tagTransgender & CrossdressersA Sissy's Journey Ch. 05

A Sissy's Journey Ch. 05


This work is authorized by the author exclusively to Literotica.com for publication.

Introduction: A tale told in short vignettes which chronicle one young man's journey into self discovery.

Please Note: This story series contains elements of homosexuality, cross-dressing, light femdom/submission and male feminization. All characters are fictional and portray adults over eighteen years of age.



In the two weeks after his coming-out experience with Rick and Amanda, Jesse experienced a combination of conflicting emotions. One moment he was thrilled with the sensations of freedom and self confidence, but without warning his mood could shift to apprehension and shame regarding the larger implications of embracing his new direction. He was losing interest and connection with some of his old friends who he knew would turn on him for being a cross-dressed fag. But even as his inner voice was directing him away from these old friends, there was another voice urging him to forget all he had discovered with Rick and Amanda. In the end, the decision came down to choosing one way or the other. To be true to his deeper self, or run with the known. So like millions before him, he wrestled with his choices while postponing any real decision.


Bruce had been his friend since High School, but had not chosen college like Jesse had. The friendship had become less important over the years apart, but they still met up on occasion for a night out, so the call didn't surprise Jesse as he answered with , "Hey B-man, what'cha up too?"

"Not much, just wondering if you want to go to the Pussy Cat Club tonight and hang out?"

"Sure, I guess so," Jesse replied without much enthusiasm, then asked, "Do you know what band is playing?"

"Nah, just need to get out and find some pussy and get wasted," Bruce shot back.

Jesse could have guessed Bruce's answer since that was about all Bruce was interested in. Jesse didn't really want to go out with him but didn't quite know how to get out of it. So instead of being honest, Jesse just agreed saying, "Well, that's always been a decent plan."

B-man made an attempt at a witty reply with, "What better plan could there ever be?"

"Okay, when you going to get there," Jesse asked.

"I'll meet you at the bar around eight, we'll grab a table and start the hunt." B-man answered.

"Okay, see you later then," Jesse said and hung-up the phone.

Great, Jesse said to himself. Why did I agree to waste a Friday night with B-man? I already know how this is going to go and it's going to be miserable. The last time we were there we almost got into a fight with three other guys because of B-man's big mouth about fags and queers needing to be strung-up. I don't even have to guess what he would do if he knew about me.

But perhaps it was fate, or just good luck, that B-man had called. The striking comparison of what his life would be like pretending to be like B-man, as opposed to the liberation he had found with Amanda and Rick, worked to solidify his decision of which way to go. And as the seconds passed into minutes the decision became fixed. With both relief and a new resolve, Jesse sent a text to B-man with an excuse why he couldn't make it tonight. When he hit send, it was like Jesse was pushing the flush button on his past. And with that flush, some of the doubts and questioning were once more pushed aside.

As Jesse lay on the bed in blissful peace, another call. But this one was Rick.

Eagerly, Jesse answered with a happy lift in his mood, "Hi there, what's up?"

"Oh, not much yet. Just wanted to touch base since I haven't heard from you in awhile," Rick replied.

"Ye-ah, I guess I've been kinda busy," Jesse answered with a half truth.

"I'll accept that, even though I suspect there's more to it than that. What I really suspect is that you're a little embarrassed about me seeing you dressed up at Amanda's," Rick responded truthfully.

"To be honest, you're right. I've been going nuts trying to figure out what the fuck all this mess is and where it's taking me," Jesse confessed.

"And that's why I really called. I just want you to know that you're experiencing the same thing that every other person before you has felt when discovering their true self isn't quite what they expected. Do you think I have always been the confident man you know? No way. I was just as frightened and unsure as you are right now. But I wanted to call just to let you know it will get better. Some of the people you know will accept you, like Amanda. Others will reject you. I tried to play it both ways and hide in between for years. In the end, I just decided to be me and let the chips fall where they will. I hope you can do that quicker than I did," Rick said out of a deep desire for only the best for his young friend.

"I know what you're saying is right, Rick. I've been fighting it back and forth. But just tonight, I have come to the same conclusion you did. I can't go back, so I have to go forward," Jesse said, then added, "I can already feel the clouds and weights lifting. I'm sure it's not all over, but I really do feel inside that I'm over the worst of it and I'm going to be true to myself," Jesse said and finally felt even more truth in his words.

"Hearing you say that takes a load of worry off my mind, and I can't tell you how relived I am. I'm also really proud of you. It takes a lot of guts to do what you just did. So congratulations, and welcome to the club of the others," Rick said.

"I still sort of wish I was just a normal gay guy though, like you. I mean, it would be easier If I wasn't so different with all the dresses and stuff," Jesse confessed.

"I don't know, I think anyone who steps outside of the rules is going to face a lot of pushback. It wasn't easy at first for me or anyone I've known. And in the end, you just have to discover yourself. Don't look at me or anyone else, look inside yourself and you'll find the truth," Rick replied.

"I know what you're saying is right, but it's still me wearing panties...not you."

"I'm glad you brought that up, because another reason I called is to let you know I haven't been able to stop thinking about how wonderful you looked the other night. I don't want to, or mean to, push you in any direction. But I will be honest and tell you that as far as I'm concerned I would love to see you take your femininity as far as you can. Let's put it this way. If you're weird for wanting to be feminine, then I'm just as weird because my desire is to be with someone like that," Rick sensing the shift in their relationship. No more simple banter and fun, but the beginning of a true honesty that only friends and lovers know.

Jesse felt it too. But he felt it in silence as the tears welled up in his eyes and he was unable to respond. Rick heard the sniffles and allowed Jesse to fully experience this moment of affirmation. Once he sensed that Jesse had recollected himself, Rick said, "I wish I was there with you right this moment. I wish I could hold you and reassure you that it is all right. I wish I could kiss the tears away. All I can do though is to say those things and hope you know my words are true."

"I believe you, and I would give anything to be held by you right now," Jesse replied, with a few more sniffles.

"Perhaps one day real soon," Rick said. "In the meantime, I hope you will let Amanda help you to keep going as far as you feel you want to. She's a one in a million friend, and I think you can trust her with your life. And I mean that."

"I want to. I want to be pretty. I don't understand why, but I know I do. And I plan on letting Amanda know that too. At this point, I think I only have you and her. I've never been so alone, but at the same time I've never felt so loved," Jesse said in a rush of release.

"You are loved...by both of us. So just remember that and you'll be okay," Rick replied.

"I love you both too, you're the best friends I've ever had. I guess I better call Amanda and let her know what we've been taking about. I hope she's up for trying to make me pretty," Jesse said and the lift in his voice reassured Rick that all was better.

"Okay, baby. I have no doubt Amanda is more than willing to take you as far as you want to go. Just remember, it's fun. It's not a life or death situation you're in, even if it feels like it sometime," Rick said as his final boost of encouragement.

"Thanks Rick, I feel like I've known you forever, and I'm really looking forward to meeting you soon. Bye for now,"

Bye Jesse, and call me tomorrow. Maybe we can even meet somewhere for dinner or something." Rick replied.

"Uh, yeah we should do that...I'll give you a call," Jesse answered.

"Okay, call me tomorrow then, bye sweetie."

Jesse sat back and closed his eyes. Wow, he thought to himself, what a ride this has been. But as the adrenaline cleared he felt a deep sense of clear space within his mind where he could stand back as a spectator and scrutinize the different aspects of all he had been experiencing these past weeks. It was as if each question, each mile stone, each emotion could be taken down and held like a globe for a more detailed look. One globe in particular held his attention; Rick. As he pondered his feelings about Rick, the one thing that stood out was the thing called love. Jesse had never been in love, but he acknowledged in that safe space he was exploring, that he felt love for Rick. It wasn't lust, it wasn't friendship, it wasn't respect or admiration. No, it was all of these but more. Yes, it was love...and it felt really nice.

Thankfully, the tears and the stress had finally drained all of the energy from Jesse and he fell asleep with a peaceful heart and thoughts of love.


The one thing Rick had not been fully open about was the fact that he and Amanda had been in contact several times since the evening Jesse had revealed himself dressed in a kimono. It had been Amanda who contacted him one evening. She wasn't overt or obvious, but it wasn't hard for Rick to figure out that Amanda was feeling out his intentions regarding Jesse. It was pretty clear from her veiled questions that she was afraid that Rick only wanted to bed Jesse. More than anything, the questions led Rick to admire and respect her even more than he already did.

"So, I guess this is probably hard for you to know, and maybe it's none of my business, but I think what you've been saying is that you don't really see Jesse as just a casual hook-up," Amanda asked.

"It may have started that way. But, the better I get to know him, no. I would not want to have that be his first introduction into this new life he is discovering. When we first connected in the chat room, I figured he was just a sub bottom on the hunt. But it became clear pretty quick that he was exploring his sexuality," Rick answered in all honesty.

"That really makes me feel better. I have been pretty shocked myself about all of this. At first I thought it was just some joking around, but you're right, he is really in the process of some big changes. Honestly, I never saw it coming. And I've known him almost forever." Amanda confided. "So let me ask you; Are you really interested in him being more feminine or do you think I should steer him away from that?"

Rick hesitated for a moment then answered, "Personally, I would love to see him go further. I am really attracted to feminine men, always have been. I don't know him well enough yet to truly know what his sexuality really is, and I doubt he knows yet either. To be honest, I really only want what's best for him. I'm not one of those who use people for my pleasure. In fact, I try to live my life as best I can without doing any harm to another. So I guess, it's not really about what I would like. I can only say it certainly wouldn't bother me. What do you think?"

"Like I said, I've known him for a long time and even though he kept this hidden from me, now that it's out...I think he really needs to do this. I've watched his face as he looks in the mirror and I've seen how pleased he is. I don't think this is just some kink or passing interest. No, I think he would love to embrace this but he's afraid," Amanda said this while feeling the burden of trying to do the right thing for a friend.

"Okay, so what do you want to do," Rick asked.

"I guess just go forward. I know he wants to learn more about being attractive, so I'll take that as far as he wants to go. And maybe you can just keep reassuring him and letting him know he's okay. I dunno, does that make any sense," Amanda asked.

"Yes. I think it's about all we can do. And hey, I'm really glad you called. I think Jesse's a lucky guy to have you for a friend...and I hope you feel more comfortable now that you now I'm not an old lecher looking to take advantage of a pretty young man," Rick said with a chuckle.

So, even though Jesse was unaware of it, he had two angels watching over him as he traveled the rocky trail of self discovery...


It wasn't until late Saturday morning that Jesse woke up after talking to Rick the night before. Still dressed in his work clothes and feeling terribly ruffled and nasty, he got up and stumbled into the bathroom. After undressing, he sat down to pee. He did this unconsciously since he had been sitting to pee for as long as he could remember. It probably began because it was easier to control his small dick sitting down, but lately he had also experienced a distinct girlish connection in the privacy of the bathroom. It was there, many years ago, that he had found his nipples and the wonderful sensations of pleasure they could give as he pinched them. So as his flow splashed in the water of the toilet, Jesse was enjoying the tingling pleasure flowing from nipple to the base of his cock. Out of habit, he wiped the end of his dick when he finished.

The shower felt wonderful, and Jesse did his best to keep up with the shaving Amanda had done. It was awkward to reach all the right places though, and he thought hair removal might be worth it. But finally satisfied he got out and dried off, then putting a robe on went to make some coffee.

Amanda's call came on the second cup of coffee and Jesse was enthusiastic when he answered, "Hi stranger," he said happily.

"Hi yourself. Why haven't you called me," she asked bluntly.

"Oh, you know...just busy," but Jesse was a terrible liar and it never worked for him.

"That's BS and you know it. So what's been going on?"

"Okay, I've been feeling kinda weird about what we've been doing. I doubt you can understand, but it's not easy for a guy to admit he's into girls clothes and other men. But I'm feeling better today, and I was going to call you. Honest, " he said.

"Hey, I can understand. Don't forget, I had to answer some questions myself the first time I knew I was interested in another girl. But I get it. Just don't go into a shell, that's what friends are for," she said trying to reassure him.

"I know, my bad. Rick called last night too, so I guess I have two friends in the world who actually care about me, and I really appreciate it," Jesse said and felt the warmth of the words.

"So, what did he say?"

"'Well, I was feeling I might be making a mistake in the direction I've been going. But he reassured me I wasn't. I guess I needed him to remind me of who I am. There's still just a little of the old me inside trying to cause trouble I think," Jesse answered. "Anyway, I was going to call you and ask when we can get together a do some more about making me look better?"

"It's Saturday, and I don't have any plans. So you can come over anytime you''re ready," Amanda told him.

"Yeah, let's do that. I'll grab a quick bite and be over in an hour or so. I've done what you said and let my hair grow out. It's not as long as it needs to be, but maybe you can do something with it. Do I need to pick up anything on the way?"

"No, I can't think of anything. See you later then," she replied and hung up the phone.


When Jesse arrived at Amanda's he was surprised to see Briana there. At first he was confused, but assumed she had just dropped by unannounced. Jesse hadn't seen her in over a year, and the last time was when they broke up. He remembered the shame he felt because he had been unable to stay hard while trying to make love...just like he had with Amanda. The breakup had been difficult on them both since it was almost a first love kind of relationship. But unlike with Amanda, Jesse had left with her blaming herself for not being attractive enough for him to stay aroused.

"Hi Briana," Jesse said a bit awkwardly.

Briana came close and gave him a warm hug, then looking eye to eye said, "Amanda has told me everything, and I just want you to know I understand. I wish you would have just told me, but I guess it wasn't the right time. Anyway, I want you to know I'm with you all the way. I never wanted to loose you as a friend, it just felt awkward for us both, I think."

Jesse didn't know whether to be happy or angry. Of course he was glad to have Briana back as a close friend, but why would Amanda betray him to her, he wondered.

Turing to Amanda, she beat him to the question saying, "I know what you're thinking. I told her our secret because I now need to tell you the secret Briana and I have kept from you. Remember when I told you I have made love to other girls? Well, the other girl is Breana and we both wanted you to know that. That makes it okay, doesn't it? For us all to be open with each other is the best, right?"

Jesse had never imagined Amanda and Briana being lovers, so he just stared at Amanda for a silent moment before answering, "I guess so. I'm glad to have Briana back into my life and you had to tell one of us about the other first, so I can understand. Yeah, I'm good."

Briana wrapped her arms him and hugged him tight saying, "I'm so relived to hear you say that. I've really missed our friendship, and now we can be friends without worrying about all the rest. Do you mind if I help Amanda with your transition? She asked me if I would help, but it's your decision, of course."

"What the heck, I don't mind. We've all seen each other naked and we've all had sex together at some point. So it seems silly to be shy now, don't you think," Jesse said.

Both girls agreed simultaneously, and everyone laughed.

"Well, we might as well get started then," Amanda said.

"Where should we start," Jesse asked.

"Girls always start in the shower Jesse, you should know that by now," came the quick reply from Amanda.

"But I just showered a couple of hours ago," Jesse protested

"Not good enough, I'm sure. I did tell you how grungy he was the first time, didn't I," Amanda asked Briana with a smile.

"I think you mentioned that, yes," came the sweet reply.

"Turing to Jesse, Amanda said, "You know the routine." And to make sure, she pointed toward the bathroom.

So off they went to begin the final push toward Jesse's transformation. A happy trio of girlish energy tempered with just a dash of the unknown walking in between the two girls. Once there, Amanda took charge and started with pulling Briana's tee-shirt off. Jesse watched enraptured as the two kissed while Amanda explored the small mounds and erect nipples. With one hand she deftly unbuttoned Briana's jeans and slipped her hand into the pale blue panties. Briana laid her head back against the cabinet door as Amanda's kisses traced a path down her neck and settled on an awakened nipple. Jesse felt the need to strip naked and did so while watching Amanda finger fuck his old girlfriend. In his mind were thoughts of Amanda telling him she had fucked another girl with the same dildo she had used on him. It was now amazingly easy for him to picture all of that as he watched their passion blossom into lustful desire.

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