7 comments/ 82094 views/ 46 favorites Teased, Denied and Sissified Ch. 01 By: subbieman My girlfriend and I had been dating for nearly nine months when we decided to move in together. Her lease was expiring so it made sense as we had grown closer and she really seemed like "the one." We got along great and I loved her, but, to be honest, our sex lives had recently been lagging. I hoped that moving in together might rejuvenate it, but, based on the first month, that didn't seem to be the case. We were down to having sex just about once a month and she just seemed to go through the motions and never went down on me. We had talked about trying to spice things up, but nothing had come of it. Ashley was petite and, in my opinion, sexy. She was only about 5'3", with a small round ass, flat stomach, perky little tits and dark brown hair and eyes to go with a light tan/olive skin. She stayed in shape with running and flexible with yoga and, despite her small stature, had a little firecracker personality at times; she was outgoing and fun. There was one thing that I had considered bringing up to her, but never could muster the courage to mention: I enjoyed sliding on a pair of panties and a bra every so often. I'm not sure why I enjoyed it so much. I had been doing it since I was in my teens and when I was single had even taken it upon myself to order some of my own. It was such a turn on and it made me really express my submissive side. Perhaps, secretly, I wanted to get caught rummaging through her sexy underwear but deep down I knew it could be catastrophic to the relationship and probably better to be brought up rather than discovered. It was something I enjoyed, but wasn't so important that I'd throw away a great relationship over it. One day, however, I was left without a choice. I found myself home alone and a bit horny so I ventured into her dresser and pulled out some panties and a bra; matching of course. I stripped down my clothes and slide the bra over my arms. My girlfriend is smaller than I am so I couldn't close it in the back but still enjoyed wearing it; running my hands over the small cups. I reached down and pulled up a pair of her lacy panties. She had the sexiest bras/panties/lingerie and while these were quite snug I squeezed into them. Not being the most well hung man at about 4 inches, my hard cock barely poked out the top. I ran my hand over the lace on my cock and turned to admire my ass in the mirror when I found my girlfriend standing there. My stomach sank with fear. "What are you doing?!" "Nothing...sorry, sorry...I'll take them off. I just liked them. I don't know...sorry!" as I slipped the bra off my arms. "Wait. Do you do this a lot?! I don't understand. Why are you wearing my panties? Does it get you off? Not that they fit all that well anyway." I began to slide them off. "Wait," she said grinning, "I didn't tell you to take them off. I asked if you liked it." I stopped. Taken aback, "well, yea, I guess I just like the way feel on me," I stammered. She took a step forward, kissing me hard, grabbing my ass and pushing me toward the bed. Welcoming any physical interaction with her, I let her take the lead and went to the bed. She climbed on top of me, pulling her shirt off and revealing a sexy lacy black bra. Grinding her crotch on mine, "you probably wish you were wearing this bra, don't you?" She eased up for a moment to take off her shorts and panties, "you like these?" Then noticing my cock had begun to ooze a bit, "you mess my panties? You can keep those now." as she climbed back on me. I couldn't believe what was coming out of her mouth or what she was doing. I was in shock but didn't want to interrupt things as I was excited at the prospect I might finally get laid. With my hands on her hips, she paused to pull my panties down a bit to reveal my cock, "you want to cum little sissy? That is what they call guys who wear panties, right? Sissies?" I hesitated, a little dumbfounded but also enormously turned on by them. I wondered if she could notice how turned on I was. "Uh, ya, I guess so." I slid in and her wet pussy felt amazing as she grinded her hips. Maybe this was the sort of shot in the arm our relationship needed. Something crazy to happen. The passion was unreal She looked down at me, "I'm going to let that little thing cum in me, but I want you to go down on me after and make sure I get off until my heart is content." I had never heard her call me 'little' but I chose to ignore it for now. Perhaps I misheard her. My cock was throbbing. Then it hit me, "but my cum will be inside you." "Yes, I know. That shouldn't stop you from pleasing me. If you're going to wear panties then you should play the whole part." I didn't have much time to ponder it. Truth is, I had tasted my cum several times before just out of curiosity. It wasn't so much a repulsive taste as the principal of it; that I would be slurping down my own mess. She girded down on me, squeezing my cock a bit "How bad to do you want it?" she said with a little grin. "Ok...I want you so bad right now I'm going to explode." She picked up the pace and within moments I exploded letting out a big moan. "Oh my god...that was amazing." I said smiling "that was so hot. You had me so turned on." "Mmmm, good. Now pull your panties up because it's your turn to help me get off." I felt her tighten around my cock as she slid off and she motioned for me to slide under her. "Now come here sissy, taste your mess and show me how you're going to get me off." "You don't have to keep calling me sissy," I said, sort of thinking that part was over. "Shhhhh...you can't talk and lick my pussy at the same time. Now open up," she said as she lowered herself on my mouth. I wasn't quite ready for the volume that came out of her pussy. I tried to pull my head back a bit but with one hand on my head she grinded her pussy in my mouth. "Oh no, sissy, I want you to swallow it all and lick my clit until I cum." I swallowed the full load, feeling it run down my throat while she looked down at me grinning. I went to work with her grinding her clit on my tongue. I had never found her so wet as I did then, with her hands firmly on my head pressing her pussy into my face. "Don't stop, don't stop" she panted while squeezing her tits under her bra. I kept at it. "Oooooohhhh...gooooodddd!" she moaned while clenching her legs on my head and cumming. I worked more slowly as she looked down at me. "Mmmmm...very good, but I'm still horny!" she said with a grin. "Since I learned one of your secrets, you might as well learn one of mine." She got up and walked to the closet. I glanced down to notice that I was already hard again, my cock poking out of her pink panties. I laid there admiring her cute ass as she reached up and grabbed a shoe box. She turned around and approached the bed with it "I want you to help me cum again" she said as she removed the lid to reveal a vibrator and a realistic looking dildo. "Where did those come from?" "We can talk about that later. Right now I want you to use this dildo on me while I use the vibrator on my clit. That dildo makes me cum so hard." She handed me the dildo with a grin. "It's...big." I sad "It's not THAT big. It's just a bit above average and I've had bigger than that before anyway. Now c'mon and make me cum." "Well, I'm hard again if you want to go at it" "No," she said with a big smile, "I want that! Wait until you see me cum...you'll be jealous," giggling a bit. She laid back and put the vibrator on her clit while I gave the dildo a look. It wasn't a monster, but was certainly bigger than me. Guessing just over six inches and thick, but not absurd. Turned on by the idea of getting her off with it, and turning it up a notch in the bedroom, I put the tip against her wet pussy. "Mmmm...that's it...slide it in" I began sliding it in, pulling it out before going all the way in and then gently pushing it back in, watching her small lips hug and wrap around it's girth. "Mmmm...keep going" she moaned. I pushed it in a bit further and began fucking her with it. "All the way sissy...I want to feel it" she moaned as she rocked her hips back to welcome it. I followed orders and slid it all the way in. She was a small girl so I was a bit surprised I didn't meet any resistance. I began to slide it in and out gently as she moaned. "Mmmmm...that's it...a little faster. I want to be fucked hard." I picked up the pace as her hips started rocking and she continued to moan and egg me on to keep it up. I was really getting turned on and reached down with my other hand to stroke my cock in the panties when she stopped me with her hand on my wrist, "just leave that in your panties sissy and focus on me...c'mon...fuck me harder!" I pulled my hand away from my cock and worked the dildo harder as she moaned harder and louder. It wasn't long before I watched her have an orgasam like I had never seen her have before. She screamed while clutching the sheets "ahhhhhhhhh!" I slowed the pace as she shut off her virbator and pulled my hand away. "Oh my god that was amazing. Look how wet that dildo is." It was practically dripping. "You should give it a lick to know what I taste like after I cum." I just kind of looked at her not sure if she really wanted me to lick the dildo or what. "C'mon sissy...you're already wearing panties. If you're going to wear my panties then I want to see you clean that dildo off with your mouth." She reached for the dildo and held it out. "Open your mouth for me." Still under her spell I followed orders and opened up. She slid the dildo in my mouth "Mmmmm...there we go...wrap your lips around it," sliding it back and forth a bit, "hehe...you're a natural." She tasted amazing even if it meant I had to suck a dildo for it. She did seem to enjoy it though and I was just happy to see our sex life potentially perk up. She pulled it out of my mouth and set it on the nightstand, "Come lay here and let's talk." "I think it's clear there are issues in the bedroom, but I think today really helped us address them. I love you and want to explore this sissy side of you. Also, now that you've probably realized that I get more enjoyment out of my toys than your cock, I think we should use them more and keep your little friend in those panties...especially while we explore this sissy side of you. Let's give it about six weeks. I'm really excited to explore this. Deep down I guess I'm not totally surprised to find you in panties since you have always been a little submissive." I was a speechless. While I had always found putting on panties and dressing up to be a real turn on, I had still envisioned being the man about the house. I feared this might put me in an awkward position. I also didn't want to lose her. I was truly in love. "Well, I'm a little surprised you're so into this. Are you sure it's a path you want to explore? I'm willing to do it for you and to save our sex life...Frankly I thought moving in together would have helped but if this is what we need then I'm willing to follow your lead. I'm a little apprehensive though...it sounds like you don't want to have sex." "Oh...we'll spend plenty of time in the bedroom finding new ways to get each other off. Couples need to be adventurous to keep their sex lives from getting dull. That said, I do expect some extra attention and understanding given the effort I'm putting in for you; most girls would have freaked out and walked out on you by now. If we're going to do this, you're going to have to trust me. It may not always sound like something you want but what you want isn't always the most important. You have to realize that my needs are important and trust that I'm doing what's best for our relationship. Do I have your commitment to follow through on this?" "I guess that's true about any other girl. I love you and I trust you." "Good," she leaned forward and gave me a peck on the lips "I'm excited! We'll go shopping together tomorrow!" "Shopping?" "Ya! You need your own bras and panties now. Some that fit and maybe a thing or two for me too!!" Teased, Denied and Sissified Ch. 02 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!" Teased, Denied and Sissified Ch. 03 About a week passed since Ashley discovered my little panty fetish which was followed by our shopping trip. I was wearing panties daily and had found a couple bras that didn't show through my dress shirt at work. I started to grow quite used to, and fond of, wearing bra and panties everyday and mentioned as much to Ashley. "I thought you would," she smiled wryly "We should probably get you more." It had reinvigorated our sex lives which largely consisted of Ashley straddling my face and fucking herself with her dildo. She would turn me on so much, but was adamant about keeping my cock in my panties. Blue balls were becoming common and I was getting to a point that I couldn't take it much longer. This became worse when I received a text from Ashley at work: "Kitty needs some licks," it read and was accompanied with a picture up her skirt. I could make out the top of her new stockings and garters and she wasn't wearing any panties. My cock immediately began getting hard. I couldn't take it any longer. I ducked out of work a little early, beating Ashley home. I stripped down and pulled my cock out of the top of my purple panties. Figuring I would just toss off in the toilet I stood there rubbing. Within minutes I had the release I desperately needed. I immediately felt guilty, thinking of Ashley and the displeasure she would feel. With her in mind, I wiped the end of my cock with my finger and sucked it off. I figured if she was there, she'd want me to taste it. I flushed the toilet, changed clothes and headed to the couch when I heard Ashley walk in the door. "Hey honey! How was your day? That pic you sent was unreal." I said smiling "Hmmmm, I thought you'd like that. Figured my little sissy needed some inspiration to get through the day. Now come in the bedroom and follow through on kitty's request." I followed her in the bedroom as she headed into the master bathroom to pee. "Ewww...what is this? Is this...cum?! What the fuck?! Did you jerk off?" Holy shit. How did she know? I approached the bathroom door to find her squatting and pointing at a large drop of cum on the toilet seat. Apparently she sat in it. My carelessness cost me. "Oh honey, I'm sorry, I'm sorry, it's just...it has been so long and I haven't gotten off and that pic and you turn me on so much. I'm so sorry. I won't do it again." "You promised! I told you that I would determine when you were ready. I actually thought today might be a good day for you to get a little release but you fucked that up." She walked toward me, skirt on the ground, blouse still on, "I'm so disappointed in you, but I guess I shouldn't be surprised that you can't control yourself. I actually have something that will help but, before we get to it, I want you to take the next step in your little journey and get rid of all that icky man hair." "Get rid of my man hair?" I protested, "You really think I need to shave all my hair off? What if I wear shorts? It's still kind of warm here. I should be able to leave some of my hair on...I'm still a man." "Seriously?" furrowing her brow, "You just jerked off without my permission. And now, after all I've done and my understanding, you're going to balk at shaving? It will grow back and, furthermore, you promised you'd follow my lead here. Don't forget that those stockings you got last week will feel that much better on your smooth shaved legs. I want it all off - underarms, chest, legs, but you can leave a little above above your little cock. Just make sure it's trimmed nice and short. Now march your little sissy ass in the bathroom and get to it." she said with a smile. Not feeling like I had much choice, I drew a bath and stripped down. I'm not particularly hairy to begin with, but I still made use of all the razors available. I had to call her in for help to get the last bits under my balls and between my legs and she happily obliged. As I dried off she told me to stay put and she'd be right back. The towel felt wonderful on my smooth skin and I was looking forward to putting on the stockings later. My skin seemed so much more sensitive. She came back with a smile on her face and a small box. "Sweetie," she began "I had a feeling you might not be able to control yourself and would violate my trust, so I proactively got something to ensure it won't happen again. Now - I want to remind you that I have your and our best interests in mind. My goal is to keep us together and I feel like this is the best solution. Also, remember, that I said we would explore this fetish of yours for about six weeks and, if things aren't going as well as we had hoped, then we can talk about making changes. That will include this." She began opening the box and continued, "I'd like you to start wearing this full time. It's a chastity device and I got one that I think should still fit comfortably in your panties. Before you say anything, remember, we'll just try it out for the next several weeks and I'll let you out occasionally. We'll make sure it's comfortable enough for you to wear all day and night. Trust me...this is for us." Taking in all that she said, it was difficult to argue. I had violated her trust and I wanted to keep her happy. While I enjoyed the freedom of jerking off whenever I wanted, I had to trust that she was going to let me out from time to time to get off. She said she would let me out and I had to believe her. Plus, if it wasn't working out in five weeks then I could tell her I wanted it off. "If you really think it's necessary, I guess I can try it out." "I do think it's necessary and, once it's on, remember, I hold the key. If you're feeling pain and discomfort we can adjust it, but it's my rules. I actually think you'll find you enjoy giving up control of your cock to me and want to leave it on in the future. In some ways, it could end up being very liberating." "Um, maybe, but let's just try it for now." She smiled up at me as she pulled it out of the box, "Good! Now, there is this ring here. It says it should fit as snug as possible without it being uncomfortable. Try this one." I took it from her hand. "This one seems a little big, maybe a different one?" She pulled another out "This is the second to smallest. Try this one." "This one seems to work." I said as I found myself getting slightly turned on. Ashley took notice. "Whoa...looks like you might like this after all.." she said smiling "Well, I don't know...maybe having you in charge does turn me on a little." "Well try to keep from getting hard or this will be impossible to get on." She pulled out a pin and the cage. "This pin goes in here. This is one of the shorter ones and so is the cage. I figured you didn't need a ton of room and I wanted to make sure it fit ok in your panties. You'll still be able to pee through this hole but you'll have to make sure to keep it clean and if we have to remove it for cleaning we will. I read that if you slip a nylon over you cock it's easier to get the cage on so let's try that." I slipped the nylon on my cock and she slide the cage over my barely erect cock. It was definitely snug. Ashley produced a lock and slide it through, locking it.. "And there we go!" she said "How does that feel? Move around a little." "It feels snug but it doesn't hurt. I'm not sure what will happen if I get turned on, but I don't see myself getting out of this." "That's the point!" she said kneeling in front of me. With her hand on my balls she began rubbing them before leaning forward and licking them slowly. "Hey - that feels really good but you could have done it before you put it on!" I said as my cock began to swell and strain against the cage. Looking down on her as she made eye contact with me slowly licking my freshly shaven balls. "Oh god...that feels so good." My cock straining harder but not in painfully. "Does it hurt? Or does it just make you want me more?" "No, it doesn't hurt but it definitely makes me want you." "Mmmmm...perfect. Well, girls don't have cocks and little sissies don't get to use theirs so you'll stay like this until I think you're ready to come out. Now follow me and let's get you dressed. We can still do some training but there obviously won't be a release for you since you already ruined that by jerking off before I got home. Why don't you head to the bedroom and get dressed up in your favorite bra, panties and stockings and I'll be right in." I went to the bedroom and put on hot pink lace panties and a matching bra then found some white lace top stockings to go with it. The panties fit snuggly over the chastity device and my cock tried to perk up as I slid the stockings over my freshly shaven legs. Ashley was right, the stockings felt amazing and sent tingles through my body. Ashley came in as I finished putting my stockings on and I watched as she took off her blouse and slid off her skirt God she was hot, I thought. Just irresistible like this. "How does that feel," she asked. "You were right, it does feel amazing on my legs." "Well, I have to say you look a lot more feminine from the waist down now. I hadn't really noticed it before, but your body has a certain femininity to it. You're not all that muscular and you have hips. Just need to get you a flat tummy," she giggled. "Still, I have to admit, you sort of make for a sexy girl." I blushed and chuckled a bit. I liked the compliments of looking sexy. I even felt sexy dressed as I was, but I could feel her stripping my masculinity away. "Get on the bed for me sweetie," she directed, "you already had your pleasure for the day so now it's my turn." She produced two bras which she used to secure my wrists to the headboard. "I'm going to tie up your arms with these sissy. We'll need to get something better, but this will do for now. I want you to be able to focus on using your mouth and not your hands. My toys will do a better job than your fingers anyway," she smirked. She then went to the bathroom and returned with some makeup. "Time to pretty that face up a little," she said as she applied some eyeliner, mascara, eyeshadow and finally some lipstick to my face. "There we go! If it wasn't for the short hair on your head, you might be mistaken for a sexy little slut," she smiled. She reached into the drawer and grabbed her dildo. "Now get my little pussy wet for this nice cock. You're going to watch me cum and get a little sissy training at the same time." She straddled my face as I licked her bare slit. "There you go...good girl," she cooed. I could feel her pussy getting wetter by the minute, soaking my face and smearing my lipstick. "You like getting my pussy ready for this dildo, don't you," she asked. "Oh god, you taste so good." She pulled herself off my face, "now open up that pretty mouth." As I did so, she slid the dildo in my mouth, "Mmmmm wrap your lips around it. Get that cock nice and wet for me. Good girl." I was getting so turned on and she knew it, my cock swelling in the chastity device. She pulled the dildo out of my mouth and slowly slid it into her wet pussy, biting her bottom lip. "Mmmm...so nice." I watched as she took it all the way, making long slow strokes. "I'm getting so wet, you want a taste?" She put the dildo to my mouth and I opened to accept it. "Bob your head and suck it...there you go." With my painted lips wrapped around the dildo, I began sucking it. "Open up that throat sissy...you need to take it all the way," as she shoved it to the back of my throat. I pulled back a bit when it hit the back of my throat causing her to move her hand to the back of my head. "C'mon, take it all the way like a good girl. You might choke a little but you need to learn how it's done. C'mon, please me. Make me happy." She forced my head down on it and as it hit the back of my throat I choked a little. "There you go...keep going" She continued, pulling it out and forcing it back deep to my throat, holding it deep in my throat for a few seconds longer each time. "You like this cock in your mouth, don't you? If you want to wear panties and be a sissy you need to learn this too. Oh, are your eyes starting to water...your makeup running a little." My eyes had begun tearing as she fucked my mouth with the dildo. "Mmmmm...good girl. Now watch how this cock makes me cum." She pulled the sopping wet dildo from my mouth and stood it on end on my chest. She proceeded to straddle it, holding it with one hand and began riding the dildo on my chest. My face was inches from her wet pussy as I watched the dildo stretch her lips and slide deep inside her. "Oh this is so good sissy. If you could only feel this...this is so good in my pussy. Did you think about this when you were stroking your little cock today? Huh? This nice dildo fucking me?" "Yes," I responded "All I could think about was your amazing pussy. I love watching you get off." I watched her ride the dildo, her pussy framed by her garters holding up her black lace top stockings. Her breasts shaking in her bra as she reached in and squeezed her nipple. My cock swelled in its new small cage as she moaned and squealed before finally cumming, "mmmmmm...oh god! So good!" She fell forward after cumming and then moaned, "time for you to clean up, honey." She moved her hips to my face and I eagerly licked her dripping wet pussy. Her wetness covering my face. "There you go my little slut, you like licking my pussy after a good fucking, don't you?" "Mmmm," I moaned, "you taste so good honey." "I'm glad you like it. I expect you to do it anytime I cum, but you're not done yet." She sat on my chest and put the dildo to my face, "my little slut needs to clean this too. Now open wide for the nice cock." I wrapped my lips around the wet dildo, tasting her sweet juices as she slid it deep in my mouth and back out. "Good girl! It's too bad there isn't a little cum on there for you too. I bet you'd like that," she giggled. She untied my hands and curled up next to me, rubbing my nipple through my bra, "You like that sweetie? You like seeing me cum and getting that cock nice and wet for me?" "I love seeing you get off. You get me so turned on. I mean, look at my cock." She pulled down my panties a bit and to take a look at my locked up cock. It was fully swelled in the chastity device, my balls red as my cock pulled at them trying in vain to get hard. "Ooooh, look at that! It looks like you really enjoy this, eh? Dressing like a sexy slut, licking my pussy, sucking cock, watching me get off. I have to admit, you're something of a natural at it. I had always had my suspicions in the past, but I guess I'm starting to understand why our sex life was a little underwhelming before. Given how you've reacted so far, I think you'll enjoy some of the other things I have in mind. Speaking of which, there are some things I want to get for us and, since this is your fetish, I think it's only fair you buy them, but I want to pick it out and for it to be a surprise. Can you give me some cash?" Liking the idea and curious about the surprise, "Sure honey...whatever you need." "Ok, good," looking up and smiling as she continued to move her hand around my body before moving down and massaging my balls,, "just remember that I'm doing this for us, because I love you. I'll probably need a few hundred dollars, but I promise it will be worth it." "Whoa...um...ok. Like I said, whatever you need. I just enjoy making you happy." "Good! That's what you should want. You can stay dressed like this for the night, but let's move into the living room. I can't wait to get our new stuff!" Teased, Denied and Sissified Ch. 04 Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was best to keep my cock locked in chastity. As she pointed out, girls didn't have cocks to play with so I shouldn't be playing with mine. She hinted that we would be exploring new ways to pleasure ourselves and that she wanted to pick a few things to take the experiment further. After about a week in chastity, I came home from work on a Friday and learned she had a full night planned. "I hope you don't mind but I picked out an outfit for you tonight?" Ashley said with a big smile on her face Laying on the bed was a short skirt, bra, white lacy panties, garters and thigh high stockings. "I thought it had an innocent feel to it...though I don't know you'll be so innocent when I'm done with you! Start getting dressed, but I have more! Ahhh...I'm so excited!" She went into the closet and pulled out a wig of long dark brown hair "You should wear this too and I can show you how to do your hair. I'm going to teach you how to put on makeup too." I was a little turned on by it all, but started to wonder if this was going too far. Still, I knew better than to disagree. "Wow! You really went all out!" as I considered how Ashley would further emasculate me, "You're going to make me feel pretty sexy tonight, eh?" "Definitely! There is one more thing I have for you before we work on makeup and paint our nails." She opened the nightstand drawer and pulled out a silver butt plug. "I think you should wear this tonight while we get you ready. I know it may look big, but it really isn't much thicker than the average cock." she said smiling. "I got some lube too. Once we slide it in, we'll get you dressed then work on the other stuff." I held up the butt plug. It did look a little bigger than I expected. Maybe as thick as two good fingers at the widest. "If you lube your ass, I'll lube the toy and help you slide it in." she said with a grin. I put some lube on my fingers and reached around to my puckered hole, rubbing it around and sliding a finger in to get some inside. Meanwhile, she added quite a bit to the toy. "Now get down on your knees and bend over. I want to plug that cute ass of yours and make it mine." Those words excited me and I could feel my cock straining against the cock cage. She rubbed the tip of the plug on my ass, easing it a little at a time, in and out, "Here goes," she said as she plunged it in. I felt my ass stretch as she pushed it all the way in. It didn't hurt going in, but wasn't necessarily pleasant. I couldn't help but squeeze my muscles against it. I was now more turned on than before. "How's that feel sissy?" "Full?" was the best description I could come up with at the time. "I can definitely feel it inside and it feels good. Having you slide it was definitely a turn on," I said as I stood up and turned around. "Ohhh...look at your little dick! It must feel good!" Looking down I noticed some precum dripping out of the tip of my cock and on the edge of the cage. Ashley reached down and collected a bit on her finger, holding it up to my mouth "Open up!" I opened my mouth, sucking her finger clean. "Now let's get you dressed! We'll fit the wig after we get your makeup on so just bring it to the living room with you." I was impressed that everything fit so well. The panties fit over my cock cage, holding it snug. I walked to the living room and Ashley pointed to a chair for me to sit in with a mirror and she began having me put on eyeliner, mascara, shadow, some blush and lipstick. She had me feeling very feminine. Next I turned to face her and she put on the wig. "This color is great but you might want to get a couple more...so you can play with being blonde or redhead! We'll have to see!" she said as she brushed and then straightened the wig, even trimming a couple spots with scissors. "Oh my god," she said "I really think you might be passable. Look in the mirror." I was stunned. With the wig, outfit and makeup, I was looking more female than male. "Wow, this is crazy." I said. I stood admiring myself in the mirror, licking my red lips, touching my nipples through my bra, getting turned on when Ashley brought me back to earth, "I guess you like you're new look?," she smiled, her hand on my ass. "Let's paint your nails before we have some fun." We sat facing each other with my hands on the table as she began painting my nails a soft pink. She noticed me shift in the chair and asked, "How's that plug treating you?" "Oh, it's good, teases my ass a bit. Every time I feel it I think of you owning my ass." I joked. "Good!" she smiled, "I remember the first few times I had anal it was a bit painful...my boyfriend was pretty big...but I got used to it and it felt amazing after that." I was a little taken aback by the shift in conversation. We had never talked about sex with our exes or anything. I was curious though as she had always seemed conservative in bed with me, but, as I was learning, she was a bit more adventurous. I was a little stunned. "I wish I would have known you were interested in anal. Why didn't you say something before? We could have totally done that." "You're not really the kind of guy I would think of doing that with...I don't know...I'm not trying to be mean, but you're the more...like...nice guy, with a good job type I guess. You're not really, um, equipped to be the take charge kind of guy in bed. Now that I know you're kind of a little sissy inside, I'm starting to think of you more of a girlfriend than a boyfriend. I guess I've always sort of been interested in experimenting with girls so you're kind of giving me that chance," she laughed. "Yeah, it does seem like you're enjoying making me into a girl. I guess I thought this might be something we just do every now and then rather than permanent." "I never said it would be permanent, but you knew going into this that it might change the way I feel about you. You need to learn to accept that. I still love you, but this might change the dynamic of our relationship a bit. I'm also exploring my dominant side with you and I love it so far. With the guys before you, I tended to be the more submissive one. Now I guess it's my turn to put you in that role which you seem to be taking too quite well," she said laughing. "Speaking of your role, I think it's time for me you to grab the heels I got you so you can practice!" Her words were a lot to take in, but accurate. I was discovering a submissive side of myself that had been itching to come out for a while and she seemed to be the perfect person to push my buttons. "Now, this is going to take you some practice but you'll get the hang of it AND you must practice. I want you to master this so I can move you up to higher heels. Now - watch me." She proceeded to walk across the room in her own heels. As she turned around I couldn't help but admire her legs and ass. "Are you watching? Watch my feet, not my ass sissy. You'll be staring at it plenty later but right now we have work to do." She walked again then had me give it a shot. I was, in a word, awkward. "I really am trying," I pleaded, "this is harder than I thought." "It's ok," she said "you'll get better at it. Just don't give up and keep practicing. Before long you'll be able to do anything in heels. Now, practice a bit more and pick up in here then meet me in the bedroom. You can leave the heels on." She disappeared into the bedroom as I took a few more paces, putting a few things away. "I'm waiting for you!" I heard from the bedroom. I walked (stumbled?) to the bedroom to find Ashley sitting on the edge of the bed. "Get on your knees and put your face between my legs." I knelt down in front of her to find a dildo attached to a strap on harness. I looked up, "Whoa." "It's all yours sissy! It's a little bigger than the one I've been using...about 7 ½ inches. I decided I wanted something a little bigger for myself so got you one too. I think 7-8 inches is the perfect size and I think you'll discover the same. Now open up and show me how a good sissy sucks cock." She stood up, the dildo swaying. When Ashley caught me in her panties a couple weeks ago and said she wanted to "explore" my little fetish, I never thought she would take it this far. I had now gone from putting on panties occasionally to being fully dressed, make up, butt plug in my ass and on my knees sucking a dildo. I didn't think I would want all of this, but Ashley had a way of keeping me turned on, taking small steps and making me want it more and more. She seemed to gain enjoyment out of it as well. I grabbed the dildo with my hand, wrapping my lips around it and taking it into my mouth. "Make sure to tease it a bit, licking the head and shaft up and down too. Make eye contact too. I know you probably haven't had many amazing blow jobs but I've been told I'm quite good so I'll teach you what I know." The few I got from her were quite good, but I wondered if I had missed out on some of her best work. I followed her instructions, licking it up and down, around the head and taking it back into my mouth, sliding down the shaft with my mouth. Looking up at her, I watched as she reached down for the back of my head, "C'mon sissy...just like I taught you...take it all the way." She pulled my hair back with her hand, then pushed my head down on it, "If you're not going to do it right, I'll do it for you." She began pumping her hips and fucking my mouth, pulling me deep and holding me there for a moment. "Mmmmmm..." then releasing me and fucking my mouth again "your eyes are watering. I don't know why I love fucking your mouth so much with this dildo but it gets me so wet." She continued as saliva dripped from my mouth. I didn't want to resist. I grew more turned on as she made me feel like a slut. "My little slut want this in her little hole? You had to know there was a purpose behind that butt plug." I did indeed have my suspicions and she confirmed them. She pulled my head off for me to answer "Yes, but...be gentle?" "Oh, don't you worry sissy. I'll be gentle to start but I think you'll be begging for more when I'm done. You're lucky you're getting so much attention." My cock was throbbing in the cage now, straining to get erect. "Take those panties off slut and take out your butt plug. I want to see how that little cock of yours is doing." I took off my panties and squatted to remove the butt plug. I sort of felt a relief when it came out but knew that my hole was only going to be filled again. I stood up while she got down to examine my cock. "Hmmmm...looks like someone is trying to get excited. I bet you wouldn't be able to keep your hands off of it right now if it wasn't for this little cage." She licked and sucked on my balls "You like that sissy?" "Feels so good. I want you so bad." "Hmmm, I bet you do and guess what, you can have me but you're not getting out of this cage." as she wiped her finger on the end again, picking up some precum and delivering it to my mouth. "You're probably starting to like the taste. Now get your ass ready for me and bend over on the bed." I got my ass lubed up again and she got the dildo ready, though it was already pretty wet from my saliva. . "I'm gonna start nice and slow, but that plug should have loosened you up a little. Just relax." I felt her place the head of the dildo on my little hole and she slowly pressed it in, stretching my ass since the dildo was thicker than the plug. She began with short strokes, pushing a little more each time. I could feel the rush through my legs as she pushed in further, her hands on my hips. "C'mon sissy...take it all..." I could feel it slide deeper inside, stretching me and rubbing my prostate. She continued slowly, deeper and deeper until I felt her against my ass. It felt like the dildo was practically in my stomach. "Oh sweetie...you're good at this...you want to know what it's like to get fucked now sissy?" She started picking up the pace, taking long strokes. I couldn't get over how good it felt "Oh god...that's good...fuck me." I panted. "Yes, sissy, that's what I want to hear. Tell me how bad you want it!" She began really going at it, pushing and pulling my hips and I followed suit, picking up the rhythm. "Don't stop. It's so good." I said as I felt the dildo rub against my prostate. "You fuck me so good." "You want to watch me fuck you? Get on your back and let's get those legs in the air." She pulled out and I flipped over. She propped my ass up on a couple pillows. Lowering the head of the dldo to my ass, "Tell me how much you want this cock. How bad do you want to get fucked with that little cock locked up?" She rubbed my balls softly with her hand. "Fuck me please...I want you to fuck me with that big cock." "Mmmmm...yes! You love it don't you slut," she said as she began removing her bra, "With that little dick locked up I suppose you can see my perky tits again. I was worried before you wouldn't be able to help but stroke but I suppose I don't need to worry about that anymore...just us girls! Now take this cock sissy," as she plunged full bore into my ass. I let out a soft moan as she went deep in my ass. We made eye contact and I watched her perky little tits jiggle as she began fucking me harder. My locked up cock bouncing around as she went deep and hard into my ass. "Oh god...fuck me...don't stop." I exclaimed, "God, I might even be able to cum!" Looking me in the eye "Tell me how much you love it. Tell me how much you love me owning your ass and little cock." "Oh god, I love it. I love your cock. Don't stop fucking me. I love your cock in my ass. My little cock is yours." It felt amazing and my cock began to dribble a little cum. It wasn't like the orgasms I was used to. It felt good, but I still felt aroused and wanted more. A big smile came across her face as she slowed to catch her breath, "There we go sissy...a little squirt for me!" She reached down to gather with her fingers what wasn't trapped in the cage, "Clean it up like a good girl." I sucked the cum off her fingers as she pulled the dildo out of my ass. I wanted more, but knew it was probably her turn. "Oooooh, such a little cock slut. I think you lost your innocence tonight. I'm so turned on right now," she said as she took off her strap on harness and panties, "Stay right there slut and taste how wet I am." She climbed on my face as she always does and I licked her perfect pussy. She moaned a bit and bucked her hips on my face, "Lick that clitty for me and make me cum." I buried my face between her thighs as I sucked and licked her clit, her hands on my head. "Oh god, right there...don't stop, don't stop!!" Her thighs pressing hard against my head as she came, "Oh god!! I'm so horny...I want you to fuck me good now." She reached to the nightstand and produced another strap on harness with a different dildo but the same size she used on me. "I bought this for you. Since that cock isn't of any use to a sissy I figured you could fuck me with this. Put your panties back on, and then slide this on." I slid on the harness while, deep down wishing it was my cock but still wanting to get her off. If my cock couldn't do it, at least I could keep her happy with this. She pulled me to the bed on my back and straddled the large dildo, lowering herself slowly, rocking a bit back and forth before taking it all the way, grabbing her perky breasts and moaning, "Oh god, so good." I began rocking my hips, matching her rhythm as she bounced on the dildo faster, my hands firmly positioned on her hips. I watched her moan harder as my cock strained against the cage, getting so aroused before she fell forward with an intense orgasm. I could hear her panting in my ear, when she said, "I want more...make me cum again." Here I was, doing all the things I had hoped to do with Ashley in bed, but doing it with a dildo while my cock was locked in chastity. She got on all fours, with her small round ass pointed in the air and I slid the dildo in from behind. She moaned as I thrusted in, arching her back. I took long hard strokes as she moaned for more, "oh god, fuck me with that big cock." We moved in rhythm until her body tensed and moaned loudly, "ahhhhh!" I pulled out the dildo and laid next to her as she collapsed on the bed. Panting, trying to catch her breath, she smiled at me as I took off the harness. "Oh god, that was amazing. Making you into a little sissy was the best idea you've ever had. I love you," as she pulled me towards her and we kissed. I was spent too, laying there close to her, reliving her moments of ecstasy in my head and loving every minute. "I love you too. I love making you cum and I love the attention and how close we've become," I said. We kissed again, holding each other for a moment before I got up to clean up our toys up and wash the cum out of my cock cage. As I returned to bed to curl up next to her she whispered, "I can't wait to do this again. I loved fucking your ass and the feeling the dildo inside me, but I can't help feel something is still missing. I'll have to give it some thought, but for now I think you should start wearing the wig and makeup whenever you're home." "Whatever you say sweetie," I replied before realizing that I had just committed to living as a female whenever I was at home.