Teased Denied and Sissified

I woke the next morning to a kiss on the cheek, "Hey sweetie, I'm heading into work early. I left a little note for you on your dresser. See you tonight at the mall." Opening my eyes I watched Ashley walk out of the bedroom and leave for work.

I wiped the sleep out of my eyes and realized I was still wearing her panties. Did last night really happen? I rolled out of bed and hopped in the shower. When I got to my dresser, I saw her note,

"Hey sweetie, This pair is a little big on me so I thought it might fit you better. Not the fanciest but should be enough to get you through the day. We'll get more tonight! See you at the mall after work! Love, Ashley"

I opened my dresser drawer to find that all my boxers were gone and, in its place, was a solitary pair of red cotton panties. I was a little puzzled. I had assumed that the sissy play would stay in the bedroom but Ashley appeared to have a different idea. I shot her a text asking where my boxers were, but, with no other options, I slid on the panties tucking my soft cock down into them. I turned and admired my ass in the mirror...I guess they did hug it well I thought to myself. I finished getting dressed and went off to work. That morning I got a response from Ashley that simply read "You don't need them anymore, remember! If we're going to do this we're going to do it my way and do it right. Let me know when you leave work and I'll meet you at the mall."

The workday was long and I was reminded of Ashley every time I went to the bathroom and saw the panties. I avoided using the urinal for fear of someone seeing them. Sliding them up still got me a little turned on but I'd distract the mind to avoid a sexual harassment lawsuit at work. I texted Ashley to let her know I was leaving and she suggested we meet in front of one of the department stores. When I arrived she was waiting there with a smile, "How's my sweet sissy today? How was your first full day in panties?"

"It was good but I had to sit down when I went to the bathroom. I didn't want anyone to see. I didn't think I'd be wearing them all day. I thought we'd just be doing this in the bedroom."

"I told you that if we're going to do this, we're going to do this the right way. It's all or nothing. I didn't think I'd come home yesterday to my boyfriend wearing panties. Now c'mon and let's have some fun with this!"

"Ok, I'm sorry...I agreed to this and you're right!" I said with a smile, "just try to be a little discreet in the store. I don't really want them knowing this stuff is for more, ya know."

"Oh, stop. No one is going to know and who cares if they do!"

We walked into the mall and she directed us to the lingerie section in the department store.

"They have some stuff here if you want. It's a little cheaper but not quite as sexy as a Victoria's Secret. Do you have a preference?"

I was uncomfortable having this conversation with other people around us, "Ummm, I don't care. Let's just get something and get out of here."

"Stop being like this," she reached for my hand "we're doing this together and no one is paying attention to you. Now...do you want to check Victoria's Secret? They probably have a bigger selection."

"Ok...sorry...yes, that sounds good."

Off we went through the mall, still holding hands and talking about the work day. All I could think about was the awkwardness I would feel inside Victoria's Secret.

"How many are we buying today?"

"How many what? Panties? Well, I figure you probably need about 10 pair so you're not constantly washing them, then you'll also need some bras and maybe some other stuff so you feel extra sexy in the bedroom. I figure I deserve a thing or two since I'm doing this with you too." she said smiling and looking up at me "it's not like you don't have the money."

Ten? Bras? This was starting to add up but I had to admit that I was a little excited. The thought of doing it a little more often with a willing participant turned me on. We walked into the store and I was a little overwhelmed with all the options. Fortunately, Ashley knew her way around.

She looked at me "I was thinking a few lacy pair, since you seem to like those, and these french cut might look good on that ass of yours.. Maybe a thong or two but I'm not sure how they'll fit you down there...you might...um...spill out. Have you ever tried one?"

Feeling a little awkward discussing it in the the store, I said softly "Um, ya, it's harder to wear one but we could try a couple."

"Ok cool...what colors? I was thinking some nice pastels for you and maybe a hot pink!" she said smiling.

I smiled, blushing a little, "Ya, those sound good."

"Sizing will be tricky. I'm thinking medium but you might need a large...oh miss, can you help me a second?"

I was horrified. Asking for help?! I stood there hoping she wouldn't notice my face blushing.

"Yes, what I can I do for you?"

"I need to buy some panties, but they aren't for me. My...friend...is actually probably about his size. Do you think a medium would work?"

Smiling and looking at both of us "Ya, I think a medium would be good. If it won't embarrass him too much you can hold them up to him too" she chuckled.

"Oh, thanks! Probably a 36 for a bra, right?"

"For someone his size, probably a 36 or maybe a 38. If you wouldn't be too uncomfortable I can measure you but you'll still have to guess on the cups.!"

My face went beet red, "They aren't for me!" I blurted out.

Ashley laughed, "why don't you just measure him to be safe"

I lifted up my arms and she measured across my chest, "Looks like a 36 would probably work, but it could be snug. Do you have an idea of what her cup size might be?"

"Hmmm....pretty small...probably an A but could do a B if you don't have it in stock." Ashley replied while smiling at my discomfort with the situation.

"Well, let me know if you need any help in picking stuff out" and she walked to help someone else.

My face was clearly red now, but at least it was over. I took a deep breath and looked at Ashley, "I thought you said you'd be discrete."

"Oh stop...we needed sizing anyway. You didn't want to have to come back and return stuff. I said it was for a friend. If anything you made it worse with your red face and tone. Now come on...let's find something sexy little sissy." she said with a smile.

Ashley was pretty good at finding stuff and would just ask my opinion. I generally just agreed with whatever she found but was growing more comfortable and would occasionally suggest colors. Each item she would hand to me to hold on to...I lost count of what we had. When we were wrapping up she approached a mannequin with stockings, garters and bustier.

"We should get two of these...one for me and one for you!"

She looked for sizes and selected hers in black and turned "something lighter colored for you...pink?"

"Sure, that works. We have a lot of stuff...surely we don't need much more."

"Hmmm...well, might need a few more bras because I worry those will show through your shirt at work." she whispered at the end.

"Show through my shirt?"

"Well, ya, I wear one all day...so are you. When are you going to understand this isn't a one time or every now and then thing. If I'm going to have a sissy for a boyfriend I want you to immerse yourself as much as possible. Now let's look for something over here that won't stick out as much."

"Why don't we leave this at the counter and they can start ringing it up. They have some cute PINK loungewear I want for around the house and you could use a few things too."

"Loungewear too? How much are we going to spend? I already have gym shorts to wear around the house."

"Stop whining. I told you this wasn't going to be cheap so open your wallet and appreciate that I'm doing this with you and obviously those gym shorts aren't going to cut it anymore. We'll just get you a couple pair of shorts and tank tops. They might be snug but we'll get you on a diet and working on your figure."

Diet? I thought. I started to question if this was going too far. I thought I would hold on to at least some of my manliness.

Ashley grabbed two pair of pink shorts and a couple for herself. "These will be cute for you!!" she whispered then grabbed a couple tank tops. "Perfect...let's check out."

The total came to a mind boggling $450. I couldn't get over how expensive it was, but Ashley had a smile as we walked out. Shopping with her had made me both turned on and little apprehensive. I didn't realize how far she wanted to take it

"I can't wait to get home so you can try some of this stuff on! Maybe I'll put on something sexy for you too" she said.

"Me too," I smiled "it's a real turn on that you're so into this."

She gave me a peck and we got in our cars to head home. My heart was racing as I drove home. As painful as the shopping was, I excited to try on my new stuff. My cock was already starting to get hard thinking about it.

Ashley beat me home and I found her in our bedroom unloading stuff into my dresser. "Here," she said "Start by trying this on."

She handed me a satiny pair of hot pink panties with lace trim and a matching bra. I disrobed and slid on the panties while she helped me with the bra in back "you're going to have to learn to put this on yourself. Now...you're not that hard right now. Can you tuck yourself in between your legs? It would be nice if there wasn't a bulge." I did as I was told though I knew I'd be popping up again once I got hard.

"Mmmmm," she said, "there's my sissy" she said as she stood behind me, rubbing my ass in the panties. "You get comfortable on the bed while I put on something we got today." She disappeared into the bathroom.

She emerged wearing a sexy black lacy bra and thong set complete with stockings and garters.

"Wow" I said "you look so hot right now."

"Mmmm...good" she said smiling "that's the point. Now let's put a little of this on your lips to take things a further little sissy."

She reached out with some pink lipstick and put it on my lips. "Good, now come here"

She leaned forward and we began making out, my hands on her body and her hands cupping my bra and reaching in to pinch my nipples.

"I think you need more practice with your tongue" she said as she gently pushed me on my back and began straddling my face. She moved her panties to the side and I buried my face between her legs. Her thighs against my cheeks as she moved her hands through my hair, moaning, "Mmmmm, nice and slow." I could taste her getting wet as she moved her hips against my face a bit, moaning louder as I watched her begin to squeeze her breasts over her bra, "Let me turn around and give you a little attention."

She turned around and leaned forward on her knees, lowering her pussy to my face, "Keep going" she said as she began rubbing my cock through my panties, noting some precum "Hmmm...looks like you're getting wet too." I continued going to work on her pussy when she asked me to pull my legs up a bit as she slid her hand into my panties.

"I think you'll like this," she said with a smile, "and don't act like you haven't done it before," she said as I felt her finger rub the outside of my asshole.

She was right and I couldn't deny it, "How'd you know? I just tried it once..."

"You're wearing panties, so of course you've fingered your ass and I doubt it was just once. Now just relax and don't stop paying attention to my needs." She moistened her finger and slid it back into my panties and against my hole, gently working it in. I moaned a bit as her slender finger went in. "We'll get some lube for next time but I thought you'd like a little tease," she said as she rubbed my balls with her other hand, sliding it in a bit deeper.

With my cock in her face I kept wondering if she would take it out and go down on me. I was so turned on and aching. I finally asked, "You've got me so hard and turned on. You could slide me out of the panties if you want to play with my cock a little while you're down there."

She took her hand off my balls and pushed her pussy in my face, "I told you that was staying in your panties where it belongs. You need to understand that while you're wearing panties that your little dick gets less attention. You need to learn how to please and learn new ways to receive pleasure." She slid her finger out of my ass, sitting up and moving to the night stand. "You've got me pretty worked up," she said as she got her dildo out and handed it to me. She got on her hands and knees, "Take me from behind with it. It's a position we never got to do much since you slip out but I know it feels so good." Another reminder of my lack of size, but I took it in stride getting behind her perfect little ass and rubbing the head against her pussy. She looked back at me, arching her back and pointing her ass in the air, "Mmmmm...fuck me hard."

I loved the dirty talk but couldn't help but wish it was directed at me and not the dildo. That said, I loved watching her and helping her get off. I truly enjoyed giving her pleasure. I slid the dildo in slowly, "I said hard sissy!" she barked, "Make it hurt." Words I had never heard, or thought I would hear, from her only turned me on more as I began aggressively fucking her with the dildo, deep, long strokes. "Oh goooooddd, so good," she moaned, "Get your face in my ass and lick it."

I hesitated. This was something I hadn't heard her ask for before "Oooohhh, just do it now!" Her orders turned me on so much, I buried my face between her cheeks, rolling my tongue around her hole. "Oh, god, don't stop...fuck me harder." My arm was getting tired as I worked harder on her hole, getting it wet. "Slide your finger in," she beckoned "I want your finger in my ass too" she whined, moaning louder as I slid my moist finger in her ass. I couldn't believe this girl was such a freak in bed as we typically only did missionary in the past. "Oh god, don't stop, I'm going to cum" as she moaned and screamed, her body tensing and trembling before relaxing. I slowly pulled my finger and the dildo out, rubbing her ass a bit before moving up towards her.

"Oh my god. That was so good. I haven't been fucked like that in a while!" she said as she leaned in to kiss me hard. "It was so good. You're the best. You want to clean my dildo off again like last time?"

I couldn't believe what I just witnessed. I was a little taken aback, "I've never seen you in the bedroom like this before. It's really hot."

"I guess there is a side of me you haven't seen before and maybe I'm learning about myself a little too."

"I wish we could have done some of this stuff before without the panties. I'd love to try anal."

"It's a little late for that now...you're already in panties. Also, you've never really been, like, a manly man, for me to think you'd be able to make me cum like that or be able to fuck me hard in my ass." I was a little perplexed and let down. I think she could tell. "Oh sweetie...it's not your fault. We're doing it together now and that's what counts! Now show me how you clean off the dildo, just like last time." I opened my mouth and she took the dildo, sliding it in as I wrapped my lips around it, "There you go...good sissy."

She removed the dildo from my mouth and went on, "Now I know you didn't get to cum today, but you need to learn a little discipline. Girls don't always cum when they have sex and I'm willing to bet you haven't made many girls cum with your cock in the past. Therefore you need to learn you're not going to cum very often. I promise you that you'll get to cum at some point, but, in the meantime, I don't want you playing with yourself. Hands off. I'll decide when you're ready."

I wasn't sure how long I could make it especially considering how turned on I still was. My balls were aching. Would she really know even if I did?

"Ok, I'll do my best."

"No, not your best. Tell me you won't do it. That's for me to decide now, not you. It stays in your panties, remember."

"Yes, sorry, I won't."

"Ok good! Throw on your new pink shorts and top and let's cuddle on the couch. You wore me out!"