Supportive Friend's - Extended Cap

 

Dawes recently got dumped by his girlfriend. He thought everything had been going well until one night he got a call that ended with “we need to go our separate ways.” While initially upset and hurt by the decision, a new sense of clarity and strength emerged from the loss. An opportunity to be a better, more fulfilled version of himself became apparent. He realized that for years, he never allowed full exploration or self-expression to be apparent, instead allowing himself to conform to those around him. Today was the day it stopped.

Dawes was a straight man; he loved women, and the only sex he’d had any interest in was women. Despite his masculinity, Dawes had a secret side to him, which only a few people knew; he liked cross-dressing. In his teens, he’d enjoy frequent cross-dressing sessions, wearing his sister’s clothes when home alone, but as he grew up, the thrill of wearing women's clothes morphed into wearing panties and wearing women’s shorts. Rhett knew that much, and for the last few years, he’d been wearing exclusively women’s panties. Some were flashy, with various styles, designs, and fabrics, and others were more basic with solid colors. Either way, he’d stopped wearing boxers years ago and only wore panties. One of his ex-girlfriends knew that, and they didn’t particularly care, to his relief, as long as he didn’t try to wear their panties or wear thongs, which Dawes had no desire to do.

Dawes, now single, began questioning and exploring his feminine side. He was wearing shorter shorts in public, both as a boost for his confidence and to catch some sun. Dawes was focusing on being himself and not caring about others’ opinions. What he was wearing wasn’t wrong, nor inappropriate, so what did their opinions matter? He began reading and even writing various crossdressing and feminization captions as an outlet to explore this previously ignored femininity. As part of his progress, Dawes wanted to be more open about his feminine side and not lock it behind his mask of masculinity. He can be both masculine and feminine, keeping himself authentic and attracting people who are like him.

Colette was a close friend of Dawes. They’d known each other for years, and while there were no romantic feelings between them besides friendship, they often discussed intimate and personal details about themselves. There was no filter or judgment between the two as they joked. Following the breakup, Colette was the only person Dawes could seemingly be authentic to, so while planning a Christmas week adventure to the mall, Dawes took a deep breath and asked if they could visit Victoria’s Secret. Colette, without missing a beat, jumped at the idea and agreed.

When they arrived at the packed mall, they wandered through various stores as Dawes disclosed more of his feminine personality. Colette didn’t need the outright admittance, since she thought something was up when Dawes’s eyes lingered too long on the display lingerie at Victoria’s Secret. No judgment, as Dawes confessed his likings to women’s underwear, and his desire to be feminized.

Colette asked if they wanted to venture deeper into the store to see more lingerie, to which Dawes excitedly agreed. They wandered through various displays, discussing various styles and preferences. To Colett’s surprise, Dawes knew a fair bit about women’s lingerie, too much not be an enjoyer. Dawes confessed he liked lingerie; he’d bought a few sets for his exes who never wore them for various reasons. While he disliked that, Dawes expressed interest in owning a set himself that he could wear when he wanted to and not be reliant on another to dress for him. Dawes felt comfortable in his masculinity to wear a lingerie set, and why should women be the only ones to dress sexy?

Their day at the mall came to an end, as Colette and Dawes set up a date to exchange gifts before Dawes left to see family out of town. A few days later, Dawes, gift in hand, knocked at Colette’s apartment door. With a smile, she opened it, expressing surprise at Dawe’s wrapping and inviting him inside. Eagerly, Colette opened up her present and hugged Dawes for his gift. Dawes didn’t expect anything big in return, so when she handed him a box, Dawes eagerly opened it.

When the tape on the box split, Dawe’s life would change. Inside, he pulled out a plastic bag containing the red lingerie set he’d been gawking at a few days previously. Dawe’s stomach dropped, his breath shallow, his heart beating rapidly. This was the test to see if all those words he’d said about being comfortable with his masculinity were true, or if they were merely lies.

Dawes held up the lingerie set, taking it out of the plastic bag, his eyes getting wider as he looked at the beautiful set. He ran his fingers through the lace, the soft, textured fabric giving him goosebumps as he took it in. For years, he always gifted, never received lingerie, and now Colette had fulfilled a secret wish for him. Dawes felt conflicted, he really wanted to wear it to feel feminine and have a slight taste of the feminine experience. But he was nervous about the outward appearance of accepting and knowingly wearing lingerie. What would Colette think? What would future girlfriends think? Would they like it too, or would they judge him? Dawes took a deep breath, taking in the whirlwind of emotions. Why give their opinions weight?

“Go try it on,” Colette said, happily. She pointed to the bathroom.

Without hesitation, and perhaps too quickly, Dawes bolted to the bathroom with the box, locking the door behind him. He looked at himself in the mirror, heart still beating against his chest, like a part of him wanting to be free from the expectations and opinions of others. Dawes knew what he had to do. He threw off his shirt, unbuckled his belt, and dropped his pants, casting his masculine clothes aside. He was going to do it. And if he looked ridiculous at least, he could say he tried something he always wanted to.

First, he slid the red lacey panties up his legs. The lace seductively rubbed against the inside of his thighs, causing chills through his body and a bit of excitement. He pulled the pair up to above his waist, adjusting his junk, and tucking them between his thighs. Dawes admired himself in the mirror, running his hands on the lace, and enjoying the feeling against his body and hands.

Next, he unwrapped the bra and placed it against his chest. Dawes hadn’t worn a bra since his teenage cross-dressing years and didn’t remember how to put one on. He brought them back to the front of his chest, fumbling to connect the hooks as excitement coursed through his body. Finally, locking the clasps in place, Dawes pulled the bra around and put his arms through the straps, sliding into place. He liked the way it hugged his chest, and Dawes admired himself in the mirror, spinning around to see every angle his neck would allow him to turn and see. He felt undoubtedly feminine, sexy, and excited.

When he moved the box from the counter, he heard a rattling sound. Confused, he looked inside and saw a red collar. With Dawes' confidence sky high, his face turned a matching red to the lingerie as he looked at it. It matched the set, and why not? Adjusting the side, he put the collar around his neck, enjoying the restrictive and submissive feeling it provided as the leash fell down his chest.

Dawes smiled at the person he saw in the mirror, confident, sexy, embracing parts of him he never thought existed until recently. He was comfortable with himself and admitted he was a straight man who liked wearing lingerie. It was rare to have supportive friends like this, and Dawes was blessed and grateful for Colette. Taking a deep breath, he unlocked the door, stepping into the living room to hear her reaction, feeling more confident and sexier than he had ever felt before in his life.