I wear Panties for I am a Sissy

I Wear Panties for I am a Sissy
By Sarah Goodwoman.
Author’s Notes: I would like to thank everyone who has been helping me to better hone my writing skills. To the people who have edited my works thank you, and all the people who gave good advice about how to better my writing thank you. Also, this story has a special thanks to my oldest sister for her writing helped inspire me to be able to write Sally.

Cecilia Hawkins was driving over to Sally Crawford’s house for afternoon tea. She could not wait to have some of those delicious scones with clotted cream and jam. Cecilia was happy that Sally has recently opened a new bakery, Sweetie Sally’s Sweets so she could get those scones anytime. Having easy access to them was great but it was even better having them with her dear friend, Sally. Cecilia did wonder where Sally had the time to do open the bakery, for she also owned Sassy Sally’s Spa and Salon, a beauty salon which cater to both girls and ‘gurls’, and Sally’s Sensational Speakeasy, a trans friendly bar. Cecilia concluded that Sally threw herself into more work to deal with her breakup with Faye. She then jokingly wondered if Sally would ever open a business without her name in it.

Cecilia rang the doorbell and was greeted by a big hug and an even bigger smile from Sally. Then Sally kissed her friend on the cheek and told her to come on in. Sally took her coat and told Cecilia to make herself at home in the dining room.

Cecilia marveled at how great a hostess Sally was; she could make anyone feel welcome. This was because she had a genuine interest in other people and that made whoever she was talking to feel special. Sally loved to find out anyone’s life story as she believed that knowing how a person views their past told you who they are and where they are going.

Cecilia sat in the dining room and Sally came out with a silver serving tray with the afternoon tea on it. As Sally was pouring Cecilia her tea the hostess asked her guest how she had been. Cecilia smiled and said she was fine, then quickly changed the topic by mentioning how much she loved that serving tray.

Hearing her short answer along with how she loved the serving tray added to Sally’s concern; she knew that no one loved a serving tray. Sally did want to see her good friend as it had been a while since they had quality one-on-one time but that was not the reason she had invited her over. Sally’s good friend Ruby Rose told her that she saw Cecilia and was called a slut by her. It was just strange for those two had really hit it off when they met a couple of months ago, so Sally needed to know why

Sally sat down after pouring her own tea and while offering cream or sugar to Cecilia asked her what was wrong. She might be concerned about how Cecilia talked to Ruby but that could wait. She needed to know what was bugging Cecilia.

“Nothing’s wrong, dear,” Cecilia responded, “now tell me where you got that serving tray - like I said, I love it.”

Chapter 2

Cecilia should have known she was not going get Sally to quit inquiring about what was bothering her, but was too embarrassed to talk about it. The truth was, Cecilia wanted a sissy as a boyfriend. She had become fascinated with sissies ever since Sally’s ex-girlfriend, Faye, had her come over to a party. That was where she had been introduced to the subculture of sissies.

Cecilia had marveled at how hyperfeminine the girls were. She also enjoyed how readily sissies accepted and took on the role of the woman in a relationship. Cecilia admired how in-tune a sissy was with other people’s wants and needs. She swore once they knew a person, a sissy knew what that person would want before they did. Plus, they were all just so sweet.

At first, Cecilia was uncomfortable at the party; she wished that Faye would have told her exactly what the party was. She was going to leave right away but Sally, being the ‘hostess with the mostest’, insisted that she stayed. Cecilia did not want to offend Sally so she decided to stay for a little while and lthen eave.

Cecilia made camp in the corner and nursed a glass of white wine. At first all the giggling she heard from the ‘girls’ made her a little uneasy. She assumed it was forced and they were making a mockery of women. Then Cecilia heard how natural it was and started to see their actions differently. These ‘girls’ were so happy and celebrating that they could giggle and be who they were without judgement.

Cecilia’s mind started to be more open to her surrounding for she was feeling more at ease around these people. She noticed the clothing and makeup. Just by seeing what the ‘girls’ were wearing, she could tell they took great care in picking out their outfits; those sissies were proud of how they looked. They were dressing for themselves and not to impress others. She knew they also wanted to impress others but that was a secondary concern to them.

Finally, she started to hear the sissies around her talking. She noticed that almost all of the ‘girls’ mentioned that how they could not hide who they were once someone with a strong personality pointed out they were a sissy to them. Then the next thing they said was how happy those ‘girls’ were when they found out the big sissies they were. She laughed to herself when she heard one of them talking about how she was a biker before being put into panties.

As she was about to take the last sip of her wine and leave the party, one of the ‘girls’, dressed like a 50’s style housewife in a sleeveless shirtwaist dress with a pearl necklace, came up to her and asked her if she needed a refill. Cecilia waited a second to give a response and was going to respectfully decline when the ‘girl’ told her not to be silly, stay and the two of them could chat some. Cecilia was surprised at her server knowing what she was about to say before she did, so she agreed.

Her new friend came back with two glasses of wine and introduced herself as Ruby Rose. They started to chat and Cecilia found Ruby was a delight to be around. Ruby was upbeat, confident, charming and she listened. Cecilia was pleased that Ruby did not make the conversation all about herself but about also about her new friend. Ruby was talking with her, not at her. Cecilia found it refreshing that a guy, even if the guy was a ‘girl’, was so good at communicating.

During their conversation, a couple of Ruby’s friends came over to see her. To one of them Ruby mention that she was with a man this past weekend and she was such a whore. They both giggled and Ruby’s friend said she knew.

Hearing the ‘whore’ comment made Cecilia a little sad; she knew she was getting a crush on her new friend and her new friend was into men.

Cecilia also knew it was just a fantasy for she had a man and also if she did not, she could never date a “sissy,” She then asked herself if she could. Nah, there is just something about a man being all man. It might not be as rewarding with the personal connection, but a real man just got her blood going. Getting the blood going was worth the sacrifice of not feeling close to her man so it was no big deal. Personal relationships were what woman had girlfriends for.

Cecilia withdrew from the conversation and Ruby asked her what was wrong. Cecilia was trying to figure out how to answer the question without embarrassing herself or Ruby. While she was trying to find the right words, Ruby spoke. “Hon, I am a lesbian if anything,” she said. “Men are for fun, women are for relationships. He was just for fun and we were playing.”

Cecilia turned beetroot red; how did Ruby know Cecilia had a little crush on her? Also, she was a little shocked at just how upfront Ruby was with her sex life. After she got over the shock, Cecilia found it refreshing how easily Ruby spoke about it. It broke down some of Cecilia’s inhibitions

All during their time together Ruby looked out for Cecilia’s wants and needs. She got them from standing in the corner to sitting down, made sure that Cecilia’s glass was always filled and got them a plate of hors d'oeuvre.

“Cecilia, dear,” Ruby smiled as she put down the plate, “the crab puffs are all for you. I’m just saying this so you can savor them and not rush to eat them.”

Cecilia wonder how Ruby knew that she loved Sally’s crab puffs. Then she remembered that she quickly mentioned it a couple of hours ago when someone walked by them eating one. They were enjoying each other’s company and Ruby was so supportive of Cecilia. Ruby was so happy to hear that her new friend had a great man.

Ruby was upfront and admitted she was a little disappointed about Cecilia having a man, for she wanted to try to get to know Cecilia better, but still wanted to be her friend. Cecilia loved hearing that and knew that the two of them would stay in contact. While the two new friends were talking, Faye pulled Cecilia away to have a chat.

Faye wanted to hear all about the budding relationship between Cecilia and Ruby. She also wanted to sell Cecilia more on how great sissies were. Faye loved sissies for the same reasons that Cecilia was fascinated by them. Cecilia became aware of how much she would like to be in the leadership role of a relationship and told Faye how special she felt just by spending time with Ruby. Then Faye brought up how the intimacy came from a spiritual place instead of the physical and feeling special came from that connection starting to form. Cecilia knew that she would adore that kind of a connection.

Even with Faye convincing Cecilia about the joy and benefits of having a sissy boyfriend, Cecilia was so in love with Neil, her man. Faye told her not to worry as all men had a sissy in them, all that Cecilia needed to do was to bring that ‘girl’ out in him. Faye then informed Cecilia she would tell her how to do so if she ever came to her senses and wanted the best of both worlds from her boyfriend.

After the conversation, Cecilia went to find Ruby to exchange phone numbers but she was nowhere to be found. Faye had Cecilia away longer than was expected and Ruby was gone. Sally saw her friend scanning the room and asked her what she was looking for. Cecilia desperately said her new friend Ruby. Sally was happy that Cecilia made a connection with someone, for people could never have enough friends, so she was sad to inform her that Ruby left for her ride wanted to get home. However, Sally did inform her that Ruby wanted her to know that she often went to Sally’s Sensational Speakeasy.

Cecilia left the party a little upset that she did not get to spend more time with Ruby for she would never go to the Speakeasy. She was not going to asked for Ruby’s number for Ruby would have told Sally to give it to her. Cecilia also was not going to be upfront and tell Sally to give Ruby her number, for that would send mixed signals.

Chapter 3

Sally knew that she was not going to get anywhere in finding out what was on her friend’s mind with a direct line of questioning. Even with the doubt that it would give her any information Sally had to be upfront with her friend at first. Sally did not want to have to pry to find out what was wrong with her dear friend.

Sally did what she did best; learn about her friend. Talking about what was new in their lives would be how Sally found out what was wrong with her. It might tie into why she called Ruby a slut. Sally asked Cecilia how Neil was doing.
Cecilia sighed.

“Sally, he broke up with me,” she said.

Sally was starting to get a picture of what happened with Cecilia and Ruby. Cecilia must have been mad and in an offhand manner said ‘slut’ when Ruby was talking about her sex life. Ruby’s fantasy was being a whore, to get paid for sex. Given how open Ruby was about her sex life, she might have talked about ‘turning a trick’ and that led to Cecilia saying ‘slut’.

Sally knew her friend was not mean and would soon clear this up by explaining to Cecilia that Ruby never really turned any tricks, it was all part of play. Cecilia would learn that Ruby was hooking up with a regular man and he would ‘pay’ her for sex. They were not a couple, just sex buddies. Neither of them had been with anyone else since Ruby turned her first ‘trick’ with him.

That explanation could wait, however; for now she had to make sure Cecilia was coping with the breakup.

“I am here for you dear,” Sally said while reaching out to give Cecilia her hand. “I wish you would have called me about it. I would have made sure I had time for you.”

Hearing her friend’s sweet comforting words and Sally being a sissy made Cecilia want to talk about what happened between her and Neil, how he had made a mountain out of a molehill about the gift she gave him. It would make her feel better and Sally could help her find a sissy to date.

“Neil acted irrationally when I bought him the cutest bra and panties,” Cecilia told her friend.” He told me I was crazy and just got up and left, he didn’t say another word to me. That jerk never returned my phone calls. How could he be that mean to me?”
Sally was confused - why would Cecilia buying some sexy lingerie to wear for Neil provoke that reaction?

“Really, you bought some sexy lingerie to wear for him and he just disappeared like that?”

Cecilia laughed and that made Sally even more confused.

“Oh, no dear, I should have been clearer. The bra and panties were for him to wear. Men, sometimes I just don’t understand them.”
Sally shook her head and put her hand on her forehead in disbelief.

“Why would you do that, dear?” she asked. “Neil is all man.”

“Oh, you remember that party you and your ex, Faye, had,” Cecilia responded. “Well, I found out that night I wanted a sissy. Faye told me that all men had a sissy in them so I just wanted to bring that wonderful ‘girl’ out in him. I guess he was not ready to be more in touch with his feminine side. Still, he could have returned my calls. That was just rude of him.”

Sally rolled her eyes. Faye had obviously not done enough to explain sissies to Cecilia. Faye was lost in the all the roleplaying and Cecilia took it at face value. Sally was irked at her ex; Faye had told her that she explained the party to Cecilia.

“Dear, it was not rude of him to not call you back,” Sally responded, “he probably thinks you’re crazy. Giving him panties and a bra to wear was also an insult to who he is. In his eyes, you were telling him he was less of a man. You should have never have done that. Listen, I feel like I’m to somewhat blame for this. I should have explained that most people at the party were roleplaying, that they said things which they did not believe as gospel and most of it was not true.”

“It’s simple, really,” she continued. “The clothes do not make a person. Putting me in army fatigues wouldn’t make me a soldier any more than putting Neil in a bra and panties would make him a sissy. I wear panties because I am a sissy, not I am a sissy because I wear panties. Do you really think that one day I was a manly man and somehow panties were put on me and I became this fabulous person who is in front of you? How long have you known me, dear?”

Each time Sally said sissy she put air quotes up. It was a sign to her friend that she was not really a sissy, also sissies did not really exist. Well, they did, but not how they were portrayed at the party. Sissyhood was more about how a man expressed his desires to be feel and be treated as a woman.

Cecilia had been friends with Sally for over ten years now. They met whilst in college and she did not find out that Sally started life out as Saul Crawford until almost 2 years after they became friends. It was not because Sally was ashamed of being transgender; she was proud of how strong she was in being able to live her life how she should, as a transgender woman. She would not tell people until they needed to know. Sally wanted people to judge her for who she was at the time, not her past. As her circle of friends grew she found out that she needed to tell people sooner. Talking about her experiences as Saul made her realized her past did make her who she was and she needed to tell people for them to really appreciate who she was and to feel a closeness to them. That revelation led her to becoming more of a people person.
Sally was always outgoing, but before gaining the knowledge of truly knowing people it was more because she wanted to be recognized. She felt that the more people knew who Sally was legitimized her womanhood. She became a people person because telling people about Saul was what truly humanized her to others. She wanted to do the same for others, she wanted people to know she loved and appreciated that they were all each unique individuals.

“Dear,that was one thing about the party I found funny,” Cecilia said, “you saying you were a sissy. I just thought that you really embraced womanhood after someone helped you find that girl inside you. Faye talked about how sweeter you became since she became your girlfriend and how you were going to start to slow down in your business life to devote more time to being the doting housewife. I guess that’s why you opened up the bakery, to get over the breakup of your relationship with Faye”

“Oh great,” Sally thought, “now I have to deal with talking about what happened with me and Faye.” She did not want to handle that topic today for it still brought her pain thinking about it. This was because the two still loved each other but wanted different things out of a relationship. Faye wanted Sally to be more of a traditional wife when they got married but Sally was a modern woman and wanted to keep expanding her little business empire. Finding out those different expectations made Sally learn a painful lesson; sometimes love is not enough.
She corrected Cecilia.

“I am not a sissy, dear, I played that role for Faye for she enjoyed it when we did some roleplaying. Like I said, there was a lot of roleplaying going on at that party. I might have become sweeter when Faye was around, but that was because I love her and it wasn’t all the time. A person in a good mood will always be sweeter. Us breaking up was not because of the bakery, the bakery was the cause of us ending our relationship. Faye wanted me to scale back on my business ventures and I am too much of an entrepreneur to not be planning on how to better my businesses or be opening up new ones.

“Plus, those businesses mean the world to me. All the ‘girls’ who work there are now like my sisters and daughters. I am doing my little part in helping the transgender community by having good paying job which ladies like me can have. I do scale back on my other ventures when I open a new one, because I also want to have a balanced life and I have someone who can manage the one which I been putting my time in. That is why I am not at the salon that often anymore, Tracy’s doing such a great job at running it. That’s also why I was not at the bar the night you stopped by, Lisa has got that place running better than I ever did. Speaking of you stopping by the bar, why did you call Ruby a slut? That really hurt her feeling and so out of character for you.”

Cecilia was stupefied to hear that she had hurt Ruby’s feelings by calling her a slut, that was the last thing she wanted to do. Cecilia was trying to flirt with Ruby and remembered Ruby calling herself that while laughing with her friend about being with a man.

She was a little pensive in her response, she did not know how to say that she liked Ruby.

“Sally, I did not mean to hurt Ruby’s feelings. I just remember her calling herself that at the party while talking about one of her sexual conquests with some random guy. I was trying to show her I’m fine with her being a slut. No sorry, it does not matter if I am fine with her being a slut, I like her being a slut. No, not that either. I mean I like that she has a healthy appetite for sex, I like her. I just wanted her to know that I liked her and didn’t care about her past.

“I might not be close to understanding what a sissy is, but spending time with her was great. She made me feel special just by being herself and I know I made her feel the same way. I want more of that.”

Sally was so relieved and happy that she now knew what had happened and would easily be able to clear this up. Her happiness increased for she was going to be able to play matchmaker. Ruby liked Cecilia and that was the main reason she was intensely hurt by being called a slut by her crush. Sally got excited for she loved to see two people get together and she was going to see the start of a hopefully beautiful relationship tonight.

She also made a little mental note to call Neil. She believed that Cecilia and Neil need to part company on better terms.

The other reason was Ruby’s fantasy was not being a slut, it was being a whore. That was no random man, she had not been in a serious relationship or even dated any woman in a while so she had been hooking up with the same man for over two years. They play out a scenario where George, that man she has funtime with, acts like a ‘john’ and approaches Ruby at the bar and would then make an indecent proposal. To her, there is a difference between a slut and a whore. A slut just liked to have sex with many different people, while a whore like to be paid for having sex with many different people. It made her feel amazing to get paid to give someone pleasure.

“Honey, it was all a misunderstanding,” Sally told her friend. “See, Ruby is not a slut and would never call herself one. She is a whore, well, she is not really. Her fantasy is to be a whore - it’s just a fantasy. I’ll let her explain later tonight when you see her.”

“I’m not seeing her tonight,” Cecilia said quickly. “I can’t face her right after being so mean to her. She really doesn’t know me and I would feel so embarrassed.”

Sally got a roguish grin on her face and that made Cecilia a little suspicious. She knew that Sally had just formulated a course of action which would make Cecilia see Ruby tonight. She knew that her premonition was true when she Sally spoke next.

“We’re going to make this afternoon tea in a girls’ day together and then a girls’ night out. I need to go to the club to make sure the girls know I’m still alive and the name did not change to Lisa’s Lounge. Plus, Ruby likes you so you two need to see each other and clear this up as soon as possible. Don’t worry I be at your side when you two aspiring lovebirds reconnect. She’s such a nice person. Fair warning, she is not always a sissy, but is always the kind caring person she is as Ruby. I’ll let her explain it in more details to you. You know that I will not take no for an answer so just say yes.”

After hearing that Ruby liked her, Cecilia gleefully accepted the fact that she was going out with Sally tonight. She was looking forward to spending time with Ruby. She did wonder about Ruby’s non-sissy persona; would she also enjoy spending time with Ruby when she was not Ruby. Was she transgender like Sally, was her other persona a male? She knew the only way to find out the answers to those questions was to get to know the wonderful person who was Ruby.

“All right, I’ll do it,” Cecilia said jokily, “but you owe me big time, Missy.”

Sally laughed and with her quick wit came back with “I’ll pay you back by being your maid of honor when you two get married.”

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