The Trans Ultra Collection Vol 2

by Ursula Lovelace

  Compared to getting hit for the smallest mistake, I actually enjoyed having my ‘Madam’ apply makeup to my face. I had shaved earlier in the day since we had a small photoshoot during practice. Ms. McKay was able to apply makeup on face with ease. She used everything from foundation to eye shadow.

  While I couldn’t see myself, I knew I was changing. It wasn’t just my face. My entire body felt less like that of a quarterback and more like that of a dainty schoolgirl. The girlish clothes I had on sealed the deal.

  After she finished putting on lipstick, Ms. McKay pulled out a mirror. I had to admit I looked like a knockout. The rich redness of my lipstick went well with my dark mascara. “You look pretty, Tara.”

  I almost wanted to blush. “Thank you, Madam.”

  “Try not to smear your makeup,” she said harshly. This was beginning to sound less like a science experiment and more like blackmail. I didn’t know whether or not I wanted to walk, act, and look like a girl. I did know that I didn’t want to get on Ms. McKay’s bad side. “I can be very demanding.”

  I thought about making a beeline to the door and escaping. I could tell the faculty or the police what Ms. McKay was up to. However, I wasn’t sure anyone would buy my accusation. She might have been young but she was still a respected member of the teaching staff. They would think I was just some dumb jock who was angry about a failing grade. To top it all off, she could fail me and get me kicked off the team.

  Besides, I wasn’t eager to reveal to anyone that my professor had made me dress up like a schoolgirl and hit me with a riding crop. I was going to have to see this to the end. Unfortunately, I wasn’t sure where I was going to end up.

  My ‘Madam’ continued her warpath by taking out a wig. I wasn’t an expert on fake hair but it looked like it was made of real hair. When she secured it over my head, it looked completely natural.

  Ms. McKay surveyed her handiwork and smiled. “I’ll have to admit, I’ve really out done myself. Well, enough of this. It’s time to begin the experiment.”

  I murmured in confusion. “Begin?”

  THACK!

  I got another mark on my hand for that.

  “Only speak when spoken to,” she growled, twirling the riding crop in her hand. “This is a behavioral science experiment. I’ll need you to behave like a girl. Is that understood?”

  “Yes, Madam.”

  She glared at me. “Speak to me with a girl’s voice.”

  That was strange but I wasn’t exactly in a position to argue. I raised my voice by an octave. “Yes, Madam.”

  She shook her head. “Higher.”

  I barely stopped my voice from cracking. “Yes, Madam.”

  Ms. McKay smiled. “Good. Now, get up and bend over the table.”

  I didn’t hesitate to do so. As I walked towards the conference table, I heard her follow me. When I bent over, my short skirt rose up and exposed a bit of my panties.

  My professor wasn’t satisfied with the view so she hiked up my skirt before pulling down my panties. “That’s better. Now, let’s continue the experiment.”

  WHACK!

  The woman spanked my ass with the flat of her hand. It hurt a bit but it was better than getting hit by her damn crop. Again and again, she struck me “Ah! Ah! AH!”

  “Tell me you love it, Tara!”

  “I love it!”

  She spanked me again. “Say it again!”

  “I love being spanked.”

  “Say that you’ve been a naughty girl!”

  I practically chanted. “I’ve been a naughty girl.”

  Ms. McKay stopped to examine her handiwork. I guessed my ass cheeks were as red as a radish. I shuddered when she touched my bruises with her fingertips. “Good, you’re ready for the next step.”

  That’s when I felt something cool and wet touch the rosebud of my ass. I turned to watch her apply a gel at my rear entrance. I instantly knew it was a form of lubrication.

  That could mean one thing.

  I glanced at the large dildo in the case. There was no way that thing could fit in me. I wasn’t even sure so could get even an inch inside of me. Worse, that thing was a strap-on. She would have to wear it in order to use it on me.

  Ms. McKay shared my doubts because she used a butt plug to loosen me up. I grunted as the plug slid across my tight orifice. The woman slowly thrust it in and out of me. With each movement, she went deeper and deeper inside of me. With time, my ass adjusted to the intrusion. When she stopped, my rosebud kept it embedded in my ass.

  I watched as my professor pulled up my panties and brought down my beaten ass. Then, she ordered me. “Sit back down… with that plug still inside of you, Tara.”

  When I hesitated, she brought her crop down hard on the table. I knew a threat when I saw one. I immediately found a chair and sat down.

  It was strange.

  It felt like the slightest motion would force that damn plug to travel up and down. It was touching every nook and cranny of my ass. Weirder still was the fact that I was enjoying it.

  My cock was getting harder than it had ever been before. Nothing had ever managed to turn me on like this. I was actually finding pleasure in the humiliation of being forced to dress up like a girl and have a plug shoved up my ass. My erection fought to escape my panties.

  Ms. McKay didn’t show any signs of stopping. “Now, get up and march around the table.”

  I was no stranger to marching drills. I did them weekly with the rest of my team. In my spare time, I would even hit the track for a few laps.

  Marching in high heels with a butt plug was something else.

  Cursing under my breath, I began a steady jog around the edge of the table. It was easier said than done. Heels weren’t meant for much beyond a model’s strut. I felt like I could fall at a moment’s notice. Only the threat of Ms. McKay’s riding crop prevented me from stopping.

  “Faster,” she growled, smacking my ass with the crop. There was a wide smile on her face as she struck me. “No slacking off, Tara!”

  With each step, the butt plug moved around my ass. I felt I had loosened up and could accommodate a larger plug. I guessed that was my professor’s strategy to begin with.

  The more I jogged, the harder I got. I had never had such a stiff and painful erection before. My panties felt more and more like a straightjacket. I felt wound up like a spring that needed to be released. All the sexual tension in my body needed a place to go.

  Finally, I reached my limit. My feet couldn’t stand the pace and I tripped over in my heels. Wallowing on the floor, I gather my breath as Ms. McKay teased me. “Is my little girly-girl tired?”

  Despite how exhausted I was, I knew better than to ask for a break. This was only the first step in this strange experiment. “No, Madam.”

  “Good, you’re ready for the next phase.”

  My heart skipped a beat when I saw her walk towards the large strap-on in the case. That thing was longer and thicker than Ms. McKay’s forearm. I shuddered when I saw her casually tie the straps around her waist. From the way she moved with that thing, I knew she wasn’t an amateur.

  She lovingly ran a finger across the length of the dildo like it was a pet. “I’ve been dying to use this. Why don’t you get on all fours and give it a nice kiss, Tara?”

  I may have agreed to be the subject of humiliation but this was something else. My professor planned on making me a kiss a strap-on dildo. I knew she planned on fucking me with it soon after. As crazy as this experiment had been so far, this prospect made me eye the door.

  THWACK!

  I rubbed my arm as Ms. McKay withdrew the crop. “I said get on all fours!”

  I took a deep breath and thought about my options. I just needed to get through to this session and I would be home free. I wouldn’t have to worry about getting kicked off the team. I could go on and play in the NFL.

  On the other hand, my professor would fuck my ass raw with a dildo!

  With another gulp of air, I got on my knees and stare
d point black at the strap-on. It looked like a sword pointed straight at me. This monolith was thicker and lengthier than my cock. It could barely fit in my mouth. I shuddered to think how she would get it inside my ass.

  Taking the initiative, Ms. McKay thrust forward and brought her dildo to my lips. I saw my lipstick tinge its tip with a bright red color. She pushed forward and I found the large phallus in between my gums.

  Slowly, Ms. McKay entered deeper into my mouth. “You’re going to suck this cock like your life depends on it.”

  If felt like it really did. I needed to endure this so I could go on and stay on the team. My NFL career was at stake. Swallowing my pride, I began to swallow her dildo as well.

  Closing my eyes, I took more and more of her fake cock into my mouth. The dildo was made of some soft plastic with a little give. It almost felt like the real thing.

  My professor fucked my mouth with the strap-on. Each time she withdrew, I gasped for air. She enjoyed watching me struggle. “Yes, suck it down like the naughty little bitch you are.”

  I grasped the base of her shaft and went to town on it with my mouth. My tongue ran a trail across the underbelly of the dildo. I gyrated my head and ground the phallus against Ms. McKay’s pussy.

  Ms. McKay enjoyed what I was doing and rewarded me with a moan. A part of me actually felt happy to make her feel like this. I watched as she ground her pelvis against the strap-on. I took in more and more of her false cock. In fact, I was actually beginning to enjoy being humiliated like this.

  I sucked her harder and faster with each passing second. Down below, my cock engorged to a larger size. Its head rasped against the thick gusset of my panties. The warm friction drove me crazy. I felt the warm sensation of pre-cum trickling out of me.

  My professor looked like she was having the time of her life. “Yes, that’s it, Tara! AH!”

  I couldn’t recall the last time Ms. McKay was so happy. The woman was always so cold and strict. Here, I saw the first genuine smile on her face.

  She groaned as her first orgasm wracked her. Her body shuddered and I was forced to let go of her dildo. Despite this, I knew she still had some fight in her. This experiment was far from finished.

  After she gathered her breath, Ms. McKay praised me. “What a lovely performance, Tara. I think you’re ready for the next step. Lean over the table.”

  I knew what was coming next.

  Chapter 5

  I got up from my knees and faced the conference table. Then, I leaned over the table and placed my hands on it for support. The action lifted my skirt and exposed my panties. I had already come so far. What was another humiliating act on top of this one?

  That wasn’t good enough for Ms. McKay. She stepped behind me and hiked up my skirt. Then, she pulled down my panties. She thumbed my ass for a moment before removing my butt plug.

  I instantly felt a wave of relief. I forgot I even had that thing inside my ass. It had loosened me up well and good. I knew it was to prepare me for the real deal.

  That dildo had been inside of my mouth. Now, it was going to enter me through my rear entrance. I could only take a deep breath and prepare for it.

  In an instance, I felt her shaft penetrate me to its hilt. I let out a piercing groan as the intrusion pushed me further onto the table. Before I even had a chance to gather my strength, she entered me again and again.

  It was a good thing that the butt plug had stretched my asshole. Otherwise, that dildo would have struggled to make it halfway inside of me. Whatever pain there was now had become replaced by bolts of pleasure.

  My professor thrust wildly at my ass. The strap-on ground against her cunt and pushed her towards yet another climax. Likewise, I was getting unbearably hard. My panties felt like a prison meant to encase my prick.

  I was thankful for the fact that the conference table was large and heavy enough to bear the brunt of Ms. McKay’s thrusts. Otherwise, we would be moving and skidding all over the place. My arms buckled and I fell onto the cool wood of the table. My ass was directly parallel with her dildo.

  My ‘Madam’ was completely delirious with our erotic coupling. Her body was on autopilot as she fucked me senseless. I held onto the table for dear life as she drilled behind me. With each thrust, she sent my knees banging against the side of the table. She even slapped my ass for good measure.

  I didn’t know how long she could go on for. I did know, however, that I was reaching my limit. My climax was building up inside of me like a flood against a dam. I needed to unleash my load. “I’m going to cum!”

  She chanted as she pounded my ass. “Cum for me, my little schoolgirl!”

  Together, we moaned as my professor fucked me without mercy. Together, we rocked back and forth with a single motion. I felt my climax brew in my balls. My panties were wet with pre-cum. It was just an encore of what was left to come.

  Literally.

  Ms. McKay was spent as well. Her thrusting motions were becoming more erratic. Finally, she slowed down to a crawl.

  That was my cue to cum. I cock grew ridged as a steel pole and slipped outside my panties. I came hard and gave substance to the pent up arousal in me. I was like a whale tooting his blowhole.

  My cock erupted with a stream of hot cum. It coated the conference room table with my sticky seed. I would have cleanup duty after this but that could wait until later. For now, I stroked my cock and milked it until my balls ran dry.

  It was the most euphoric experience of my life. I felt a bigger rush than weaving in between linebackers. It was even better than landing a touchdown.

  Finally, Ms. McKay took her dildo out of me. I barely felt the withdrawal. She detached her harness and praised me. “That was amazing, Tara. That piece of extra credit is more than yours.”

  I blushed. “Thank you, Madam.”

  She shot a smile at me. “I might need some more help with this experiment. I can’t promise you more extra credit but my door is always open.”

  I laughed. “I’ll think about it.”

  After we cleaned up and got dressed, I went back to being regular old Tommy.

  I immediately hated it.

  I loved being Tara and feeling humiliated. This experiment had awoken something deep within me. I couldn’t concentrate on football or the rest of my classes.

  I wanted more.

  Ms. McKay was more than happy to set up other ‘projects’ with me. It was a push and pull relationship but it worked. As she humiliated and fucked me, I saw a side to myself I never knew had existed.

  We had some awesome sessions together. I wasn’t even sure if my professor was actually doing research for a grant. She never seemed to take any notes after ass fucking me. I didn’t care if we were doing this for fun instead of for science.

  Being Tara the schoolgirl, affected being Tommy the quarterback. I found football practice easier now that I had endured Ms. McKay’s experiment. Getting hit by a tackle was like getting hit by a stuffed animal. I could endure anything.

  I also improved my academic performance. What seemed overwhelming before was now easy. I could focus on class with little distraction. Soon, I stopped being on the verge of academic probation and became one of the better students in class. My GPA skyrocketed the more I visited my ‘Madam.’ Hell, I even made the cutoff for the honor roll.

  The rest of the sports season was a blur. I led the team from victory to victory. When I made the game winning touchdown at an important game, I made sure to thank Ms. McKay for shaping me up into a proper student.

  She was in the stands cheering me on. I met with her after our victory. With a brilliant smile on her face, my professor told me. “I hope you don’t mind seeing me after class tomorrow, Tommy. I know that you don’t need extra credit anymore but I’d like to meet with you all the same.”

  I smiled back. “With pleasure, Ms. McKay.”

  Chapter 1

  Did I ever tell you the joke about the comedian who couldn’t find work?

  Well, I happened to be the
punchline.

  “Sorry Mark,” he told me. It was a familiar phrase at this point. I still hated it no matter how used to it I had become. “We’re all booked up for the next couple of months.”

  I forced a smile on my face and replied. “Thanks anyway, Jim. Keep me in mind if another gig comes up.”

  “I will,” Jim replied with a sigh. I didn’t know whether he was tired of looking for a gig on my behalf or that I kept pestering him on and on about it. Nonetheless, the bar owner paused and said. “If you have a lady friend, point her our way. We might have something for her.”