Locktober Eternal - Ch. 02

Chapter 2

"Hey! Watch what you're doing down there!" I paused as I added, "Do you know what you're doing down there?"

I breathed out slowly as I stood up straight. My core was tight and sore after my workout this morning. My no means was I out of shape, but I had forgotten how an intense exercise could knock you on your ass.

We had gotten up together at sunrise and gone for a run. Three miles later, Hannah and I did some yoga and core exercises. Fresh out of the shower, I was still glistening with heat, and I waited as Hannah worked on the new present that had arrived earlier.

"Relax," Hannah said as she sat on the floor against the bed. I stood over her with my pants and underwear on the floor next to us. My junk was practically shoved into her face. Unfortunately, nothing exciting was happening.

She continued, "It's just like a jock strap... sorta."

As I chuckled at the sarcasm, a cold silicone wrap began to encase my genitals.

"As I was saying," Hannah said, "I was researching stuff for crossdressers and drag queens. How do they keep their meat tied down for so long? Now, as someone without a dick, I gotta say: all of this was equally fascinating and mildly sexy! I had never thought about how you guys just have stuff swinging around down there! So, I found this reddit page that led me to this TikTok lady. She's some full-time dominatrix for-hire, so I called her up and she'll be here later today!"

My mouth dropped open as I gasped!

"Kidding!" Hannah laughed, "She was talking about this gaff device that is more or less a silicone padding that grabs your dick, shoves your testicles back up into you, and then smooths down the front so there is no room to wiggle out or anything. But! Because it's made to look like a pussy, it's got some magic in it. Basically, your dick gets pushed down so that your piss comes out straight to the bottom, just like a woman! It's even got five stars for hygiene, so you won't have to take this off to use the bathroom!"

Her hands began to canoodle my balls and suddenly, I felt them push up into me.

I stiffened up, and Hannah laughed again.

"Sorry if it's uncomfortable now. You need to get used to wearing this now, so you can be more comfortable at the party."

"First place wins a Maladucci's gift card, but is this worth it?"

Hannah shrugged. "I think it's pretty hot, so you're definitely going to get laid more often. Is that worth a slice of cake?"

My dick pulsed, but I couldn't really get hard. The silicone was loose enough to not pinch and pull on my skin, but it also was firm enough to keep my cock pressed down and prevent the blood-flow for an erection.

The bottom of the padding was shaped and molded to look like a vagina, and there was a hole to let my pee come out. The head of my dick was waiting just behind the fake lips of my own vagina.

"Also," Hannah added, "There's a few more things with this. You'll wear this off and on. Don't worry, you aren't locked in here for life."

Sarcastically, I wiped fake sweat beads off of my forehead.

"Instead, you'll be locked in this when you get out."

Hannah revealed a second small box, and I knew what it was.

In the bedroom, we were both open about what kinks were expected from both of us, and Hannah was not quiet about her love for chastity. We had tried it before, but life happened, and we fell out of it. Now, she was reintroducing it for the first time in almost a year.

When I get hard, my dick grows to a very modest six inches. A year ago, I had worn the cage for so long that I lost about two inches to my cock. When we stopped, it took some time, but I could grow it back to full length again. However, I had made it very obvious that something about my smaller dick had really excited me. I was very happy to get back to the cages with Hannah.

Hannah instructed, "We're going to the mall in a little bit, but I won't make you wear the silicone pussy out yet. We need a better name for it by the way! When we leave, take off your pussy, and put on this cage." She tossed me the box. I heard the plastic bits run into each other inside.

Despite my excitement for this, I wasn't thrilled about crossdressing in front of our friends. "Hannah, why are you going to this much trouble for me to wear a dress. I guarantee no other guy will do anything this drastic to simply wear a little dress! It really isn't that much work to slip into a dress."

"You're totally right! No other guy would. But you aren't a guy, are you? You're my little bitch." Her hand went between my legs, and she started to massage me as if I actually had a pussy. "And who said anything about only a dress?"

Hannah groped me for a moment, then she playfully slapped my pussy-dick.

"Get ready, babe! I'll heat up some food for lunch. Lock yourself up and leave the key on my nightstand. Be ready to leave in fifteen!"

Hannah left the bedroom, and I turned to look at myself in the mirror.

In a horror movie manner, I was smooth like a Ken-doll downstairs, but it unmistakably looked like I had a pussy. I'm not sure how Hannah had requested the perfect skin tone, but the color of the wrap was exactly the hue of my skin.

I touched the lips with my fingers, and I could feel the same valleys and hills of Hannah's pussy. I could feel a small bump where the clit was supposed to be...

Reality came back to me.

It took a minute, but I got out of the silicone-pussy. Hannah was right. This thing needed a new name.

I put the pussy away, and I opened the chastity box.

My heart raced as I took it out of the box. Something about this cage caught my eye.

Normally, the space for the lock sits above the cage, so there's always a bump. Further, my balls usually dangled down as I wore a cage.

Instead, this cage locked below my balls. Further, I couldn't get my balls to sit outside of me while I wore it. The only way I could lock the cage was with my balls tucked up inside of me. I had to pull the extra scrotum skin around the edges of the cage to lock myself in firmly, and as a result, it looked exactly like a pussy.

I laughed as I realized what this cage was.

I had never seen a cage do this before, but somehow, I had completely replaced my penis with a vagina.

Hannah was crafty. It was one of the reasons that I loved her and had asked her to marry me. She was great at picturing what she wanted, and then ceaselessly working to find it. I wondered how long she had searched online for both of these gifts. Days? Weeks? Either way, she clearly wanted me like this. She loved to see me like this.

"And who said anything about only a dress?"

I could only wonder what we were getting at the mall.

Hannah sat across from me in the food court at the mall. She chewed on soft cinnamon pretzels and slurped on a red slushie from Auntie Anne's. Around her neck, a small metal glint flickered in my eye. The key to my cage dangled around her neck.

"Want any more of my drink," she offered?

I waved it away. I wasn't very hungry today. In fact, I was rather uncomfortable.

I shifted in my seat, and Hannah laughed, immediately noticing that I was fidgeting.

"What's wrong babe?" Her smile teased out a silent Ha ha ha!

I forced a smile and lied through my teeth. "I'm doing just fine."

"Good." Hannah chewed on her straw for a moment. "How about... faklit? Like, fake-clit?"

"You can do better. What about sili-coochie?"

"Not bad! We can get there!" Hannah's phone beeped. "Grab your stuff! Time for your appointment!"

"Appointment?"

She winked at me as Hannah stood up to leave. "It's time to go get fitted for a bra."

I trotted alongside her after throwing away our stuff. "Come on! Fitted? We could just guess the size."

"True," Hannah said as we walked through the mall. "Or, we could have some more fun! It doesn't cost anything at Victoria's Secret! Don't be a baby about it."

"Fine, but do you realize you need to start bulking up to get your muscles to look like Travis Kelce?"

Hannah flexed her bicep then kissed it. "Bulk up? I'm already bigger than he is!"

I rolled my eyes, and she held my hand.

"Here's our checklist at the moment: get fitted for a bra; buy spanks, underwear, and a corset; stop by Sephora to get your skin tone; go in and request a wig (optional); thrift shop for the clothes; resort to Amazon for anything else."

"Oh, is that all?"

"I didn't want to make it too much!"

"What about the wigs? You said it was optional."

Hannah ran a hand through my hair. "I was going to leave this to you. Your hair is already mildly long. Right now, we could style it into a cute bob if we wanted to. If you let it grow for two more months... especially with how fast your hair grows. Honestly, I think either option is a good choice. I'll leave that one to you."

I looked at storefront windows as we walked, and I tried to catch glimpses of myself. When you look at everything as "masculine" or "feminine," you forget how easily things can cross the border. My hair was brown and long enough to touch my shoulders. Hannah was right. My hair would grow another two inches in two months.

"Taylor is blonde, so are we going to dye it?"

"Halloween hair dye is super easy to wash out. I think that's the better option anyway. Wigs always feel weird."

"You're going to wear one this year! Are you excited?"

Hannah shrugged it off, "I won't wear a wig! I'll just shave it off."

We both laughed! Hannah had never had her hair shorter than her shoulders for her entire life. It would have to have been the end of the world for her to actually cut her hair.

We rounded a corner, and I could see Victoria's Secret ahead.

Hannah asked, "What sounds good for dinner?"

"Is Maladucci's an option?"

"Not after what we'll end up buying over the next few days."

"I'll be honest," Amber said, "I don't usually measure men."

"Usually?" Hannah asked, "How often does it happen?"

"Well, I've been working here for eight years. In eight years, you're the first!" She looked to be about thirty. Amber smiled as she spoke every word, and I wondered if it was out of uncomfortableness, or if she was having a lot of fun today.

We were all gathered in a changing room in the back. Hannah and I stood awkwardly as a team-member, Amber, explained the process.

Hannah said, "I also want to get measured, so maybe it will be easier for Daniel if I go first, then he gets to see how it's done."

Amber smiled. "Works for me!"

Hannah started to remove her clothes. Amber pulled out a measuring tape. The tape ran around her nipples, then under her boobs. I realized I was so grateful I didn't need to get measured to buy a pair of socks as a man.

"You're a 34C, ma'am."

"Wonderful!" Hannah started to redress. Daniel, you're up at bat!"

I took off my jacket and shirt, and Amber measured me in a similar way. I didn't have any breasts, nor were my pecks large at all. I wondered if there was a size smaller than A cup.

"34...A? You don't really have a cup size, but then again, some women have very small breasts as well."

Hannah threw her hair back into a ponytail as she finished redressing. "Thanks, Amber."

"Of course! You said this was for a Halloween costume? Very dedicated! I mean, it's only August 8^th."

"You can never be too prepared!"

"So, who are you going as for Halloween?"

I answered, "Taylor Swift."

Amber smiled, "You'll look great!"

We redressed, and Hannah and I began to shop through the stores.

In Victoria's Secret, we bought three bras - two for Hannah and one for me. Mine was a purple push-up bra. Also, we bought a dozen pairs of panties. A year ago - when we had previously played with chastity - I was commanded to wear panties, so this was nothing new. With my bodysuit / ballgown dress combination, I couldn't just wear boxers. I was going to end the night in something very revealing, so I was going to have to wear a thong. We also shopped for a corset, but didn't end up buying anything. Nothing in the store was as form-fitting as we wanted. Add one to the Amazon list.

Next, we stopped by Sephora and met with a stylist who measured my skin tone. Hannah bought foundation, eyeliner and shadow, Taylor's signature lipstick color, and a few other pieces for my makeup.

For another hour, we jumped in and out of stores looking for anything that could resemble Taylor's Midnight bodysuit or her Folklore flowing dresses. Nothing within a reasonable price tag came close, so we ditched the mall and drove across town to multiple thrift stores.

Tulsa is progressive enough, but in every mom-and-pop shop, the older owners gave us the most judgmental looks. Discounted dresses appeared in every store, but only in the third store did we start to have success.

"It's rustic, mildly nude in color..."

"I'd say it's a little pinkish," I added.

Hannah nodded, "And for twenty-five bucks! Let's go try it on."

Again, she and I ran into the dressing room, and she helped zip me up. I fit perfectly into the dress, and Hannah began to notice a few problems.

"First, your body hair is going to need to vanish. You're like a wooly mammoth!"

"I can't help it!" I pulled her into a kiss, and her hands brushed over my chest.

"Second," Hannah said as she pulled away and rested her head on my shoulder, "Your boobs aren't growing..." She asked sarcastically, "Are you taking your estrogen injections every morning like we discussed?"

I pressed a hand to my heart, "I swear to God himself that I am."

"We'll fix that. The dress looks weird without boobs for you. Honestly, it fits you really well everywhere else, but the bust looks wacky."

"What are you thinking?" I was invested at this point. I could see it in her eyes, but Hannah was thinking through ten million options. When she went silent like this, I knew I had to just leave her alone for a moment.

In the mirror, I couldn't help but love the way I looked. Sexuality was something Hannah and I were comfortable with, but gender had never really played a part in our relationship. Hannah loved to feminize me every once in a blue moon, and I had never minded it, but there was absolutely something there for me. I had never tried to express it, but there was some correlation between feminization and my own happiness.

Hannah and I had been together for a few years, and we had only discussed this once.

One year ago, Hannah and I had driven out to San Antonio for an anniversary date. I purchased a few nights in a lavish hotel and reserved a romantic night at a restaurant downtown, and Hannah had planned out our itinerary and the excursions.

Two bottles of white wine later, we started to really ask deeper questions. Red wine made us romantic. White wine made us horny.

I started asking her questions as we sat alone at our table in a corner of the darkened restaurant.

"What's with you and chastity?" I looked at Hannah and a smile drunkenly crawled across her face.

"Be specific." Hannah sipped on her wine.

"Okay," I said, "what's your first memory of it?"

Like a decanter, Hannah let her words breathe. "I was a teenager, and I was reading fanfiction on my laptop. I don't remember the exact story, but it was about some hot lady and how she walked around with a key as her necklace." Her fingers went up and touched the key that hung around her now. "I only remember one sentence, loosely: ...every time I felt it tap my chest, my heart skipped a beat. If someone looked at my necklace, maybe they didn't know what the key was for. Maybe they thought it was for my diary. In a way, it was. I kept my favorite secrets under lock and key..."

She sipped more of her wine and then said slowly, "Ask me more questions like that one."

"You're with me, but are you fully straight?"

Hannah scrunched up her nose. "That's such a boring question. Obviously, I'm not fully straight. You've heard me talk about other women in bed. No straight woman dreams of her coworkers eating her out under the desk at work. Daniel, I'm just attracted to being attracted."

"Then, with this cage. We don't get to have sex."

"Wrong. You don't get to have sex with me. I can bend you over like I did before dinner. Isn't that sex?"

I smiled. "I didn't cum, so I wouldn't call that sex."

Hannah smiled back then bit her lip. "You moaned like a bitch that came. All the same to me. But don't worry. I'll make sure you come tonight. We won't stop until I have something to lick up tonight."

I gulped, then finished my glass of wine. I grabbed the bottle on the table and topped off our glasses.

"Next question," Hannah ordered.

"It's not a question, but explain the panties. Why do you want me to wear them?"

"Boxers aren't always sexy to me. Is this any different than if I said 'Daniel, you look great in red!' then the next day, I go out and buy you a red tie? Why is it any different if I say that your ass looks fantastic in lacey black thongs and maroon panties with little bows on the front?"

My dick pressed into the cage I was wearing, and I couldn't take my eyes off the key around her necklace.

"My turn to ask a question," Hannah said! "In the past, I've tried to do this stuff with other guys, but they never allow it. You're a man, but what kind of man wants to wear women's clothes and get fucked like a woman?"

I didn't have an answer.

Hannah nodded. "I like the silence. I can tell you're really thinking about that one. And you don't have to be manly for me to find you attractive."

"What if I don't want to be manly," I suggested.

Hannah knew me, and she knew what I was getting at.

I continued, "What if I don't always feel manly? Sometimes, I like to feel pretty, and feminine. Other times, I feel manly and strong. Would you still love me, if I felt that way?"

She knew me better than my parents had ever known me. I didn't need to speak when I was frustrated. Hannah could look at me and know what I needed. However, Hannah always had been more mature than in her years. Even if she knew that I needed to say or do something, she took the steps for me. Hannah would wait for me to find out what I needed for myself.

Suddenly, I was back in the dressing room.

Hannah said, "Sorry, I was really thinking about this one!"

I was back to looking at myself in this dress.

"Overall, I don't actually think this is the one. For starters, the naval drops too low. We wouldn't be able to have your bodysuit underneath without it showing. Second, I think it's almost too see-through anyway. Third, and this is for any dress we look at - your lack of boobs will be an interesting game to try and win. Boob tape will do some good, but a strong pushup bra can only push up so much, but without any breasts..."

Hannah slapped my ass and then kissed my neck. "Whatcha think, babe?"

I laughed and pulled the strap up on my shoulder. "I like it. It seems pretty casual, and maybe it's not ballgown-ish enough anyway. It also seems short enough that like, wouldn't this just be a dress for a Sunday afternoon?"

"I agree. It's a little too dressed up for casual wear, but it is too dressed down for Speak Now on the Eras Tour. Want to go look for some other dresses?"

"As long as I'm not cooking tonight for dinner!"

Hannah kissed my neck again, then my cheek, then my lips. "I'll make you whatever you want, babe! You've looked so cute today; you've earned whatever you want for dinner!" Then Hannah moved down and kissed my chest where my cleavage would be, then she continued to kneel down and kiss down my stomach. Her hands lifted my dress, and they reached around to my butt. I was still wearing boxers, but she pulled them down in combination with her hands and teeth. My cage pushed out like a madman, but the design restricted anything. Again, my scrotum was pulled out in front of my dick, so nothing was visible. The head of my penis was hidden, and it literally looked like a pussy, just bulged out by half-an-inch.