My Girlfriend s Girlfriend
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My First Girlfriend Vol.2 free porn video
Chapter 7: More Panties
I had just received the best handjob of my life. I lay cuffed to her bed, my smooth slender body glistening with sweat. It had just hit me that my loving, caring girlfriend had locked my cock back up in a pink chastity cage. My heart sunk. But I remembered my determination to be a perfect boyfriend for her. Once she took the gag out, I meekly asked her when she would let me out next. She replied "When the time is right, sweety" as she planted a a warm kiss on my quivering mouth and unlocked the handcuffs. "In the meantime, you're going to start wearing girl's panties every day." she casually declared. "What?" I reflexively demanded. "You heard me" she replied confidently before explaining "I think it suits you now that you're nice and smooth. Besides, your parts are all locked up anyway - may as well keep 'em nice and secure" she giggled and gave my cage a little 'jiggle'. I opened my mouth to argue but she quickly warned me that any resistance would lead to more time in chastity, so I gave in right away. She then pulled a shopping bag out from her closet and presented it to me. "These are my gift to you. They are your size and you can keep them." I opened the bag to find a dozen or so pairs of girly panties; some briefs, some bikini cut, and even a couple thongs, shades of pink, yellow, turquoise, or white, some adorned with lace or bows. All unmistakably girly. I stared at her stunned. I wasn't sure whether to feel grateful for the gift or humiliated at this new enforced wardrobe adjustment (which she had apparently been planning long enough to do some shopping beforehand?).
"You didn't think I was going to keep lending you mine did you?" she asked rhetorically in a teasing tone. I shook my head. truthfully, I didn't realize I was going to be wearing panties on a regular basis. I thought maybe it would be a once in a while thing when we fooled around. Now apparently I have to wear them every day? To school? Around my friends? Would I even be able to act normal around people knowing I'm hiding something so weird and embarrassing? I remembered what happened to a k** who got caught wearing 'tighty whiteys' - he never heard the end of it. Imagine if someone saw me in a pink lacy thong.... the very thought was terrifying. I already get made fun of for not being masculine enough. She interrupted my downward spiral of worry and dread to deliver more bad news: because she had a busy week ahead of her, she wouldn't be able to see me at all until next weekend. I started to think that maybe I wouldn't have to wear panties during the week because she wouldn't be around to check on me!
Unfortunately for me, she had thought of that already, and had a solution in mind - a very embarrassing one. "Catherine is going to check on you every day at school." (Catherine was one of my good female friends at my school. Rebecca had met her through me months ago of course, but I didn't realize they had a friendship of their own. Apparently they had actually been hanging out a fair bit unbeknownst to me). I cautiously rebutted "Oh... I don't think she'd want to be involved in this sort of thing. Might make her uncomfortable right? I mean how would we even ask?". I thought she'd at least have to think about it, but no. "She's already agreed to it. She owed me a big personal favor, and she's also doing it for your sake. I told her if she couldn't do it, I'd have to get Kristen to do it. And you you know how much of a gossip Kristen can be. Catherine will keep our secret safe. She cares about both of us, and would never fuck you over, or lie to me. Trust me, this is the best option."
I was a deer-in-the-headlights. My girlfriend had just sprung so much on me so quickly. I needed a minute to process it all. How long had she been planning all this? Not only had she gone out and bought a bunch of panties for me, she had arranged for another girl to keep tabs on me? And holy shit, my friend Catherine knows about the panties? And she's going to see me wearing them? Does she know about the chastity too? Fuck. I mean I guess if I had to choose any friend to know an embarrassing secret of mine, it would be Catherine. She was very sweet and kind, down to earth and approachable (as well as smart, funny and pretty). She was a gem. to be honest I sort of had a crush on her at one point but we moved passed that and became close friends instead. "You look glum, my darling" she spoke to me in a sympathetic tone. I told her it was just a lot to take in. "I know baby. I'm sorry I kept secrets from you but I didn't want to risk freaking you out". I was pretty fucking freaked out at that moment, but she spoke to me soothingly, gave me lots of kisses, rubbed my shoulders and reminded me how much she loves me. I felt a little bit infantilized by this combination of humiliation, control, and affection. It was both uncomfortable and hypnotizing. I felt trapped, yet safe. Why was my girlfriend going to to such lengths to make me more girly? Don't girls like macho guys? Then again I never stood any chance of being macho at all and she still dated me and let me fuck her. I guess she just likes more feminine guys? Oh my god what if she actually prefers girls? Is she bi? Or a lesbian in denial? Is she trying to turn me into a full girl? Mysteriously, that last thought caused a little surge of excitement through my body. It might have been arousal, but I convinced myself it was fear. The thought of discarding ALL the pressures and stereotypes I could never fit; completely abandoning masculinity... I'd always been fighting against my nature to appear strong, tough, decisive - all that macho shit - and the best I could ever do was just barely adequate. I'd always been conditioned to assume my only option in life was to conform and strive for the ideals of manhood. I could never bring myself to contradict those ideals. Sure, on one hand it would be a massive relief to escape the pressure to be dominant (a goal that I've always fallen short of), but the social cost would be unthinkable; I would be a laughingstock, a pariah. Worse than an outcast, I would be a disgrace. No. I must do the best I can to retain my manhood, at least to the public. What I do with Rebecca behind closed doors is one thing, but everyone else will see me as a man. Or at least a boy. A straight boy. I think. To be honest I get called 'gay' so much at school sometimes I wonder...
Rebecca interrupted my self-psychoanalysis "So every day at school this week, you will walk with Catherine to her house for lunch. Then you can show her your panties before going back to class. She's fully aware of all this and she agreed to help us. You don't have to be shy with her. It might even be fun! And best of all, I know you can't cheat on me since your dick is locked up haha." She coaxed me into putting on a pair of my new underwear (some white briefs with little pink flowers all over), let me get dressed and sent me on my way with the shopping bag full of panties.
Chapter 8: Catherine
Since the first time we'd had sex a couple weeks ago, my girlfriend had made me try on her panties, gotten me to shave my body smooth, locked my dick into chastity, put me in bondage for the first time, and now she had given me a bunch of panties which she was coercing me to wear every day. I was confused over all of it. I was starting to feel less and less in control. It wasn't totally unexpected - she had every reason to be the dominant one in the relationship (experience, looks, status, confidence. She was above me in every way). I just don't understand what she sees in me. But she seems more into me than ever now that I've started doing whatever she says, so I'm going to keep using that strategy going forward. If that means letting my friend Catherine see me in girly panties, then so be it.
Monday morning getting dressed I felt so nervous and paranoid I thought I was going to throw up. I felt like I was getting ready to jump out of a plane. I laid out my clothes. Typical outfit; jeans, T shirt, hoody, socks, and last but not least - a pair of white briefs. It was the plainest pair I could find in the selection Rebecca had chosen for me. All the rest either had feminine decorations or bright colors. I figured the least noticeable ones would be the safest way to start. I pulled them up my smooth legs and over my chastity device. The tight hug of the soft material was undeniably pleasant. This is how girls feel all the time? I felt envious for a split second before remembering that I am being forced by a girl to wear these every day. Like it or not, I guess I'm going to get used to the feeling of panties. I scrambled to get my pants on as quickly as possible to cover my dainty undergarments. I did the rest of my usual morning things and headed out.
The walk to school felt a bit different, but I forced myself to get used to it, not wanting to dwell on my predicament. In class I made sure to keep the bottom of my hoody down over the waistband of my jeans. Overlap at all times. Nothing peeking out. I tried to put it out of my mind and get through the day normally, but there was always a nagging paranoia. If some asshole decided to pants me as a joke, it would be game over. Fortunately everyone minded their business all morning and soon enough it was lunch time. It started to hit me that regardless of all my efforts and wishes, my underwear was about to be exposed. Part of me started praying that Rebecca was just messing with me and Catherine had no idea idea about any of this. I went to meet her at her locker as I had been instructed. When she saw me, she gave a coy little smile and I knew right away that Rebecca was telling the truth and she knew everything. I blushed so hard I almost passed out.
"Hey buddy, so we're going to my house for lunch right?" she winked. "y- yeah... So.... Rebecca talked to you?" I stumbled over my question because I didn't want to hear the answer. "Sure did. We can talk about it when we're alone if you want." Catherine was an angel and clearly didn't have any intention of denigrating me or taking joy from my discomfort. I felt lucky to have a friend as accepting as her. I couldn't imagine going through this with any of Rebecca's other friends. We strolled to her place and she told me about her weekend. We acted normal and I started to feel normal. But when we walked up her driveway and through her front door, I started to feel anxious again. She broke the ice as kindly as possible;
"SO. You and Rebecca have been trying some new things I hear?" I went along with it "uhh yeah I guess thats what it is." She could see my nervousness and reassured me "Its not really that weird you know - boys wearing girls' clothes. Cross dressing is super common. Its something a lot of guys think about trying. Most of them are just too insecure. But anyway, I know you're only doing it for Rebecca which is really sweet of you, so don't be ashamed." I thanked her for being so cool about it and awkwardly asked where we should do 'the next part'. She assured me no one else is home and we can do it right there in the kitchen while she warmed up her lunch. She stood back and gestured for me to proceed. With shivers going up my spine I carefully undid my jeans and slid them down just enough to reveal my crotch. With one last deep breath I pulled up my hoody, putting my panties on display for sweet, kind Catherine.
"Hey those aren't even that bad" she remarked. "They're basically just briefs. They could even be like, men's athletic underwear." I pulled up my jeans and informed her that all my remaining pairs were not nearly as subtle. She laughed and said she can't wait to see. I didn't mind her joking around, in fact it eased my anxiety a bit to make light of this weird situation I'm in. Having gotten through the worst of it, I felt a bit better and the rest of the day went by fine.
The next morning was a tough one because I had to choose one of the remaining pairs - which were all obviously not for boys. I settled for a pair of turquoise bikini style. It seemed like the least offensive color, but the shape and fit of these ones still didn't leave me much masculine dignity. I would just cover them at all times just like yesterday. They started to ride up my ass a bit at school, so between classes, I had to go into a bathroom stall and try to adjust them. I was terrified some nosy jerk would catch a glimpse through the crack of the stall door, so I waited until no one was in the bathroom but me. It was actually kind of a rush sneaking around with a sexy secret under my clothes... Lunch time I went with Catherine again. It was much easier now that a precedent had been set. We talked about normal stuff on the walk, and we were basically just hanging out like normal. We went in the kitchen again and I presented myself to her like before. This time she was a little more amused by my choice. "Great color!" she commented, then added "I think I have that same pair but in red". Involuntarily the image of Catherine's curvy body in sexy red panties flashed into my head. I found myself filled with unwanted arousal which turned to shame when I noticed that my pants were still down. I laughed nervously, pulled my jeans right back up, and tried to act normal until we got back to class. Catherine was very cute. No denying that. But I was long-since over my crush on her and was happy to have her as a friend and confidant. Still, the knowledge of what kind of panties she wears woke up all sorts of teenage thoughts that were hard to shake.The shape of her ass. The tiny crease between her thigh and pubic region. I tried my best to focus on what my teachers were saying, but the day felt like it would never end. Luckily it did. Now normally I would cleanse myself of these naughty thoughts by masturbating. After I cum I can control myself and focus and be normal and decent again. But the chastity wouldn't allow me that solace. I had no choice but to wait it out, distract myself, and hope the sexy images of my female friend would fade away.
They sort of did, but the problem is I woke up the next morning with the knowledge that I would be seeing Catherine again - and worse yet - I would be showing her my underwear again. I was tense all morning. worried I'd do or say something weird or perverted in front of her. Or in front of anyone for that matter. I was surrounded by people who were not nearly as kind of discreet as her, and today my best option was a a pair of yellow briefs with black trim. They somehow felt more masculine than all the pink pairs, but if anyone saw them it would still make me look like a sissy.
Lunch rolled around and I went to Catherine's locker as usual. This time some friends of hers were hanging around chatting. I got nervous. I definitely didn't want any attention from our classmates. I walked over apprehensively, and greeted the group quietly. Catherine told her friends she was going home for lunch and she'd see them back at class. One of the girls made some corny joke about Cathy and I hooking up over lunch break. Catherine laughed it off and pointed out that "No way! he's dating my best friend haha". Her Best friend? Catherine was Rebecca's best friend? I felt very silly for not realizing how close they had become. But that was the least of my worries. We walked to her house and I took my mind off things by asking random stuff about her friends group. Apparently two of her male friends were competing for the attention of her friend Summer. Typical high school stuff. Catherine made some offhand remark about how "pretty girls like that have so much power over guys". That really hit home for me as I walked with my genitals locked in pink plastic and wrapped in tight yellow polyester.
When we got to her house, we found that her sisters were both home. We definitely weren't doing our 'show and tell' game in the kitchen this time. We'd have to go up to her bedroom. I know it was purely circumstantial, and it was literally physically impossible for anything to happen between her and I, but I still felt sexual tension filling the air like a tingly mist. Maybe it's just that I hadn't cum in a couple days now, and the feeling of panties on your skin is inherently sexy. She sat on her bed, eating her chicken burrito and lightheartedly told me to get on with it. "Yes ma'am" I chuckled as I undid my jeans. When I revealed my yellow and black selection, her eyes lit up.
"Ooooohhh no friggin way!" I asked what the excitement was about. She explained "I own that exact same pair haha and I'm literally wearing them today! how crazy is that?" I stuttered out something along the lines of "Really? You're k**ding right?" I hadn't even meant to challenge her claim, but without missing a beat she offered to 'show me proof'. She stood up on her bed and slid her summer dress up over her wide hips so I could clearly see (at eye level) that she was indeed wearing the same yellow briefs with the black trim. I could also see the smooth lightly tanned skin of her thighs, the delicate crease of her groin, the slight bulge of her mound, and the curvy swell of her hips. "What are the odds?" she marveled as she pulled her dress back down and went back to her burrito. I agreed it was pretty crazy (while I tried to mentally calm my confined penis). It had been a flashbomb of feminine sexuality and intimacy, and my little locked up dick definitely took notice. It was pretty uncomfortable but I sat down and tried to act normal. She sat and thought quietly for a moment and then pondered aloud "Hey. sooo you keep having to show me your underwear, and that just now was the only time you've seen mine. Maybe its more fair to you if I show you mine every time from now on? like, solidarity y'know?"
Jesus Christ, she was suggesting flashing her panties to me again tomorrow and the next day? I was already too horny for my own comfort, but for lack of any better response i blurted out "Sure okay."
"Cool! Yeah its more fair this way. I feel bad seeing you so vulnerable. This will be easier on my conscience haha." I was in a daze as we walked back to class. Trying to wrap my head around how her innocence, compassion, and loyalty were causing her to subject me to sexual torture - the torture of arousal without release. What a fucked up situation Rebecca put me in. I was frustrated with her, but I also would have done literally anything on earth to have her unlock me. I was frustrated but extremely turned on. I wasn't sure if I would cry or cum in my chastity device. Spent the night studying to try and keep my mind off of Catherine's ass in panties, my ass in panties, Rebecca's ass in general....
Thursday; just two more days of this hell and then I can see Rebecca and she will let me out of this cage and everything will be fine again. I was out of the more conservative pairs of underwear and now I was into the thongs and the pink stuff. I decided that feel was now more important to me than color, thus I put on a pink bikini thing with a thick black elastic waistband. They looked slutty, but I was not ready to wear a thong all day. Not yet at least. I daydreamed right through my morning classes. I still loved Rebecca but all this time spent with lovely Catherine and sexy panties was really testing my mental fortitude. Back at Catherine's place we had the house to ourselves once, but she suggested we hang out in her room again because its 'more chill'. I proceeded with what was now routine; I pulled my jeans down and exposed my slutty new underwear. She raised her eyebrows a bit and joked that I was a 'naughty girl'. That alone turned me on more than I can express. As promised, she stood up, peeled her black leggings down to mid thigh and pulled up her sweater so I could clearly see her red thong. she even did a spin so I got the full picture. My jaw dropped right open, which she obviously noticed.
"What? oh, have you never seen a thong before? I'm sure Rebecca must wear them all the time." My heart was pounding. Two days ago the mere mention of her panties put me on the edge, and she had just given me a full view of her round ass in a silky red thong. She softly walked over to me "Are you okay dude? You're breathing kinda heavy" She came right up face to face with me, both of our pants still down. I said I was fine, just a bit warm. I tried to compose myself while she looked me over checking for signs of illness or distress. Such a caring friend. Why the fuck were her pants still down? I couldn't help but notice that our genitals were less than a foot apart. If it weren't for this cage on my cock I would have bent her over right there and ruined her whole week. Instead I assured her that I was fine and pulled my pants up. I thanked her for doing this with me and making me feel so 'comfortable'. It was a little disingenuous because I was NOT comfortable, but what else can you say when your best female friend shows you her fucking thong out of 'solidarity'?
I was a zombie in my afternoon classes. I went home and took a very cold shower. Something I probably should have done every day this week. Fuck. Catherine is so fucking hot. How does a girl that small have an ass that big? Why is she so nice to me? Why isn't she weirded out by me wearing panties and being locked up? what did Rebecca tell her? These questions polluted my mind until I fell asleep. I dreamt that I was shrunk down to the size of a cat, and Rebecca and Catherine towered over me as my owners. They were dressed in latex lingerie and all 3 of us cuddled on a giant bed. My alarm went off before it could become a wet dream.... I woke up with a sense of determination. I just had to get through one more day. Then I would negotiate with Rebecca to get this plastic cage taken off me for good. I didn't even mind the panties, and I loved the excuse to hang out with Catherine more, but holy fuck this chastity thing will be the end of me.
I had just received the best handjob of my life. I lay cuffed to her bed, my smooth slender body glistening with sweat. It had just hit me that my loving, caring girlfriend had locked my cock back up in a pink chastity cage. My heart sunk. But I remembered my determination to be a perfect boyfriend for her. Once she took the gag out, I meekly asked her when she would let me out next. She replied "When the time is right, sweety" as she planted a a warm kiss on my quivering mouth and unlocked the handcuffs. "In the meantime, you're going to start wearing girl's panties every day." she casually declared. "What?" I reflexively demanded. "You heard me" she replied confidently before explaining "I think it suits you now that you're nice and smooth. Besides, your parts are all locked up anyway - may as well keep 'em nice and secure" she giggled and gave my cage a little 'jiggle'. I opened my mouth to argue but she quickly warned me that any resistance would lead to more time in chastity, so I gave in right away. She then pulled a shopping bag out from her closet and presented it to me. "These are my gift to you. They are your size and you can keep them." I opened the bag to find a dozen or so pairs of girly panties; some briefs, some bikini cut, and even a couple thongs, shades of pink, yellow, turquoise, or white, some adorned with lace or bows. All unmistakably girly. I stared at her stunned. I wasn't sure whether to feel grateful for the gift or humiliated at this new enforced wardrobe adjustment (which she had apparently been planning long enough to do some shopping beforehand?).
"You didn't think I was going to keep lending you mine did you?" she asked rhetorically in a teasing tone. I shook my head. truthfully, I didn't realize I was going to be wearing panties on a regular basis. I thought maybe it would be a once in a while thing when we fooled around. Now apparently I have to wear them every day? To school? Around my friends? Would I even be able to act normal around people knowing I'm hiding something so weird and embarrassing? I remembered what happened to a k** who got caught wearing 'tighty whiteys' - he never heard the end of it. Imagine if someone saw me in a pink lacy thong.... the very thought was terrifying. I already get made fun of for not being masculine enough. She interrupted my downward spiral of worry and dread to deliver more bad news: because she had a busy week ahead of her, she wouldn't be able to see me at all until next weekend. I started to think that maybe I wouldn't have to wear panties during the week because she wouldn't be around to check on me!
Unfortunately for me, she had thought of that already, and had a solution in mind - a very embarrassing one. "Catherine is going to check on you every day at school." (Catherine was one of my good female friends at my school. Rebecca had met her through me months ago of course, but I didn't realize they had a friendship of their own. Apparently they had actually been hanging out a fair bit unbeknownst to me). I cautiously rebutted "Oh... I don't think she'd want to be involved in this sort of thing. Might make her uncomfortable right? I mean how would we even ask?". I thought she'd at least have to think about it, but no. "She's already agreed to it. She owed me a big personal favor, and she's also doing it for your sake. I told her if she couldn't do it, I'd have to get Kristen to do it. And you you know how much of a gossip Kristen can be. Catherine will keep our secret safe. She cares about both of us, and would never fuck you over, or lie to me. Trust me, this is the best option."
I was a deer-in-the-headlights. My girlfriend had just sprung so much on me so quickly. I needed a minute to process it all. How long had she been planning all this? Not only had she gone out and bought a bunch of panties for me, she had arranged for another girl to keep tabs on me? And holy shit, my friend Catherine knows about the panties? And she's going to see me wearing them? Does she know about the chastity too? Fuck. I mean I guess if I had to choose any friend to know an embarrassing secret of mine, it would be Catherine. She was very sweet and kind, down to earth and approachable (as well as smart, funny and pretty). She was a gem. to be honest I sort of had a crush on her at one point but we moved passed that and became close friends instead. "You look glum, my darling" she spoke to me in a sympathetic tone. I told her it was just a lot to take in. "I know baby. I'm sorry I kept secrets from you but I didn't want to risk freaking you out". I was pretty fucking freaked out at that moment, but she spoke to me soothingly, gave me lots of kisses, rubbed my shoulders and reminded me how much she loves me. I felt a little bit infantilized by this combination of humiliation, control, and affection. It was both uncomfortable and hypnotizing. I felt trapped, yet safe. Why was my girlfriend going to to such lengths to make me more girly? Don't girls like macho guys? Then again I never stood any chance of being macho at all and she still dated me and let me fuck her. I guess she just likes more feminine guys? Oh my god what if she actually prefers girls? Is she bi? Or a lesbian in denial? Is she trying to turn me into a full girl? Mysteriously, that last thought caused a little surge of excitement through my body. It might have been arousal, but I convinced myself it was fear. The thought of discarding ALL the pressures and stereotypes I could never fit; completely abandoning masculinity... I'd always been fighting against my nature to appear strong, tough, decisive - all that macho shit - and the best I could ever do was just barely adequate. I'd always been conditioned to assume my only option in life was to conform and strive for the ideals of manhood. I could never bring myself to contradict those ideals. Sure, on one hand it would be a massive relief to escape the pressure to be dominant (a goal that I've always fallen short of), but the social cost would be unthinkable; I would be a laughingstock, a pariah. Worse than an outcast, I would be a disgrace. No. I must do the best I can to retain my manhood, at least to the public. What I do with Rebecca behind closed doors is one thing, but everyone else will see me as a man. Or at least a boy. A straight boy. I think. To be honest I get called 'gay' so much at school sometimes I wonder...
Rebecca interrupted my self-psychoanalysis "So every day at school this week, you will walk with Catherine to her house for lunch. Then you can show her your panties before going back to class. She's fully aware of all this and she agreed to help us. You don't have to be shy with her. It might even be fun! And best of all, I know you can't cheat on me since your dick is locked up haha." She coaxed me into putting on a pair of my new underwear (some white briefs with little pink flowers all over), let me get dressed and sent me on my way with the shopping bag full of panties.
Chapter 8: Catherine
Since the first time we'd had sex a couple weeks ago, my girlfriend had made me try on her panties, gotten me to shave my body smooth, locked my dick into chastity, put me in bondage for the first time, and now she had given me a bunch of panties which she was coercing me to wear every day. I was confused over all of it. I was starting to feel less and less in control. It wasn't totally unexpected - she had every reason to be the dominant one in the relationship (experience, looks, status, confidence. She was above me in every way). I just don't understand what she sees in me. But she seems more into me than ever now that I've started doing whatever she says, so I'm going to keep using that strategy going forward. If that means letting my friend Catherine see me in girly panties, then so be it.
Monday morning getting dressed I felt so nervous and paranoid I thought I was going to throw up. I felt like I was getting ready to jump out of a plane. I laid out my clothes. Typical outfit; jeans, T shirt, hoody, socks, and last but not least - a pair of white briefs. It was the plainest pair I could find in the selection Rebecca had chosen for me. All the rest either had feminine decorations or bright colors. I figured the least noticeable ones would be the safest way to start. I pulled them up my smooth legs and over my chastity device. The tight hug of the soft material was undeniably pleasant. This is how girls feel all the time? I felt envious for a split second before remembering that I am being forced by a girl to wear these every day. Like it or not, I guess I'm going to get used to the feeling of panties. I scrambled to get my pants on as quickly as possible to cover my dainty undergarments. I did the rest of my usual morning things and headed out.
The walk to school felt a bit different, but I forced myself to get used to it, not wanting to dwell on my predicament. In class I made sure to keep the bottom of my hoody down over the waistband of my jeans. Overlap at all times. Nothing peeking out. I tried to put it out of my mind and get through the day normally, but there was always a nagging paranoia. If some asshole decided to pants me as a joke, it would be game over. Fortunately everyone minded their business all morning and soon enough it was lunch time. It started to hit me that regardless of all my efforts and wishes, my underwear was about to be exposed. Part of me started praying that Rebecca was just messing with me and Catherine had no idea idea about any of this. I went to meet her at her locker as I had been instructed. When she saw me, she gave a coy little smile and I knew right away that Rebecca was telling the truth and she knew everything. I blushed so hard I almost passed out.
"Hey buddy, so we're going to my house for lunch right?" she winked. "y- yeah... So.... Rebecca talked to you?" I stumbled over my question because I didn't want to hear the answer. "Sure did. We can talk about it when we're alone if you want." Catherine was an angel and clearly didn't have any intention of denigrating me or taking joy from my discomfort. I felt lucky to have a friend as accepting as her. I couldn't imagine going through this with any of Rebecca's other friends. We strolled to her place and she told me about her weekend. We acted normal and I started to feel normal. But when we walked up her driveway and through her front door, I started to feel anxious again. She broke the ice as kindly as possible;
"SO. You and Rebecca have been trying some new things I hear?" I went along with it "uhh yeah I guess thats what it is." She could see my nervousness and reassured me "Its not really that weird you know - boys wearing girls' clothes. Cross dressing is super common. Its something a lot of guys think about trying. Most of them are just too insecure. But anyway, I know you're only doing it for Rebecca which is really sweet of you, so don't be ashamed." I thanked her for being so cool about it and awkwardly asked where we should do 'the next part'. She assured me no one else is home and we can do it right there in the kitchen while she warmed up her lunch. She stood back and gestured for me to proceed. With shivers going up my spine I carefully undid my jeans and slid them down just enough to reveal my crotch. With one last deep breath I pulled up my hoody, putting my panties on display for sweet, kind Catherine.
"Hey those aren't even that bad" she remarked. "They're basically just briefs. They could even be like, men's athletic underwear." I pulled up my jeans and informed her that all my remaining pairs were not nearly as subtle. She laughed and said she can't wait to see. I didn't mind her joking around, in fact it eased my anxiety a bit to make light of this weird situation I'm in. Having gotten through the worst of it, I felt a bit better and the rest of the day went by fine.
The next morning was a tough one because I had to choose one of the remaining pairs - which were all obviously not for boys. I settled for a pair of turquoise bikini style. It seemed like the least offensive color, but the shape and fit of these ones still didn't leave me much masculine dignity. I would just cover them at all times just like yesterday. They started to ride up my ass a bit at school, so between classes, I had to go into a bathroom stall and try to adjust them. I was terrified some nosy jerk would catch a glimpse through the crack of the stall door, so I waited until no one was in the bathroom but me. It was actually kind of a rush sneaking around with a sexy secret under my clothes... Lunch time I went with Catherine again. It was much easier now that a precedent had been set. We talked about normal stuff on the walk, and we were basically just hanging out like normal. We went in the kitchen again and I presented myself to her like before. This time she was a little more amused by my choice. "Great color!" she commented, then added "I think I have that same pair but in red". Involuntarily the image of Catherine's curvy body in sexy red panties flashed into my head. I found myself filled with unwanted arousal which turned to shame when I noticed that my pants were still down. I laughed nervously, pulled my jeans right back up, and tried to act normal until we got back to class. Catherine was very cute. No denying that. But I was long-since over my crush on her and was happy to have her as a friend and confidant. Still, the knowledge of what kind of panties she wears woke up all sorts of teenage thoughts that were hard to shake.The shape of her ass. The tiny crease between her thigh and pubic region. I tried my best to focus on what my teachers were saying, but the day felt like it would never end. Luckily it did. Now normally I would cleanse myself of these naughty thoughts by masturbating. After I cum I can control myself and focus and be normal and decent again. But the chastity wouldn't allow me that solace. I had no choice but to wait it out, distract myself, and hope the sexy images of my female friend would fade away.
They sort of did, but the problem is I woke up the next morning with the knowledge that I would be seeing Catherine again - and worse yet - I would be showing her my underwear again. I was tense all morning. worried I'd do or say something weird or perverted in front of her. Or in front of anyone for that matter. I was surrounded by people who were not nearly as kind of discreet as her, and today my best option was a a pair of yellow briefs with black trim. They somehow felt more masculine than all the pink pairs, but if anyone saw them it would still make me look like a sissy.
Lunch rolled around and I went to Catherine's locker as usual. This time some friends of hers were hanging around chatting. I got nervous. I definitely didn't want any attention from our classmates. I walked over apprehensively, and greeted the group quietly. Catherine told her friends she was going home for lunch and she'd see them back at class. One of the girls made some corny joke about Cathy and I hooking up over lunch break. Catherine laughed it off and pointed out that "No way! he's dating my best friend haha". Her Best friend? Catherine was Rebecca's best friend? I felt very silly for not realizing how close they had become. But that was the least of my worries. We walked to her house and I took my mind off things by asking random stuff about her friends group. Apparently two of her male friends were competing for the attention of her friend Summer. Typical high school stuff. Catherine made some offhand remark about how "pretty girls like that have so much power over guys". That really hit home for me as I walked with my genitals locked in pink plastic and wrapped in tight yellow polyester.
When we got to her house, we found that her sisters were both home. We definitely weren't doing our 'show and tell' game in the kitchen this time. We'd have to go up to her bedroom. I know it was purely circumstantial, and it was literally physically impossible for anything to happen between her and I, but I still felt sexual tension filling the air like a tingly mist. Maybe it's just that I hadn't cum in a couple days now, and the feeling of panties on your skin is inherently sexy. She sat on her bed, eating her chicken burrito and lightheartedly told me to get on with it. "Yes ma'am" I chuckled as I undid my jeans. When I revealed my yellow and black selection, her eyes lit up.
"Ooooohhh no friggin way!" I asked what the excitement was about. She explained "I own that exact same pair haha and I'm literally wearing them today! how crazy is that?" I stuttered out something along the lines of "Really? You're k**ding right?" I hadn't even meant to challenge her claim, but without missing a beat she offered to 'show me proof'. She stood up on her bed and slid her summer dress up over her wide hips so I could clearly see (at eye level) that she was indeed wearing the same yellow briefs with the black trim. I could also see the smooth lightly tanned skin of her thighs, the delicate crease of her groin, the slight bulge of her mound, and the curvy swell of her hips. "What are the odds?" she marveled as she pulled her dress back down and went back to her burrito. I agreed it was pretty crazy (while I tried to mentally calm my confined penis). It had been a flashbomb of feminine sexuality and intimacy, and my little locked up dick definitely took notice. It was pretty uncomfortable but I sat down and tried to act normal. She sat and thought quietly for a moment and then pondered aloud "Hey. sooo you keep having to show me your underwear, and that just now was the only time you've seen mine. Maybe its more fair to you if I show you mine every time from now on? like, solidarity y'know?"
Jesus Christ, she was suggesting flashing her panties to me again tomorrow and the next day? I was already too horny for my own comfort, but for lack of any better response i blurted out "Sure okay."
"Cool! Yeah its more fair this way. I feel bad seeing you so vulnerable. This will be easier on my conscience haha." I was in a daze as we walked back to class. Trying to wrap my head around how her innocence, compassion, and loyalty were causing her to subject me to sexual torture - the torture of arousal without release. What a fucked up situation Rebecca put me in. I was frustrated with her, but I also would have done literally anything on earth to have her unlock me. I was frustrated but extremely turned on. I wasn't sure if I would cry or cum in my chastity device. Spent the night studying to try and keep my mind off of Catherine's ass in panties, my ass in panties, Rebecca's ass in general....
Thursday; just two more days of this hell and then I can see Rebecca and she will let me out of this cage and everything will be fine again. I was out of the more conservative pairs of underwear and now I was into the thongs and the pink stuff. I decided that feel was now more important to me than color, thus I put on a pink bikini thing with a thick black elastic waistband. They looked slutty, but I was not ready to wear a thong all day. Not yet at least. I daydreamed right through my morning classes. I still loved Rebecca but all this time spent with lovely Catherine and sexy panties was really testing my mental fortitude. Back at Catherine's place we had the house to ourselves once, but she suggested we hang out in her room again because its 'more chill'. I proceeded with what was now routine; I pulled my jeans down and exposed my slutty new underwear. She raised her eyebrows a bit and joked that I was a 'naughty girl'. That alone turned me on more than I can express. As promised, she stood up, peeled her black leggings down to mid thigh and pulled up her sweater so I could clearly see her red thong. she even did a spin so I got the full picture. My jaw dropped right open, which she obviously noticed.
"What? oh, have you never seen a thong before? I'm sure Rebecca must wear them all the time." My heart was pounding. Two days ago the mere mention of her panties put me on the edge, and she had just given me a full view of her round ass in a silky red thong. She softly walked over to me "Are you okay dude? You're breathing kinda heavy" She came right up face to face with me, both of our pants still down. I said I was fine, just a bit warm. I tried to compose myself while she looked me over checking for signs of illness or distress. Such a caring friend. Why the fuck were her pants still down? I couldn't help but notice that our genitals were less than a foot apart. If it weren't for this cage on my cock I would have bent her over right there and ruined her whole week. Instead I assured her that I was fine and pulled my pants up. I thanked her for doing this with me and making me feel so 'comfortable'. It was a little disingenuous because I was NOT comfortable, but what else can you say when your best female friend shows you her fucking thong out of 'solidarity'?
I was a zombie in my afternoon classes. I went home and took a very cold shower. Something I probably should have done every day this week. Fuck. Catherine is so fucking hot. How does a girl that small have an ass that big? Why is she so nice to me? Why isn't she weirded out by me wearing panties and being locked up? what did Rebecca tell her? These questions polluted my mind until I fell asleep. I dreamt that I was shrunk down to the size of a cat, and Rebecca and Catherine towered over me as my owners. They were dressed in latex lingerie and all 3 of us cuddled on a giant bed. My alarm went off before it could become a wet dream.... I woke up with a sense of determination. I just had to get through one more day. Then I would negotiate with Rebecca to get this plastic cage taken off me for good. I didn't even mind the panties, and I loved the excuse to hang out with Catherine more, but holy fuck this chastity thing will be the end of me.
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