Discovering Mistress Sarah's World Pt. 07

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
oneguy4fun
oneguy4fun
1,212 Followers

Mistress Sarah made Josie slowly turn for her and Miss May. She admired her thong clad pet. The shiny metallic top and pink lipstick were a bright and fun combination. Mistress Sarah complimented, "Mmmmm. You look so sexy Josie."

When his ass was facing the girls, Miss May laughed at how the small v-back thong barely contained his large clittie. Miss May commented, "Be careful how you lay down princess. The boys might get all excited if they see your clittie hanging out like that."

Josie blushed. Being in a bikini was a new experience for him. He started to feel that strange excitement that he felt the first time Mistress Sarah had him slide on panties. This was another facet to his new feminine life that Mistress Sarah and Miss May were forcing him into.

Mistress Sarah had Josie put on a pair of clear heels. When Josie stepped into them Miss May rubbed his ass and said, "Your a beach bombshell."

"Thank You," replied Josie. He felt a bit self-conscious and vulnerable in the skimpy outfit. Her compliment helped put him at ease.

Mistress Sarah grabbed her pool bag. "Ready to go girls," she asked.

Josie looked at her with a panicked expression. "Do I have to go to he asked?"

"Of course princess, it's girls day at the pool."

"Please can I stay here Mistress. Please!" Josie begged desperately. "I will be so embarrassed."

"Don't be silly," said Miss May. "You have a beautiful figure."

"But my outfit is so skimpy. Everyone will know I am a man dressed in a bikini."

Both girls laughed. "Oh Josie," said Mistress Sarah in dramatic and mocking tone. "There is nothing manly about you. You are my girl now. They may think you are a sissy but certainly not a man."

Josie blushed. He was just about to resign himself to the embarrassing fate, when Mistress Sarah said, "You can stay behind sissy but you must stay in your bikini and heels and I expect you to make lots of appearances out on the balcony. May and I will situate ourselves so that we have a good view of the balcony."

May smacked his ass and said, "That's right sissy-bitch. You need to strut your slutty little tush for us."

"Yes. Mistress. I will do that. Thank you," replied Josie in a happy and relieved tone. It would still be embarrassing for him but it was much better than walking down to the pool in a bikini.

"Clean up while we are out sissy-maid. I want every room sparkling clean when we return or you'll get a nice hard spanking."

Mistress then grabbed Josie's wrist and led him out onto the balcony. The pool was quite a distance from where they were at. "Wait here and look for us Josie." She handed him his cell phone. Keep this handy princess. We'll be calling your frequently with instructions and tasks to do."

Josie waited on the balcony until he saw the girls take their seats at the pool. Once situated, they both turned and waved at him. Josie wave back. His phone vibrated and looked down to see a text from Miss May. It read, "Get to work maid."

Josie went to work cleaning the house while the girls relaxed at the pool. True to her word, Mistress Sarah called him every now and then and ordered him out onto the balcony. She would make him wave and shake his body and wiggle his ass. With Mistress Sarah and May looking his way and laughing, there were always a few people at the pool who would look over to see what was going on. Josie was conscious of this and was a bit embarrassed. He took some comfort in knowing that from the far distance no one would recognize him or even guess that he was guy.

On one particular instance, two guys were talking with the girls when Mistress Sarah called. She ordered Josie to flash her tits and wiggle them for the guys. This was a bit tricky since he was wearing falsies. Josie managed to pull his bikini top to the side and hold the falsies in place while he jiggled them. He could see the guys at the pool raise their hands and cheer.

"Good girl," said Mistress Sarah. "Now shake your ass for the boys like a whore." Josie turned and wiggled his ass.

"That's it slut. The boys are loving the show. Maybe I'll invite them up later for some fun Josie. What do you think? "

Nervously Josie responded, "uh...I don't know if I'm ready for that Mistress."

"It's all fantasy right Josie. Just say yes," demanded Mistress Sarah..

"Yes Mistress." Josie's cock swelled in his bikini bottom, knowing that she was exerting her power to make him admit humiliating things.

"Yes what," asked Mistress coyly.

"Yes, I would like it if you invited the boys up for some fun later."

"Mmm that's nice Josie. You would suck their cocks wouldn't you?"

Josie was blushing. He knew the answer that Mistress expected. "Yes Mistress. I would suck their cocks." Josie wondered how much of the conversation the guys could hear. He imagined they were getting excited, thinking that a girl was going to give them a blow job. He hoped Mistress Sarah was just teasing them and him.

"You're a whore Josie." Mistress Sarah giggled. "Get back to work."

That was the last call Josie received. When Mistress Sarah and May returned Josie was relieved to see that no one else was with them. May squeezed Josie's ass when she walked in and said, "Nice job slut. You had those guys all excited. Your training has definitely paid off. Pretty soon you won't even remember what it's like to be a guy."

Josie wondered how true that statement was. In the back of his mind he was still pondering whether or not he should move in with Mistress Sarah permanently. She was amazing, beautiful, and fun. Not to mention all the fun he would have serving Miss May, Mill, and Mistress Sarah's other friends. What made him nervous was his feminine transformation. It was fun and exciting, but totally losing his manliness scared him. He was very confused and unsure whether or not his infatuation with Mistress Sarah would win out over his fear of losing his manhood.

Mistress Sarah was not confused at all. There was no doubt in her mind that the only reason Josie would be leaving in a few days, would be to pack up his belongings and move in with her. She had already determined that she wanted him as her 24/7 slave and fuck toy. She knew that he was weak and could not resist her. It was just a fun game for her now. She would toy with him and tease him and play all sorts of mind games with him and finally get him to beg to stay with her. In fact she had many things planned over the next few days that would break all his limits and transform him into a complete slut and slave for her. She had always wanted a blank mindless fuck toy to play with. It would only be a matter of time before Josie would fit that bill for her.

Mistress put her first mind game into motion. "Josie, sweetie, I want you to take my laptop out onto the patio and type up your resignation letter."

Josie's heart pounded and he looked at her a bit shocked at the request. Mistress Sarah responded to his expression, "It's just an exercise princess. I know you haven't decided just yet, but I want you to write the letter anyway. See what it feels like to get it on paper, o.k.?"

"Yes, Mistress,"

"Good girl. May and I are going to take a shower. You can show it to me when you are done."

Josie sat at a round metal table on the balcony and typed away. The small overhang on the balcony provided little cover from the hot sun. He was glad to be only in a bikini.

Ever since Mistress Sarah had brought up the idea of him moving in with her, Josie had been going back and forth in his mind, debating whether or not he could really do it. Now as he wrote the letter it made him think even harder about it. He wrote the letter very general with sentences like "It's been a pleasure working here' and 'For personal reasons I am leaving."

When he finished writing it, he printed it. Before he could get up to get the letter, Mistress Sarah walked out onto the balcony wrapped in a fluffy white towel. Her hair was also wrapped in a small towel. Josie thought she looked sexy even in just towels. In her hand was Josie's letter that she retrieved from the printer. She was reading it while she walked onto the balcony. It was very brief so it only took a few seconds to read.

"Lovely letter Josie," complimented Mistress Sarah. She placed it on the table with a pen. "Now sign it," she demanded.

Josie looked up at her. Her look was unwavering. "Yes Mistress." He took the pen and signed it with his real name. He couldn't help but think that he was actually signing away his life at that moment. It was a scary but exciting feeling.

"That name looks so silly now doesn't it Josie. It might be the last time you sign it sweetie," laughed Mistress Sarah. "Now imagine that this was for real. How does it feel Josie? How does it feel to not have a job and to be 100% committed to serving me?"

Josie knew the Mistress Sarah was mentally manipulating him. He could feel her power and determination to control him and it excited him. His cock swelled in its bent position in his bikini bottom. He could feel the heat of his cock against his thighs. The thin thong string barely held it in.

"It is exciting Mistress. A little scary but very exciting," he admitted.

Mistress Sarah had him stand up. Then she pulled his bikini bottom down just enough that his cock came free. It instantly swelled into a fully hardened state. Mistress Sarah giggled. "That's was I thought."

She held his hard cock firmly in his hand and said, "Now, just for fun Josie, write me another resignation letter. This time tell the truth. Write how you met a Mistress and how it changed your life and that you realize your new calling in life is to worship the female and serve a Supreme Goddess."

Mistress Sarah raised her finger to Josie's lips. It was covered in his precum. Josie sucked on her finger. Mistress Sarah whispered, "Mmm....you are excited by this new world of yours, aren't you?"

"Yes Mistress," replied Josie.

Mistress Sarah giggled. "Get to work Josie. This next letter will make a nice addition to your sissy journal."

The second letter took longer to write. With his cock free, Josie could not help but stroke his cock while he wrote his resignation letter and about his new life. He could not believe how excited he was getting from imagining serving Mistress Sarah as a full time slave. At one point he got so excited and aroused that he had to stop writing, stop stroking his cock and he had to concentrate on not cumming. He was close to the edge but he managed to calm himself down.

This time when Mistress Sarah walked onto the balcony with his letter she had on a simple summer dress. Josie immediately admitted, "I am so horny Mistress. My clitty is aching."

"Your horniness is evident in this letter. It is very long and detailed."

Mistress Sarah handed him the letter and pen again. Josie signed it. Mistress Sarah leaned down and kissed him on the cheek. She squeezed his hard cock and said, "Look how hard and wet your clittie is. I think you want this more than me Josie."

"I do," admitted Josie.

"Then it's settled. The only question now is which letter do I send to your boss?"

"You can't send the last one Mistress. I will be so embarrassed!"

"But it is the truth princess. Besides, you will be leaving your job. Who cares what your boss thinks."

"Please, no," pleaded Josie. "I don't want them to know about this part of my life."

Mistress Sarah laughed. Her laughter was filled with arrogance and dominance. "You are a weak little slut Josie. You still have a few more days here before I send you on your way to pack all your things up. Be a perfect little princess for me for the next few days and maybe...just maybe I'll let you hand in the first letter."

"Thank you Mistress. I will be a good princess. I promise."

"Gather up your things now slave. It's time for you to get a shower." Mistress Sarah walked off the balcony with both his resignation letters and a smile of success.

Josie's heart was pounding. Everything happened so quickly. He felt weak and helpless in Mistress Sarah's presence. She had a power over him that he could not explain or resist. He was now a permanent slave to Mistress Sarah. His cock was harder than ever as he thought about it. He wanted to desperately cum.

Inside, the girls had a good laugh when Josie stripped for them. "Josie darling, you've developed sexy tan lines," giggled Miss May. "Now there is no denying that you are sissy girl.

Josie looked down and sure enough there were two small white triangles on his chest. The little bit of time he spend out on the balcony in the sun was enough to give him a bronzed tan. The tan lines from the bikini bottom were less noticeable as his lower body was hidden from the sun most of the time.

"Turn around and let me see your ass." Demanded Miss May. She gave it a good hard squeeze. "Nice ass Josie but no tan lines. We'll have to work on that."

Mistress Sarah added, "by the time you leave, I want you to have a dark tan with clearly visible tan lines. Do it or I will send in your naughty resignation letter."

"Yes Mistress," said Josie. He knew he did not have a choice.

CHAPTER 19 Introducing Neil

It was only his third morning awaking at Mistress Sarah's house but it was already feeling like a ritual to Josie. He awoke in a silk gown with a raging hard-on and completely aroused just like the other mornings. And just like the other mornings he could not wait to crawl into bed with Mistress Sarah and Miss May.

Josie crawled to the foot of the door and discovered a note and lingerie waiting for him. The note read,

'Sexy lingerie for a sexy pet. Put it on and come join us.'

Josie held up the delicate items. It was a matching bra and panty set along with black stockings. The bra was purple and adorned with ruffle lace and a purple satin bow. The panty was mesh at the top. The crotch area was similar to the bra, adorned with ruffle lace and a satin bow. Garter straps were built into the panty.

Josie thought the set was super sexy and could not wait to put it on. He quickly changed into the items. He felt feminine and sexy in the soft lingerie. His 'clittie' was fully aroused and almost dripping. The black heels he wore Saturday night were also sitting by the door. He strapped on the heels and crawled into the room.

Josie was excited to hear moans and see movement on the bed. He could not wait to join the fun. He remembered Mistress Sarah saying the day before that she was in the mood for a good hard fucking. Josie hoped this would be his lucky moment. His clittie throbbed even harder at the thought. 'Perfect timing' he was thinking but then he noticed one of the moans was a bit deeper than usual.

Josie froze when he realized that Miss May was not the other person in the bed. It was a man, which Josie presumed was Mistress Sarah's live-in slave and boyfriend, Neil. Wanting to retreat, Josie quietly turned to leave but it was too late. Mistress Sarah had noticed him.

"There's my pretty pet," she exclaimed happily. "Come on over kitten. Come meet Neil."

Josie crawled slowly. Mistress Sarah encouraged him on. "Don't be shy kitten. Come over here."

Both Mistress Sarah and Neil sat-up in bed. They were naked but covered from the waist down by the bed sheets. When Josie was at the side of the bed he sat up on his knees. Mistress Sarah did a quick introduction. "Neil meet Josie. Josie meet Neil."

The introduction was hardly necessary. They had never met in person but both knew each other through the many online exchanges they had together with Mistress Sarah.

"Nice to finally meet you," said Neil in a bold tone.

Josie replied, "hello," in a much meeker tone. He suddenly felt silly and awkward using his feminine voice in front of a man.

"Do you like your new lingerie," asked Mistress. "It fits you well."

"Yes. Thank you. It is very sexy." Josie liked the lingerie but felt embarrassed in front of Neil.

This was not how he expected things. He had always imagined himself one-step above Neil in Mistress Sarah's hierarchy. After all, Neil was feminized long before Josie. When they were on-line Mistress Sarah often let Josie be dominant to Neil. Neil had even referred to him as 'Master' on occasions. Now the tables were turned. Josie was feminized and kneeling before Neil. Josie was at the very bottom of the submissive hierarchy.

"Turn around kitten, so we can see you from all sides," ordered Mistress Sarah.

Josie slowly turned on his knees. When his back was to them, Mistress Sarah commented to Neil, "Doesn't she have a cute little ass. She will make a good pet and slave for us, don't you think?"

Neil replied, "Yes, she is sexy. She will be a great addition to the family."

Mistress Sarah made Josie turn to the front again and then she said, "Very nice pet. You should thank Neil for the lingerie. He is the one who picked it out and bought it for you."

Josie blushed and was embarrassed to know that he was wearing lingerie that a man had bought him. "Thank you," he said meekly.

Josie had noticed how Mistress said 'our pet' to Neil, implying that he was not only a pet and slave to Mistress Sarah but also to Neil. He was also keenly aware that Neil was referring to him as 'she'. Having another man disregard his manhood brought on a new level of embarrassment to Josie. Josie felt incredibly submissive and inferior kneeling before Mistress Sarah and Neil. It was a strange and awkward feeling.

He also knew that Mistress Sarah was enjoying the moment and getting off on putting him in this unexpected and awkward predicament. He could see the devilish pleasure in her eyes and this excited him. Despite his embarrassment, his cock was aching hard.

"You are just in time princess. Neil was about to fuck me. Now you can watch."

Josie's heart dropped with disappointment, "but I thought I was going to fuck you," he said dejected.

Mistress Sarah laughed dramatically, highlighting how absurd Josie's statement was to her. "Oh Josie. Josie, Josie, Josie. You didn't think I meant you would get to fuck me, did you?" She laughed again. "Look at yourself princess. You're wearing panties and a bra. You even have heels on. You're much too soft and pretty. I'm in the mood for a hard fucking from a real man, not a prissy little sissy girl.'

Mistress Sarah pulled the sheet down from Neil's waist and made him get up on his knees so that Josie could see his cock. His cock was in a semi-hard state. Mistress Sarah started to stroke it. While she stroked she said, "This is a real cock Josie. See how he has control. He can sit next to me without being erect. He's not weak like you, walking around with a hard clittie all day."

Josie felt even more submissive and in the twisted world that he was now a part of, he was enjoying Mistress Sarah's humiliating words. She was right, that he was weak. He did not know how Neil could not be hard sitting next to Mistress Sarah in bed.

Neil's cock finally grew hard in her hands. Mistress Sarah commented, "Look how big his cock his Josie. Isn't that a nice big cock?"

"Yes," replied Josie.

"Maybe if you are a good girl, I'll let you suck it. You will be a good girl for me, won't you kitten?"

"Yes, I will be a good girl for you." Josie felt as if his answer to that question implied that he wanted to suck Neil's cock. Josie did not want to suck a man's cock but he was in awe at how Mistress Sarah masterfully manipulated the conversation in that direction.

"Pull out Joe's cock for me princess. Stroke your man's cock while I stroke Neil's."

Josie lowered his panties and started stroking his cock. He was excited that Mistress Sarah was going to play the mind game with him of stroking a man's cock.

"That's it Josie. Let's stroke these boys cocks together."

Josie slowly stroked his cock in the same rhythm that Mistress Sarah was stroking Neil's.

oneguy4fun
oneguy4fun
1,212 Followers