Barely able to contain the inevitable erection that had sprung up in the store and remained uncomfortably insistent all the way home. I had surreptitiously adjusted myself so that it was trapped vertically inside my tight jeans, attempting to make it less noticeable as I walked, but this had had the effect of rubbing in such a way that I almost came in my pants before I got to my house. 

I desperately wanted to wank off immediately, but that desire conflicted with wanting to see myself fully dressed. 

I held off. As I donned each article of clothing, I checked myself out in my full-length mirror.

I'd never considered it before, but I guess I have a nice-looking ass. The panties somehow made it sexy. Covering the top and leaving the lower half and well-defined cleft where the cheeks meet the tops of my thighs. I grasped my cheeks and lifted them up, then let them drop, watching as they jiggled slightly when they returned to their resting position. 

Next came the little bra. It was the kind that has no clip, you just pull it over your head. My pecs just barely caused the cups to bulge. It was more like a very tight undershirt cut off above the midriff. Now I stood and admired myself again. My hands went to my abs and I slowly moved them upwards over the cotton of the bra. I pretended I was a girl, seductively playing with my tits. Pre-cum surged out of my cock, soaking a spot on the front of my panties.

Oh god, I wanted to wank now. Seeing myself in ladies underwear in my mirror. Watching myself pose. 

Again I held off. I pulled on a t-shirt, covering the bra. For a minute, I pulled my jeans back on. Now I was hiding the woman's clothing I was wearing, which was just as erotic, somehow, as being able to see it. I imagined joining my housemates in the living room wearing a bra and panties under my regular clothes.

But I still had two more items to try. I turned away from the mirror and looked back at myself as I slid the waistband of the jeans down. I was turned on like crazy. Seeing the curve of my panty-clad ass slowly being exposed. I was being a tease to myself. It was a rehearsal for the following day. 

The jeans were discarded and then I pulled on my knee socks. Standing and admiring how I looked. Slim and sexy, like a young girl, for sure. I couldn't stand to delay any longer, I stepped into the little skirt I had bought. I watched myself as I reached back to do up the zipper and single button at the small of my back. It caused my hips to thrust forwards, and my hard cock, even constrained by my panties, was visibly bulging out the front of the skirt.

It disappeared as I stood straight again. The skirt came about half-way down my thighs. With a little imagination I could see myself starring in Japanese Schoolgirl porn. 

I posed in front of the mirror. Acting coy, a finger in my mouth, toes turned in and my ass sticking out.

I thought I looked pretty hot and I knew I wouldn't control myself much longer. All the pent up excitement would have to be released.

Again I turned away from the mirror. Now I lifted the hem of my skirt at the back, exposing my ass. Slowly I began to peel down the panties. I exposed my bare cheeks. I stopped as the panties reached the cleft below. At the front, I could feel my stiff cock pointing downwards, trapped and straining against the fabric.

I stood again and looked at myself as I reached down, lifted the front hem and started rubbing my penis.

I had to release it. I tugged the panties down until I sprang blessedly free.

I wanted to see the skirt pushed out by my cock. Tenting the pleated material. Some of my favorite shemale and CD porn had included this. I am very aroused by seeing a skirt bulging out from the hard dick it conceals. Now I was going to see myself doing this. 

I wasn't disappointed. It was so fucking sexy! I swayed my hips and watched the effect on the skirt. Felt my swinging cock caressed by the material. 

Then I could wait no longer. I reached down, lifted the skirt, grabbed my cock and started jacking it. I watched myself, my girly self, in the mirror. I think I lasted about five strokes. I shot cum at the girl in the mirror and she shot her cum at me. 

I was exhausted. I took off the skirt and hung it up carefully, but I pulled up my panties from the tops of my thighs and kept my bra on. That's how I went to sleep that night, a slutty little schoolgirl.

I had work the next day, which was probably for the best. I couldn't remember cumming so much in so short a time since I first discovered wanking. 

But I was ready, willing and more than able the day after.. All morning I had to stop myself from jerking off before my planned appointment with Dave.

Before I logged on, I dressed in my new undies and socks and then pulled on my jeans and a t-shirt. 

I didn't know for sure if Dave would dig the entire femme ensemble. I figured from his comments that he'd like the panties so I planned to show those first. Then Maybe expose the bra and if he liked it I could switch to the skirt. I really hoped he would want it all, because I'd been fantasizing about being his little girly boy.

We'd both changed our camera angles so they showed more of ourselves. Dave could see me from head to toe but it meant that I had to move closer for him to get a clear view of my dick or ass. But that was OK. Dave was sitting and I could see him from the knees up to his handsome face. 

We talked for a few minutes and then he asked me if I wanted sex with him. 

"For real?"

"Oh Robbie, I wish! But no, this is all we can ever do."

"That's OK, I like this."

I rubbed the front of my trousers. 

"I got something for you, Dave..."

Pulled on my zipper and exposed the pink cotton bow at the top of my panties.

"Oh sweet boy!" Dave stood, undressed in a flash and exposed his cock. I watched it grow in his anticipation of me showing myself to him in panties.

I hurriedly dropped my jeans and stepped out of them.

Turning a 360 in front of the cam, I let Dave enjoy the sight of my hard cock, tight inside my panties and then my round ass. 

"Do you like them?"

"So much!" 

He was gripping his huge cock and stroking it. Showing his appreciation for my pantied ass.

"Do you like me being girly for you?"

"You're my fantasy!"

"Would you like to be with me all dressed up?"

I lifted up my shirt and gave Dave a brief glimpse of the bra I was wearing.

"Oh Robbie!"

"Do you want to see?"

"YES oh god yes!"

He was stroking himself faster. I was sure now that he would like to see the dress as well, but I was worried that he would shoot before I had a chance to get it all on.

"Stop stroking, Dave."

"I can't!"

"Then I won't show you any more."

His hand left his cock. I had discovered that even though I felt submissive to his big cock I also had some power. He wanted me and I was the one who controlled how much he got.

I stepped out of the frame and pulled on the skirt. Now I moved back into view, far enough away that he could see me completely. Wearing my skirt and long white socks. As I stood there, I lifted up the t-shirt and pulled it over my head, displaying the bra I was wearing and also my shaven armpits. I held my hands to the back of my head so he could see it all. So he could see how feminine I had made myself for him.

"Now you can stroke it, Dave."

His hand flew back to his engorged member. I imagined I could see it actually throbbing.

"Oh Robbie you're so cute. I can't bear it. I want you. I want to touch your body."

"Only touch me, Dave?"

I moved closer to the cam. Turning to one side and pushing out my ass.

Then I lifted the back of my skirt and let him ogle my panties. The curve of my ass. I caressed my ass.

"Mmmm... would you touch me here?"

I began to peel off the panties.

"Does daddy want to see my bare ass?"

He groaned and stroked.

I tugged down the panties like I had rehearsed before. Slowly and as seductively as I could. I watched him in his chair. His legs apart and his massive cock in his hands.

I turned completely away from him and bent over to lower my panties all the way to my ankles. Staying in that position for several seconds, I whispered to him.

"I want your fat cock, Dave. Right here."

And then I moved a finger to my anus, as I had done for the other man. Pressed into myself. I spread my legs so that he could see my balls hanging down between my thighs. 

"You like your little girly boy?"

"Oh Robbie, I love you! I want to push my cock into that sweet little hole. You're so sexy in that outfit. Like a perfect girl, but with the extras I dream about."

"Mmmmm... I wish you could do that to me. I want to know how it feels." 

I turned around then. Let him see my erection tenting the pleats of my skirt. I gripped myself through the material and watched him stroking. 

"Will you cum for me Dave? What can I do to help?"

"Lift up your skirt, baby. Lift it up and show me what you have hidden under there."

I lifted my skirt and let it drape over my hard dick. Swaying my hips again in front of the camera. 

"Like this?" 

"Yes! Like that. Show me your sweet dick. I want to stroke it until you cum."

"Like this?"

I stroked my cock for him. Pulling the foreskin back over the shiny, purple head. Letting his see how wet I was. Back and forth, gliding like silk over my head.

"Mmm yeah. I want to cum for you Robbie."

I leaned down to face the cam as he had done before. 

"Cum in my mouth. Shoot for your baby."

I licked my lips and then opened them. My monitor showed my open mouth on cam, alongside Dave's rigid member.

I watched his last few strokes and then watched him come off. Close up. Watched as though his dick was mere inches from my face. Saw his cum shooting, saw it hitting his chest.

"Oh... you came so nice!"

"You made me cum!"

"Now me!"

I stood back up and moved away so that Dave could see all of me as I jerked my meat. Me in my skirt and knee socks and bra. Moving my hand up and down my shaft, pulling back my foreskin. I moved my other hand up my abs and slipped my fingers under the bottom of my bra. I let his watch me tickle my nipple as I stroked. 

"Mmmm Dave, I wish it was you playing with my nipples and wanking me off. I want to feel my cock in your big, strong grip."

"Yeah baby boy, I would love to make you cum."

I could just stand here and let you play with me."

"Yes, my little fem toy boy. I would make you cum and cum."

"You've done it before and I liked it."

"I want to do you for real."

"I want to be done for real, too!"

It was just sex talk. Part of the fantasy. But I realized that yes, I really did want to be done for real. I looked at myself in the monitor. A femboy masturbating for a mature man. And I wanted it. I was loving it. It turned me on. I wanted his cock. I wanted to feel his hands on me. A man, touching me all over. Both of us naked. In his bed! I wanted to be taken! 

"I'm cumming!" 

The first two spasms of my cock shot my cum a couple of feet in front of me. Dave watched and voiced his appreciation. I temporarily lost the ability to form actual words.

"Unnnnngg. Unnng. Unnnng". 

I let go of my cock and walked towards the cam again. The rest of my jizz dripped out. My cumming cock swayed as I walked.

"That was nice!" 

"I enjoyed watching. You're so fucking sexy. You know how to excite me."

"Well, Dave, the thought of you excites me, too. Your big cock and handsome face."

"Sweetie, you say such nice things. I want to hold you in my arms and make love to you."

"Like I was a girl? Looking like this?"

"Yes, looking like that. Or not. I am turned on by you, either way."

"I'm turned on being this way."

"Well I can see you are."

"I want cock. I want to be fucked while I am a girl."

"Robbie, I want it to be me. I want to see my cock entering your sweet hole. Giving you what you crave."

We chatted on for a few more minutes and then he had to sign out. We were going to do it again in a couple of days, when his wife was out.

Dave's last comment gave me another idea and I made another little shopping trip. 

This new-found sex play was bankrupting me. 

I had just enough in my bank account to buy a sex-toy at Good Vibrations, across town. 

It took some nerve to enter the store, but they are very cool there and the servers are completely non-judgmental. 

I told the girl that attended me that I wanted to buy a dildo and she asked if it was for vaginal or anal play and if the person was experienced or not. She asked me questions in a way that let me answer them without admitting it was for me. 

I said it was for someone inexperienced in anal play. She suggested a butt plug, rather than a dildo. 

She patiently explained how they worked. I already knew, but it was fun listening to a cute girl talk to me about it. It became difficult to remain composed and not show my excitement. 

In the back of my mind I knew that soon I would be penetrating my ass with one. 

We settled on something about seven inches long. 'The person' could put as much or as little as they wanted inside themselves and work up to the time when they could take it all. She also sold me some lubricant.

I carried the little brown bag with me back home on the bus. I felt as though every other passenger knew what I had. Like the bag was clear plastic. I felt shame, combined with eager anticipation. The thirty minute journey seemed to take hours.

Even though I desperately wanted to try it out, I decided that it would be better if I waited until my next session with Dave. It related to my preference for 'real' porn, I think. I wanted a first-time experience with Dave and it would be better if it really was the first time.

So I left the butt-plug in its plastic. You know - the kind of plastic shell that is almost impossible to open. Dave would know for sure that it was brand new and unused when he saw me struggling to get at the damn thing.

I tried a few new camera positions as I planned the best way to show Dave. I thought about lying on my bed with the cam looking up between my legs. I liked how I looked with my legs apart and my cock and balls showing. As I lay there spreading my legs it was easy to imagine a man climbing onto me and fucking my virgin ass. But I couldn't easily see my monitor like that, nor could Dave see my face. 

Eventually I decided that the best way would be to place the plug on a stool, pointing up, and then lower myself onto it. I set the cam up so that it would be close to the action. Even though Dave would only see from my waist to my knees. I still put on all the girl's clothes before sending him the room-invite for our next date. That was for me, mostly. I was going to get fucked, and I wanted to feel feminine while it happened.

Dave answered my invite the next day. I was dressed as before and was sitting in front of the cam.

I wasn't wearing the panties this time and was already erect in anticipation, so my hard-on was lifting my skirt. 

Having waited all the previous day, I was anxious to use my new toy. 

I leaned down so Dave could see my face and said hello. I blew him a kiss and said I had bought him a present. 

"Oooh, what did you get?"

"You said you wanted to fuck me."

"You know it, honey."

"Well, this is as good as we can manage..."I sat back down on the stool and brought the packaged butt-plug in to view. I held it for him to see.

"It's never been used, Dave... and neither has this..."

I stood, turned around and lifted my skirt, showing my ass to him. I used the fingers of one hand to part the cheeks and show him my bumhole.

"I want my first anal penetration to be with you, Dave."

"Oh baby!!"

I then spent several very frustrating minutes trying to get the butt-plug out of its plastic wrapper. In the end I had to run down to our kitchen and get a pair of scissors. The house was empty but I got another sexual charge from walking outside my room, dressed as a girl. I was liking it more and more.

Finally the toy was in my hand for the first time. 

I ran my hand up and down it. Telling Dave I wished it was his cock. All the while I could see him in his chair, legs apart and dick in hand. He kept up his encouragement.

I set the plug on my chair then undid my skirt and let it fall to the floor. Grabbing the lube, I dribbled some over the plug and rubbed it up and down, making sure that Dave could see. Then I leaned over and dribbled some more lube on the crack of my ass. Using that and what was already on my fingers, I slipped a digit up my hole and made sure that my ass was good and slippery.

Finally, finally... I stood with legs either side of the stool, over the butt-plug, and began to bend my knees.

My cock was as hard as it had ever been, standing straight up. My ballsack was tight. Dave could see the tip of the plug as it slipped between the cheeks of my ass.

"I'm going to take it for you."

"Oh honey, you're so brave."

I lowered myself further.

"I can feel it, touching my little ass now."

"Take your time, baby."

"But I want you, Dave."

Lowering myself further, the tip entered my hole. It was like my finger but I knew it was going to be so much more.

"It's in me. It feels nice."

Lower again and I felt the widening plug begin to stretch my ass.

"Ooh... it's so big..."

I kept a steady downward movement. I knew I was going to be taking the whole plug up my ass within minutes but I reached down and gripped the edges of the stool to ensure that I didn't slip and go too far too fast.

"Stretching me. Big cock in my ass."

I watched the plug entering me on my monitor. My cock was still iron-hard. 

I got to the widest part of the butt plug and it became difficult to go further. 

"Oh, it's so big and I'm so tight. It hurts a little bit."

"Don't hurt yourself! I don't want you in pain!"

I stood briefly and poured some more lube on, then sat back down on my toy.

It felt easier the second time and I overcame the discomfort.

"I think I can take it now. All the way."

I pressed down on the upright plug and felt it suddenly go all the way into me. My anus clamped around the narrower part just above the flange.

"It's in me! All the way. I took it up the ass!"

Dave furiously stroked himself as he watched me.

Now I was sitting on the stool. The butt-plug was firmly up my ass. It felt great.

My cock was so engorged I thought it might burst. Precum had been steadily leaking out and there was too much to be contained within the folds of my foreskin. You could see it, glistening, dripping, off the end of my penis. I ran my finger up my shaft and collected some, then leaned forward so Dave could see me lick it.

"Tastes good, Dave."

"I'm sure it's like sweet wine."

As I sat back up, the movement of my body affected the position of the plug inside me. I liked that and began rocking on the stool. 

My cock bobbed up and down.

"Do you like it?" Dave asked.

"I love it! I feel so full, and it makes my cock tingle."

Can you stand up?

I did so. The shape of the plug kept it tight inside me. I turned around and bent over so Dave could see the end, nestled between the cheeks of my ass.

"It feels nice, Dave, I'm pretending you are fucking me. Pretending you have your cock up my bottom."

I wiggled my ass for him and heard him groan. I looked behind me, to the monitor, just in time to see him shoot. 

"Yeah Dave. Cum in my ass! You love my ass, don't you. Femboy ass. Mmm Dave. So good."

Dave collapsed back in his seat, looking spent. 

"You're so fucking sexy! That was unforgettable! Thank you! Thank you! You let me share your first-time."

"I loved it. Actually, I'm STILL loving it. I think I'll keep it inside me for a while."

I stood up and pulled on my panties. Enjoying the feeling of them sliding up, over my filled ass.

My hard cock poked out above the waistband. I was intending to whack off, for myself and for Dave, but he told me he couldn't stay.

"I wish I could. This was the best experience I've ever had. I want it to go on and on. But my wife will be home soon."

"That's OK, Dave. Thanks for being here. I loved sharing my first time with you." 

And I had. He was a nice, caring handsome sexy man with a great cock. I was lucky to find him to explore my sexuality with. 

Dave told me he would be going out of town on business so we couldn't meet again for a while. He gave me his email addy, the secret one he used for signing up to porn sites, and said we could communicate that way. 

And then he was gone. 

I was about to close the cam when I thought about the camsite again. I set the cam up in the position I had considered before. At the end of the bed, looking up between my legs. It only took a few seconds to log on and open a public room. 

Then I laid on my bed and started to ease the butt-plug out.

It took some time. The gentle taper at the top of a plug is easier to get in but the more severe angle between the neck and the widest part is harder for a sphincter to negotiate. 

Eventually I was able to pull it out. And then I pushed back in. Not all the way, but close. Then out and in again. Over and over. Imagining a cock. Imagining a man. Fucking me. I spread my legs wider. One hand manipulating the toy in my bum, the other gripping my cock and masturbating. I felt myself almost cumming and stopped. Just lay there until it subsided. Then went at it again. Letting my mind conjure up scenarios, letting my ass and cock send my brain messages of pleasure.

I managed to edge for nearly an hour before I couldn't bear it any longer. Had to cum. Allowed myself to cum.

This time I rammed the plug all the way back in. Allowed my hand to come away and it stayed tight inside. 

I spread my thighs as wide as they would go and stroked as fast as I could. It didn't take long. Cum boiled up and out of me. Spurting straight up and then dropping back down on my belly and chest. 

It was another fantastic orgasm. I straightened my legs and let them flop down on the bed. Then I leaned over and checked my cam room. I'd had nearly fifty viewers at one point. Watching me fuck myself and wank off. Now they were leaving, but I read back though the comments. So many compliments! 

I turned off the cam, extracted the butt-plug and relaxed in a glorious afterglow.

Even though Dave wasn't going to be online, I still wanted to keep putting on shows while I jerked off. It had already reached a point where I felt as if a cum was wasted if I didn't have someone else watching when it happened.

For the next few weeks I was online whenever I could be. I started to see login names I recognized. I had several regular viewers, but I declined all invites to 'go private' and preferred to keep to my own pace. Yes, I knew I was giving a show but, ultimately, I was masturbating. Having men watch me and teasing them with my ass and cock added to my own enjoyment. I used the mic more and asked coy questions of my viewers. 

"Do you like my little bum? Would you like to fuck me? Do you want me to suck you cock?" things like that. I know it made them more excited when they watched me.

Some days I dressed in my girly clothes and some days I didn't. I usually used my butt-plug, though. Sitting down on it on my stool and stroking my cock straight toward the camera. It became much easier to penetrate my ass, but the sensation was still fantastic. 

A couple of paydays came, which allowed me to expand my wardrobe slightly. I bought some lingerie for men off the web. 

I loved how the 'manties' that I had purchased made me feel when I put them on and admired myself in the mirror. And on cam they were well received. They complimented the shape of my ass; defined the crack where my men wanted to be. And I loved to slowly, teasingly, pull them down. Getting that reaction from the men who watched me was like a drug. 

Some men's lingerie is designed to accentuate the penis, but the things I chose were tailored to make my ass look more sexy. 

I sure felt more sexy when I wore them. Within a couple of days, I had ordered more and when they arrived I had enough to wear some every day. 

I started to wear panties when I left the house, then. I was always excited by my secret.

I wore them to work. I wondered how many other men I interacted with each day were secretly wearing women's underwear as well. 

Who could say? But I had joined their ranks: the secretly lingerie-clad men of my city. 

My boxers were consigned to the drawer. I was a full-time panty-boy now.

 

Part 2 to follow.