Straight to Bi, Cam to Real Life

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, as well.

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

Who could say? But I was joining 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.

A few months went by. I was camming regularly, either solo or with Dave nearly every day.

I'd had a few dates with girls in the meantime, but they hadn't gone anywhere. I still felt straight, but I was fully immersed in my non-straight sexual exploration.

I came home from work one afternoon and the house was quiet. I remembered that nearly all of my roomies were away for some reason or another. Only Pete would have been there, but he wasn't in the living room or kitchen.

I made my way upstairs to my room.

As I went past Pete's door, I heard the strangest thing.

It sounded like my own voice. I stopped by the door and listened.

It was definitely me. From one of my cam sessions. I could hear myself teasing whoever was watching me. Offering my cock to be sucked and my ass to be fucked.

Jeez, was Pete one of the disembodied viewers I had been showing off to all this time and had he recorded me? I knew my face was never visible, except when I was with Dave, but had Pete recognized my voice?

I tiptoed to my room, worrying about what he knew.

As soon as I opened my door I guessed he knew everything. My laptop was missing.

I remembered, after all this time, about the default setting to record my sessions. Damn, Pete was looking at my computer and my saved cam-session clips.

I was so mad about the intrusion that I marched right over to Pete's room and burst in on him.

He was sitting in front of my laptop, His jeans and underwear were around his ankles and he was jerking off. Jerking off to a video of me. He was startled. His hand flew off his erect cock and he turned away from me while desperately trying to close the window on the screen.

"What the FUCK, Pete?" I yelled at him.

"Oh god I'm so sorry. My computer boot-drive died and I needed to do some work emails. I borrowed yours. I thought you wouldn't mind."

Pete scrambled to pull up his jeans and cover himself up.

I walked over and folded the lid of the laptop, silencing my voice as it begged for a cock to suck.

"I wouldn't have minded if you'd just done that." I told him.

And then a thought struck me.

"Hey, you took your computer for repair last month. I remember you mentioning it."

"Yeah. Uh... that's when I borrowed yours. I found some stuff. By accident."

"Well I guess my secret is out."

"No. I haven't told anyone. I've just watched the videos."

"How many?"

"Uhh... all of them."

"How many times have you snuck my laptop out of my room?"

"I don't know. Maybe... ten?" He looked up at me, sheepishly.

I was mad about the invasion of privacy and embarrassed by him knowing about my camming, but Pete was clearly embarrassed about what he'd done, too.

He was a nice guy, and I liked him. I couldn't stay angry.

"Well... fuck." I said. Capitulating to the circumstances.

I told him I was going back to my room and to bring my laptop back when he was decent.

Pete's knocked on my door a few minutes later, carrying my computer.

"I won't tell, Robbie. You're a nice lad. I'm sorry I found out. And sorry I've been watching you."

"It didn't look like you were sorry when I came in there."

"Well, no. You make hot videos."

"I didn't know you liked guys."

"I don't. I don't. I didn't. I don't know."

He was curious, I guess. Like a lot of men. Like me.

Pete sat in my chair and I sat on my bed and we talked about it for a while.

He said he found the video folder by accident and just looked at one, being nosy. He was surprised to see me, but it was exciting for him.

He admitted that he'd looked at gay porn before and some of it turned him on.

I asked what he liked and he said he liked the gentle fucking videos most of all. And ones where it was an older guy with a younger one.

"I like those too."

"And I really like the recordings of you, Robbie. I like when you say those encouraging words. Asking if the viewer likes what they see."

"I guessed that when I saw your hard cock."

"I never did anything with another guy..."

"Neither did I. Not in real life. Since I started camming I've begun to want to, though."

"And you've made me want to."

"Be with a guy?"

"Be with you. Just you. You're so sexy. I've wanted to go to bed with you for a month."

"Do you know what you want to do with me?"

"Not entirely. Something though. Something with a guy."

"I sometimes like to feel like a girl, Pete."

"I know. I'd like to make you feel that way."

I mentally forgave Pete for the privacy violation. Once I let go of that, I could see the situation. Pete is a handsome, mature man. The brief glimpse I had had of his equipment had been enough for me to know I wanted to see it again.

There's a first time for everything, I supposed. Push had come to shove. This opportunity was not one to spurn.

I told him to give me half an hour, then come back.

I jumped in the shower. Shaved myself all over the places that counted.

After I dried off, I picked out the panties I thought made me look the sexiest, then dressed myself up in those along with my skirt and bra and a silky slip that had just been delivered. Pete wouldn't have seen it yet.

My cock was hard. I was thinking about what we were going to do.

I was probably going to get fucked for the first time. I was definitely going to handle Pete's cock and almost certainly suck him off. I knew I wanted it.

I was ready soon enough that I had time to think.

This was going to be the first time I was with a man. I didn't know how far we would go, but it was a first-time experience. The kind that I loved to watch. I decided that I had to have a record of it. For me, and maybe to publish on one of those porn sites.

The more I thought about it, the more I definitely wanted to record what happened, but Pete might not want to. I felt guilty about what I did next, but I set up my cam such that it was concealed but would have a decent view of the room. Pete wouldn't know it was on.

I was starting to worry that Pete had had second thoughts when he knocked and entered. He was in a t-shirt and loose-fitting sweat-pants. Once glance told me that he was sporting a chubby and that it wasn't constrained by underwear.

I stood and walked over to him. Neither of us had shoes on. I was probably half a foot shorter than Pete and the difference added to the sense of being feminine. That and the clothes. And my underlying desire to have his cock in me.

He took me in his arms and looked down at me.

"Can we start slow?"

"Whatever you want, Pete."

He leaned down and put his lips on mine.

I hadn't expected that. All my cam sessions centered around just getting off. I stroked myself and showed my ass and offered my mouth for cock, but I hadn't once considered kissing another man.

And now this man, in real life, was holding me in his arms and kissing me. A second after he started, my surprise abated and I started to enjoy it. I was being held in the strong arms of another man while he kissed me deeply. His tongue was in my mouth. Really, genuinely enjoying it. He made me feel submissive, and I liked it.

My hand went to his head and I ran my fingers through his hair. His hand went down the small of my back and came to rest on my ass. He squeezed me there, and I felt him pulling me tighter to him. My cock was trapped inside my manties, pointing to my left hip. I felt Pete's erection straight up and reached down to adjust myself.

I got my cock pointing up and was ready to just rub against Pete for a while, but my hand was there and his cock was there and his mouth was on mine and I was hot for him and it just seemed like the right thing to do...

I undid the drawstring on his pants and reached inside.

We both groaned, simultaneously. He, for my touch, my grip on his hot cock; me for his cock in my fist. I was gripping a man's hard cock while he held me in his arms.

My lips left his and I looked up into his eyes. My fingers were curled around the girth of his penis.

"Do you want me to stroke it?"

"I don't know. This is so weird. You're a guy. I know you're a guy. I never did this. I'm a married man."

"I never did this either."

"But all those videos..."

"I was just doing things that felt nice and I like being watched. And I like teasing the men who watch. But I never touched a man's cock for real before."

"How does it feel?"

I gripped it tighter and stroked him up and down a little.

"I fucking love it. The weight of you cock on my palm."

"Your hand feels good."

"Should we get naked?"

"Can I be naked and you stay dressed like that?"

"OK. Does me being dressed like a girl help?"

"Maybe with my guilty conscience, but I've watched all your videos, Robbie. I've seen you dressed up and I've seen you nude and you turn me on either way."

"I'm very excited, too, Pete."

He reached between us and I felt him rubbing my hard cock through the skirt and panties.

"Would you give me a show, like you do on-line?"

I was reluctant. It might be embarrassing.

"Are you sure?"

"I'd really like it. Your teasing is what gets me over the idea of sex with a guy. When you move your body and ask those teasing questions, it just makes me want you so much."

I wanted him to want me. I was too close to fulfilling my fantasy to refuse.

"OK. You sit on that chair and I'll stand in front of you."

I watched as Pete stripped out of his shirt and sweats. He has a great body for an older man. Firm.

He sat and spread his legs. His dick stood erect.

"You can stroke yourself while you watch, Pete. That's what you've been doing, isn't it?"

He admitted that he had been masturbating as he watched me for two weeks. He had looked at my videos over and over before that. He had immediately been fascinated and obsessed by the idea of his housemate being a slutty femboy, but it took him a while to overcome his inhibitions and to accept that he was attracted to me.

"I'm glad your libido won out, Pete. I like you and want you to be my first man."

I started to move in front of him, rubbing myself seductively. Lifting my skirt, asking if he liked what he saw.

Showing him my panty-clad cock and ass. Bending over. Peeling down my panties. Spreading my cheeks. Fingering myself. Touching my torso and playing with my nipples under my bra. Telling him how excited he made me. Offering him my cock. Offering my mouth. My ass.

Pete unashamedly stroked his cock while he watched and answered my dirty talk with dirty talk of his own.

We were both working ourselves up to the point of no return. I was desperate for sex with a man now. His shame and guilt were not going to stop him from following through.