Catwoman Next Door Ch. 03

"Yes, Mist..." I started and was cut-off by the crack of her gloved hand on my ass. "Oh! One, thank you Mistress."

She swung hitting the other cheek right away, and I counted, "Two! Thank you, Mistress."

She gave me just a moment to collect myself before she swung what felt like full force on my ass. The sting was far beyond anything we'd done before. "Ohh! Three, thank you, Mistress."

She gave me a moment to catch my breath and then hit the other cheek with another full swat, "Ow! Four, thank you, Mistress."

She took a moment and rubbed her cool gloves over my cheeks, the soft tender sensation mixing with the heat flaring in my ass-cheeks. I squirmed with the mix of pleasure and pain, my head swimming with the overload.

I felt her pull her hand back and I tensed. For a moment she just held, "Relax, sissy girl."

I exhaled and let the tension out and then she struck again," Five! Thank you, Mistress."

She pulled back again, giving me a moment before blistering my cheek, "Six! Thank you, Mistress."

She continued like that until we hit ten and she stood up, running both her hands over my ass cheeks, rubbing the hot spots where she'd hit me several times. I writhed about as the pleasure and pain mixed to make me get excited even more.

She also teased my cockhead through the panties. She rubbed it until I was throbbing and thrashing about, "Oh my, your little clitty looks so trapped. Let's take these off. You're making a giant wet spot."

She slipped my panties down and my cock, well I guess clitty, sprang to life. She rubbed my throbbing member and my balls while running her hands over my cheeks. She ran her fingers down my ass crack and even teased my asshole with her gloves.

She stepped away, did something and came back a moment later with her fingers cold and covered in something, "Ready for your next surprise?" She asked this while teasing her fingers over my cock and balls.

"Yes, Mistress," I hissed with excitement.

"Oh, is my sissy girl, worked up?"

"Yes, Mistress."

"Is it from my hand here?" she ran her fingers over my clit. "Or my hand here?" She then teased her fingers around my hole, slightly pushing one of the lubed fingers into me.

"Oh my, both Mistress," I moaned with excitement and lust.

"So, you want me to finger your cute little ass?" she asked teasingly.

"Yes, Mistress. Please finger me?" I pleaded.

She teased her finger around, slowly sliding it further into me until she opened me up and had her whole finger in me.

"Ohhhh, good girl," she purred and began to finger me, moving slowly and using lots of lube. I panted with lust trying to get more sensation on my cock, but she was only lightly playing with that. Eventually, I tried humping her hand, but that earned me a light smack on my cock.

"Uh-uh, sissy girl, you get off when I say you get off," she reminded me as she began to finger me faster. I eventually got into it and was even pushing back on her finger, trying to get more stimulation.

"Oh, does my sissy like having her ass filled," she teased me.

"Yes, Mistress. It feels really good," I moaned as I voiced my desire.

"Good, then here comes your next present," she then pulled her finger out and I moaned with the sudden emptiness. "Do you know what this is?"

A moment later, she held something up by my face. It was a small latex phallus that I thought was a dildo at first, but it was oddly flared in the middle with a base on the end.

"Is it a butt plug, Mistress?"

"Very good sissy girl, any guess where its going?"

"In me?"

Stacey just purred and she did something. A moment later the cold, wet tip of the lubed up plug was at my asshole. The first few inches pushed in easily and I moaned as it went in. Stacey worked it back and forth slowly, pushing a little more each time until she added a bit more lube and gave one big push. The feeling of the plug going in and my ass closing around it was almost overwhelming.

I moaned and bucked with the overload as Stacey played with my rock hard cock, telling me, "Good girl! You took that so well. That is so hot."

Stacey stood and I looked over where she was cleaning the lube off her gloves, "Stand up, sissy."

I stood, the odd sensation of the plug filling me made something as simple as standing magnified with the plug.

"How is that?" Stacey asked walking over to be face-to-face with me, me looking up slight up at her. Her higher heels still giving her sleight height over me.

"Its great," I replied. "It does feel a little weird to have it filling me when I stand."

"Can you walk? Take a few turns for me," Mistress Venus told me.

"Yes, Mistress," I said and took a few small steps to start. Once I got used to the feeling, I was able to move with little difficulty.

"No problems walking then? I mean other than the small tent pole in the front," she said with a gleam in her eye and a sly smile.

I blushed, "No, Mistress. It took me a few moments to adjust, but I'm good now."

"Good, then go get me a water. I want to show you the next surprise. Well, actually this one is for me, but I'll be using it on you."

That seemed ominous, but I made my way out into the kitchen and got a water for her. I came back into the bedroom and Mistress Venus was standing poised on her heels, holding a small paddle in one hand. Where did that come from? Why was I asking? I knew the answer.

I handed her the water and she ordered, "Get back in position over the end of the bed. I want to try this out." She showed me the paddle up close and I swallowed nervously. It look like a wicked little thing that was going to hurt.

I got back in place. She took a few drinks of the water, then hiked my skirt back up, "That is so hot. You are definitely going to be plugged a lot more often."

She then took a few test swings with the paddle, "You don't have to count these, honey. These are for me to enjoy."

She then swung the paddle and the smack of it connecting with my ass sounded like a shot. The sting was even more intense than her hand had been. She swatted me a few times, trying different angles and ways of standing. The weird part was flexing slightly made the plug get pulled in, then as I'd relax it would slip back to the flared part. So, I was basically fucking myself with the butt plug.

Finally, she settled on a position she liked and said, "Okay, these are for real."

What the hell did she mean by that? So far they'd been pretty intense. No time to consider as she swung what must have been full-force or close to it. I actually lifted up a little from the bed and gasped with the shock of the hit. This wasn't a moment before the pain flared, this was full intensity right away.

She then rubbed the cool leather paddle against my ass again making my brain foggy with the mix of pleasure and pain. The next swat came as my fog was starting to clear and she did just two more like that before she dropped the paddle on the bed, running her hands over my ass again, teasing the plug and playing with the red marks on my ass.

She then growled, "Get on your back."

I climbed up and she pounced on me, kissing me intensely and she pushed me hard onto the bed. She reached down and unzipped the crotch of her suit. She turned and pinned my arms with her boots before planting her soaking wet pussy directly on my face.

She ordered, "Lick me, slut!" She then began roughly stroking my cock with her gloved hand as she ground on my face.

She must have been as worked up as I was, since she ground on my face for just a few minutes before thrashing in one of the most intense orgasms I'd ever seen her have. She had stopped stroking me while she came, but then started stroking again as she came down, sliding a bit further up, putting her ass on my face.

"Good girl," she growled. "Now lick my asshole while you cum."

I dutifully tongued her ass, not that I had much choice in this position. She began really working my cock, stroking steady and even, using long fluid strokes. She must have grabbed the lube since I felt her hand slipping and sliding all over me.

I moaned into her ass as I built up. I was so worked up, I wasn't going to last long. As soon as she reached down and began playing with plug I grunted, tensed and exploded. My own orgasm felt like it went forever. As I came down, I began to feel the same way I always did after dressing and cumming. The guilt and remorse, mixed with the thoughts that no real man would do something like this made me want to get undressed right away.

Stacey turned with my seed dripping off her gloves, "Time to clean up, sissy girl."

She then had me lick her glove clean. Once it was clean she snuggled in next to me, but I was trying to get up.

"Where are you going?" she asked.

"To get undressed," I stated.

"Why?" she seemed confused. "I want you to stay femmed up for a bit longer."

"Really? I...I...," I wasn't sure how to say it. "After I cum, I usually get undressed."

"Well, you don't have to, you can stay, if you like. I like this side of you," she said smiling tenderly.

So, I laid with her and we chatted about the scene and how we felt. She asked about the plug, which oddly enough, was so comfortable now I had almost forgotten it. I never dreamed I'd be able to forget about having something shoved up my ass!

"How about wanting to get undressed right away? What was that about?" she asked.

I tried to explain, "After I cum, I just start to feel all the guilt and everything build up. All my anxiety about being feminine and being rejected. I don't know, it just seems to hit really hard after I cum."

"Well, you know, this is a safe space, right? I'm not going to judge you? Hell, I'm going to find every excuse I can to get you in this maid dress," Stacey said.

"I know, but this is a long standing guilt that didn't start overnight, so its not going to go away right away. I think it will just take me some time to get used to being my femme self," I said.

"Well, was there anything you really liked?" she asked.

"I really liked being dressed, of course, and licking your boots was pretty intense and fun," I said.

"Good, the spanking was okay?"

"Yes," I said. "But my ass is going to be sore tomorrow"

"Good, you were asking for it," she stuck her tongue out at me. "And the anal play?"

"That was intense, but it felt really good," I replied. "Again a bit of guilt there."

"Okay, noted," Stacey said. "Anything else you'd like to do?"

"Well," I said unsure how to say that I thought she was going to climb on and have sex with me.

She saw my hesitation, "Its okay, no judgment. I have stuff I want to try, but I don't want to push too far too fast. The plug seemed like a good step."

"It was, I really liked that part. I just though when you were undoing your catsuit, we were going to..." I trailed off.

"You thought I was going to fuck you?" she filled in the blanks. "Like traditional vanilla sex?"

"Well, kind of, yeah," I shrugged.

"So, you want my virginity?" she teased me.

"Wait? Your virginity?" I said confused. "I thought you and Harry... y'know."

She laughed, "I think I said Harry and I fooled around."

"Well, yeah, but you guys were together for a while, so I figured that meant... everything," I said. "Sorry, I didn't realize you hadn't done that yet."

"Its okay, we never really talked about it, so that's on me," she said. "I do like the idea of you being my first time, but I want it to be something special."

"What did you have in mind?" I asked curious and a little hesitant.

"Well, I like the idea of me taking your virginity first," she smiled at me like a predator to its prey.

I was confused, "But I'm not a virgin. You know, Julia and I..."

"Yeah, I know, but that's not what I meant, I mean back here," she ran her hand around to tease the butt plug. "I want to fuck you in the ass."

Whoa! That was pretty intense. And pretty hot now that I thought about it. "Well, how? I mean, you're not... equipped for that?"

Stacey got up and went to the dresser and picked up a dildo and a harness, "I can be."

It took me a moment to realize it was a strap-on. Oh wow! "Is that another surprise?"

Stacey nodded with a big grin on her face, "So, what do you say? Can I fuck you?"

"I don't know if I'm ready for that right now," I said.

"Not now, I was thinking after graduation and the parties, this could be how we celebrate," she said.

I nodded, "I like how you think. That sounds amazing!"

She put down the harness and came back over to me. She climbed on top of me, "I do have some requirements if you're taking my virginity."

I swallowed nervous where this was going, "Of course, Ma'am. As you wish."

"First, you're tied to the bed, so I'm in complete control. Second, you lick me clean," she looked down.

"Sounds great so far," I replied.

"And last, after we're done, I get to lock you in chastity," she bit her lip.

"Chastity? Like Victorian England chastity belts?" I replied.

"Not quite," she said. She held up a small phallic shaped piece of plastic with a small lock on it. I realized it was a plastic cage to go around my cock and balls.

"Whoa, that's... for me?"

She nodded enthusiastically, clearly excited by the idea.

"Let me guess, Kate has Steve locked in chastity and this is one of their old cages?"

"Uh-huh, you're getting the hang of this," she nodded smiling away. "What do you think?"

"Well, I'm a little nervous about it, but we can talk about that, but if it means us having sex, then yeah, I guess I'm all for it," I said.

We then both got undressed and cleaned up. Taking the plug out was an exercise. It also made me realize I was going to need to start cleaning my ass out, especially if she was going to fuck me in the ass. We laid back in bed to cuddle together. I must have dozed off at some point and was awakened by Stacey talking softly.

"No, he's asleep right now," she said. "Yeah, it was pretty intense, but you were right, he loved the butt plug. It looked so sexy in him." She paused, "Yeah, we're going to get together again this week after graduation. Yup, he sure did, I even showed him the cage. He's a bit hesitant."

I got up and tried to quietly get a drink of water.

Stacey saw me and said quietly to me, "Its Kate." Back into the phone she said, "I don't know let me check. We're still good to go to the munch next week?" She asked me.

I shrugged, "I don't know, will Kate and Steve be there?" She nodded, so I replied, "Sure, let's do it."

"He's down with that. Yeah, I think him getting to meet Steve will be good," she said. "Let me ask."

She held the phone down, "Do you want to talk to Kate? She'd like to ask you some questions."

I shrugged, "Yeah, I guess so."

Stacey handed me the phone and I heard Kate's voice "Hey there, how are you? How was the scene?"

"It was amazing," I said quickly. "I had a lot of fun."

"It sounds like she wore you out," Kate said. "Are you excited for your post-graduation celebration?"

"I am, but I'm also a little nervous," I said.

Kate replied, "That's understandable. What are you nervous about?"

"Well, everything, I guess," I said. "I mean, I'm worried how the strap-on will feel, I'm worried about being in chastity. I mean I'm even a little worried at how well I'll... perform. I want her first time to be great, or at least memorable."

"Well, that's good that you're thinking of her," Kate said sweetly. "For the strap-on, just make sure you take your time and use lots of lube. Also, practicing with the plug before hand will help... stretch you out. As for the chastity, its a lot of fun, but it does take some adjusting, but you'll get it."

We chatted for a few minutes about various things, and it was interesting that even though we talked about BDSM and sex stuff, it wasn't really sexy. That was one of my first lessons that BDSM is about a lot more than just sex. The mental aspect is an important part. In some cases, it might be the most important part.

After the call, Stacey and I cuddled on the bed and she asked, "How are you feeling?"

"Good, my ass is a little sore, but nothing bad," I replied.

"That's good," she smiled. "How about your guilt? I know you said, you would feel guilty about dressing?"

I shrugged, "Yeah, its there. I just get this feeling like no 'normal' guy would want to dress like this."

She rubbed my side comfortingly, "Does it help being with me and that I like it?"

I nodded and hugged her, "It does, thank you for embracing it. I've always felt really weird about it, so its nice to have it feel, well maybe not normal, but more normal? Accepted? Something like that."

She changed the topic, "Is your mom having a graduation party for you?"

"Yeah, but its mostly a family thing, you're certainly welcome to come. I've told mom we've been seeing each other, but since she already knows you, its not like she needs to 'meet' you," I stated.

"So, she doesn't need to meet your girlfriend?" she smiled at me.

I shrugged, "I didn't really want to label it, especially since we're being kind of..."

"Non-traditional?" she finished for me.

"Yeah, that's a good way to put it," I nodded in agreement.

"My mom is having a small party, too. Mostly family as well. How about you come over here and we'll do this party first. Then we can go to your house and come back here afterwards to really celebrate?"

I thought for a moment, "What about Ted and Brianna's party? They're going to be the big celebration of the evening. We should probably put in an appearance."

She frowned, but then grinned. "Okay, but I think we should both have some surprises under our clothes."

I had a feeling that this was going to be fun, intense and scary at the same time.

I kissed her and said, "Yes, Ma'am. As you wish."

"Good," she smiled. "This will be fun for both of us."

It was a busy week with rehearsals and wrapping up everything with school, thankfully most of it was fairly relaxed, so Stacey and I were able to spend a bit of time together. Though she did have the additional responsibility of writing a speech for graduation. She wasn't our valedictorian, she was instead the salutatorian. Yeah, I didn't even know that was a thing. Which was weird, considering I was in the band and played several of the graduation ceremonies over the years. I guess I just never paid attention to the whole deal. Dog and pony shows were never really my thing.

Oddly, the old mousy Stacey would have been petrified of giving a big speech, but this new dominant Stacey was actually excited about the prospect. There was an odd situation where our first graduation practice was delayed about a half hour. Apparently there was some kind of confusion over who was actually the valedictorian. Remember this was the 90s, so the programs keeping that information were pretty basic. The school wound up having the AP Math teacher go through and calculate the GPAs to the fifth decimal place to confirm it.

One of the other geniuses in our class was finally confirmed as the valedictorian, Stacey as the salutatorian and we were underway.

Graduation day arrived pretty quickly and lots of scurrying around, getting ready, making sure everyone was dressed appropriately. Eventually we were all on the field in our procession. The whole ceremony and tradition and everything was pretty lost on me. My main thing was to get my diploma and to support Stacey.

The speeches were thankfully pretty quick since it was a sunny June day and I was wearing a friggin' shirt, slacks and tie under my robes. I don't know why we were dressed formally. We were wearing robes, no one could tell if we wearing shorts. Then again with my legs shaved, I was kind of glad I wasn't wearing shorts.

Anyway, I was kind of zoning out, barely paying attention when Stacey was introduced and I made sure everyone around my seat gave a rousing cheer and applause. I was possibly overly enthusiastic, but I didn't really care.