The flea market was just like any other. I walked around looking at all the trinkets and clothes, picking up a few things here and there. I’m normally too scared to do this, but I was feeling abnormally brave (and the flea market was in another county) so I decided to buy a dress or two along with the usual things I look for. I found this one booth that was selling the frilliest, girliest dresses I’ve ever seen, and they looked like they could fit me. After passing it 3 or 4 times, I finally mustered up the courage to take a look when the girl running the booth was looking the other way.
She was tall, young, very pretty, wearing all black, and had short blonde hair styled like a boy’s. I couldn’t help myself from checking her out a bit as she had a really big butt and pretty strong arms too. As she turned around I quickly went back to looking at the dresses she was selling, which probably didn’t look much better. I could sense her staring at me but I just blushed and meekly looked through the rack. The dresses were all so adorable; I wanted to buy them all! There was a little performance tutu with a starchy skirt, a maids outfit with a cute little apron attached, a poofy prom dress with sparkles, I was in girly heaven!
Finally, I saw a dress that just called my name. It was a sweet little party dress with a white peter pan collar and big poofy sleeves with lace underneath, the skirt was short but had so many ruffles that it poofed out more than a meter at every side. The entire dress looked like it was doused in glitter so it was super sparkly and to top it all off, right on the front of the dress was a pink heart design that said “Cutie Pie” inside it.
My heart started beating faster and faster as stared at that heart and those frills. I completely forgot about my surroundings; this dress was my entire world. I imagined the pretty frills tickling my thighs as pranced around in it, curtseying to ladies as I served them drinks and blushing when they lifted up my skirt to see my panties. I was in a total trance until suddenly I was ripped out of my daydream and brought crashing back to reality by the words of a woman saying,
“Pretty isn’t it?”
I gasped in shock and turned around to see the shop owner staring down at me with a smirk.
“Would you like to try it on?” she said.
I panicked and came up with a quick cover.
“Oh n-n-no thank you! hehe! I’m looking for a dress for my d-d-daughter…” I had to crane my neck to look up to her. I prayed she’d buy my story. I’m 24 but I ‘m so short and slender that I look like I’m 14, so I don’t exactly look like a dad!
“How old is your daughter? She must be kind of big if you’re looking at getting her that.” She asked, raising an eyebrow.
“A-Are you calling my daughter fat?” I said with all the courage in my body (which wasn’t much). She stared at me for a bit, then started laughing.
“Hahahahah relax lil’ dude! I’m just teasing you. I’ll wrap this one up for you.”
I can’t believe that worked. She took the dress off the hook and brought it over to her table (giving me one more look at her cute butt). She folded it neatly and put it in a plastic bag. She said it was $20, but as I got out my wallet she asked me something that took me aback.
“Your daughter, does she have bedwetting problems by chance?”
“Why do you ask?” I responded, a little confused.
“Well, I’ve been trying to sell these diapers all day, but I haven’t had any takers. I made them myself in this super cute design! And they’re really soft and comfy and very absorbent so they’d be perfect for a bigger little girl. If you were interested I’d sell a pack of 20 to you for… say $5?”
She pulled out a sample to let me feel the diaper. I had known about sissy babies since I started cross-dressing but never considered wearing a diaper myself. The fabric was super fleecy and felt really nice though and I thought It’d at least be something nice to masturbate into, so I said okay, and gave her $25.
“Oh dude you’re so awesome! Thanks for taking these off my hands! You’re daughter’s gonna love these diapers. And if she gives you trouble tell her their made with magic! That always works with my little cousin. I’m Amy by the way!”
“Oh haha sounds good thanks! I’m Ben.”
“Nice to meet you Ben! I’m putting my card in the bag in case you ever need more dresses or diapers! Have a great day!”
“Thanks same to you!” I said and rushed to my car. I felt on top of the world and was so excited to get home and try on this dress! I sped all the way back home, rushed up the stairs to my floor and bolted down the hall to my apartment. Once inside, I saw my roommate Kelly and her friend Lauren playing video games.
“Hey Ben! How was the flea market? Wanna play with us?” Kelly asked.
“Yea Ben! Come play with us so I can beat your ass!” Lauren yelled.
“Hey Kelly! Hey Lauren! The flea market was awesome! I got a lot of great stuff!” hoping they wouldn’t notice the pink bag holding my dress and diapers. “But I think I’ll pass on the games for now. I think I’m just gonna take a nap actually. I’m pretty tired from the whole thing.”
“Okay! We’ll probably still be here later if you wanna hangout when you wake up.” Kelly said with a friendly smile.
“Sleep tight lil baby!” Lauren yelled causing them both to giggle. I blushed and let out a little laugh. If only they knew!
When I got into my room, I quickly locked the door behind me and laid the pretty dress on my bed next to my stuffed toy bunny (in case you didn’t already know I was a sissy). I knew I couldn’t just put it on, that would be disrespecting something so pretty. I had to go the whole 9 yards for this special occasion. So I went into my closet and grabbed a small suitcase out from behind my laundry hamper. I opened it up and there was my collection of pretty clothes. I decided I should first put on some lingerie, so I pulled on some lacey pink panties and snapped on my matching bra. Once that lace touched my penis I immediately started to get hard, so I decided to put my nipple-stimulating suction cups on and stuff my bra with 2 of my other pairs of panties. The suction on my nipples felt so good but I decided not to touch myself until I was fully dressed.
I rolled my pair of pink and white striped thigh-high stockings up my hairless legs and slipped my feet into a pair of white mary-janes. My hair was short but I put on my long blonde wig that was styled in pigtails with pink ribbons. I had looked up how to do my makeup to look like a doll in the past and I thought that would be perfect now, so I started to put the soft foundation all over my face making me look a little paler. Then I used the pencil to put dark pink eyeliner on and a soft pink shadow after. I put the bright pink lipstick only on the center of my lips so it looked like I was constantly making a kissy face, and I finished the look by putting two big circles of pink blush on my cheeks.
Finally I was ready to put on my new pretty dress and it was perfect timing because I my cock was throbbing. Just as I was about to slip into my frilly dream dress, my eyes glanced over at the pack of diapers. I remembered how soft they felt and how great that would feel on my cock. So in my horny state I pulled down my panties, got my remote controlled vibrating buttplug out, lubed it up and worked it in up ass (I decided if I‘m gonna be a sissy diaper slut I better do it right) and then I opened the pack and unfolded one of the soft pink diapers.
As I sat down on it I was overcome with pleasure from how soft it felt. I rubbed my now-plugged ass on it a little and let out a soft moan from how good it felt. I folded it over my hard cock and undid the tape to fasten it on me as tight as it possibly could be. This one was a lot bulkier than the sample Amy showed me, but that just made it better. My legs were forced to spread apart a little bit and it puffed out a lot on my front and back. She must have perfumed them too because this beautiful, intoxicating scent of flowers and cotton candy filled my nostrils. Just a whiff made made me feel weak in the knees. As I fumbled to stand up, I realized the diaper made me have to waddle a little bit, which made me blush through my makeup, but every step I took the wonderful fabric would graze against my cock, almost bringing me to a climax each time.
I was finally ready to finish my outfit! I slowly and carefully waddled over to the dress, being careful not to cum until I was completely dressed up. I stepped into it and pulled it up my body, having to put in a little more effort to get it over my diapers, slipped my arms through the puffy sleeves and zipped up the back. It fit me perfectly, just tight enough around my chest to accentuate my stuffed bra, giving me the look of developing breasts. As I smoothed out the ruffled skirt, I realized there was no way fro me to comfortably rest my arms without disrupting the frilliness, so I had to keep my elbows and wrists upturned the entire time, only giving me a girlier look. Also the skirt was so short that it barely covered my thick diapers but I kind of loved that.
I didn’t have a mirror in my room, but I really wanted to see what I looked like. So I opened my phone’s camera, propped it up on my desk and started taking a video. I waddled into frame and started to twirl around showing every side of my outfit to the camera. I blew a few kisses, did a little dance and struck some sissy poses. As I lifted up my skirt to show off my thick puffy diaper, I got a very naughty idea.
I grabbed the wireless remote for my plug and turned it on the highest setting. I started moaning and whimpering with pleasure and the toy buzzed in my ass. Not wanting to alert Kelly and Lauren, I started sucking my thumb to muffle the moans. I was getting so hot I was ready to bust but I desperately wanted to hump something so I grabbed my stuffed bunny and pressed it hard against my squishy soft diaper and started rubbing back and forth. I barely lasted another minute before my knees buckled and my entire body shivered with pleasure, filling my thick soft diaper with what felt like a gallon of my warm, sticky cum.
The sweet smell from the diapers filled the room and a strong feeling of sleepy bliss washed all over me after my orgasm, I wanted to get my phone to see the video but I just felt so weak all I could do was curl up on my bed and pass out, still sucking my thumb and snuggling my stuffed bunny.
“That was the last thing I remember before waking up in that cell, officer.”