Straight To Bi. Part 1. free porn video

After I finished university, I struggled for a good-paying job, and money was tight. But I couldn't face living back at home. I managed to find a room to myself in a house-share with two other guys and three women. We were mostly in our early twenties and doing various entry-level jobs. One guy, Pete, was older, about forty five. He was on a temporary assignment in our city and didn't want the hassle of renting somewhere unfurnished.

At home I had shared a bedroom with my brother and at uni I'd been in a shared room too so, even though I wasn't alone, my own room in the house gave me some privacy for the first time in my life. 

That privacy, plus lots of free time away from my crummy part-time job, gave me an opportunity to develop a healthy interest in internet porn. An opportunity that I grasped with both hands... 

It didn't take long to graduate from straight porn. 

I soon realized that I was excited by shemales. 

I didn't immediately want to admit to myself that I liked watching their cocks, but what else could it be? 

The guarantee of anal sex was a consideration. One way or another. 

I progressed from watching a shemale getting fucked, to enjoying them fucking other shemales and then to watching them fuck guys. 

Each phase needed me to admit to myself that maybe I wasn't entirely straight. 

Each step was a hurdle, but each hurdle became easier to clear. 

I liked watching cocks. Hard cocks. Cocks being stroked. Cocks fucking asses. Men's asses.

The biggest hurdle, one which I put off for a while, was searching for actual gay porn. Once I did, there was no going back. 

I let go of my inhibitions and watched men with men. 

I think I found all of this so arousing because I had never done anything with another guy. 

New things are always more exciting, don't you think? 

Anyway, I got into watching videos of guys stroking their dicks when I masturbated. 

Big dicks, in particular. 

I'm of Asian descent. Not hugely well-hung, just average. Uncircumcised. Those big ones you see online gave me a sense of inferiority that somehow made it all more erotic. 

I realized I may have submissive tendencies, even though it had never surfaced with any of my girlfriends.

I found one of those webcam sites and became a regular viewer. I prefer 'real' and homemade porn to the videos produced in studios, so watching real people masturbating for a live audience was perfect. 

Some of the cams are professional artistes, but there are plenty - especially of men - who are just exhibitionists who do it for their own satisfaction.

I found two or three guys that were regular broadcasters and commented often enough that they remembered me when I visited their rooms. Each had a big cock. 

I stroked myself as I watched these men bring themselves off. 

Like other viewers, I used the anonymity of the web to make very explicit comments. I told them I wanted stroke their big dicks and suck them off. Things like that. I got excited as I types in my messages and I could tell that they enjoyed all the comments. It obviously excited them to know that men wanted them and that they were masturbating while they watched.

One day a man I regularly watched PMed me to join him privately. 

All my favorites were older. This guy was probably about 50, judging from what I saw of his body. But I enjoyed watching because his cock was big and fat and it made me very horny when I saw him jerking off. I fantasized about stroking it. Sucking it. 

Unfortunately, I had to admit that I didn't have a webcam. He messaged me back that I had to go out and get one. 

My subservience to him, to his big cock, even through the web, took over. I agreed that I would, and we made a 'date' for a mutual jerk-off session the next day. 

It took most of my spare cash to get the cam but I was undeterred. I bought a decent model and set it up.

One of the options was to keep a video for one month each time I used the cam. I decided to make this the default. 

I was frustrated when I logged on the next day and my 'date' had left a message that he couldn't join me. I was all keyed up to go online with my cam though, so decided to open a public room - like all those other men I'd been watching.

I angled the view so that it was showing just my crotch area. I was still dressed but had a strong erection at the thought of what I was doing. I know that 99% of the people looking at these cams are men. I was intending to display myself for men to look at. It was another bold next step for me.

I started out with no viewers. I was looking at other men on other cams. Watching men stroking themselves. 

I rubbed my erection though my jeans as I watched. 

Then I noticed that I had a viewer. It excited me. I spread my legs and rubbed myself. He wrote that I should take off my jeans. A stranger. Just words on the screen. Instructing me to expose myself to him.

I unbuckled my belt and rubbed myself again. I stopped and wrote back that I had never done this before. I was shy. I was reluctant to show myself to a horny man. I think that excited him. He wrote encouragement to go further. 

I undid the button and pulled down my zipper. 

I put both hands down inside my jeans. He wrote that I shouldn't be shy. 

"Take off your jeans. Slip them down."

I lifted my hips off the seat and slid them down over my ass. They were around the tops of my thighs. My boxers bulged with my hard-on. Like that, I couldn't spread my legs. I tugged my jeans down so that they bunched around my ankles, out of shot, and then I kicked them off completely. 

Now I sat with my legs apart showing my underwear to another man. I rubbed myself again through the thin cotton. Tracing the outline of my hard cock. 

He asked again for me to show him. Wanted to see me naked. Again, I lifted my ass and slipped my underwear down and kicked it off.

My erect cock stood straight up from my lap. 

He was very complimentary. Said how sexy I was and how much he liked my dick. I started to stroke it. The excitement had made my pre-cum flow and there was no trouble sliding my foreskin down over the head of my penis. I slid my hand down, revealing the head, shiny with my own natural lubrication. My viewer typed in more encouragement. By this time, I didn't need any. I stroked my hard cock and looked at myself on my monitor. 

I was so aroused. I was watching my own cock on screen. Watching myself masturbate.

Now that I was exposed, more men entered my room and started commenting. I had five men telling me how sexy I was and what they'd like to do with my cock. 

More strangers. Strange men, offering to suck me off, stroke me to orgasm, take my cock in their ass. 

I only lasted a few minutes. I became so excited and couldn't keep from cumming. 

When I felt it start, I pulled off my t-shirt, stroked faster and faster, reading the excited comments and watching my cock on screen. The orgasm shocked me by its strength. I shot all up my chest and one spurt hit the underside of my chin. 

The men watching me all posted appreciative comments and one by one left the room. I sat watching my softening cock on the screen. That had been intense, and I looked forward to doing it again.

But I also wanted to have my promised private time with my cyber-friend. Before I logged out, I left him a message to say when I would be online the next day and that I hoped we could connect.

Next day I booted up my laptop and logged into the cam site about an hour before my hoped-for 'date'. I heard a chime. It was an invite to join a private room. 

I was happy to think my message had prompted my friend to contact me for a one-on-one wank session and immediately felt my cock begin to stiffen. I had thought about it all the previous evening.

As I joined the room, I saw that it wasn't who I expected. There, before me, was a cock I had not seen before.

It was huge. Perfect, in my judgment. Exactly the shape I had decided was the most sexy. Cut, fat and long. The head was wider than the shaft, but not so wide that it looked like a mushroom. The shaft was firm and almost dead straight, rather than with a curve. The big vein underneath was clearly defined. It was all surrounded by a neatly trimmed bush.

My cock came to complete attention. 

I typed in 'Hello, do I know you?'.

My cam partner replied that he had been watching me the previous day and had enjoyed it so much he wanted to do it again. In fact he had set up his cam for the first time just so he could wank with me, if I wanted. 

I recognized his ID then. It was the guy who had spent most time with me yesterday. The one who had coaxed me to reveal myself. Wow, he was new to this as well. And I was going to be the lucky guy who first got to watch him stroke that marvelous penis to climax.

I stripped off, turned on my cam and joined him in the room.

Now, for the first time, I could see both his cock and mine in adjacent windows.

Then I heard his voice asking if I had my mic on.

It had been off, so I toggled it on. Now we could talk to each other as we masturbated.

"You were so sexy yesterday, I couldn't think of anything else but seeing you again."

"I'm glad you did. I love your cock, It is so big."

"You made my cock big, sweetie. I love watching you stroke yourself. I want to reach through the screen and touch you all over."

I was surprised to be called 'sweetie' by a man, but actually quite liked it. 

I think, as had happened before, his big hard cock, so much bigger than mine, was making me feel submissive. Being called 'sweetie' by another man made me feel feminine somehow. I liked how it felt.

He asked me to take off my shirt and show him my bare chest. I heard him groan a little.

"Do you like that?"

"Yeah, baby. Young, smooth, boy. Yeah, you're such a turn-on."

I ran one hand up and down my flat stomach as I stroked myself with my other hand.

"I'm glad I excite you. Your cock is so nice. I wish I could stroke it. Suck it. Suck daddy's cock."

I couldn't believe I'd said that. But after a second of embarrassment I realized I meant it. I knew that I really did want to stroke his cock and take it in my mouth. The 'daddy' part seemed to fit the fantasy he had instigated.

"Oh yeah baby, talk to me like that while I watch you stroke, while I enjoy the view of your slim body."

I did as he told me. Rubbed my cock up and down. 

I told him how hard he made me. 

I changed the camera angle slightly so more of my torso was visible for him. 

I tweaked my nipples and said how sensitive they were. Then told him I wished he could suck on my nipples while we stroked each other. 

I gripped my cock with both hands, changed the tempo, sliding my hands slowly up and down my shaft. Asked him if it excited him, knowing that by telling me 'yes' he was breaking new ground for himself and becoming more and more aroused. 

"Do you like my naked body?"

"Oh yes."

"Do you want to touch me?"

"Yes, very much."

"Touch my cock?"

"So much."

"Do you want me to put my hands around your fat shaft?"

"Oh god."

"Stroke you up and down?"

"You're getting me so hot..."

"Do you want me to suck it?"

"Oh god yeah."

"I want to suck you, Daddy."

"I want you to."

"Will you hold my head while you move your cock between my lips?"

"Oh yeah, I want that. I want to fuck your mouth."

"I want to make you cum."

"Yes yes, so close!"

"I want to cum while you shoot your cum into my mouth."

"Oh sweetie, I want to shoot in your mouth."

"You're making me want to cum now. Do you want to see me cum for you?"

"Yeahhhh, cum for me baby!"

"Thinking about your cock while I shoot."

"Oh you sweet boy."

He stroked his cock faster and faster. I took one or two more strokes and a fountain of cum shot out of me.

"Oooh daddy, you made me cum!!"

"Yeah baby, now I'm cumming too."

"Oh yeah, daddy. So much cum."

I watched his grip slide to the base of his shaft and then a torrent of thick, white sperm flooded out of the end of his monster meat. It shot up onto his hairy pecs and his stomach, dribbled down over his knuckles and into his pubic hair.

We were silent for a few seconds. Both catching our breath. Then he said he had to go. Told me how great it had been. And I said the same. Told him he had a beautiful cock and I loved watching him wanking. 

He asked if I wanted to do it again sometime and, of course, I did.

We agreed on a time in two days. 

"My name's Dave, by the way." he said.

"I'm Robbie." I told him. Already, the anonymity of the web was being eroded but, after such an intimate encounter, I already felt we had passed that point.

"Robbie, would you do something for me?"

"What's that?"

"I like your smooth body... but I'd realllllly like it if you were smooth, uh, everywhere."

"You want me to shave my cock and balls?"

"You'd make an older man very happy."

"You're not old. What are you, 40?"

"Fifty two, so... thanks! Um.. anyway..."

"Well, I guess I'll shave if you want. But not you, Dave. I like your body hair!"

"Don't worry, I'd never be able to explain it to my wife!"

Ah, so he was married. 

I had just assumed he was gay, but then, I wasn't thinking of myself as gay, either, even after what we had just done and how hot it had been. 

Sure I looked at gay porn, but I'd never participated in it before. And this was just harmless role-playing.

As un-gay as I was, I hurried to the bathroom I shared with the other two guys in our house and complied with Dave's request. 

The act of shaving myself for the potential pleasure of another man was so erotic that I had a monster erection the entire time I stood in the shower, carefully ridding myself of all my pubic hair.

I loved how it felt after all my pubes were gone. I couldn't resist wanking off again. 

I was so smooth, my own penis felt unfamiliar to me. It was easy to pretend it was a different person's cock in my hand. 

That's what I imagined when I ran my hand up and down its straining length: that I was actually jerking off someone else. 

In a few moments, I was cumming. The cum splashed onto the bottom of the tub and I got on my knees to clean it up and make sure it all washed away. While I was down there, I imagined being on my knees in front of Dave's big hard cock. Imagined sucking it. I was out of control. All these new fantasies were running wild in my mind.

It made me feel quite feminine, somehow, to have bald genitals. And that led me to think about primping as a girl. What else would a girl do? Shave her armpits! Of course! 

Well, I was under the shower... The razor was there...

In only a couple of minutes, I had removed all the hair from my pits.

My leg and arm hair has has always been very sparse and light and soft, so I didn't consider going to town on those. 

Now the only significant hair on my entire body was on my head. 

It was weird, but I relished the erotic sensation of feeling so un-masculine. Once more my cock stood to attention and I couldn't resist stroking it. 

There was a knock on the bathroom door. 

"Hey, Robbie, is that you in there?" It was Pete, one of my housemates, home early from work.

"Uh yeah." I called out.

"Well hurry up! You've been in there fucking ages. I need a piss!"

"Sorry." I turned off the water, grabbed my towel and wrapped it around my waist. 

My erection still firm in front of me, was making a tent in the towel. I grabbed my clothes and held them over my crotch but, as I opened the door, the look in Pete's eyes told me I wasn't fooling anyone.

"Jeez, guy! You have a room for that..."

I feigned innocence but, as I hustled off to my room, I could feel my cheeks burning red.

Once back in the privacy of my room, I lay naked on my bed. I began caressing myself. Feeling the smoothness of my cock and balls, and my armpits. Feeling very feminine. 

I spread my legs wide as I began masturbating again. Imagining Dave and his manly, hairy body climbing onto me. His huge, fat cock nudging the opening of my ass. I stopped myself before I came. This was too much for what little inhibitions I had left.

I dressed and went down to the communal living room. Pete had brought pizza home and we sat together watching a ball-game as we ate.

After a little while he turned to me.

"You know, Robbie... there was a lot of hair in the tub, man. You know we have to keep the place better than that."

"Yeah, sorry Pete, I was just in a hurry to let you use the facilities. I'll go clean it up."

"Don't worry, I already did it for you. Just remember next time you do some 'manscaping'."

"What's that?"

"You know, trimming your pubes. That IS what you were doing, right?"

I laughed, ruefully. Pete had figured it out, but not entirely. 

"Yeah, busted." 

"Like I say, no problem. I won't say anything."

"Thanks, Pete, I owe you one."

He smiled.

That was Pete. A nice guy. He was always cool and even with the age difference, he just related.

Dave was already online when I opened up my cam the next day. I was pleased that he was there and flattered that he was early.

"Hey Robbie! Glad to see you."

"Me too, I've been excited to do this a second time, Dave."

I was wearing sweats today with no underwear. My incipient erection was already making a bulge. 

"I can see that. Do you want to show me?"

Dave was already nude and his large penis hung between his muscular thighs. 

I wanted to tease him a little bit. 

I hooked a thumb into the waistband of my sweats and very, very slowly pulled down at the front.

As I did this, I saw Dave's cock begin to swell. 

So exciting. A man was becoming aroused by me. By my teasing. 

I tugged the sweats lower. Now Dave could see where yesterday had been my pubic hair.

"Oh doll, did you do what I asked?"

"What do you think?"

"I think I might cum before we even get started!"

"Oh no, I want to see you stroke your big cock."

I tugged further. Now exposing the top of my rapidly stiffening penis. It was trapped by the sweats and uncomfortably pointing downwards, instead of straight up, like it wanted to. 

Dave began stroking his cock as I revealed my bald pubis. Then I couldn't wait any longer. Pulled my sweats all the way down and allowed my cock to spring free. 

"Oh baby! Such a sweet, sexy boy!" 

I moved closer to the cam so that my smooth skin was clearly visible. Lifted my cock so that Dave could see my shaven ball sack. Then I lifted that out of the way as well, showing him my taint and the cleft of my ass above the tops of my thighs.

"Oh yes baby, I like that. Mmmm, turn around for daddy."

I turned and showed him my bare ass.

"Do you like my ass? Is it a sexy ass?"

"Oh honey I want to kiss your sweet ass all over!"

I moved my hands down and spread my cheeks, bending over slightly.

"Does it excite you? Do you want to fuck me?"

I heard him groaning and turned around.

Dave was wanking himself furiously and I just had time to see him cumming.

"OH! So soon! Daddy cumming so soon!"

"Oh baby you made me cum! I'm sorry, honey. Sorry!"

"That's OK. I'm glad you liked me so much."

I stroked myself in front of the camera as I watched Dave run the palm of his hand over his cum-splattered stomach. His body hair becoming matted with his sperm. Glistening.

"I'll come for you now, Dave."

He moved and brought his face into view. It was the first time I had seen him. He was a good-looking, rugged man and it brought home to me what I was doing. Wanking off with another man. And loving it.

"Cum for me baby. I wish I could suck you off, and feel your cock spurting into my mouth."

Dave opened his lips. I moved close to the cam again. My cock filled his screen, his mouth filled mine.

"Cumming! Shooting in your mouth!" 

I came then, and my jizz spurted directly onto the camera.

"Yes! Cum on me baby!"

The orgasm subsided and I had to get a tissue to wipe the lens clean.

Since Dave had shown himself I decided to risk it and moved away from the camera so that he could see me from head to toe.

Standing there naked and hairless for the entertainment of another man was exquisite. 

"Oh honey you're so cute. Good-looking boy with a lovely slim body! What a dream!"

"Mmmm, thanks Dave. I'm glad you like me."

I swung my hips and my semi-hard cock whipped from side to side.

I turned around and let Dave see my ass again. 

"I wish I could be with you, Robbie."

"I wish that too. You could take my virginity. You make me feel like a little girl, about to be fucked for the first time. Scared and yet eager." 

The thought of being with Dave in person was inspiring. 

"Don't be scared baby, I would be so gentle. I would treat you as gently as any girl, if it made you want it more."

"Oh yes. I'll be your little girly boy."

"Mmmmm."

But then he had to go. Dave left me naked in my room. Cum still dribbling down the underside of my cock and over my hairless balls. 

Then I heard another chime. It was an invite from the first guy I had arranged a private session with. The one that had stood me up a couple of days before. 

I was still horny. I thought, why not? So I repositioned the camera onto just my cock and accepted the invite.

My cummy cock greeted the eyes of my friend and I could see him immediately start to stroke his hard, fat cock. I didn't speak and just fondled myself for him while he jerked off.

Turned around. Spread my ass. Attempted to twerk, even. I looked back over my shoulder at the monitor and saw his fist rapidly pumping up and down over his meat. 

"Put a finger in!" he told me.

I'd never considered it, but I was utterly into doing what I was told.

I ran my index finger over my belly to catch some of the cum that still clung there and then moved it to my anus. Just the tip of my finger gave me a thrill. Knowing I was going to press in. Giving a show for a second man in less than half an hour.

I pressed. The tip entered my hole. I heard him gasp. I pushed further and slipped my finger in up to the second knuckle. I felt resistance for a moment but found a way to relax and then began to thrill at the sensations I was feeling.

I pulled almost all the way out and then pushed back in. And again. And again, faster.

I was finger-fucking my own ass.

"Mmm yes. Like that. Do it like that. Sexy boy, sexy ass. My cock is so hard for you."

"You want this? My ass? Want to fuck me? I want you. I want your big cock. I want to feel you enter me. Fucking me. Your big cock. In me."

It went on like that for only a couple of minutes. I kept my ass to the cam the whole time. My digit never completely left my hole. In and out for his entertainment, until he came. 

Thick gobs of cum shooting up and trickling down of his fist as he pumped it up and down. Catching in his thatch of pubes. 

"Mmmmm so good. You came so good!"

It had been exciting as hell to watch as he came, and I wanted to cum again.

I turned around and started stroking my cock which was iron-hard once again.

And then he just broke the connection. I'd entertained him by fingering myself for him, then he'd got his nut and wasn't interested in whether or not I came at all. Just fucked off. Not even a word of thanks. 

What a cunt! I felt used. 

Not like my nice first experience, at all. Which somehow made me more attracted to Dave. It made me want to please him more. 

I thought about being girly for him. I thought I would give him a surprise for the next time we cammed. 

That evening I went to a supermarket which carried a small selection of clothing and purchased girl's panties. On a whim, I decided to go for a full outfit. I was pleased that my small stature made it possible to find a training bra, white knee socks and short pleated skirt as well. I used the self-checkout lane to avoid embarrassment. Something I had learned to do when purchasing condoms as a teenager. I was nearly broke but felt a compulsion to please Dave. Moreover, the sexual fission I felt as I selected my purchases was enough to overcome good sense.

I went straight to my room, stripped naked and eagerly started to try on my new outfit the moment I got back. The panties I had picked out were like the shortest of shorts. 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.