A Sissy's Journey Ch. 05

Finally, the two girls forced a pause in their explorations, and turning again to Jesse found him naked and tugging at his little cock. As Briana worked at getting the last of her tangled clothes off, Amanda approached Jesse and forcefully kissed his mouth while pushing her tongue between his lips. As he was sucking on her tongue, she pulled away and said, "Here, suck this," putting the two fingers covered with Briana's juices between his lips. Jesse eagerly complied and relished both the taste of Briana's pussy and Amanda's confidence.

"Okay, you're the only one wearing clothes," Briana's voice crowded into the silence of the other two lovers minds.

Amanda felt soft hands working at the tie that held her sweat pants tight. Then, like sliding sand they slid down her legs into a heap around her ankles. Not wearing panties, Amanda's perfect ass was too much for Briana to resist as she went to her knees to lovingly kiss the soft flesh. In that position, it was too much to resist further exploration and a soft hand found it's way up between her lover's legs and into the moist folds that hid there.

It was Amanda, as usual, who took control and stopped the passion that was close to evolving into an orgy. "Okay,"she said while pulling her fingers away from Jesse mouth, "We're in here to get cleaned up, remember?"

"You started it," Briana was quick to point out.

Amanda turned and said playfully, "Don't you get sassy with me little Missy." And to make the point, gave a little tap on top of Briana's head as she knelt looking up at her.

"Yes, Mistress," Brianna replied meekly, hinting at a deeper relationship that Jesse was unaware of.

With that the three returned to the pleasurable task of getting Jesse cleaned and groomed as the first step of making him look as much like a girl as possible. That the task required that all three needed to be in the shower together only made the chore more memorable.

*****

After the shower, the sexual energy that flowed between the three friends was almost palpable. But forcing the trio to stay focused, Amanda started by rubbing a pleasant scented coconut oil over every square inch of Jesse's body. Before that was finished, all three of the perfect young bodies had been anointed with the fragrant oil.

"Remember, you need to always use moisturizer after every shower. If you don't you won't have soft skin, understand," Amanda coached, as she cupped Jesse's cock and balls firmly rubbing in the last of the soothing oil.

When Jesse just nodded his head yes, Amanda said, "Here, take this bottle with you so you'll know what to buy when you run out. We'll make a little bag of stuff we use today so you can start getting the hang of it on your own."

With the body moisturizer on, Amanda selected another pair of panties for him to wear. She decided on a pink lace pair with a small red bow on the front. Then rummaging deeper in her drawer, she finally found the pink strapless bra she seldom wore and added that to the pile on the bed. As an afterthought, she rummaged out a couple of pair of old panties to stuff the bra.

"Okay, put the panties on so you won't be sticking out so much down there," Amanda said pointing at the hard cock that showed no signs of going away. Jesse felt the humor in the situation and giggled along with Briana at his condition.

"That's better, now sit down and lets see how you've been doing on your feet," Amanda said.

Satisfied that he had been keeping his nails trimmed and shaped Amanda asked Briana what color she thought would be best.

"Oh, I can't decide until we select the dress," she answered.

"Good point," Amanda replied going to the closet.

Jess pipped in saying,"Would you mind if I borrowed the kimono I wore for Rick last time? I think he really liked it, and he said last night we should meet for dinner or something today. I'll be careful with it...I promise," Jesse felt a little pushy but was hoping she would agree.

"What did you just say? That you have a date planned and didn't think to mention that to us! When is all of this supposed to happen," Amanda asked incredulously.

"Well, he mentioned maybe meet for dinner," Jesse said meekly.

Glancing at the clock, Amanda said, "Well it's already after noon now. Do you think maybe you should give him a call and settle on a time? You can't just expect him to hang around all day waiting for you to call. You do know that's a real good way to drive him away, don't you?"

Somewhat stunned, he felt a slight panic when he realized the significance of the question.

"Don't tell me you're still waffling and haven't even agreed to a date yet!"

"Well, I guess maybe I was waiting to get better at looking pretty," Jesse replied in a meek small voice.

"Why don't you call him right now and ask him if he's busy tonight. I would hate to think all of this work getting you to look so beautiful is just going to waste," Amanda said.

"I agree," Brianna chimed in. "It's Saturday and a perfect time to finally jump in and see if you really like him enough to keep going on with him. Plus, he won't wait around for you forever, you know."

Jesse knew deep down they were right. He just felt those terrible first date jitters, only this was worse because he was talking about going out with another man...and dressed as a girl. But when Amanda put her phone in his hand he took the plunge and dialed Rick to ask him out on a date. The two girls discreetly left the bedroom while he waited for Rick to answer.

"Hi Amanda," Rick replied seeing the caller identification on his phone.

"Ah hi. It's actually Jesse. I'm at Amanda's on her phone," he explained.

"Oh, hi sweetie. I'm glad you called," Rick replied.

"Yeah, I'm over here doing what you suggested. I'm here with Amanda and another old friend getting all dolled up. Anyway, um...they thought I should call you and see what you're doing tonight...like maybe we should meet or something," the awkwardness was worse than even Jesse had imagined it would be, but Rick was quietly chuckling to himself as his sweet young friend struggled to find the right words.

"Well, it just so happens that I have absolutely nothing planned for tonight and would love to go out with you," Rick answered quickly in order to end Jesse's misery.

Rick could hear the big sigh of relief before Jesse answered, "That sounds great! Where should we meet?"

"You're at Amanda's now, so why don't you give me a time and her address then I'll pick you up and surprise you with dinner someplace," Rick suggested, knowing it would make it all easier.

That's a great idea," Jesse agreed. "Let me go ask the girls how long they think it'll take to finished getting ready and I'll be right back."

Rick could only hear the muted conversation of the girls and smiled as he imagined the scene he was unable to see.

"Okay," came the somewhat excited voice of Jesse, "Can you pick me up around six this evening?" But before Rick could respond he heard a woman's voice saying something to Jesse, and then "Hey Rick, Amanda wants to know where we're going so she can pick out a dress for me."

"Six o'clock works for me, and tell Amanda upscale but casual should work for the dress," Rick replied with a slight chuckle. And after getting the details of Amanda's address the two said goodbye until later.

"Okay, he'll pick me up here at six o'clock tonight. He wants to take me to a restaurant downtown and he said to tell you it is upscale but casual," Jesse told the girls.

"Okay, that helps and should give us plenty of time," Amanda replied, "But the kimono you wanted won't work, it would be over the top and make you stand out too much. I think a simple black mid-length would be perfect, what do you think Bri?"

"I agree, simple but elegant," Brianna replied.

"Okay then, back to the toenail polish. What color of nail polish do you think," Amanda asked once all the clothes were figured out.

"Hmm, I would say either black, pink or bright red," Brianna quickly replied but then added, "Or maybe all three. Like a light pink base with a red rose and black stem on each big toe."

And so it was agreed, and Brianna did a masterful job while Amanda started to try and make some sense out the the tangled mess that was Jesse's hair. After the better part of an hour had passed, both hair and toenails had been transformed into something very beautiful. His hair wasn't fully grown out yet, but it was long enough to work into a boyish bob style with just a little shaping.

Jesse had not only been in a wonderful state of bliss during this work over, he was also paying close attention to both of his friends as they worked there magic on him. It wouldn't be as good, he admitted to himself, but he thought he could do an adequate job on his own the next time.

Amanda and Brianna were like two school girls giggling and asking all the important questions. It went unnoticed to them all how easily Jesse fit into all of the girlish energy as the trio continued the beauty make-over that had been briefly interrupted.

"Now, what next," Briana asked, while Jesse sat in panties admiring his painted toes waiting for them to decide what to do next.

"I think since Jesse is going out we should also get his fingernails cleaned up. Bri, would you be sweet and drive up to the market and pick up some press-on nails," Amanda asked after deciding that the nails were a must.

"Sure, be back in a flash," Brianna said, then "call me if you think of anything else," Bri shouted on her way out.

"Okay, now I think what we should do while Bri is gone is to get your pussy cleaned out good...just in case things get interesting later," Amanda counseled wisely. Jesse hadn't even thought about it, but agreed with the wisdom of the suggestion. So with no hesitation he followed Amanda back into the bathroom to douche his pussy squeaky clean just in case this date turned into something more. It was while he was walking down the hall that he realized that he had just used the word pussy in his mind's description of what he was about to do. Oddly, he felt comfortable with that and smiled a little smile to himself.

His reflections about his pussy were interrupted when Amanda said, "Be careful of you toenail polish Jesse, it's not hard yet!"

Brianna returned shortly after Jesse was finished and found the two waiting for her in the bedroom. In a short time the fingernails were on, shaped to a tasteful size and polished the same light pink that Jesse had worn the first time he modeled for Rick. Now it was time for a more serious effort with facial makeup.

As Brianna applied a foundation layer, Amanda was gathering the other necessary items to transform this pretty young man into a beautiful young woman. Unfortunately for Jesse the array of items included tweezers to make a few minor corrections to his eyebrows. But once they were trimmed and shaped, Jesse could easily see that the minor pain had been worthwhile. And after Briana worked some magic with liner and a small brush the image he saw in the mirror already looked more feminine!

"Okay, now the eyes," Briana announced.

"What color do you think Manda," Briana asked.

"I don't know, you're better at this that I am. What do you think?"

As the two discussed this apparently important question, Jesse admired what they had already accomplished. He was even more convinced he had made the right choice in pushing forward in this because he loved what he saw in the mirror, and more importantly he loved how he felt in the deepest part of his being. His little clitty apparently agreed because it was pressing hard against the pink lace panties again, and in that moment Jesse decided he liked the term clitty better than dick or cock because it just sounded right.

"Okay, we both think that you should go with a modest look for tonight. Basically we think a little brown eye-shadow and some highlights will do it...and of coarse some mascara to lengthen the lashes. And then this shade of lip gloss," Brianna said while holding the light red lip gloss out for his inspection.

Amanda chimed in, "Don't forget a little pink blush, Bri."

Feeling at ease and enjoying all the attention, Jesse playfully said, "That's pretty much what I was thinking too."

They all laughed, and Amanda said, "You just wait until you have to make all these decisions for yourself. You'll be begging us for help and we just might be too busy!"

"Okay, I admit I'm at your mercy. Does that make you feel better," Jesse asked smiling up at the two girls.

"I don't know about you Bri, but I like the sound of him being at our mercy. Don't you," Amanda teased.

"I think I do too," Briana answered. Then reaching her hand to Jesse's aroused clitty she added, "And to be honest, I think Jesse likes the sound of it too. Did you notice this sticking up?"

"Yep, I saw it too. He couldn't get that thing working for my pussy, and I know he couldn't for you either, but we all know now that it works just fine under the right conditions. Right Jesse," Amanda teased and then hugged the slender young figure who was also enjoying the fun.

"You're both right. I can't tell you how ashamed I have felt because of how I handled all of that. But now we all know more than we did before and you have to know how much I love both of you for all you have done for me," Jesse answered in a rush of words and emotion. The three lovers hugged each other in silence for a wonderful moment in time.

"Okay, let's finish this up," Amanda said after she kissed both Briana and Jesse.

With a final effort of artistic skill, Briana shaped and colored Jesse's eyes in a way that any woman would envy and finished with a light pink lip gloss. Briana had always been artistic and very skilled in the art of make-up, so the entire experience had been one of the best in her memory. Like Amanda, she found herself more drawn to Jesse now than when she had assumed he was a regular guy. He had always been so caring and sweet, and now that sweetness could be embraced in a more intimate way than she ever imagined. It was almost like the love she shared with Amanda, and in truth what she now felt was more like a lesbian love.

"Ta-da! Finished, how do you like it, " Briana asked as she stepped away from Jesse.

"Simply amazing," was all Amanda could say.

"Wow, I can't believe that's me," was Jesse's response. "Thank you, I can't thank you enough!"

Amanda stepped to Briana, drew her close and kissed her on the forehead. "Thank you sweetheart, I couldn't have done this like you did."

Jesse loved seeing the two girls like this, the shared loved seemed to overflow into the whole room.

"We'd better get finished, it's getting close to time for Rick to pick you up," Amanda said.

And with that, the shimmery black dress, fishnet hosiery and garter belt, a pair of Amanda's glittery sandals and a small matching purse were all quickly pulled together. Finally, all three girls stood back and approved of the image in the full length mirror in Amanda's room. And they had finished none too soon, and all of them turned at the sound of the door chimes.

"Your date is here Jesse," Amanda teased.

And indeed he was. So Jesse bravely walked toward the next big experience of his young life. But big new experiences had been coming fast and strong these past weeks, and he wasn't as afraid to reach out and embrace the things that once frightened him. In fact, he was feeling quite adventurous and aroused thinking of where this evening might end.

To Be Continued...