A Sissy’s Journey Ch. 02

Ben Esra telefonda seni bosaltmami ister misin?
Telefon Numaram: 00237 8000 92 32


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.



The notice on the top of his toolbar gave Jesse an emotional lift. It was Rick inviting him to chat and that always made for good endings.

“Hi Jess, long time no hear” read the message.”

“Hey yourself. I thought you had grown tired of me,” Jesse typed back.

“Aw, who could get tired of your sweet little clitty dick and that pert pretty bottom?”

“You always know just what to say to guys like me, don’t you?” Jesse had been able to freely share so much with Rick in these anonymous conversations. He really felt like a true close friend now, and in fact he knew more about Jesse’s sexual desires than anyone else in the world.

“Guess what happened to me,” Jesse typed in wanting to share his experience with Amanda.

“Tell me.”

Jesse smiled at Rick’s typical bluntness.

“I failed again in fucking a girl…went soft as a baby when I tried to put it in.” Jesse felt a pleasant stirring in his underwear at the frank confession of his shame. Pulling the fabric aside, he freed his little friend and started to gently rub himself.

“I don’t know how many times I have to tell you but man, you’re gay! gay! gay! When are you going to accept it!”

“I know and I’m trying to accept it. But do gay guys get hard when they lick pussy? I love doing that and it gets me really hard,” Jesse answered, still trying to figure it all out.

“Okay, maybe you’re Bi like me, but you are not a man like straight guys so give it up already!”

“I know, you’re right and I’m starting to believe it lately. She really got me going though and made me submit to her.”

“Hey, I could have told you a long time ago that you were sub…just run with it and see where it goes,” Rick advised.

“I really wanna to do that…it feels so right for some reason. But I also like the things we’ve talked about…you know, like being on the bottom and doing things like that for a guy like you.” Jesse’s hands were slightly trembling as he hit send. Yes, it was just anonymous chat, but he felt connected to Rick. He respected his older friend’s experience with other men and didn’t want to make a fool of himself with him.

“Baby, I can read you like a book. Trust me when I say this to you; you are a sub bottom. You may be bisexual but you are queer to the core and you’re going to explode your brain if you don’t start accepting it. That’s no BS, okay? I want you to find your happiness.”

Wow, this must be serious, Rick has never been so caring. Jesse wanted to be sure to respond with the right words, “I really appreciate that, and I know you are right. I’m going to start right now and admit that I am queer. Maybe bi maybe gay…I don’t know yet…but yes, I admit it to you and myself.”

“Okay, I’m glad you finally said it. If I were close enough I would come over right now and prove to you that you are a sub bottom who needs a man in him!”

“And I would be here naked waiting for you…I want to service you like a girl would and make you feel so special.” Jesse was now hard and very close to the orgasm he needed really bad!

“Turn on your cam and jack off for me”. Back to the same bluntness Jesse knew so well.

“There, can you see me okay now,” Jesse asked.

“Yep, there’s my tiny friend…now shut up and make yourself cum thinking about my big one in your ass.”

It took about a minute for Jesse to obey his online Daddy. It was wonderful knowing Rick was watching as his balls tightened and he erupted high onto his chest and neck. sinop escort Gently and expertly Jesse pleasured himself until the last drops were smeared and matted in his slight pubic hair.

“You are such a sissy Jess! I love it and would own you if I could. The only thing I would change is you would be in panties if I were your Daddy!”

“For you I would wear anything and do anything you wanted.” And Jesse knew he meant that, in this moment at least.

“I know sweet one. I gotta get to work, keep in touch.” The signed off notice was pretty typical of Rick’s exits. He never said, but Jesse just knew that Rick was pleasuring himself the same way he had done on camera. However, he didn’t need to see it so much, he just enjoyed pleasing Rick for some reason. And he admitted he liked being attractive for him. Rick had become the only man who Jesse could confide in and he respected his advice.


“So what’s new?” Amanda asked once Jesse had plopped onto the couch. It was a stay home movie night, a special time often shared settling into a Netflix show and eating popcorn.

“Did I ever mention Rick to you? He’s the older man I sometimes chat with online.” Jesse wanted to get this out in the open but he wasn’t always the most graceful in his approach.

“No, tell me.” Amanda had spent hours reliving the intense intimacy the two had shared three days ago. She could feel herself getting wet just from looking at him and remembering how he looked the last time she was with him. And now this new bit of information. Truly, Jesse was more complex than she ever imagined in all the years she had known him.

Noticing the hesitancy, she added,”Come on, no more secrets remember? You actually have no choice but to trust me and keep me humored, you know?”

“Okay,” Jesse felt relief in the way she had made the decision and taken the choice from him. Somehow that made it easier to tell her. “I have been online with an older Bi guy for several months. He thinks I’m gay, or maybe Bi. I told him about the other night and he said he knew I was a submissive from the first time we chatted.”

“What does all of that mean?” Amanda asked, but was also wondering when the new surprises about someone she thought she knew would end.

“I’m sorry, that was kinda lame, wasn’t it? He is an older man who likes younger men like me. He has been really kind to me and helped me to talk about this stuff. He wants me to be happy and said I need to start being honest with myself and also love myself for what I am, not what I think I should be. Stuff like that, you know?” This was starting out to be another one of those really awkward conversations. Was this a mistake, Jesse wondered.

“So, have you figured it out yet? Have you had sex with him?” Amanda had not venture too deeply into online chat rooms, so wasn’t sure what to say. What she did want however, was for Jesse to feel safe in talking freely to her, so she hastily added, “I mean, it’s none of my business and perfectly fine if you have…just talking it out, okay?”

“Oh no, Rick has hinted at meeting but I don’t think I could do it for real. It’s just online stuff. He likes to play my Daddy and for me to be his sub. It’s mostly just fantasy play, but he is also really wise and caring. You know, it’s just that kinda stuff.” Whew, this was getting harder than he had envisioned.

“Okay, that’s understandable. I’m glad you have him to talk to. Why are you telling me this now though?” She too was wondering if this was getting a little too muddy.

“Well, Rick told me today after I described how you dominated me the other night and what we did…hmm, he told me I should accept being homo and go have sex with a man so I would know for sure one way or the other. You’re the only other person I can talk to like this, guess I just wanted your advice too. Sorry for making it weird.” There! It was out at last for better or worse.

“You sivas escort take more words to say something than anyone I’ve ever known. But yes, now I understand. Come here and give me a hug.” Amanda would always be a softy for any lost kitten or bird or best friend so Jesse was used to her hugs. He also loved getting them.

Another rush of relief as one more piece of the mask was destroyed forever. Jesse didn’t fully realize it yet, but he was slowly untangling the chains that had constrained him for many years. But he did realize that something good was happening and he felt so free for the first time in such a long time.

The hug, turned into a kiss and the kisses started to linger. Amanda, being an introspective and thoughtful person, didn’t let the kisses interfere with pondering the deeper implications of all Jesse had just confessed. She caressed his long curly locks as she cradled him to her now exposed breast. He suckled her almost as a baby. In that moment she was able to see Jesse in a more pure light, a light that revealed a much more delicate nature than even she had imagined. It dawned on her that the way he sucked her nipple was more similar to the way other girls had done it. He really was a more gentle type of man than she had thought. Looking down in the dim light, his face was almost childlike in it’s innocence, and she loved him all the more but in a new and unusual way.

“So, did you do what Rick advised,” she asked softly while stroking his cheek with the back of her hand.

Dropping the swollen nipple from his lips, Jesse replied, “You mean suck a guy? Oh, no I haven’t really thought about it much.” That was another lie, but Amanda let it pass.

“Why not? I think it is pretty good advice myself.” She said it, and mostly meant it too. But it was just very new trying to convince your best guy friend to go find a cock to suck.

“Really?” Jesse asked sitting up. “You really think I should do it?”

Amanda didn’t answer immediately since she wanted to be sure what she said was right. As she thought, she pulled her shirt back down to cover her breasts. Finally satisfied with her answer she said simply, “Yes, I think you should do it.”

“Are you sure?” Jesse was surprised and felt suddenly very hesitant with where this was going. “And how do you propose I go about doing that?” It was a ploy he didn’t even realize he was playing, but it was easier to put it into Amanda’s hands than figure it out himself.

“Oh, I think we’ve already figured out enough for one night, haven’t we? Everyone agrees that you are either gay or Bi and that you now need to act on it. You agree, don’t you?” She was always quicker with words than he was but he never seemed to learn that.

“Well, I guess so. Just wondering how to do it is all. Not so easy, you know? And a good way to get killed, maybe.” Now he was just babbling so decided to shut up.

“Okay, we’ll figure it out tomorrow. Now tell me everything Rick said, I want to know it all.”

“Well, we have sort of this Daddy and Boi kind of thing going. He is middle aged and a real man’s man. He showed me pictures and I’ve seen him on cam a few times too. I think you would like to have him between your legs,” he was getting back at her for making him tongue-tied before. “He is hung like a horse and muscular. He’s really hot, to be honest.”

“So he wants to fuck you? Does he say that to you?”

“Yes, he isn’t shy at all. I think that’s one of the things I admire about him, he’s so confident and knows what he wants. And yes, he said he wanted me. He said he would like to take me like I was a little girl. Today he said he wanted to put me in panties.” Just the retelling of the conversation was so arousing, and to be saying it to Amanda was something he would have never imagined a few days ago.

“How did all that make you feel?” She asked in a voice forced to be much calmer than she felt inside.

“Oh, tekirdağ escort no big deal. You know, it’s just guy talk.” Now that was a big fat lie, he said to himself, but some things are just too embarrassing to share.

“Show me.” Amanda had her stern voice again.

“Huh, what do you mean?”

“You know exactly what I mean. Pull you pants down and show me your dick right now!” She was serious and it was clear what she expected.

Since he was taking too long, Amanda jumped up from where she was seated next to him, bent over and ripped open his pants. He was too stunned to react and she had them and his underwear down to his knees before he knew what happened. Then, there it was for all to see and his little friend had betrayed him again. Only this time the betrayal wasn’t because it was soft, no it wasn’t soft at all. In fact, it was sticking straight up into the air and seemed to be screaming like the town criers of old saying, “Look everyone, I’m a queer!”

“Okay, we’re done with the lying and half truths, understand?” She was really serious now, or so it seemed to Jesse. Wide eyed he meekly surrendered with, “Okay, no more lies. Tell me what I’m supposed to do? I honestly am too confused to know what to do.”

“Come here and give me a hug.” Now she had turned the tables on him again and was cuddling his face into her tummy as she stood in front of him on the sofa. His pants were down and he was fully exposed, but it was the exposure of his innermost soul that left him weak. No more hiding now. Rick and Amanda had stripped him of every scrap of the camouflage he had assembled. But it was over now. Jesse knew this was a real moment, a true turning point, and it was both frightening and a relief.

“Baby, tomorrows another day. How about spending the night with me,” Amanda asked, proving again that she really was one of those friends everyone wished for.

“That sounds really nice, thank you” he said in a suddenly exhausted voice.

“I have just what you need to sleep in, so don’t worry about that.” Oh how she knew how to set the hook when she wanted to.


“Huh what,” she replied.

“You know what I mean, what do you have in mind now,” he asked warily.

“Well, if Rick thinks you should be in panties who am I to disagree? Besides, you’re not sleeping in my bed without a shower. And if my suspicions are right, you have probably worn the same underwear for days. So, unless you prefer the couch, or want to go home, panties and a nightie for you tonight.” She could feel her excitement building as she ad-libbed her proposal.

“Come on Jesse, don’t freeze up now. You’re the one who brought it up, and besides, how would you ever get your hands on some panties on your own? You want me to drop you off at Walmart or something?”

Jesse did actually listen to her and thought it probably made sense, but there was still that small voice, softer now but still saying no to everything it seemed.

“You know what, I’ll give you the panties. Rick was dropping a pretty strong hint about wanting to see you in them.” Good, that got his attention, she noticed and a small little smile showed her satisfaction.

Why does this always have to be so damn confusing, he was thinking while staring at the floor. But she was right about him wanting to please Rick, and the panties would be a surprise for him. “Okay, you’re right. I need to try it and get it settled one way or the other.” The big breath and slow exhale clearly showed the stress and worry all of this had been.

Amanda did understand how hard this was for him, but thought it best if he just pushed through and tried things out. Maybe he would find the answers, but until he tried, it would always be like this. However, she also wanted desperately to see him in the pink lace panties she already had in mind, she admitted truthfully to herself.

“Ready for a movie,” she asked as if nothing unusual had ever happened.

“What about popcorn?” Jesse smiled.

“That too, come on let’s go make it.” Taking his hand, off they went. Two innocents experiencing life and exploring the unknowns.


End Part Two

Ben Esra telefonda seni bosaltmami ister misin?
Telefon Numaram: 00237 8000 92 32

Bir yanıt yazın