Join the best erotica focused adult social network now
Login

Bruised Heel

"Crossdressing student gets caught and toyed with."

4
0 Comments 0
133 Views 133
4.8k words 4.8k words

Author's Notes

"This was my first attempt at writing something like this. Any educational institution, people, or places mentioned here are purely fictional. All persons characterized in this story are 18 and older."

L'art de plaire est l'art de tromper (The art of pleasing is the art of deception).

"So are you going to help out with this project or not, Joey?"

Jessie was asking about me helping out with an upcoming art show. He was asking me in particular to be present for any technical mishaps. Jessie's art exhibit was a holographic display; thus, he needed someone with experience in optics and engineering. Someone like me—my major was in electrical engineering. At 21 years old, I was close to graduating. Jessie was studying graphic design and economics, the first steps to a potential MBA. The university we were both attending in New England had (and still has, in my opinion) a robust program in advanced computer sciences.

Here we were, in the stands of a soccer field, along with a small crowd of locals and students watching an intramural match between some guys in casual sportswear. Spring was turning into summer, and the tits were out on campus. Around this time, exams were wrapping up, and the game was a nice break from all-night study sessions. The match wasn't terribly exciting, but Jessie and I had a thing for the sport. I turned to Jessie to respond; his focus was on the game.

"If the device is set up correctly and the program works fine, I really don't think you need me there, bud."

I could tell Jessie was nervous. He wanted the project to go off without any screw-ups. Having me there was more for his comfort than anything else. I wasn't opposed to going with him at all. My exams had gone well, and I wasn't too busy with lab duties for the engineering department. But Jessie can be obsessive when it comes to his pet projects.

"It has to be perfect. Once things get rolling, I just need you to monitor the system and make sure the shit doesn't fail on me. I want the audience to be impressed. They'll have food catering there and a bar too, but you have to pay for the drinks."

The mention of booze got my attention.

"Are any girls going to be there?" Balore is a small college town. "Are you going to be my wingman, bro?" I was hoping to meet someone new. My last relationship ended pretty quickly; she wanted a long-term commitment that I couldn't give. We were both too young for that anyway.

"Sure, dude, plenty of female artists from the local college and New England itself. Balore is coming up now, whoa! Jessie quickly turned his attention to the field as one of the players took a nasty fall forward. Yikes, it didn't help that the grass was synthetic. For as much money as they were charging in tuition, they could at the very least invest in organic grass, not this new synthetic hybrid shit.

"That's going to leave a mark," I said.

"Heh, no shit," That was all Jessie had to add. I figured I'd use this opportunity to pack it in. Some of the players were helping out the one who fell. He was wearing a red shirt with black shorts. He was about my height, maybe smaller (I couldn't tell for sure), with jet-black hair done up in a man bun in the back. His body was lean with a slim, toned upper body but thicker thighs and legs. A good-looking guy facially, he must have gotten a lot of attention from the ladies. Anyway, it was time to head out.

"I'll be there; send me the schedule and the address." Wait, does this thing have a dress code?" I really hoped it didn't. Shopping was the last thing on my mind.

"Business casual, nothing fancy." Jessie gave me an amused look. We had been friends for a while; he knew me well enough by then.

"Alright, see you on Saturday." Send me the link to the website." I got up and walked back to my apartment. Classes were winding down with the summer break coming up, as well as my lab work with Professor Katz. I received the link and the schedule from Jessie a couple of hours after arriving at my place. The "Balore Art Show" at Balore College, situated in the small town of the same name, was a show of technological art. AI images, 3D-printed sculptures, and other oddities. Jessie's piece would surely fit right in. I was scheduled to be there 30 minutes prior to 6 pm.

************

Saturday night was warm and humid, so I made sure to dress light in blue chino pants and a teal dress shirt with a hint of cologne sprayed on. The showroom was rented by the school for the event. It was impressive for a small college like Balore to be putting on an event this big. There were lots of artists from across the region. A room full of students was busy setting things up for the show when I walked in. I found Jessie in a rotunda along with Selena, who had partnered up with him on this project. They had the holographic project set up next to some other team displaying a piece of "bioart" (very creepy stuff if you ask me). I checked my watch; it looked like I was right on time. They must have gotten in a little earlier.

"Hi, Selena, you look good. How is the setup going?" I gestured towards the optical device. At 5'5", Selena was a gorgeous young lady with honey brown eyes, beautiful ginger hair, and a bright smile, wearing a dress shirt and jeans. She had a decent amount of muscle on her pear-shaped figure, the benefits of many hours in the gym. She had her major in graphic design at the time. She and Jessie had been long-time friends since grade school. I was always surprised the two of them never got together. For Jessie, Selena was like a sister to him since their families were pretty close even before they were born.

"It's coming together." I need you to check the wiring. I'll be back for the show later." She started for the west side of the building, where the bar was located.

"Going to get a drink already, damn girl?" I gave her a wry smile. Her reply was a middle finger as she walked off. That girl knew how to have fun.

The show went as well as Jessie could have hoped. After a wiring check, I monitored the system from my laptop close by just in case. Those types of systems had a habit of overheating, so that dominated my attention. Selena would pop in to talk to the patrons about the display. The rest of the time she was at the bar chatting up a local from the college while Jessie and I entertained the guests. There were a lot of couples with kids in attendance, prospective students, local politicians, professors, and visitors from out of town. Jessie's display (an incredibly realistic depiction of the Mona Lisa) sort of took a back seat to Jessie himself. Jessie was handsome with a full head of shaggy brown hair and piercing blue eyes. He may have been slim without any kind of masculine build that other guys had, but that didn't stop girls and even some older ladies from showering him with attention. He was the art show as far as they were concerned.

After 2 hours of entertaining guests, the two of us were in desperate need of a drink. We caught up with Selena at the bar, sipping IPAs with another girl. The bar itself was tucked away from the catering service close by. A small group of patrons had gathered to drink and watch the sports channel. The woman was showing Selena pictures on her camera. I got a good look at her as we approached. She had to be about 5'9", with black hair with purple on the ends to match her violet lipstick. She had high cheekbones, a lovely Greek nose, and a slim-thick figure. Her eyes were the most striking feature. They were grey, almost silver eyes; I was pretty sure she had contacts on. She was drop-dead gorgeous.

"Time to mingle," I said, and we bumped fists. Jessie and I had attended enough parties to know each other's game plan. We made our way over to them at the counter.

"Selena, I think Jessie's display was a hit. Who's your friend?"

"Excuse you, SHE is my soulmate. I love this girl. AND NO, you can't have her. Get lost." The two of them started chuckling like teenagers. It was clear Selena was tipsy, her friend not so much. Jessie had made his way to the bar, ordering his drinks and chatting up a redhead on his right.

"My name's Valerie, so you're the engineer. I can tell," she said with a smirk.

"I'm Joey. How can you tell?" I asked, full well knowing I would probably be made, the butt of some lame nerd joke.

"You look like you haven't stepped outside in a year." Too busy spanking it?" I guess that was a reference to me being pale. Selena was doubled over by now. They were both having a good old time at my expense.

"Ah ha, fuck you too, chica. I get plenty." I shrugged it off; that wasn't going to stop me from shooting my shot. I sat at the other end of the bar next to her and ordered the local brew. It gave me enough time to rethink my approach and make my move.

"So let me guess, accounting major, right?" No, you seem more like a coder." She was wearing a black Baylor College shirt with jeans rolled up at the ends. I figured guessing her field of study would help strike up a conversation.

"Computer science and photography, if you need to know." She was amused. Selena piped up at that point.

"She's really good. I saw some of her work. Show him your camera footage from the lake."

Valerie pulled out her camera; it was one of those fancy hi-def devices with the large scopes. She was indeed really good. She handed me the camera with a gallery of photos from a nearby lake loaded on the screen. One of them captured a swan in mid-flight just above the water's surface. The resolution was impressive; she clearly had a knack for this. As I was looking through her gallery, I noticed a scar on her leg.

"Did you get that scar shooting photos in the field?" I gestured toward her foot.

"No, I just slipped on a jog." She took back the camera. "You should try it sometime. "You know, jogging, spend enough time outside, and maybe you'll actually get laid." She smiled and went back to chatting with Selena.

'WTF, is that supposed to mean?' I thought to myself. At 5'11" and 185 lbs with short-cropped hair and dark brown eyes, I was in pretty good shape.

At this point, I was done talking to this brat. Something was off with her. For the next half hour Jessie and I were drinking beer and watching sports. Jessie had been making progress with the redhead from the art department. There weren't too many patrons since most of the art connoisseurs consisted of couples with children, bigwigs, and young prospective students. I chatted with two other girls, both of whom turned out to be under 18 (jailbait), so that didn't turn out too well. For the rest of the evening, I just hung out with Jesse. After 6 or 7 (I don't remember exactly) beers, the bartender cut me off. It was near closing time anyway, so I decided I would make my excuses in another 5 or 10 minutes and head home.

Checking my phone out of boredom, I noticed a social media notification for a soccer group on campus. Their account was just created an hour ago, which was curious. Since it was still public, I checked their page. There were members listed off to the side next to photos and videos of them on the field. As I was scrolling through the list, I came across one fellow who seemed familiar to me: Zachary Vidman. He was the guy who took that nasty fall on the field that day. I knew it was him because I recognized his man bun, but that wasn't all I recognized.

"Huh," I said absentmindedly. My spidey senses were tingling.

There was a full-body photo of him with another guy in sportswear on the field. The bruise was still fresh, I suppose. I thought the alcohol was getting to me because the bruise looked similar to Valerie's. It was even in the same area of his leg. In fact, Zack himself appeared to bear a striking resemblance to Valerie. Same dark hair, high cheekbones, full lips, and creamy white skin. The eyes were a different color, though. Maybe they are related? But that didn't explain the scar. There's no way Valerie could be a dude in drag!? Selena rose from her chair and started heading towards the restroom, I think. As Valerie followed, I discreetly took several photos of her from behind. I even managed to capture her face in profile. Using a smartphone app, I compared the two pictures. It wasn't an exact match for obvious reasons, but every crucial detail lined up perfectly. Even the bruises were the same. No… no way!

"Holy shit…" I whispered.

"What's up? Joey?" Jessie must have overheard. I exited out of the app; I didn't want Jessie to think I was crazy.

"Nothing, just... um." The alcohol was tripping me up. "What happened with that cute redhead?"

"Her name's Cass. We set something up for later. Redheads aren't exactly my type, but I think we have chemistry."

"That's great. Do you know anything about Val? I mean, Selena seems to love her. Is she a friend of hers or yours?" I was curious if he knew anything.

"Valerie. No, I've never seen her before. Selena just met her today." Jessie wasn't going to be much help. Speak of the devil, the two of them were on their way back from the little girls' room. In that moment, I had a bright idea on how to solve this mystery.

"Jessie, you should probably take Selena back to campus; it's getting late." Besides, she has been hitting the bottle pretty hard."

Dulceencanto
Online Now!
Lush Cams
Dulceencanto

Jessie nodded and asked, "Are you going to hang out here? The bar is closing, dude."

"No, I am going to give it one last shot, if you know what I mean." Selena cut in to the conversation, asking, "Jesse, are we hitting up the town or what?" I know a rustic bar a few blocks away. They serve the best food there, Val."

Instead, Valerie said she needed to head back to her dorm room at Balore. Selena was disappointed; I was elated. That was my moment; I had to time it just right. I used my account to send Zack a message with the picture of Valerie: "Is this you? ;)"

A few moments after Jessie and Selena were headed out the door, Valerie checked her phone. The color draining from her face told me all I needed to know. She was caught; there was no question about it. Zach and Val were the same person.

I needed to act fast. As carefully as I could, I approached her and put my hand on her back. Val was slightly startled; she turned to face me. "Her," or rather "his," lovely silver eyes screamed fear, shame, and panic.

"Easy there," I said. He was caught, and he knew it. At that moment, I was in control.

"Just breathe." No one else needs to know." I said. He studied my face.

"Please... don't. Just." He couldn't complete a sentence. Even though it was close to closing time, there were still some patrons in the dining hall, mostly older couples eating or just standing about waiting. I wasted no time in hooking my arm around his and guiding him out.

"It's alright, let's go someplace more private." We exited the building and went to my car. He got in and buckled up, still shaken from being discovered. I asked for his address, and we drove to his place since it was less than a 10-minute drive.

Pulling into the neighborhood and parking close to his apartment, I could tell he came from some serious money. It was a closed-off community on the east side of town. Zack was so nervous that he dropped his keys multiple times trying to unlock the door. I was stunned when we entered his house and he switched on the lights. Apparently, the whole place was his. He had a big-screen TV in an immaculate living room; the kitchen was gorgeous with granite countertops and a smart fridge. A china set in the dining room with a beautiful chandelier.

"This place is yours?" It's beautiful." I was impressed.

"Yes, my…my family is well-off." Um, how?" he asked.

I didn't understand the question "How, what?"

"How the hell did you know, you fucking idiot?" He was shaken; now he was pissed off and red in the face, almost crying from fear.

"The bruise. You took a nasty dive on the field back at Uni; I was there with Jessie. Soccer is kind of my thing." I shrugged off his rage, keeping my cool and, more importantly, control over him.

"Fuck! Oh my god, are you sure no one else knows?" He was almost pleading with me. He was holding back, trying to keep it together. I didn't want him to be afraid. I wasn't quite sure how I wanted this situation to end, to be honest.

"I'm pretty sure Jessie and Selena don't know, or anyone else for that matter." There was a liquor cabinet nearby; I decided to help myself to some vodka and ice.

"Okay, okay, okay." He was trying to calm down. All he was really doing was making me nervous, pacing back and forth. Then, he stopped and looked at me with those grayish-silver eyes full of intensity.

"You have to delete that photo of me." he demanded.

I scoffed, "No, I don't. Hey, this is your fault, you know. If you were nicer to me earlier, I would have let it slide and kept my mouth shut. But right now, my silence will come with a price." I took a sip of my vodka as he stared daggers at me. To this day, the memory of what happened feels more fiction than fact. And listen, you guys reading this probably think I am an asshole for doing what I did. To that I plead guilty, but you guys would have done the same; be honest with yourselves.

"Really! Oh, for fuck's—" He proceeded to massage his temples, trying to work the knots generated by offense and exasperation. I took the opportunity to look him up and down. I hadn't considered myself gay or bi beforehand, but damn, he was so hot, there was no denying it. The dark purple hair framed his feminine face perfectly, along with those piercing eyes. The muscles in his arms did well to complement his slender shoulders. The tight jeans he was wearing could do little to hide his muscled legs and rotund bubble butt. His body was simply a work of art, and most women would kill for an ass like that.

"Fine, how much?" He looked at me with hands on his hips, similar to what girls do when they are upset with their man. I took the exact same pose to twist the knife in a little more, which only served to enrage him even further. Time to cut the bullshit. I closed the distance and pulled him in by the waist into a slow, gentle kiss, testing the waters of what was permissible. When he kissed me back, I went further, and before long, we were making out in the living room. With my hands, I explored the muscles of his back and squeezed his rear end while his hands examined my muscled chest and abs. He tasted of mint gum and hops from the beer. I broke the kiss.

"Let's go upstairs; show me your room."

In moments, we're up the stairs in his bedroom. I was anticipating a bit of a mess, but the place was neat and clean. We continued our make-out session with the light set to a slight dim. Whatever panic or fury seems to melt away with Valerie. He was more focused on unbuttoning my shirt. I took it off and tossed it to the side, then sat on the bed while discarding the rest of my clothes. I gestured for him to come closer.

"Val, take your clothes off." He was nervous, maybe a bit shy about exposing his body. After a few moments, he dispensed with his Balore shirt and undid the padded bralette underneath, revealing a willowy chest with bright pink nipples. He then proceeded to unbuckle his jeans and let them drop. He had some light muscle in his upper body but was much more developed in his lower half.

His muscled legs were incredibly sexy and had almost no hair whatsoever except for some peach fuzz around his groin, covered with a pair of erotic, lacy black panties. I noted he was packing a respectable 6 to 7 inches down there. Not bad coming from such a feminine-looking dude. All in all, Val was drop-dead gorgeous. I needed to keep my cool and reassert my dominance now. Standing up and looking in his eyes, I pointed to the floor. No words were needed; he knew exactly what I wanted.

Val, blushing from the heat of the situation, looked away for a brief moment and then got on his knees. He was now eye level with my crotch. Tentatively, he reached the elastic band of the briefs with his fingers and, in one swoo,p brought them down to the floor. My 9-inch cock sprung forward like a jack-in-the-box. He pulled back a bit, obviously not expecting to be confronted with my large member. It was always a thrill when girls expressed shock and surprise when they saw my dick. "Nerds have BIG hard drives" was the line I used to tease women with in those moments (it's cheesy, I know).

He reached out his hand, grabbed my cock, and started jerking it. His hands were so soft and delicate for a guy it was hard to believe. He looked up at me for a second, gauging my reaction, and proceeded to kiss the tip, working his way up to mouthing the head. After a few minutes he was sucking it; the pleasure was incredible.

"That's it, chica, work that big dick." My encouragement was well received. Eventually, he got half of my hog in his mouth. Bobbing up and down while swirling his tongue around the head. It wasn't his first rodeo, I gathered from the job he was doing. 10 minutes of his oral techniques got me close, but I needed to get inside his throat. I put my hand on the back of his head and slowly started to run my cock closer and closer to the entrance. He gagged a bit, and I let him take a second to breathe. After a small break, I told him to take a deep breath.

With that, I shoved my cock back in his mouth and squeezed into his tight throat. His eyes went wide in surprise and slight discomfort. With his chin nestled against my balls, in that position, I got a good peek at his milky white ass cheeks swallowing up his panties like a g-string. It was almost enough to make me blow my load right then and there, but I kept my cool. Eventually, he started tapping on my thigh for air; I released him and let him catch his breath.

"Damn, you really know how to work a cock." I helped him off the ground as he was trying to regain his balance.

"Thanks. You are bigger than—cough, cough—bigger than I am used to." He brushed some hair aside.

"I can believe it." I smiled.

"Don't think you are all that, just because Whoa wait-" He was surprised and even started to whimper as I ran my cool hands up from his legs to his plump butt cheeks. My mind couldn't comprehend how a man could have so much junk in the trunk. As I spread his right cheek with one hand, I traced the line of his panties down with my fingers and began probing his asshole.

"Whoa, wait a minute, I'm not sure if I'm up for that."

"Have you never done it before?"

"It wouldn't fit, I don't think." He was anxious; I decided to play it off.

"Ha ha, flattery will get you nowhere, madam." With that, I lifted him up by his waist, turned, and placed him on the bed while simultaneously removing his lacy underwear. I reached into my pants pocket for the packs of lube I usually carried, just in case I got lucky. Understanding my intent, he held his right leg up for easy access. After smearing a considerable amount on my dick, I lathered some on his entrance and prepped him with my fingers. First one finger, then two. I made an effort to go slow and was rewarded with soft moans. Gauging his response, he seemed to be relaxing. I figured he was ready.

"Listen, c-can you go slow? I haven't tried this yet." He looked past me as he spoke, not wanting to meet my gaze for more than a moment.

"Absolutely, I won't hurt you, Val." It felt surreal that he had never done this before, but then again, neither had I.

He nodded and held both his knees close to his chest. Placing my cock at his virgin hole, I began to apply pressure. I took my time and slowly but surely began to enter him. He tensed up slightly when I had pushed 1/3 of the way inside. His insides were so tight around my shaft. With my free hand, I rubbed and pinched each of his nipples, causing him to moan and bite his bottom lip, which was so cute. As he began to relax again, I picked up the pace, pushing my cock to and fro, each time diving deeper into his ass. His dick practically stood at full attention when I finally bottomed out inside him.

"God, fuck, that's so deep." All 9 inches were buried inside of him. Reaching down, our lips met again in passionate kissing.

"Not too deep, I hope."

"No, it's g-good. I can take it if you want t-to pick up the pace."

"Parfait." With that, I ramped up my assault on his silky anal passage. Val's guttural grunts as I was pounding him were so erotic, they served to add fuel to my thrusts. A few minutes later, we had a good rhythm going. Val's penis swayed back and forth, bouncing off of his flat tummy. His eyes were filled with lustful passion and desire for more; I could tell he was enjoying this as much as I was. I hadn't been this excited to fuck since high school prom (what a disappointment that turned out to be). This was so much better.

"Fuck, Val, it feels so nice being inside you; you are absolutely gorgeous. Turn around, I want to see that ass." Once he regained his balance, he got into position on all fours. I jiggled his ass, marveling at how big and plump his cheeks were. Completely smooth and hairless with a cute little birthmark on his left cheek. Being impatient, I shoved my cock back inside his needy hole and started fucking him harder and faster than before. Now we were both on the bed, kneeling as I grabbed his hips as tightly as possible and kept pounding him as deep as I could. His ass wobbled obscenely from my assault as my nuts collided with his thigh.

"Shit! Oh, fuck. I can't, ahh, shit!. I'm c-close!" Val tensed up, breathing hard as he climaxed, spraying cum on his bedsheets. His insides pulsed and squeezed on my dick, practically milking the cum out of me. I must have fired 7 or 8 volleys up his fat butt before pulling out and collapsing next to him.

"Holy shit, that was awesome. Valerie, you are amazing." I turned to face him and brushed some of his hair aside as he lay face down on the mattress and panted hard, catching his breath.

"Thanks. Y-you're not so bad yourself." We were both spent. Before he passed out, he made sure to make me promise to keep my silence about his little secret. Of course, I had no intention of telling anyone; that was leverage I planned to use for more fun going forward.

Published 
Written by BullfrogPrince_
Loved the story?
Show your appreciation by tipping the author!

Get Free access to these great features

  • Create your own custom Profile
  • Share your erotic stories with the community
  • Curate your own reading list and follow authors
  • Enter exclusive competitions
  • Chat with like minded people
  • Tip your favourite authors