Be Careful what You Ask For

Story Info
His fantasy becomes reality and her dreams fulfilled.
2.3k words
4.41
22.5k
9
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

This is a continuation of a story that began when a new neighbor moved in.

Chapter two - Be careful what you ask for

He had always imagined what this would be like. He thought it was just a fantasy, but it was actually happening! A beautiful woman (whom he barely knew) had enticed him into signing a contract which ultimately stated that he was her slave. Of course, we was more than willing, so not much enticing was required. Now, here he was, standing in her living room, dressed in panties and a camisole; a dream come true.

Bailey smirked with a tantalizing grin as she contemplated her next move, her next demand. Her mind was racing with anticipation and her body couldn't help but react. After all this was new territory to her as well. Both he and Bailey were excited beyond anything either had experienced. And Bailey was very happy to be in the drivers seat!

"Well," she said, finally breaking the short silence, after having tucked his rigid pole back into his silky, nylon panties. "Let's see if you are really up to obedience, as the contract states." He remained silent, overwhelmed by the newness of the situation and the eager anticipation of her statement. "Tell me who you are." She stopped short of adding any description to her statement, wanting to hear his idea of what he was thinking.

"I'm mistress Bailey's sub. Her own personal sissy slut," he added in a upbeat tone.

"Mmmmm, I like the sound of that! Sissy slut! We shall see, my little slut."

She got up from the chair and slowly walked towards him. As she approached, she seemed to be studying him up and down. She walked around him and reached out so that her soft hands gently touched his waiting body. His shoulder shuddered slightly as her hand moved to his silky camisole that covered his back. Without a word she continued to lightly caress and tease her new plaything. Down from his camisole to the edge of his waist-high panties, her soft hands wandered. The slow movement was driving him into oblivion. He had fantasized about this for years and he closed his eyes as he enjoyed the moment. She slowly rubbed his tight ass cheeks through the soft material. "I am going to use this hard body like you can't even imagine. Does that worry you, my whore?" she practically whispered.

"I'm not sure, I mean, I don't think so mistress." he replied.

"I have always wanted someone to follow my every command!" she said in a louder tone and as if she was just thinking out loud. "I had a feeling about you when we first met. Like you were more than being nice. Like you wanted to serve me. And when you showed me your panties putting up that picture, I was convinced. I've been talking to my girlfriend about you all week and she agreed that I was probably right. She wrote the contract, which you failed to read. She is a co-owner, by the way. And she is fucking kinky! She has done some things to me, well let's just say you are going to find out very soon."

At that, she walked to the table and picked up her phone. A quick click of the camera and she had sealed his fate. She fiddled with her phone a minute or two and then it rang. "You got it? Didn't I tell you? I know, he, I mean she, is going to be so much fun. Thanks for convincing me that I could do this." Bailey's voice dropped to a much lower volume. "Yes, he's just standing there, waiting for his next instruction I presume," she mused. "I know, I know!" she said, as her voice revealed her excitement. "We'll talk later."

Bailey had now shared her first image of their newly acquired possession with her girlfriend. Just a short conversation with her friend and mentor and her confidence level seemed to skyrocket!

She must be the alpha, he thought to himself about the other party that had been on the phone. His thoughts were interrupted by his new owner. "My friend is pleased with her possession. She wants another picture right after we finish playing dress up. Well, I want to play while we get you dressed up of course!"

He felt his legs buckle. This was his ultimate fantasy. She headed towards the bedroom. "Follow me slut," she demanded.

"Yes mistress Bailey." he replied.

As they entered the bedroom, he noticed that it looked more like a dungeon than a bedroom. There were brass rings at each corner of the bed. A bench adorned with multiple pairs of metal and leather cuffs sat at the opposite end of the room. A huge chest sat at the end of the bed. It's cover was rounded like an old treasure chest.

"You will be spending a lot of time here. I hope you like it. Not that it matters," she laughed. "Tricia and I plan to spend a lot of time here. It matches her bedroom almost exactly."

His other owner, he surmised. "Mistress Tricia," he said to himself.

"Let's take off these things," she said as she lifted the camisole up over his head. She tossed it into her laundry basket next to the bathroom door. "And these," she continued, as she slipped her index fingers into both sides of his panties. It seemed so strange that she undressed him instead of telling him to do it. As she pulled down on either side, he lifted each leg to accommodate her. To his amazement, she lifted the panties to her face and took a deep breath. "Mmmmmm, I like the scent of your pre-cum, my bitch." His cock had gone limp, but that caused it to twitch. She tossed them into the basket as well and motioned him towards the bathroom. "Time to get cleaned up," she said as she casually began to remove her own clothes.

As she unbuttoned her shirt, his first view (from behind) was of her turquoise bra straps. Her jeans quickly began to follow, revealing a very sexy pair of matching panties. Her beautifully-proportioned ass was mesmerizing. Each rounded cheek more than filled her bikini style undies. The lace trim around the waist and legs created a delicate accent. His soft dick began to stir at this delicious sight.

The bathroom was of considerable size, with a large shower on one side and a hot tub on the other. As he entered, she turned towards him and teasingly reached to drop each side of her bra straps in a very seductive manner. It was as if she were putting on a show. As her bra began to fall to the floor, he reached out and caught it. While his eyes were glued to the most beautiful tits he had ever seen, his fingers reveled in the soft, nylon material of his mistress' beautiful brassiere. He didn't dare reach up to fondle her beautiful tits, although it took everything he had not to.

Without any hesitation, Bailey dropped her panties from her waist in one quick motion. She bent over, picked them up and handed them to him. As soon as she offered them, he brought them to his waiting nose, inhaling the sweet scent of her wonderful gift. The gusset was moist and he rubbed his thumb across the material as he enjoyed the sweetness of the smell. She watched, as he wasted no time in bringing the wet material to his waiting tongue. He nearly came from the incredibly taste and aroma of the honey patch that he had thought about since their first meeting. His eyes had closed as his cock sprang to full attention from his sensory overload.

"Those are yours," she said with a huge grin.

"Oh, fuck. Really? Thank you mistress. Thank you," he stammered. He looked at his new prize; size 7, just as I thought, he chuckled to himself. He couldn't help himself from checking the bra size as well. 34C. Mmmm, nice!!

"You can clean those later," she mused, as she took them from his hand and hung them on a nearby towel hook. She reached into the shower and turned on the water. As the steam began to flow out into the room, she stepped into the enclosure. She reached out and gently took him by his now semi-erect appendage. Her soft hand reached underneath his full sack so that she had hold of his entire package. As she drew him into the shower, she turned him around so he was seated at the opposite end of the streaming showerhead.

His heart was pounding with excitement! She reached for a bottle and tipped it up, suggesting he should hold out his hand. As he extended his hand, she poured copious amounts of yummy-smelling cream into it. Taking his hand in hers, she turned his hand over, just above his ever-enlarging cock. She rubbed the creamy lotion across his tight belly and then down into his groin. Her hand moved his, down under his balls, encompassing them with a gentle squeeze. In a circular motion she covered his eagerly hanging fruit and moved up to his waiting and rigid pole. As she moved her hand over his, she said with a sense of anticipation, "stroke it for me, my sexy slut!"

He knew his motions needed to be slow and deliberate or this would end too quickly. She removed her hand from his and leaned back to observe her new toy. The lotion was warm and thick and he loved how it felt gliding over his now throbbing rod. She leaned out of the shower, picking up her phone long enough to snap a few pictures. She returned it practically before he knew it had happened. As she stepped back in, she reached up and retrieved a razor. She removed his hand from it's familiar territory with great control. She then moved both of his hands to either side of the shower seat. He gripped the front edge of the slippery surface. With that, she applied her own hands to his knees, spreading them as wide as they would go.

Without saying a word, she began to slowly and methodically slide the lady razor into the crease of his legs. From here she moved carefully under his balls, lifting and moving them around as she removed every bit of hair. To the top, up over his cock and even along the base of his shaft, she maneuvered her weapon to accomplish her end goal. He stayed completely still throughout the entire procedure, mesmerized by the beauty that was right before him. Her firm tits hung down and moved from side to side with her every motion. Her nipples were rigid and he knew her level of excitement was rising with each stroke of the razor, with each act of control. Neither one spoke a word. The only noise was the sound of the running shower and an occasional moan of pleasure that he made as she navigated his nether region.

To complete the job, she turned him around with his hands on the bench, his back end in the air. She spread his cheeks, adding more lotion to allow for the removal of his man hair from around his puckered hole. "There," she said, "now the girly clothes I dress you in will match your smooth and sexy body! And you are going to LOVE how nylon materials feel against your silky, smooth skin my little slut."

"Oh, and one more thing, I need to mark you as mine," she said in a matter-of-fact tone. With this, she moved him to his knees, facing the shower seat. Using his shoulders for balance, she climbed up onto the bench. Looking down at him, she felt a true sense of dominance. She spread her legs slightly and moved her body closer to his. He was transfixed by the close up view of her beautiful slit.

He had never seen a more perfect-looking pussy! Her clit was only partially exposed, but rigid none-the-less. And her labia looked like petals from a flower about to blossom. Bailey extended her right index and middle fingers towards her mound. She placed them strategically on either side of her clitoris and spread her beautiful lips. "Have you ever had a golden shower my whore?" she inquired of her waiting sub.

"No, mistress Bailey, but I have always wanted to," he answered with enthusiasm.

"I want you to taste me. I have been drinking pineapple juice for your drinking pleasure. You will be pleasantly surprised," she added. And without further notice, Bailey positioned her already dripping pussy within inches of his waiting mouth. In eager anticipation, he opened his mouth. Her new receptacle was about to be used for the first time. As the flow of honey juice began to flow, he felt the heat of it, as it splashed on his face. He quickly moved to capture her gift into his wide open mouth. The intensity quickly increased until a torrent of nearly clear liquid filled it. As he began to swallow, he felt a rush of excitement coursing through his body. He had always wanted this and now that it was happening, he didn't want to disappoint his gorgeous mistress. Mouthful after mouthful, he guzzled his new elixir until the flow began to lessen. He repositioned himself every time her squirt was redirected.

When the flow was completed, he looked up to see Bailey's eyes buttoned tight and a smile on her face that he not yet seen. As she opened them up she softly whispered, "good girl." He had always wanted to be addressed this way and knew he was going to thoroughly enjoy his services to her.

As she climbed down, she motioned for him to move into the running water, which by now had dropped slightly in temperature. As she brought her lips to his, she stuck her tongue out slightly and licked them. "Mmmmm, I told you it was yummy," she murmured. They proceeded to soap up and clean off, both exploring and enjoying each others bodies.

He hoped soon playtime would continue in the bedroom.

Better yet, in the dungeon!

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
spr1987spr1987over 2 years ago

Great story. I can tell that you enjoy your work.

UAlbanyGirl518UAlbanyGirl518almost 3 years ago

You’re killing me! Your deliberate and methodical pace is heightening the eroticism of this series.

The dialogue in this chapter was written much better and really helped the story flow.

And speaking of flow, I was pleasantly surprised by the GS scene, although I wish it was longer and more fully described.

Can’t wait to dive into chapter 3!

AnonymousAnonymousalmost 4 years ago
A dream come true

Excellent writing! I hope to read more very soon. I really like how the relationship is growing slowly and together. I hope you'll draw this out into a long series. Maybe Netflix will pick it up!!! You're on the right track. Feminization can be fun!

AnonymousAnonymousalmost 4 years ago

Way to much of a tease! More please! Golden shower was a good Surprise

Share this Story

Similar Stories

Want to be feminized He always wanted to be feminized and now was his chance.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
Locked Out of Apartment The sexy neighbor girls have a surprise.in Transgender & Crossdressers
Expectations be Damned A shy young man is in for a night of seductive surprises.in Transgender & Crossdressers
The Theater My first taste.in Transgender & Crossdressers
More Stories