A Sissy's Journey Ch. 04

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.

*****

PART FOUR

Finally, another weekend! Had it really been a week since he had been fucked by Amanda? To Jesse, it seemed like it had only been a day or two. But then, almost constantly playing it all back in his mind's eye probably had some influence on his memory. He loved recalling every word said, every smell, every feeling. He still got hard every time he dreamed of the pink lace and satin. And for several days now he had been feeling a pent up need to be wearing those lovely things again.

Sitting alone in his apartment after the end of the work day, Jesse contemplated texting Amanda. For some reason he felt awkward and didn't want to come off as needy. Rick wouldn't be around until later after he closed his shop. Sitting there with his phone in his hand absently thinking, he almost jumped out of his skin when the thing buzzed in his palm. It was Amanda.

"Hi, I was just thinking about you," Jesse said with a smile in his voice.

"Hmm, I guess that means we're thinking the same things then," came the sultry reply.

"Oh, I couldn't possibly try to guess what you are thinking," Jesse replied jokingly but there was also a lot of truth behind the words. How could anyone know what she might think of next?

"Do you want a hint?"

Sure, I love a guessing game," came Jesse's playful quip.

"Okay. What's hard and soft and oh so nice," she shot back thinking it was pretty good for an off the cuff hint.

"I'm embarrassed to say what first comes to mind," he answered truthfully.

"Remember what we said last time, no more secrets. Remember that?" Her voice an odd mixture of softness and ice.

"Yes, I remember. So, those hints remind me of lace and satin for the soft part, and the hard part makes me think of your cock," and as the words left his lips he could feel his arousal. Was it the memories, or the fact he was saying these things to a girl, or was it the tinge of embarrassment he felt in saying them at all? Jesse really had no idea except to decide it was all of these, and it felt really good.

"Well, that was a very good guess. Makes me wonder if you were able to solve the riddle so fast because you were already thinking about the same things," damn, she did it again! With just a few words she could make him feel so exposed.

"Hello, are you still there," came her joking voice when he had become lost in thought.

"Yeah, I hear. And you were right, I was just reliving our last little experience with hard and soft things when you called," Jesse answered honestly.

"Well, I have been thinking of it every day and every night as I lay in my bed all alone," Amanda told him, dropping the jest. "Wanna come over later?"

"Sure, I was going to call Rick later but he doesn't get home for a couple of hours. So is now a good time?"

"Yeah, grab a pizza or something on the way, okay," she answered getting up and heading toward the shower.

"Be there in thirty of forty minutes then, see ya," hanging up the call.

*****

Jesse didn't know it, but he was correct in believing it was impossible to predict what Amanda might be thinking. And in fact, she was thinking this very moment about an idea that had kept fluttering in and out of her head all week. Now she had a pretty good plan to make it a reality. Humming contentedly as she scrubbed her body, she worked out a few last details in her mind.

Drying off and getting dressed, she also rummaged around and found the things Jesse would need to be wearing later. He had liked the pink, but tonight perhaps a plum purple ensemble would be cute. Finding the matching garter belt in the bottom of the drawer convinced her of her choice. Now, stockings. Digging some more, she found nothing to match in color, but did find some old fishnets she had forgotten about. Laying it all on the bed she was satisfied. She wanted him to look as good as possible tonight. He would be thankful later, she was certain.

The doorbell surprised her, but looking at the clock she realized it must be Jesse already. Throwing a robe over her partially dressed body she ran to the door and let him in.

"That was fast," she said as Jesse entered with pizza and beer.

Glancing at the time he said, "I told you thirty or forty minutes. It's been forty-five."

"Oh, I've been busy getting cleaned up," she replied turning to finish getting dressed. "Just put all that in the kitchen and I'll be right out."

When Amanda returned she found Jesse in the kitchen eating pizza and drinking a beer. She knew from the look on his face that the silk kimono she was wearing had been well received.

"Wow, nice dress," he said around a mouthful of pizza. Swallowing he added, "That is so sexy. It looks like it would feel wonderful to wear."

"Thank you, I've been wearing them for over a year now and I'm hooked. I have quite a few and maybe later you'd like to try one on," so far everything was going just as she had hoped.

"Ah, yeah...that might be fun," Jesse replied trying to sound casual. But had he been paying attention to her face he would have noticed the small smirk of satisfaction.

"But first let's eat! I'm starved," she said as she served up pizza for them both.

As Jesse was finishing up the last piece, Amanda casually asked if he had showered after work.

"No, just got home when you called," he replied.

"Well, I think you would feel a lot nicer in one of these if you were clean and smelled nice," she said in a suggestive way as she let her hands run up and down her silk clad body.

"Sounds good to me," he replied honestly.

"Well, as soon as you quit stuffing yourself we can go do that."

"Oh, I didn't know you were talking about both of us in the shower. I think I'm full enough, so let's go get clean!"

"No silly. I've already bathed, but I'll help you do it right," she said with a smile and a wink.

That still sounded like a pretty good deal to Jesse. So as she led the way, he walked behind her and admired the gracefulness the long kimono added to her step. He also acknowledged to himself how quickly he had jumped at the chance to repeat the dressing up experience of last weekend. It felt good being more relaxed about his kink this time. The shock was gone, but the lingering naughtiness of it all supercharged his anticipation of more.

"Okay, strip," Amanda said in a way that wasn't a command but very close to one.

As she leaned against the vanity watching, Jesse did feel like a stripper removing his clothes for her. Finally nude, he stood as if for some inspection, feeling his nipples harden from the cool air. His dick was also beginning to awaken. He felt even more naked than he was as he watched her face while she casually took in every detail of his nakedness. The fact that she was still fully dressed wasn't missed on him and he wondered why it made him feel so vulnerable.

"You need to do a little shaving I think," was he assessment. No word or indication that she found him desirable. No indication she was hungry for his body. And he felt a shudder emanate from his groin at being treated this way.

"You're lucky that there is so little hair on your body. Not a hair on your chest and barely a hair on your legs, that's amazing," she said as she ran her fingers over his nipples admiring their pert fullness. "Lift your arms. Hmm, not much there either. I've seen you crack already, and we need to shave that a little. And I think you would look nice with just a small landing strip up from you clitty. Oops, did I say clitty? I mean your little dicky," and again the sweet little smile that announced how much she enjoyed teasing him.

The warm shower itself felt wonderful and so relaxing after a long week. Once the time came for the shaving though, he wasn't so relaxed. Amanda was quite expert in the shaving itself, but being further feminized by her hand brought a powerful sexual connection to the simple act. She left his ass and balls to the last, and with a simple instruction to turn around and bend over Jesse felt he was taking another of those steps into an unknown land.

"Okay, you need to spread your butt for me again, and hold it open...and be still, for goodness sake!"

Easy for her to say, he thought as the razor flirted around some very delicate places. He was thinking that maybe this wasn't such a good idea just as the cool metal touched his tightly contracted balls! By the time it was over he was a little more relaxed, but not much.

"There, that's much better," came the satisfied voice behind him. "Let's just give it all a good rinse now," just as he felt the handheld shower stream hit him between the legs. "Okay, you feel everywhere and make sure I got it nice and smooth," she suggested.

As Jesse rubbed his hand over all the places the razor had visited, he was amazed at how good it all felt. So much more sensitive and the smoothness was wonderful, he thought.

"Satisfied," she asked.

"Oh yes, very satisfied," was all he could think to say.

"Good, hop out and let's get a better look."

As Amanda dried his wet body, Jesse could get a good look at her work in the mirror. What a difference it made. He had admired the look of so many smooth hairless sissies on the photo-sharing sites he visited, and now she had helped him to look just like them.

"Not bad, eh?"

"I love it," he replied. "Thank you so much for doing this for me," he said as he hugged her.

"Okay, one more thing before we get you dressed," she said while opening a container of body lotion that was her favorite fragrance. "Hold out your hand," she told him and then poured some of the silky liquid into his palm. "Now you can spread it over your body. It'll make your skin soft and smell good. Turn around and I'll do your back."

Finally satisfied Amanda took his hand and led him toward her bedroom. When Jesse saw the things she had laid out for him, he was dumbfounded. Everything was so beautiful and elegant. She had laid them all out neatly like a display in an upscale shop. Jesse had never felt so pampered and catered to.

"Well, I think I must have chosen well, from the look on your face," she said in an attempt to rouse him from his stupor.

"It's all so wonderful. I couldn't have ever done this without you," he said with no self editing of his thoughts. His nudity forgotten, he turned and embraced her in sincere gratitude. Amanda enjoyed the closeness as much as he did, and was captivated by his clean feminine smell and childlike trust. Oh yes, she could really get used to this, she thought, closing her eyes and laying her face against his bare skin.

"Come on, let's get you dressed baby. I know you're going to love these things." And like two close friends sharing clothes she taught him how to make himself even more beautiful with the sexy things girls get to wear.

This time, the garter belt and fishnet stockings were the highlight of his new experiences. That is, until she helped him into the kimono. Tying the sash for him, she turned him to the full length mirror and asked, "Well, how do you like it?"

"I can't believe how wonderful this all is," he said while running his fingers over the silken gown and turning to see every angle.

"Would you mind if I just put a tiny bit of blush on your cheeks," she asked as a last minute thought.

"You mean some make-up?"

"Just a little, to give you a more finished look. You'll like it, trust me," she said softly.

"Okay, why not?"

And she did just apply a light bit of makeup in a skillful experienced way. It was the perfect touch to enhance his beauty while not being overly noticeable.

"Now take a look," she said turning him back to the mirror.

All Jesse could think was that he finally looked perfect. He could never go back to having this part of himself be caged and locked away. He didn't even want to think about any details of what that might mean, he just knew it had to be.

"Sweetie, I can see how much this means to you, and all I can say is this is just a beginning. I haven't done anything to your eyes, and your hair is a complete disaster. Not to mention your hands and nails. But we can do so much more than you see now," the sincere love she felt for him was clear in her voice.

"How about a touch of lip gloss, do you think it would look okay?" The question clearly showing he was ready to take her at her word.

"That's a great idea, how could I have missed that? What color, I think a light pink," she rambled while rummaging in her makeup drawer. Then, once again, a very modest application of a pretty pink that gave just a hint at what might one day be possible.

*****

Sitting in the living room sipping beer, Amanda led Jesse into a conversation of mostly chit chat. Her plan was about to be engaged and she wanted him eager for her suggestion. Ever so subtly she turned the conversation back to more intimate subjects by asking, "How does the kimono feel?"

"It feels so smooth and comfortable. If I would have known how nice this was going to be I would have let you dress me sooner," Jesse answered honestly.

"I like the way you're sitting up straighter and have your legs together, but we're going to have to get you some shoes soon. Maybe some sandals like mine that match your dress," she suggested holding her feet up for him to see.

"I was kinda thinking the same thing. I noticed yours match the style of the kimono really well."

"I could paint your nails, if you'd like. I think it would help your feet match the rest of your outfit. I can do them in this color I'm wearing and it would be fun," she urged him playfully.

"Okay, why not. I've gone this far, so I might as well try that too," Jesse said enjoying the kidding around.

It took longer than she had thought to get the fishnets off, clean up his feet and shape his nails. After half an hour Amanda said to him in a stern tone, "You better start taking care of your feet if you want me to help you be pretty. This is kind of disgusting, how can you let you nails grow so long? And don't you ever scrub the dead skin away in the tub?

"I guess I never thought about it much and didn't know how. But I'll take better care of them, I promise," and he meant it too. This whole experience was very enjoyable and very erotic.

Once the pale pink polish was on all of his toes, they both sat back and admired Amanda's work. His feet had taken on an entirely different gracefulness, a sophistication that fascinated her. Jesse was equally pleased, but his admiration of the transformation was accompanied by an undeniable arousal that was making his panties not fit as well as before.

"That looks so great. Thank you for all that work," he said giving her a hug.

"You have to sit still for awhile until it all dries. If you mess it up, you'll have to redo it yourself," she warned him.

"I'll get us another beer and you can sit at let them dry, but from now on I think it should be you waiting on me after all I have done for you. I think I would like having a geisha in a kimono serving me. Don't you think that would be fair," she asked seductively as she stood above him and tipped his chin up with her hand.

"I guess fair is fair, and I couldn't have ever done this on my own," he replied not really knowing what else to say.

And he wasn't at all opposed to serving her, it really did seem the thing to do for some reason. In this new world he was in, she was the one who knew what to do and he was following her lead.

"Good, then it's agreed. Like I said before, there are still a lot of things we need to do before we're done," she said and turned to get the beers.

With the beers finished and Jesse's nail polish dried, both we're feeling loose and uninhibited. Amanda coached him a little on how to walk more gracefully, and they both laughed at his clumsiness. Putting on some music, Amanda slid her arms around him and they slowly danced in the living room. When she lowered a hand to his bottom and rubbed over the soft material, gently tracing a finger along his crack, Jesse just let himself be absorbed into her as she led him around the room. Stopping, and with eyes locked on each other, Amanda pulled his lips closer into a kiss. Pushing him up against the wall, she pressed her kiss harder into his. When her hand found his cock he subconsciously, and very slightly, spread his legs for her. In that moment Amanda wished with all her pent up need that she had a real cock to stick into his pussy!

Breaking away and recollecting herself, she said, "We're going to mess up our makeup if we keep this up. And I have another idea; What do you think about contacting Rick and he can see for himself how pretty you can be?"

Thinking for a moment Jesse felt both and eagerness and an apprehension about exposing himself to Rick. Amanda, sensing his conflict reminded him, "He already knows you're doing this and he encouraged you, right? And he even said he would like to put you in panties. Why not let him see now while you look so hot?"

She was right again, as usual. So pushing his conflict aside he agreed.

"Do you think Rick would be around if you called him?"

Jesse thought for a second and replied, "Probably."

"Goodie," she said going to retrieve the laptop.

Amanda hadn't mentioned the full reason she suggested contacting Rick. Yes, it would be fun and also good for Jesse to show him that he obeyed Rick about the panties. But Amanda was thinking ahead too, so she carefully took note of the contact path that Jesse followed in getting Rick online. While Jesse was trying to get Rick up to speed about why he called and where he was, Amanda made a tidy note of how to contact Rick later when she was alone.

When she returned her attention to Jesse and his conversation, it was just at the moment that Rick asked to see what Jesse had been describing. Looking at Amanda, he asked, "Is it okay if I turn on the cam?

"Of course, silly. That's the whole idea, isn't it," but it was with a smile of affection that she said it.

"Hi, can you see me okay," Jesse asked when Rick's familiar face filled the screen.

"Sure can sweetie, I can see that your face is prettier than the last time I saw you. But did you ever find those panties you were telling me about?" Rick said in his usual bantering way.

"Yes, I'm at Amanda's place now, she's here too. Do you mind," he asked to be sure Rick didn't mind bringing another person into their conversation.

"No, I can't wait to meet the lovely lady who is getting you to think straight."

Rick continued watching as Amanda's living room jiggled and jumped around on the screen. He smiled as Jesse appeared and then disappeared, obviously struggling to get the camera to a better vantage point.

Grabbing the computer before it fell off the sofa, Amanda came into the screen and said, "Hi, I'm Jesse's friend."

Rick momentarily forgot about Jesse and his struggles with the panties and focused his attention to the perfect face framed by locks of hair that trailed out of view. He also noted, with a little envy of Jesse, the graceful neck leading down to a silk gown of some quality.

"Hello, Jesse's friend. I assume your name is Amanda?"

Was she blushing? Amanda was taken aback by Rick's masculine beauty, the fact that he also was almost nude on the bed only intensified that truth.

"Oh, yes I'm Amanda," she finally blurted out.

"Nice to meet you Amanda, Jesse has mentioned you but held back the details of your beauty."

Oh my, it was easy to see why Jesse was taken with this guy, she thought as she enjoyed the view.