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.