From VERY early on in our relationship, Ana had been incredibly forward in letting me know I wasn’t what she considered boyfriend material. She explained, in excruciating detail, how she liked tall, strong, ruggedly handsome, alpha guys that were brimming over with confidence and swagger. She would go as far as showing me pictures of her dates and then bully and cajole me into admitting that compared to them, I was way too small, soft, and shy for Ana to ever consider romantically. After these confessions, Ana would wrap me in a tight embrace, give me little kissies on the lips, and tell me how even though I’m way too effeminate for her as a boyfriend, I do make for the sweetest little bestie a girl could ask for.
I should’ve run away. I should’ve have picked my shattered dignity up off the ground and done my best to find a real connection somewhere else. It’s just that I loved Ana SO much and her dismissive emasculating comments hit the central nerve of my erotic imagination harder and deeper than anything I had ever experienced before. She was so completely wired into my pleasure centers that the humiliation and embarrassment was never too much for me. If anything, as she went from ordering me to run errands for her, to doing all her household chores, to paying for beauty treatments and lingerie for her dates, to accepting that I was no longer allowed to date, to having to commit to being pussy free, to promising that I would only diddle myself with her expressed permission, and to accepting that I had to be home for my 8pm beta boy bedtime, I just kept on wanting more and more.
So when she came to me with the idea of us taking a six week girls’ trip I was terrified mostly because regardless of what this newest disgrace would entail, we both already knew I would inevitably say yes to it. She explained how we would be the best travel companions if I could make myself into her sweet, soft, sissy bestie. All I’d have to do is just let her accentuate how effeminate, sexlessly soft, and submissive I am by wearing pretty panties, locking my little pee pee up in tiny chastity cage, and letting her press a large butt plug into my tight booty hole every day of our six week vacation. As I started to recoil, Ana pursued, hands on my thighs, whispering in my ear that she knows all shy, soft, small boys like me have tried on panties before. Wouldn’t it be wonderful to drop all the pretense and have special intimate girly time with my bestie doing all the things that make me tremble and leak?
I melted. I didn’t know how Ana knew about my shameful secret desires but she did. My eroticized fears about being an inferior man and an effeminate pansy were formed over a lifetime of rejection, getting picked last, bullied, friendzoned, and humiliated. They were now being brought out into the open for the very first time, and instead of running from them like I had done before, I surrendered. Ana clapped her hands and giggled and suddenly my life became filled with things like a full body waxing, eye brow sculpting, facials, manicures, pedicures, and getting my hair styled into a pixie cut all to get ready for our trip.
After each appointment, Ana would take me to a local lingerie boutique to purchase a few panties and a couple of nighties that I would be wearing on our trip. It’s always such a humiliating affair. Every time Ana would force me to take my time with each piece of lingerie while she loudly interrogated me about why I always seemed to prefer very wispy delicates that were awash in bows and ruffles. I stuttered through my responses with a blush that could be interpreted as proclaiming to the world that I was a sissy who craved being as girly as possible.
Once as I had made my selections, and the whole boutique knew I was an effeminate panty boy, we would turn our attention to picking out a lingerie set that Ana could wear for date that night. The whole shameful production would repeat, this time with me bashfully holding my girly panties and nighties while commenting on what kind of lingerie I thought would turn a real man on. The final death swipe to whatever fragile grasp I still had on my masculinity would happen as I was paying for everything. I would stand there, blushing beyond belief and wishing I could just sink into the floor as Ana would always explain to the cashier that she would be taking all of our purchases home since she wanted my life in lingerie to start with our trip and little sissies can’t be trusted to not play with their panties.
The day of the trip, I arrived at Ana’s house as my first stop on the way to the airport. Just the thought that today is the day that I will finally be stepping into, pulling up, and then tucking myself into one of the girly panties that I have purchased would me more than enough to send me into a tizzy, but it is SO beyond that since Ana has forbidden me from diddling myself for the past two weeks. I’m absolutely trembling when Ana opens the door wearing only a black sheer peignoir and a matching bra and panty set. She explains, as she pulls into her home, that she figured that the best thing she could do to make me as comfortable as possible when I’m putting on my panties in front of her for the first time is to make it a fun girly panty party for the both of us. Before I can even really catch my breadth, I’m in Ana’s bedroom, with my small, soft, squishy body completely exposed, holding a lacy pink thong panty as Ana expectantly looks on.
Nothing looks that out of place as I slowly run the panty up my smooth slender legs and then create an adorable panty panty bump by tucking my small quivering pee pee into the girly thong. The tight embrace of the tiny panty is so uniquely feminine. The delicate material constrains my little clitty in the front while the thong divides my booty cheeks in the back. I’m overwhelmed by a swirling emotional hurricane of arousal and shame.
It’s in this moment of deep internal turmoil that Ana wheels out a pink suitcase and hands me a lacy pink bandeau bralette that perfectly matches my panties. She lets me know that I have a choice to make. I can take the suitcase that I packed and spend the next six weeks as a lonely secret sissy, wearing panties with a locked little softy and a plugged booty without any release OR, I could take the suitcase that she packed and spend the next six weeks as her very special twinky femboy. We could then play ALL the flirty girly games she knows I’ve fantasized about AND she’d let me work out a caged squirty squirt by humping a pillow and a vibe once a week.
With a predatory smile on her face, Ana lets me know that if I want to be her pretty panty princess, I’m going to have to put on my matching bralette just like I will be doing everyday for the next six weeks. Feeling the desperate throbbing of my little peen pull my thong even deeper into my booty cheeks, I don’t have the bandwidth to even pretend that I have to think this over as I clasp myself into the bralette. Ana is so overjoyed at how cute I look that she pulls me in for a deep hug that presses our bodies together and then lets it linger so we can feel the warm caress of each others’ soft skin. It’s during this sensual embrace, where hands gently explore and little kissies are shared that Ana has me tell her how happy I am to finally be pretty and pussy free.
With one last little squeeze, Ana lets me go and says it’s time for us to get dressed for the flight. Ana goes first and had selected a midi denim dress with a v deep neck that featured a double tie front and semi pleated skirt. And has me pull the dress up and over her voluptuous hips, and then because the v neck was so deep that it left the middle of her chest bare she asked me to remove her bra. When I faltered, she told me not too worry, a large part of my training to be a proper femboy will involve learning how to behave like a girlie bestie in intimate situations. All I have to remember for right now is that I’m not a real man and not act like one. My hands tremble, my breadth is short, and my panties feel especially tight as I unhook Ana’s bra, positioned her perfect breasts within her dress, and then tie her in. In response, she giggles, gives my panties a playful tug, and tells me how being a bashful little sissy seems to come so naturally for me.
Now it’s my turn. I literally gasp as Ana shows me the matching denim romper she expects me to wear. It has a halter top, a micro mini booty short bottom, and for the tiny amount that it does cover, its snatched fit will leave nothing to the imagination. As I beg and plead how I don’t want to be a panty boy anymore, Ana calmly folds her arms, cocks her head, and lets me know that even though she didn’t plan on spanking me before our trip even begins, she will if she has to. With tears in my eyes and heat in my panties, I step into the tiny romper and feel it encapsulate me in humiliating femininity.
The halter top shows off how effeminate my puny shoulders and arms really are. The micro mini bottom has my booty cheeks leaking out and leaves my entire legs completely exposed. However, it is the little peen bump in the front of my romper that makes me feel the most like an emasculated sissy. When Ana tenderly pinches my bump, I squirm and moan in delight as she tells me to enjoy this while it lasts because the moment we get to our hotel room my dinky winky will be starting its six week chastity sentence.
She wasn’t joking. The airports and flights were a blur. The whole time I kept my eyes down, listened to my heels click clacking on the linoleum, smelled my flowery perfume, felt the soft and tight embrace of my girly clothes, and held onto Ana’s hand like the shy, scared, shame filled, sissy that I am. The minute we get into our hotel room, Ana strips me down to my bralette and now VERY moist panties, has me ice my little peen until the swelling goes down and I feel numb, and then she very deftly puts the tiny pink chastity cage on me and locks it shut. As my weeny peeny warms back up, I’m mesmerized by the feeling of it impotently trying to grow, the sensation of being excited and electrically sensitive while staying small and soft is just beyond.
Ana now has me strip her down and we go take a shower together. With my little softy all locked up we can safely wash each other’s bodies, flirtatiously share kissies, and sensually press and rub our wet slippery bodies against one another. After we dry each other off, gently lotion each other up, and help one another into our delicates, Ana lets me know that it’s time for me to get plugged. I’m scared but I obediently get on the bed, bend over so my face is pressed into the mattress and my booty is up in the air, and feel Ana slowly peel my wispy little panties down my legs.
I feel one well lubed finger probe and then penetrate my tight little hole as I gasp and then moan. The combination of the second finger sliding in and rhythmically loosening me up while my little caged clitty stays small and soft has me surrendering all control to my inner sissy. There is nothing left but my girly desires to be filled when I reach back and spread my cheeks for the plug. There’s a touch, a push to the middle, a sucking in, and then a thud as the plug pushes out any lingering masculinity I have left. While I’m still trying to catch my breath, Ana daintily pulls my tight little thong panty snugly back into place.
Once I’ve recovered, Ana has me unpack our bags as she explains her vision for my behavior. As I’m hanging and putting away flirty feminine outfits, pretty lingerie, and scandalous little string bikinis, Ana tells me that she expects a girly girlfriend that always offers up obedience with a smile, a fun femboy wing sissy that helps her pick up real men, and an effeminate little twink that will stay pantied and plugged even when he gets sent to the room alone because she’s busy hooking up. Throbbing in erotic euphoria I surrender to all of Ana’s terms. She has me kiss her panties until she finishes to seal the deal.
After we dress each other in flirty little shorts and cami tops, we go out to take our first stroll through our exotic beach town. This is when Ana has me confess that I’m having fun. When she points out that this is just the first day out of six weeks where I’ll be locked in chastity, plugged, and wearing panties, I feel my little cage get tight with the implications. I already can’t even imagine returning back to my old life. When this is all over, who will I even be when it’s time to go back home? With a knowing little squeeze of my hand, Ana says she ready for us to go change into our tiny bikinis and hit the beach.
