A Sissy's Journey Ch. 03

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.

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PART 3

Amanda lay quietly watching as Jesse slept in. Thankfully it was Saturday and there was no reason to awaken him. Last night had been another most unusual experience, but Amanda was beginning to better understand the real Jesse. In the shower together before going to bed, she realized as she watched him bathe that he really was a different kind of man. He was more delicate than she had ever noticed, almost like a very athletic female might look. And the little cock was rather delicate, cute would be a better description. It was unfair to expect him to be something he couldn't be, so in that quiet moment she resolved to do her best to help her old friend in any way she could.

Stirring, Jesse woke up wondering for the briefest moment where he was. He had slept more soundly than usual and felt very cozy. The fog began to lift as he remembered the last thing he did the night before, and feeling himself under the covers accepted that it wasn't a dream he was dressed in a pink nightie and matching lace panties.

"Good morning sleepyhead," Amanda said in a voice just above a whisper.

Slowly opening his eyes, he took in the sunshine filtering through closed blinds, lighting the tidy room with a soft filtered glow. He noticed the colorful curtains and the confusing array of bottles and jewelry on the small table next to the window. The mirror on the table reflected back the image of the bed and blankets he was nestled into, a pretty floral design of bright colors. Smelling the fragrant sheets and realizing just how different this was from his own room, he wished he could wake up like this every morning.

Rolling to face Amanda, the two smiled. "How are you feeling today," Amanda asked softly.

"Really rested. This bed is wonderful," and moving closer embraced her in a good morning snuggle.

It was then that he fully noticed again the silky smoothness of the night clothes Amanda had insisted he wear. He enjoyed the softness of them on his skin and the way they felt pressed against Amanda's nude body.

Amanda also noticed the pleasant softness and acknowledged to herself the arousal it caused. Reaching her hand under the covers, she gently rubbed Jesse between his legs. The contrast of silken panties and his compact cock was something she knew she could get used to. Her mind went to other panties she had touched like this, but there had been no fullness pushing back in those, just the warmth of another girl. She decided she liked the way panties felt both ways, and quietly giggled at her selfishness.

"What are you so happy about," Jesse asked smiling, joining in her happy mood.

"Oh, nothing really. Just thinking how nice it is to feel you in my panties and some of the other things I like"

"Like what? Tell me what you like." Jesse was so relieved that she didn't appear to regret last night.

"Well, I was just thinking that I have touched panties with a girl in them, I have touched jockstraps with huge cock in them, I've touched myself in panties and now I have touched panties with you in them," emphasizing the last with a playful grip on Jesse's crotch.

Fully awake now, Jesse quickly responded with, "And which one did you like the best?"

Amanda noticing that he was clearly waking up in more ways than one, if her hand on his panties was a true guide, responded truthfully, "I like them all, but for different reasons."

"I'm really glad to hear you say that. I was wondering how we would feel this morning," the ending sounding like a question wanting to be asked.

"Oh silly, you don't know half the kinky things I like," pulling him close again for another hug.

"You said you have touched jockstraps with huge cocks in them. I have always wondered what it would feel like." Another veiled, yet unasked question.

Amanda figured this was as good a time as any to explain to him about true men. So, cuddling up closer she began with, "Well, it's a lot different than when you touch yourself. I have touched you, so I know what you feel like. When I touch a truly hung man, there is obviously a much bigger hand full. But there are more subtle things too. The heat and weight are so exciting, they tell you he his virile and powerful. Those large heavy balls makes a girl think of his giant load of cum shooting into her. A true stud's cock has a big fat swollen head that just calls to a woman who knows how it will feel inside of her pussy. It's hard to describe, but they just feel so powerful. Wow! I'm getting myself all wet and turned on."

Instinctively she reached to Jesse's cock and was not really surprised at the erection she found there, and the clear difference from what she had just described was even more obvious to her. However, she did muse that she had expected to find him fully hard. Oh, how quickly this kind of honesty was becoming a new normal for both of them.

"So I see you like talking about big cocks in jockstraps too," she teased while patting his tented panties.

Jesse just grinned and pushed himself harder onto her hand.

"Be sweet and go grab my laptop, it's on the desk over there."

Jesse slipped from under the covers and moved toward the corner of the room she had pointed to. As he passed the mirror, the reflection he saw caused him to pause. There he was, all decked in pink satin and lace. He was pleased to notice that he didn't look that terrible, but was startled from his private moment by Amanda asking, "Do you like what you see in the mirror?"

Answering honestly he said in a subdued tone, "Yes, I think I do." But his heart was not nearly as subdued as his voice.

"Turn around and take a peek at the side I'm looking at," Amanda teased.

But Jesse didn't notice the jesting, he just turned and strained to look over his shoulder. What stared back at him was a plump bubble butt clad in delicate pink lace. He instantly thought that it could easily pass as a woman's.

"There's a hand mirror on the dressing table," came a distant female voice.

Too engrossed in seeing himself this way to pretend modesty, Jesse retrieved the mirror and indulged in another look at his bottom. The mirror afforded a much better view, and Jesse was not displeased with what he saw.

"Okay, quit admiring yourself and bring me the computer. I'll show you something you can really admire!"

Jesse abandoned both mirrors and quickly found the computer and handed it to Amanda.

"Okay, crawl back in bed and I'll show you some real cock."

In a quick minute, Amanda had her "Best Cocks" album opened and the two were immediately absorbed in the finest specimens of male virility that Amanda had been able to find and collect.

"Just for fun, pull your panties down and I'll set the computer right here, so you can compare yourself side by side with these guys. You're always asking if you're too small, I'll let you be the judge." There, Amanda thought, that was a good idea and now he'll know.

Scrolling through dozens of images of the most masculine and perfect examples of close up cock, the two huddled together commenting on the pros and cons of the ones that caught their fancy. Amanda occasionally said, "Look at that one...here, put it by yours."

After awhile of the side by side comparison Jesse said, "Wow, you have quite a collection. I've seen some nice ones online but this is the best of the best. My dick looks silly next to them."

But, since this particular silly cock was sticking stiff up into the air, there was no reason for Amanda to ask if he liked the photos. Jesse did nothing to try and hide his interest, and Amanda thought that was encouraging progress.

After at least 20 minutes of looking at the collection, she said, "Okay, that's enough of that for now, I have something else I want to show you."

Rolling over to open the bedside drawer, she returned with a very lifelike dildo. It looked like it could have been molded from one of the jocks they had just been looking at. Handing it to Jesse, she said, "Here. Feel of this. Feel the weight? See how fat it feels? That's as close to the real thing as you can get, so just hold it and close your eyes...and imagine," she said softly.

Jesse was startled from his imagined explorations of real cock by Amanda briskly saying, "Okay, enough of that. Now give it back and I'll stand it up beside yours," as she took the dildo from him.

Once she had it adjusted in place, it looked like he had two cocks. Only one was over twice the length and much fatter than the other

"Well, now you know how others see you. But I want you to know that while most women like the bigger ones, not everyone does. And remember that you're on-line daddy Rick has seen you and he is very attracted to you. I won't say size isn't important, because it would be a lie. I will say that it isn't everything." But with no immediate response from Jesse, she added, "You're really quiet, what'cha thinking?" She knew this was a little bit of a touchy subject, but didn't know how to say it any other way.

"Well, just that I'm kinda pathetic to be honest. I'm thinking I don't ever want another woman to see me naked," and for emphasis pulled the panties back up to cover himself. Then, as an after thought added, "And I'm ashamed of liking these clothes of yours." He wasn't truly angry at these things, it was really just the last valiant effort to resist the inevitable surrender.

But after only a moment he finally offered that capitulation and admitted, "I hear what you're saying, I'm not shocked, I mean I already knew it. I look at these kind of pictures too, so I know." Then after another few seconds, he sighed and added, "I also know I'm turned on by these pics, and I'm turned on by wearing your clothes, I'm turned on by guys like Rick. So, fuck it! I'm tired of trying to pretend to be what I'm not!" Finally the strength of conviction shaded his statement as true.

Amanda instinctively grabbed him and drew him tight. "I'm so glad you finally said it," she said softly in his ear. "I think the hardest part is over now, don't you feel it?"

Jesse just rested quietly in her arms for a moment thinking. Finally, convinced and in a soft and subdued voice he answered, "Yes, I feel it. I feel like I just stepped off a cliff with no way back; but jumping is the only thing to do, isn't it?"

The tiny insecure question at the end of the bold affirmations made her love him all the more. She didn't yet know where to file this new kind of love, but she was not mistaken in its reality. "Yes, baby. It's the thing to do. Remember, you have nothing to lose. If you choose the wrong direction, just turn around and try another. Nothing bad is going to happen either way. If you're gay then you know, if your bi you'll know that, and if you find you don't like cock at all you can always find a woman to love."

"But what about my mini-dick?"

The quickness of the reply made it clear to Amanda that this was still an insecurity for him. "Okay, hand me the computer," Typing and scrolling for only a few minutes and then, "A hah, here it is. According to this study, the average male penis is 5.8" in length." Closing the screen she jumped up and rummaged in the desk drawer searching for the object of her quest. Jess's attention turned from his own dilemma to the perfect naked ass displayed so casually for him to admire. Turning she returned with a twelve inch plastic ruler the same shade as Jesse's panties. But Jesse's eyes had already refocused and followed the perfect breasts and womanly perfection walking toward him.

"Okay, pull 'em down again." She ordered bluntly.

"I'm not even that hard now, you can't measure anything like that!"

"Pull them down Jesse or I will pull them down for you." And the tone of her voice left him thinking she might do it as she tapped the ruler in the palm of her left hand.

But with him still resisting in a somewhat pouty way, Amanda negotiated another approach, "If you aren't hard I'll suck you until you are. How's that for a fair deal?"

Was it a deal, or a bribe? It didn't matter, as Jesse made a quick calculation of the pros and cons then slowly slipped the lovely fabric down past his knees. He wasn't quite as soft as he made out to be, but not fully hard either. "Okay, there it is. I'm starting to think you just like to torture people," he added trying to irritate her.

Not wanting to debate the fine points, and not being totally opposed to sucking him, Amanda flipped her hair back with a quick flick of her hand and lowered herself down to take care of business. Taking the semi-erect flesh in her hand she quickly gathered more interest in the task ahead, so with one quick lick to the exposed pink head she took him into her mouth all the way to his sparse pubic hair.

Jesse pushed a pillow under his head so he could watch as she expertly pleasured him. It didn't take long at all before his dick was as hard as it was going to get, and yet Amanda still continued. She had decided to blow him until just the last second in order to get the most accurate measurement. Not wanting him to cum beforehand though, she paused long enough to say, "You're not to cum, understand?"

Jesse heard but didn't answer quick enough. "Jesse, answer me! I want to measure you before you cum, you got it?"

"Yeah, I hear, okay I got it, better keep going...I'll tell you before..." He was so urgent in his need he unconsciously pushed her head back down to his abandoned erection.

After a couple of minutes Amanda was beginning to notice the tell tale signs. Jesse's cock was fuller and his quick humping into her face told her it was near. When Jesse still didn't say a word about stopping, she made the decision for him and pulled her mouth away from the sensitive flesh, leaving it there; wet, hard and straining for release!

"Okay, where's that ruler," she asked herself while searching through the tossed bedding. "Ah, here we go."

Jesse, returning to a semi normal state of mind, watched as Amanda performed her measurements. He idly thought she looked like some kind of naked scientist conducting an experiment.

"Yep, just about what I expected. You are exactly four and a half inches, that's pretty close to five inches. And that, my dear friend is definitely in the average range. So, you can do anything you want to with this," grabbing his cock to be sure he knew what she was talking about. "No more whining about being too small, okay?"

"Okay, but what I want to do with it now is for you to please finish what you started!"

With a small phony pout she replied, "Aren't you going to say thank you for proving it to you?"

"Thank you for proving I'm normal, now please..."

"You have to say pretty please now, because you were rude," she twisted the words in like a knife one last time enjoying the power she had over him.

"Pretty please then, if I have to beg I will." Jesse faintly felt the strange arousal in begging, but was too distracted to care at the moment.

And true to her word she returned to the task, that in truth, both were fully enjoying. Amanda had forgotten to mention to him another plus of a smaller cock, it fit so comfortably in her mouth...almost like an adult size pacifier or something.

Sadly, it didn't last near long enough for either of them, and his orgasm was almost as powerful as some of the big ones Amanda had swallowed. It was also deliciously pleasant to be able to throat the whole shaft down so easily. No reason to be too picky about size, she resolved for future reference. And poor Jesse, he had been stretched and torn in a dozen different directions these past few days, so a mind gone blank from shear physical release was like the best elixir money could buy.

But still horny herself, Amanda found the dildo abandoned in the sheets. "Be a sweetheart and get this wet for me," she purred as the lifelike dong touched his lips. Too spent to resist, Jesse with eyes still closed, parted his lips and took the head into his mouth. His tongue started to explore the new intruder as he floated in his dazed afterglow, his mind feasting on images of the cocks they has been looking at earlier.

"Here, you hold it, my arm is getting tired," she said replacing her hand with his without ever removing the imitation man from his nursing mouth.

Now he was holding the cock he was sucking, and although not real, it seemed real enough. His thoughts drifted and envisioned this to be the warm strength of his friend Rick. So with wonderful visions of Rick in his mind, Jesse kept getting the dildo wet for Amanda..."

Jesse was too absorbed in his own fantasy to notice that he was being watched. But Amanda was certainly watching and it was not hard to imagine him doing this to a real man in the bed with them. She had a leisurely look at his now shrunken cock laying exhausted on it's side, nestled in a bed of fine sparse hair where a few last drops of cum had flowed. Why did the words cute and sweet come to her mind, she wondered. Unconsciously her hand slipped between her legs. She hadn't really needed Jesse to get the dido slick, slipping two fingers into her pussy. She just wanted to see if he would do it.

Her mood was fueled by her own ignited arousal and the remembrance of dominating him last night. She savored how easily he surrendered to it. While Jesse enjoyed the imaginary cock in his mouth, Amanda was enjoying the fantasy of mounting him and fucking his virgin ass. Removing her hand before it was too late, she asked Jesse if he wanted to see something really cool.

Giving the dick one final suck, he relinquished the toy to it's rightful owner. "I think it's plenty slick for you now," he said with a grin.

"Now, what were you going to show me that is so cool? Maybe a close up view of you using it," he suggested.

"No, but I have something I bet you've never seen," she said in a pretentious arrogance.

"Mmm, maybe. But you'll never know until you show me, will you?"

"Okay Mr. Big-Shot, close your eyes and we'll just see," smiling in anticipation of the look on his face when he sees what she has for him.

Jesse was game and closed his eyes.

"Nope, turn and face the window. No peeking!"

As he obeyed and rolled over, Jesse heard the bedside drawer open again, noting that he now knew where Amanda stashed her toys. It seemed like a valuable scrap of information for some unknown reason.

Finally, after a couple of minutes of strange sounds, Jesse was told to open his eyes.

He opened them expecting to see the window, but standing a foot from his face was Amanda and she had grown a cock between her legs! He would have been embarrassed had he seen the look on his face. Wide eyed and staring with an unreadable expression. Perhaps astonishment, fear and lust combined would come close to what his face was saying to Amanda.

Noticeably swallowing he said, "That is really amazing. I have never seen anything like that," realizing too late that he just lost the bet. But that was just a fleeting thought and quickly ignored. "All I can say is that you look amazing with a cock. Where did you get it?"

"It's called a Feeldoe. Here, look how it fits up inside me," she offered while spreading her legs for a better inspection.

"Go ahead. You can touch it if you want."

Jesse didn't need to be told twice and gently explored the erect shaft and where it perfectly blended into her own body.

Reaching behind his head Amanda cooed, "Suck me baby, you know you want it."

It took very little encouragement from her hand as Jesse brought his lips to Amanda's cock. Closing his eyes, he took her into his mouth and proceeded to give her a blowjob. For both, it was a wildly pleasurable first experience. For Amanda, the pleasure was a visual one mixed with pleasant jiggles inside her pussy as Jesse's mouth bobbed up and down on her cock. However, Jesse's pleasures were a contrasting mix of continued fantasies of doing this for Rick, and sucking Amanda all mingled together with the pungent perfume of a woman's arousal.