What You Let Slip Pt. 03

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Jen takes Steven to a lingerie shop and humiliation ensues.
6.4k words
4.68
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Part 3 of the 3 part series

Updated 06/10/2023
Created 04/25/2021
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I wanted to thank you all again for the kind comments and support! It's different writing this kind of work than what I'm used to and I'm glad people seem to enjoy it. I'm looking forward to what you all have to say about this part!

Please read the first two parts if you haven't yet or this won't be as clear!

*

Through the whole drive, I couldn't take the focus off my cage. I kept touching it, trying to expand, every bounce of the road noticeable. Jen wasn't helping, sitting in the passenger seat, she had her right leg raised so whenever I glanced over I could see her hose covered thigh. I felt my cage tighten. I made eye contact with her, she knew the effect it was having on me as she smirked.

She guided me to a small strip with only a few stores, most abandoned. There was a lingerie store named Cherie. "This is where I get most of my lingerie. I know you are a big fan of it."

I was hesitant to exit the car. "I-- I have to come in with you?"

"Yes, silly. We need to make sure we get the right size for you." She said, exiting the car.

Now out, I looked at the store front, a few mannequins were in the window wearing all sorts of lace and silk. I gulped but felt my cage pulse.

Inside, I began scanning around and didn't see anyone besides the employee. And then it hit me, it was Hannah. One of Jen's close friends. I had known her just as long as I had known Jen. I almost dated her. Fuck. I looked at Jen quickly, "Hannah works here?!"

"Mmhmm. She gives me her employee discount."

Hannah came out from behind the counter. She was wearing a tight and very revealing crimson dress, her large breasts were pushed up showing a vast amount of cleavage. On her legs, she had very sheer black hosiery, I couldn't tell if they were stockings. Making her way to us quickly, just on the cusp of running, she hugged Jen.

"Jen! You didn't tell me you were coming today? It's always dead on Saturdays, I'm so excited you're here!" She looked over to me, a little confused but still happy to see me, "Hey Steven. It's good to see you also!" She leaned over to give me a light hug. Feeling her breast against me, my cage swelled painfully.

"Hey Hannah. It's good seeing you too, it's been a while!" I felt extremely awkward about this whole thing now.

Jen was all smiles, she was loving my nervousness. "I wanted to stop in and find something to wear tonight and, well Steven wanted to come along."

Hannah smiled, "No worries. I need to do some more inventory, but you two can look around and use the changing room. Just no being naughty." She said with a wink.

We spent the next twenty minutes looking around the story, me pointing things out I liked and then Jen making me hold them. My cage wouldn't stop throbbing the whole time. Heading into the dressing room, it was rather large with two full length mirrors on the walls. We had a pile of lingerie and I couldn't wait to try them on.

"Are you ready? You need to strip down." Jen asked.

I was nervous, Hannah was just in the other room. "What-- what if Hannah comes in?"

"Why would she?" Jen came over to me helping me with my shirt. "She thinks I'm putting a show on for you."

Apprehensively, I unbuttoned my pants, lowering them. I hadn't realized just how much I was leaking. A giant wet spot had formed, coating the entire front of the panties. Jen was absolutely shocked, "Holy shit, you're so wet!"

She pulled the waistband back from me, a trail of thick precum was coming from my cage attached to the panties. Jen took her finger and scooped it up and stroked the tip of my cage, I let out a small moan. Quickly she put her coated finger in my mouth. Repulsed for a second, I knew better than to say anything and sucked it off her finger. Looking past her hand, she had a devious smile on.

"God. That's so hot." She shivered. "But we need you to start trying things on." She handed me a bra and panty set. They were pale salmon and covered in lace. "These panties should fit but try the bra first, we don't know your actual size yet." I began sliding the bra on, excited to see how it looked, the color went very well with my pale skin. Jen came around and helped me attach the back, "No I think this is too small, it'll cut into you after a while. I'll go out and find another one."

As Jen opened the door, I could see Hannah. She looked up at the noise and we made eye contact, she was suspicious and started our way. Jen realized what happened, and spun around fast, closing the door. She looked up at me, we were both frozen. My face was beet red and burning. Jen mouthed, "I'm so sorry."

I jumped when there was a knock on the door. Hannah, tentatively, "Is-- there anything you two need?"

Jen opened the door again, fully exposing me. I moved as much as I could to cover myself. "Jen!"

Hannah stifled a laugh, "If you had told me you were shopping for Steven, I would have asked to help."

Jen looked back at me, a smile came over her face. "Actually, we don't know his real bra size so if you could help us with that we'd really appreciate it."

"Of course!" She pulled out measuring tape from the apron she was wearing. My mind went to the night Jen used a similar tape to measure my length and then brought me to an amazing orgasm. Hannah stepped up to me, "I need you to take off that bra to measure you correctly. And you don't have to cover yourself, we get boys like you in here all the time. Plus," She winked at me, "I'm a professional."

I lowered my arms, a look of defeat came over my face. "I need help undoing it."

"It's not a problem, I'm sure you'll learn how to do it yourself soon enough." Looking down at my panties, she paused, "What's that?" Pointing at my crotch, I realized she was talking about my cage. I wanted to die from the embarrassment.

My mouth opened but nothing came out. Jen stepped in. "It's a chastity cage."

Hannah's head whipped to Jen. "Can I see it?"

I looked directly at Jen, shaking my head no. Jen chuckled, "Sure, you're helping us out. Steven, lower your panties." This caused both of the girls to burst out laughing. I just stood there, feeling my blush cover my whole body. My cock betrayed me as it pulsed in its cage.

Collecting themselves, Jen came over to me. She put her hand on my stomach and looked into my eyes, she towered over me as I was slouching into myself. "Sweetie, it's okay. Hannah is not going to tell anyone."

I looked at Hannah, she just smiled back at me. "Okay." I slowly lowered my panties.

Hannah came back over, crouching down to look at my caged penis. Looking down at her, all I could focus on were her large breasts. "Wow. It's so small."

"Hannah--" I let out.

She covered her mouth, clearly laughing. "I'm sorry, Steven. But it is, it's so cute. And very wet." With emphasis on the very, she reached forward and to play with the trail of precum. She looked up to Jen, "How do you guys have sex?"

"Hannah!" I let out, again.

Jen, still standing next to me, looking down at Hannah, "This was actually his first day wearing it. I didn't want him to have a boner the whole time walking around the store."

Hannah looked up at me, "I think it suits you, Steven. I don't think I would let you out if it were up to me. With a dick this small, you might as well not have one. You basically have a clit."

I couldn't believe any of this was happening. I felt my cage tighten. It pulsed out a huge stream of precum, a moan escaped with it. Hannah's hand was still there, catching it all. She stood, bringing her hand up to show me, a large puddle of precum sat in her palm. I couldn't believe how much I produced, "I think it agrees with me."

Jen pushed me head forward. "Lick it up, sissy" Moaning, I leaned my head forward taking Hannah's hand in mine, I licked her hand clean.

"Fuck. I could get used to that!" Hannah whispered out.

Jen, full of confidence, "Right?"

Hannah, now completely professional, "Alright, turn around Steven. I'll help you out of that bra." Once off, she brought the measuring tape out, she wrapped it around my chest taking a few notes as she did. "I'll bring in the matching bra for that set, here are his measurements Jen, can you grab the rest that you two wanted."

"Sure thing." Jen said, leaving me alone with Hannah.

"I'm so glad you two came in today, it was going to be a very boring day, but I think you awoke something in me and I can't wait to explore it." She put her hand against my cheek. "Thank you for that." Looking down again at my cage. "I love this. You better hope Jen is kinder than I'd be with it. I don't know if I'd ever let you out." With that, Hannah tapped the end of my cage and left the changing room.

Standing there, with my panties down around my thighs, I looked down at my cage. My crotch was bulging out, trying to get hard. A new stand of precum was hanging from the tip. I scooped it up, looking at it, I quickly took it into my mouth. I actually enjoyed the taste of my precum.

Waiting for the girls to return, I still couldn't fathom that this was all happening. Not only Jen allowing this, but Hannah's brazenness. Her talking to me that way excited me to no end. How was I going to make it through this?

Jen came back first, laying the bras and a few other things on the bench of the changing room. Coming over to me, she wrapped her arms around my neck. "I really am sorry that this happened. I didn't want Hannah to find out like this, but you have to admit it is more fun now. Having both of us fawn over you as you get to try on all this feminine finery."

Looking up into her eyes, I didn't really know what to say. I wanted to leave, stop all this and hide, but I also wanted to go further. "This is beyond embarrassing-- but I want it to continue, I can't describe it."

"You just like humiliation. It's okay, I like humiliating you and it seems Hannah does too." She leaned in, giving me a tender kiss. "I'll make it all up to you later."

Hannah came in with the bra and a matching garter belt and some nude stockings. "There's also a garter belt that goes with this set that is absolutely lovely. Steven, you can go ahead and take off your panties. We'll get you back and covered in lace in no time." She said with a wink.

Slowly, I stepped out of my panties. Standing there with only my cage I somehow felt even more exposed. I tried covering it when Hannah stopped me. "Steve. You don't need to feel ashamed, I've already seen it." She swatted my hand away. Wrapping the garter around my waist she attached it behind me. Turning to Jen, "Would you mind helping me with Steve's stockings?"

"Not at all!" She peaked up.

Hannah handed her one stocking. Together, they got down on their knees before me. This would have been a dream if not for the cage around my cock. One at a time, they took a foot and slid the stocking up my leg, sending shivers through my entire body. Looking at each other, they both giggled.

"Well Steve, I'm glad you enjoy quality. These are very good stockings." Hannah informed me.

"Oh he does, whenever I wear these, he can never take his hands off my legs. Now I know why." Jen said with a chuckle.

Jen reached up, purposely stroking my cage and balls with the back of her hand as she grabbed the garter strap. Hannah followed suit, quickly attaching the clasp.

"Turn around now, Steven." Hannah ordered as she grabbed my hips to direct me. "Wow! You have an ass meant for this." She let out, squeezing one cheek.

I let out a gasp as she did eliciting more giggling from both.

"Yes he does! You should see him in a dress."

Genuinely, Hannah, "Oh yes please!"

I felt both girls attaching the back garters, with a tap on the butt, I couldn't tell from who, I was instructed to turn around. My face was perpetually red and I could feel my cage dripping.

"You're so wet, Steven!" Jen exclaimed, "I'm so glad you're caged or you'd be whipping that thing in our faces right now." I let out a deep moan. How I wish I was free right now, with these two beautiful girls on their knees in front of me. "You'd like that wouldn't you?" Jen huskily, her hand going to Hannah's leg. "Too bad you're all locked up. In that tiny, tiny cage."

Again, I moaned, buckling a bit at the knees. Jen began stroking my now stocking encased leg, keeping me standing straight. Hannah began rubbing my calf as well. Feeling both of them rubbing my stockinged legs was beyond intoxicating.

Begging, "Jen, please. Can I be unlocked!" Looking down at her, she deviously worked her hand up my legs stopping on my cage.

"I would but I left the key at home," she said with a fake pout. "I'm sorry."

Causing Hannah to laugh, "Poor Steven. Looks like your little clit is stuck in there."

That almost pushed me over the edge, I groaned and felt my cage drip. More precum oozed out of the tip.

Jen caught it. "Careful! We don't want any of this staining these lovely stockings." To my surprise, Jen licked her fingers clean letting out a moan of her own. "Mmm you taste so sweet." She rocked back on her legs. "Okay. Let's get your panties on."

Stepping into the leg holes, Jen and Hannah together brought the panties up my legs. Feeling them run over my stockings was heaven. They brought them up and around my hips, hugging my cage.

Hannah tapped the front of my panties, making a thud on the cage. "Now don't go dripping all over these. We don't want you making a mess in your panties."

Jen rubbing my thigh, "Why don't you help us up, Steven?"

I put out both my hands for them both to take. Watching them get up off their knees was a relief because I didn't know how much longer I could handle them down there.

Hannah began straightening the welt of my stockings, "Now, a lady always makes sure to have her stockings straight and welts even." She paced around me, fixing a garter behind me. Coming back in front, she snapped the garter on my right leg causing me to yelp. Letting out a chuckle, Hannah patted my thigh, "You'll get used to guys doing that too."

My face shot up to hers, terrified, "I don't want guys doing that! Let alone seeing me like this!"

Both girls laughed. Hannah, "You will someday."

"The first night we did this, we had take out and I made him come to the door with me. You should have seen his face," Jen tried to hold back her laughter, "he was so terrified. The delivery boy couldn't take his eyes off his legs though."

"Understandable. He has some killer legs." Hannah winked at me. "You may not want boys seeing you like this now, but once you see the effect all this has on them you will."

Jen stepped in, "Maybe someday. For now, he's all mine."

"Well if it were up to me, you'd be sucking so many cocks for a chance to even get out of the cage." Hannah said with an evil smile. "But let's finish getting you all prettied up!"

Jen helped slide the matching bra over my arms as Hannah attached it in the back. The bra had a bit of lift, letting me have the illusion of small breasts. Hannah fiddled with my chest, turning to Jen, "We have some inserts, nothing like forms but would bust him up a little."

Perking up, "I would like that."

Hannah turned to me, putting her hand on my face. "Aw he wants bigger boobs. I'll see what I can do."

My face went red again. Why did I speak up? Of course I wanted to see what I looked like but with Hannah here, all the embarrassment doubled.

Jen came over and kissed me, "I'm sorry if Hannah is being too mean. I think she really likes this. She doesn't get to talk this way with the other sissies who come here and well since she knows you, she knows she can be a little more of a tease."

I looked up to Jen, "it's okay-- I do like it. As much as I hate to admit."

She kissed me again, "I know."

Hannah came back with a small box. She pulled out two inserts. Coming over, she placed one in my bra, under my pec. On the second, she pinched my nipple causing me to quietly moan.

"I'm glad I brought these." Jen said, holding up my heels. She must have gone out to get them when she got the rest of the bras. She lowered to her knees again, slipping my first foot in. Hannah helped me balance, holding my hand, for the second.

"Wow. I was not expecting you to be able to handle heels so well. I'm impressed!" I looked up to Hannah and smiled, receiving one in return. "Okay. Are you ready to see yourself?" She asked.

I slowly nodded my head. Looking down at my chest, it actually looked like I actually had small breasts. I couldn't wait to see in the mirror. Jen took my hand and turned me around. I let out "Oh. Wow!"

Having lingerie that actually fits you changes everything. My legs looked amazing in these stockings, the heels only making them look longer. My panties hugged me tight, holding my cage against me reducing my bulge. You could see just the outline of it. With the inserts, the bra actually made me have a bust and I loved it.

Turning to Jen and then Hannah, "I love it. Thank you so much!"

"You look amazing, this color is really good with your pale skin. And I think this is the last time I will wear heels shorter than you, you're not allowed to be taller than me." Jen nugged my shoulder causing me to smile.

"Well you're both taller than me!" Hannah huffed, "but that's fine. Jen is right though, this color is great on your skin. The inserts really bring out your bust. All that's missing is some hair and make up! I would love to see you all out, Steven." Looking at Jen, "Does he have a girly name?"

Jen nodded, "Sasha. I had to come up with it on the spot."

"I think it suits her." Hannah said with a heartfelt smile.

"We'll have to get together sometime when you can see Sasha in all her glory." Jen came up to me, putting her arms around my waist. "Wouldn't that be fun, Sasha?"

I shook my head, nervously. As awkward as this has all been, I couldn't deny the thrill I was having. Having Hannah, another beautiful woman, seeing me like this and wanting to push me further only turned me on more. "It-- it would be fun" I loosely let out.

We ended up trying on a few more bras and decided on getting three sets. One black, a mauve, and the peach. I loved each but the peach was my favorite.

Getting everything read to check out, I was about to get changed but Jen stopped me. "Would you like to wear that whole set out? I know you really liked them."

I slowly nodded my head and Jen smiled at me. She helped me get the bra back on and took the tags with her. "I'll meet you at the counter. You can handle those stockings, right?"

Sitting on the bench, I slowly started working the first stocking up my leg. My cage instantly started throbbing. Something as small as just putting on stockings turned me on. Why did I have to tell Jen about my chastity fetish? My cock was aching but I couldn't deny how thrilling it felt. I didn't think it would feel like this. Just constant constriction. I was aware of every movement of my cock now. I loved it.

Attaching the garters, I finished putting on my clothes and exited the dressing room carrying my heels. Jen and Hannah were at the counter with all the lingerie bagged up.

Hannah giggled at the sight of me carrying my heels, "You're holding those just like a girl after a one night stand." Causing her to laugh more with Jen joining in. "You could have just worn them out, you looked very comfortable in them."

"Ha ha. They don't go with this outfit anyway." I joked.

Jen came over to me, taking the heels to put in the bag with the lingerie. "We could always change that."

I just stared at her, surprised she would suggest that. I didn't want to be out in public dressed.

"I'm just kidding, but we will be out someday."

We said our goodbyes to Hannah, hugging each of us. She even kissed me on the cheek, catching me by surprise. "I'm really looking forward to seeing the new you, Steven."

* * *

In the car, Jen turned to me, "I'm sorry that got so out of control. I really was not planning on Hannah to see you, at all. I hope you're not angry with me."

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