heart skipped a beat when I realized what she was doing.

  The woman wanted to stick something up my ass. I wasn’t as keen on the idea. That part of me was a one way street.

  My suspicions were confirmed when I saw her retrieve the butt plugs she had pulled out of her bag. The plugs were each larger than the last one. Even the smallest one seemed pretty daunting. For that matter, Claire still had the massive dildo. I didn’t know how that thing would even fit inside of me.

  I knew the figure skater planned on fucking me with that dildo. She had a harness that could turn it onto a strap-on. However, she would have a hard time even getting the tip of it inside my asshole.

  That’s where the butt plugs came in.

  Literally.

  Claire slid a butt plug inside my ass. The lubrication from earlier helped reduce the friction. She slid it in and out so I could get used to the size of the plug. Once the figure skater was satisfied, she buried it deep inside of my ass. I felt my butt cheeks converge on it and keep it firmly entrenched inside of me.

  Then, I felt the figure skater pull up panties back up and covered the butt plug. The slightest movement caused the plug to gyrate inside of me. It sent a pulse of pleasure throughout my body. I had never experienced anything like this before.

  My erection poked up against the gusset of my panties. Something about being turned into a woman and humiliated was turning me on. I couldn’t recall the last time I had been this hard. I prayed that I could keep my prick in my pants.

  Well, panties to be more precise.

  Claire stroked her chin. “Why don’t you try walking around in it, Jenna?”

  I did as commanded and walked up and down the side of the rink. The plug definitely affected my posture. While I was no stranger to walking off ice in skates, I took it slow and steady. Soon, the pain became numb to me. I barely felt that there was anything inside of me.

  With a smile, my Mistress commanded me. “Good, now get on the ice. It’s time for the real training.”

  Chapter 5

  I had done laps around the rink as far back as I could remember. I did them as a kid when I first started playing hockey. I continued doing heavy skating drills under Coach Smith.

  Skating in a girly dress with a butt plug all the way up my ass was something new.

  Struggling to even breathe, I skated cautiously around the circumference of the rink. That damn plug was throwing me off balance. I couldn’t motor through the ice like I usually did. I had carefully stroke using the tips I had learned from Claire. Nonetheless, the figure skater wasn’t completely happy with my technique.

  “You’re slower than a junior figure skater,” she said, striking my back with her riding crop. I felt like a damn horse with the way she kept hitting me. “Pick up the pace. Use the edge of the blade like I taught you!”

  The plug inside of me had actually become a bit comfortable. Skating with it inside of me had allowed me to loosen up a bit. It allowed me to focus more on my speed and balance.

  Soon, I was skating faster than I had ever done before. Sure, I didn’t have heavy hockey gear on but I had still struggled to catch Claire while wearing regular clothes. Now, I was starting to put a bit of distance between us. All the stuff she had tried to teach me was finally coming together.

  Well, it wasn’t the only thing about to come.

  My cock was harder than the blade of my skate. It felt like I had my own personal hockey stick between my legs. The tightness in my panties was the most difficult part about skating. I needed to come hard and fast. However, Claire wouldn’t let me stop for even a second.

  Around and around, we raced across the edge of the ice rink. I sailed across the ice as if I had a rocket strapped to my back. All of my strokes had a steady rhythm to them. I didn’t try to muscle my way like I used to do. Even Claire had to get into top gear in order to keep up with me. Perhaps, this was her plan after all.

  Eventually, I reached my limit and nearly collapsed onto the ice. My legs were burning and my feet could’ve used a good foot massage. Claire giggled when she saw how worn down I was. “Jenna, are feeling a little burnt out?”

  In comparison, she didn’t look the slightest bit tired from the countless laps we had just finished. I guessed that was the difference between an Olympic figure skater and a hockey jock like me. “Yes I am, Mistress.”

  “I think it’s time we moved onto a new exercise,” Claire said with glee. I saw her head off the ice and retrieve the dildo from earlier. “I hope that butt plug has made you all nice and loose for this baby.”

  I gulped when I saw her attach it to the harness and transform it into a huge strap-on. That monstrosity looked like belonged to a horse. It hung low from her crotch and swung as she walked towards me.

  I was starting to get second thoughts about this arrangement. I may have agreed to dressing up as a figure skater and doing some humiliating exercises but this whole new level of depravity. Claire intended to fuck my ass with that thing. I could tell she was just as good using a strap-on as she was with her figure skates.

  However, Claire read the look on her face. “Is this too much, Jenna? You can always leave. Of course, I’ll have to tell your coach how naughty you’ve been. You’ll have to sit out the whole season!”

  She tapped the rink’s barrier with her riding crop for good measure.

  I repressed a shudder. “No, I’ll stay, Mistress.”

  I didn’t look forward to get fucked up the ass. However, I couldn’t risk upsetting Claire and getting benched from the team.
I also needed her to put in a good word for me with her family. There was too much at stake to back down now.

  “Good, now bend over the barrier,” she commanded, getting back on the ice. That damn dildo looked like a battering ram from medieval warfare. It was a long, purple-colored spire that waggled between her legs. A butt plug was one thing but that dildo made me tremble. “It’ll be easier if you don’t resist.”