Kevin Gets Caught

Kevin Gets Caught

By: Deana Bard

At nineteen years old, Kevin appeared to be your average college sophomore studying computer sciences. On the tall side and average to slim build, he played on the lacrosse team and a chess club member. As far as anyone was concerned, Keven was like any other student at the state university.

At least, that was the Kevin he allowed everyone to see.

However, privately, at this very moment, he was wearing a garter belt and panties, both off-white. Up next, he prepared to pull a pair of stockings up his legs. One leg at a time, over a covering of fine hair, he carefully unrolled the nude-colored stockings up before clipping each to the dangling suspenders of the garter. Checking himself in the mirror, a satisfied smile crossed his face.

Opening a dresser drawer filled with bras, he found a lacy off-white bra. Smiling broadly, he held it up, examining his find before slipping his arms into the straps then reaching behind to hook the ends together.

Once the bra was clasped, he emoted a self-satisfied moan. Getting this done up had been a long time coming. He also loved the way his long hair tickled his otherwise bare shoulders. Checking himself in the mirror, he wondered if he should go a little further.

Kevin and his girlfriend, Amanda, had been going together since the middle of the previous semester. Slowly, over a period of weeks, multiple bags and then boxes of his stuff had ended up at her place. Finally, before the start of the new semester, they made it official and he canceled his dorm assignment.

It was late afternoon when he had returned from his last class, and instead of finding his girlfriend waiting there for him, he discovered a note on the table. The message read: "Last minute invitation. Sorority party tonight. Sorry!" It was signed "Mandy" and a heart. There was a PS. "Why not have a party of your own. The place is all yours. Do whatever you'd like."

With the knowledge that he'd have the apartment to himself at least until the wee hours, it seemed like the perfect time to do what he'd been longing to do for some time. Amanda had a closet full of clothes that he had been keen to try on. Finally, this would be the ideal opportunity to let out that other, well-hidden side of himself.

But for right now, being dressed in only women's lingerie with no one else around was quite a treat. Posing for himself in the mirror, he was startled when in walked Amanda along with her best friend. "Gotcha!!!" she shouted. Shocked at being caught, his face instantly turned crimson red. He attempted to make up an excuse. But Amanda interrupted, "I've known that you'd been going into my dresser, but I would never have guessed this about you."

Her friend snapped a picture, then chimed in, "He does look cute," and giggled. Kevin turned his back to them and quickly unhooked the bra and began taking it off when Amanda yelled, "STOP! No, you don't. Put that back on." He hesitated until she snapped at him. "All the way on. We want to see the whole deal." Glowing red in embarrassment, he did as she commanded.

After a bit of nervous fumbling, he got the clasp hooked again and stood before the two females. They ordered him to turn and model for them so they could critique.

His embarrassment only grew as Amanda's friend continued taking pictures. "Come on, Tamika. Stop with pictures already!" he begged.

But his Amanda interjected, "Go right ahead, Tam, I'm just trying to decide what to do with those pictures."

"Wha ... What do you mean, Mandy?" he asked. "You're not actually thinking of showing them to anyone. Are you?!" The panic in his voice was intense. "PLEASE, Amanda! Tamika! You can't let anyone see me like this."

"I don't know, Kevin," replied Amanda. "This is too big a deal to just let it go. Going through my stuff is bad enough. But wearing my underwear, well, that's going several levels beyond normal boyfriend behavior."

Staring at her phone, Tamika chimed in. "Ya know, Mandy. These are just begging to be shared." The look of disbelief on Kevin's face was priceless. "What do ya think, girl? Should I put them up on Snapchat? Instagram?" Tamika began opening apps on her phone. "Or, we could post them to his Facebook page? I know, let's send it to the guys on his lacrosse team."

Panicked, Kevin pleaded, "PLEASE! I'm sorry, Mandy. What do you want from me? I'm really sorry! I'll do anything to make it up to you. I'm begging you not to send any of the pictures." Just then, he saw Tamika tap her screen, and a split second later, Amanda's phone dinged, and he knew one or more pictures had been sent. "Oh, my god! No!!!" He began to sob.

Tamika took another picture. "Look, Mandy. He even cries like a little girl," and she took some more pictures. "These are priceless." This caused more tears.

His girlfriend put her arms around him. He hadn't known this before about his girlfriend, but she had always had a soft spot for guys who allowed their emotions to show. Nestling into the crook of her shoulder and her embrace only brought out more tears as he sobbed for forgiveness. Amanda spoke in a soothing tone assuring him that Tamika had only forwarded the pictures to her and no one else.

Relieved knowing that, so far, anyway, his secret was just between the three of them, he was able to calm down some. However, Amanda still felt that her boyfriend had been punished quite enough. Pushing Kevin back to arm's length, she said, "But you do have to make this up to me. Do you understand?" Wiping his eyes, he nodded. "You and I are going to need to re-examine our relationship and how this cross-dressing thing of yours might fit in. Got it?"

Kevin hung his head in shame but gave a nod of resignation. The last thing he wanted was to lose Amanda as his girl. Her feelings towards him, especially after this, were uncertain. But he had fallen deeply in love with her and knew he'd do just about anything to keep them together.

"Now, This party Tamika and I are going to is a more dressy affair than we thought. That's why we came here, to change. Tam and I were going to shower together then get dressed. But now I'm thinking I need to keep an eye on you, so you don't get into trouble again."

He began promising to be good when she said, "Hey! I just got an idea. Tam? The sorority thing is a girls-only party, right?" Tamika had already begun getting ready to bathe and confirmed the statement. Amanda returned her attention back to her boyfriend. "You did say you'd do anything to make this up to me, right?" Cautiously he nodded. "I'm thinking that we all go. Get what I'm saying? We go as a threesome. Just us girls!"

Tamika caught on instantly. Before Kevin could protest, the girls had him stripped and hauled into the bathroom. In a flash, they were just as naked as him, and they all piled into the shower stall where the girls began lathering and shaving him from head to toe.

The fact that both Kevin and Tamika were seeing each other naked for the first time didn't prompt the slightest trace of jealousy from Amanda. Neither did Tam being so hands-on with her boyfriend. Amanda remained upbeat as the two shaved him. Not just his legs and arms. They removed every strand of hair that grew below his nose on down, including his pubic hair.

There was no question that the girls were more than just best friends. A fact that Kevin had already been made well aware of. They shared everything with each other, including their bodies. While Keven would be out playing chess, they used the time to play their own games. Not only didn't Kevin feel threatened by this; instead, he found the idea of two girls doing whatever two girls would do together quite intriguing.

Next, it was time to shower -- all three together -- to rinse and wash his now hairless body. Naturally, Kevin was enjoying taking a shower along with two lovely naked ladies.

He couldn't help it. Being the center of their attention caused his dick to stiffen. But when Tamika's eyes widened, Kevin became self-conscious. When she took his dick into her hands, his cheeks reddened with embarrassment. He knew that he wasn't overly endowed. Still, as far as he was concerned, his erections were decent in size.

However, Tamika couldn't pass up the opportunity to further humiliate her friend's boyfriend. "Huh! Doesn't it grow more than this? It's not nearly as big as I thought it would be."

Instead of taking exception to Tamika's forwardness, Amanda simply replied, "That's okay. His tongue always makes up for his shortcomings." Keven couldn't believe that his manhood had just been assaulted twice over. Interestingly, these humiliating put-downs only caused his boner to pulse with excitment.

Once Kevin was all rinsed off, he was sent off to redress while the girls finished showering themselves. After dying off, he did as directed. He obediently put on what he'd been caught wearing: the garter belt, panties, stockings, and bra.

When the girls emerged, they immediately checked to make sure he'd done as they instructed. To their delight, his bra was well stuffed, and his maleness was expertly tucked away. Together, the girls remarked how he looked even sexier than before. Kevin blushed while quietly stating how he never knew how much better everything could feel without all that body hair.

The girls picked out what they would wear, then, for Kevin, they chose a flowing cream-colored dress with a black leather belt to be worn around the waist. Not too casual nor too formal.

But before having him put it on, they agreed that something needed to be done with his hair. This led to a suggestion for doing a full makeup job. Passively resigned to this makeover, he sat patiently as Amanda hot ironed and curled his none too short hair. At the same time, Tamika plucked and shaped his eyebrows. She then applied foundation, pancake, then a bit of shading and shadow to his face, creating an impressive feminine-like appearance.

By Kevin's demeanor, the longer and more involved this became, the more he enjoyed himself. Clearly, he was relishing the attention of the girls. But also, he was extremely curious how he would look when they were done. After some eyeliner and doing his eyelashes, he slipped into the dress. It fit perfectly. With the belt cinched around his waist, it enhanced and emphasized his hips, butt, and chest. Without a slip, his underwear was just barely visible. When leaning forward, the tops of the lacy bra cups peaked into view.

The girls admitted that he looked even better than they did. It was at this point the girls suddenly realized that Kevin needed a pair of high-heel shoes. "Well, his big feet will never fit into any of my shoes," Amanda said.

Smoothly, Kevin rose from his chair, saying, "I've got a solution." Opening his bottom dresser drawer, he removed a crumpled bag from the back. He opened the bag and produced a shoebox along with a few pairs of panties. Inside the box contained a pair of black t-strap pumps with three-inch heels in just his size.

His secret was a secret no more. Both girls stared in disbelief. Trying on women's wear today had not been some crazy, one-time fluke. Evidently, today had hardly been the first time that Amanda's boyfriend had worn a dress and heels after all. While Kevin, now Kelsey, proudly displayed a well-practiced ability to walk in heels, he spun and modeled the outfit for the stunned girls. "Thank you both so much," he said. "This is like a dream come true."

Obviously, this was a complete surprise to the girls."Okay. let me explain. Back when I was seven or eight, my mother and sister began dressing me as a girl. I didn't know why, but I did know that I liked it. The way they would fuss over me. Putting me into my sister's hand-me-downs, giving me perms, and painting my nails. And I've been cross-dressing ever since. At least, I did until I started college." After a moment of reflection, he added, "Mom even had me wearing makeup and heels around the house years before my big sister was allowed to."

Kevin fought against -- or was relishing -- the embarrassment caused by reliving his past. "Mom gave me these shoes as a graduation present. But sharing a dorm room with other guys, I hadn't had much of a chance to put them on."

Amanda, still stunned by her boyfriends' admissions, asked, "How the hell didn't I know about any of this?"

"Rotten timing on my part, I guess. It's not that I wanted to keep any secrets from you. But, you gotta see how hard it is for a guy to come right out and say, Oh, by the way, I like to cross-dress. But you have so many lovely and sexy clothes it's been hard to resist. Yes, I had gone through your drawers. But that was just to touch and gaze at all your sexy underwear and imagine how they would look on me. Today was the first time since we've been together; I finally gave in to the temptation to dress. I just never intended for you, or anyone else, to find out."

As Kelsey was giving her explanation, she picked out a pair of Amanda's earrings. "One more thing my mother did to me, or for me..." Hooking an earring into each lobe. "For my tenth birthday, I had my ears pierced."

Throughout this, Tamika was video recording. Even if no one but her and Amanda would ever see this, she knew it was worth keeping.

In the end, the girls made it a point to fulfill the one previously unfulfilled dream of Kevin's: To go out in public as Kelsey. However, instead of going to "that silly party," Mandy and Tam conspired to really take Kelsey out in public. Much to Kevin's surprise, the car pulled into the local nightspot where all the college kids, and many of the locals, hung out.

This was far more than Kevin had bargained, and his hesitancy delighted his girlfriend. With a girl pulling on each arm, he kept saying, "I'm not ready for this. I'm really not ready for this." Once inside and after a stiff drink, they escorted their reluctant companion to the dance floor. Feeling certain that someone would recognize Kelsey as being Kevin in drag, he looked around nervously. This tickled the girls no end.

Back at their table and another round of drinks, Kevin began realizing that so far, no one had seen through his disguise and started to loosen up. Back out onto the dance floor, Amanda, Tamika, and Kelsey went. No more than twenty minutes had passed since they arrived, and the three 'girlfriends' were having a marvelous time.

Naturally, it didn't take long before all three garnered the attention of numerous single guys wanting to join in. Who then followed them back to their table. Guys of all ages kept coming over to chat up the girls with offers to buy drinks in exchange for a dance.

An hour in, and still no one had given a moment's suspicion as to the person behind the facade. Not even a guy from one of Kevin's classes and another from the chess club. On the contrary, The guys were possibly more gentlemanly towards Kelsey than the girls she had arrived with.

Again, this did not cause any jealousy on Amanda's part. Instead, for the entirety of their time at the club, both girls made sure that Kelsey was never without someone to keep a drink in her hand or on the dance floor.

The more Kevin had to drink, the more of Kelsey emerged. And with so many convinced that bubbly Kelsey was a vicarious female, doing anything to raise doubt would have been disastrous.

But when one fella leaned in to give Kelsey a kiss, Mandy and Tam were all eyes waiting to see what Kevin would do. The girls' chins hit the floor when Kelsey casually leaned over to meet the guy's lips.

After that, for every slow dance the DJ played, Kelsey was never without an eager dance partner. Those dances often brought about more kissing. As the evening progressed, the snuggling and kissing increased.

Amanda was getting absolutely turned on watching her boyfriend kissing these random guys while dressed as Kelsey.

Some of those kisses were surprisingly protracted. But, after all, what's a girl to do? Kelsey had no choice but to return their affection and leave them hopeful.

Tamika has the photos and videos to prove it.