Corset Club Adventures - New Member

"Don't worry, I'll be right there behind you."

"Alright."

Taking a deep breath I took that first step outside, I felt like if it was going to happen, this was the moment when I was finally going to be humiliated for dressing up like this. I felt like any second now everyone I knew and their friends were going to jump out from behind the trees and bushes and point and laugh and take pictures to show everyone they knew that I wear women's clothing. But that never happened. With each step, I felt my confidence growing and the closer I got to my car the easier it became. When I finally had the game in my hand, I turned to Nick only to find that he wasn't behind me, he was back at the house standing inside the door.

Moving back towards the house, I was determined to tear Nick a new one. But before I could even take two steps, I was suddenly surprised to see Nick's neighbour Mr. Willis looking at me as he stood in his driveway. He was staring directly at me and I felt like he could see right through my disguise and knew that I wasn't dressed as I should be. As the horror of the situation overtook me, I tried not to suddenly take off running and continued to walk at a normal pace as I just smiled in his direction until he could no longer see me and I finally made it back into the house. Nick was doubled over in laughter and I could hardly believe my best friend had done that to me.

"How could you do that? You said you'd be right behind me!"

"Relax, you needed a push and I gave it to you."

"Mr. Willis saw me!"

"So? Mr. Willis is ninety years old and completely blind. If he saw anything, he saw a hot teenage girl and chances are you probably gave him the first hardon that he's had in ages."

Nick was certainly speaking the truth in between his fits of laughter, and I knew it. Everyone in the neighbourhood knew that Mr. Willis was blind and couldn't see anything at all. I had nothing to worry about. But I still wasn't happy about being tricked, however in light of my recent actions I probably deserved it.

"You really think I can turn someone on like this?" I asked once I'd finally given into the humour of the situation and had a good laugh along with my best friend.

"Trust me, you are going to be very popular."

For the next couple of hours, Nick and I hung out like we used to growing-up, except for the fact that we were both dressed like girls of course. But as we continued to game together, I started to notice that Nick seemed distracted. I suggested a game change, but that only worked for a short period as again I sensed he was distracted by something.

"You feeling alright?" I asked after watching Nick miss a jump that I knew he could make with his eyes closed.

"Yeah, why?"

"Well you seem a little distracted. I've seen you make that jump with ease a million times before. Something else has got your attention."

"Sorry, I am a bit distracted. I want to ask you something, but I'm worried about how you're going to react if I ask it." Nick looked genuinely concerned that I might be upset by whatever he wanted to ask me. Again, it didn't make any sense why Nick felt like he couldn't trust me.

"Nick look at me, how could I possibly react badly after you asked me to wear women's clothing with you."

Nick took a deep breath, then spoke.

"Alright, if you say so. Would you like a blowjob?"

I had to admit, I was a little shocked by his question, but I took it all in stride.

"What, from you?" I asked, trying not to sound dismissive.

"Well, you don't see anyone else here offering, do you?"

"No, that's certainly true."

"Look, ever since I saw you naked in the bathroom, I've been wanting desperately to suck your cock. I've honestly been interested in you for some time now, but I'll understand if you say no. I had to ask."

"And this is something you've done before?"

"Yes, and not to brag but I'm actually pretty good at it."

It took me a moment to consider Nick's offer. I'd never thought of this kind of thing before and it certainly would put a new twist on our friendship, but at the same time before today I'd never thought about the idea of wearing women's clothing and yet, here I am, actually enjoying myself.

"Sure, why not."

"Seriously? I mean that's great!"

Nick seemed genuinely excited about the idea of sucking me off as he positioned himself in front of me. Dropping to his knees, I lifted my hips to help Nick remove my panties and then slid to the edge of the seat to make things easier on him. When I felt his hand wrapped around my shaft the sensation of having someone else's hand on my cock caught me by surprise, and when I felt his lips wrap around the head, I couldn't hold back the gasp. This wasn't the first time I'd ever had someone blow me, but it was the first time that other person was a man.

Nick wasn't lying when he'd said that he was good at this, or that he had done this before. Again, I could see the signs of his confidence as he worked his mouth up and down my shaft and what he couldn't get in his mouth he continued to stroke with his hand. Every so often he would take my entire cock out of his mouth and use his tongue to work the head before swallowing it again. If I didn't know better, looking down between my legs I would swear that an actual girl was blowing me and not my best friend dressed as a girl.

After coming to terms with the fact that this was happening, I just simply let my head fall back and I just enjoyed the sensations altogether. I felt Nick take my entire cock out of his mouth for a few minutes longer than was usual based on his technique and was about to look up when I felt him take both of testicles into his mouth and gently suck on them before allowing each one to pop out of his mouth. It was an entirely new sensation to me and it I found it driving my arousal levels even higher.

As Nick resumed sucking my cock, I let my head fall back on the couch and my eyes close as Nick did his thing. When I felt Nick slip a hand under my ass, I wasn't sure what was going on. When I felt his finger pressing gently against my asshole it sent shockwaves through my body and my hips jumped at the foreign sensation. Nick didn't try to press into my asshole, he would only ever apply light pressure to press on it, occasionally even tapping on it with his finger. I groaned loudly at this point, having long since lost control and now just giving in to the sensations of having your best friend suck you off.

When I felt myself getting close to cumming it came as a great surprise to me, and I knew I wasn't far off at all. I tried to warn Nick but this only seemed to encourage him and before I could say anything more, I was blowing my load in my best friend's mouth. Wave after wave of intense pleasure washed over me as my whole body seemed to flex with each rope of sperm that I fired into Nick's mouth and down his throat. Nick surprised me once again as he swallowed every bit of my load that he could and didn't pull off until I was completely spent and soft. Leaning back in his kneeling position, Nick looked at me with a sense of pride before handing me back my panties, he smiled as I struggled to find the strength to pull them back on.

"Good?"

"Amazing." Was all I could say as my heartrate began to return to a normal rhythm.

"Well, I'm glad you enjoyed it. Like I said, I've been wanting to do that for a long time.

"Really?"

"Yes, ever since I joined the group and found that I enjoyed this kind of thing I've been wanting to share it with you. But I had to be sure that you would be open to it. You should know that the night you followed me I was planning on submitting your name for membership."

"Oh!" There was a moment of pride that I felt for the idea that Nick had felt I was good enough to be worthy of a referral to his secret club, instantly replaced by a feeling of embarrassment at how it had only taken a few hours for me to betray that sentiment. Once more I felt like I had betrayed Nick's friendship. He had me in mind all this time and I couldn't just be patient and wait.

"Don't worry. It's not how we normally do things, but what's done is done and now you'll soon be initiated as one of the sisters."

"Initiated?" Nothing had been said about an initiation. I had figured that the dressing up and photos were going to be enough.

"Yes, tomorrow night. The girls aren't wasting any time."

"No kidding. Are you allowed to tell me anything about this initiation?"

Nick paused for a moment and seemed to be contemplating something in his head. It must have been a rather serious thought as there was a clear pause in our conversation as the room went silent, except for the sound of the pause menu music from the video game we had all but forgotten about.

"Well I'm not supposed to tell you this, so this stays between you and I." I nodded in agreement and Nick continued.

"You'll go before the sisters and pledge your loyalty to them and once they accept, you'll be allowed to choose a female name for yourself."

"A female name?"

"Yes, we all have them. I go by Nicky. Everyone picks a name that starts with the same first letter of their male name. It may seem lazy, but it makes it easy to remember and to respond to when someone calls you by it. If I may, I'd like to make a suggestion for you."

"Okay."

"I think you should go with Monica. It keeps the first initial thing going so it should be easy for you to adjust to. Everyone else has basically done the same thing for the same reason. But you are free to choose something else if you'd like, it doesn't even have to start with M."

"No, I like it. Thank you, Nikki." Nick smiled at my use of his female persona.

"You're welcome, Monica." Nick replied in kind. It felt a little strange being referred to as a female, but I quickly found that I liked it.

"There's something else I should probably tell you about this ceremony. Before you're truly welcomed by the sisters, you'll be expected to prove yourself to them."

"What do you mean prove myself to them? Aren't those pictures you took earlier enough?"

"Those are just an insurance policy."

"So how do I prove myself to them?"

"You'll have to suck each of them off as well as get fucked by each of them. Call it a rite of passage."

"But I've never been fucked before." The idea of being penetrated by another man was a shock to me, but not for the reasons I would have expected.

"Don't worry, once again I can prepare you for that."

Nick moved quickly as he walked to the bathroom and I only assumed I was supposed to follow him. In the bathroom, I found him again pulling things from underneath the sink. This time it was another bottle and a small cone-shaped object I had never seen before.

"This butt plug will help you get used to having something inside your ass. This is the smallest one that I have so we'll start here and when you've gotten used to it and not experiencing any more discomfort you can move to something bigger."

"Oh, I see." Nick may have said it was small, but to me and my virgin asshole, it seemed massive.

"Just relax and lean over the toilet resting your hands on the tank. I'll get you started."

Assuming the position Nick had described, I felt Nick pull my panties down to the floor before I stepped out of them. Spreading my legs as wide as I could, I felt Nick apply a cool liquid generously to my asshole. A moment later he again reminded me to relax and breath and then I felt the butt plug being pushed against my ass. After some initial resistance, I felt it slide inside of me until it settled in fully. Once I had passed the initial feeling of wanting to push the foreign object out of my body, Nick let me put my panties back on and we left the bathroom. It was a strange sensation, feeling like I needed to take a massive shit, but trying to fight back against the urge to push.

"I want to show you something." Nick said once we had cleaned up and were back out of the bathroom. Nick moved to his computer, and I followed as I took the seat next to him and watched as he logged himself into a private web forum, including using a two point verification system on a phone I'd never seen him with before but somehow I didn't think he was about to explain to me. I could feel the butt plug inside of me, but it wasn't as uncomfortable as I had expected and sitting down helped me fight against the urge to push it out of me.

"This is our private forum where we communicate and share pictures and plan events. You aren't supposed to see this until you're an initiated member, but it's just a matter of time really so I have no worries showing it to you. Just don't say anything to anyone."

I sat and watched in awe as Nick clicked from one post to another, showing me pictures taken from different events and parties that he had been a part of with his so-called sisters. Some of the pictures appeared to show what looked just a casual hang out or get together that they were at, and some looked much more formal. I could tell that I was seeing pictures taken at different events and gatherings based on the backrounds in the image. In one post there were pictures of him with the other girls that I'd seen last night, and some I hadn't, and they were all dressed up very formally. When I saw shots of them standing with a woman in a wedding dress, I realized that these photos had clearly been taken at her wedding. When I saw Nick standing side by side with her in one shot and kissing her passionately in the next, I realized that this person must have been someone very important to Nick.

"I take it she was someone special to you?"

"That's Amber, one of my former sisters. She got married a couple months ago and of course we were all part of her bridal party. But yes, she is important to me, she's the one who brought me into the group."

"I see." I was pretty sure I knew just when Amber had gotten married, remembering the week that Nick had practically disappeared and essentially fallen off the map.

"But not all our get-togethers are so formal. To be honest more of our parties, especially when it's just us, usually end in an all-out orgy."

The next few groups of pictures that Nick showed me were completely different from what I'd already seen. Every picture showed Nick with one or more of his sisters in some state of undress sucking and fucking each other. It was quite a sight and I could feel myself reacting to the imagery. When the photos stopped changing, I looked over to Nick and found that he wasn't watching the screen but he was watching me. Suddenly I felt a need to prove to Nick that I was fully invested in this.

"Nick, sorry Nikki, I want to return the favour." I blurted out.

"What favour?" Nikki's smile told me she knew what I was talking about, but wanted to hear me say it.

"I want to suck your cock." I said, perhaps a little louder than necessary, surprising myself with the volume and intent in my saying it.

"Are you sure? You don't have to if you don't want to."

"No, I want to. Besides, I'm going to have to do it tomorrow anyway."

"Alright, if you say so."

Together Nick and I moved back to the couch but this time he sat as I knelt between his legs. I didn't have the confidence or the skills that Nick had, so I tried to remember everything that he had done and just repeat it. It took a few moments longer for me to go from stroking Nick, who was already hard by the time I got his panties off, to actually getting his cock in my mouth. But when I did, I found the taste wasn't as bad as I was expecting. It was a little salty from sweat, but I managed to get past that pretty quickly. As I started to lower my lips and take more of his shaft into my mouth, I felt a hand on my head holding me back.

"Don't go too far or you'll gag. With time and practice you'll be able to get more and more in your mouth, but for now, don't push too far."

Having Nick guide and instruct me was reassuring and it gave me the confidence to continue. I tried to remember everything that he had done, including removing his entire cock from my mouth and using my tongue to work the head and when I looked up, I felt a sense of pride to see that he was enjoying my first blowjob. This was the encouragement I needed to increase my efforts as I was determined to fully reciprocate what Nick had done for me. The next time I felt his hands on my head, he was again pulling me back.

"Careful, I'm about to cum." Nick groaned. But that didn't stop me, it only spurred me on and I redoubled my efforts. I felt myself swell with pride knowing I had managed to get Nick this close, but I wasn't going to stop here. Nick continued to try to stop me and I could feel him getting tense, but I wasn't going to stop and when he let out a loud groan, I felt him fill my mouth to the point of overflowing with his load. I remembered then that he had swallowed when this had happened and I proceeded to do the same. I was a bit of a mess compared to him when I was done, some of Nick's cum now dripping down my chin, but after Nick made himself decent, he helped me touch up my makeup.

"Monica, that was incredible. Are you sure you've never done that before?"

"Nope, that was the first time for me."

"Well, you are going to be very popular in the group, I can guarantee that. You're a natural cock sucker."

"Well thank you." I said, giving a mock curtsey before we both started laughing. This bit of humour was really helping me to relax.

"So how is your ass feeling?" Nick asked when we'd calmed down.

"You know, I don't even notice the butt plug anymore."

"Good, you're ready to move up to the next size. Follow me."

Following Nick back into the bathroom, he had me squat over the toilet and remove my current butt plug. When I asked him why he told me it could sometimes get a bit messy and would explain later about how to deal with that sort of issue. Luckily for us however, that wasn't the case and we quickly got the next size up in my ass before getting dressed again.

After that, things went mostly back to normal, or at least as normal as two teenage males wearing women's clothing could be. Just before Nick's parents returned home, we changed back to our male clothing but kept our bra and panties on underneath our clothes as we joined Nick's parents for supper. After supper, we returned to Nick's basement apartment and hung out like we normally did. Nick had suggested that I spend the night as it would give us as much time as possible to get ready for tomorrow night.

When it came time to get ready for bed, Nick smiled as he said he had just the thing for me to sleep in. From his closet, he produced two matching nightgowns, one in light blue and the other in yellow. He handed me the yellow one and its matching panties and we quickly stripped and changed. The nightgown hung just down below my ass, leaving my now hairless legs fully exposed, something Nick took great pleasure in teasing me with by running his hands over my smooth legs. It was quite the sensation, and it was having quite the effect on me as well.

When we finally decided to turn in for the night, we didn't worry about hiding in separate rooms like we used to as we'd already seen everything each of us had to offer and it seemed rather pointless. Just as we were climbing into bed, however, Nick surprised me once more.

"Monica, can I fuck you?"

"What?"

"Can I fuck you? When I was sliding that butt plug into your ass, I couldn't help but picture it as my cock instead and I would love the chance to fuck you. Especially since by the time I get my turn tomorrow night you'll likely be a sloppy mess."

"I don't get any say in who fucks me first?"

"No. You may still be blowing one of the other sisters when it happens."

"Well since it's my virgin ass I think I should get a say in who gets it first and I want you to be the one to pop my cherry."