sissyboy jake’s first outing – part 1

It’s two o’clock in the morning.

The story I have to tell you started at noon yesterday and ended just after midnight. Twelve hours. The most incredibly intense twelve hours I’ve ever spent, though I can’t tell anybody about it. Except anonymously, which is why I’m writing this and hoping you will read it and enjoy it.

There is only one other person who knows the whole story. That person is Tiffany, my Goddess. Tiffany is watching me as I write this. Actually, I have no idea whether or not She is watching. All I know for certain is that I am transmitting live from the camera on my laptop.

She enjoys that, my not knowing.

Let me give you a more complete picture of me at this moment. I am sitting on a hard-backed wooden chair at a makeshift desk in the basement. I am wearing the same garter and stockings I wore all day, though they’re a bit torn and have runs.

The corset I’m wearing is the same color as the garter and so is the B cup bra. My titties almost fill the cup, I’m quite proud of that. No injections, just hormones and regular suction. I’ve tied back my long blonde hair, the weaves held though I was certain at times they wouldn’t. I left my makeup on, though it’s quite smudged, the mascara is still streaked down my cheeks.

My medium sized butt plug is up my ass. That was one of Tiffany’s absolute commands, that I push it in as soon as they were finished with me. She wants me to feel that cum up inside me all night long. I don’t feel it, but I know it’s there and that’s enough.

My cock is pulled back hard between my legs and secured with packing tape that runs halfway up my back. My balls are, well, let me tell you how Tiffany has me keep my balls. As She got to know me better, She poked and prodded and twisted and turned my junk every which way She could. Eventually, She found the exact point where my discomfort was at the maximum but permanent damage was at the minimum. She has me tape my balls flat against the insides of my thighs. As I walk, hell anytime I move at all, a wave of pain shoots through me, flashes of white behind my eyes and a twist in my stomach that makes me want to puke. She is brilliant and evil.

So, here I sit in my slightly chilly basement. I’m wearing a thin terry housecoat to keep me from shivering. It’s worn through in some spots. Tiffany brought it to me a while ago. She’d found it in a trash bin and felt it was “just right” for me. She allowed me to wash it, but there is a foul smell I can’t get rid of and I have to shower and scrub myself after I take it off.

I want tell you about my day, but there are a few other things you should know about me first. I am NOT gay. I am not bi, or bi-curious. I am not a transsexual, I am not gender-confused. But, I am submissive. Oh fuck, am I a submissive!

Tiffany and I had been flirting online for a while before that came out. I met Her in a BDSM video chat. She said She was a beginner and wanted to know what it would feel like to get a few spankings and maybe do a Glory Hole. I wanted Her immediately. Auburn hair, big brown eyes, lips that screamed “put a cock between these!” I was still pretty new, but we managed to have two or three good sessions with me giving her commands and her obeying them.

We arranged a meeting one weekend. I drove to Dallas and we met in a hotel lobby. A few drinks and we were upstairs in my room. I commanded her to strip down to panties while I got us some drinks.

When I came back into the room, She was still dressed. Suddenly, everything shifted. She took the drinks from me and told me to get on my knees on the floor. I stared for a few seconds, then she slapped me hard across the face.

“On your knees, bitch,” she growled. I dropped to the floor, still confused. The few times we played online, I was the Top. I assumed I would be the Top again. But, I was wrong. Completely wrong.

She slapped me again then told me to strip. While I did, She told me later that She spotted it in me immediately, sometime after our third video chat. I was trained to be The Guy, the smooth talker who could get any woman in his bed. And I did it well. But She’d heard something underneath it. Something that wanted to surrender. And She was right.

I’ve been Her slave ever since. I moved in with Her. She quickly found that cross-dressing pressed my buttons. I spent all of my time around Her wearing women’s clothes of one type or another. She taught me how to walk, how to do my makeup, and how to take a dildo down my throat without gagging. She took me out in public regularly, grocery shopping or trying on dresses. I was positive that everyone who saw me knew my secret. I have no idea whether that’s true or not, but it doesn’t really matter, does it?

She also spent weeks having me train my ass with various sized plugs and dildos. I could now easily take an average English cucumber or zucchini. I kept my body completely shaved and stocked up a variety of perfumes and lotions. She kept my head shaved so She could try me with a variety of different wigs and hairstyles. Just recently, She let me grow it back out. She dyed it blonde and had me pay for elaborate weaves that let it hang halfway down my back.

And now, months later, She decided She wanted me to start earning Her a little pocket money. And that’s where today’s story really begins.

At eleven-thirty this morning, my phone rang. It was my Goddess Tiffany. I’d been dressed since eleven, as instructed, and had been sitting in the front room waiting for my nails to dry.

“The taxi is here,” She said, then hung up. I felt sad. I had hoped She might come home and say goodbye, maybe wish me luck. Maybe even send me off with a Kiss.

I set the phone down and went into the bathroom to check my makeup one last time. My eyes and lips were colored a rich burgundy. I’d painted on wide eyebrows and brushed my cheekbones. My Goddess Tiffany had taped up a photograph to help me, I matched it as closely as I could. I wore two hoop earrings in each of my pierced ears and had put my tongue stud back in.

To keep my dress looking its best, I’d left it on its hangar all morning, still in the plastic from the dry cleaners. I’d spent the morning puttering around the house in my corset, garter and stockings. I wore a pair of soft slippers to keep them from snagging or tearing.

I dipped my finger in the burgundy pot and touched up my nipples, careful not to smear the color on my silver hoop piercings.

I went into the bedroom and put on my bra, then took the yellow dress out of its bag. I stepped into it and zipped it all the way up to my neck. All of my dresses had zippers up the front. Tiffany said She found it much more practical. It allowed me to dress and undress myself without any help.

I stepped into matching yellow high heels, then put on all of the bracelets She’d laid out for me.

I stared at myself in the mirror for a long time. I was pretty, I could more than pass as a woman. But I was about to be sold — correction, had been sold — to a pair of strangers who were going to have me as theirs for the rest of the day.

Tiffany hadn’t even bothered to ask me.

Exactly one week ago, while we were lounging in Her front room watching an old movie on television, She’d idly said, “oh, I may have forgot to tell you, but you’re going to spend next Friday with two men. Friends of mine.”

She reached forward and picked up a grape and a piece of cheese, not even noticing my stunned reaction. After a few more minutes, She took my hand in hers and brought it to Her lips, kissing it gently. I melted as I always did whenever She touched me.

“Look at me,” she said. I did. “You’re ready for this. Your hole can almost take my whole hand.”

She leaned closer and brushed the hair from my forehead. “They are going to want to use belts on you,” She said.

I could tell from Her eyes that She was getting turned on just thinking about it. I felt my cock stirring, tugging against the tape.

“Open your mouth,” She said. I leaned my head back and opened wide. She pushed Her fingers as far back in my mouth as She could. I felt the urge to gag but She’d trained me well and I didn’t.

“They will ream that pretty little throat of yours,” She whispered in my ear. I felt my nipples and cock responding. She leaned forward to kiss me and I eagerly responded.

I licked Her to orgasm twice, my fingers working deep insider Her, Her delicious Juices covering my face, my neck, my hands and forearms. I needed to cum badly but She was tired when I finished and just stood up and stretched.

She could see the question in my eyes.

“No, dear, not tonight,” She said, kissing my forehead. I followed Her into the bedroom and curled up on the rough carpet She kept beside Her bed. I cried myself to sleep.

But all of that was last week.

I picked up the handbag She’d prepared and looked inside. A single tube of lubricant, some spray perfume, breath mints, and a pay-per-use cell phone. Everything a whore needed to get on with her business.

The taxi drove for twenty minutes, away from our apartment, onto the freeway then into a residential neighborhood. My stomach was twisting and turning the whole time. I wasn’t sure I could go through with it. Everything up until now had been fantasy, roleplay. This would be real people touching me and expecting me to touch them back.

The The taxi turned off the two-lane and onto a side street. The driver pulled up in front of a big two-story place with a pair of black Mercedes in the driveway. Solidly upper-middle class, not too pretentious but not too shabby.

I got out and stood there for a full minute, staring at the house. I started when the phone rang.

“Are you there?” Tiffany asked.

“Yes, Goddess,” I answered.

Tiffany was silent for a few seconds. I thought She might change Her mind, tell me that it was all a joke, a test. Instead She said simply, “make me proud,” and hung up.

The men called themselves Rashid and Karl.

Karl was European, probably German. Six foot two with close-cropped blonde hair and an athlete’s body. He was deeply tanned and had a scar that ran across his left cheek, stopping just short of his ear.

Rashid was darker, I guessed either Indian or Middle-Eastern. He was smaller and slimmer but he scared me. He looked at me with such intensity, as though he was already seeing me helpless and destroyed there on the floor in front of him, begging for mercy but expecting none.

“May I take your purse?” Karl asked, his voice pure ice. I nodded and handed it to him. He opened it and took out the contents, one by one.

“Lubricant. Wise.” He turned and tossed it across the room. It landed in a trash canister, “but pointless. Breath mints, yes. And perfume.” He came close to me and sniffed. He smiled. He gave a small spray on each side of my neck and put the spray back in my bag.

I was already shuddering. There was no way I could go through with this. The intensity in the room was palpable — just the level of control they were showing, the cold, almost mechanical way they were going through the motions, was terrifying.

Karl put his hand on my shoulder and turned me toward him. I moved slowly, as gently as I could, trying to be alluring, to send some kind of ‘be gentle with me’ signal.

He leaned forward and brought his mouth slowly closer to mine. My mind raced, what kinds of things did I want from a woman? I pushed my hips forward, trying to press my belly and thighs against him. I put my arms around his neck and pulled myself close.

I heard Rashid snort from behind me but tried to ignore him. I felt him step closer, his body pressing against me from behind.

I opened my mouth for Karl’s tongue. His hand grabbed my jaw and opened it wider. Karl spit a huge glob into my mouth. At the same time, Rashid’s hand came up between my legs, the two mounds of his palm expertly finding and crushing my balls. My knees went weak. I would have collapsed if Rashid hadn’t caught me under the arms.

I felt Rashid pulling me backwards, dragging me across the room and down a hallway. Karl followed, his face twisted and angry. My high heels slid off, Karl picked them up and threw them back into the front room.

Rashid pulled me down a flight of stairs and into the basement. It was unfinished concrete with a ten foot ceiling. I felt my heels scraping against the floor and tried to walk but kept losing my balance.

He dragged me through a doorway then dropped me to the ground. I scraped my palm and elbow.

“Stand up, whore,” Rashid barked. The man who had been so quiet upstairs was now calling out the orders. I got up and stood, my feet shoulder width apart, hands behind my back. Exactly as Tiffany had trained me, I realized.

Rashid walked around me, staring at me, hands behind his back. “You make me sick. You are a twisted, sick pervert who doesn’t know if he’s a man or a woman.” He smacked me across the face hard, then backhanded me, did it again.

Karl had come into the room and was watching silently. He closed the door behind him and locked it. I was scared. How well did Tiffany know these two?

“Show us what you can do,” Rashid said. He nodded toward one of the structural poles. I did my best to think back to the topless bars I’d gone to years ago, to remember the moves, the poses. I wrapped my leg around the pole, sliding it up and down, feeling the cool metal against my thigh. It felt good and I let myself enjoy it. I unzipped the dress and let it fall away, kicked it toward the wall with my foot. For some stupid reason, I wished there was music.

Karl and Rashid had their pants off now, their cocks hanging limp between their legs. I got to my knees on the floor and crawled toward them, onto the thin pad where they were standing.

I slid my hands up Karl’s tree-trunk legs. My right hand went up the inside of his thigh and I saw his cock start to move. He was unbuttoning his shirt and I smiled up at him. He looked away.

My fingernails were scratching lightly across the underside of his sack and I heard him moan. I inched slowly around in front of him and brought my mouth close to his cockhead.

This was it, the moment of truth. I realized suddenly that I’d never had a man’s cock in my mouth before. I felt dizzy and swayed slightly. He grabbed my hair. I was afraid the weaves would pull out but they held. He jerked my head backward and I instinctively opened my mouth.

Karl turned to Rashid, “watch.”

He pulled me upward and slid my face over his cock like he was pulling a sock onto his foot. He was getting hard and in just a few strokes, he was past the back of my mouth and into my throat. He fucked my face deep and slow. My eyes were tearing up and I was breathing hard through my nose. I wrapped my arms around his iron-muscled legs and held on as he reamed my throat.

After a few more strokes, he pulled me all the way up and held my nose so I couldn’t breathe. I started to panic, clutching his ass hard, digging my nails into his bottom. He jerked my head back, a trail of slobber dripping from my mouth to his cock.

He slapped me hard and growled, “don’t scratch my ass, you cunt!” I shook my head and cried, feeling the tears running down my cheeks and neck. He rammed back into my throat and held his cock there for a long time, flexing the head and moving up and down almost imperceptibly.

I started to see black again and hammered at his ass. He pulled his cock out of me and I gulped air like a drowning man. Then he was back in me again, deep as he could be, his strong hands holding me tight against his belly. I couldn’t believe how long his cock was and that he had it down my throat.

I started seeing spots again when I felt someone’s hand between my legs. Rashid. He pulled down my panties and pushed my knees apart.

Karl took his cock out until just the head was in my mouth. I licked and sucked eagerly, hoping I could make him cum before he skull-fucked me again.

I’d lost track of Rashid’s hand until I felt his fingers slide up my ass. I groaned, my cock responding by trying to swell against the tape. Rashid laughed and ripped the tape down my back. I barely held back a scream.

Then, he jerked it again, ripping it off of my cock. I cried that time. My cock and balls were free now, hanging exposed and helpless between my legs. I felt his hand around my shaft and nearly came. But he let go and slid his fingers back up my ass.

“Can you lube yourself back here, honey?” he asked, his voice mocking and harsh. He pulled his fingers out of me and I felt his cockhead at my asshole. “Ready?”

“Fuck, no, please, no, let me get you wet!” I begged but he ignored me. Karl rammed his cock into my mouth again and Rashid tried to push into my ass. He couldn’t get in though, I was too tight. He kept trying. I tried to relax, to remember everything Tiffany had taught me, but it was no use. I was clenched tight as a knot.

“You’d better let me,” Karl laughed. “I’m slicked up.”

He pulled out of my mouth and stood up. I collapsed, my face and shoulders on the floor, my ass up high and open. Karl got to his knees behind me and grabbed my hips. He opened my cheeks and slid his cock into my ass, burying himself deep in me with a single stroke. I felt myself clenching, my cock twitching and knew I was going to cum.

I’d never felt anything like it before, not the dildoes, not the butt plugs, not the enemas. This was completely different and my body didn’t know what to do except respond. Karl slid slowly all the way out and told me to catch my breath. I gulped air and tried to calm down. I relaxed my ass as well as I could. He slid in deep again and I moaned. It was better than I’d dreamed, feeling that shaft and head sliding up into me until his balls pressed against mine, all soft and hot.

With his third stroke, I came all over the pad. The two of them laughed and Karl started humping me harder. I looked at Rashid and opened my mouth, eager for his longer, thinner cock to be in my mouth. I was a fucking machine, all warm, damp meat for them to use. And they did. They both came up my ass twice before they took the first break of the day.

. . . to be continued?

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