Roommate's Sissy Blackmail

I had a "secret" collection of lingerie...and sex toys.

Often, I slipped on a pair of panties, and admired my lean, fem-ish body in the mirror. I pranced around my room, wishing I could somehow do this....in a "larger" manner. Next, out came my sex toys, (then out came my rock hard penis)....and jacked off.

At 21, I was an attractive boy...and equally attractive sissy.

One night, I'd had a few too many, and passed out with my door open, and my roommate Steve saw me passed out in a bra and panties...and took photos. I had also left my "sissy-drawer" open, so he saw the rest of my "sissy clothes".

Steve had money. The apartment was in his name, he had a nice car...I sort of coat tailed off his money, and already was a bit beholden to him.

He owned a boat and we waterskied, at every chance. I'd always worn Speedos, and he wore regular trunks. We were in the middle of the lake, just drifting, sipping beers, and Steve said, "I think I know why you wear Speedos," and without waiting, showed me the photo.

I was speechless!

He smiled, "You're a great looking guy...and even a better looking slut!"

He had a sort of evil look on his face, "What would people say?"

I stammered, "It's...."

He interrupted, "I've had fantasies of blackmailing someone, and you just fall in my lap."

In desperation, "Steve...Please!"

He replied, "We can do it easy....or rough."

I remained silent and he went on, "I want a blowjob, right here, right now, and I'm going to take photos of you with a dick in your mouth. I'm going to cum in your mouth and you're going to swallow."

He took off his swimsuit and sat back in his seat, "Take off your Speedo and on your knees. You can stroke yourself while you blow me. Needless to say, don't cum until I say you can."

I started to protest, but there was nothing to say; I was going to become his sex slave, or suffer consequences. (Our "friendship" was over...a new relationship was at hand).

I stood in front of him and took down my Speedo.

His cock was soft, but I was starting to get hard, and he smiled knowingly.

He squirted suntan lotion into my hand, "I want you to enjoy it too. Make yourself hard."

In seconds, my cock was at attention, and he took a photo. "Get to it," he ordered, and I slid to my knees.

He slid forward, and his cock was inches from my lips.

I opened my mouth and took his cock between my lips. I worked my tongue, and bobbed my head, and his cock hardened in my mouth.

In a moment, I looked up, and his camera clicked, and my life was forever changed.

As I looked up, he took a couple more photos and emailed them to a secure email.

Then he set the phone aside and grabbed my head, "I knew you were a slut. This is the best suck job I've ever had," as he guided my head with his hands. "Deeper, slut!"

I took his cock deeper and he held my head in place, my tongue darting furiously.

I started to gag and he let me back off, and I returned to bobbing my head and working my tongue. "Lay back, on the floor," he ordered, and he straddled my face. He sawed his cock in and out. I couldn't move, somewhat trapped under him. Looking up, I could only see his belly, and his cock working in and out of my mouth. He was literally fucking my mouth!

Then he was still! He eased his cock deeper, such that it was near my throat, and he groaned as his first shot jetted into my throat. I swallowed and more cum blasted into my mouth, and more, and I swallowed. All the while I'd been stroking my own cock, and now I came....like never before!

His cock still in my mouth, I groaned as I shot my cum up onto my stomach, while he slowly continued pumping in and out of my mouth.

I was still working the last drops out of my cock as Steve arose, and sat back, straddling me, looking down at me.

He slid back, straddling my waist, he dipped a finger in my cum and presented it to my lips, and I opened with no protest, and he continued...bringing his cum covered fingers for me to suck. "You like being a slave, Don't you?" I nodded.

We headed back home without much discussion. Coming down from the days events, still in my Speedo, I crashed on the couch, into a deep sleep.

On awakening, Steve was sitting at the other end of the couch. I had a hardon inside my Speedo. He casually reached and lightly stroked a finger up and down my cock and I moaned. "Did you have a nice nap, Tinker Bell?"

He continued stroking me and commented, "I've always wondered why you wore Speedos, while the rest of us work regular trunks. At some level, I knew you were a twink."

"I've been exploring your sex drawer. Let's go have a "fashion show".

My cock was still hard in my Speedo as we walked to my room.

In my room, he had me dump everything onto the bed...various panties, bras, a bikini I'd stolen from an ex-girlfriend, various camisoles, high heels, two dildos, (one for my mouth and one for my ass-pussy), and a butt plug.

Steve picked up the plug, "What's this about?"

I stammered, "It's a plug, to stretch your ass."

He smiled, "Put it in...Let's stretch that ass."

I took down my Speedo, my cock still semi-hard, and he commented, "By the way, lose the pubes...and the rest of your body hair." He saw the fear on my face, "If anyone asks, say you're back into competitive swimming."

I nodded, and he added, "From now on, it's "Yes, Master."

I whispered, "Yes Master," then lubed my ass, and started working the plug in.

Observing, he seemed impatient, and I panted, "It takes a minute. I can't just shove it in....my body has to adapt. Otherwise, it really hurts."

He nodded, "And once it's in, then what?"

I shuttered as I spoke, "It takes about 15 minutes, then I'm stretched where I can use a dildo without any pain."

"So you've already been fantasizing being fucked by a guy? Does that make you Gay."

I answered, "I've had bi fantasies, but I mostly fantasize about women."

He asked, "What about your Sub fantasies?"

"They've always been where I'm sub to a woman, but...." I drifted off as the plug slid in all the way, causing me to close my eyes, put my head back, and breath hard.

"Nice," he said, tossing a panty to me, "Put these on."

Recovering from the plug "intrusion", I slid the panties on. They fit nicely; containing my balls, allowing my cock to slide to the side, while the rear thong slid between my cheeks, and nestled against the plug, such that you couldn't tell there was a plug in my ass.

He tossed an "A" cup matching bra, and he noticed how efficiently I maneuvered it on, "I see you've had a lot of practice."

I answered, "Yes Master," and he stood, "On your knees," as he dropped his shorts.

For the second time that day, his cock entered my mouth. The plug in my ass stoked my eroticism, and I lightly stroked my cock thru my panties...wishing I could also touch my nipple thru my bra.

As he fucked my mouth he commented/ordered, "I like your femmed up look. When we're here alone, that's all you ever wear, sissy clothes."

"Ye Aster," was the best I could answer with his cock in my mouth.

He ordered, "Get that dildo. I want to see you fuck yourself with it."

I said, "Can I lay on the bed? It works better that way."

He watched me grimace as the plug eased out, and then my pleasure as the dildo slid effortlessly, in and out of my "sissy-pussy". (At that moment, I couldn't help myself....I wanted him to fuck me).

He smiled, "You really are a twink, aren't you?"

He slid onto the bed and I turned onto my back and raised a leg.

He asked, "Ever been fucked before?" I turned my head, "No."

"Looks like a first for both of us," as his cock slid (quite comfortably), into my sissy pussy.

He fucked me in silence, and then said, "This is unbelievable! What a (literal) piece of ass!" He took his time, easing in and out, enjoying his "piece of ass".

Then he picked up his pace. His arms gripped me. Then he came, and I felt his warm cum inside me. He continued stroking...noticing the additional lube of his cum, he ordered, "This is nice! Next time, use more lube."

"Yes Master," I answered, wanting to cum myself.

As if reading my mind, he ordered, "Go shower, and shave everything....and don't beat off....don't cum, you horny slut."

"Yes Master," I answered.

I emerged from the shower, and fixed my longish hair in a more coiffed, femmy, style, put on a fresh pair of panties, a cami, and presented myself to my new Master, hands locked behind my neck....my cock was hard in my panties.

Sitting on the couch, he said, "Nice. I might have to fuck you one more time before the night is over. Lay on the floor, beneath my feet, and give me a foot rub."

"Yes Master," as I massaged one foot, the other rested on my panties...on my cock...nudging, keeping it hard.

It was time for bed, and we slept together in my bed. But first, he made me insert the plug, and then panties. In the middle of the night, I awakened to him tugging at the plug. I silently removed my panties and the plug, and he quickly slid his cock in. My back to him, both on our sides, he fucked me hard and fast. Then he went back to his room, and I desperately jacked off as his cum dribbled out of my sissy pussy.

In the morning, I wore a bra and panties, and a cami, and again, fixed my hair in a most femmy fashion, and he approved, "You were made for this! Do you have makeup?"

"Lipstick," I said, but that's all.

"Go put it on," he ordered.

When I returned he said, "You make a better looking girl than guy!"

He motioned as he took down his pants, and I was on my knees before him, "Should I put the plug in?"

"Maybe later," he said. "Just suck me off for now. Man, I love those lips! Go get some makeup today. I want to see you made up," as my head bobbed on his cock.

As I served his cock, he gave another order, "Get some laxatives and enemas too. I want you clean as possible."

Then he came in my mouth. I didn't swallow right away. I really tasted his cum for the first time. It was the same as mine..."Not bad," I thought, and then I swallowed.

That afternoon I watched videos on applying makeup, and that evening he came home to his sissy slave dressed in garters, stockings, and heels, plus panties and a cami, hair femmed up, and full makeup. I was plugged, and hard in my panties.

"If you had boobs, no one would know you're not a girl! Lay back on the bed."

I laid back and spread my legs. He could see the flange of the plug, "Did you clean your ass?"

"Yes Master."

"Then get unplugged," he ordered as he undressed.

My hole gaped open for him, "I'm already lubed up," I said.

He kneeled between my legs and leaned into me, and his cock slid in. He looked upon me and as his cock sawed in and out, he shook his head, "What a piece of ass you are!"

Eyes closed and head back, I mumbled, "Thank you, Master."

He fucked me like a girl, on my back, legs spread wide.

I reached down and slowly started stroking myself, but he laid down on top of me, face to face...our lips just inches apart. But he didn't kiss me. He put his head into the mattress, next to me, and grabbed my ass with both hands.

My hands were somewhat trapped to my sides, so I remained completely passive as he fucked me. My cock got no stimulation, but I felt orgasm approaching just from being fucked in my sissy pussy.

He came just before I could. His cum was warm inside me, and his full weight was on me as he basked in afterglow, slightly pumping his final drops into me. His cock began to get small, and he slipped out and stood up. I reached for my throbbing cock and he said, "Don't cum just yet," and he headed to the shower.

Master returned from his shower, and I still laid there lightly stroking my hardon.

I had replaced his cock with a dildo, and I was dying to cum.

He stood there drying himself and I began working the dildo and stroking my cock as he stood and watched me. In just seconds, cum shot all the way to my face...he laughed and walked away.

That night, he met Samantha.

In days, they'd shared their sexual kinks, and both liked the Dom role.

It became the three of us, and "Mistress" Sam used me the same as Master Steve. On the boat, she was topless, while I wore a bikini...top and bottom. I gave them both massages, and they fucked right in front of me, while I kneeled submissively... then I licked them clean.

Mistress knew a Sub girl, Joy. (They were close at one time, and Joy had shared her fantasies...Sam decided now was the time to pounce).

We served as their slave-couple.

There were no limits; they stretched our sexual boundaries beyond anything I'd have imagined...taking us to "play-parties" where we served large groups, where we were subjected to their sexual whims.

Then Sam got a transfer, and they were gone...

Joy and I were in shock. There were a few phone calls, but that was it...over...done.

Joy and I tried other Dom couples, but nothing clicked.

Joy doesn't want a sissy-sub hubby.

We live together, but she fucks other guys.

She is sub to them, and I'm sub to her.

To the reader:

Shall the story continue?

How depraved can it get for our sub-sissy????