tagTransgender & CrossdressersA Sissy's Journey Ch. 06

A Sissy's Journey Ch. 06


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 and male feminization. All characters are fictional and portray adults over eighteen years of age.



To say that Rick was shocked when he saw Jesse after the girls had worked their magic would be an understatement. He could only stand mute on the porch and stare at the beautiful creature before him for what seemed an embarrassingly long time. Finally, shaking himself back to reality he extended his hand and presented his date with a single red rose.

"You look stunning," was all Rick could say at first.

Jesse felt himself blushing and without thought stepped to Rick and embraced him with a heartfelt hug. Rick was more than eager to return the favor and thrilled at the small petit body he held in his arms.

After enjoying the warmth and strength of Rick's body, Jesse introduced both Amanda and Briana. Both girls would have been embarrassed by the expressions on their faces. Their wide eyes and parted lips made it clear that excitement was in the air. This was all new territory for all involved and the girls experienced a mixture of emotions ranging from apprehension to exhilaration with more than a little lust mixed in.

Finally getting her senses back Amanda said, "Please come in. It's nice to finally meet you in person Rick. Briana, meet the mysterious man in Jesse's life."

The four visited for about a half hour before Rick suggested he and Jesse should go in order to catch the reservations. The conversation had taken on a relaxed and comfortable air and it was clear that new friendships had been forged. With hugs and kisses all around Rick and Jesse walked into the evening and and into the age old courtship dance of the first date.


"I can't get over how much you have changed in such a short time," Rick said as they drove to the restaurant.

"You look pretty different too in a suit," Jesse replied. "I've only seen you in underwear and naked so far," he added jokingly.

Rick laughed and agreed, "A gay chat room is a pretty odd way to meet and get acquainted isn't it?"

"Yes, but I'm glad we found one where we could meet. I would hate to think we might never had known each other," Jesse said with true feeling.

"You and me both," Rick replied and rested his hand on Jesse's thigh just above the knee.

As they drove, Rick's hand gently rubbed Jesse's leg through the sheer fabric of the dress. The simple act took on a growing significance as the two sat silent with their thoughts going wild and wondering where this night would end up. For Jesse, it was the final moment of acceptance of what he had become. It was only strange feeling for a brief time, and then he surrendered and felt simply wonderful as the large strong hand comforted him.

Rick was now the one who felt a need to reassess his own feelings. Up to this moment he had felt it was just another date with another guy. But something very odd, but also very familiar, was starting to blossom in his heart. He was experiencing an attraction much different than he normally felt on a date. He had experienced this feeling once long ago, but he tried to push that thought away...it was too soon to be thinking like that, he told himself.

Turning to Jesse he said, "I'm proud of you. I'm proud to be seen with you tonight. You look gorgeous and when you walk in that door, I want you to know you look gorgeous."

Rick pulled into the parking lot and found a spot not far from the front door.

"Sit tight," he said to Jesse.

Rick got out and walked to the passenger door to open it for his date. This was another new experience for Jesse, to not only look like a woman but to be treated as one. But he graciously and daintily held the offered hand and stepped out of the car like a lady.

Not letting go of Jesse's hand, Rick drew him closer saying, "I haven't really kissed you yet, but I would like to do that before we go in if your ready for that."

Jesse felt a brief moment of panic at the thought of his first kiss by another man, but quickly pushed those feelings away and answered shyly, "Okay."

Pulling his date close, Rick's strong arms engulfed the small body. Instinctively Jesse looked up into his eyes and felt his knees grow weak as his lips drew near. The kiss must have lasted a full minute as neither wanted to pull away. The strong, and somewhat frightening, feelings Rick had felt earlier were only inflamed more by that first kiss. But Jesse felt no fears, in fact he felt more alive than he could ever remember! He took in the smell of this man who held him, and he felt a man's strength as

Rick held him tight. He felt the softness of Rick's lips on his and their tongues lightly said hello one to the other. And although unseen, both cocks were swollen and aroused!

As Rick opened the restaurant door and held it for his date, Jesse walked into his new way of life and he knew it felt just right. After a brief exchange with the hostess, they were led to a nice table overlooking the river below. Rick ordered wine and appetizers and the two settled in and started to get to know one another more intimately.

Two hours passed as if a moment, and it was time to go. But go where, Jesse wondered.

Once settled back in the car, Rick asked, "Would you like to go over to my place for awhile?"

"That would be nice," Jesse answered.

"You know, that was pretty fun when you had to go pee. I never thought about where you would go to the bathroom," Rick said and they both laughed.

"Yeah, I had overlooked that detail too," Jesse got out between laughs.

"And no one had a clue?" Rick asked.

"Not even a glance. All the women were just doing their own thing and didn't look at me twice," Jesse replied.

"I told you that you looked great," Rick added.

"I have to admit, it was quite an ego booster to know I could fool them in such bright light."

And off they went for the drive to Ricks place. But on the way, Rick decided to take a short side trip up Hillside Drive and enjoy the perfect clear night. As they drove, the easy conversation that had started over wine continued as the two new lovers got to know one another even more. After about fifteen minutes, Rick pulled into an overview and stopped the car. Since the bucket seats kept them apart, Rick once again got out and helped his date exit the low situated seat. Then hand in hand they strolled to the edge and gazed out at the city lights winking up at them. Rick stood behind Jesse and held him close, his strong arms easily enveloping the small young man. It was magical and wonderful, and both felt as if their bodies were blending together. Finally, he could resist no more and Rick turned Jesse to face him... and the kiss was all that either could think of.

"Let's go home baby," Rick said with a husky voice that sounded strange even to himself.

"Okay daddy," Jesse replied unconsciously falling into their old chat roles.

Pulling Jesse close, Rick kissed him one final time before they walked hand in hand to the car.

The emotions were running high and simple chit chat didn't seem necessary to fill the silence. In fact both were absorbed in their own thoughts as to what this was leading to. Finally Rick said, "Baby, you have me really worked up, I have to admit it. I don't want anything to get mixed up, so I want to ask you how you feel about all this...should we go to my place knowing it might be hard to not end up in bed together?"

"I've been thinking the same thing," Jesse admitted. "But I'm ready if you are."

There, it was out. No more wondering or dancing around the issue. Rick still didn't want to rush the young man he was growing really fond of, so he pondered the pros and cons before answering. "So long as you know, you can't un-ring the bell. Once I mount you and we go all the way, I just want to be sure you won't regret the decision. So, I'm going to keep driving to my place, but I want you to keep thinking. And you can change your mind at any point, is that clear? No means no, and I will respect that, you understand?"

"I understand Rick. And I respect you even more for saying that," Jesse replied.

Rick resumed his caress of Jesse's leg, but after a while it was Jesse who took his own hand and guided Rick upward to his panty clad cock. Rick didn't need more encouragement and eagerly pressed his hand over the little cock that was straining against the silky fabric. Jesse spread his legs and was so aroused at the sight of his legs spread like a girl he had to stop Rick lest he cum.

"I guess I'm pretty worked up. I almost came in my panties," he confided to Rick while holding his small hand over the strong hand now on his upper thigh.

"You're not the only one Baby, I haven't been this worked up in a long time...you're quite the little tart I think," Rick said while giving Jesse's erection one last little tug.


Rick's house was much nicer than Jesse had imagined. Clearly, Rick had done well for himself. The style and the furnishings perfectly reflected the kind of man Jesse had come to know though. A modern, sleek and upscale decor that was perfectly balanced and brought a nice sense of peace to the home. Since the night was still young and the weather perfect, Rick suggested they sit out by the pool with a cold beer.

The pool area was also well designed and elegant, and the two settled into comfortable chairs to enjoy the quiet evening. After only a short time of casual conversation, Rick bluntly said, "I would like you to come over and kneel between my legs. You can bring the chair cushion so you don't ruin your stockings."

So this was it, thought Jesse. The moment he had been dreaming about and fearing...the moment he would taste his first cock. But there was no thought of not doing as he had been asked. It took some nerve to cast away everything he had ever imagined himself to be, in reality he had already done that and this was just the outward demonstration of that repudiation.

Rick watched as the sweet beautiful boi obediently got up and retrieved his chair cushion and placed it between Rick's spread legs. Then the young submissive gracefully went to his knees before his man.

"Do you want my cock," Rick asked pointblank.

"Yes," came the meek answer.

"You have to beg me," Rick replied.

"Please," Jesse offered.

"Not enough. If you really want it you better make me believe you," Rick quickly shot back.

"Please Daddy, please may I suck your cock," Jesse said and felt the rush of his humiliation and arousal.

"I don't know. You don't seem to really want it," Rick said, continuing his boi's torment.

"I do want it Daddy, I need it so bad! Please, I beg you to let me be your cocksucker...please Rick, I can't stand it any more!"

"Stand up," Rick ordered.

Jesse scrambled back to his feet and stood silently in from of Rick...waiting.

'Lift up your dress and show me your panties," Rick commanded.

Jesse obeyed without hesitation, and delicately lifted the hem of the dress as high as he he could. He felt so weak and ashamed as he stood there open to Rick's inspection for what seemed an eternity. Rick was totally engrossed and aroused by both the willing submission and the pretty boi in front of him who had an obvious tent in his panties.

"Step closer," Rick asked quietly.

Reaching out now, Rick gently felt the front of the delicate panties and the compact little toy hidden in them.

"Turn around," Rick said bluntly.

Jesse obeyed, turning in as feminine way as he could while holding his dress up daintily. He had a clear thought to himself that this was the most arousing sexual encounter of his life so far. He felt totally weak but also totally safe with this wonderful man.

"Bend over," was Rick's next requirement. And again, Jesse complied with never a thought not to obey.

If Jesse had felt exposed before, he now felt even more so as Rick gently peeled the expensive panties down over the plump ass cheeks to expose the prize he had longed for.

"Let's just get these out of the way," Rick said, and pulled them all the way to Jesse's ankles. Jesse lifted one leg and then the other so Rick could get his panties fully removed.

"There, that's better. Now let's try this again. Lift the dress up again Jesse."

And of course, Jesse obeyed and was feeling happier than he could ever recall. Oh how did he ever have any doubts about who and what he was. He unconsciously let out a long sigh of relief which was in itself a true testament of how perfect he felt inside about his new life.

As Jesse stood holding his dress high while Rick examined his ass, Jesse glanced up and it seemed that the entire sky full of stars was smiling down at the two lovers as they were beginning this new found love. The warm strong hands on his inner thighs brought Jesse back down to Earth. The gentle pressure told him what was expected and he obeyed by spreading his legs wider apart.

"Bend over baby," came Rick's gentle voice.

"Yes, Daddy," Jesse said and bent at the waist to expose himself even more to this man who seemed to own him body and soul.

'Baby, I want you to take both hands and spread your pussy for me...will you do that for me," Rick asked as he gently massaged the soft mounds of Jesse's bottom.

"Yes sir, I want to show you," Jesse answered truthfully and then did just that. Pulling his cheeks apart as wide as he could he exposed his most private gift to the man he knew he was falling in love with.

Jesse was shocked and thrilled when he felt the warm kiss on his exposed hole...but when Rick's tongue started to explore that opening deeper, Jesse felt it couldn't get any better than this moment!

"Okay baby, now you can turn around a kneel before me again," Rick said. He too was as enthralled as he could ever remember, and he was certainly no novice. This boi was really starting to develop into something very special...but he pushed those thoughts away for the time being.

Jesse had recovered his cushion and was once again in the classic cocksucker's position before his man's spread legs. He looked up at his Master and Rick couldn't help thinking how sweet and perfect he looked. Breaking his plan to avoid too much softness, he leaned forward into a long kiss. The kiss lingered and Rick pulled Jesse up onto his lap and wrapped his arms around the boi. Rick had not been intimate with many guys who could draw out this side in him. But for some reason Jesse was throwing him way off his normal game, he noticed it but didn't fight the change.

"Baby, I had a plan for us to get things started. But you're making me crazy I think. Let's take this to my bed, okay?"

"Okay Daddy, anything you want. And just to be clear, I'm not going to say no. I can't tell you how much that offer to stop means to me, but I don't want to say no to anything you want to do," Jesse said that while being held close and looking up into his man's brown eyes. The kiss that followed was Rick responding in the best way he knew to tell his boi how much that surrender meant to him.


Ricks bedroom was as wonderful as the rest of the house. The sliding glass opened onto the patio and overlooked the pool. The kingsize bed seemed to dominate the room though, and Jesse could recognize some of the things he had seen during their chat sessions. And now he was here! He looked at the bed and the thought crossed his mind that he would loose his virginity on this bed tonight. The thought thrilled him and he turned again to Rick and hugged him close.

Without being asked, Jesse dropped to his knees. Looking up he said, "May I please take you cock out and suck it?"

"Yes baby, you may show me your devotion," Rick replied and smiled at the sweet boi looking up so innocently.

Without hesitation Jesse began to work on the buckle and zipper.

Rick stopped him saying, "Take my shoes and socks off first sweetie."

Jess quickly obeyed, feeling kind of dumb for overlooking that. Once they were out of the way, he started again on Rick's pants. But again Rick stopped him, and tipping the pretty little face up he said, "I would like for you to show me that you are truly submissive to my every wish. Kiss my feet Jesse. I'm want to push every spec of manly pride out of you. Are you truly as submissive as you imagine? Show me."

Jesse had fantized, but never fully thought about, just how it would feel to do things that no real man would ever consider doing. His ideas had all been about cocks and asses, for the most part. But it didn't take him long to embrace the warm feelings of shame that going farther hinted at. In that fleeting moment he acknowledged to himself that he really did want to throw away every shred of his manhood for this man he knelt before. So without a word, Jesse bent down and kissed his man's feet. He then went one step further and licked them both before looking back up to his master's face.

'Do you feel thankful that I made you do that," Rick asked.

"Yes Sir, I learned that I really want to give up my manhood to you. Thank you Daddy for helping me see that," Jesse replied and meant every word.

"Good. Now you can continue digging out you reward," Rick said in a kind tone as he gently smoothed his hand over the top of Jesse's head.

Jesse didn't have to be told twice, but with one last act of submission he bent once more to kiss his Master's feet before resuming his efforts to uncover his reward.

It didn't take long before the fat swollen cock was free and within inches of Jesse's face. He could smell the arousal and feel the heat coming off the impressive example of manhood. Having never held another cock, it felt so very large and heavy in his hand. Oh how did he ever think he was a real man, he again asked himself. What woman would ever be satisfied with his toy if this is what real men have to offer? He was just thankful he no longer had to worry about that, he was going to join the other team and begin to enjoy these kind of cocks too...and he was willing to give up whatever was required in order to make Rick happy and satisfied! In that moment, he realized that his satisfaction came as much from making his man happy as being sexually satisfied himself.

Rick kicked himself free of the slacks and underwear, and then quickly stripped away his shirt. He now stood totally nude over the virgin sub-male kneeling before him. Rick acknowledged with satisfaction the absolute power he held in his hand, he also was wise enough to accept the responsibility that came with that power. So with a now gentle hand, he eased Jesse's face to it's new found position of service, and with the other hand he guided the swollen flesh of his desire into the willing mouth eager to feed on it.

And so it finally happened. Jesse was on his knees still in his dress and he was sucking a cock that would be considered by anyone to be a prime example of virility and manliness. And in all of this Jesse felt more at peace than he had ever felt in is young life. There would be no going back...who could ever retreat after finding the pot of gold at the foot of the rainbow? Who could go back knowing they have found the truth of their own being?

Rick had already decided that he would feed his boi his first big load of spunk of the night. He already knew the second flood would go into Jesse's pussy. This would be the first of many such feedings...feedings that experience had shown him had some power of their own to make changes in the men who swallowed them. Rick knew he had a certain power over sub-males. He didn't let it turn him into an arrogant ass, instead he looked upon it as a gift that he could give to those who were weaker than himself. He didn't have a need to make these kind of men weaker, he understood that they already wanted that and just needed encouragement to be true to themselves. But he had to admit; he loved feeding them the elixir that would hasten their change.

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