A Sissy's Journey Ch. 07

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Rick and Jesse find love together.
3.3k words
4.69
19.2k
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Part 7 of the 7 part series

Updated 06/08/2023
Created 04/11/2017
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yukonnights
yukonnights
506 Followers

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.

*****

PART SEVEN

The master bath was like none Jesse had ever seen. The large walk-in shower was complimented by a built in hot tub and the entire room was covered in some type of gray marble tiles. Rick turned the water on in the shower, and Jesse noticed there were double shower heads.

"Okay baby, turn around and let's get this mess off of you. I'll drop it off at the cleaners and make sure Amanda gets it back in good shape," Rick said and started helping Jesse get the dress off. The little bra was a nice surprise and it matched the panties that had already been stripped away earlier. Rick smiled at the image of Amanda picking this out for her sissy friend.

"Okay, now I'm just going to stand over here and watch you strip the rest of these pretty things off," Rick teased and leaned casually against the vanity. Jesse couldn't help but notice the fat placid cock that lay heavily on his thigh. Damn, he thought to himself, what a beautiful man!

Jesse did his best to look sexy as he removed the bra, stockings and garter belt, and if the slow swelling of Rick's cock was an indicator, he did indeed look very sexy. Now both were fully nude, and without forethought they both moved to embrace and enjoy the feel of naked skin on skin. Jesse was overwhelmed with emotions and wild thoughts revolving around about how strong Rick was and how safe he felt in his arms...he gave a passing notice to the thought that he was slipping farther and farther away from his own manhood, but it was a passing thought of little importance as he melted deeper into the man who held him.

As the two held together in physical closeness, their inner selves were also beginning to blend together. Rick again acknowledged the feelings of a long suppressed ability to love trying to resurface. This time he didn't push it away so quickly, but said to himself; we'll see...we'll wait and see. When Jesse looked up and smiled, Rick could only chuckle at the mess he had made of all of Amanda and Briana's work doing the make-up. But despite the mess, it was a perfect and beautiful face that was looking up to him, and the kiss came naturally and with meaning.

"Okay you, quit tempting me or the hot water will be all gone," Rick said and gave a playful smack on Jesse's naked bottom.

Ah, the warm water felt wonderful! They each took turns soaping and washing the other. Then they just stood snuggled together under the soothing flow of water.

After several minutes of this, Rick said, "I need to piss. I haven't gone all night and the wine and beers are letting me know it. Do you want to hold it while I pee?"

"Sure," Jesse quickly replied. He didn't admit that he always peed in the shower because it felt so free and he could stand up and do it without fear of missing the toilet. He was still ashamed that even though he grew to about four inches hard, when he wasn't aroused he shrunk to about an inch or two and it was hard to hold it and pee standing up. So far, Rick had not seen him at his smallest but it weighed on his mind. But the thought of holding a real cock as it pissed sounded super hot at the moment.

"Okay baby, grab ahold. You're in control," Rick said.

And Jesse did as he was told. Standing in front of, and just to the right of Rick, Jesse held the big tool in his left hand and pointed it forward. Rick let his flow begin and Jesse started getting hard almost at once. The feel of a real man's cock, all warm and full and with a strong stream pouring out of the end flipped on a switch of lust. Without asking he pointed the flow onto his own now hard dick.

"I want you to mark me, Daddy," was all Jesse could say as he looked innocently into Rick's eyes. It made no sense to him and he had no idea where the thought came from. But he knew he wanted this man to mark him with his scent.

Rick was more than happy to oblige. He had done a little piss play, but this was really much more emotional. Taking his cock back, he urged Jesse to his knees and once he had knelt before him, Rick marked him as requested. He was glad now that he had foregone the restroom for so long. When the flow trickled to an end, Jesse remained on his knees looking up at his Master. No words were spoken, but it seemed that both knew what to do next as Jesse leaned forward to take the cock into his mouth and suck. Rick could only lean back against the smooth stone wall of the shower, close his eyes and try to absorb all the sensations and emotions that he was experiencing!

While Jesse was still contentedly sucking his Master, Rick slid his back down the shower wall, robbing Jesse of his cock, but quickly offering his lips to the young man who was destroying all of his hard resolve to not get too attached to another person. As the shower rained down, the two lovers became as one in a kiss that had the power to change the direction of both lives.

When they paused, Jesse laid his face on Rick's chest and gently fondled the cock he had come to adore. While looking down at his Master's manhood, Jesse said in a quiet voice, "Daddy, I think I'm falling in love with you."

The words that Rick had tried to avoid for almost five years would not give up the quest for him. And it wasn't just the words that haunted and frightened him, it was the emotions and the risk that went with the words. But he felt his resolve being stripped away by this small young creature.

"I know baby, I feel it too," Rick sad softly as he held Jesse close. "We'll have to just wait and see. It's too soon for you to know. We don't really even know each other yet."

"I know I've never felt this way before," Jesse said in an equally soft voice.

Rick was glad for the shower water because it would hide the tears that he felt beginning to build in his eyes. Instead of saying anything, he just cradled this young bundle of innocence and softness close. After an unmeasured space of time, the water finally did begin to turn cold and it was time for the two lovers to move. But tipping Jesse's face upwards, Rick kissed him one more time and had the water been warmer, who knows how long that kiss would have held.

*****

The quiet intimate moment of connection gave way to a lighter and more playful attitude as the two lovers helped each other dry off. With all of his make-up washed off and totally nude, Jesse didn't look quite as much like a true female. Rick was more than pleased though, and liked the small tom-boy appearance just as much. He had never dated anyone with such a small dick, but found that he liked it a lot. It was odd, but Jesse's inadequacy as a man made Rick feel even more protective over him. Both of them were semi-erect as they horsed around and worked their way to the bed that seemed to be pulling them like a magnet. Rick caught his young protege by the waist and pulled him close, nuzzling a kiss on the side of his neck. He then whispered in Jesse's ear, "I'm going to fuck you more than once tonight. You know that, don't you?

Jesse felt like he was melting into this wonderful man who held him. The thought of being fucked by Rick's manly tool didn't frighten him a bit, in fact he craved it now more than ever before! So it was easy to say, "I know Daddy. I know you're going to turn me into your bitch tonight. We've dreamed and chatted about it, but now it is real, and I am so ready for your cock to be inside me...I can't even tell you how ready I am."

"Do you need to clean yourself out first," Rick asked.

"I don't think so, Amanda thought of that earlier. I think I'm clean,"Jesse replied.

"That's an amazing girl. I wouldn't mind thanking her personally with the same thing you're going to get tonight," Rick said while holding Jesse close and gently playing with his clitty and tiny balls.

"I don't think it would be very hard for you to do that if you really want to. She's thinks you're hot stuff after that little peek she got when we were all chatting," Jesse replied.

"I was just kidding, it is your pussy I want tonight," Rick said lifting Jesse into his arms and laying him on the bed. Crawling on after him, Rick positioned himself on all fours over Jesse like an animal on his prey. But this animal only attacked with more kisses on the face and lips of the delicate creature under him.

But the kisses turned into more as Rick explored with his mouth and tongue down Jesse's body. First the neck and shoulders, then he took Jesse's right nipple into his mouth and sucked it up until it was hard and erect. Replacing his lips with thumb and finger, Rick pinched and pulled the nipple even larger as his lips began working on the other one. Jesse had already discovered his sensitive nipples many years before, but he had never experienced the sensations he now felt. The things Rick was doing to him made him feel both feminine and weak, and the shooting jolts of pleasure from nipple to clitty was like a live wire full of electricity! And indeed his clitty-cock was fully alive and erect now.

Finally Rick relented from his almost unbearable attention on Jesse's nipples, but it was to continue his kisses down the smooth tight belly only to settle on the final object of his desire. Jesse was so small that Rick easily took his cock completely into his mouth. And the pleasure Rick was giving with his mouth, Jesse had never experienced or even dreamed of. But when Rick spread him and positioned him so he could lick Jesse's virgin pussy... that is when he knew being Rick's girl was all he wanted in the whole world!

For Jesse things began to blur from one sensation to the next as Rick had his way with the lithe young body. But when he felt Rick begin to apply the cool lubricant to his puckered little hole, Jesse knew it was time. Rick resumed sucking Jesse's clit as he fingered him and worked the lube around. Rick took plenty of time to get Jesse hot and ready for the cock, and even had to ease up a couple of times when Jesse almost came. But finally the time had come, and Rick knelt between Jesse's spread legs.

"You have to beg me for it baby," Rick said quietly. "You know that, you always have to beg me for what you want. Can you tell me what you want?"

"I want you to fuck me Master. I want you to breed me like we have dreamed about. I want you to seed me and make me your bitch boi...please Daddy, I beg you to fuck me now!

"Okay precious. Here, pull your legs up like this and hold them. That's it, a little higher so your pussy lifts up for me. There, now just hold tight and look me in the eye while I work my cock into you," Rick instructed the young virgin.

With lot's of lube on both pussy and cock, Rick started the final dance. Slowly rubbing the engorged head around and around the quivering cunt hole, Rick finally started to ease it in. Just a little of the bulbous head, then back out...then a little more...and a little more...

Jesse was in a lust induced trance. The pleasurable sensations had almost overloaded his senses. But he knew what was happening...oh yes, he could feel every millimeter of cock as it worked into his body. He didn't feel any pain, just a wonderful full feeling...the feeling of his man inside of him. It was more wonderful than even his wildest dreams! The dildos he had used for so long had served their purpose. But they could not come close to the real completeness of a man! The hard, but soft rod was hot and alive. The weight and power of the man could never be mimicked by a piece of silicon shaped like a cock. And once Rick was buried to the hilt inside of Jesse, he lay all of his weight down on top of him. That weight was like a soothing antidote to any apprehensions that might have tried to flutter to life.

Now Rick was fucking his boi in earnest. Jesse lay passive under the power of the man on top of him. He wrapped his arms around Rick's chest and lifted his legs high up on Rick's back so he was more available to his man. These actions were not born of forethought, but were the pure animal instinct of a female in heat...and that was how Jesse felt, like a female being taken hard and loving ever thrust of the powerful cock into his body. His only goal now was to make his man happy and satisfy him with his pussy.

But Rick was an experienced lover. And he was also a generous lover. He took pride in bringing those he fucked to the best orgasm of their life. So, Jesse discovered that it was impossible to only want to please his man. Rick was doing things to him on the inside that no one had ever done, he was hitting all the secret spots that drive a fem-male wild, and Jesse was starting to feel very wild. What began as gentle thrusts deep into his body, soon became like lighting bolts of sensations that were bringing him to the brink of orgasm. It happened almost unexpectedly, but there was no mistaking the fact that Jesse was about to cum from being fucked like a girl. The feelings welled up from some hidden place and erupted in a passionate flow of cum that coated the two lovers where there bodies were pressed tightly together. Feeling the warm flow of Jesse's release, Rick redoubled his efforts and fucked every drop of Jesse's cream out of his body. He fucked him until Jesse was limp with exhaustion and spent with orgasmic pleasures.

Rick lifted himself up a bit and looked at the face of his boi. Jesse's eyes were half opened but unfocused, his mouth was slack and clearly the lad was spent. Rick slowed his pace, but kept a steady rhythm which would bring him to his own climax. As he fucked Jesse slow and steady, the boi began to recover and participate more. And soon they were both making love in sync like they had been lovers for years. Now it was Jesse's turn to make it great for Rick, and he did his best.

"Fuck me Daddy, open me up with your cock," Jesse cried out. "I need it in me daddy, I need your cum in me...please, I'm begging for your cum!"

And the passion in Jesse's plea drove Rick to the point of no return. A few more powerful thrusts into the depths of Jesse's body, and he tensed up and filled Jesse with his seed!

Drenched in sweat, and spent of all energy, the two lovers lay in a heap as one. Jesse felt the crush of his man's weight on top of him and he relished how small he felt. Rick's cock was still buried inside of him, and he could feel it growing softer. But what a wonderful feeling that gave Jesse, knowing that he had satisfied his man.

And yet, Rick's cock was still hard enough to bring a little pleasure, and as he slowly and gently humped into Jesse the abundance of creamy spunk made for a wonderful squishy sensation as Rick slowly fucked him. But all things must come to an end, and after a couple of more thrusts Rick pulled out and rolled off onto his side.

Jesse immediately rolled over and snuggled close saying, "Thank you for fucking me. I had no idea it would be so wonderful...I really had no idea how good it would be."

Rick kissed him softly on the forehead and replied, "You are more than welcome, sweetheart. It was especially good for me too. You are just perfect and beautiful to me."

"Rick," Jesse started in a soft tentative voice, "I know you probably don't want to here this...but I really need to say that I love you. I love you for fucking me and I love you for helping me find my way to where I am right now. You don't have to love me back, but I can't stop from loving you."

But the intensity of breeding Jesse had somehow moved Rick to a place where he could once again consider love. No, he didn't really want to think about it...but it was here...it was snuggled up close to him offering love in return. The truth was that Rick was afraid to love, but Jesse was tearing down his carefully built walls.

"I want to love you Jesse," Rick started trying to explain. "But I was hurt by love many years ago and it's hard to trust like that again. But I want to love you...I do feel that again. I love you too Jesse, but I'm afraid of what you might do to me.

Jesse was stunned to see the vulnerability in this strong man, and that vulnerability made his love even more alive. "Rick, I'm sorry. I didn't mean to pressure you or anything. But I would never do anything to hurt you. I have never felt like this before, is all. I can shut up about it if you want me to."

But Rick had made up his mind to try love again and said, "No baby, it's not you. It's me who needs to get over my hang-ups. I accept your love, and I offer my love back to you. Let's just keep it like that. So long as we both offer and receive love from each other, then we will share in that love. Let's just go one moment at a time, and maybe it will end up being a lifetime of moments where we share our love."

Pulling his precious fem-male close, Rick kissed Jesse on his lips. Then looking down into his eyes Rick said softly, "I love you."

"Now, let's go rinse off. Somehow we made a mess of ourselves again and I'm exhausted," Rick said smiling at his new found treasure.

*****

The End

*****

A note from the author:

Of course the story of the love between Rick and Jesse could go on and on. But this is a good place to stop and we can all imagine the rest of the story. Perhaps one day I might continue with this tale, we'll see. Thank you all who have read this far, I hope we might all find such love as Rick and Jesse did!

yukonnights
yukonnights
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7 Comments
robin48robin48over 4 years ago
Touching story

Very sweet and emotional..Would have liked more details of the deflowering of the virgin but it was a great story..TY

AnonymousAnonymousalmost 7 years ago
WOW!

Damn! I'm so jealous of Jesse. I wish I had girls that would be that understanding. The whole story was well written.

Thanks

yukonnightsyukonnightsalmost 7 years agoAuthor
Thank you all !

Just wanted to add my own comment thanking everyone who read this story. A special thanks for those who took the time to write a comment! It really does help to hear how others view the work, and the constructive criticism helps me on the next one.

blade_rocknutblade_rocknutalmost 7 years ago
Enjoyable.

I do enjoy your writing. Not every chapter was quite as engaging, but you did an admirable job of creating this fantasy world without resorting to tired cliche.

AnonymousAnonymousalmost 7 years ago
A Good Loving Story

I would have loved a chapter about Amanda & Brianna having a threeway with Jesse after getting her dressed, instead of her going onto the date. I also would love a followup with all 4 together.

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